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An extraordinary waterfront retreat offering rare privacy, expansive acreage & breathtaking views along Herring Creek, a tributary to Rehoboth Bay. Situated on an impressive 5.45-acres with approximately 1,300 feet of water frontage, this 3 Bedroom & 2 Bathroom Coastal-Colonial style home delivers a one-of-a-kind waterfront lifestyle. Step inside and you will be impressed with the thoughtful design and layout of the home offering spaces that were built for gathering, relaxing and taking in the water views. Notable interior features include a Primary Suite featuring & en-suite bath, a Formal Dining Room with Built-Ins, Kitchen w/Center Island & Eat-in nook, a spacious Living Room w/Bay windows, a Family Room w/Fireplace & Vaulted Beamed Ceilings and a generously sized Three-Seasons room with breathtaking views. You will also find a Bonus Room used previously as a craft room and an Office with private entrance. The Primary Bedroom, Living Room, Family Room and Three-Seasons Room enjoy serene water views! A staircase in the garage leads to unfinished Attic Space with room to grow. New roof around 2022! New HVAC August 2025! Venture outside to the Gazebo with Deck overlooking panoramic water views, surrounded by mature trees and open, protected lands for ultimate seclusion. There is not yet a dock on this property but all of the surrounding properties feature docks-offering exciting potential for the future. In the meantime, enjoy canoeing, kayaking & fishing off of your private lot, with access to the community dock and boat ramp. Located in the desirable Winding Creek Village community, just minutes from Route 24 and 8 miles to Lewes & Rehoboth beaches, award winning dining, and tax free shopping of Sussex County.

3 Beds ⋅ 2 Baths

An extraordinary waterfront retreat offering rare privacy, expansive acreage & breathtaking views along Herring Creek, a tributary to Rehoboth Bay. Situated on an impressive 5.45-acres with approximately 1,300 feet of water frontage, this 3 Bedroom & 2 Bathroom Coastal-Colonial style home delivers a one-of-a-kind waterfront lifestyle. Step inside and you will be impressed with the thoughtful design and layout of the home offering spaces that were built for gathering, relaxing and taking in the water views. Notable interior features include a Primary Suite featuring & en-suite bath, a Formal Dining Room with Built-Ins, Kitchen w/Center Island & Eat-in nook, a spacious Living Room w/Bay windows, a Family Room w/Fireplace & Vaulted Beamed Ceilings and a generously sized Three-Seasons room with breathtaking views. You will also find a Bonus Room used previously as a craft room and an Office with private entrance. The Primary Bedroom, Living Room, Family Room and Three-Seasons Room enjoy serene water views! A staircase in the garage leads to unfinished Attic Space with room to grow. New roof around 2022! New HVAC August 2025! Venture outside to the Gazebo with Deck overlooking panoramic water views, surrounded by mature trees and open, protected lands for ultimate seclusion. There is not yet a dock on this property but all of the surrounding properties feature docks-offering exciting potential for the future. In the meantime, enjoy canoeing, kayaking & fishing off of your private lot, with access to the community dock and boat ramp. Located in the desirable Winding Creek Village community, just minutes from Route 24 and 8 miles to Lewes & Rehoboth beaches, award winning dining, and tax free shopping of Sussex County.

9 Baypoint Rd, Millsboro

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$1,270,000

Welcome to 5 Baypoint Road in the waterfront community of Winding Creek Village. This property is located along Guinea Creek with access to the Rehoboth Bay. Situated on approximately 1.88 acres, the home offers 3,500 square feet of finished living space, 5 bedrooms, 3 full bathrooms, 1 half bath, a flex room on the first floor, and a 2-car garage, along with a circular driveway and landscaped grounds. The first floor includes three bedrooms, including a primary bedroom with a private screened porch overlooking the creek and wetlands. Additional main-level features include a living room with a stone fireplace, a family room, a flex room suitable for a home office or similar use, and a three-season porch that leads to the rear deck. The deck includes a built-in hot tub and provides extensive water views. The second floor includes two bedrooms and a full bathroom. The home also includes an unfinished basement with exterior walkout stairs, offering additional storage or future expansion possibilities. This large waterfront lot provides space for two private boat slips, offering convenient access for boating and water activities. Winding Creek Village provides a private setting while remaining close to area conveniences and the Delaware Beaches. 5 Baypoint Road offers a rare opportunity to enjoy a spacious waterfront property with direct creek access in a quiet coastal community.

