Luxury homes for sale & real estate in Vineyard Haven, MA

Luxury Home for sale in Vineyard Haven, MA:

These twin houses built in 1909 in the historic subdivision of East Chop Highlands offer most of the modern conveniences of today with the old world charm and decorative craftmanship style. Both houses are separately deeded so that they could be owned separately or together. These houses are fully winterized and have been occupied for the past 30 years. Each house has 2 bedrooms with bathrooms en suite. An open floor plan with a kitchen, dining area, and living room #12 has a bonus room presently used as an office. Both houses have 2 heating systems, both forced hot-air central heat, and air pump heating and air conditioning for energy efficiency. One is heated with oil and the other with p

Luxury Home for sale in Vineyard Haven, MA:

Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just . 3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations. Septic is a cesspool and will need to be upgr

Luxury Home for sale in Vineyard Haven, MA:

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 to the back deck. Upstairs, another ensuite bedroom awaits, along with an open loft ideal for an office or a game room. The finished lower level opens to a bluestone pa

Luxury Home for sale in Vineyard Haven, MA:

* * Best and final offers due by Monday November 4 by 5:00 PM * * Welcome to 2 Nahomon St. , Oak Bluffs, MA! Set on a private 1/4-acre level lot at the end of a quiet cul-de-sac, this home offers tranquility and convenience. The first floor features an ensuite bedroom for easy single-level living. Recent upgrades include a new septic system, upgraded electrical panel, new washer and dryer, and an outdoor shower. The spacious bonus room has potential to become a 4th bedroom. Within close proximity (1 mi) to Oak Bluffs Harbor, restaurants, attractions, and beautiful beaches, this home is perfect for enjoying everything Martha’s Vineyard offers. Plentiful parking and a cozy gas firepl

Luxury Home for sale in Vineyard Haven, MA:

MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open floor plan with cathedral ceilings and 3 sliding doors that take you out to the upper deck. Open the sliders to the expansive deck and you almost double the living space on the upper level. There is also a powder room on the upper level. The first floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-f

Luxury Home for sale in Vineyard Haven, MA:

Oak Bluffs, Steps to the Lagoon with a sandy beach, great for kayaking and sailing. This renovated 3 bedroom home features an open living area, with dining, kitchen, and living room, with plenty of room for entertainment. There are 2 First floor bedrooms, an office or den, a bathroom and laundry. The top floor is primary suite with walk-in closet and luxurious bathroom. The finish basement is complete with a home gym and utility room. The yard has a brick patio with Fireplace, seating area and dining table for outdoor meals. A front porch, garden, shed, and outdoor shower, are some of the many features this comfortable home has to offer.

Luxury Home for sale in Vineyard Haven, MA:

Embrace the history and character of this delightful 1870's Oak Bluffs cottage. Formerly the Laura Thomas Smith House, it was relocated from the Vineyard Highlands area, nestled in a quaint neighborhood close to the center of town and the harbor. It was documented in a 1978 Oak Bluffs Historical Survey and has been in the same family for 98 years. This cottage features a sun-filled living room, vintage kitchen, one bath and mudroom on the first floor, with all 3-bedrooms on the second floor. The cottage radiates timeless appeal, with its painted pine floors, exposed beams, inviting covered front porch, and a second-floor deck to take advantage of the summer breezes. The home was upgraded wi

Luxury Home for sale in Vineyard Haven, MA:

Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. Offering separation from the main part of the home is a dramatic cathedral-ceiling Great Room with a wood-burning stove where you will occupy most of your time. There is an office area set aside in this room and a cleverly designed spiral staircase with a loft perfect for overflow. Entering the opposite side of the home you will enjoy the open floor plan with a fully renovated kitchen, dining room, and living room with another wood-burning stove. A renovated

Luxury Home for sale in Vineyard Haven, MA:

East Chop-Near Oak Bluffs Center. This antique bungalow was lovingly restored to a modern year-round home by a Island craftsman. Completely rewired, replumbed, and insulated from the walls in and between the ceiling and roof. This fully winterized and roomy 2 bedroom 2 bathroom home has a complete basement below with finished rooms and separate laundry room. The fenced property provides privacy and outdoor comfort. with a garden back deck * * Sister property next door also for sale. * *

Luxury Home for sale in Vineyard Haven, MA:

Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf range, and wine cooler. There is a casual dining area off the kitchen and a formal dining room. The spacious first floor primary bedroom has a large walk-in closet, soaking tub, and bay window looking to the backyard. The other bedroom is currently being used as a TV room. The second level has two

Luxury Home for sale in Vineyard Haven, MA:

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This main house and guest house are perfectly sited on just over 2 acres and are ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. Guest house needs finishing and presents a number of possibilities. Both structures are sited with the potential to expand, and according to the West Tisbury Board of Health, the property can support up to 8 bedrooms. This property is being sold "as-is".

Luxury Home for sale in Vineyard Haven, MA:

OAK BLUFFS BEACHFRONT WITH DOCK - This beautifully renovated 2024 beachfront cottage offers panoramic views of Vineyard Haven Harbor, along with a private dock and an additional parcel for extra privacy and water frontage. The three-bedroom, two-bath home combines modern upgrades with classic Vineyard charm, featuring original wood floors, beadboard walls, and a cozy gas fireplace. The living room's picture window frames stunning harbor views, while the adjacent dining area and sunroom provide ideal spaces for relaxation and entertainment. The updated kitchen is a chef's dream with new appliances, double ovens, butcher block countertops, and a farmhouse sink. The first-floor bedroom opens t

Luxury Home for sale in Vineyard Haven, MA:

Long Point Beach Retreat - Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both levels of the home, creating unique spaces for outdoor relaxation and enjoyment. The property showcases an abundance of recent upgrades, including a newly renovated gourmet Cook's Kitchen with stunning quartz countertops and brand new GE® stainless appliances throughout. Additionally, all bathrooms h

Luxury Home for sale in Vineyard Haven, MA:

Delightful Vineyard Haven Home With Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this smartly-design and meticulously maintained residence provides a modern and spacious environment for comfortable island living. Upon entry, the home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that seamlessly connects with the living and dining areas. A cozy Family Room/Den is also located on the main floor. The primary bedroom is a private sanctuary, complete with a walk-in closet and a spa-like en suite bathroom. Outside, the m

Luxury Home for sale in Vineyard Haven, MA:

This four bedroom, three bathroom home is just a short walk to Downtown Vineyard Haven. The home was renovated in 2017 which included expanding the second floor, new windows, new roof, and new siding. The first floor features an open living/dining area, kitchen with stainless steel appliances, a full bathroom, and a bedroom with a walk in closet and built-in shelving/desk. The second floor has two large bedrooms with a second full bathroom. The partially finished basement includes a living area and a fourth bedroom with a full bathroom. The yard is fully fenced in with mature plantings and a patio in the rear. Also on the property there is a single car garage that is in need of some TLC. Th

Luxury Home for sale in Vineyard Haven, MA:

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.

Luxury Home for sale in Vineyard Haven, MA:

LOCATION, LOCATION, LOCATION. .House & Guest House. Turnkey! A short stroll to town where you find shopping, dining, beaches, ferries . .. . and on the way pass through the Oak Bluffs Art's District, the Martha's Vineyard Camp-Meeting Association featuring the iconic Tabernacle and over 300 Gingerbread cottages. Oak Bluffs elementary school is just a few blocks away. This property offers a main house and a guest house on over a quarter acre of landscaped land. The main house offers two bedrooms, both on the second floor, and an open living-dining-kitchen area and a full bathroom on the first floor. Enjoy the large rear deck which includes a 10'x 10' Pavillion. The second dwelling is a

Luxury Home for sale in Vineyard Haven, MA:

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 bat

Luxury Home for sale in Vineyard Haven, MA:

Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a gas stove, an alarm system, and new Andersen sliding doors. Outside, 12 White Pine trees enhance privacy, with Belgian Block pavers, a flagstone walkway, and a large planting bed with a bird bath. The condo offers a private driveway, a 1-car garage with custom shelving, and extra storage for bikes an

Luxury Home for sale in Vineyard Haven, MA:

$275,000 PRICE ADJUSTMENT - SELLER MOTIVATED TO CLOSE THIS YEAR! Renovated Beachfront Cottage with Private Dock and Stunning Lagoon Views. This charming waterfront home offers 100 feet of sandy shoreline and a 90-foot private dock for kayaking, swimming, and more, right from your doorstep. Set on over 13,000 square feet at the end of a quiet lane, this lovingly maintained three-bedroom, two-and-a-half bath cottage has been a cherished family retreat. Inside, the updated kitchen with granite countertops opens to the dining room, offering water views. The living room features a beach stone fireplace, perfect for cozy waterfront living. Upstairs, the primary bedroom boasts Lagoon views, a larg

Luxury Home for sale in Vineyard Haven, MA:

New Construction To Be Built~The Homes at Lagoon Ridge is a subdivision in Oak Bluffs of stylish, new construction properties. The "Naushon" home design is an elegant 2 bedroom, 3 full and 1 half bath home with over 2500sf of living space. Just off the foyer, the Great Room is open to the kitchen and dining area, offering an ideal space to entertain. The smart kitchen design includes stainless steel Bosch appliances and quartz countertops. For privacy, the main level guest bedroom and en suite bathroom are on the opposite side of the foyer. The spacious primary bedroom suite, on the second level, features a private bathroom with Kohler soaking tub and a tiled walk-in shower. A ful

Luxury Home for sale in Vineyard Haven, MA:

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home

Luxury Home for sale in Vineyard Haven, MA:

West Tisbury with bells and whistles! This well tended to property has seen a LONG LIST of recent IMPROVEMENTS to make ownership easy and up-island life a breeze! Nicely tucked in and off of Old County Road means easy access to up island and down. The raised ranch style provides terrific living space duality. BOTH LEVELS have living rooms with fireplaces as well as renovated bathrooms and comfortable spaces. Recently installed heat system and central AC, new windows and sliders + insulated attic and soffit with ridge vent. ALL this and a 2022 installed FOUR bedroom septic system. The generous second floor deck with south west exposure is a perfect perch and truly expands the living space. N

Luxury Home for sale in Vineyard Haven, MA:

Oasis in the woods of West Tisbury! This meticulously constructed, updated and well-maintained home is set on an expansive, yet private, 2.7 acre parcel. This 6-bedroom home has three levels of living space, 2,363 square feet on the spacious first floor, 672 over the garage and 1,877 in the bright, sunlight-filled lower level, for a total of 4,912 square feet. This home abounds in gathering places, inside and outside, highlighted by additional flexible finished spaces, mature gardens, fruit trees, a sizeable patio with outdoor kitchen and a 16' X 32' inground pool that will be the focal point of your summer gatherings. The owner designed the exterior of this home to be as low maintenance as

Luxury Home for sale in Vineyard Haven, MA:

East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to call East Chop, a close-knit community only a short distance from the harbor and downtown Oak Bluffs, home!

Luxury Home for sale in Vineyard Haven, MA:

$355,000 PRICE ADJUSTMENT – SELLER MOTIVATED TO CLOSE THIS YEAR! Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living area features a dramatic living room and a chef's kitchen that opens to the dining room with access to the deck. An ensuite bedroom, half bath, and laundry room complete this floor. The upper level is dedicated to the primary ens

Luxury Home for sale in Vineyard Haven, MA:

Welcome to 12 Mae Avenue, a 3-bed, 2-bath home with 1,700sf of Martha's Vineyard charm. Nestled in Oak Bluffs' sought-after Lagoon area, this gem offers panoramic Lagoon views from almost every angle. The first floor features a full bathroom and three generous bedrooms, including a primary bedroom with its own ensuite bathroom. The rear door leads to a covered porch with two roomy swings. The second floor boasts a spacious living room with vaulted ceilings, a dining room, and a kitchen with stunning views. Step outside to the upper porch, where automatic awnings provide shade for outdoor dining and entertainment. With its ideal location near the Lagoon and downtown Oak Bluffs, this home is

Luxury Home for sale in Vineyard Haven, MA:

East Chop close to beach and town! This 4 bedroom home has it all; great location, wrap around porch, plenty of parking, oversized garage, large shed, walk-out basement, heating system, original hardwood floors. 4 Bedroom Title V passed septic system. Don't miss this opportunity to buy in this desirable neighborhood just a short distance to the beaches, shops, and restaurants of Downtown Oak Bluffs.

Luxury Home for sale in Vineyard Haven, MA:

Located in 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 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 be

Luxury Home for sale in Vineyard Haven, MA:

Welcome to your dream retreat in Oak Bluffs. A magnificent 8 br oceanview estate. This property is designed to accommodate family and friends with ease while offering an elegant and serene enviroment 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 view 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

Luxury Home for sale in Vineyard Haven, MA:

East Chop Harbor Front Luxury Condominiums -- Location, location, location -- This 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have

Luxury Home for sale in Vineyard Haven, MA:

The price above reflects the Reserve Price for the property, which is being marketed for sale by luxury private auction. Bidding is open through November 13. Seller reserves the right to accept or reject bids. 5% Buyer's Premium. Additional terms apply. Please visit Paramount Realty USA's website for more details. Located on the very northernmost tip of Martha's Vineyard, this landmark property is one of the grandest and most historic homes in the distinguished West Chop neighborhood. The setting is unparalleled with a large private beach and 210-degree water views so expansive that you can enjoy both sunrises and sunsets from the same deck. The home still exudes olde worlde charm despite a

Luxury Home for sale in Vineyard Haven, MA:

Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, and a wood stove. The kitchen has a huge walk-in pantry and opens to the cathedral-ceiling living area for comfortable entertaining. There are two bedrooms, including a spacious primary bedroom that occupies the entire right side of the house, and a full bath with a soaking tub. The wrap-around deck and screened porch expand the living space to the outdoors and over

Luxury Home for sale in Vineyard Haven, MA:

East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the "Tivoli", features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips a