In the heart of Acoaxet, tucked along a private lane that follows the eastern shore of Richmond Pond, Water View Haven enjoys a commanding southwest orientation with sweeping UNOBSTRUCTED views across Richmond Pond, the barrier beach, and out to the Atlantic Ocean. Designed by Yankee Barn and constructed in 2020 to exceptional standards, this Post and Beam home blends timeless coastal design with

Deborah Ladd Compass

Waterfront home on Stonewall Pond. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark’s most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort. The interior

Alyssa Halisky Wallace & Co. Sotheby's

This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

Brenda Galligan Karen M. Overtoom R.E.

Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

Rebecca V Conroy Conroy & Company R.E., Inc.

This iconic home in Westport Harbor was built in 1770. It boasts stunning views of the ocean and Richmond pond. The property features 4 bedrooms, with a primary suite conveniently located on the first floor. The eat in kitchen is perfect for family gatherings and the home is situated on a spacious 2.43 acre lot. Additionally there is a large barn on the property, offering plenty of potential for

Jennifer Silverman Compass

Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

Natalie Conroy Conroy & Company R.E., Inc.

WESTPORT HARBOR - TWO HOME COMPOUND Located in one of Westport's most sought-after areas, this stunning shingle style 3 BR home along with this sweet 2 BR colonial is a rare offering. Strategicaly placed to maximize waterviews, each property feels connected yet each has their own solar panels, well, septic system, and yard where landscaping creates a sense of separation and privacy. Offering

OnPoint Team Residential Properties Li Residential Properties Ltd.

Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

Rebecca V Conroy Conroy & Company R.E., Inc.

This fully furnished 4-bedroom, 3.5-bath turnkey home sits on 2.7 acres of oceanfront property in Nonquitt, a historic gated community. With room to expand, this home blends coastal charm with modern comfort. The main level features a primary en-suite bedroom, a sleek kitchen/dining area, and a sunlit living room with a wood-burning fireplace. Upstairs, there’s a cozy den, laundry, and three

Betsy Lawrence LandVest, Inc.

12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

Tina Palmer Conroy & Company R.E., Inc.

Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

Stephanie Roache Donnelly + Co.

Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

Cheri Mason Landvest MV

Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

Patty Kendall Kendall & Kendall

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

Thomas Wallace Wallace & Co. Sotheby's International Realty

Rarely available, Seaside East free-standing home with dazzling water views and country club living. Entering this home you find yourself in an expansive fireplaced living room with soaring ceilings and hardwood floors. The spacious sunroom is wrapped in sliding glass doors that open to the wrap-around deck. The kitchen, while vintage, is large and bright, and opens to adjacent dining area with

William Milbury Milbury and Company

South Dartmouth-This Extraordinary Williamsburg-inspired cape is nestled on 3 acres of an enchanting home site, framed by a picturesque spring fed pond. A peaceful retreat, accessed through a private community, this property is surrounded by natural beauty & tranquility, yet within minutes to Round Hill Beach and Padanaram Village. This Iconic home was designed w/symmetry & balance in mind,

Fatima Simas Anne Whiting Real Estate

You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around

Russell Maloney Russell Maloney Real Estate

11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of

Deb Hancock Hancock Real Estate

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

Julianna Flanders Flanders Real Estate

Welcome to Underwood Farm in beautiful Westport! This impeccably maintained 1-bedroom, 1.5-bath condo blends style, comfort, and convenience in one of the area's most sought-after communities. The open-concept design features gleaming hardwood floors, soaring ceilings, and a seamless flow through the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The modern

Jim Sabra Equity Real Estate

Enjoy Privacy & Tranquility at Unit 1 in Desirable Underwood Farm Community in Westport .This Lovely Townhouse Style 1 Bedroom Condo Features Wood Flooring , High Ceilings,Recessed lighting , SS Appliances & A stylish Kitchen With plenty of Counter Space & Openness. Private Rear Deck to Enjoy Your Coffee and Entertaining.The Spacious 1st Floor Bedroom Is Adjacent to the Full Bath with an

Celeste Fournier Blu Sky Real Estate

Welcome to 99 Sylvia Lane in South Westport - Fully renovated cottage with amazing westerly views of the East Branch of the Westport River. Cottage was gutted to studs in 2024. New plumbing, heating, insulation, windows, siding and more. New interior layout with use of every little inch. Vaulted ceiling and open floor plan. Views all around. Amazing kitchen design with high end granite and

Nicole Plante Even Keel Realty, Inc.

WESTPORT BEACH COTTAGE RETREAT Fully renovated cottage nestled between conservation lands, just minutes from East Beach and Horseneck Beach, with Cherry & Webb Beach nearby. The property includes valuable deeded beach access, making this perfect for nature lovers and beachgoers. Enjoy coastal views from the spacious deck and porch. The interior blends modern comfort with seaside charm, creating a

Jonathan Minerick homecoin.com

Located in Round Hill —one of South Dartmouth’s most iconic waterfront communities—this stunning two-level Mansion condominium offers the unique opportunity to embrace elevated coastal living. With 2 bedrooms, 2 full baths and a 2300+/- sq ft footprint, this residence showcases lofty ceilings, a bright open floor plan on both levels, and a sleek, move-in-ready interior with coastal contemporary

Team MCM Gibson Sotheby's International Realty

Custom built Red Oak Post and Beam country home, in the style of an Old English cottage mansion. The many unique and attractive features are sure to delight the most discerning buyer. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home. Throughout, this intriguing, creatively designed home, you will notice the high quality and attention to detail.

Elaine Vanderhoop Beachcombers of MV

WATERFRONT - Welcome to 1518 Drift Road. Tucked along the banks of the east branch of the Westport River, this three bedroom cottage was completely renovated with a modern country charm: beadboard walls, pine floors, fieldstone fireplace, and an open chef's kitchen. The former garage was transformed into an artist studio which can provide many options. Even though it is ONE OF THREE PROPERTIES

OnPoint Team Residential Properties Li Residential Properties Ltd.

Welcome to 37 Glen Road, a spectacular waterfront retreat set atop a private peninsula with sweeping views of the Westport River. This picturesque 5,000+ sq ft home is sited on 11.3 acres of rolling lawns, mature woods, landscaped gardens and features a pond, stream, and private dock. Thoughtfully renovated in 2010, the expanded one-level Cape features 3 bedrooms, a timeless kitchen and scullery,

Team MCM Gibson Sotheby's International Realty

This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

Meg Bodnar Tea Lane Associates