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$2,795,000
4 Beds 6 Baths
Within the prestigious Sanctuary section of The Peninsula on the Indian River Bay, 27668 Sterling Boulevard presents an extraordinary opportunity to experience one of Delaware's finest luxury golf and waterfront residences. Perfectly positioned on a premium golf-front homesite overlooking the 7th green, this exceptional three-story home, with a private elevator, captures breathtaking panoramic views of the Indian River Bay, the inlet, and the manicured fairways beyond. Multiple balconies, a screened porch, and an expansive paver patio create exceptional outdoor living spaces where bay breezes, spectacular sunsets, and picturesque golf course vistas become part of everyday life. Inside, sophisticated coastal elegance meets timeless craftsmanship. Wide-plank engineered hardwood flooring extends throughout the second and third levels, while an inviting foyer opens to a beautifully designed floor plan. Rich architectural details, including extensive crown molding and elegant coffered and trayed ceilings, create a refined yet welcoming atmosphere. The inviting living room is anchored by a gas fireplace flanked by custom built-ins and a wall of sliding glass doors that seamlessly blend indoor and outdoor living while framing the spectacular waterfront setting. Designed for both entertaining and everyday living, the gourmet kitchen showcases an expansive center island with seating, crisp white Craftsman-style soft-close cabinetry with display cabinets, a five-burner gas cooktop beneath a custom range hood, Bosch double wall ovens with a built-in microwave, a classic subway tile backsplash, and premium finishes throughout. A custom built-in banquette offers the perfect spot for morning coffee or casual dining while taking in the surrounding views. The adjoining wet bar, complete with a beverage refrigerator and sink, enhances entertaining, while the elegant dining area provides a beautiful setting for more formal gatherings. The main living level also offers a private guest suite with an ensuite bath, a home office with custom built-ins, a powder room, and direct access to the screened porch and balcony. The upper level is dedicated to luxurious comfort. A spacious family room provides an additional gathering space, while the primary suite offers private balcony access overlooking the golf course and bay, a spa-inspired bath with dual vanities, a soaking tub, a walk-in shower w/bench seating, and a custom walk-in closet. Two additional bedrooms, each with private ensuite baths, provide exceptional comfort and privacy for family and guests. The entry level is designed for recreation and entertaining, featuring a spacious recreation room with a custom wet bar and beverage refrigerator, a convenient powder room and a versatile flex room ideal for a home gym, hobby space, or an additional bedroom. Step outside to your private resort-style retreat where a paver courtyard features a built-in grilling station, hot tub, fire pit, raised seating walls, and sweeping views of the championship golf course and Indian River Bay. It is the perfect setting for entertaining or simply relaxing after a day on the course or the water. Additional highlights include two tankless water heaters, Andersen hurricane-rated windows and doors, a partial-house backup generator, an irrigation system, a surround sound system, and an oversized two-bay garage with a tandem bay designed to accommodate another vehicle, kayaks, paddleboards, bicycles or just perfect for extra storage! Life at The Peninsula is equally extraordinary. Residents enjoy one of Delaware's premier private resort communities, highlighted by the Jack Nicklaus Signature Golf Course, indoor and outdoor pools including a wave pool and adults-only oasis, a full-service spa, state-of-the-art fitness center, tennis, pickleball, basketball, mini golf, a private bay beach with kayak and paddleboard access, miles of scenic walking trails through an Audubon Certified Nature Preserve, and fish pier.

27668 Sterling Blvd, Millsboro

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$950,000
3 Beds 3 Baths
This exceptional 2020 built Schell Brothers Jasmine model has been meticulously maintained and is ready for immediate enjoyment in the prestigious gated community of The Peninsula on the Indian River Bay, where refined coastal luxury and world class resort living come together seamlessly. Perfectly positioned on one of the largest premium homesites in the neighborhood, this elegant 3 bedroom, 2.5 bath residence offers approximately 2,300 square feet of thoughtfully designed living space filled with upscale finishes, soaring ceilings, and sophisticated architectural details throughout. An expanded garage, expanded bonus room, and beautifully designed floor plan provide exceptional flexibility, while thoughtful upgrades throughout the home enhance both comfort and style. From the moment you step inside, you are welcomed by a foyer and an airy open concept design that seamlessly connects the great room, living room, and dining area. Rich upgraded wood flooring flows through the great room, where soaring two story ceilings and a stunning gas fireplace with a premium granite surround and mantle create an inviting focal point. Recessed lighting, ceiling fans, beadboard panel doors, painted interior walls, and upgraded faucets throughout further elevate the home’s quality and craftsmanship. At the heart of the home is a beautifully appointed gourmet chef’s kitchen designed to impress, featuring granite countertops, an oversized center island, upgraded premium cabinetry, GE Profile appliances, double wall ovens, a gas cooktop with hood, coffee bar, pantry, and abundant storage. The seamless flow between the kitchen and living spaces creates an ideal setting for entertaining family and friends. The luxurious first floor primary suite serves as a private retreat, complete with a tray ceiling, two spacious walk-in closets, and a spa inspired ensuite bath featuring dual granite vanities, a large walk in shower, and abundant natural light. A generously sized laundry room with additional storage enhances the home’s everyday functionality. Upstairs, you’ll find a spacious loft, a dedicated tech nook perfect for a home office or study space, two oversized guest bedrooms, and a full bath. A huge unfinished storage area offers endless possibilities and could easily be transformed into an additional bedroom, media room, fitness space, or private guest suite. Outdoor living is equally impressive with an oversized screened porch featuring elevated ceilings that overlooks the expansive backyard. Perfect for dining, relaxing, and entertaining while enjoying the privacy of one of the community’s largest lots. Beyond the beautiful finishes, this home offers valuable behind the scenes improvements including the exterior house and trim being painted within the last year, fiber cement siding, a finished garage with painted walls, an epoxy coated garage floor, a climate controlled crawl space, and a tankless Rinnai water heater, providing lasting peace of mind and energy efficiency. As a resident of The Peninsula on the Indian River Bay, you’ll enjoy an unparalleled resort lifestyle with exceptional amenities including gated security, an elegant clubhouse, the renowned Jack Nicklaus Signature Golf Course, driving range, state of the art fitness center, indoor and outdoor pools, wave pool, hot tubs, sauna, spa room, tennis courts, pickleball, dog park, community garden, nature center, private bay beach, fishing pier, and miles of scenic walking trails. Located just a short distance from these extraordinary amenities, this exceptional home offers the perfect combination of luxury, thoughtful upgrades, and resort style coastal living in one of Delaware’s most sought after waterfront communities.

33012 Shadeland Ave, Millsboro

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$1,345,000
4 Beds 3 Baths
Welcome to 27551 Medallion Avenue, an exceptional golf and waterfront home in the prestigious gated community of The Peninsula on the Indian River Bay. A rare and highly sought-after offering, this property provides the next owner the opportunity to obtain immediate Reserve Membership, bypassing the typical golf membership waiting list. Perfectly positioned along the 10th fairway and green, with two ponds and sweeping views of the Indian River Bay, this meticulously maintained four-bedroom, two-and-a-half-bath residence offers refined finishes, quality improvements, and an exceptional resort lifestyle. Exceptional curb appeal begins with a beautiful paver driveway and front walk, professionally landscaped grounds, a lush, irrigated lawn, and timeless architectural details, including shake accents, horizontal and vertical siding, board-and-batten shutters, multiple roof peaks, a bronze pineapple weathervane, and a welcoming covered front porch enhanced with new TimberTech decking. Inside, rich hardwood flooring extends throughout the main level, complemented by crisp white wainscoting, plantation shutters, beadboard accents, and elegant crown molding. Just off the foyer, a formal dining room offers the flexibility to serve as a private home office. Designed for both everyday living and entertaining, the gourmet kitchen features granite countertops, a breakfast bar, new stainless steel GE Profile appliances (10/24), double wall ovens, a four-burner cooktop, a new Broan stainless steel range hood, display cabinetry, under-cabinet lighting, pull-out drawers, two pantries, and an appliance garage. The adjoining casual dining area opens to a screened porch with an Eze-Breeze enclosure and a beautifully designed two-tier paver patio with raised sitting walls and a pergola, creating inviting outdoor living spaces that overlook the golf course, ponds, and Indian River Bay. Anchored by a cozy gas fireplace, the great room captures these extraordinary vistas through expansive windows, ensuring the home's remarkable setting remains the focal point throughout the day. The first-floor primary suite offers a tray ceiling, elegant round transom window, two walk-in closets, and a luxurious en suite bath with dual granite vanities, a soaking tub, frameless glass walk-in shower, and a private water closet. Upstairs, a spacious loft connects three additional bedrooms and a full hall bath. The large guest bedroom features two walk-in closets, including an oversized closet positioned above the powder room that offers the opportunity to create a third full bath, establishing a future second primary suite if desired. An adjoining bonus room provides excellent storage or flexible space for hobbies and seasonal items. Ideally located just a five-minute stroll from the clubhouse and amenity center, residents enjoy access to The Peninsula's exceptional amenities, including the Jack Nicklaus Signature Golf Course, elegant clubhouse with dining, full-service spa, fitness center, indoor and outdoor pools, an adults-only heated pool, wave pool, sandy beach, tennis, pickleball, basketball, scenic walking and biking trails, and a vibrant social calendar. Conveniently located near historic Lewes, Rehoboth Beach, shopping, dining, and Delaware's award-winning beaches, this exceptional home offers the perfect blend of luxury, comfort, and coastal living.

27551 Medallion Ave, Millsboro

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$2,095,000
7 Beds 7 Baths
If you’ve been searching for that contemporary, coastal, custom home that can easily host a multi-generational family reunion and yet can easily be enjoyed as a cozy and intimate retreat, perfect for a couple’s relaxed life-style, welcome home. Ideally sited on a coveted premium lot with expansive water views of protected wetlands and the Peninsula’s championship golf course, this sensitively designed home marries distinctive architectural features with nature’s beauty, offering a front row seat for close-ups of Delaware’s native wildlife. The professionally landscaped front yard cottage garden greets you upon arrival. It’s anchored by two River Birch trees and alive with colorful native perennial and pollinator plants, stone accents and low voltage lighting to create night-time drama. Once inside the spacious foyer, includes many custom architectural details, like board and batten wainscoting, shiplap accents, coffered and tray ceiling designs, crown moldings, and wide-plank, hand-scraped hickory hardwood flooring. Window treatments include remote-controlled, hard-wired, pirouette electronic shades and contemporary 2 ½” blade shutters. Designer light fixtures enhance the home’s coastal charm. Sonos built-in ceiling speakers allow you to play whatever music your heart desires. The great room’s exceptional features include a dramatic two-story wall of windows that flood the home with natural light and a soaring two-story stacked stone gas fireplace flanked by custom built-in cabinetry accented with lighted display shelves behind glass paneled doors. The first floor boasts two primary suites. The main owner's suite, a tranquil retreat focused on the spectacular views, features a sitting area, tray ceiling, a shiplap accent wall, dual custom walk-in closets, and a large spa-inspired bath. The second owner’s suite features a wall of windows offering sweeping views of the golf course, wetlands, local wildlife and also has a walk-in closet and an ensuite bath. Centrally located as part of the great room, the kitchen is anchored by a generous quartz-surfaced island faced in shiplap, providing a natural gathering spot. GE Monogram stainless steel appliances, including a 48” side-by-side refrigerator, a six-burner gas range and a suite of professional grade appliances that complete the space. Soft-close custom 42” cabinets are topped with lighted display areas that add another unique design detail. Two pantries, one a walk-in, and a large farmhouse sink enhance the kitchen’s easy functionality. Whether you’re ready to relax on the family-sized screened-in porch with coffee or cocktails to watch the wildlife and golfers, or to entertain a boisterous crowd, the 30’ long deck adds extra space to accommodate everyone. You may decide to take advantage of the space below the deck to add an outdoor kitchen, additional seating, a garden bursting with herbs and cutting flowers, or even a private pool. The carpeted staircase leading to the second floor is lined with shiplap wainscoting to protect the wall from the possibility of visitors’ luggage scrapes. A generous loft space, central to the second floor with an extra-large walk-in storage closet, provides a welcoming area for family gathering and games. The rest of the second floor continues the home's thoughtful coastal design with four additional bedrooms, three of which have walk-in closets and enjoy ensuite baths. One of the baths is designed to serve two bedrooms and the loft. The largest bedroom also includes a sitting area and an “office” area outfitted with high-speed internet access to support remote work. The multi-zoned, fully-carpeted finished basement offers another entirely separate gathering space complete with surround sound in the TV area, a pool table area, a game and party area and plenty of additional open space for the-sky’s-the-limit family entertainment possibilities. In addition, the basement contains three large storage rooms

27279 18th Blvd, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$625,000
4 Beds 4 Baths
An exceptional opportunity awaits as the seller holds a coveted Reserve Level Club Membership, allowing the next owner to enjoy immediate Reserve Level access without the typical wait. There are currently thirteen members on the wait list with an approximate ten-month wait. Nestled on a premium wooded homesite in The Conservancy at The Peninsula, this stunning residence is offered fully furnished, including all kitchen contents, making it truly move-in ready. Thoughtfully designed for both everyday comfort and elegant entertaining, the home features three bedrooms, two full baths, and one-half bath in the main residence, plus a private guest suite with its own bedroom and full bath. Recently refreshed with a professionally painted Hardi Plank exterior, the home showcases timeless curb appeal enhanced by a brick foundation and distinctive metal roof accents. Outdoor living is abundant, with two screened porches and two private balconies, several of which feature charming brick flooring and tranquil views of the surrounding natural landscape. Inside, the open-concept floor plan seamlessly blends style and functionality. The gourmet kitchen is appointed with rich oak cabinetry, granite countertops, a tile backsplash, under-cabinet lighting, a gas cooktop, and double wall ovens. The inviting living room centers around a gas fireplace and is framed by French doors that open to a screened brick porch overlooking serene woods and a picturesque pond. A versatile flex room on the main level provides the perfect space for a home office, library, or sitting room, with French doors leading to an additional brick patio. Completing the first floor is a spacious laundry and mudroom with direct access to the attached two-car garage. Upstairs, the luxurious primary suite serves as a private retreat, featuring its own screened porch, dual walk-in closets, and a spa-inspired bath with a double vanity, soaking tub, and separate tiled shower. A generous loft opens to a covered balcony, creating additional living and gathering space. Two guest bedrooms share a thoughtfully designed Jack-and-Jill bath with a separate shower and water closet. The private guest suite, accessed through its own exterior entrance, offers exceptional flexibility as a fourth bedroom, in-law suite, home office, or private retreat for visiting family and friends. Life at The Peninsula is unmatched. This private, gated community is home to a prestigious Jack Nicklaus Signature Golf Course and offers an extraordinary collection of resort-style amenities complemented by 24-hour staffed security. Residents enjoy a spectacular 32,000-square-foot clubhouse featuring fine and casual dining, a bar, golf lounges, a pro shop, a billiards room, a wine tasting room, and elegant gathering spaces. Additional amenities include five pools, a full-service spa, state-of-the-art fitness and training facilities, tennis and pickleball courts, basketball courts, miniature golf, walking and nature trails, fishing piers, a private sandy bay beach, kayak launch, nature center pavilion, observatory boardwalks, and year-round social activities. The HOA further enhances the carefree lifestyle by providing Verizon Fios high-speed internet and HD cable, complete lawn maintenance, snow removal, and refuse collection. This is a rare opportunity to own a beautifully furnished home in one of coastal Delaware’s most sought-after resort communities while enjoying immediate access to Reserve Level membership privileges.

22094 S Preservation Dr, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$429,900
3 Beds 3 Baths
Welcome to Windswept at The Peninsula - Experience resort-style living in this beautifully maintained, turnkey ground-floor condo located in the sought-after Windswept neighborhood of The Peninsula. Perfectly positioned just a short stroll from the community's world-class amenities, you'll enjoy convenient access to the clubhouse, indoor and outdoor pools, spa, fitness center, tennis courts, pickleball courts, and more. Offering 3 spacious bedrooms and 3 full bathrooms, this thoughtfully designed home combines comfort, functionality, and style. Luxury vinyl plank flooring flows throughout the main living areas, creating a warm and inviting atmosphere. The oversized owner's suite serves as a private retreat, featuring a spa-inspired ensuite bath with a soaking tub, walk-in shower, and dual vanities. The well-equipped kitchen boasts stainless steel appliances, abundant cabinetry, and generous counter space, making meal preparation and entertaining effortless. The open-concept dining and living areas provide the perfect gathering space for family and friends. Step outside to the screened porch and take in tranquil views overlooking the fairway of the community's premier golf course. Whether enjoying your morning coffee or unwinding with an evening beverage, this outdoor living space offers a peaceful setting to relax and recharge. An exceptional bonus for prospective buyers is the opportunity to receive first right of refusal for the seller's Reserve Membership position. This allows the purchaser to bypass the current waitlist and immediately pursue Reserve Membership, subject to club approval and membership purchase requirements. Beyond its appeal as a primary residence or vacation getaway, this property has a proven track record as a successful rental investment. Guests consistently praise its quiet location, comfortable accommodations, and easy access to both community amenities and the many attractions of the surrounding area. Rental history and income information are available upon request. The unit is being sold 'Fully Furnished' minus a few owner exceptions. If you've been searching for a home that offers luxury, convenience, and an unmatched coastal lifestyle, this Windswept condo delivers. Come discover why so many homeowners choose The Peninsula as one of the premier destinations in Sussex County. Schedule your private tour today and experience The Peninsula lifestyle for yourself.

33559 Windswept Dr Unit #11102, Millsboro

Listing courtesy of 360 PROPERTY SOLUTIONS. Contact: (302) 947-2800

$490,000
3 Beds 3 Baths
NEW PRICE!! Welcome to 33571 Windswept Drive #9302, a beautifully appointed third-floor condominium in The Peninsula, offering 3 bedrooms, 3 full bathrooms, and spectacular views of the 6th hole fairway, tranquil ponds, and the Indian River Bay beyond. This spacious residence combines comfort, convenience, and coastal elegance within one of Delaware's premier gated resort communities. Step inside to discover a bright, open-concept floor plan filled with natural light. The inviting main living area features custom built-ins, recessed lighting, and a cozy fireplace, creating a warm and welcoming space for everyday living and entertaining. The well-appointed kitchen showcases updated quartz countertops, an elegant glass tile backsplash, stainless steel appliances, abundant cabinetry, breakfast bar seating, and seamless flow into the dining and living areas. The spacious primary suite serves as a private retreat, complete with a luxurious ensuite bath featuring a soaking tub, separate shower, dual vanity, and generous storage, including two customized closets. Two additional bedrooms and full bathrooms provide comfortable accommodations for family and guests or flexibility for a home office. One of the home's standout features is the screened porch, where a private setting and panoramic views stretch across the manicured 6th fairway, sparkling pond, mature trees, and the Indian River Bay in the distance. Whether enjoying your morning coffee, watching golfers pass by, or taking in a colorful sunset over the water, this outdoor living space offers a truly memorable backdrop. This unit has a garage storage area that has been enhanced with modular organizational systems and specialty flooring, providing ample space for bicycles, beach gear, golf clubs, and seasonal items. Residents of The Peninsula enjoy an unparalleled resort lifestyle with amenities including a championship golf course, indoor and outdoor pools, wave pool, fitness center, spa, pickleball courts, walking trails, private bay beach, fishing pier, and kayak launch. The impressive 32,000-square-foot clubhouse features waterfront dining, gathering spaces, and year-round social activities. HOA services include Verizon Fios internet, HD television, and exterior maintenance, allowing for a truly low-maintenance coastal lifestyle. Whether you're seeking a primary residence, vacation home, or weekend retreat, this golf and water-view condominium presents a rare opportunity to enjoy resort-style living surrounded by natural beauty, championship golf, and the scenic waters of the Indian River Bay.

33571 Windswept Dr Unit #9302, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$1,325,000
3 Beds 4 Baths
Enjoy commanding views of the pond, 17th fairway, and Lingo Creek from this exceptionally maintained home in The Peninsula on the Indian River Bay. Designed to capture the beauty of its spectacular setting, the open floor plan features soaring ceilings in the living room, rich hardwood flooring throughout the main level, and a stunning stone hearth gas fireplace that creates a warm and inviting gathering space. The upgraded gourmet kitchen is a chef's dream, highlighted by Monogram appliances, a true six burner gas range, abundant cabinetry, and generous workspace for entertaining family and friends. Step onto the expansive deck off the main living area where breathtaking views provide the backdrop for outdoor living. A covered porch with its own fireplace, built in grill, and separate dining area creates the perfect setting for relaxing or hosting guests year-round. The primary suite serves as a private retreat, offering tranquil views, a spacious spa inspired bath, and convenient access to the oversized laundry room. Upstairs, a beautiful office or sitting room with a large walk-in closet provides exceptional flexibility and can easily serve as a 4th bedroom. The walkout lower level expands the living space with two additional bedrooms, two full baths, and a spacious family room ready to become the ultimate entertainment area. Outside, a second expansive outdoor living space invites you to fully embrace the waterfront and golf course views. A rare three car garage plus an additional workshop provides outstanding storage, hobby space, and flexibility rarely found in The Peninsula. Meticulously cared for and thoughtfully maintained, this home reflects pride of ownership throughout. The Peninsula offers a resort lifestyle with a Jack Nicklaus Signature Golf Course, clubhouse with indoor and outdoor dining, fitness center, indoor pool, outdoor adult pool, wave pool, tennis, pickleball, bocce, walking trails, nature center, fishing pier, bay beach, dog park, and more. Membership is required with multiple membership options available. Experience one of coastal Delaware's premier gated waterfront golf course communities.

33292 Marina Bay Cir, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$412,500
3 Beds 2 Baths
Welcome to Windswept Condominiums in The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches This fully furnished and generously sized three-bedroom residence offers an exceptional setting overlooking the first fairway of the renowned Jack Nicklaus Signature Golf Course. Located on the desirable top floor in this elevator building. Enjoy captivating sunrise views that set the tone for peaceful mornings and relaxing days. Ideally positioned just steps from the Clubhouse, this home provides effortless access to world-class amenities, dining, and social activities, making it equally well suited for full-time living or a coastal retreat. The thoughtfully designed floor plan feels bright, open, and inviting, enhanced by 9-foot ceilings throughout and a desirable southeastern exposure that fills the home with natural light. The main living areas feature engineered hardwood flooring for a cohesive and modern look, while the bedrooms are comfortably carpeted and the kitchen, foyer, laundry room and baths are finished with durable ceramic tile. The well-appointed kitchen is designed with both functionality and style in mind and will delight those who enjoy cooking. It features stainless steel appliances with gas five-burner stove, microwave, ample counter space, and a smart layout that simplifies meal preparation and cleanup. Dishwasher and refrigerator with icemaker are included. A convenient breakfast bar is perfect for casual dining or entertaining, while the adjacent dining area offers space for more formal meals. The dining area features wall sconce lights and chair rail molding. The open concept living and dining areas are anchored by a gas fireplace. It is flanked by two beautiful built-in bookcases and storage cabinets creating an ideal setting for gatherings or quiet evenings at home. Recessed lights and surround sound system complete the screening mode. Off the living room is a large sunroom and off the third bedroom is a screened porch with sweeping pond and golf course views with refreshing bay breezes. The primary bedroom also enjoys stunning views and features, and space for a sitting area or desk. There is a huge walk-in closet. The ensuite bath includes a double-sink granite-top vanity, a jetted tub, and a separate tiled walk-in shower —designed to provide comfort, privacy, and convenience. One of the guest bedrooms offers access to a private bath. A separate laundry room includes a washer and dryer. The adjacent utility closet hides the hot water heater and HVAC. Enjoy the convenience of the large storage room in the main-level parking garage and your assigned parking space. There is plenty of open parking in the parking lots in the Windswept neighborhood. The HOA and condominium fees cover an impressive array of services, including Verizon FIOS Internet and TV, common area, road maintenance, trash collection, 24/7 security, and contributions to long-term reserves for future capital improvements. Residents of The Peninsula enjoy access to an unparalleled lifestyle, with club membership required and membership levels available to suit the buyer’s preferences. From championship golf and indoor and outdoor pools to fitness facilities, dining, and a vibrant social calendar, The Peninsula offers an exceptional coastal living experience. Please inquire for additional details regarding club membership and community amenities.

33580 Windswept Dr Unit #4307, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$620,000
4 Beds 4 Baths
The lowest-priced detached home in The Peninsula! Motivated Seller. This desirable "South Beach" style home in coastal Delaware's premier beach/golf community offers four bedrooms and 3-1/2 baths to give you plenty of space for family and friends. This property would make a great primary, second home, or rental investment. Most of the furnishings are available as a separate bill of sale. New stainless steel kitchen appliances, including double wall ovens, a five-burner cooktop, microwave, and dishwasher. New white backsplash subway tile accents the many Maple cabinets. A new tankless Rannia hot water heater, a new washer, and a new dryer. Recently painted exterior white soffits and trim. This wonderful open design is perfect for entertaining. The gas fireplace anchors the living room and is flanked by two built-in bookcases. With many windows, the first level is flooded with light. The flex room can be used as a home office, formal dining room, and second family room. Step outside and enjoy the wraparound front porch with a screened-in section. This sets the stage for socializing with neighbors, while the backyard patio and two upper porches provide more private outdoor living areas. The primary bedroom suite is extremely spacious with a high tray ceiling, access to a private screened porch that beckons you to relax with your morning coffee and newspaper, two large walk-in closets, and a super-sized luxury bath. Three nice-sized additional bedrooms on the second floor, along with two additional baths. Your 2-car garage is neatly tucked into the rear of the home, so you'll benefit from maximum curb appeal in the front. Enjoy the comfort and savings of dual-fuel HVAC systems on the first level and a heat pump on the 2nd floor. The interior access to the concrete crawl space provides ample storage. The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches. The HOA and condominium fees cover an impressive array of services, including Verizon FIOS Internet and TV, common area, road maintenance, trash collection, 24/7 security, and contributions to long-term reserves for future capital improvements. Residents of The Peninsula enjoy access to an unparalleled lifestyle, with club membership required and membership levels available to suit the buyer’s preferences. From championship golf and indoor and outdoor pools to fitness facilities, dining, and a vibrant social calendar, The Peninsula offers an exceptional coastal living experience. Please inquire for additional details regarding club membership and community amenities. The clubhouse features a large restaurant with indoor and outdoor dining, a billiard room, a wine room, golf lounges, a pro shop, putting greens, a driving range, and a bocce court. The adjacent Lakeside Village features a fitness center, game room, full spa, cardio room, indoor pool, and hot tub, two outdoor pools (one adult-only), hot tub, and a sandy beach wave pool, miniature golf course, poolside restaurant, tennis, pickleball, basketball, and dog park. Relax on the private bay beach. Just 13 miles to historic Lewes and Rehoboth Beach boardwalk. Delaware boasts low property taxes and no sales tax. Enjoy the mild Mid-Atlantic climate today!

