348 houses for sale in 02575

New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach-perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious gathering space. The thoughtfully designed layout offers a private first-floor primary suite, while the second floor features two additional spacious bedrooms and a full bath. Step outside to a spacious back deck, ideal for outdoor dining, entertaining or relaxing after a day at the beach. Beautifully updated for today's lifestyle, this home offers a wonderful blend of comfort, coastal living and Vineyard charm

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests, multi-generational living, or a growing family. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers s

LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES. Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous accommodations for family, friends, and guests. From the EXPANSIVE ROOFTOP entertainment deck, enjoy sweeping 180-degree water views of Vineyard Haven Harbor - a spectacular vantage point for watching ferries and sailboats glide by at sunset. Originally built in 1859 by noted whaling captain Shaw Norris, this classic Greek Revival residence seamlessly blends historic character with modern luxury. Extensive renovations - including a new roof, siding, trim, and all-new mechanical systems - have transformed the property into a home that lives like new construction while preserving its architectural i

Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom-perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighbor

Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature. The true value lies in the property's remarkable expansion possibilities. A 6-bedroom septic system is already installed, allowing for the future construction of a substantial 5-bedroom main house while retaining the existing home as a guest house, rental property, or secondary dwelling. The lot also has ample room for a pool and outdoor entertaining spaces, creating an ideal Vineyard compound opportunity. Ideally located just over a mile from both the West Chop Club and Mink Meadows Golf Club, as well as downtown Vineyard Haven, the property offers convenient access to golf, boating, dining, shops, and ferry service while still maintaining a quiet, tucked-away f

Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous.35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha's Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable.35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches

Great Location Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress walkout door and large windows letting in natural light. The house has propane monitors, mini splits for cooling/heating as well as window A/C units on the second floor with backup electric baseboard. The property is in the Tashmoo Watershed and will need an enhanced system per the Town installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, boating, fishing, kayak storage, kayaking, Mink Meadows Golf, Tashmoo Town Beach, Tisbury school, Downtown Main Street and the year round Ferry Terminal

Great Location Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress walkout door and large windows letting in natural light. The house has propane monitors, mini splits for cooling/heating as well as window A/C units on the second floor with backup electric baseboard. The property is in the Tashmoo Watershed and will need an enhanced system per the Town installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, boating, fishing, kayak storage, kayaking, Mink Meadows Golf, Tashmoo Town Beach, Tisbury school, Downtown Main Street and the year round Ferry Terminal

Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the primary bedroom. The expansive screened porch effectively doubles the living room, offering an enchanting area for relaxation or gatherings. Tucked just beyond the main house is a versatile barn with its own half bath, currently set up as a rec room and gym, great for guests and entertaining. There are three outdoor showers, full insulation and mini-splits throughout for heat and A/C. The yard is expansive and private, with room to dream-gardens, a pool, or just wide-open space to roam. Best part of all, ownership at Black Point Beach is included, so you can easily bike, stroll or drive down the qui

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large deck and the rolling lawn. Come see this property to truly appreciate it

Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha's Vineyard. A gated drive winds through scenic farmland and open fields, running along the edge of Quenames Cove before arriving at your own white sand beach and the Atlantic Ocean. The setting is defined by open land and natural surroundings, creating a sense of space, privacy, and uninterrupted views. The compound consists of five thoughtfully crafted structures. The original 1842 Farmhouse has been meticulously restored and fully modernized, preserving its original character while introducing thoughtful updates, modern systems, and high-quality finishes. A detached structure offers flexible space for a gym or additio

Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom, two-and-a-half-bath home offers over 2,000 square feet of living space on a generous 0.26-acre lot, providing an exceptional combination of space, flexibility, and future possibilities. Painted wood floors and inviting living spaces showcase the home's enduring character and timeless appeal. Outside, the property features ample parking, with additional parking and open space both above the home and to the rear of the property, offering endless possibilities for entertaining, recreation, or future enhancements. An approved six-bedroom septic system presents an outstanding opportunity for expansion, allo

Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom, two-and-a-half-bath home offers over 2,000 square feet of living space on a generous 0.26-acre lot, providing an exceptional combination of space, flexibility, and future possibilities. Painted wood floors and inviting living spaces showcase the home's enduring character and timeless appeal. Outside, the property features ample parking, with additional parking and open space both above the home and to the rear of the property, offering endless possibilities for entertaining, recreation, or future enhancements. An approved six-bedroom septic system presents an outstanding opportunity for expansion, allo

