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$7,950,000
5 Beds ⋅ 6 Baths ⋅ 73543062 MLS
Nestled in the highly coveted enclave of Acoaxet and Westport Harbor, this magnificent coastal estate at 169 Atlantic Ave offers the pinnacle of New England waterfront living. Meticulously reimagined from top to bottom, this home underwent a complete, high-end remodel completed in 2021. Sited flawlessly to maximize panoramic views of the open Atlantic Ocean, sandy shorelines, and the Elizabeth Islands, this property seamlessly blends classic Shingle-style architecture with unparalleled private luxury.

169 Atlantic Avenue, Westport

Listing courtesy of Listing Agent: Kirk Schryver Team from Listing Office: Compass.
$4,500,000
73469055 MLS
Welcome to Phase One of Heritage Acres(33.5 acres), a unique development opportunity comprising one of six parcels within a larger 238-acre tract. This parcel is accessible via a paper street and offers significant potential for future development.A conceptual subdivision plan, originally approved by the Planning Board in the 1970s, reflects a layout of smaller residential lots; however, it is important to note that wetlands were not considered under the original approval. Based on preliminary review, this parcel may accommodate approximately 30 to 45 lots, subject to current zoning, environmental review, and permitting.The property is being offered as-is. No percolation tests or engineering studies have been completed to date.This land presents an excellent opportunity for a variety of development concepts, including a cottage cluster community, smaller single-family homes, or a 55+ residential community featuring compact homes and low-maintenance yards.

Hertitage Acres, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$3,250,000
5 Beds ⋅ 2 Baths ⋅ 73572447 MLS
Set on high, this 17+/- pastoral estate is located in coveted South Westport. The exceptionally well-built shingled residence offers remarkable privacy, versatility, and the potential to create a true legacy family compound. Approached by a private lane, framed by ancient stone walls and mature plantings, the substantial home is impressively sited well beyond the flood zone. A gracious gallery foyer opens through French doors to a formal living room with custom built-ins and an elegant, banquet-size dining room. The chef’s kitchen features an expansive island, dual ovens and cooktops, and a wall of glass overlooking the sweeping grounds. At the rear, an expansive fireplaced great room offers multiple seating areas and casual dining area, with French doors opening to the spacious deck. A private office with built-ins, and adjacent bath, completes the main level. Upstairs, a generous landing leads to multiple bedrooms and baths, all enjoying tranquil pastoral views. The third floor is a retreat unto itself, with a spacious fireplaced living area, kitchenette, spa-like bath, and private balcony capturing dramatic views across the property. A detached indoor pool and pool house with bath and laundry, three-bay garage, and workshop complete this extraordinary offering. With potential for several additional lots, the property presents a rare opportunity for multi-generational living or the creation of a private family compound. Just minutes from white sandy beaches, conservation lands, and Westport’s shops and restaurants, this distinctive South Westport estate combines substantial construction, exceptional acreage, privacy, and possibilities for generations to come.

1069 Horseneck Rd, Westport

Listing courtesy of Listing Agent: William J. Milbury from Listing Office: Milbury and Company.
$3,000,000
73205954 MLS
Fantastic farmland with unlimited potential in beautiful South Westport. One parcel containing 99+ acres with 900+ feet of frontage on Sodom Rd. An unpaved access road in place gives way to the rear of the property. No engineering has been done. Improve this land and build something remarkable.

978 Sodom Rd, Westport

Listing courtesy of Listing Agent: Gregg S. Rutch from Listing Office: HomeSmart First Class Realty.
$2,850,000
3 Beds ⋅ 4 Baths ⋅ 73545632 MLS
Located in the heart of Acoaxet, this exceptional pondfront home offers the ultimate coastal retreat with sweeping ocean views and spectacular sunsets over Richmond Pond. Recently renovated, the residence is in pristine condition. The living space combines contemporary comfort with timeless coastal charm. An open floor plan creates a bright, versatile living space ideal for both everyday living and entertaining. Multiple decks seamlessly extend the interior living areas outdoors, providing inviting spaces to relax, dine, and enjoy the warmer summer months surrounded by breathtaking water views. Perfectly situated in one of Acoaxet’s most coveted neighborhoods, the property is within walking distance of ocean beaches and a wide variety of summer activities. The tranquil pondfront setting, combined with expansive views stretching to the ocean, makes this a truly special offering.