27447 S Nicklaus Ave, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$539,000
4 Beds 4 Baths
Tucked within the sought-after community of The Peninsula, this beautifully maintained end-unit townhome offers the perfect blend of luxury, comfort, and resort-style living. Built in 2020, this spacious 4-bedroom home is filled with natural light and showcases peaceful pond views from many of the main living areas. The open-concept design creates an easy flow for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring granite countertops, a large center island, stainless steel appliances, an Electrolux gas cooktop, and a wall oven. The adjoining dining and living areas open seamlessly together, creating a bright and inviting space with expansive water views. The first-floor primary suite offers a relaxing retreat with a tray ceiling, walk-in closet, spa-inspired custom tile shower, and tranquil pond views. Also located on the main level are the laundry room, pantry, updated powder room, and attached one-car garage for added convenience. Upstairs, you’ll find three additional bedrooms, including a private en suite, another full bath, and a versatile loft area perfect for a second living room, office, or guest space. Life at The Peninsula is all about the amenities. This gated waterfront community, home to a Jack Nicklaus Signature golf course, offers an unmatched coastal lifestyle along the Indian River Bay. Residents enjoy access to indoor and outdoor dining, a clubhouse, fitness center, spa, indoor pool, multiple outdoor pools, including an adults-only heated pool and wave pool, tennis and pickleball courts, miniature golf, bocce, walking trails, dog park, private bay beach, putting greens, driving range, and more. Short-term rentals are permitted, making this property an excellent full-time residence, vacation home, or investment opportunity. Ideally located just a short drive from both downtown Lewes and the Rehoboth Beach boardwalk, this home also benefits from Delaware’s low property taxes and tax-free shopping. Community Fees and Dues:Fees: *Capitol Contribution for all sales: ½ of 1% of the purchase price goes to the PCA (.005). *Annual Food Minimum $800.00 2026 Homeowner Association and Redus Fees. : $1033.00.- Billed Quarterly. This fee includes the following: Security, Maintenance of the Nature and Exploration Center, Bay Beach Fishing Pier, Trails, Roads, Snow Removal, Lights, Lawn and Landscaping Care, Trash Collection, Verizon Optics, Verizon Fios Extreme Television Programming, and much more. *2026 Condo Association Fees- $1,431. Billed Annually. Capital Fee of $750. * 2026 Membership Initiation, Deposit, and Dues: Reserve- $70,000. Monthly: $775. Sports-$35,000. Monthly $457. or Social-$20,000. Monthly $386. Square Footage- The tax parcel pulled 2,456 square feet, but the old listing showed 2,195. Square footage to be confirmed for accuracy.

24236 Canoe Drive Unit #225, Millsboro

Listing courtesy of EXP Realty, LLC. Contact: 8885434829

$1,400,000
4 Beds 4 Baths
Welcome to 27535 Medallion Ave. and experience elevated coastal luxury in this exceptional expanded Bethany model by Schell Brothers. Perfectly nestled within the highly sought after Lakeside community of the Peninsula on Indian River Bay, this premium golf course homesite provides a protected green park setting in front and a 180° Lakeside view behind where you can lounge, birdwatch and take in all that nature has to offer. This remarkable residence offers a rare opportunity to own within one of the community's most desirable enclaves, where no additional Lakeside lots remain. Thoughtfully designed and impeccably maintained with 3625 square feet of luxurious living space, this 4-bedroom 3.5 bath home offers timeless coastal elegance with extensive builder and custom upgrades throughout. From the moment you arrive the home greets you with a lasting impression with custom cement siding, upgraded architectural details, custom pillars, manicured landscaping and expanded garage designed for both convenience and storage. Inside, engineered hardwood floors flow seamlessly throughout the main and second floor living spaces complemented by wainscoting, custom trim, designer lighting, window treatments and upgraded finishes that create an atmosphere of understated sophistication. The expansive open concept floor plan is filled with natural light and designed for everyday comfort and effortless entertaining. At the heart of the home, the gourmet kitchen showcases 42" upgraded cabinetry and premium Bosch appliances including a 5-burner gas cooktop, double wall ovens, built in microwave, and refrigerator with icemaker. Generous granite countertops provide ample prep and gathering space, ideal for hosting family and friends. The adjoining dining and living areas seamlessly connect to the outdoor living spaces framing serene lake views that serve as the perfect environment to daily living. Designed with flexibility and comfort in mind, the home features both first and second floor primary suites, making it ideal for multigenerational living or hosting guests while offering complete privacy. The main level primary suite is an elegant retreat featuring an extended 4' sitting area, elegant tray ceiling with custom trim, and a beautifully appointed spa inspired bath. The primary bath offers wide format porcelain tile flooring, a freestanding clawfoot cast-iron soaking tub, and upgraded Kohler fixtures and finishes. Upstairs, 2 additional bedrooms, a spacious loft, and second primary suite provide exceptional versatility for relaxation, recreation, and guest accommodations. Aviation ceiling fans with carefully selected upgrades further elevate, both style and functionality. Outdoor living is equally impressive highlighted by a 36‘x20‘ paver stone patio overlooking the tranquil lake and the 11th tee of the Jack Nicklaus signature golf course, creating the perfect setting for entertainment or relaxing and simply enjoying the beauty of nature. The property has also been thoughtfully upgraded electrically to accommodate the future installation of a 16‘x36‘ inground swimming pool and hot tub offering endless possibilities for creating a private outdoor oasis. A Generac whole house generator provides additional peace of mind and year-round comfort. Located within the gated amenity rich Peninsula community, residents enjoy access to a Jack Nicklaus signature golf course, indoor and outdoor pools(including a wave pool with a sandy beach and an adult only pool), fitness center, spa, bocce, tennis and pickleball courts, walking trails, fishing piers, private Bay beach, water sports, clubhouse, and poolside dining - a truly unmatched coastal lifestyle. Conveniently located just a short drive to historic Lewes, Rehoboth, and Delaware and Ocean City beaches. Combining the premium location, breathtaking views, classic upgrades, and rarity of Lakeside living, this home offers a unique opportunity to enjoy resort style living at its finest!

27535 Medallion Ave, Millsboro

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777

$555,000
4 Beds 4 Baths
Experience resort-style living in this beautifully designed end-unit townhome in The Peninsula. This home offers 4 bedrooms, 3.5 baths, a versatile loft, and a finished, painted 1-car garage, with convenient first-floor living and an abundance of natural light throughout. Step inside to a welcoming dining area that flows seamlessly into the gourmet kitchen, complete with quartz countertops, tile backsplash, double wall ovens, and LVP flooring. The spacious living room impresses with a vaulted ceiling and sliding doors leading to the screened porch, perfect for relaxing or entertaining outdoors. The primary suite is tucked away on the main level and features a tray ceiling, walk-in closet, and beautifully appointed bath. Upstairs, you’ll find three additional bedrooms and a versatile loft space, giving guests and family plenty of room to spread out. Outside, the home is enhanced with landscaping lights, adding beautiful curb appeal and a warm evening glow. Located in one of Delaware’s premier gated resort style communities, The Peninsula offers unmatched amenities including a Jack Nicklaus Signature golf course, indoor and outdoor pools, tennis and pickleball courts, fitness center, dining, walking trails, and more. Schedule your private tour today and start enjoying the coastal lifestyle you’ve been looking for.

27236 18th Blvd, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$695,000
3 Beds 3 Baths
Welcome to refined coastal living in The Peninsula - one of Delaware’s most coveted resort-style communities - where your lifestyle can be as vibrant or as peaceful as you choose. Perfectly positioned within the sought-after Veranda neighborhood, 33187 Veranda Circle offers an ideal age-in-place floor plan designed for comfort, ease, and elegant everyday living. From the moment you arrive, this beautifully appointed home invites you to relax and entertain with effortless style. A light-filled, open-concept floorplan seamlessly connects the gourmet kitchen, spacious living area with a floor-to-ceiling stacked-stone fireplace and inviting dining area and screened porch - creating the perfect backdrop for gatherings or quiet evenings at home. The main-level owner’s suite provides a private retreat with a spa-inspired bath, while a dedicated home office adds flexibility for today’s lifestyle. Upstairs, guests will appreciate their own space with additional bedrooms (one with a private balcony) and a versatile loft for leisure and relaxation. Beyond your doorstep, The Peninsula delivers an unparalleled resort experience set along the Indian River Bay. Enjoy access to a Jack Nicklaus Signature golf course, a stunning clubhouse with dining and social spaces, indoor and outdoor pool - including a wave pool, fitness and spa facilities, tennis and pickleball courts, scenic walking trails, and a private bay beach. Every day feels like a getaway, with world-class amenities and natural beauty surrounding you. Just a short drive brings you to the charming coastal towns and award-winning beaches of Lewes, Rehoboth, and Dewey - offering the perfect blend of seaside adventure and small-town charm. Then return home to the tranquility, security, and luxury that only The Peninsula provides. Offered at $695,000, this is more than a home, it’s a lifestyle. Experience it for yourself and discover why so many are proud to call The Peninsula home.

