Oak Bluffs Properties for Sale

Address: 150 East Chop Drive Town: Oak Bluffs Link ID: 42039

Price: $13,200,000

Property Description:
Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all t... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43065

Price: $10,500,000

Property Description:
East Chop waterfront – Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 385 Barnes Road Town: Oak Bluffs Link ID: 43040

Price: $5,995,000

Property Description:
EXQUISITE WATERFRONT RETREAT WITH POOL AND SUPERLATIVE SUNSETS. Luxurious island living awaits at this stunning private waterfront retreat, set on a private 125-foot stretch of sandy beachfront. Three floors of living space totaling 5,400+ square feet, seamlessly blend casual elegance with indoor-... Click here for more details

Property description and photographs provided by listing agent: Compass | Point B

Address: 7 Overview Lane Town: Oak Bluffs Link ID: 43001

Price: $5,100,000

Property Description:
A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 267 Barnes Road Town: Oak Bluffs Link ID: 43025

Price: $4,500,000

Property Description:
Enjoy waterfront living at its best with 163’ of Lagoon frontage, including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the wat... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 9 Weston Avenue Town: Oak Bluffs Link ID: 42664

Price: $3,950,000

Property Description:
This 4-bedroom / 3-bath home lies in the middle of East Chop at the highest point on the bluff offering expansive views of Vineyard Sound. The home features a large clear story living room with fireplace, a family room/kitchen also with fireplace, a huge screened porch opening up to a large deck are... Click here for more details

Property description and photographs provided by listing agent: Landvest MV

Address: 28 Beach Road Town: Oak Bluffs Link ID: 42946

Price: $3,750,000

Property Description:
Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort th... Click here for more details

Property description and photographs provided by listing agent: Lewis Real Estate Services, LLC

Address: 98 Farm Neck Way Town: Oak Bluffs Link ID: 43207

Price: $3,700,000

Property Description:
Farm Neck Golf Club – Undeveloped Water View Parcel with Membership. A truly rare opportunity to own one of the last remaining undeveloped lots within the prestigious Farm Neck Golf Club community. This exceptional parcel offers sweeping water views of Sengekontacket Pond and the Vineyard Sound, ... Click here for more details

Property description and photographs provided by listing agent: Compass LLC

Address: 34 Massasoit Avenue Town: Oak Bluffs Link ID: 42580

Price: $3,500,000

Property Description:
Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a grea... Click here for more details

Property description and photographs provided by listing agent: Anchor Realty of Martha's Vineyard

Address: 34 Massasoit Avenue Town: Oak Bluffs Link ID: 42756

Price: $3,500,000

Property Description:
Circuit Ave. Commercial Property Build your own commercial building of your dreams on the last B1 undeveloped commercial property on Circuit Avenue's main strip. The commercial land had previously approved development plans including mixed use with commercial store front and apartments or condos abo... Click here for more details

Property description and photographs provided by listing agent: Anchor Realty of Martha's Vineyard

Address: 63 Bayes Hill Road Town: Oak Bluffs Link ID: 42800

Price: $3,500,000

Property Description:
Picture yourself in this beautifully designed custom home offering the ultimate in privacy. The first floor has an open floor plan which includes the dining room, kitchen, wet bar, and living space. Bypass siding doors separate the living space from the dining and kitchen. Experience the ultimate ... Click here for more details

Property description and photographs provided by listing agent: Landmarks at TODAY Real Estate

Address: 311 East Chop Drive Town: Oak Bluffs Link ID: 43084

Price: $3,250,000

Property Description:
This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an... Click here for more details

Property description and photographs provided by listing agent: Landvest MV

Address: 23 Circuit Avenue Extension Town: Oak Bluffs Link ID: 43212

Price: $3,100,000

Property Description:
Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boa... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 34 Windemere Road Town: Oak Bluffs Link ID: 40654

Price: $2,950,000

Property Description:
Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of ... Click here for more details

Property description and photographs provided by listing agent: Island Home Realty Inc.

