Condos for Sale in Millsboro, DE

Welcome to this charming 2-bedroom, 2-bathroom condo in the desirable Villages at Millwood community of Millsboro, Delaware. This well-designed home features an open floor plan that creates a spacious and inviting atmosphere, perfect for everyday living and entertaining. The light-filled kitchen opens seamlessly to the living area, where luxury vinyl plank flooring adds both style and durability. A sliding glass door leads to a private porch, providing the perfect spot to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are comfortably carpeted, offering warmth and comfort, while the two full bathrooms feature convenient tub/shower combinations. A washer and dryer are included in the unit for added convenience and long term rentals are permitted for those seeking in investment property. Special note: the hot water heater and HVAC system are just 1 year old. Ideally located just east of Route 113, Villages at Millwood offers easy access to a variety of dining options, grocery stores, and major retailers. Route 20 is nearby and provides a direct route to Delaware's beautiful beaches, making this an excellent location for both year-round living and coastal getaways.

2303 Caitlins Way, Millsboro

Listing courtesy of Compass. Contact:

$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:

$210,000

2 Beds ⋅ 2 Baths

Welcome to the Villages of Millwood, where you'll find this cozy 2-BR, 2-BA Condo. Recent improvements include new laminate flooring and new water heater. Extras include appliances including washer and dryer. Sliding glass doors leading to the screened porch and deck for relaxation on these summer evenings. The Villages at Millwood is ideally located near Millsboro's shopping, dining, and everyday conveniences. Just a short drive away, enjoy the Delaware beaches, golf courses, boating on the Indian River Bay, and popular destinations like Rehoboth Beach, Bethany Beach, and Lewes. This could be your AFFORDABLE home for the beach life!!!

3202 Caitlins Way, Millsboro

Listing courtesy of The Real Estate Market. Contact:

$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:

$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:

$290,000

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

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

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

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

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

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

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:

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