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$799,000
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
$719,000
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. Designed for effortless coastal living, Marina Bay lets you spend your time enjoying The Peninsula's world-class amenities and less time on home maintenance. Marina Bay offers the privacy of a detached home with much of the convenience and affordability of condominium ownership. Many of the major exterior maintenance responsibilities—including roof, exterior upkeep, irrigation and landscaping—are handled by the association, making it one of the most carefree lifestyles available at The Peninsula. Enjoy the financial benefit of lower insurance costs, with many exterior responsibilities covered by COA / HOA. 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
$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: 3023600300
$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
$629,000
3 Beds ⋅ 3 Baths
FIRST Floor Primary Bedroom! Price Improved! 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 newHVAC 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: 3022734998
$253,000
3 Beds ⋅ 2 Baths
Welcome to living 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: 3028460200
$275,000
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: (302) 541-8787
$779,000
5 Beds ⋅ 3 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. 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: (302) 227-3883