5 Beds ⋅ 4 Baths

Welcome to 5 Baypoint Road in the waterfront community of Winding Creek Village. This property is located along Guinea Creek with access to the Rehoboth Bay. Situated on approximately 1.88 acres, the home offers 3,500 square feet of finished living space, 5 bedrooms, 3 full bathrooms, 1 half bath, a flex room on the first floor, and a 2-car garage, along with a circular driveway and landscaped grounds. The first floor includes three bedrooms, including a primary bedroom with a private screened porch overlooking the creek and wetlands. Additional main-level features include a living room with a stone fireplace, a family room, a flex room suitable for a home office or similar use, and a three-season porch that leads to the rear deck. The deck includes a built-in hot tub and provides extensive water views. The second floor includes two bedrooms and a full bathroom. The home also includes an unfinished basement with exterior walkout stairs, offering additional storage or future expansion possibilities. This large waterfront lot provides space for two private boat slips, offering convenient access for boating and water activities. Winding Creek Village provides a private setting while remaining close to area conveniences and the Delaware Beaches. 5 Baypoint Road offers a rare opportunity to enjoy a spacious waterfront property with direct creek access in a quiet coastal community.

5 Baypoint Rd, Millsboro

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$999,000

Welcome to 29 Winding Creek Drive, a rare opportunity to own a peaceful waterfront property in the desirable Winding Creek Village community. Perfectly situated along scenic Guinea Creek, this single-level ranch home offers direct water access with a private dock, complete with a boat lift and jet ski lift, making your coastal lifestyle effortless. As you step inside, a welcoming living room greets you to the right of the entryway. At the heart of the home, the kitchen and family room provide a comfortable gathering space, while the rear sunroom showcases panoramic water views—a true highlight of the property. The layout also includes three spacious bedrooms and two full baths, offering plenty of room for family and guests. A mudroom and laundry area connect seamlessly to the garage, with convenient access to the backyard. Outdoors is where this home truly shines. A paver patio leads directly to the private dock, overlooking the serene waters beyond. Here you can spend your days boating, crabbing, or simply relaxing as the sun reflects off the water. From Guinea Creek, you’ll enjoy easy boating access to the open waters of Rehoboth Bay, giving you endless opportunities to explore Delaware’s inland bays and beyond. Whether arriving by car or by boat, you’re only a short trip from Delaware’s premier beaches—Lewes and Rehoboth—plus award-winning golf at Baywood Greens and popular dining, shopping, and entertainment. This home is ready for some TLC, making it the perfect canvas for a new owner to create their dream waterfront retreat. For those looking for additional space or extra privacy, the lot immediately to the right of the home (27 Winding Creek Drive) is also available for purchase, offering a rare chance to expand or create a private waterfront estate. The land is also cross-listed on the MLS# DESU2093462. With its unbeatable location, private dock, and direct access to the bay, 29 Winding Creek Drive is your gateway to the best of Delaware’s coastal lifestyle.

