652 houses for sale in Oak Bluffs town

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations. Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight throughout. The first floor features three spacious bedrooms and a full bath with double vanities, while warm oak and maple flooring pair elegantly with custom cherry staircases and built-ins. The open-concept second level creates the perfect gathering space for entertaining and relaxed coastal living. The kitchen, dining, and living areas flow seamlessly together and open through three sliding doors onto an expansive sun-drenched deck - ideal for alfresco dining, morning coffee, sunset cocktails, or summer entertaining. The private primary suite offers its own slider to the deck, along with a spa-like e

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

ENJOY THE SEA BREEZES AND SPECTACULAR VIEWS. Wake up to the ever-changing beauty of Vineyard Sound, watch the ferries cross in the distance toward Woods Hole, and end the day with sunset views stretching down the Lagoon. Designed to celebrate its extraordinary setting, this 4-bedroom, 2.5-bath home offers a rare lifestyle defined by light, water, and effortless indoor-outdoor living. With commanding views from nearly every room, the home invites you to slow down and take in the scenery from every angle. Two levels of covered decks overlook Vineyard Sound, while two additional levels of decks face the Lagoon, creating multiple outdoor spaces for morning coffee, afternoon reading, summer entertaining, or quiet evenings under the stars. The first level offers three comfortable bedrooms, a spacious family room, a full bath with laundry, and generous storage - ideal for hosting family and friends after a day at the beach, on the boat, or exploring the Island. Upstairs, the sun-filled open l

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property includes a newly beautifully renovated 2 bedroom 2 bathroom guest house. This guest house is offered fully furnished. This listing documents include a custom landscape design plan. This very large parcel of land is well suited to get started building an investor dream or family compound

Located in the heart of Oak Bluffs, the Martha's Vineyard Camp Meeting Association is in an area commonly known as The Campground. This is the home of the colorful, renowned gingerbread cottages. The iconic iron Tabernacle is located in the center of the Campground. This historical cottage is a short distance from everything that Oak Bluffs has to offer, including a public beach, boating, shops, ferries, and restaurants. It is just a one block walk to the main street, Circuit Avenue. It is well-hidden on a quiet, private circle of cottages, away from the hustle and bustle. The Tabernacle offers summer community sing alongs, various concerts and more. Onsite parking is provided. This cottage is a diamond in the rough awaiting a buyer willing to make improvements

Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much opportunity; this house is being sold As-Is

Your opportunity in Sengekontacket! Being sold turnkey. This modern home has four bedrooms and three full baths. Large windows and high vaulted ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the kitchen, living room and dining room. The primary en suite includes full private bath with Jacuzzi tub and shower, walk-in closet and dressing area. Three sliders lead onto a large sunny deck from the living area, great for alfresco dining, lounging or entertaining, extending your living space. The fourth slider accesses the deck from the primary bedroom. The full finished basement has eighteen foot high ceilings, multiple windows and glass back door. The basement also includes a third full bath and utility room. This surprising basement would make a fantastic recreation, media room, playroom, dance stud

Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio-creating an inviting connection between indoor comfort and outdoor living. The first floor also includes a bedroom with a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus offering a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use or a private retreat. Strong rental history!

Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle

Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations. Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight throughout. The first floor features three spacious bedrooms and a full bath with double vanities, while warm oak and maple flooring pair elegantly with custom cherry staircases and built-ins. The open-concept second level creates the perfect gathering space for entertaining and relaxed coastal living. The kitchen, dining, and living areas flow seamlessly together and open through three sliding doors onto an expansive sun-drenched deck - ideal for alfresco dining, morning coffee, sunset cocktails, or summer entertaining. The private primary suite offers its own slider to the deck, along with a spa-like e

Rare Opportunity to Be in a Special Location and Neighborhood! 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. Home is being sold 'as is'. Septic is a functioning cesspool but it will need to be upgraded. Basic engineering is being completed and a septic plan is being drawn up. It will be the Buyer's responsibility to have the plan approved and complete the installation as part of the overall

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter - whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting

Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a privat

The Doll House is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering exceptional opportunities for swimming, kayaking, and paddleboarding directly from your backyard. The main residence features a welcoming sun porch, an inviting living room anchored by a stone fireplace, and a light-filled primary bedroom with tranquil water views. The updated kitchen and adjoining dining area showcase beautiful brick floors and a built-in window seat. French doors open from the kitchen to a spacious lawn designed for outdoor entertaining, complete with a charming former boathouse reimagined as a unique dining pavilion. A strikin

Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio-creating an inviting connection between indoor comfort and outdoor living. The first floor also includes a bedroom with a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus offering a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use or a private retreat. Strong rental history!

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch and designed w/ Vineyard charm and modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open and w/ a separate entrance for an in-law or ADU. 1st FL en suite BR and a common half bath at the foyer entry. Large kitchen w/ full appliances and a 10' stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry and a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon and Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior and aerial video avai

ENJOY THE SEA BREEZES AND SPECTACULAR VIEWS. Wake up to the ever-changing beauty of Vineyard Sound, watch the ferries cross in the distance toward Woods Hole, and end the day with sunset views stretching down the Lagoon. Designed to celebrate its extraordinary setting, this 4-bedroom, 2.5-bath home offers a rare lifestyle defined by light, water, and effortless indoor-outdoor living. With commanding views from nearly every room, the home invites you to slow down and take in the scenery from every angle. Two levels of covered decks overlook Vineyard Sound, while two additional levels of decks face the Lagoon, creating multiple outdoor spaces for morning coffee, afternoon reading, summer entertaining, or quiet evenings under the stars. The first level offers three comfortable bedrooms, a spacious family room, a full bath with laundry, and generous storage - ideal for hosting family and friends after a day at the beach, on the boat, or exploring the Island. Upstairs, the sun-filled open l

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter - whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting

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