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luxury real estate for sale Vineyard Haven, United States

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House with garden Vineyard Haven (United States)

A landmark property located on the very northernmost tip of Martha's Vineyard. 1005 Main Street is one of the ''Four Sisters'' - the four grandest and most historic homes in the distinguished West Chop neighborhood. The setting is unparalleled with a large private beach and 210-degree views so expensive that you can enjoy both sunrises and sunsets from the same deck. The views are extremely dynamic with ferries and fishing boats passing in the distance, and at night, the twinkling of lights from the mainland. There are 8 large bedrooms, 7 full baths, and a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been renovated between 1995 and 2022 with new insulation, roof, and HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the boardwalk down to it has been trod by many who have come to love this home and incomparable setting. With its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family. Owners may inquire about membership at the nearby West Chop Club, which offers a wide range of amenities.

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$6,000,000
469
9bedrooms
8bathrooms
land  3,359

By Wallace & Co. Sotheby's International Realty

30

House with garden Vineyard Haven (United States)

This meticulously renovated 1920s gem is nestled in the desirable West Chop area of Vineyard Haven, offering a perfect blend of historical charm and modern luxury. With deeded access to a pristine beach on Vineyard Sound, this exquisite residence is a seaside haven. Step inside to discover a spacious layout. The heart of the home is the gourmet kitchen, boasting custom cabinetry and high-end appliances. Entertain with ease in the open-concept living and dining areas, where upgraded systems and central A/C ensure year-round comfort. The second floor features a primary bedroom suite with a luxurious tile bath and soaking tub in addition to 2 guest bedrooms and an elegantly appointed guest bath with laundry. Every detail of this home has been thoughtfully considered, including a charming compass rose stained glass window, adding a touch of nautical flair. The finished lower level includes additional living space and a spacious bedroom. Step outside to the stunning mahogany rear deck overlooking a newly landscaped yard, ideal for entertaining and an outdoor shower. With easy access to Downtown Vineyard Haven and Vineyard Sound beaches, don’t miss the opportunity to own this exceptional property where timeless beauty meets contemporary living.

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$2,490,000
254
4bedrooms
3bathrooms
land  725

By Wallace & Co. Sotheby's International Realty

31

House with pool Vineyard Haven (United States)

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven’s most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also features a renovated garage with a finished second level, perfect for a creative studio. Inside, the home exudes warmth and elegance, with wide pine flooring, custom craftsmanship, and intricate wood detailing on the ceilings. The spacious living room, centered around a gas fireplace, is both inviting and stylish. The sunlit kitchen, equipped with top-of-the-line appliances and refined finishes, includes a cozy window seat that adds to its charm. The primary bedroom suite offers a serene retreat, complete with a private tile bath and access to a 2nd-floor deck. The three additional bedrooms are equally comfortable and well-appointed, providing ample space for guests. The finished lower level expands your living space further, ideal for a home theater, gym, or playroom. Spend your days soaking in this privacy that this tranquil abode provides, or take advantage of its ideal location to access the hustle and bustle of downtown Vineyard Haven where you can enjoy various galleries, shops, and fine dining. This location is also convenient to Owen Park Beach, West Chop and Mink Meadows Golf Club.

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$3,295,000
204
4bedrooms
3bathrooms
land  884

By Wallace & Co. Sotheby's International Realty

24

House Vineyard Haven (United States)

Welcome to this charming 3-bedroom home, ideally situated on the tranquil end of William Street, just steps from the vibrant heart of downtown Vineyard Haven. This inviting residence boasts a spacious primary suite conveniently located on the main level, offering ease and privacy. The open and airy layout seamlessly blends modern comfort with classic appeal, making it perfect for both relaxing and entertaining. Enjoy the serenity of your peaceful surroundings while being only a short stroll away from local shops, restaurants, and the picturesque harbor. Whether you're seeking a year-round residence or a serene retreat, this home offers the best of both worlds. Come see it today and experience the charm and convenience for yourself!