3 Beds ⋅ 2 Baths

Welcome to 29 Winding Creek Drive, a rare opportunity to own a peaceful waterfront property in the desirable Winding Creek Village community. Perfectly situated along scenic Guinea Creek, this single-level ranch home offers direct water access with a private dock, complete with a boat lift and jet ski lift, making your coastal lifestyle effortless. As you step inside, a welcoming living room greets you to the right of the entryway. At the heart of the home, the kitchen and family room provide a comfortable gathering space, while the rear sunroom showcases panoramic water views—a true highlight of the property. The layout also includes three spacious bedrooms and two full baths, offering plenty of room for family and guests. A mudroom and laundry area connect seamlessly to the garage, with convenient access to the backyard. Outdoors is where this home truly shines. A paver patio leads directly to the private dock, overlooking the serene waters beyond. Here you can spend your days boating, crabbing, or simply relaxing as the sun reflects off the water. From Guinea Creek, you’ll enjoy easy boating access to the open waters of Rehoboth Bay, giving you endless opportunities to explore Delaware’s inland bays and beyond. Whether arriving by car or by boat, you’re only a short trip from Delaware’s premier beaches—Lewes and Rehoboth—plus award-winning golf at Baywood Greens and popular dining, shopping, and entertainment. This home is ready for some TLC, making it the perfect canvas for a new owner to create their dream waterfront retreat. For those looking for additional space or extra privacy, the lot immediately to the right of the home (27 Winding Creek Drive) is also available for purchase, offering a rare chance to expand or create a private waterfront estate. The land is also cross-listed on the MLS# DESU2093462. With its unbeatable location, private dock, and direct access to the bay, 29 Winding Creek Drive is your gateway to the best of Delaware’s coastal lifestyle.

29 Creek Dr, Millsboro

Listing courtesy of Keller Williams Realty Wilmington. Contact:

Selling Office: Patterson-Schwartz-Hockessin.

$828,750

TASTEFUL STYLE Charming and well-appointed, this home in the peaceful Winding Creek Village features 4 bedrooms plus a bonus room. The open floor plan provides great flow from the beautiful kitchen, which features stainless steel appliances, granite counters, and a center island open to the dining and living rooms. The living room boasts a two-story ceiling, gas fireplace and tons of natural light. This area connects to the owner’s suite, which includes a luxe private bath, an additional first floor guest room, and a home office. Upstairs features 2 more bedrooms, a full bath, and a bonus room. Entertain outdoors with ease from the expansive covered porch and beautifully landscaped backyard. The community includes a boat ramp and water access. Carefree living that's conveniently located only minutes from the beaches, boardwalk, and Coastal Highway shopping and dining!

4 Beds ⋅ 4 Baths

TASTEFUL STYLE Charming and well-appointed, this home in the peaceful Winding Creek Village features 4 bedrooms plus a bonus room. The open floor plan provides great flow from the beautiful kitchen, which features stainless steel appliances, granite counters, and a center island open to the dining and living rooms. The living room boasts a two-story ceiling, gas fireplace and tons of natural light. This area connects to the owner’s suite, which includes a luxe private bath, an additional first floor guest room, and a home office. Upstairs features 2 more bedrooms, a full bath, and a bonus room. Entertain outdoors with ease from the expansive covered porch and beautifully landscaped backyard. The community includes a boat ramp and water access. Carefree living that's conveniently located only minutes from the beaches, boardwalk, and Coastal Highway shopping and dining!

304 Island Rd, Millsboro

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: The Parker Group.

$772,500

TIMING IS EVERYTHING - DON'T MISS THE BOAT! 456 Woodside Road is the latest project from meticulous and thoughtful, lifelong builder, Everett E Gray. Though not a custom home, it feels like all the selections and finishes were chosen specifically with your needs in mind. The front facade garners attention for all the right reasons - the vertical siding, contrasting trim and complimentary stone work all draw you to the focal point - a generous, covered, front porch ideal for sipping your morning coffee. Transom windows flood the two-story foyer and study with natural light. The casual, open dining space to the right puts a modern spin on a more traditional floor plan, which flows easily past the bonus cabinetry and prep sink (historically known as a butler's pantry) into the well-equipped kitchen, complete with an oversized island, quartz counters, and soft-close cabinetry with pull-out shelving. From the kitchen and 2-story great room, all eyes are drawn to the green space behind the home - an expansive backyard accessible from the rear screened porch - a space that could easily incorporate an in-ground pool, hardscaped courtyard, and outdoor kitchen. Wide plank hardwood flooring is not only found throughout the main living spaces, it also extends into the first-floor primary suite, completed by a luxury owner's bathroom with oversized walk-in tiled shower. If you're tired of being underwhelmed by homes that lack storage with miniscule guest bedrooms, you'll be pleasantly surprised upon venturing to the second level. Even the secondary bedrooms offer some extra room to spread out, plus ample storage space. In fact, each bedroom has a walk-closet - and dual walk-ins in the primary suite. With easy access to nearby attractions and area beaches, Winding Creek Village also provides direct access to Indian River Bay via the community boat launch. Don't delay...SEIZE THIS OPPORTUNITY BEFORE IT SAILS AWAY!