3 Richmond Pond, Westport

Listing courtesy of Listing Agent: Deborah L. Ladd from Listing Office: Compass.
$2,750,000
73520844 MLS
Welcome to 272 Pine Hill Road in Westport — home to the well known Pine Hill Dairy. Set on approximately 63 acres of 61A agricultural land, this rare property offers a unique opportunity for farmers, investors, or buyers seeking expansive acreage in a scenic rural setting. The property has operated as a working dairy farm until recently and features open farmland extending deep into the rear of the property.The existing home is in need of a full rehabilitation and the property is being sold strictly “as is.” No wetlands have been delineated, no perc testing has been completed, and no subdivision approvals or engineering have been pursued. Buyers to perform their own due diligence regarding potential uses, permitting, and development possibilities. A rare chance to restore, preserve, or reimagine a longstanding Westport farm property with substantial acreage and agricultural history.

272 Pine Hill Rd, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$2,300,000
2 Beds ⋅ 3 Baths ⋅ 73527284 MLS
Welcome to 246 Howland Road, an extraordinary coastal retreat where modern luxury meets timeless New England charm in the heart of Acoaxet Village. Long regarded as one of New England's most exclusive seaside communities, Acoaxet Village is known for its private beaches & clubs offering golf, tennis, dining and sweeping views of the Westport River and Atlantic Ocean. Completely rebuilt in 2019, this custom-designed home was thoughtfully crafted to maximize natural light, ocean breezes, & water views from nearly every room. The residence offers over 2,600sf of beautifully appointed living space with exceptional attention to detail throughout. The spacious living areas offer hardwood floors, high end finishes & an open floor plan. One of the home's most distinctive features is the stunning upper-level viewing areas, offering breathtaking panoramic water views where you can enjoy both sunrises and sunsets! Schedule a private showing today & close in time to enjoy this summer's festivities

246 Howland Rd, Westport

Listing courtesy of Listing Agent: Jennifer DaPonte from Listing Office: Keller Williams Coastal.
$2,275,000
3 Beds ⋅ 3 Baths ⋅ 73544215 MLS
Tucked away, 70 Third Street feels both private and unexpectedly special, where thoughtful details have been purposely placed throughout the grounds and the home itself. Zen like landscaping surrounds this contemporary creating a serene outdoor oasis while offering sweeping views of the Atlantic Ocean. An amazing chef's kitchen features windows that open directly onto a sheltered deck. A living room floor to ceiling fireplace and soaring vaulted ceiling opening to a second floor balcony create volume, light, and architectural interest. Encompassing the entire second floor, the primary suite includes a sitting area and private deck for a quiet retreat while two lower level bedrooms enjoy direct access to the peaceful courtyard offering the ever-present connection to nature. Adding to the property's rare waterfront appeal, a private dock offers direct access to the tidal inlet leading to the tranquil "let" portion of the Westport River, making this truly a unique coastal retreat.

70 Third, Westport

Listing courtesy of Listing Agent: Kathleen Santos from Listing Office: Residential Properties Ltd..
$2,275,000
5 Beds ⋅ 4 Baths ⋅ 73535521 MLS
Set on a peaceful 1.13-acre parcel just steps from the Acoaxet Club and a short walk or bike ride to the beach, this exceptional Westport Harbor property offers a rare blend of privacy, comfort, and coastal charm. Designed for effortless indoor-outdoor living, the grounds feature bluestone patios with western exposure, majestic trees, mature landscaping, and a saltwater pool. The stunning 2,257 sqft. addition showcases vaulted ceilings, an open-concept living and dining area with fireplace, a chef’s kitchen with Vermont soapstone and custom wood counters, library, large screened porch, and a sumptuous primary suite with steam shower, soaking tub, and steps out to an outdoor shower. The rebuilt 1,681 sqft. four-bedroom, two-bath wing with fireplaced living room and a second outdoor shower provides abundant space for family and friends. Convenient to Adamsville, Tiverton Four Corners, and Little Compton. A true stunner in an ideal location!