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave-a 65+ acre water-access community-this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The sun-filled interior features a living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows. The chef's kitchen is appointed with stone countertops and Dacor(R) appliances. The second-floor primary suite boasts a private balcony with pond views and a stylish en suite bath. The garden level provides additional bedrooms and a bonus space with a Murphy bed. Outside, enjoy a bluestone terrace and two levels of decks overlooking a private yard. This move-in-ready home is offered fully furnished with over $80,000 in 2026 summer rental income already secured

4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha's Vineyard's most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting. Built by South Mountain Company, the home was designed with quality craftsmanship, natural light, and efficient living in mind. The expansive open living, kitchen, and dining area creates an inviting gathering space, anchored by warm cherry cabinetry, a wood stove, and oversized windows that bring the outdoors in. An atrium addition fills the home with sunlight and offers a tranquil indoor retreat year-round. Recent additions and eco-conscious features include composting toilets and a greenhouse, supporting a more sustainable and self-sufficient lifestyle. The partially finished basement offers exceptional flexibility with built-in de

Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen with a center island, and sliding doors that open to a spacious back deck-ideal for outdoor entertaining. The first floor includes a bedroom and a full bathroom, while the second floor offers two large bedrooms and a shared full bathroom. A full-height, dry basement provides excellent storage and potential for future expansion. The landscaped grounds create a picturesque environment, making it a perfect option for year-round living or rental investment

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach

Just 9/10 of a mile from Lambert's Cove Beach, this beautifully renovated tri-level home offers over 4,000 square feet of thoughtfully designed living space with six bedrooms and six bathrooms. Expanded and extensively updated in 2023, the home provides exceptional flexibility for entertaining and accommodating family and guests. A spa-like backyard features an inviting in-ground pool and hot tub with a waterfall, surrounded by patios, classic stone walls, mature landscaping, and vibrant blue hydrangeas, offering a private, tranquil island retreat. The top-level features an expansive sun deck with water views of Vineyard Sound, creating the perfect setting for relaxing or enjoying spectacular sunsets. Inside, generous living spaces span three levels, complemented by a beautiful gym overlooking the outdoor stone terraces and patios. A detached one-car garage includes unfinished space above, presenting an excellent opportunity for a future home office, studio, or recreation room. Ideally

Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond and Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home. A must-see to appreciate all the special touches throughout the Main House, Guest Camp, and Garage

Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and the heated, saltwater, 50x25x12 in-ground Pebble-Tek pool and pool house. There is an eat in kitchen with ample cabinetry and leathered granite countertops. Doors open onto the rear deck for outdoor entertaining. A guest bedroom, full bath, laundry and hallway lined with built in shelves are found on this level. Two dedicated office spaces-one on each level-provide exceptional flexibility. The upper office offers a vaulted ceiling with exposed beams, wide plank flooring, large windows, and sliding glass doors and sleeping loft. The lower office includes cork flooring, built in bookcases, large wi

Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing you toward a luxurious modern kitchen and the quiet warmth of a central masonry fireplace. Secrets unfold across multiple levels, from a secluded bonus room to an expansive lower level offering basement space-including 624 square feet of finished living space perfectly suited for a private lounge, studio, or hidden sanctuary. Climate is effortlessly controlled through central air conditioning and gas forced hot air, ensuring year-round comfort. Yet the true mystery of this property lies just beyond the newly renovated exterior siding and doors: a private outdoor paradise completely shielded fro

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and app

Wonderful Vineyard retreat located close to coveted long point beach and wildlife reserve, only a short bike ride away. This contemporary is adorned with 4 spacious bedrooms and an open living area with cathedral ceilings. Roomy yet cozy, this home has been the gathering place for 3 generations of family and has great potential for both rentals and year round use. With the recent addition of a huge 2 car garage with super high ceilings and ADU potential, already plumbed with water and a connection to the septic, this is a great property with tons of possibilities and potential

House and Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard also encompasses a sweet vegetable garden and storage shed. Inside, find an open floor plan with natural light streaming in from windows and skylights. The kitchen flows to the dining area, which flows to the spacious living room anchored by a wood-burning stove for cozy ambience. Also on this level is the primary bedroom with two closets, and a large full bathroom with a soaking tub and separate tiled shower. The larger, open loft upstairs offers versatile living space perfect for reading, television, or spillover guests. Downstairs on ground level is another full bathroom and two bedrooms plus a light-filled home office with a convenient exterior access. Other features for the main house

A place of serenity tucked in the woods of Chilmark. Beautifully designed and constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven and Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace-ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace-ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck-perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll find two bedrooms with beautiful wood floors, built-in drawers, and cabinets that add both charm and functionality to the rooms. These bedrooms share a hall bath, making the second floor an ideal space for family or guests. A generous bonus room above the garage offers flexible space for a home office,