Address: 111 Eastville Avenue Town: Oak Bluffs Link ID: 36870

Price: $2,798,000

Property Description:
Not to be missed!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location. FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated o... Click here for more details

Property description and photographs provided by listing agent: Arrowhead Homes

Address: 71 Netock Avenue Town: Oak Bluffs Link ID: 43171

Price: $2,650,000

Property Description:
On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling... Click here for more details

Property description and photographs provided by listing agent: Sotheby's International Realty

Address: 10 Wood Duck Way Town: Oak Bluffs Link ID: 43163

Price: $2,500,000

Property Description:
Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy’s freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and o... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 4 High Meadow Lane Town: Oak Bluffs Link ID: 42967

Price: $2,495,000

Property Description:
Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax ove... Click here for more details

Property description and photographs provided by listing agent: Portfolio Real Estate, Inc.

Address: 79 Circuit Avenue Town: Oak Bluffs Link ID: 42960

Price: $2,400,000

Property Description:
Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been bo... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 79 Circuit Avenue Town: Oak Bluffs Link ID: 42958

Price: $2,400,000

Property Description:
Historic classic Victorian located at the gateway to the Oak Bluffs Business district with frontage on Circuit Avenue and 5 off street parking spots. The layout offers incredible opportunities for a business and would also be ideal for a live/work situation or seasonal rental. With its large welcomi... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 22 Greenleaf Avenue Town: Oak Bluffs Link ID: 43058

Price: $2,390,000

Property Description:
Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal ... Click here for more details

Property description and photographs provided by listing agent: Compass | The O'Hanlon Group

Address: 30 Sengekontacket Road Town: Oak Bluffs Link ID: 42694

Price: $2,375,000

Property Description:
Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from al... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 4 Dempster Park Town: Oak Bluffs Link ID: 43106

Price: $2,285,000

Property Description:
East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. The 1st floor includes large living room with dining area and Rumford wood burning fireplace t... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 2 Farm Path Town: Oak Bluffs Link ID: 42860

Price: $1,995,000

Property Description:
"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom... Click here for more details

Property description and photographs provided by listing agent: Landmarks at TODAY Real Estate

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43078

Price: $1,995,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43096

Price: $1,995,000

Property Description:
East Chop Water Front Luxury Condominiums -- This 2-bedroom, waterfront condominium, the "Highlands", features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine conditio... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 34 Paddock Road Town: Oak Bluffs Link ID: 40763

Price: $1,950,000

Property Description:
The Preserve - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 35 Tuckernuck Avenue Town: Oak Bluffs Link ID: 43161

Price: $1,895,000

Property Description:
Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience. As you step inside, you... Click here for more details

Property description and photographs provided by listing agent: Compass | Point B

Address: 22 Paddock Road Town: Oak Bluffs Link ID: 42294

Price: $1,850,000

Property Description:
THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase ... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 66 Brush Pond Road Town: Oak Bluffs Link ID: 42739

Price: $1,699,000

Property Description:
**Charming Vineyard Waterfront Cottage in Oak Bluffs** Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the i... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 8 School House Village Town: Oak Bluffs Link ID: 42630

Price: $1,690,000

Property Description:
Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious li... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 46 Kennebec Avenue Town: Oak Bluffs Link ID: 43137

Price: $1,590,000

Property Description:
This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbo... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43068

Price: $1,495,000

Property Description:
East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, 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, beach... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43085

Price: $1,495,000

Property Description:
East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, "Cottage City", features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristin... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 47 East Chop Drive Town: Oak Bluffs Link ID: 43141

Price: $1,495,000

Property Description:
East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, "Oak Bluffs", features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new ki... Click here for more details

Property description and photographs provided by listing agent: MV Luxury Homes

Address: 14 High Meadow Lane Town: Oak Bluffs Link ID: 42472

Price: $1,449,000

Property Description:
MEADOW VIEW FARM/OAK BLUFFS - This sun-drenched, contemporary reverse-style home has 3 levels of living space. Well-maintained over those years, this 3+ bedrooms, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open kitchen,... Click here for more details

Property description and photographs provided by listing agent: Island Real Estate

Address: 70 Carol Lane Town: Oak Bluffs Link ID: 42456

Price: $1,250,000

Property Description:
Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The pr... Click here for more details

Property description and photographs provided by listing agent: Anchor Realty of Martha's Vineyard

Address: 130 Wing Road Town: Oak Bluffs Link ID: 42834

Price: $1,099,000

Property Description:
This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're ... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 249 County Road Town: Oak Bluffs Link ID: 42866

Price: $1,050,000

Property Description:
This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story ... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 50 Canonicus Avenue Town: Oak Bluffs Link ID: 42877

Price: $995,000

Property Description:
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. ... Click here for more details

Property description and photographs provided by listing agent: Island Real Estate

Address: 37 Circuit Avenue Town: Oak Bluffs Link ID: 42973

Price: $985,000

Property Description:
Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either ... Click here for more details

Property description and photographs provided by listing agent: Anchor Realty of Martha's Vineyard

Address: 37 Circuit Avenue Town: Oak Bluffs Link ID: 43000

Price: $935,000

Property Description:
Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds... Click here for more details

Property description and photographs provided by listing agent: Anchor Realty of Martha's Vineyard

Address: 1 Cottage Park Town: Oak Bluffs Link ID: 42887

Price: $925,000

Property Description:
The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs within the historic Martha's Vineyard Camp Meeting Association. Located on a pedestrian street, you'll be mere steps away from the shops and restaurants of Circuit Ave., Ocean Park, and the Oak Bluffs beaches. Thi... Click here for more details

Property description and photographs provided by listing agent: Island Real Estate

Address: 26 Winthrop Avenue Town: Oak Bluffs Link ID: 42248

Price: $899,000

Property Description:
Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. ... Click here for more details

Property description and photographs provided by listing agent: Alisan Lohan-Conway Properties

Address: 7 Highland Avenue Town: Oak Bluffs Link ID: 42382

Price: $750,000

Property Description:
BUILD YOUR DREAM HOME ON MARTHA'S VINEYARD! This almost 20,00sq ft of BUILDABLE land is nestled in the private quiet neighborhood of East Chop. Do you want to live conveniently close to downtown Oak Bluffs, the ferry terminal, beaches including Inkwell Beach, the Flying Horses Carousel, Ocean Park,... Click here for more details

Property description and photographs provided by listing agent: eXp Realty

Address: 56 Holmes Hole Road Town: Oak Bluffs Link ID: 42990

Price: $699,000

Property Description:
Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 25 Oak Avenue Town: Oak Bluffs Link ID: 42761

Price: $699,000

Property Description:
WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot. According to the engineer who has percolated the lot, it will allow a FIVE (5) bedroom regular septic system. The Board of Health have stated there are no Board of Health issues or limitations with this property and are deferring t... Click here for more details

Property description and photographs provided by listing agent: Alisan Lohan-Conway Properties

Address: 25 Oak Avenue Town: Oak Bluffs Link ID: 42766

Price: $699,000

Property Description:
WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the exiting building or build a new FIVE (5) BEDRO... Click here for more details

Property description and photographs provided by listing agent: Alisan Lohan-Conway Properties

Address: 47 Circuit Avenue Town: Oak Bluffs Link ID: 42760

Price: $600,000

Property Description:
Great opportunity for commercial space in a thriving business district with plenty of street parking and a storefront and side entrance. Office / Studio / Retail ~ Your choice! The space is versatile and is currently set up as a large open space with 2 dressing rooms, a large storage room in the bac... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 35 Temahigan Avenue lot 5 Town: Oak Bluffs Link ID: 43050

Price: $595,000

Property Description:
Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future hous... Click here for more details

Property description and photographs provided by listing agent: Arrowhead Homes

Address: 0 Worcester Avenue & Olinda Avenue Town: Oak Bluffs Link ID: 43015

Price: $575,000

Property Description:
Location, Location, Location. Rare Opportunity to own a 10,000 sq ft South facing level corner lot on a paved road that may accommodate up to 3 bedrooms with Board of Health approval. A sandy beach on Lagoon Pond is just a short stroll (about 1500 ft.) .....enjoy the beach, walk your pet, watch the... Click here for more details

Property description and photographs provided by listing agent: Ocean Park Realty Inc

Address: 0 Barnes Road Town: Oak Bluffs Link ID: 42701

Price: $530,000

Property Description:
Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residenc... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 47 Circuit Avenue Town: Oak Bluffs Link ID: 42759

Price: $525,000

Property Description:
This commercially zoned property enjoys plenty of foot traffic in the heart of Circuit Avenue’s pedestrian activity. The space is bright and cheery with great natural light. Currently set up as a hair salon with access to a shared half bath, the space can be transformed to fit other specific needs... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 0 California Avenue Town: Oak Bluffs Link ID: 42933

Price: $495,000

Property Description:
Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows 1 bedroom for this lot. Water and electric are nearby.

Property description and photographs provided by listing agent: Carroll & Vincent R.E.