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$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.

$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..

$1,950,000
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.

$550,000
3 Beds 2 Baths 73565178 MLS
**Welcome to 5 Rock St in Westport, MA!** This beautifully updated 3-bedroom, 2-full-bath home offers a wonderful opportunity to put down roots in a welcoming community. The thoughtfully designed first floor features an updated kitchen with granite countertops, tile backsplash, and stainless-steel appliances, opening seamlessly to the dining and living areas—perfect for everyday living and entertaining. Two bedrooms, two full bathrooms and laundry are conveniently located on the first floor, while a spacious third bedroom is situated on the second floor. New hardwood flooring, recessed lighting throughout, fenced in back yard and a brand-new roof with new gutters add to the home's comfort and appeal. The true standout feature is the impressive **detached garage, offering nearly 1,800 square feet of versatile space**. Whether you're looking for rental income (currently leased for $1200 per month) or secure car storage, boat storage, a workshop, hobby space, or additional room for your business or projects, the possibilities are endless. The building also includes a dedicated office area, half bath, and loft storage. A unique property offering flexible living space and an exceptional detached building with rental income to offset the mortgage—come see all that 5 Rock St has to offer!

5 Rock St, Westport

Listing courtesy of Listing Agent: John Ray from Listing Office: Cameron Real Estate Group.

$475,000
73563952 MLS
Welcome to Cory Ridge Estates, a new subdivision located off Cornell Road in South Westport. With only one lot remaining, Lot 3—the middle lot—is a rare opportunity to build your dream home in a beautiful, private setting.This 1.41-acre lot has been perc tested, with utilities already run to the lot, making it ready for your building plans. The property retains beautiful old stone walls and is conveniently located near Westport Conservation Land Trust land, offering easy access to protected open space and the natural beauty of South Westport.The new road is in the final stages of construction and will be a gravel road with underground utilities. Natural gas is not available.A great opportunity to build in a newly created subdivision while enjoying the character, privacy, and open space that make South Westport so desirable.

Lot 3 Thomas Cory Ln, Westport

Listing courtesy of Listing Agent: Nicole Plante from Listing Office: Even Keel Realty, Inc..

$519,900
2 Beds 1 Baths 73562773 MLS
This charming ranch home offers the ideal combination of recent updates, including a totally new bath with high-end fixtures. This exceptional property delivers a peaceful retreat with serene pond views, a private back patio, and a back lawn with extensive bird and wildlife activity. Perfect for anyone seeking a comfortable, uncomplicated lifestyle. Newly refinished hardwood floors flow beautifully throughout the main level, leading into an expanded primary bedroom. The home features a completely updated bathroom finished with high-end fixtures, brand-new ceramic tile flooring, and a convenient, modern walk-in shower. Everyday chores are made effortless by a smart dual-laundry setup, boasting a small washer on the first floor for quick daily loads alongside large-capacity machines in the lower level. A brand-new roof and a modern, high-efficiency heating system provide immediate peace of mind and keep utility costs low and hassle-free ownership on a lot that is uniquely private for the area.

292 Tickle Road, Westport

Listing courtesy of Listing Agent: Laurie M. Ammann from Listing Office: Milbury and Company.

$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.

$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..

$475,000
1 Beds 1 Baths 73555286 MLS
Make lasting memories in Westport’s coveted coastal beach community, just minutes from Horseneck Beach and Gooseberry Island. Located near the end of a quiet road, this charming summer cottage offers breathtaking, unobstructed views of East Beach and the surrounding islands. Enjoy beautiful sunrises, colorful sunsets and refreshing coastal breezes from the spacious rooftop deck, designed to maximize the spectacular water views. The views must be seen to be appreciated. Just a short walk to East Beach, Bayside Restaurant and the scenic Allens Pond walking trails—perfect for birdwatching and enjoying local wildlife. This summer cottage currently offers one bedroom with potential to re design and make it your own, it's larger than it appears. Three garden sheds provide additional storage. A wonderful opportunity to create your very own Westport beach retreat!

32 First St., Westport

Listing courtesy of Listing Agent: Karen Ann Martin from Listing Office: Safe Harbor Realty.

$599,000
73554092 MLS
Positioned on busy Route 6, this 2.3-acre with a 36 Car Dealer License,with plenty of room for more inventory this commercial property presents an exceptional opportunity for automotive and a wide range of commercial uses. The site features a finished parking area and a two-bay, garage, making it ideally suited for used vehicle sales, fleet operations, equipment rental, service businesses, contractor storage, or other multi-vehicle enterprises.With outstanding visibility, high daily traffic counts, and ample on-site parking, the property offers immediate functionality while also providing significant long-term upside.Whether you're seeking a turnkey automotive location or a strategic investment with redevelopment potential, this property offers the rare combination of existing infrastructure, prominent exposure, and the space to bring your vision to life. Opportunities of this size and versatility along the Route 6 corridor are increasingly difficult to find.

575 State Rd, Westport

Listing courtesy of Listing Agent: Noble Vincent from Listing Office: Coastal Realty.

$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..

$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.

$2,275,000
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..

$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..

$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.

$1,249,000
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.

$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..

$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.

$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.

$595,000
73532400 MLS
Rare opportunity to own approximately 10 acres in beautiful Westport. This unique parcel offers the potential for a single-family Maybe you envision a Luxury style home or always wanted to homestead while maintaining the privacy and natural beauty that make Westport so desirable. A perc test has been completed, and Planning Board determinations regarding access and frontage are available. The property features a blend of upland and wetland areas, creating a peaceful setting with abundant wildlife and natural surroundings. Conveniently located near beaches, farmland, local shopping, and major routes, this property offers perfect balance of country living and accessibility. Perc test documentation available. Planning Board letter on file regarding Mellos way as a qualifying way under the Westport Zoning Bylaw. Property believed to support one single-family residence subject to all necessary approvals and permits. Buyer responsible for verification of all information and intended use.

218 American Legion Hwy, Westport

Listing courtesy of Listing Agent: Sheri Francis from Listing Office: Bold Real Estate Inc..

$375,000
2 Beds 1 Baths 73531536 MLS
NEW PRICE - DIAMOND IN THE ROUGH - Beautiful flat wooded acre lot with water views of South Watuppa Pond improved with a 1,048 Sq ft Bungalow. This quaint home features 2 bedrooms, a cozy kitchen, sunny dining room with corner windows, a lovely family room with cathedral ceilings and a beautiful floor to ceiling stone fireplace. The sun room features flag stone flooring and ample windows. This home is in need of updating. But could be amazing for year round living or seasonal living. Home is currently serviced by a cesspool. And a private well. Home to be sold in AS IS Condition. Buyer responsible for all improvements to septic and home after closing. This is an Estate Sale. Property is subject to the personal representative obtaining a License to Sell from the Bristol County Probate Court prior to closing. Seller has never lived at the property and has no sellers disclosure.

217BB Tickle Rd, Westport

Listing courtesy of Listing Agent: from Listing Office: Costello Realty.

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