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$2,150,000
221
3bedrooms
3bathrooms
land  1,617

By Wallace & Co. Sotheby's International Realty

34
Video

House with garden Vineyard Haven (United States)

Welcome to your dream home in the exclusive Lower Makonikey Association, a serene enclave on Martha's Vineyard. This meticulously crafted 3,284 square-foot residence with a 3-car garage is a masterpiece of design and comfort, set on 3.21 acres of lush, tree-lined grounds accented by historic stone walls. Offering 4 spacious bedrooms and 4 elegantly appointed bathrooms, this home embraces the charm of island living. The main level features a flowing floor plan, ideal for both entertaining and everyday living, with a gourmet kitchen with a sun-filled breakfast nook, and butler’s pantry, dining room, and a spacious living room with a brick fireplace. A home office and laundry room finish the first floor which has beautiful hardwood floors throughout. Upstairs, the primary bedroom suite is beautifully appointed and features a spacious bathroom with double sinks, spa tub and shower. The bedrooms are generously sized, with ample natural light and stunning views of the surrounding landscape. The third level holds tremendous potential, offering the possibility to add 2 additional bedrooms, further enhancing the home's versatility. Outside, the back deck and expansive grounds provide a peaceful sanctuary, perfect for outdoor activities, gardening, or simply relaxing in nature's embrace. As a resident of the Lower Makonikey Association, you'll enjoy access to a private association beach on Vineyard Sound. This exceptional property is more than just a home; it's a lifestyle. Experience the perfect blend of privacy, elegance, and community in one of Martha's Vineyard's most sought-after neighborhoods.

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$3,195,000
305
4bedrooms
4bathrooms
land  1.3ha

By Wallace & Co. Sotheby's International Realty

41

House with garden Vineyard Haven (United States)

Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen with top-of-the-line appliances and custom butcher block island. Attached to the kitchen is a welcoming dining room and wet-bar and a screened porch with garden views. The multiple spacious living areas are flooded with natural light and fireplaces perfect for both entertaining and everyday living. The second floor features 3 beautifully appointed bedrooms with 3 updated tile baths. Additionally, a serene sitting room awaits, complete with built-in bookshelves, creating the perfect place for relaxation or study. Venture to the third level and discover a hidden retreat—a charming bedroom offering privacy distant water views. Outside, there is an expansive yard, a rare find in-town, offering ample space for outdoor gatherings and gardening. The detached 2-story 1-bedroom barn-style guest house beckons, a charming retreat with its own private back deck. From the elegant facade to the landscaped grounds with beautiful perennial gardens, every aspect of this property reflects a rich history and a timeless appeal. The perfect in-town location with easy access to Downtown Vineyard Haven restaurants, shops, beaches and ferry. Excellent rental history.

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$3,250,000
349
5bedrooms
5bathrooms
land  1,538

By Wallace & Co. Sotheby's International Realty

127 listings near Vineyard Haven

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11

Land Oak Bluffs (United States)

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the possibilities are endless.

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$530,000
931

By Wallace & Co. Sotheby's International Realty

Nearby
11

Land Oak Bluffs (United States)

Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

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$595,000
1,335

By Wallace & Co. Sotheby's International Realty

Nearby
50
Video

House with garden Oak Bluffs (United States)

Welcome to your dream retreat in Oak Bluffs—a magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home; it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

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$13,200,000
759
8bedrooms
9bathrooms
land  2,590

By Wallace & Co. Sotheby's International Realty

Nearby
42
Video

House with garden West Tisbury (United States)

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main house was recently renovated by a top local contractor and the result is a rustic Vineyard vibe with a sophisticated twist. The cozy and comfortable kitchen and sitting room areas lead to the dramatic Great Room on the north end of the house - the 600 square foot space with its 26’-high ceilings is bathed in light thanks to the banks of windows and French doors. There are two bedroom suites upstairs with views of the main pond, one of them with a sundeck. The third floor loft area has also been used as a bedroom and is the perfect spot to accommodate younger members of the family and their friends. The detached two-story guest quarters continue the Vineyard country chic theme with a delightful bedroom with veranda overlooking a separate area of the property from the main house. In addition to the main house and detached guest bedroom, there is a barn with a large finished room and loft as well as a secluded writing studio. A new garage completes the compound. Note: Four-bedroom septic in place. Property currently has 3 bedrooms plus 1 loft sleeping space.

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$2,550,000
277
4bedrooms
3bathrooms
land  1.6ha

By Wallace & Co. Sotheby's International Realty

Nearby
29

House with garden Edgartown (United States)

Experience the serene beauty of this 4-bedroom, 3.5-bathroom pond-front home in the Sengekontacket Community. Nestled on a hillside overlooking a freshwater pond, this home offers the perfect island retreat. Lush garden beds and wildflowers greet you as you make your way to the pond, where you can enjoy swimming or paddling. The well-appointed kitchen seamlessly connects to the dining room and deck, all with stunning pond views. The first-floor primary bedroom features a private bath and a spacious closet, with sliding doors opening to the back deck. Upstairs, another ensuite bedroom awaits, along with an open loft ideal for an office or game room. The finished lower level opens to a bluestone patio with an outdoor shower and includes two bedrooms, a full bathroom, and a large laundry area. Residents of the Sengekontacket Community can take advantage of access to the dock and kayak storage on Sengekontacket Pond, as well as tennis/pickleball courts and a community clubhouse, perfect for hosting small events. Fully furnished, including kayaks and electric bikes, this property is ideal for a peaceful retreat, an investment, or both. All you need is your toothbrush!

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$2,950,000
280
4bedrooms
4bathrooms
land  2,752

By Wallace & Co. Sotheby's International Realty

Nearby
Contract pending
12

House with garden West Tisbury (United States)

Lamberts Cove Beach access, first and second floor water views, and a warm and inviting home in a private West Tisbury location - that is what is on offer here. The home was recently upgraded with a new kitchen and bathrooms. The primary bedroom suite has even better views than those from the first floor. The walkout lower level is a two bedroom suite with full bath, sitting area, kitchenette, and private entrance that leads to a beautiful sitting area beside a fenced-in vegetable garden and flower-cutting garden. In addition to a deck and backyard patio, there is also a porch in the front of the house. There is a climate-controlled garage that is currently a complete workshop with an upstairs that can be converted into a detached bedroom if one of the bedrooms in the main house is decommissioned.

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$2,225,000
232
4bedrooms
3bathrooms
land  7,284

By Wallace & Co. Sotheby's International Realty

Nearby
20

Property Oak Bluffs (United States)

This 4-bedroom home is located within the desirable Hidden Cove Association, a 65-acre community of well-tended homes with direct water access to Sengekontacket Pond, State Beach, and Nantucket Sound. The property has conservation land behind and beside it. You truly feel like you are on the Vineyard when you make your way down the boardwalk through the marsh to the secluded area with private boat dockage and a place to keep your kayaks and other watercraft. There are also walking trails and tennis. All this is within the outskirts of Oak Bluffs with easy access to other towns.

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$1,550,000
243
4bedrooms
4bathrooms
land  1,619

By Wallace & Co. Sotheby's International Realty

Nearby
21

House with garden Edgartown (United States)

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.

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$1,725,000
155
4bedrooms
2bathrooms
land  2,064

By Wallace & Co. Sotheby's International Realty

Nearby
38

House with garden Edgartown (United States)

A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and a kitchen with doors leading out to a welcoming screened porch. This home features a primary bedroom suite and a guest bedroom suite on the first level. Two additional guest bedrooms complete second floor. The exclusive Boldwater Association offers tennis courts, a boat landing on the Edgartown Great Pond, and a private South Shore sandy Atlantic Ocean beach. The Edgartown Great Pond is great for kayaking, paddling and boating.

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$4,150,000
330
4bedrooms
4bathrooms
land  3.5ha

By Wallace & Co. Sotheby's International Realty

Nearby
Contract pending
50
Video
3D visit

House with garden Falmouth (United States)

Welcome to this magnificent 5,051 sq. ft. residence in the highly sought-after Belvidere Plains area of Falmouth. This 4-bedroom home exudes luxury with its exquisite finishes, including soaring 9-foot-plus ceilings, beautiful built-in cabinetry, elegant transom windows, wide plank oak flooring and exquisite tile work throughout. The expansive open floor plan flows seamlessly, perfect for both daily living and grand entertaining and seamlessly blends the interior and exterior living spaces. At the heart of this meticulously designed home is a Chef's kitchen, featuring a commercial Subzero refrigerator, Wolf appliances, custom hood, Quartzite countertops, an expansive Island and custom cabinets. The family room's coffered shiplap ceiling and inviting gas fireplace adds a touch of grandeur. The first-floor primary suite is a true retreat, featuring a spa-like bath with a walk-in shower, soaking tub, beautiful tile work and radiant heated floors. Finishing off the main level is a light-filled office with an array of built-in cabinets offering a quiet and convenient space for remote work. Upstairs, you'll find three generously sized bedrooms, two full bathrooms and a large second family room, offering additional space for play, games and relaxation. A large roof deck provides a nice place to escape to enjoy a cup of coffee in the morning or capture a sunset at the close of the day while taking in the surrounding scenic views. Completing the home is a private suite with its own staircase and full bath, ideal for guests, extended family, or use as a secondary office. Outdoors, enjoy a serene private backyard setting featuring an exquisite covered granite patio with built-in heaters, a firepit area and a dedicated garden space with four above ground planting areas, all surrounded by natural fencing that blends into the landscape. The property is equipped with a full-house on-demand gas generator and an oversized two car garage. Perfectly situated between downtown Falmouth Village, Surf Drive Beach and Falmouth Harbor, this property is your gateway to a piece of heaven on Cape Cod. Grab your towel and suntan lotion and spend the day at Surf Drive Beach, or ride your bicycle along the Shining Sea Bikeway to Woods Hole and beyond. Imagine hosting barbecues, playing cornhole, or even adding a refreshing pool to create your own private oasis. With convenient access to the harbor, take your boat or one of the nearby ferries and spend the day exploring Martha's Vineyard or take a sunset cruise on the Liberte sailboat. Whether this will be your full-time residence or summer escape, this home is ready for new owners to embrace the magical feel of Cape Cod.

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$3,575,000
4bedrooms
5bathrooms
land  2,185

By Sotheby's International Realty - Falmouth Brokerage

Nearby
25
Video

House Edgartown (United States)

Located within the heart of the highly sought-after historic district of Edgartown, this 4-bedroom residence on South Summer Street offers a unique blend of timeless elegance and historical detail. Built in 1780, this home stands as a testament to Edgartown's rich architectural heritage with its classic New England design, complete with a white picket fence. Enter through the welcoming foyer, which leads to a spacious living room with original wide plank hardwood floors and classic moldings. The living room and formal dining room feature fireplaces which create an inviting space for gatherings and entertaining. Primary bedroom suites can be found on both levels of this home. The property includes coveted off-street parking and a 1 car garage. Enjoy the convenience of living in the heart of downtown Edgartown. South Summer Street is a short distance to boutique shops, restaurants, art galleries, and the iconic Edgartown Harbor. This property represents a unique opportunity for those with a vision for restoration.

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$3,200,000
207
4bedrooms
3bathrooms
land  526

By Wallace & Co. Sotheby's International Realty

Nearby
31

Apartment with pool Falmouth (United States)

Highly sought after Townhome in MOVE IN condition is perfectly situated in Falmouth Heights. The Boatyard Condominiums offer professional landscaped grounds, well maintained buildings and view of Falmouth Harbor. This 32-unit complex is well located within a short distance to stores, restaurants the Heights Beach and ferry to Martha's Vineyard. This 2bd, 2.5bath unit offers open flr plan inside, has spacious deck with views of harbor, and one of the few that have an attached garage with access from within the unit. Below are 2 bedrooms, each with ensuite bathroom. Association heated swimming pool with gate access to Harbor. All information to be verified by buyer or buyers agent. Seller reserves the right to accept any offer at any time.

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$1,099,000
2bedrooms
3bathrooms

By Sotheby's International Realty - Falmouth Brokerage

Nearby
50
Video

House Falmouth (United States)

This classic Falmouth Heights beach house just behind the Heights ballfield has been thoroughly enjoyed by the family for the past 31 years. The main level offers 2 bedrooms, full bath, open living & dining rooms with a galley kitchen and a spacious attached sun room. The walk out lower level has another bedroom, home office, family room, full bath, laundry & kitchen set up minus a stove. Low maintenance yard allows for more time at the beach and all the other Heights amenities such as restaurants, shopping, biking along the beach & the Island Queen ferry to the Vineyard. Passing 3 Br. septic report in hand. Come see it while it is still available. You must see it to feel it.

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$979,000
3bedrooms
2bathrooms
land  526

By Sotheby's International Realty - Falmouth Brokerage

Nearby
21

House with pool and garden Edgartown (United States)

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. Perfect for family living or hosting guests, this home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

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$17,500,000
448
6bedrooms
9bathrooms
land  1,214

By Wallace & Co. Sotheby's International Realty

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