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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.

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:

$290,000

Welcome to 181 Bobby’s Branch Rd! A hidden gem tucked away in the peaceful surroundings of Millsboro. This property offers the perfect blend of privacy, space, and versatility, making it ideal for full-time living, a second home, or an investment opportunity. Step inside to discover a spacious and inviting layout designed for both everyday comfort and entertaining. The home features generous living areas filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. Outside, enjoy the backyard that provides plenty of room to relax, host gatherings, or expand your vision. Whether you're dreaming of a garden or outdoor oasis, the possibilities here are endless. Located just a short drive to Delaware’s beautiful beaches, shopping, dining, and local attractions, you’ll enjoy the best of both worlds, quiet country living with convenient access to everything you need. Don’t miss your opportunity to own a slice of tranquility in one of Sussex County’s fastest-growing areas.

3 Beds ⋅ 3 Baths

Welcome to 181 Bobby’s Branch Rd! A hidden gem tucked away in the peaceful surroundings of Millsboro. This property offers the perfect blend of privacy, space, and versatility, making it ideal for full-time living, a second home, or an investment opportunity. Step inside to discover a spacious and inviting layout designed for both everyday comfort and entertaining. The home features generous living areas filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. Outside, enjoy the backyard that provides plenty of room to relax, host gatherings, or expand your vision. Whether you're dreaming of a garden or outdoor oasis, the possibilities here are endless. Located just a short drive to Delaware’s beautiful beaches, shopping, dining, and local attractions, you’ll enjoy the best of both worlds, quiet country living with convenient access to everything you need. Don’t miss your opportunity to own a slice of tranquility in one of Sussex County’s fastest-growing areas.

181 Bobbys Br Unit 35, Millsboro

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$299,000

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.

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:

$219,900

Motivated to sell! Located in the desirable Villages at Millwood in Millsboro—where comfort, convenience, and coastal charm come together. This beautifully maintained 2-bedroom, 2 full bath home offers effortless, move-in-ready living with an inviting open floor plan designed for both relaxation and entertaining. The spacious primary suite features a walk-in closet, while the main living areas showcase stunning luxury vinyl plank flooring that adds both style and durability. Enjoy serene water views from not one, but two outdoor spaces—a screened-in porch perfect for morning coffee or evening unwinding, along with an open porch ideal for soaking in the peaceful surroundings. If you’re looking for easy living, this home delivers. Meticulously cared for and thoughtfully designed, it offers low-maintenance comfort just minutes from local shopping, dining, and all that coastal Delaware has to offer. Whether you're seeking a full-time residence or a relaxing retreat, this is a wonderful opportunity to enjoy the best of Eastern Shore living.

2 Beds ⋅ 2 Baths

Motivated to sell! Located in the desirable Villages at Millwood in Millsboro—where comfort, convenience, and coastal charm come together. This beautifully maintained 2-bedroom, 2 full bath home offers effortless, move-in-ready living with an inviting open floor plan designed for both relaxation and entertaining. The spacious primary suite features a walk-in closet, while the main living areas showcase stunning luxury vinyl plank flooring that adds both style and durability. Enjoy serene water views from not one, but two outdoor spaces—a screened-in porch perfect for morning coffee or evening unwinding, along with an open porch ideal for soaking in the peaceful surroundings. If you’re looking for easy living, this home delivers. Meticulously cared for and thoughtfully designed, it offers low-maintenance comfort just minutes from local shopping, dining, and all that coastal Delaware has to offer. Whether you're seeking a full-time residence or a relaxing retreat, this is a wonderful opportunity to enjoy the best of Eastern Shore living.

5205 Caitlins Way, Millsboro

Listing courtesy of Keller Williams Realty Delmarva. Contact:

$860,000

Welcome to 27582 S. Nicklaus Ave. Not only is this one of the BEST-PRICED homes with a PREMIUM LOCATION in Delaware's premier resort-style country club community, it is MOVE-IN READY with FRESHLY PAINTED EXTERIOR (July 2026) and a SPACIOUS, LOVINGLY REFRESHED INTERIOR, offered FURNISHED with few exclusions. Be prepared to enjoy PANORAMIC TEE-TO-GREEN 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 bath. 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 equipped with wet bar leading 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. Ready for your immediate enjoyment! 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, tennis and pickleball courts, 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, 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.

5 Beds ⋅ 5 Baths

Welcome to 27582 S. Nicklaus Ave. Not only is this one of the BEST-PRICED homes with a PREMIUM LOCATION in Delaware's premier resort-style country club community, it is MOVE-IN READY with FRESHLY PAINTED EXTERIOR (July 2026) and a SPACIOUS, LOVINGLY REFRESHED INTERIOR, offered FURNISHED with few exclusions. Be prepared to enjoy PANORAMIC TEE-TO-GREEN 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 bath. 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 equipped with wet bar leading 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. Ready for your immediate enjoyment! 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, tennis and pickleball courts, 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, 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:

$379,000

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!

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:

$321,000

PRICE IMPROVEMENT...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

2 Beds ⋅ 2 Baths

PRICE IMPROVEMENT...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:

$340,000

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 NEW 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.

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 NEW 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:

$629,000

FIRST Floor Primary Bedroom | Furnished | BEST PRICED SFH in the Peninsula!! Welcome to a home that breaks the mold at Peninsula Golf & Country Club. Bursting with personality, style, and bold design choices, every turn is a visual treat—think New York loft sophistication with a splash of Miami flair. Fun wallcoverings, vibrant color, and designer lighting create an atmosphere that is both playful and polished, making this home absolutely perfect for entertaining. The open main living and dining provide a seamless flow, ideal for gatherings large and small, featuring durable LVP flooring, a gas fireplace, built-ins, windows galore and a distinctive dining chandelier. Close by is a study with a striking glass barn door. The first-floor primary suite is a true retreat, offering hardwood flooring, custom closets, an updated spa-inspired bath and a beautiful walk-in shower. Outdoors, relax on the private patio that feels like your own personal escape. This 3-bedroom, 2.5-bath home has seen extensive recent improvements, including new HVAC and water heater, new refrigerator, microwave, dishwasher, disposal, washer, and dryer—allowing you to move right in with confidence. A conditioned crawlspace with interior access provides exceptional storage, a rare and valuable feature. Stylish, comfortable, and undeniably fun, this home delivers a fresh take on Peninsula living—where golf-course luxury meets creative expression. Beyond the home itself, The Peninsula offers an exceptional lifestyle with world-class amenities, including a Jack Nicklaus Signature golf course, driving range, elegant clubhouse with dining and lounge spaces, indoor and outdoor pools, fitness center, spa services, tennis and pickleball courts, dog park, community garden, walking trails, and a vibrant calendar of social events. Whether you’re seeking an active lifestyle or relaxed coastal living, The Peninsula delivers resort-style living at its finest. Membership in the country club is required, choose from 3 different levels, see disclosures.

3 Beds ⋅ 3 Baths

FIRST Floor Primary Bedroom | Furnished | BEST PRICED SFH in the Peninsula!! Welcome to a home that breaks the mold at Peninsula Golf & Country Club. Bursting with personality, style, and bold design choices, every turn is a visual treat—think New York loft sophistication with a splash of Miami flair. Fun wallcoverings, vibrant color, and designer lighting create an atmosphere that is both playful and polished, making this home absolutely perfect for entertaining. The open main living and dining provide a seamless flow, ideal for gatherings large and small, featuring durable LVP flooring, a gas fireplace, built-ins, windows galore and a distinctive dining chandelier. Close by is a study with a striking glass barn door. The first-floor primary suite is a true retreat, offering hardwood flooring, custom closets, an updated spa-inspired bath and a beautiful walk-in shower. Outdoors, relax on the private patio that feels like your own personal escape. This 3-bedroom, 2.5-bath home has seen extensive recent improvements, including new HVAC and water heater, new refrigerator, microwave, dishwasher, disposal, washer, and dryer—allowing you to move right in with confidence. A conditioned crawlspace with interior access provides exceptional storage, a rare and valuable feature. Stylish, comfortable, and undeniably fun, this home delivers a fresh take on Peninsula living—where golf-course luxury meets creative expression. Beyond the home itself, The Peninsula offers an exceptional lifestyle with world-class amenities, including a Jack Nicklaus Signature golf course, driving range, elegant clubhouse with dining and lounge spaces, indoor and outdoor pools, fitness center, spa services, tennis and pickleball courts, dog park, community garden, walking trails, and a vibrant calendar of social events. Whether you’re seeking an active lifestyle or relaxed coastal living, The Peninsula delivers resort-style living at its finest. Membership in the country club is required, choose from 3 different levels, see disclosures.

27535 S Nicklaus Ave, Millsboro

Listing courtesy of Compass. Contact:

$249,900

Welcome to 5306 Caitlins Way in the Villages at Millwood! This building includes an elevator to take you to this beautiful 3-bedroom, 2-bath third-floor unit. It offers a bright and open layout designed for both comfort and convenience. Step inside to find an open-concept kitchen and living room, perfect for everyday living and entertaining. The kitchen features a center island with bar seating, providing the ideal spot for casual meals or gathering with friends. Just off the living room, a sliding glass door leads to the four-seasons room with brand new screens, offering additional living space to enjoy year-round and views of the pond. The spacious primary suite includes a private bath with dual vanity sinks, while two additional bedrooms share a full hallway bathroom—perfect for guests, a home office, or extra space. Roof on the building just replaced. Enjoy a prime location close to shopping, dining, and all that Millsboro has to offer—schedule your showing today!

3 Beds ⋅ 2 Baths

Welcome to 5306 Caitlins Way in the Villages at Millwood! This building includes an elevator to take you to this beautiful 3-bedroom, 2-bath third-floor unit. It offers a bright and open layout designed for both comfort and convenience. Step inside to find an open-concept kitchen and living room, perfect for everyday living and entertaining. The kitchen features a center island with bar seating, providing the ideal spot for casual meals or gathering with friends. Just off the living room, a sliding glass door leads to the four-seasons room with brand new screens, offering additional living space to enjoy year-round and views of the pond. The spacious primary suite includes a private bath with dual vanity sinks, while two additional bedrooms share a full hallway bathroom—perfect for guests, a home office, or extra space. Roof on the building just replaced. Enjoy a prime location close to shopping, dining, and all that Millsboro has to offer—schedule your showing today!

5306 Caitlins Way, Millsboro

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$275,000

Charming 3-Bedroom Condo in Villages at Millwood – Millsboro, DE Welcome to easy living in the heart of Millsboro! This beautifully maintained 3-bedroom, 2-bath first-floor condo is located in the desirable Villages at Millwood—a vibrant community known for its comfort, convenience, and charm. Step inside to find a spacious open-concept layout with plenty of natural light, a well-appointed kitchen, and a private patio—perfect for relaxing or entertaining. The primary suite offers generous closet space and an en-suite bath, while two additional bedrooms provide flexibility for guests, a home office, or hobbies. Key Features: 3 bedrooms, 2 full bathrooms First-floor unit—no stairs to climb Low-maintenance living with lawn care and exterior upkeep included Access to the community clubhouse and seasonal outdoor pool Located within Millsboro city limits—easy access to town services Just minutes from shopping, dining, and everyday conveniences Whether you're looking for a primary residence, vacation home, or long term investment opportunity, this condo offers a winning combination of location, lifestyle, and value.

3 Beds ⋅ 2 Baths

Charming 3-Bedroom Condo in Villages at Millwood – Millsboro, DE Welcome to easy living in the heart of Millsboro! This beautifully maintained 3-bedroom, 2-bath first-floor condo is located in the desirable Villages at Millwood—a vibrant community known for its comfort, convenience, and charm. Step inside to find a spacious open-concept layout with plenty of natural light, a well-appointed kitchen, and a private patio—perfect for relaxing or entertaining. The primary suite offers generous closet space and an en-suite bath, while two additional bedrooms provide flexibility for guests, a home office, or hobbies. Key Features: 3 bedrooms, 2 full bathrooms First-floor unit—no stairs to climb Low-maintenance living with lawn care and exterior upkeep included Access to the community clubhouse and seasonal outdoor pool Located within Millsboro city limits—easy access to town services Just minutes from shopping, dining, and everyday conveniences Whether you're looking for a primary residence, vacation home, or long term investment opportunity, this condo offers a winning combination of location, lifestyle, and value.

5106 Caitlins Way Unit 5106, Millsboro

Listing courtesy of Iron Valley Real Estate at The Beach. Contact:

$779,000

Live graciously in this elegant home, nestled in the prestigious, thoughtfully planned country club community, the Peninsula. The Miller & Smith Hampton model is situated on the 3rd fairway of the signature Jack Nicklaus golf course in the 'Veranda' section. Elegant, low country style meets upscale convenience in this well maintained home, perfect for comfortable entertaining and hosting friends and family with discerning style. Find extensive custom details throughout. Beautiful millwork, crown molding, chair rail, box paneling, custom built-ins, as well as hardwood flooring and Bahama shutters grace this functional floor plan. **THIS IS THE LOWEST LIST PRICE FOR THE HAMPTON FLOOR PLAN IN 19 YEARS!** Off the east-facing second story front porch, the wide entry hall is flanked by a formal dining room and a glass doored study. The first of five bedrooms is just down the main entry hall, complete with custom built-ins and large closet. Pass the staircase, and the powder room into a large open living area and eat-in kitchen. The focal point of this ample living space is the natural gas fireplace, framed by large south-facing windows. Flooded with natural light, this room opens to the screened back porch spanning the width of the home which overlooks the third fairway. Enjoy a glass of wine on this beautiful perch, taking in a sunset moment at the end of your day. Adjacent to the open living area the gourmet kitchen runs the entire length of the space. Anchored by the oversized 10' granite island. The space is adorned with tall cabinetry, glass front wine storage, a gas range, wall ovens, coffee niche and a coordinating butler's pantry equipped with a wet bar - an entertainer's dream. Ascend the side staircase, complete with a custom, cap and bound stair runner onto the open gallery landing above. To the left, the spacious, western facing primary suite whispers relaxation. Large enough for a sitting area, and with access to the private third floor porch overlooking the course, you may never wish to leave your room. Two walk-in closets offer plenty of storage and the upgraded bath features a double sink vanity, jetted soaking tub, walk in shower, separate water closet and make-up vanity, all bathed in natural light from two charming corner windows. Across the landing, past the laundry room is the guest suite that will entice guests to overstay their welcome. A generous room with east facing windows, a reading nook and ensuite full bath. The lower level offers functionality with an open mud foyer off the oversized two car garage and a finished storage room. Drop your clubs, beach bag, or pool towels and head inside. Two more guest rooms complete the lower level, which share a jack-n-jill bathroom and both open to the lower rear porch. Perfect for houseguests to enjoy morning coffee or an evening nightcap. Come experience this sophisticated property. Live your best country club life at 27434 S Nicklaus Avenue in the Veranda, at the Peninsula. Note: Club Membership is mandatory at one of three tiers. Memberships offer access to extensive amenities, and the club and course are considered separate entities from HOA and COA's. The community offers four pools (one indoor) state of the art fitness center, a full-service spa, private beach, nature center, golf pro shop, billiards room, wine lounge and the award-winning restaurant, The Grille.

5 Beds ⋅ 4 Baths

Live graciously in this elegant home, nestled in the prestigious, thoughtfully planned country club community, the Peninsula. The Miller & Smith Hampton model is situated on the 3rd fairway of the signature Jack Nicklaus golf course in the 'Veranda' section. Elegant, low country style meets upscale convenience in this well maintained home, perfect for comfortable entertaining and hosting friends and family with discerning style. Find extensive custom details throughout. Beautiful millwork, crown molding, chair rail, box paneling, custom built-ins, as well as hardwood flooring and Bahama shutters grace this functional floor plan. **THIS IS THE LOWEST LIST PRICE FOR THE HAMPTON FLOOR PLAN IN 19 YEARS!** Off the east-facing second story front porch, the wide entry hall is flanked by a formal dining room and a glass doored study. The first of five bedrooms is just down the main entry hall, complete with custom built-ins and large closet. Pass the staircase, and the powder room into a large open living area and eat-in kitchen. The focal point of this ample living space is the natural gas fireplace, framed by large south-facing windows. Flooded with natural light, this room opens to the screened back porch spanning the width of the home which overlooks the third fairway. Enjoy a glass of wine on this beautiful perch, taking in a sunset moment at the end of your day. Adjacent to the open living area the gourmet kitchen runs the entire length of the space. Anchored by the oversized 10' granite island. The space is adorned with tall cabinetry, glass front wine storage, a gas range, wall ovens, coffee niche and a coordinating butler's pantry equipped with a wet bar - an entertainer's dream. Ascend the side staircase, complete with a custom, cap and bound stair runner onto the open gallery landing above. To the left, the spacious, western facing primary suite whispers relaxation. Large enough for a sitting area, and with access to the private third floor porch overlooking the course, you may never wish to leave your room. Two walk-in closets offer plenty of storage and the upgraded bath features a double sink vanity, jetted soaking tub, walk in shower, separate water closet and make-up vanity, all bathed in natural light from two charming corner windows. Across the landing, past the laundry room is the guest suite that will entice guests to overstay their welcome. A generous room with east facing windows, a reading nook and ensuite full bath. The lower level offers functionality with an open mud foyer off the oversized two car garage and a finished storage room. Drop your clubs, beach bag, or pool towels and head inside. Two more guest rooms complete the lower level, which share a jack-n-jill bathroom and both open to the lower rear porch. Perfect for houseguests to enjoy morning coffee or an evening nightcap. Come experience this sophisticated property. Live your best country club life at 27434 S Nicklaus Avenue in the Veranda, at the Peninsula. Note: Club Membership is mandatory at one of three tiers. Memberships offer access to extensive amenities, and the club and course are considered separate entities from HOA and COA's. The community offers four pools (one indoor) state of the art fitness center, a full-service spa, private beach, nature center, golf pro shop, billiards room, wine lounge and the award-winning restaurant, The Grille.

27434 S Nicklaus Ave Unit 76, Millsboro

Listing courtesy of Jack Lingo - Rehoboth. Contact:

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