1,867 properties 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

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard

This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, provides flexible space for two additional overnight guests, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious pri

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities-ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities-ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath

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

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard

Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck -perfect for relaxing or entertaining. Additional highlights include in-unit laundry, dedicated parking, a storage area, a new septic system (2025), and low HOA fees. Ideally located near Farm Neck Golf Club, Felix Neck Wildlife Sanctuary, scenic bike paths, and the down-island towns, this inviting property offers the best of coastal living

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

Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful renovation, the property offers an excellent foundation to create long-term value. An attic and basement offer generous storage and space for updated mechanical systems, while an interior staircase provides the opportunity to reconnect the two residences into a single-family home if desired. The seller will provide a $50,000 credit at closing toward the installation of a new septic system

HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE and PRICED APPROX $100,000 less than an identical unit that Just Sold this summer! Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you're not here, the management team will rent and take care of everything for you. AMENITIES ARE AMAZING! There's a beautiful pool, spacious outdoor area with lots of seating, fire pits for evening get-togethers-, play area and barbecues. Right next to the popular Noman's restaurant with outdoor music and activities- a delight for all! and Strolling distance to two ocean beaches, bike paths along w/ buses to towns. Very close to Oak Bluffs village! Come and see and I promise you-you won't want to leave! Brokers must accompany clients

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living space plus 700+ square feet of newly finished recreation space above the two-car garage, with a private entrance and second-floor deck. The inviting first floor features a spacious kitchen with center island and abundant counter space, an adjacent dining room with wood stove, and glass doors opening to a wood deck and bluestone patio. Multiple sitting areas, a living room with gas fireplace, and private office provide flexible spaces for relaxing and working. Upstairs, two guest bedrooms share an updated bath, while the spacious primary suite features a walk-in closet and light-filled bath with soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bath add comfort. Additional amenities include a two-car garage and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this versatile home offers an ideal setting for relaxed island

Island Inn. tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown. OR a short distance north to Oak Bluffs center, ferry terminal, and all the excitement of Oak Bluffs. Gulph Creek Hotel Management handles the rentals, housekeeping and management for owners and renters. Management office on site. The expansive property includes 3 clay tennis courts, a heated community pool, barbeque areas, picnic tables and firepits, children's playground area and a community meeting room. The perfect spot to enjoy your vacation or to use the unit for investment purposes. Open April - October. TO BE SOLD FULLY FURNISHED

HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE and PRICED APPROX $100,000 less than an identical unit that Just Sold this summer! Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you're not here, the management team will rent and take care of everything for you. AMENITIES ARE AMAZING! There's a beautiful pool, spacious outdoor area with lots of seating, fire pits for evening get-togethers-, play area and barbecues. Right next to the popular Noman's restaurant with outdoor music and activities- a delight for all! and Strolling distance to two ocean beaches, bike paths along w/ buses to towns. Very close to Oak Bluffs village! Come and see and I promise you-you won't want to leave! Brokers must accompany clients

Discover the charm of this inviting single-story ranch with a large, finished basement, perfect as a vacation retreat or year-round home. Extensively renovated, this charming 3-bedroom, 1.5-bath home offers comfort and effortless living. The finished basement adds nearly another 1000 SF of living space with a spacious TV room and game area for extra entertainment, while the welcoming back deck and enclosed outdoor shower make it easy to unwind after a day at the beach. Recently installed solar panels add significant energy efficiency. Set on a landscaped corner lot, the home is close to Lagoon Pond, where you can swim, shellfish, boat, and take in unforgettable sunsets. The location is close to Farm Neck Golf Club and downtown Oak Bluffs, with easy access to Island beaches, dining, and attractions. With strong rental bookings for 2026, this home is also a smart investment opportunity

A Victorian Grand Dame overlooking Ocean Park - in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and guests that have enjoyed dramatic sunsets, spectacular August fireworks and evening strolls to town for generations. This historic home retains its Victorian character while having been carefully maintained and updated over the years. Recent improvements include a Title V septic, all new windows, ducted mini-splits for heat/AC throughout the house plus two propane monitors and outdoor shower. Lastly, there is parking for three cars in the parking area behind the house - a big plus in the heart of downtown

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 meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering swimming, kayaking, and paddleboarding from your backyard. The main house features a welcoming sun porch, living room with a stone fireplace, light-filled primary bedroom with water views, and an updated kitchen and dining area with brick floors and a built-in window seat. French doors open to a spacious lawn and a charming former boathouse converted into a unique dining pavilion. Additional highlights include a rooftop deck with panoramic water views, guest cottage, outdoor shower, garage with office, and garden shed. A quintessential Martha's Vineyard waterfront esc