115 Howland Road, Westport

Listing courtesy of Listing Agent: Cherry Arnold from Listing Office: Mott & Chace Sotheby's International Realty.
$2,149,000
3 Beds ⋅ 3 Baths ⋅ 73543263 MLS
Experience waterfront living on the scenic East Branch of the Westport River. Privately set back approximately 500 feet from a quiet, horseshoe road, this exceptional property offers a rare blend of privacy, tranquility, and picturesque river views. The open-concept design features a sun-filled kitchen, spacious bedrooms, cathedral ceilings, and a primary suite with a private balcony overlooking the beautifully landscaped grounds and river. Enjoy outdoor living on the spacious deck, stone patio, or walk down to your private dock while kayakers and small boats drift by. Take a leisurely stroll along scenic Drift Road to the Head Town Landing Country Store for fresh coffee and homemade doughnuts. Private and public beaches are only minutes away. Whether you're entertaining guests, relaxing by the water, or simply taking in the peaceful surroundings, this remarkable property offers the perfect balance of waterfront beauty and privacy in one of Westport's most desirable settings

3 Sandpiper Dr, Westport

Listing courtesy of Listing Agent: Gregory Dantas from Listing Office: NE Real Estate Services.
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 73543126 MLS
Welcome to 2037 Main Road, an extraordinary waterfront home on historic Westport Point where American history, timeless New England architecture, and an exceptional coastal lifestyle come together. Originally built in 1776, this remarkable residence has been thoughtfully updated while preserving the character and craftsmanship that make historic homes so special.Perfectly sited to capture breathtaking sunsets, the property overlooks the harbor with panoramic water views and features a private dock, making it easy to enjoy boating, kayaking, fishing, or simply relaxing by the water. Inside, the home is rich with historic charm, featuring wide plank hardwood floors, exposed hand-hewn beams, original woodwork, fireplaces, and period architectural details that reflect nearly 250 years of history. A thoughtfully designed addition blends seamlessly with the original home while expanding the living space and taking full advantage of the stunning waterfront setting. Large windows frame spectacular harbor views from both the first and second floors, filling the home with natural light and creating an effortless connection between the indoors and outdoors.The renovated kitchen complements the home's historic character while offering the functionality and conveniences today's homeowners appreciate. Throughout the home, pride of ownership is evident, with numerous improvements including owned solar panels, Pella windows, a newer roof, updated heating system, generator, and newer septic system, allowing you to enjoy the beauty of a historic property with the peace of mind of modern updates.Adding to the property's appeal is a charming detached cottage filled with rustic character. Ideal for guests, a home office, artist's studio, or private retreat, it offers incredible flexibility while maintaining the authentic coastal feel of the property.The beautifully landscaped grounds feature mature gardens and inviting outdoor spaces, making the most of the manageable lot while creating a peaceful waterfront setting for entertaining or quiet relaxation.Located in the heart of desirable Westport Point, you'll enjoy one of New England's most picturesque waterfronts, just moments from beaches, marinas, conservation land, and local dining. Historic waterfront properties with a private dock, guest cottage, stunning sunsets, and thoughtfully integrated modern improvements rarely become available. This is a unique opportunity to own a true legacy property.

2037 Main Rd, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$1,950,000
5 Beds ⋅ 4 Baths ⋅ 73565341 MLS
Location, location, location. A hidden treasure in plain sight, this home is full of delightful surprises. Step inside and ascend two steps to the heart of the home: a beautifully designed chef’s kitchen filled with natural light, plenty of counter space, ample cabinetry, and room for a table and chairs. The kitchen is flanked by a spacious dining room—also ideal as a home office—and a cozy den featuring a wet bar and decorative tile fireplace. Just three steps down, the generous family room impresses with a cathedral ceiling and walls of windows on three sides, overlooking the private backyard. Through the trees, enjoy glimpses of the Acoaxet Club’s third fairway. A large, private corner deck, accessible from both the kitchen and den, provides an ideal setting for relaxing or entertaining. The thoughtful open-space design creates an airy, inviting feel throughout the first floor .The second floor offers four generously sized bedrooms and two full bathrooms. The entire third floor is dedicated to the private primary suite, complete with an intimate deck—perfect for enjoying morning coffee. Attractive, detailed landscaping enhances the exterior, completing this wonderful home designed for comfortable family living and memorable gatherings with friends.

94 Howland, Westport

Listing courtesy of Listing Agent: Eleanor Wickes from Listing Office: Mott & Chace Sotheby's International Realty.
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73560762 MLS
Presented at 15 Briggs Rd, Westport, MA, this distinguished totally modernized renovated residence, encompassing 3700+SF. of refined living space, offered on a compelling blend of classic design and expansive grounds. This property is particularly noteworthy for its unique attached 2000 SF enclosed area for your "SUPRISE" a private year round heated inground swimming pool on a generous 5.99 acre lot, providing an unparalleled sense of privacy and potential for outdoor pursuits. The residence features four thoughtfully appointed bedrooms, offering flexible arrangements for residents and guests. Complementing these are three full bathrooms and one half bathroom, designed to accommodate the demands of a dynamic household with both functionality and comfort. An attached garage provides convenient and secure vehicle storage, enhancing the practical aspects of daily living. We invite you to discover the unique potential and serene lifestyle offered by this exceptional Westport property.

15 Briggs Rd, Westport

Listing courtesy of Listing Agent: Antonio F Alberto from Listing Office: Alberto Real Estate.
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73530641 MLS
Amazing 4 bedroom, 2.5 bath, colonial-style home set on a private 2.2-acre wooded lot, surrounded by gorgeous gardens and outbuildings. The original historic home was renovated down to the studs and added on to in 2010. You’ll find a central kitchen w/ granite counters and stainless appliances open to a formal dining room w/ beautiful wainscoting, and the large sunny living room w/ wood stove and millwork. Head upstairs to 3 bedrooms, including the large primary w/ walk-in closet, ensuite bath w/ soaking tub and glass shower and an expansive balcony overlooking the gardens. The finished 3rd floor has a family/TV room, bedroom and home office space. The finished basement offers even more living space. Relax on the new front porch while you take in the cottage gardens, fire pit, and potting shed. Gas hydro air heat/central A/C system. Solar panels & accessory building.

178 Pine Hill Rd, Westport

Listing courtesy of Listing Agent: Jocelyn Demakis-Daluz from Listing Office: Demakis Family Real Estate, Inc..
$1,250,000
4 Beds ⋅ 2 Baths ⋅ 73521379 MLS
Welcome to 129 Cross Road in the desirable Acoaxet area of Westport, a charming former Acoaxet schoolhouse filled with coastal character and timeless appeal. This 4-bedroom, 2-bath home is currently enjoyed as a year-round residence but is equally well suited as a vacation or seasonal retreat.The flexible floor plan includes a first-floor primary bedroom that can also serve as a guest room, home office, or additional living space to fit your needs. Surrounded by classic New England stone walls and situated on approximately a half-acre, the property offers a manageable yard, giving you more time to enjoy the nearby beaches and waterfront lifestyle.The home has been well maintained over the years and features a full poured concrete foundation beneath the entire house, an updated electrical panel, newer roof and windows, an updated kitchen and second-floor bath, and air conditioning on the first floor. The front porch is in need of updating, offering an opportunity to add your own finishing touches.Additional amenities include a one-car garage and a storage shed, ideal for beach gear, bicycles, and outdoor equipment.Ideally located near the Acoaxet Club, Elephant Rock, Westport Harbor, and the area's beautiful beaches, this property offers a wonderful opportunity to enjoy one of Westport's most sought-after coastal neighborhoods.Title V has failed and will be the buyer's responsibility.

129 Cross Rd, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$1,249,000
4 Beds ⋅ 4 Baths ⋅ 73542196 MLS
Welcome to a stunning new construction contemporary colonial offering the perfect blend of modern luxury and waterfront living. This 4,150 sq. ft. home features two primary suites, one on each floor plus 2- additional bedrooms and four full baths. Enjoy an open-concept living area, a chef’s kitchen with a granite island, breakfast bar, and spacious dining area, plus a formal dining room for entertaining. A dedicated home office on the first floor is ideal for remote work. Step outside to two oversized composite decks with breathtaking views, and enjoy direct shore access for kayaking, paddle boarding, and boating right from your backyard. An unfinished basement offers endless possibilities, home theater, gym, or entertainment space. 2-car attached garage and 10 additional parking spots provide ample space for family and guests. Located in one of Westport most desirable waterfront communities, close to marinas, beaches, dining, shopping.

920 Drift Road, Westport

Listing courtesy of Listing Agent: Mina Shenouda from Listing Office: Keller Williams South Watuppa.
$1,225,000
3 Beds ⋅ 3 Baths ⋅ 73549422 MLS
Own a piece of Westport history with the William Kirby House, a classic antique Cape that has been lovingly cared for through generations. Thoughtfully designed for comfortable everyday living, this home offers an easy flow while perserving period details, including wainscoting, two center fireplaces, and classic window designs. Beautiful fir flooring flows throughout. Exposed beams add height and architectural interest to the centrally located kitchen, while a former birthing room offers a practical home office space. In 2019, a modern first-floor primary suite was masterfully added, blending antique design with custom construction to create a retreat that rivals those found in newer homes. A stacked w/d in the mudroom/bath adds to the ease of first floor living. Several access points lead to the stone patio, making outdoor entertaining simple and inviting. Set on a beautifully cared-for yard on desirable Drift Road, this special home is a rare opportunity you won't want to miss.