4 Beds ⋅ 4 Baths

TIMING IS EVERYTHING - DON'T MISS THE BOAT! 456 Woodside Road is the latest project from meticulous and thoughtful, lifelong builder, Everett E Gray. Though not a custom home, it feels like all the selections and finishes were chosen specifically with your needs in mind. The front facade garners attention for all the right reasons - the vertical siding, contrasting trim and complimentary stone work all draw you to the focal point - a generous, covered, front porch ideal for sipping your morning coffee. Transom windows flood the two-story foyer and study with natural light. The casual, open dining space to the right puts a modern spin on a more traditional floor plan, which flows easily past the bonus cabinetry and prep sink (historically known as a butler's pantry) into the well-equipped kitchen, complete with an oversized island, quartz counters, and soft-close cabinetry with pull-out shelving. From the kitchen and 2-story great room, all eyes are drawn to the green space behind the home - an expansive backyard accessible from the rear screened porch - a space that could easily incorporate an in-ground pool, hardscaped courtyard, and outdoor kitchen. Wide plank hardwood flooring is not only found throughout the main living spaces, it also extends into the first-floor primary suite, completed by a luxury owner's bathroom with oversized walk-in tiled shower. If you're tired of being underwhelmed by homes that lack storage with miniscule guest bedrooms, you'll be pleasantly surprised upon venturing to the second level. Even the secondary bedrooms offer some extra room to spread out, plus ample storage space. In fact, each bedroom has a walk-closet - and dual walk-ins in the primary suite. With easy access to nearby attractions and area beaches, Winding Creek Village also provides direct access to Indian River Bay via the community boat launch. Don't delay...SEIZE THIS OPPORTUNITY BEFORE IT SAILS AWAY!

456 Woodside Rd, Millsboro

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$700,000

4 Beds ⋅ 3 Baths

88 Creek Dr, Millsboro

Listing courtesy of The Parker Group. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$639,000

This tranquil coastal retreat is nestled on over an acre of partially wooded land, facing the Guinea Creek Inlet on Rehoboth Bay. The charming, east facing brick front home offers an open floor plan designed for the homeowner who loves to entertain. 94 Creek Drive offers soaring ceilings, private outdoor space and partial water views. With an oversized family room, formal dining room, eat-in kitchen and west facing sunroom, this home offers ample space in a beautiful setting and is filled with stunning natural light. Multiple cozy destinations are ideal for quiet evenings at home. Large spaces are perfect for holiday dinners, cocktail parties, and gathering on game day. When entering the home you are immediately welcomed by the spacious family room with vaulted ceilings, skylights and custom niches flanking the center fireplace. The split floor plan separates the primary suite from secondary bedrooms. The primary suite has direct access to the laundry room for ideal functionality. Guest bedrooms are at the north side of the home, and share a double vanity hall bath. A rear sun deck is accessible from the primary suite, the living area and the sunroom/den, connecting all main living area to the outdoor space. The property offers wooded privacy, a two-car garage, brick front porch, outdoor shower and a garden shed. 94 Creek Drive is nine (9) homes away from the community boat slip! This property offers the rare combination of natural beauty, peaceful setting and convenience. Enjoy the tranquility just 20 minutes to local beaches, and 5 minutes from shopping and dining.

3 Beds ⋅ 3 Baths

This tranquil coastal retreat is nestled on over an acre of partially wooded land, facing the Guinea Creek Inlet on Rehoboth Bay. The charming, east facing brick front home offers an open floor plan designed for the homeowner who loves to entertain. 94 Creek Drive offers soaring ceilings, private outdoor space and partial water views. With an oversized family room, formal dining room, eat-in kitchen and west facing sunroom, this home offers ample space in a beautiful setting and is filled with stunning natural light. Multiple cozy destinations are ideal for quiet evenings at home. Large spaces are perfect for holiday dinners, cocktail parties, and gathering on game day. When entering the home you are immediately welcomed by the spacious family room with vaulted ceilings, skylights and custom niches flanking the center fireplace. The split floor plan separates the primary suite from secondary bedrooms. The primary suite has direct access to the laundry room for ideal functionality. Guest bedrooms are at the north side of the home, and share a double vanity hall bath. A rear sun deck is accessible from the primary suite, the living area and the sunroom/den, connecting all main living area to the outdoor space. The property offers wooded privacy, a two-car garage, brick front porch, outdoor shower and a garden shed. 94 Creek Drive is nine (9) homes away from the community boat slip! This property offers the rare combination of natural beauty, peaceful setting and convenience. Enjoy the tranquility just 20 minutes to local beaches, and 5 minutes from shopping and dining.

94 Creek Dr, Millsboro

Listing courtesy of Jack Lingo - Rehoboth. Contact:

Selling Office: Keller Williams Realty.

$590,000

Welcome to the highly sought-after waterfront community of Winding Creek Village, beautifully nestled along Guinea Creek in Long Neck, Delaware. This prime location offers easy boat access and is just minutes from the sparkling waters of Rehoboth Bay. Spend your warm summer evenings lounging by your private in-ground pool after 18 holes of golf or enjoy a day on the water exploring Delaware’s gorgeous inland bays. You're only a short drive from Delaware’s premier coastal beaches, including Lewes and Rehoboth Beach, and just seconds away from Baywood Greens — a stunning 18-hole public golf course consistently ranked among the very best in the state. Highlights of this spacious 3,020-square-foot coastal home with four-bedroom, three-bathroom and loft. The kitchen has been updated with new cabinetry stainless steel appliances, quartz countertops and a subway tile backsplash. The bathrooms have been updated with new tile flooring, vanities with Carrara marble counters top. A charming four-season room overlooking the pool. New Hardwood flooring and carpet throughout the home. The current owners also replaced the roof in 2022, new irrigation system, so you can mark that off your to-do list for the next several years. A community boat ramp and water privileges to Guinea Creek, with access to Rehoboth Bay, is another advantage of this Longneck area property. Imagine spending your summers in your very own backyard paradise at the Delaware beaches. Why wait? Call today and begin living in Delaware’s coastal region as soon as possible. This nearly three-quarter acre property can soon be your home base in Delaware’s popular coastal region . Don't miss this incredible opportunity to live the coastal lifestyle you've always dreamed of!

4 Beds ⋅ 3 Baths

Welcome to the highly sought-after waterfront community of Winding Creek Village, beautifully nestled along Guinea Creek in Long Neck, Delaware. This prime location offers easy boat access and is just minutes from the sparkling waters of Rehoboth Bay. Spend your warm summer evenings lounging by your private in-ground pool after 18 holes of golf or enjoy a day on the water exploring Delaware’s gorgeous inland bays. You're only a short drive from Delaware’s premier coastal beaches, including Lewes and Rehoboth Beach, and just seconds away from Baywood Greens — a stunning 18-hole public golf course consistently ranked among the very best in the state. Highlights of this spacious 3,020-square-foot coastal home with four-bedroom, three-bathroom and loft. The kitchen has been updated with new cabinetry stainless steel appliances, quartz countertops and a subway tile backsplash. The bathrooms have been updated with new tile flooring, vanities with Carrara marble counters top. A charming four-season room overlooking the pool. New Hardwood flooring and carpet throughout the home. The current owners also replaced the roof in 2022, new irrigation system, so you can mark that off your to-do list for the next several years. A community boat ramp and water privileges to Guinea Creek, with access to Rehoboth Bay, is another advantage of this Longneck area property. Imagine spending your summers in your very own backyard paradise at the Delaware beaches. Why wait? Call today and begin living in Delaware’s coastal region as soon as possible. This nearly three-quarter acre property can soon be your home base in Delaware’s popular coastal region . Don't miss this incredible opportunity to live the coastal lifestyle you've always dreamed of!