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer as is

Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck -perfect for relaxing or entertaining. Additional highlights include in-unit laundry, dedicated parking, a storage area, a new septic system (2025), and low HOA fees. Ideally located near Farm Neck Golf Club, Felix Neck Wildlife Sanctuary, scenic bike paths, and the down-island towns, this inviting property offers the best of coastal living

A Victorian Grand Dame overlooking Ocean Park - in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home to family and guests that have enjoyed dramatic sunsets, spectacular August fireworks and evening strolls to town for generations. This historic home retains its Victorian character while having been carefully maintained and updated over the years. Recent improvements include a Title V septic, all new windows, ducted mini-splits for heat/AC throughout the house plus two propane monitors and outdoor shower. Lastly, there is parking for three cars in the parking area behind the house - a big plus in the heart of downtown

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

Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the harbor, while enjoying the privacy of a quiet residential neighborhood. Over the past decade, the property has benefited from extensive improvements, including a four-bedroom septic system, energy-efficient mini-split heating and air conditioning, updated windows, renovated bathrooms, irrigation, an outdoor shower, and countless additional upgrades that reflect exceptional pride of ownership. Fully booked for the 2026 summer season, the property provides immediate rental income from day one while offering exceptional flexibility for future personal use or continued investment. The property is

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living space plus 700+ square feet of newly finished recreation space above the two-car garage, with a private entrance and second-floor deck. The inviting first floor features a spacious kitchen with center island and abundant counter space, an adjacent dining room with wood stove, and glass doors opening to a wood deck and bluestone patio. Multiple sitting areas, a living room with gas fireplace, and private office provide flexible spaces for relaxing and working. Upstairs, two guest bedrooms share an updated bath, while the spacious primary suite features a walk-in closet and light-filled bath with soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bath add comfort. Additional amenities include a two-car garage and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this versatile home offers an ideal setting for relaxed island

In-Town Oak Bluffs Condo with Panoramic Water Views Experience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space. The condo features one generously sized bedroom plus a separate sleep nook, offering flexibility for guests, a home office, or additional sleeping accommodations. The nook could potentially be configured as a second bedroom, subject to applicable requirements and approvals. A true highlight is the rooftop deck shared with just one other unit (# 4 also ). This exceptional outdoor space provides panoramic water views across Nantucket Sound and Oak Bluffs Harbor, creating a spectacular setting for morning coffee, afternoon relaxation, or enjoying the beautiful island sunsets. Ideally situated in the heart of Oak Bluffs, this property places you within easy reach of the harbor, beaches, restaurants, shops, and the vibrant energy of Oak Bluffs center. Whether you're seeking a Martha'

Want to own a slice of Martha's Vineyard' As an owner of this studio style Condo-tel, you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm Neck Golf Course and lively Noman's Restaurant. This location is only a 5 minute drive from the Oak Bluffs ferry terminal and is conveniently located close to State Beach, the bus route, bike path and all that downtown Oak Bluffs has to offer. This unit is being sold furnished (wall hangings not included). The association allows for the interior decor of your choosing. A rare corner unit that even your pet can enjoy as this is a pet friendly property! The property is open to owners and guests on a seasonal basis from April - November. *Can be shown during turnovers only

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer as is

ALL OFFERS REQUIRE COURT APPROVAL in multiple jurisdictions and may be somewhat lengthy. A straightforward offer is encouraged and may help expedite the required court approvals in multiple jurisdictions. Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous.69-acre lot. Built in 2014, the property presents an excellent opportunity for a year-round residence, vacation getaway, or investment. The property is being sold as is. Buyers and their agents are encouraged to perform their own due diligence and verify any potential for expansion or additional improvements with the Town of Oak Bluffs. All buyer's agents must submit proof of funds with any offer. The Court approval in multiple jurisdictions is required and may result in a longer than usual acceptance process

ALL OFFERS REQUIRE COURT APPROVAL in multiple jurisdictions and may be somewhat lengthy. A straightforward offer is encouraged and may help expedite the required court approvals in multiple jurisdictions. Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous.69-acre lot. Built in 2014, the property presents an excellent opportunity for a year-round residence, vacation getaway, or investment. The property is being sold as is. Buyers and their agents are encouraged to perform their own due diligence and verify any potential for expansion or additional improvements with the Town of Oak Bluffs. All buyer's agents must submit proof of funds with any offer. The Court approval in multiple jurisdictions is required and may result in a longer than usual acceptance process

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination