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: 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: 0 Eastville Avenue Town: Oak Bluffs Link ID: 40762

Price: $4,400,000

Property Description:
EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vi... Click here for more details

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

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: $3,950,000

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

Price: $2,500,000

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

Price: $2,500,000

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: 6 Marthas Park Road Town: Oak Bluffs Link ID: 42914

Price: $2,495,000

Property Description:
Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open concept kitchen with marble counter tops and st... Click here for more details

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

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

Price: $1,950,000

Property Description:
The Preserve at the Woodlands - 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 par... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 34 Tower Ridge Road Town: Oak Bluffs Link ID: 42638

Price: $1,895,000

Property Description:
Welcome to a modern oasis nestled in the lovely community of Tower Ridge. This exquisite 4-bedroom, 3-1/2 bathroom residence offers generous living space, perfectly designed for comfort and style. Step inside to discover a beautifully renovated kitchen, featuring sleek finishes and modern appliances... 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: $1,800,000

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: 9 Goode Street Town: Oak Bluffs Link ID: 42166

Price: $1,775,000

Property Description:
Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedro... Click here for more details

Property description and photographs provided by listing agent: Grace Hagerty Real Estate Inc

Address: 33 Clay Avenue Town: Oak Bluffs Link ID: 41739

Price: $1,750,000

Property Description:
East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

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

Price: $1,449,000

Property Description:
MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The s... Click here for more details

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

Address: 119 Alpine Avenue Town: Oak Bluffs Link ID: 42891

Price: $1,299,000

Property Description:
Oak Bluffs Residence with Detached Cabin. Centrally located in Oak Bluffs, this property offers the rare opportunity to own a home in a prime residential location complemented with a detached cabin. The main house features, on the first floor, an inviting living/dining area, functional kitchen, a... Click here for more details

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

Address: 51 Head of the Pond Road Town: Oak Bluffs Link ID: 41818

Price: $1,299,000

Property Description:
Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike... Click here for more details

Property description and photographs provided by listing agent: Bruce Stuart and Associates

Address: 10 Kims Way Town: Oak Bluffs Link ID: 42717

Price: $1,250,000

Property Description:
Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/di... Click here for more details

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

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: 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: 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: 51 Rural Circle Town: Oak Bluffs Link ID: 42521

Price: $725,000

Property Description:
The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some or... Click here for more details

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

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 with this property and are deferring to the engineers... 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. If your preference is to build a new FIVE (5) BEDROOM House instead, the Seller has already been t... Click here for more details

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

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: 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: 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.

Address: 21 Island Inn Road Town: Oak Bluffs Link ID: 41920

Price: $389,900

Property Description:
Live the beautiful Island Life with this gorgeous condo at an affordable price. This is a 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. Th... Click here for more details

Property description and photographs provided by listing agent: Austin R.E. Properties of MV