luxury houses with pool for sale West Tisbury, United States

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residencean architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleballoffering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today. Off Edgartown West Tisbury Road via Pohoganot Road.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.

Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment. This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and offers an extraordinary compound featuring 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology. Beautiful oak floors run throughout the home, complemented by sophisticated hardware, premium appliances, and walls tastefully finished with nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar is equipped with an ice maker and refrigerated drawers and can easily be converted into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, providing both privacy and balance. The main floor also includes an inviting secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom thoughtfully designed for effortless island living. Upstairs a spectacular primary suite serves as a retreat, complete with private balcony and a bonus two full spa-inspired baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above the garage offers a private guest suite with a balcony overlooking the pool. The outdoor setting is unparalleled for in-town living. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and an exceptional cabana with kitchenette, half bath, laundry, heating and air conditioning. This Edgartown estate offers privacy, scale, and sophistication rarely found within steps of Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

Tucked within the desirable Greengate community, this 4-bedroom, 4-bath shingle-style home is designed for easy Cape Cod living and memorable gatherings. Set on nearly an acre of privacy, the property is wrapped in lush, mature plantings that create a sense of retreat the moment you arrive. At its heart lies the showpiece: a sparkling 50 foot gunite pool and expansive patio. This is where life slows and memories are made--sun drenched summer afternoons, dinners under the stars, and lively celebrations with family and friends. Inside, the inviting layout includes two first-floor bedrooms, open and comfortable living and dining areas, and seamless access to the pool and patio. Upstairs, two additional bedrooms offer space for family and visiting friends, while the partially finished lower level extends the possibilities--whether it's a game room, creative studio, or space for overflow guests. From this location, everyday living feels like a getaway. Bike the neighborhood Shining Sea Bikeway, explore the charm of Woods Hole, wander through vibrant downtown Falmouth, or catch a ferry to Martha's Vineyard on a whim--all just moments away. This is a home where outdoor living meets coastal lifestyle, a true oasis awaiting new owners to experience the best that Falmouth has to offer.

Welcome to effortless Cape Cod living in Seacoast Shores! Completely reimagined inside and out, this beautifully renovated 3-bedroom, 2-bath home combines the ease of one-level living with the relaxed coastal lifestyle buyers come to Falmouth to find. A welcoming farmer's porch sets the tone, while the light-filled interior offers a fresh, coastal feel and an easy flow for everyday living and entertaining. Thoughtful updates throughout make this a truly turnkey opportunity—simply arrive and begin enjoying your Cape escape. Set in the desirable Seacoast Shores community, where days are meant to be spent on the water and evenings enjoyed outdoors, this property offers an appealing option for a year-round residence, summer getaway, or investment. At $950,000, 245 Edgewater Drive East presents an opportunity to own a completely renovated Cape Cod home without taking on the time, expense, and uncertainty of a renovation. Your Falmouth lifestyle is ready and waiting.

Welcome to the Captain Weston Swift House, built circa 1800 and now listed on the National Register of Historic Places. The impeccably renovated Swift House is a rare blend of history and modern comfort. Previously operated as the renowned Coppage Inn and now a private residence, the 4,456 sq. The main house features 5 bedrooms (3 en suites, including a primary bath with a steam shower), 6 fireplaces, wood floors, custom built-ins, and myriad architectural accents. Modern updates include a renovated kitchen, marble/tile bathrooms, and elegant lighting. Designed for entertaining and everyday living, the layout offers a sun-filled living room, formal dining room, and patios overlooking a private acre of landscaped grounds. A brick courtyard, a bluestone patio with a pergola, and a large cedar wood deck enhance outdoor living. The centerpiece of the home is an indoor, heated, saltwater swimming pool for year-round enjoyment. The pool house holds 2 bathrooms; a laundry; and a hot rocks sauna. The pool house is 1,984 additional sq. ft. and is not included in the total square footage. The Carriage House includes 1,178 sq ft of finished space with a 2-bedroom, 1-bath apartment (dedicated septic), an oversized heated garage/workshop, and renovated studio/office/living space with its own full bathroom. Rich in character and updated for today's lifestyle, this legacy property is truly one of a kind in the heart of Cape Cod. Part of the Waquoit Historic District. 0.5 miles to Waquoit Public Landing.

A truly exceptional estate offering unparalleled luxury and resort-style living. This custom-built, 3-bedroom home boasts a captivating open-concept floor plan highlighted by soaring vaulted ceilings, gleaming hardwood floors, creating a bright and expansive atmosphere. The exquisite primary suite offers a private sanctuary on the 1st level as well as 2 other large, carpeted bedrooms both with ensuite bath. Beyond the main house, discover a 3-car garage with a private, fully appointed guest suite above, ideal for visitors or extended family. Step outside to your personal oasis, featuring a heated in-ground pool and bubbling hot tub, all nestled within a meticulously landscaped .7-acre lot adorned with charming stone walls and mature planting for extra privacy. A separate pool house provides ultimate convenience, complete with a kitchenette, full bath, laundry & AC. For the avid golfer or entertainer, the lower level reveals a professional 9-hole putt-putt course offering endless enjoyment. Adjacent to this unique amenity, a dedicated TV/ping pong playroom provides additional recreation space. Schedule your private tour today to experience this remarkable find. Total square footage includes lower level, Guest Suite over garage and pool house.

Welcome to one of New Seabury's most extraordinary waterfront offerings. Perfectly positioned on a private, oversized lot, 8 Bowsprit Point delivers the ultimate Cape Cod lifestyle with a coveted 50-foot, shore-powered deep-water dock offering direct access to Nantucket Sound. Whether you're setting out for a day on the water or returning for sunset cocktails, boating has never been more effortless. Designed for exceptional indoor-outdoor living, the expansive grounds showcase a heated gunite pool, spa, generous entertaining patios, and sprawling lawn surrounded by mature landscaping for remarkable privacy. Inside, more than 6,000 square feet have been thoughtfully reimagined with a spacious, open layout that captures panoramic water views through soaring walls of glass, creating an elegant yet comfortable retreat for everyday living and grand entertaining alike. Nestled on one of New Seabury's most desirable streets, this is a rare opportunity to own a legacy waterfront estate where luxury, privacy, recreation, and location come together in one unforgettable property. Opportunities like this are exceptionally rare--experience coastal living at its finest.

Desirable Deer Crossing Community - This lovely townhome could be your perfect year round residence or Cape Cod retreat! The condominium features an open floor plan & beautifully renovated kitchen w/ quality cabinetry, granite counters, stainless appliances & garden window. Crown molding continues into the dining area & fireplaced living room w/ slider to your composite deck & private wooded yard. A 1/2 bath competes the 1st floor. Luxury vinyl plank flooring & carpeting continue to the 2nd level w/ 2 generous sized bedrooms & full bath. In the lower level there's approximately 500 SF of bonus area which just needs flooring for additional finished space. Deer Crossing Amenities include a spacious Clubhouse, pool, tennis/pickleball courts, walking trails and landscaped green space. Conveniently located to South Cape Beach, Mashpee Commons & South Cape Village shops & restaurants. Pets: 1 dog 50# breed restricted or 2 cats. Rentals ok w/ minimum 1 yr. lease. Refundable deposit of 2 mos. condo fee to HOA due at closing. Buyers & Agents to verify all information contained herein.