33187 Veranda Cir, Millsboro

Listing courtesy of Coldwell Banker Premier - Rehoboth. Contact: (302) 227-5000

$775,000
3 Beds 2 Baths
Located on a premium corner lot in The Peninsula, backing to a stocked bass catch-and-release pond and miles of scenic walking trails, this beautifully updated RANCH model offers an exceptional coastal lifestyle within one of the area’s most sought-after resort communities. Built by Insight Homes, known for their commitment to superior energy efficiency and high-performance construction, this residence is designed for both comfort and cost savings, featuring advanced building techniques that promote healthier indoor air quality and reduced utility expenses. The private cul-de-sac location offers added parking flexibility. This is single level living at its finest. An embellished stone exterior and extended footprint, including an additional four feet of living space, create a striking first impression. Inside, the inviting foyer opens with updated luxury plank flooring, deep crown molding, custom paint throughout, and Hunter Douglas plantation shutters. Just off the foyer, a newly enclosed front room provides a flexible space ideal for a home office or additional sleeping quarters. The remodeled kitchen is a true standout, featuring gorgeous quartz countertops with light veining, a stylish coastal backsplash, crisp white soft-close cabinetry with crown molding, display cabinets, and both under-cabinet and accent lighting. A gas cooktop, double wall ovens, pantry, and an island with beadboard accents and a breakfast bar for additional seating complete this thoughtfully designed space. The adjacent dining room and open flow into the living area make it ideal for both everyday living and entertaining. The living room is warm and welcoming, highlighted by a floor-to-ceiling ledgestone gas fireplace with a raised hearth, vaulted ceilings, and high-end ceiling fans. A light-filled sunroom with expansive windows with motorized blinds and glass sliding doors bring the outdoors in, creating the perfect place to relax year-round. Step outside to the expansive New composite deck, thoughtfully designed with multiple zones for lounging and dining. During the cooler months, enjoy peaceful views of the pond beyond, where mornings can begin with coffee and the calming reflection of sunlight on the water. The primary suite offers a private retreat with a sitting room behind French doors, a spacious walk-in closet, and a well-appointed bath featuring a dual sink vanity, cultured marble countertops, and an updated custom tiled frameless shower with built-in seating and dual shower heads. Two additional bedrooms, a hall bath, and a laundry room with direct garage access complete the home’s convenient single-level layout. The customized garage is equally impressive, featuring an epoxy floor, painted walls, built-in storage, a Navien tankless water heater, Cyclo central vacuum system, and a Fosom dual laser parking assist. In addition, a seller add-on includes a walk-up to a floored attic space measuring approximately 22 x 16 providing excellent storage options. Further enhancements include a two-foot garage extension and an encapsulated crawl space. Residents of The Peninsula enjoy an unmatched array of amenities, including gated security, a clubhouse, Jack Nicklaus Signature Golf Course and driving range, fitness center with indoor, outdoor, and wave pools, hot tubs, sauna, spa services, tennis and pickleball courts, dog park, community garden, nature center, private bay beach, fishing pier, and miles of walking and biking trails. Set amid 800 acres along the Indian River Bay, The Peninsula is renowned for its breathtaking natural surroundings, where Lingo Creek winds through the community and tidal wetlands stretch toward the bay, offering stunning sunrise views. This is an exceptional opportunity to enjoy refined coastal living in a thoughtfully upgraded home within a truly spectacular setting.

33241 Indian Bay Cir Unit #35, Millsboro

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$670,000
4 Beds 4 Baths
Welcome to the Veranda neighborhood within The Peninsula on the Indian River Bay, a premier, amenity-rich coastal community cultivated by refined living and natural beauty. Residents enjoy access to resort-style amenities, including a Jack Nicklaus Signature Golf Course, private bay beach, scenic walking trails, and preserved wetlands, all set across more than 800 acres of meticulously maintained grounds. This exceptional Catalina model, offering over 3,400 heated square feet, is ideally positioned on a picturesque garden circle, highlighted by a welcoming and expansive front courtyard with tranquil views. Thoughtfully designed across three levels, this home provides both comfort and versatility for everyday living and hosting guests. Outdoor living is equally inviting, featuring a spacious screened front porch overlooking lush gardens, as well as a newly installed, private, landscaped paver patio in the rear, perfect for relaxing or entertaining. Inside, the open-concept layout is enhanced by 9-foot ceilings, recessed lighting, and elegant double crown molding throughout the main level. The gourmet kitchen is designed to impress, featuring 42-inch cabinetry, new stainless steel appliances, upgraded granite countertops, double wall ovens, a gas cooktop, and an oversized breakfast bar with ample prep space. The adjacent dining area comfortably accommodates large gatherings, while three sets of French doors seamlessly connect the interior to the screened porch. The main level also offers a flexible floor plan, including a formal living room with a gas fireplace and custom built-ins, a study (or optional fifth bedroom), and an additional room that can serve as a family room or formal dining space. A powder room and mudroom provide convenient access to the attached two-car garage. In addition to the garage, the property includes two deeded parking spaces, offering a total of six parking spots. Upstairs, the spacious primary suite features 9-foot ceilings, recessed lighting, a ceiling fan, and an exceptionally large walk-in closet. The luxurious en-suite bath includes a double vanity, soaking tub, and a generously sized tiled shower with seating. Two additional guest bedrooms share a full bath, complemented by a loft area and a full laundry room with utility sink. The third level serves as a versatile retreat, complete with a full bath and closet, ideal as a fourth bedroom, guest suite, or expansive bonus/game room. Recent upgrades add significant value and peace of mind, including a new HVAC system (with added dehumidifier), new hot water heater, updated flooring throughout much of the home, new toilets, blinds, ceiling fans, refreshed interior paint, and enhanced landscaping. A standout feature is the conditioned crawl space with interior access, offering substantial storage with a finished concrete floor. The exterior showcases durable HardiePlank siding with attractive metal roof accents, further enhancing curb appeal. Whether a primary residence, second home, or investment property, this home offers excellent rental potential. Ideally located just a short drive from Lewes, the Cape May-Lewes Ferry, Cape Henlopen State Park, Rehoboth Beach, and Dewey Beach, this property offers convenient access to the very best of coastal Delaware. Added benefits include Delaware’s lack of sales tax and relatively low property taxes, making this an even more compelling opportunity.

33139 Serenity Cir Unit #84, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$1,750,000
4 Beds 5 Baths
Welcome to 27271 18th Boulevard, a remarkable coastal retreat set along the 17th fairway of the acclaimed Jack Nicklaus Signature Golf Course, within the prestigious The Peninsula on the Indian River Bay. Built by Schell Brothers and thoughtfully curated at every turn, this exceptional residence offers three levels of refined living, seamlessly connected by a private elevator for ultimate ease and comfort. From the moment you arrive, the home makes a lasting impression. A welcoming foyer introduces a setting defined by craftsmanship and detail, where wide-plank, 7-inch hand-scraped hickory flooring carries throughout, complemented by custom millwork, upgraded trim, crown molding, plantation shutters, designer window treatments, and remote-controlled shades. Multiple balconies and outdoor living spaces capture sweeping views of the fairway, Lingo Creek leading to Indian River Bay and surrounding wetlands, creating a constant connection to the natural beauty beyond. The gourmet kitchen serves as the centerpiece of the home, both visually stunning and highly functional. Outfitted with GE Café Professional appliances, including a five-burner gas cooktop and statement range hood, the space is anchored by an expansive island with pendant lighting. Granite countertops, a timeless subway tile backsplash, soft-close cabinetry with under-cabinet lighting, display accents, and pull-out drawers offer both elegance and efficiency. A beautifully designed butler’s pantry, complete with a full-size refrigerator and distinctive fluted cabinetry, adds an additional layer of style and convenience. The open-concept design flows effortlessly into the dining and living areas, where a gas fireplace with a stone surround creates a warm and inviting focal point. Transom-topped sliding glass doors lead to a covered porch and elevated deck, offering a front-row seat to the manicured fairway, Lingo Creek and the tranquil landscape beyond. The main-level primary suite is a peaceful retreat with a private balcony, a spa-like bath featuring a quartz vanity, a fully tiled walk-in shower with transom window, and a spacious walk-in closet. Upstairs, a gracefully turned staircase leads to a second primary suite with a tray ceiling, crown molding, expansive windows, two walk-in closets, and a private balcony. The ensuite bath features dual quartz vanities and an oversized glass-enclosed shower. Two additional guest bedrooms, a well-appointed hall bath, and a convenient laundry room with cabinetry and utility sink complete the upper level. The lower level continues to impress with a generous 33 x 21 recreation room, offering exceptional flexibility for entertaining, media, or additional living space with a half bath. You will have direct access to a beautifully tiled patio extending the living area outdoors, creating a polished and inviting setting for gatherings or quiet relaxation. Everyday functionality has been elevated with thoughtful enhancements, including a professionally finished garage featuring epoxy flooring and custom storage systems, a discreet trash enclosure, additional storage in elevator mech. room and under the front steps, upgraded landscaping supported by an irrigation system, a home security system, and an invisible fence. Life at The Peninsula is defined by its extraordinary setting and amenities. Spanning 800 acres along the Indian River Bay, residents enjoy a private world of resort-style living, including championship golf, clubhouse dining, golf lounges, a pro shop, full-service spa, state-of-the-art fitness center, indoor and outdoor pools, including an adult-only heated pool and wave pool with sandy beach, tennis and pickleball courts, scenic walking trails, a dog park, and a private bay beach. Ideally located just a short drive from Lewes, Delaware and the Rehoboth Beach Boardwalk. This home is a sophisticated coastal escape where thoughtful design, elevated finishes, and an unmatched lifestyle comes together beautifully.