292 Pond Rd, Millsboro

Listing courtesy of Realty Mark Cityscape. Contact:

Selling Office: Bryan Realty Group.

$525,000

This water access community with boat ramp offers everything for those who are looking for space between homes and outdoor living. Offering a ranch style custom 3-bedroom, 2 bath, 2 car garage with additional 2 car garage on a spacious 1/2 acre plus. Welcome home as you enter into your open floor plan where the kitchen opens to the living and dining area. This split floor plan offers the owners suite on one side of the living area with additional guest bedrooms on the other side of the home. An addition to the rear of the home offers a vaulted ceiling living area with fireplace and lots of natural lighting. The manicured yard with irrigation and paver patio allows additional room for a pool or other features you adore. Priced to sell this home will not last long. Schedule your appointment today.

3 Beds ⋅ 2 Baths

This water access community with boat ramp offers everything for those who are looking for space between homes and outdoor living. Offering a ranch style custom 3-bedroom, 2 bath, 2 car garage with additional 2 car garage on a spacious 1/2 acre plus. Welcome home as you enter into your open floor plan where the kitchen opens to the living and dining area. This split floor plan offers the owners suite on one side of the living area with additional guest bedrooms on the other side of the home. An addition to the rear of the home offers a vaulted ceiling living area with fireplace and lots of natural lighting. The manicured yard with irrigation and paver patio allows additional room for a pool or other features you adore. Priced to sell this home will not last long. Schedule your appointment today.

458 Woodside Rd, Millsboro

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

Selling Office: Keller Williams Realty.

$505,000

Welcome to this move-in ready ranch home in desireable Winding Creek Village, offering the convenience of one-floor living. This property features 3 bedrooms and 2.1 bathrooms, with a recently replaced HVAC system (2023). Step inside to discover a spacious kitchen with center island. formal dining room, family room with gas fireplace and access to the rear yard. Retreat to the large primary bedroom with private en suite. Situated on over a half-acre, outside you'll find an elegant stone water table, outdoor shower, extensive hardscaping, and a built-in firepit for enjoying outdoor gatherings. The property also includes a shed, a triple-wide concrete driveway (great for boat storage), and oversized 2-car garage. The house was converted to public sewer in 2023. Residents of this water-oriented community have access to a community boat ramp, perfect for water enthusiasts! Don't miss out on the opportunity to own this exceptional property with quick access to the bay and seconds away from Baywood Greens golf course. Schedule your showing today!

3 Beds ⋅ 3 Baths

Welcome to this move-in ready ranch home in desireable Winding Creek Village, offering the convenience of one-floor living. This property features 3 bedrooms and 2.1 bathrooms, with a recently replaced HVAC system (2023). Step inside to discover a spacious kitchen with center island. formal dining room, family room with gas fireplace and access to the rear yard. Retreat to the large primary bedroom with private en suite. Situated on over a half-acre, outside you'll find an elegant stone water table, outdoor shower, extensive hardscaping, and a built-in firepit for enjoying outdoor gatherings. The property also includes a shed, a triple-wide concrete driveway (great for boat storage), and oversized 2-car garage. The house was converted to public sewer in 2023. Residents of this water-oriented community have access to a community boat ramp, perfect for water enthusiasts! Don't miss out on the opportunity to own this exceptional property with quick access to the bay and seconds away from Baywood Greens golf course. Schedule your showing today!

285 Pond Rd, Millsboro

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

Selling Office: RE/MAX Point Realty.

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