1263 Drift Road, Westport

Listing courtesy of Listing Agent: Kathleen Santos from Listing Office: Residential Properties Ltd..
$1,100,000
3 Beds ⋅ 4 Baths ⋅ 73570197 MLS
Welcome to the desireable Westport neighborhood of Meadowbrook Farms. This 2014 built home features open foyer, formal dining room w/hardwood floors, large open kitchen w/stainless steel appliances, polished stone countertops, and ample cabinet space to meet all of your needs. The spacious livingroom features a gas fireplace and leads to an wonderful outdoor deck. The large, first floor primary suite features a large walk-in closet and private bath with jet tub and shower. In addition, a formal dining room and office space finishes the main level of the home.The second offers two more good sized bedrooms along with a full bath and cat walk overlooking the living room. Lower level features a partially finished Family/Rec room with half bath and exterior patio access. Central air throughout the home and a whole house generator keep you comfortable and safe regardless of the weather. Property features manicured lawn & flower beds, fenced in yard great for pets & small children, custom shed, large 2 car garage w/storage, 6 add'l off street parking spaces.

20 Meadowbrook Ln, Westport

Listing courtesy of Listing Agent: The Highland Group from Listing Office: Keller Williams South Watuppa.
$1,100,000
6 Beds ⋅ 2 Baths ⋅ 73569994 MLS
Welcome to 1885/1885A Main Road on Historic Westport Point - a wooded 1 acre lot with multiple homes. Rare opportunity to own this quintessential New England coastal summer estate in the heart of Westport Point Historic District! It has been in the same family for decades! Experience life in an old whaling village listed on the National Registry of Historic Places. Stroll down charming Main Road towards "Pacachuk Point", past beautiful houses with historic plaques. This unique property is truly a 1 acre hidden gem you could drive by and never notice. Main house takes you back to a much simpler time period. It consists of 6 bedrooms, a covered porch, and a red brick fireplace that is the focal point of the large living room. The storybook guest cottage with its own 2 bedrooms sits nearby. A property to make memories on.

1885/1885A Main Road, Westport

Listing courtesy of Listing Agent: John R. Gifford from Listing Office: Even Keel Realty, Inc..
$1,099,000
4 Beds ⋅ 4 Baths ⋅ 73527301 MLS
MOTIVATED SELLER Welcome Home! Located on a quiet cul-de-sac at 6 Angel Court Westport, this 4 bedroom 3.5 bathroom home offers privacy, comfort, and coastal charm. Built in 2008, one owner! Featuring a bright living space enhanced by elegant decorative venetian plaster walls giving the home a unique look. The custom chefs DREAM kitchen has not one BUT two cooking stoves with custom hoods and beautiful granite countertops that run seamless into the backsplash. The Dining room has a full wall of custom pantry cabinets for plenty of storage space. There is an additional lounge room on the main floor perfect for entertaining. The finished basement has great potential for an in-law setup, while the 30x50 detached garage with a heating and cooling unit, has great potential for an ADU. The backyard of this home is a perfect space to entertain during those amazing New England summer nights, take a dip in the above ground salt water pool ready for you for this summer!!!!!Seller is offering 2% buyer agent commission

6 Angel Ct, Westport

Listing courtesy of Listing Agent: Team ROSO from Listing Office: RE/MAX Vantage.
$979,900
3 Beds ⋅ 1 Baths ⋅ 73552203 MLS
Discover the charm of this unique post-and-beam Cape with 2-3 bedrooms and 1 bathroom with rough plumbing for a second bathroom, ideally located just minutes from Westport Harbor and local favorites like Horseneck Beach.Step inside to an inviting open concept floor plan filled with warmth and character, featuring stunning exposed wood beams, abundant natural light, and timeless New England appeal. The home offers two levels of comfortable living, complete with forced hot air (natural gas) and for those hot Summer days, central air along with a partially finished walkout basement that provides excellent potential for additional finished living space, a home office, or recreation area. Nestled on over 1.3 acres of private wooded land, the secluded driveway leads to your own peaceful retreat in one of Westport’s most desirable locations. Whether you’re looking for a year-round residence or a coastal getaway, this property offers the perfect combination of privacy, charm, and convenience to the harbor, beaches, and all that Westport has to offer.

1746E Drift Rd, Westport

Listing courtesy of Listing Agent: Kyle Costa from Listing Office: Bayshore's Capital and Real Estate, Inc..
$950,000
3 Beds ⋅ 2 Baths ⋅ 73506054 MLS
Welcome to 3 Diane Way, a beautifully designed new construction home offering modern comfort, thoughtful craftsmanship, and a serene setting. Situated on a generous 1.4-acre corner lot, this home is available for reservation prior to completion and is scheduled for delivery at the end of 2026. The layout features 3 bedrooms, 2 full bathrooms, and a spacious 2-car garage. An open-concept design is complemented by a designer kitchen with premium stainless steel appliances, ideal for both everyday living and entertaining. The primary suite offers a tray ceiling, custom walk-in closet, and private bath. A full walk-out basement provides excellent potential for future living space, a home gym, or additional storage. Built to the builder’s design with some buyer selections, this home ensures a cohesive and well-executed finish throughout. Enjoy the privacy of a corner lot settled in this desirable neighborhood in Westport

3 Diane Way, Westport

Listing courtesy of Listing Agent: Jordan St. Fort from Listing Office: Botelho Agency LLC.
$899,000
73521212 MLS
Prime 1.67-Acre Homesite — Westport HarborDiscover a rare 1.67-acre homesite tucked in a private, mature cul-de-sac of only eight exclusive parcels. Fully wooded and supported by a completed perc test, this site allows for selective clearing to welcome abundant natural light while preserving the most attractive sightlines for a custom residence.Located in the coveted Acoaxet Harbor area, the property sits about one mile from the marina, beaches, golf, tennis, and equestrian facilities—offering the perfect balance of seclusion and easy access to premier recreational amenities. Custom architectural plans and comprehensive construction services are available for buyers seeking a turnkey build.An exceptional opportunity to create a thoughtfully designed, high-end home in a truly special place of paradise.

19 Seabury Lane, Westport

Listing courtesy of Listing Agent: Nelson Bernardo from Listing Office: Bernardo Real Estate.
$895,000
3 Beds ⋅ 2 Baths ⋅ 73535344 MLS
Become the next Curator of this Head of Westport Gem! The "J.P. Gifford House" has been tastefully and historically renovated throughout! This 3 bedroom, 2 bath home offers the ambiance of the "old with the new". Fully restored with a new eat-in new kitchen, bathrooms, wiring, heating, plumbing, period wood roof & antique shutters. Refinished oak and fir floors, fully insulated with a 2 stall oversized garage with double doors and loft area. Relax on the rear patio with sun- shade, take an outdoor shower after a day at the beach, or enjoy some time in the antique bunk house. Enjoy views of the historic East Branch of the Westport River, drop your kayak in for a scenic tour, or enjoy your backyard bound by stone walls!

41 Drift Road, Westport

Listing courtesy of Listing Agent: James Sabra from Listing Office: Equity Real Estate.
$825,000
3 Beds ⋅ 2 Baths ⋅ 73540304 MLS
Welcome to 1775 Drift Road, ideally located in desirable South Westport, just minutes from local beaches, Westport Point, and the best of coastal living. This contemporary home offers a spacious feel with a versatile floor plan ideal for year-round living or a seasonal retreat.The living room is the centerpiece of the home, featuring a stunning real stone fireplace & cathedral ceilings that create warmth and character. Hardwood floors run throughout the home. The private primary suite features its own balcony, while two additional bedrooms are located on the main level. The flexible layout also offers the potential for a first-floor primary bedroom.Privately set among mature trees, the property offers exceptional seasonal privacy. Enjoy outdoor living on the wrap-around deck or relax in the covered breezeway. Additional features include a two-car garage,newer roof,home generator, & finished basement. Exceptional South Westport location, just moments from beaches, boating & dining.