27271 18th Blvd, Millsboro

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$905,000
4 Beds 4 Baths
Classic coastal elegance defines this Hampton floor plan, showcasing a stately front staircase and timeless center hall design that creates both presence and flow. Thoughtfully designed across three levels, the home offers multiple porches at the front and rear, inviting you to enjoy outdoor living from every vantage point. A welcoming sidewalk leads from the driveway to the backyard, where exterior steps connect the upper porch to a lower level porch and patio, creating seamless access for entertaining and everyday enjoyment. The main level is beautifully arranged with a center hall layout, offering a variety of spaces including a living and dining room , private study, family room, spacious kitchen, sitting room, and access to a relaxing porch. The design balances openness with defined spaces, ideal for both gathering and quiet retreat. With four bedrooms and three and a half baths, the home provides exceptional flexibility. The primary suite is located on the upper level along with a second ensuite bedroom, perfect for guests or multi generational living. The lower level features two additional bedrooms with a shared bath, each with direct access to a covered porch, creating a private and comfortable guest space. The garage has been reimagined as a vibrant game and entertainment area, complete with billiards, shuffleboard, and a comfortable seating area for movie nights, offering a fun and unexpected extension of the home’s living space. FURNITURE is Negotiable via separate agreement. Updates include a tankless water heater and replaced HVAC systems in 2018 and 2025, adding comfort and efficiency. This home delivers a refined yet relaxed lifestyle with thoughtful design, generous space, and inviting indoor and outdoor living areas throughout. Relax and enjoy a low maintenance lifestyle with yard care provided by the HOA. Step outside and experience the Peninsula community, offering world class amenities within a secure gated setting. The clubhouse is the social heart of the community, featuring a full service restaurant with indoor and outdoor dining, billiards, wine and game rooms, men’s and women’s lounges, a pro shop, putting greens, driving range, bocce courts, and the renowned Jack Nicklaus golf course. Just beyond, Lakeside Village offers an exceptional wellness and recreation experience with a state of the art fitness center, indoor pool, adult outdoor pool, wave pool, and activity pool. Enjoy poolside dining throughout the summer, the popular Tiki bar, fitness classes, weight room, hot tubs, sauna, spa spaces, and a game room. Outdoor amenities continue with tennis, pickleball, a dog park, community garden, nature center, bay beach, fishing pier, and miles of scenic walking trails. A vibrant social calendar of year round events creates endless opportunities to connect and build lasting friendships. A capital contribution to the PCA of 0.5% of the sales price applies. Club membership is required with three available levels. Please see disclosures for full details.

27606 S Nicklaus Ave, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$875,000
5 Beds 5 Baths
Perfectly positioned along the 2nd fairway, this exceptional three level coastal retreat captures sweeping views of both the golf course and a tranquil pond, a picturesque backdrop you will truly never tire of. Designed to embrace its surroundings, the home offers multiple porches across two levels, inviting you to relax, entertain, and take in the ever changing scenery from sunrise to sunset. With five bedrooms (two with ensuite baths) and four and a half baths, the layout provides generous space for both everyday living and hosting guests. Light filled interiors and thoughtfully designed gathering areas create a seamless flow, while the outdoor living spaces extend the experience, offering peaceful moments and vibrant entertaining alike. Recent upgrades add comfort and efficiency, including a tankless water heater and new (2021 & 2025) two zone HVAC system. Relax and enjoy a low maintenance lifestyle with yard care provided by the HOA. Step outside and experience the Peninsula community, offering world class amenities within a secure gated setting. The clubhouse is the social heart of the community, featuring a full service restaurant with indoor and outdoor dining, billiards, wine and game rooms, men’s and women’s lounges, a pro shop, putting greens, driving range, bocce courts, and the renowned Jack Nicklaus golf course. Just beyond, Lakeside Village offers an exceptional wellness and recreation experience with a state of the art fitness center, indoor pool, adult outdoor pool, wave pool, and activity pool. Enjoy poolside dining throughout the summer, the popular Tiki bar, fitness classes, weight room, hot tubs, sauna, spa spaces, and a game room. Outdoor amenities continue with tennis, pickleball, a dog park, community garden, nature center, bay beach, fishing pier, and miles of scenic walking trails. A vibrant social calendar of year round events creates endless opportunities to connect and build lasting friendships. A capital contribution to the PCA of 0.5% of the sales price applies. Club membership is required with three available levels. Please see disclosures for full details.

27604 S Nicklaus Ave, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$315,000
2 Beds 2 Baths
Fully furnished - Turnkey. Welcome to Windswept Condominiums in The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches. Ideally positioned just steps from the Clubhouse, this home provides effortless access to world-class amenities, dining, and social activities, making it equally well-suited for full-time living or a coastal retreat. The thoughtfully designed floor plan feels bright, open, and inviting, enhanced by 9-foot ceilings throughout. The main living areas feature engineered hardwood flooring for a cohesive and modern look, while the bedrooms are comfortably carpeted, and the kitchen, foyer, laundry room, and baths are finished with durable ceramic tile. The well-appointed kitchen is designed with both functionality and style in mind and will delight those who enjoy cooking. It features black appliances with electric cooking, microwave, ample counter space, and a smart layout that simplifies meal preparation and cleanup. Dishwasher and refrigerator with icemaker are included. A convenient breakfast bar is perfect for casual dining or entertaining, while the adjacent dining area offers space for more formal meals. The open concept living and dining areas are anchored by a gas fireplace. It is flanked by beautiful Maple built-in bookcases and storage cabinets creating an ideal setting for gatherings or quiet evenings at home. From the living room, step outside onto your private screened balcony. The primary bedroom space for a sitting area or desk. There are two closets, including one walk-in. The ensuite bath includes a double-sink vanity, a soaking tub, separate shower, and toilet—designed to provide comfort, privacy, and convenience. The guest bedroom offers access to a private bath, a walk-in closet, and a ceiling fan. A separate laundry room includes a washer and dryer. The adjacent utility closet houses the hot water heater and HVAC system. An additional highlight is a new 2018 HVAC heat pump, adding peace of mind and energy efficiency. Enjoy the convenience of the large storage room in the main level parking garage and your assigned parking space. There is plenty of open parking in the Windswept neighborhood's parking lots. The HOA and condominium fees cover an impressive array of services, including Verizon FIOS Internet and TV, common area, road maintenance, trash collection, 24/7 security, and contributions to long-term reserves for future capital improvements. Residents of The Peninsula enjoy access to an unparalleled lifestyle, with club membership required and membership levels available to suit the buyer’s preferences. From championship golf and indoor and outdoor pools to fitness facilities, dining, and a vibrant social calendar, The Peninsula offers an exceptional coastal living experience. Please inquire for additional details regarding club membership and community amenities.

33580 Windswept Dr Unit #4202, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$359,000
3 Beds 2 Baths
SPECIAL INCENTIVE UNTIL END OF AUGUST: SELLER WILL ACCEPT $325,000 , AS IS . This top floor, corner unit condo is situated in the amenity-rich community of The Peninsula on the Indian River Bay. It has three bedrooms, two full baths, an open floor plan, 9-foot ceilings, built-in bookcases flanking a gas fireplace, LVP flooring throughout the living areas, carpeting in the bedrooms, tile in the kitchen and bathrooms plus a neutral color palette. The kitchen features a breakfast bar, granite countertops and stainless-steel appliances. A separate dining area flows into the sunroom bringing loads of light through the many windows that overlook the Windswept neighborhood. The primary suite with its woodland and golf-course views includes access to the screened-in balcony, a double sink vanity, tiled shower, and a relaxing soaking tub. Verizon cable and internet are included in the monthly fees. One covered garage parking space and a secure ground-level storage unit conveys. Club Membership is Mandatory, choose from 3 levels: Social, Sport or Reserve. This gated community offers, 24/7 Security Guard, Jack Nicklaus golf course, clubhouse, restaurant, indoor and outdoor pools, a wave pool, fitness center, hot tubs, sauna, spa, game room, basketball, tennis and pickleball courts, a dog park, nature center, bay beach, fishing pier, and miles of walking trails. In other words, low-maintenance luxury living plus a $1,000 credit to the Buyers to use as they wish. Motivated Seller!

