Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

Thomas Wallace Wallace & Co. Sotheby's

Beautifully maintained 3,644 SF, 4-bedroom, 2.5-bath Cape located in a highly sought-after Drift Road location. Just minutes from area beaches, shops, and local amenities, this home is tucked away on a private way, with a beautifully manicured 1.9-acre lot. A desirable open floor plan is appointed with hardwood floors, a custom cherry kitchen, granite countertops, and a spacious island that flows

Jim Sabra Equity Real Estate

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

Jessie Holtham Wallace & Co. Sotheby's International Realty

Three-bedroom, 2.5-bath post-modern shingle-style home set on nearly 1.5 acres, offering the convenience of first-floor living. The main level features hardwood floors, an eat-in kitchen with sliders to the deck, formal living and dining rooms, and a laundry/mudroom just off the attached two-car garage. The lower level provides exceptional flexibility with stone tile flooring, a spacious

Sarah Meehan Milbury and Company

New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

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

Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

Jennifer O'hanlon Compass LLC

The Dylan 2.0" South Dartmouth, Luxury Living at its finest! Experience the epitome of privacy, peace and tranquility, while living along the Slocum River! Breathtaking water views compliment this exquisitely built new construction home. This is the perfect home to entertain family and friends! A true executive masterpiece featuring an open concept floor plan and an abundance of custom details!

Scott Almeida Keller Williams South Watuppa

Tucked away from the street, this one-of-a-kind, waterfront, property offers a stylish home in a serene setting with peaceful river views. Beautifully landscaped gardens, an Italian-inspired courtyard, and a riverside patio create a truly special retreat. A separate workshop/garage offers guesthouse potential. With artistic flair, quality materials, and a unique “traditional contemporary” design,

Kathryn Salmon Equity Real Estate

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

Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting.Recent updates include a new roof, siding, and HVAC system, ensuring

Stacy Ickes Donnelly + Co

Enjoy the best of rural charm and coastal convenience in this well maintained single-family home offering easy one-level living in a peaceful country setting. This charming ranch style home offers three bedrooms, two baths, an updated kitchen, living room, dining area and laundry room. The finished lower level provides excellent extra space for a playroom, guest area, exercise room or a hobby

Liz Kinnane Mott & Chace Sotheby's Intl.

New Price: The Pound Keeper’s Cottage (c. 1775), in the village of Russells Mills, South Dartmouth, Massachusetts, is for sale – the second time since 1958. This country house retreat, cosseted by meadow and woodland, is complemented by the coastal estates, conservation lands, and historic farms, which are so evocative of the New England landscape. Its proximity to Boston, Providence, and NYC

The Mathew J Arruda Group Compass

Exceptionally located on 1.8 acres along the West Branch of the Westport River, this well-maintained four-bedroom, three-bath home offers hardwood floors throughout and effortless waterfront living. Nearly every room opens via sliders to a waterside mahogany deck overlooking the river.The main level features a first-floor primary en suite, two guest bedrooms, a full bath, and living and dining

Sarah Meehan Milbury and Company

Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation. Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

Patrick McCarthy Grace Hagerty Real Estate Inc

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.

This elegant coastal colonial presides on nearly one acre of land in highly desirable Acoaxet! Dramatic two-story foyer ushers you into the heart of the home, which is a spectacular fireplaced living room with built ins, and French doors to the spacious rear deck. Open dining area extends into a chef's kitchen, with upgraded quartz countertops and stainless steel appliances. Adjacent to the

William Milbury Milbury and Company

Great opportunity to live in a sought-after neighborhood of South Dartmouth. This home was thoughtfully built by the current owners and sits on almost an acre of land with a generous side yard offering excellent potential for an ADU or other possibilities. Home features 3 bedrooms, an eat-in kitchen, dining room with french doors that opens up into the spacious living room with fireplace.

Ronald Oliveira RE/MAX Vantage

Experience the pinnacle of coastal sophistication in South Dartmouth's most coveted gated enclave. This shingled contemporary masterpiece, custom-crafted by Fisher and Rocha and featured in Builder/Architect Boston magazine, rests on a private acre abutting the 3rd Fairway.A dramatic foyer leads to soaring cathedral ceilings and a striking fireplace. Transition to a screened porch with

Anastasia Kaufman REMAX Revolution

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

Tom Wallace

Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm--a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

Alyssa Halisky Wallace & Co. Sotheby's International Realty

Set on over 6.75 private acres, built in 2008, this custom brick-front Georgian Colonial offers estate-like curb appeal and high quality construction. Boasting over 4,500 sq ft of sun-filled living space, this 12-room home features 4+ bedrooms & 4.5 luxurious baths. A grand two-story foyer opens to elegant formal spaces and a stunning sunken family room w/ vaulted ceilings, fireplace, & expansive

Brian Balestracci Milestone Realty, Inc.

Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

Russell Maloney Russell Maloney Real Estate