1775 Drift Rd, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$775,000
2 Beds ⋅ 1 Baths ⋅ 73543642 MLS
Welcome to 99 Sylvia Lane in South Westport, where this beautifully renovated cottage offers breathtaking westerly views of the East Branch of the Westport River. Rebuilt from the studs, the home features all-new plumbing, heating, insulation, electrical, windows, siding, and a thoughtfully redesigned interior that makes the most of every square foot. Whether you're looking for a year-round residence or the perfect vacation getaway, this turnkey property is ready to enjoy. The open floor plan and vaulted ceilings create a bright, spacious atmosphere, while expansive windows frame the stunning river views. The custom kitchen is finished with premium stone countertops, stainless steel appliances, and quality craftsmanship throughout. Step outside to the oversized composite deck, the perfect place to relax and take in spectacular sunsets, refreshing saltwater breezes, and the peaceful coastal setting. Shared water access directly across the street includes the right to pass and repass, making it easy to enjoy kayaking, paddleboarding, or simply spending time by the water.Tucked away on a private lane, the property also includes a new septic system to be installed by the seller prior to closing. The new sand filter system has been designed to preserve the backyard, allowing you to enjoy the outdoor space without compromising the property's layout or usability. A rare opportunity to own a like-new coastal cottage in one of South Westport's most desirable waterfront neighborhoods.

99 Sylvia Ln, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..
$749,000
3 Beds ⋅ 2 Baths ⋅ 73535124 MLS
Discover this well-built 3-bedroom, 1.5-bath ranch located on a private 2-acre lot in Westport. Spanning 2,286 square feet, the home features hardwood floors, a bright sunroom, and a living room with easy deck access. The property’s most distinctive feature is its massive garage capacity: an attached two-car garage and a detached eight-car workshop—a rare amenity ideal for collectors, hobbyists, or contractors. With updated kitchen appliances and a scenic, private setting, this property offers incredible potential for customization.

222 Blossom Road, Westport

Listing courtesy of Listing Agent: Bailey Holland from Listing Office: T L Holland Agency.
$725,000
3 Beds ⋅ 3 Baths ⋅ 73477315 MLS
Welcome to a barn find in Westport. Offering a single-family ranch up front, a 2-store 2nd structure in the middle of the property (current family living in) and a huge barn/garage. This property back in the 70/80's was licensed and used for horse boarding up to 30 stables, had a full retail store in the middle building. So much history. Property sits on 3.82acres. The family has decided to sell, and it will be sold as is.

343 Old Bedford Rd, Westport

Listing courtesy of Listing Agent: Steven Melo from Listing Office: Ponte & Associates Real Estate.
$699,000
2 Beds ⋅ 2 Baths ⋅ 73571697 MLS
Your Ultimate Coastal Retreat in South Westport! ?Tucked away at the end of a peaceful private way, this custom Cape/Saltbox sits on 3 pristine acres of total seclusion. This rare South Westport property features 2 bedrooms, 1.5 baths, and a private office, offering the perfect blend of coastal charm and flexible living. The expansive grounds include a versatile detached garage for storage or a workshop, plus incredible potential to build an ADU for guests or rental income. Located just minutes from the water, it is the ultimate private sanctuary you have been waiting for.

2 Monument Dr, Westport

Listing courtesy of Listing Agent: John P. Viveiros from Listing Office: Lamacchia Realty, Inc..
$663,900
4 Beds ⋅ 3 Baths ⋅ 73449463 MLS
Looking for MORE space in Westport—and a little help lowering your monthly payment? This could be the opportunity you've been waiting for! The SELLER IS OFFERING UP TO $10,000 TOWARD BUYER CLOSING COSTS, which may be used toward an interest-rate buy-down with an eligible loan program. Offered at $663,900, this home features 4 bedrooms, 2.5 baths, 2,182 sq. ft. of living space, two additional bonus rooms, a separate-entry home office, and a .80-acre lot. This is a home designed for buyers who need options. Work from home and want privacy? The separate-entry office keeps work and everyday living apart. Need a playroom, home gym, hobby room, media room, or additional flex space? Two bonus rooms give you the freedom to make the home work for your lifestyle. Hardwood, tile, and luxury vinyl plank flooring run throughout, while outside you'll find a generously sized yard with an above-ground pool and plenty of room to entertain, play, garden, or simply spread out. And here's a major bonus: a BRAND-NEW SEPTIC SYSTEM will be installed prior to closing, giving the next owner one less major expense to worry about. If you've been searching for more bedrooms, more usable space, and more flexibility in Westport, this home deserves another look.

128 Old Bedford Rd, Westport

Listing courtesy of Listing Agent: Team ROSO from Listing Office: RE/MAX Vantage.

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