33584 Windswept Dr Unit #5401, Millsboro

Listing courtesy of Jack Lingo - Rehoboth. Contact: (302) 227-3883

$860,000
5 Beds 5 Baths
Welcome to 27582 S. Nicklaus Ave., MOVE-IN READY with FRESHLY PAINTED EXTERIOR (July 2026) and a SPACIOUS, LOVINGLY REFRESHED INTERIOR. Located on a premium golf-course lot in The Peninsula, coastal Delaware's premier resort-style country club community! You'll have PANORAMIC TEE-TO-GREEN, SUNRISE-TO-SUNSET VIEWS of the 2nd fairway from all three levels of this upscale home! Plenty of space for everyone here, with an open-space concept floor plan, 10-foot ceiling height on the main level, 5 bedrooms, 4 full baths and one half baths. Morning sun illuminates the great room, featuring built-in bookcases flanking the gas fireplace, a breakfast area, and direct access to the covered main porch -- offering afternoon shade, perfect for entertaining. A large kitchen island adds to the dining space here, as well as adding to the already-abundant counter space for the chef. Countertops are granite, and upgraded cabinetry extends from the breakfast area through the kitchen and into the adjoining butler's pantry, which is equipped with a wet bar. It leads to the formal dining room, which could be repurposed as a study or game room if desired. The owner's suite occupies the entire rear of the 2nd floor, with stunning views from both the bedroom and bath, as well as direct access to its private covered porch - a sunny, private spot for morning coffee or an afternoon in the shade watching golfers, listening to the birds, or curled up with a good book. Down the hall there are three additional bedrooms (one with ensuite bath and two with a shared bath) and a conveniently-placed laundry room. The "bonus level" of this home adds a 5th bedroom, complete with ensuite bath. An attached side-entry 2-car garage completes the home. The Peninsula is a private, gated community with nine separate neighborhoods and a wide array of recreational facilities: a private Jack Nicklaus Signature golf course, elegant and casual dining in the 34,000 sq. ft. clubhouse, 3 outdoor pools including a heated adults-only pool, the area's only wave pool, a huge family activities pool, an outdoor splash zone for the smaller kids, and a heated indoor pool. You'll also have access to hot tubs, locker rooms with saunas, mini-golf, tennis and pickleball, a private bay beach, Nature Center with kayak launch, and more! Club membership is required, and the choice of membership level is yours -- please ask for details. Sellers will include a one-year home warranty with an acceptable offer.

27582 S Nicklaus Ave Unit #11, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$845,000
4 Beds 4 Baths
Privately situated in a quiet setting within the Conservancy neighborhood of the Peninsula, this Southern-inspired floor plan offers a beautiful blend of charm, comfort, and refined living. Designed to embrace its natural surroundings, the home features expansive porches on both levels, creating a seamless connection to the outdoors. Two of the side porches have been thoughtfully enclosed, offering inviting three-season spaces to relax and unwind. Inside, a light filled interior welcomes you with soaring cathedral ceilings and an open, airy layout. The spacious kitchen and casual dining area flow effortlessly into the main living space, creating the perfect setting for entertaining or everyday living. A separate dining room provides an elegant option for more formal gatherings. The first floor primary suite, complete with porch access, serves as a peaceful retreat, while a private den offers the ideal space for a home office or quiet escape. Upstairs, a second primary suite features an ensuite bath and direct porch access, creating a private haven for guests. Two additional bedrooms each open to a shared porch, giving every bedroom its own connection to the outdoors and enhancing the home’s distinctive design. A loft space provides a second family room space. Step outside to a cozy and beautifully designed paver patio, complete with a stone knee wall, generous seating, a gas fireplace, grill space and mature landscaping, perfect for year round enjoyment and relaxed evenings under the trees. Significant improvements include the 2021 replacement of two HVAC systems and a tankless water heater, offering comfort and efficiency for years to come and new carpet (2026) in the Primary bedroom From its distinctive Southern architecture to its versatile layout featuring two primary suites and exceptional privacy, this home presents a rare opportunity to enjoy relaxed luxury living in one of the Peninsula’s most sought-after neighborhoods. Enjoy a truly effortless lifestyle as lawn care is provided by the HOA allowing you to spend more time experiencing all that the Peninsula has to offer. This gated coastal golf and country club community features a stunning clubhouse with indoor and outdoor dining, billiards, wine and game rooms, lounges, pro shop, putting greens, driving range, bocce courts, and the Jack Nicklaus Signature golf course. The Lakeside Village offers a full fitness center with indoor pool, outdoor adult pool, wave pool, and activity pool, along with poolside dining and a lively Tiki bar. Additional amenities include fitness classes, hot tubs, sauna and spa rooms, tennis, pickleball, dog park, community garden, nature center, private bay beach, fishing pier, and miles of scenic walking trails. A vibrant calendar of year-round events makes it easy to connect and build lasting friendships. Capital contribution to PCA is 0.5% of the sales price. And $750. To the Conservancy Club membership is required, with three levels available—please see disclosures for details.

22163 Dune Cir, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$399,000
3 Beds 2 Baths
Welcome to 33580 Windswept, unit 4207, a beautifully appointed three-bedroom, two-bath condo in the sought-after Peninsula community. With an unbeatable location you will enjoy being close to the clubhouse, pools, golf course, tennis courts, bay, and more, this home places you at the center of an active, amenity-filled lifestyle while offering stylish, stress free, low-maintenance living. The living room is warm and welcoming highlighted by layered crown molding, elegant built-in cabinetry with display shelves, and a gas fireplace that anchor the space as a focal point. The gourmet kitchen boasts 42-inch craftsman-style cabinets with display accents, stainless steel appliances, granite countertops, a double sink, ample counter space, and a breakfast bar for casual dining. The adjoining dining area is accented with chair rail detailing, while the sunroom area and kitchen feature durable, low-maintenance ceramic tile flooring. The primary suite is a private retreat, complete with crown molding, a spacious double-door walk-in closet, and an atrium door leading to a private balcony with pond and golf course views. Its ensuite bathroom offers granite countertops, dual-sink vanity, a soaking tub, and a stall shower with bench seating. The second bedroom also opens to the balcony and is large enough for two beds, while the third bedroom has access to the hall bath. Enjoy the ease of an assigned parking space and building elevator, making coming and going simple and stress-free. Living in The Peninsula means access to an unparalleled array of resort-style amenities. Residents enjoy the Jack Nicklaus Signature Golf Course, The Terrace Grille for poolside dining and drinks, indoor and outdoor pools, a wave pool, a state-of-the-art fitness center, a full-service spa, tennis and pickleball courts, basketball courts, a private beach and pier, and a clubhouse featuring fine dining, billiards, and meeting rooms. Scenic nature trails along Lingo Creek provide the perfect setting for walking, jogging, or simply enjoying the outdoors. Whether you’re seeking a primary residence or a coastal retreat, this condo offers effortless luxury living in a community designed for recreation, relaxation, and connection. Schedule your viewing appointment today!

33580 Windswept Dr Unit #4207, Millsboro

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$789,900
5 Beds 5 Baths
Welcome to 3 Rycroft Rd, a charming and well-maintained home in a desirable and convenient location. This inviting property offers a wonderful blend of comfort, functionality, and style, making it an excellent opportunity for a wide range of buyers. Step inside to a bright and welcoming interior filled with natural light. The main living spaces are thoughtfully designed to provide both openness and versatility, creating an ideal setting for everyday living and entertaining. The kitchen features ample cabinetry and counter space, offering both practicality and efficiency for daily use. The home’s layout provides comfortable living areas and well-appointed spaces throughout. Outside, enjoy a pleasant yard with plenty of room for relaxing or outdoor gatherings. Conveniently located near shopping, dining, schools, and major commuter routes, this home combines peaceful living with easy access to everyday amenities. Don’t miss the opportunity to make this delightful property your own!

3 Rycroft Road, Mechanicsburg

Listing courtesy of Prime Realty Services. Contact: 7173052600

$875,000
4 Beds 3 Baths
Nicely Improved Price!! Beautifully positioned on a quiet cul-de-sac along the 14th fairway, this thoughtfully designed 4 bedroom, 3 full bath home captures sweeping westerly views and stunning sunsets across the course. Expansive windows along the rear of the home frame the scenic setting, filling the interior with natural light and providing picturesque views throughout the day. The main living spaces feature hardwood flooring and a dramatic two-story living room with a gas fireplace, creating an open and welcoming atmosphere. The layout offers exceptional flexibility with two bedrooms on the first floor, including an expanded primary suite including a sitting area, custom designed closet system, and a recently renovated spa-inspired bath designed for relaxation. The second main-level bedroom can easily function as a study or home office, ideal for today’s lifestyle. Outdoor living is just as inviting, with a beautifully designed large paver patio featuring a stone knee wall, offering the perfect place to relax, entertain, and enjoy peaceful golf course views and glowing evening sunsets. Upstairs, a loft style living area provides additional gathering space for guests or family, accompanied by two bedrooms and a full bath. An unfinished bonus room offers exciting possibilities—perfect for additional storage or ready to be transformed into another bedroom, office, fitness studio, hobby room, or private retreat. With its peaceful setting, versatile floor plan, and beautiful golf course views, this home offers a wonderful opportunity to enjoy the relaxed lifestyle and natural beauty of life in the Peninsula. Enjoy the Peninsula lifestyle, where coastal beauty meets exceptional amenities in a private, gated community on the Indian River Bay. The Jack Nicklaus Signature golf course, private bay beach, indoor and outdoor pools, full-service spa, state-of-the-art fitness center, tennis and pickleball courts, miles of scenic nature trails, and a vibrant clubhouse with dining and year-round social activities. Life at the Peninsula offers the perfect balance of relaxation, recreation, and community along Delaware’s beautiful coast. Club membership is required, choose from 3 levels, see disclosures.

24565 Atlantic Dr, Millsboro

Listing courtesy of Compass. Contact: 3022734998

$735,000
3 Beds 2 Baths
Skip the line! Beat the two-year waitlist for golf. This property offers a Reserve Golf Membership opportunity, allowing the next owner immediate access to the Jack Nicklaus Signature Golf Course at The Peninsula — a rare and highly sought-after advantage within this premier gated community. Located on a premium corner lot, built by Schell Brothers in 2019, this beautifully maintained Orchid model offers 3 bedrooms, 2 baths, enclosed porch and paver patio with pond views. Features include bright, open living spaces designed for comfort and effortless entertaining, dramatic vaulted ceilings with exposed beams, a stunning floor-to-ceiling stone gas fireplace, and custom built-ins, all surrounded by expansive windows that fill the home with natural light. The gourmet kitchen features granite countertops, stainless appliances, abundant cabinetry, and a large center island with seating, seamlessly flowing into the dining and living areas to create an ideal gathering space. All bedrooms are conveniently located on the main level, including the light-filled owner’s suite with tray ceiling, which opens directly to the outdoor living area. Enjoy the porch with vinyl tech windows, leading to a beautiful paver patio with seating and tranquil views of the community pond — perfect for morning coffee or evening relaxation. Upstairs, a second-floor bonus room provides flexible space ideal for a home office, guest retreat, or additional living area, along with an easily accessible finished walk-in storage room complete with a mini-split for heating and cooling. Additional features include a whole-home generator, custom closet in the owner suite and a 4 foot - forward bump out to the two car garage providing peace of mind and reliable comfort year-round. Located within The Peninsula on the Indian River Bay, residents enjoy an unmatched resort-style lifestyle in this private gated, master-planned community. Amenities include Delaware’s first private Jack Nicklaus Signature Golf Course, a stunning 34,000 sq ft clubhouse with dining and golf simulator, multiple pools including an indoor pool and the area’s only wave pool with sandy beach, a state-of-the-art fitness center, tennis and pickleball courts, full-service spa, scenic nature trails, a private bay beach with fishing pier, and on-site dining at the Terrace Grille. Experience luxury coastal living and world-class amenities at The Peninsula.

33457 Marina Bay Cir Unit #4, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$329,000
2 Beds 2 Baths
JUST REDUCED...Welcome to 33585 Windswept Drive #7303 in the highly sought-after Peninsula community of Millsboro. This beautifully appointed Sanibel model by Schell Brothers offers coastal elegance, golf course views, and resort-style living just minutes from the Indian River Bay. Located on the second level with elevator access this 2 bedroom, 2 bath condominium offers approximately 1,325 square feet of thoughtfully designed living space. The open floor plan seamlessly blends the kitchen, dining, and living areas, creating an inviting space perfect for entertaining or relaxing. Engineered wood flooring, crown moldings, recessed lighting, and a fireplace with glass doors and mantel add warmth and sophistication throughout. The galley-style kitchen features a breakfast bar, built-in microwave, pantry storage, and ample cabinetry. The spacious primary suite includes a walk-in closet and a luxurious ensuite bath with soaking tub and separate tub shower combination. A second bedroom and full bath provide comfortable accommodations for guests. Step outside to enjoy serene golf course and wooded views from your screened porch. With water-oriented living just approximately 2,000 feet from the Indian River Bay, this home offers the best of coastal Delaware. Residents of The Peninsula enjoy an unmatched amenity package including indoor and outdoor pools, fitness center, golf course and membership availability, clubhouse dining, tennis and basketball courts, walking trails, spa and sauna, private beach area, security gate, and more. HOA and condo fees cover exterior maintenance, lawn care, snow removal, trash, insurance, reserve funds, high-speed internet, and security for simplified living

33585 Windswept Dr Unit #7303, Millsboro

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$565,000
4 Beds 4 Baths
MOTIVATED SELLER! Act now—opportunity knocks with this beautifully maintained three-year-old townhome in the established, award-winning The Peninsula, Delaware’s only gated world-class resort community. The Cypress Point floor plan offers the convenience of one-level living with a spacious primary suite and laundry on the first floor, while the second level provides three additional guest bedrooms and a large family room, adding flexibility. Some furnishings available as a separate bill of sale. A welcoming front porch leads into the foyer and elegant dining room, which open onto a bright, airy floor plan that seamlessly connects the gourmet kitchen, living room, and sunroom. The kitchen is thoughtfully appointed with tall white maple cabinetry featuring full-extension soft-close drawers and doors, under-cabinet lighting, a tiled backsplash, a pot filler, and stunning quartz countertops. The center island anchors the space, complemented by stainless steel appliances including a gas cooktop, wall oven, microwave, dishwasher, and refrigerator with ice maker. The main-level primary suite features a spacious walk-in closet and a luxurious bath with a double-bowl quartz vanity, and a frameless glass shower with a ceramic tile backsplash. A full-size stackable washer and dryer, pantry, and powder room complete the first floor. Upstairs, one bedroom enjoys a private full bath, while another opens to its own balcony, and the fourth bedroom has a walk-in closet with a window. A second full bath, loft area, and expansive bonus room—ideal as a fifth bedroom or media room—offer additional living space, complete with double French doors and access to a covered second-level porch. Outdoor living is exceptional, with four separate outdoor spaces including two front porches and a backyard paver patio—perfect for entertaining. Additional features include James Hardie siding, exterior irrigation, Luxury Vinyl Wide Plank flooring throughout the main living areas, ceramic tile baths, smart thermostats, window treatments, and two wall-mounted TVs. Residents of The Peninsula enjoy an unparalleled lifestyle on 800 acres along the Indian River Bay, highlighted by a bayfront setting and a premier Jack Nicklaus Signature Golf Course. Amenities include a clubhouse with indoor and outdoor dining, a billiards room, a wine room, golf lounges, a pro shop, putting greens, a driving range, bocce courts, and more. The adjacent Lakeside Village features a full fitness center, spa, indoor pool, four outdoor pools, including an adult-only heated pool and sandy beach wave pool, hot tubs, miniature golf, poolside dining, tennis, pickleball, basketball, and two dog parks. Community fees include lawn care, landscape maintenance, snow and trash removal, Verizon Fios high-speed internet, HD cable, and 24-hour gated security. Located just thirteen miles from Lewes and Rehoboth Beach, this home also benefits from low Delaware property taxes and no sales tax. Live the life you deserve with luxury, convenience, and resort-style amenities at your doorstep.

22150 Dune Cir, Millsboro

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767

$340,000
3 Beds 2 Baths
Best value three bedroom condominium in the Peninsula. Welcome to Windswept Drive, Unit 9101! Perfectly positioned along the 6th fairway of the Jack Nicklaus Signature golf course, this residence enjoys a peaceful, private backdrop of golf, ponds and woods, with glimpses stretching toward the Indian River Bay. A pergola-covered patio extends the living space outdoors and invites quiet mornings or relaxed evenings overlooking the course. Inside, the gourmet kitchen features granite countertops, stainless steel appliances, custom display cabinetry, and a generous prep space, opening to the dining and living areas, ideal for effortless entertaining. The living room is anchored by a gas fireplace, built-in cabinetry and large windows that frame the serene outdoor views. The primary suite is a calming retreat with golf course views and a spa-inspired bath offering a double vanity, walk-in shower, soaking tub, and walk in closet. A second guest suite includes its own ensuite bath and walk in closet, while the thoughtfully added third bedroom (completed in 2019) provides flexible space for guests or a private home office and is unique to this floor plan. It's a convenient walk as you step outside and enjoy the Peninsula community with its world-class amenities and gated security. The clubhouse features a large restaurant with indoor and outdoor dining, billiards, wine, and game rooms, men's and women's lounges, a pro shop, putting greens, driving range, bocce courts, and the premier Jack Nicklaus golf course. The adjacent Lakeside village is home to the fitness center with an indoor pool, adult outdoor pool, wave pool and a very fun activity pool., The Lakeside grill offers breakfast, lunch and poolside dining all summer long. And don't forget the Tiki bar, weight room, fitness classes, hot tubs, sauna, spa rooms, game room, tennis, pickle-ball, dog park, community garden, nature center, bay beach, fishing pier and miles of walking trails. Enjoy year-round events and activities where you can make friends for a lifetime. Capital contribution to PCA is 0.5% of the sales price and $1250.00 to the Windswept condo. Club membership is additional and is required, choose from 3 levels, see disclosures.

33571 Windswept Dr Unit #9101, Millsboro

Listing courtesy of Compass. Contact: 3022734998