Oak Bluffs Houses for Sale

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  /55

  $1,830,000

  • 4 Beds
  • 4 Baths
  • 1,600 Sq Ft

  12 & 14 Maple Ave, Oak Bluffs, MA 02557

  Two Historic Oak Bluffs Cottages - Prime Location – Deeded SeparatelyPerched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout.Built at a time when

  Leslie C. Floyd Portfolio Real Estate, Inc.

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
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  /42

  $1,590,000

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft

  48 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  Bright, Open Living, Steps from the Lagoon!Spacious and sun-filled, this charming 3-bedroom, 2-bath home offers effortless single-level living. As you enter the home, you're welcomed by a spacious sitting area that seamlessly flows into an open-concept living room, dining area, and modern kitchen—perfect for entertaining and everyday living. A separate home office or den provides

  Susan Wallo Compass | The O'Hanlon Group

  48 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  /23

  $1,790,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02557

  Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

  Alan Schweikert Ocean Park Realty Inc

  11 Beach Rd, Oak Bluffs, MA 02557
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  /30

  $829,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  17 Siloam Ave, Oak Bluffs, MA 02557

  PRISTINE YEAR ROUND COTTAGE RENOVATED THROUGHOUT ~Welcome to 17 Siloam Avenue, a delightful cottage nestled in the historic Martha’s Vineyard Camp Meeting Association, offering spectacular sunset views of Sunset Lake and the distant harbor from its inviting porches. The current owners have cherished this home year-round for 13 years, and it’s easy to see why. This spacious residence features an

  Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
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  /39

  $10,500,000

  • 8 Beds
  • 6 Baths
  • 3,888 Sq Ft

  47 E Chop Dr, Oak Bluffs, MA 02568

  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 a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr, Oak Bluffs, MA 02568
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  /29

  $3,000,000

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  311 E Chop Dr, Oak Bluffs, MA 02568

  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 open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning

  Gerrett Conover Landvest MV

  311 E Chop Dr, Oak Bluffs, MA 02568
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  /68

  $4,395,000

  • 3 Beds
  • 5.5 Baths
  • 4,046 Sq Ft

  267 Barnes Rd, Oak Bluffs, MA 02557

  Live the Dream on Martha's Vineyard! Whether you're seeking a year-round residence or a seasonal escape, this is a once-in-a-lifetime opportunity to own a piece of paradise. Step into a world of coastal luxury with 163 feet of pristine Lagoon frontage, complete with your own private sandy beach. Nestled on 1.25 acres of lush, landscaped paradise, this rare gem offers sweeping lawns, panoramic

  Stephanie Roache Donnelly + Co.

  267 Barnes Rd, Oak Bluffs, MA 02557
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  /67

  $3,150,000

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

  Casandra Hyland Landmarks at TODAY Real Estate

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  /20

  $3,750,000

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  28 Beach Rd, Oak Bluffs, MA 02557

  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 through and through

  Scott Lewis Lewis Real Estate Services, LLC

  28 Beach Rd, Oak Bluffs, MA 02557
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  /17

  $995,000

  • 2 Beds
  • 0.5 Baths
  • 952 Sq Ft

  50 Canonicus Ave, Oak Bluffs, MA 02557

  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

  Michele Moore Island Real Estate

  50 Canonicus Ave, Oak Bluffs, MA 02557
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  /29

  $2,500,000 Open Tue 11AM - 2PM

  • 6 Beds
  • 3.5 Baths
  • 1,616 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  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 great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

  Carleen Cordwell Anchor Realty of Martha's Vineyard

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /39

  $3,750,000

  • 4 Beds
  • 3 Baths
  • 2,204 Sq Ft

  9 Weston Ave, Oak Bluffs, MA 02557

  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 area and a first floor bedroom with private bath. The 2nd floor offers two guest bedrooms and a master

  Gerrett Conover Landvest MV

  9 Weston Ave, Oak Bluffs, MA 02557
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  /24

  $2,445,000

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

  Brian Smith Portfolio Real Estate Inc.

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /49

  $849,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  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. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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  /28

  $10,500,000

  • 7 Beds
  • 6 Baths
  • 3,888 Sq Ft

  47 E Chop Dr, Oak Bluffs, MA 02568

  East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular water views, dock with 9 slips, and just steps from beaches, tennis club, downtown and ferries to mainland! Property has been extensively renovated recently. Uses include -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion,2.) Currently

  Perry Patterson MV Luxury Homes LLC

  47 E Chop Dr, Oak Bluffs, MA 02568
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  /46

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 1,399 Sq Ft

  34 Windemere Rd, Oak Bluffs, MA 02557

  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 sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to

  JoJo Lambert Island Home Realty Inc.

  34 Windemere Rd, Oak Bluffs, MA 02557
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  /19

  $950,600

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft

  5 Johns Way, Oak Bluffs, MA 02557

  Property is being offered via Real Estate Auction on Wednesday, September 17 at 12pm on-site. The actual selling price will be determined auction day. List price/estimated value seen is set at the real estate tax assessment. Pre-auction offers must be presented on the auction P&S and are subject to seller confirmation. 10% Buyer's Premium applies. Site: .36± acre with irrigation, fencing, gravel

  Justin Manning JJManning Auctioneers

  5 Johns Way, Oak Bluffs, MA 02557

Showing Results 41 - 57, Page 2 of 2