Oak Bluffs Real Estate

Oak Bluffs is a classic beach resort town on the northeast shore of Martha's Vineyard. Real estate in Oak Bluffs includes condos, single family homes, homes with dock access, acreage, and more. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

Contact us to ask questions or schedule a tour, or scroll down to browse all Oak Bluffs real estate on Martha’s Vineyard.

Register with us to save your favorite Martha's Vineyard real estate listings and receive notification when similar properties become available.

22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 38557

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 1.867

THIS IS THE ONLY LOT AVAILABLE in the PRESERVE at The WOODLANDS! COMING SOON...TO BE BUILT...by SHAWN CHAPPS...UNDER EARLY STAGES OF DESIGN and STILL TIME to CUSTOMIZE with YOUR OWN PERSONAL TOUCHES! Sophisticated Sprawling Contemporary Barn Style Residence with Clean Classic Lines, Natural Timber Beams, Field Stone Fireplace and Soaring Ceilings. This Spacious Airy Open Floor Plan will have no shortage of living areas with multiple intimate gathering spaces surrounded by lots of glass that displays an unobstructed panorama of the lush landscaped backyard and 20x 40 Gunite Pool and Spa. The Decked Out Chefs Kitchen will be a fusion of modern design, rustic accents and State of the Art Appliances. Boasting 6 en suite luxury bedrooms and unmatched bathrooms, with deep soaking tubs, artistic tiled showers, custom vanities, walk-in closets, and sitting areas all designed for convenience and comfort. A generous walk-out finished basement, containing over 2000 square feet, will include additional living areas along with a custom home bar, gym/media room and or wine cellar. Other Rare feature is the "Show Stopping Two Story Vaulted Stairway" This Unparalleled design with exceptional visuals highlighted by exquisitely detailed finishes will be SUPER DELUXE; So Be prepared for the "WOW FACTOR " Don't Wait...Call Today to Secure this RARE OFFERING in the POSH PRESERVE Oak Bluffs' Newest Luxury En Clave abutting conservation land and trails for hiking, walking and biking!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

11 Peter Williamson Boulevard Oak Bluffs MA 02557
Pending

MLS Number 39271

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 1.37

NEW CONSTRUCTION WITH A POOL & SPA, OAK BLUFFS Built in 2019 by a well-known Island contractor and designer, this sweet hidden pearl is elegant, private and relaxing. Conveniently located 3 miles from the triangle in Edgartown and 4 miles from downtown Oak Bluffs with bike paths in both directions, situated off a main road in a very quiet dead-end neighborhood with plenty of opportunities for biking in the woods and walking around neighborhood ponds. The 4,200 square feet contemporary house has a main floor with an open cathedral ceiling great room that overlooks the heated pool. Sliding glass doors lead to beautifully Zen landscaped exterior living space with areas for dining under an umbrella, sitting on the couch next to the pool, playing bean bag toss, grilling a steak, or sitting in the hot tub. Outdoor lighting allows for ultimate enjoyment of this magical oasis. Simple monolithic building shapes create minimalistic, peaceful respite for ultimate year-round escapes. Remarkably, this is not only an amazing place to gather, it is an amazing place to find reflection. Recharge, have adventures, inspire.

Listed by C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

26 Greenleaf Avenue Oak Bluffs MA 02557

Oak Bluffs, MA26 Greenleaf Avenue

Price$3,800,000

Est. Mortgage: $/month

Open House

MLS Number 39529

  • Residential
  • Next Open House: Sun 05/22 4:00 pm. to 6:00 pm.
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 3.5

How often do you find a property with three different water views -pond (Sunset Lake), harbor (Oak Bluffs) and ocean (Vineyard Sound). Location is everything, and this bungalow has it all. You can practically hear the children squeal with joy after catching the brass ring at the famous Flying Horses Carousel, and a front row seat on your wrap-around porch for the annual August fireworks. As close as it is to the ferry, beaches, restaurants, shops, and even the public library, this getaway perched on a hill in a quiet neighborhood allows for a peaceful cup of morning coffee on the side patio. Thoughtfully renovated by a popular local architect, this bright and cheery cottage provides plenty of room for multiple guests. Each of the unique 6 bedrooms makes clever use of space and natural light. When you think of a seaside getaway with all the amenities, this is what you picture. And if you want to share, there is a strong rental history.

Listed by C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

138 Edgartown Vineyard Haven Road Oak Bluffs MA 02557
Pending

MLS Number 39430

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 1.2

Luxury home very close to perfection with an oversized privately located lot in the center of the island includes most of the items in your checklist. Spectacular heated shotcrete pool with both a jacuzzi and a stone water fall is surrounded by a thermal bluestone deck. Adjacent to the pool is a stone fire pit perfect for gatherings, this backyard has all the bells and whistles. A beautiful fruit/vegetable garden includes pears, apples, blueberries, and strawberries. A large shed great for storage sits right next to the kids swing set playground, and you still have plenty of room in the yard perfect for entertainment. As you walk in the main house you find yourself amazed with the open concept full of luxury finishes in every corner. Large Master suite includes heated marble floors, and an attached three season porch. Entire house was recently renovated, including a high end finished basement! Solar panels come in handy to help assist with the continuing increase of the energy costs. Above the oversized heated newly constructed 3 car garage you will find a high end one bedroom apartment, and a separate art studio that can be also used as a home office if needed. This is the listing you have been waiting for!

Listed by Premiere Broker Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

24 Sumner Park Road Oak Bluffs MA 02557

Oak Bluffs, MA24 Sumner Park Road

Price$3,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 39265

  • MultiFamily
  • Bedrooms 12
  • Bathroom 10
  • Acreage 0.2

Unique Multi-Family in East Chop. Four units, 12 bedrooms in total. The units include a 7 bedrooms, 7 bath house - a 3 bedroom, 1 bath house and (2) studio apartments. Zoned B1, this property is a must-see to understand the opportunities it presents. Nestled privately, abutting East Chop Association land and open space in a prime location only a short distance to beaches, harbor, and downtown Oak Bluffs. The primary house is a two-story with 2,520+/- square feet and offers 7 bedrooms and 7 bathrooms, kitchen, open living and dining area and laundry /mud-room. There is tons of decking along the side and rear of the house for outside enjoyment. The back house was built in the 1950's and offers 1,500+/- square feet with 3 bedrooms and 1 bath, kitchen and open living and dining area with two story ceiling height and loft. (2) studio apartments, built in 1996, each offer 520 square feet of space with kitchen and full bath.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

34 Windemere Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Windemere Road

Price$3,200,000

Est. Mortgage: $/month

Open House

MLS Number 39595

  • Residential
  • Next Open House: Sat 05/28 3:00 pm. to 6:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3

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 the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has instore for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2022 to be transferred to Buyer at closing.

Listed by Island Home Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

79 Circuit Avenue Oak Bluffs MA 02557

Oak Bluffs, MA79 Circuit Avenue

Price$2,750,000

Est. Mortgage: $/month

MLS Number 39276

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 4
  • Acreage 0.1199

ICONIC OAK BLUFFS COTTAGE - This lovely two-story Victorian, built in 1875, has been occupied year-round since 1926. Home to several generations of families and now the iconic Good Dog Goods, 79 Circuit has always been a gathering place. With B1 zoning and past use as a family home, possibilities abound here. Good Dog Goods, beloved by furry ones and their humans for 22 years occupies the entirety of the first story with two office spaces above in the rear of the building. Above the front rooms of the store a one-bedroom cottage-classic apartment, so warm and welcoming with its captivating balcony trimmed in gingerbread, invites even the most discerning guests. A cozy studio graces the lower level. The soul replenishing sea air breezes up Pennacook Avenue inviting all to enjoy the quintessential porch culture of Oak Bluffs. While away the afternoon in a rocker watching the world go by, or sit and share an evening with loved ones. “The beauty of this lovely home is that it wraps its arms around all who come, whether to rest and recharge, play, work, live, or shop.” Come discover the exceptional soul of this cottage.

Listed by Portfolio Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

168 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA168 East Chop Drive

Price$2,650,000

Est. Mortgage: $/month

MLS Number 38342

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.0002

Dramatic Vineyard Sound Views on East Chop Drive - Charming cottage on desirable East Chop Drive - Enjoy spectacular views of Vineyard Sound & boats passing by from your front deck of this cozy Martha's Vineyard retreat. The cottage is just under 1,000 Sf and sits on 12,256 SF of land, and currently features 2 bedrooms and 1 bath. Permits are being prepared for the potential of a new 4 bedroom septic system. This setting offers unbelievable views from a remarkable location in Oak Bluffs.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

35 Temahigan Avenue Oak Bluffs MA 02557

Oak Bluffs, MA35 Temahigan Avenue

Price$2,250,000

Est. Mortgage: $/month

MLS Number 38062

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.63

Situated directly between Oak Bluffs & Vineyard Haven, this antique home has been in the same family for 4 generations. Enjoy water views of the Vineyard Haven harbor from the porch, primary bedroom, 3 season room, and living room. The first floor boasts high ceilings, a beach stone fireplace, the living room, dining room with built-in cabinets, kitchen, full bath & mud/laundry room. The second floor has 4 bedrooms, a full bath, and a 3 season room. The main house also has two decks perfect for outdoor entertaining while watching the sunset over west chop. Additional living space is in the detached bungalow that has a living area, kitchenette, full bath & loft area. Additional amenities include a separate shed and 1 car garage/boat storage. 5 bedroom Title V septic has been inspected and passed. A home inspection report by John Talanian is available upon request. Potentially enough room for a pool. Sellers do not make any representations or provide warranties regarding the potential use of the property. Buyers are responsible to perform their own due diligence.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

67 Madison Avenue Oak Bluffs MA 02557

Oak Bluffs, MA67 Madison Avenue

Price$2,200,000

Est. Mortgage: $/month

MLS Number 39587

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.65

Rare East Chop Opportunity – Nestled on the corner of Madison and Green Avenues is a vintage two-story summer home with all the charm of a by-gone era. A superb location, only one block from the East Chop Tennis Club, two blocks from the East Chop Lighthouse and gorgeous bluff views. Ownership of this address provides East Chop Membership access. Explore the opportunities that exist; the large acreage allows room for additional building and expansion. The central hub of the home is the dining room, flanked by a living room with fireplace on one side and a cozy den with bath on the other. The kitchen is conveniently located off the dining room and has access to the backyard and outdoor shower. Four bedrooms and a shared bath are on the second level and feature vaulted ceilings with exposed rafters. The screened porch and stone patio are the perfect places to enjoy the tranquil and private setting. East Chop is a quintessential, close-knit community only a short distance from the harbor and downtown Oak Bluffs.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

34 Double Ox Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Double Ox Road

Price$1,895,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38667

  • Residential
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.3784

NEW LISTING in LAGOON RIDGE: TO BE BUILT on LOT 14 NAUSHON STYLE HOME~ Featuring 3 bedrooms and 3 ½ bathrooms, offering over 2,400 square feet of living space, the Naushon is the flagship of the Homes at Lagoon Ridge. A grand, covered wrap-around porch with beautiful board and batten siding high lighted with an attractive metal roof at the front of the home heightens one’s sense of arrival and provides the perfect setting for enjoying those cool summer breezes and refreshing morning air. The Naushon leverages a smart and efficient floor plan that connects its chef’s kitchen to living and dining areas to form a generous space to host large gatherings of family and friends where life-long memories will be made. All three-bedroom suites feature tiled ensuite bathrooms with quartz surfaces, Kohler fixtures, and spacious closets, while the Naushon’s second floor suites offer the option for private bedroom balconies. The Naushon’s classic lines pay homage to the cottage history of Oak Bluffs while offering all of the benefits of modern technology and comfort. The Naushon is the realization of your island dream. **See Interactive Virtual Tour Attached ** See Lagoon Ridge Website** Many upgrades and options available **Call for an appointment and private tour. Don't wait RESERVE YOUR HOME TODAY! THERE ARE 9 HOMES CURRENTLY UNDER CONTRACT/SALE PENDING~

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

28 Grovedale Road Oak Bluffs MA 02557

Oak Bluffs, MA28 Grovedale Road

Price$1,700,000

Est. Mortgage: $/month

Pending

MLS Number 39241

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.25

NEW CONSTRUCTION, contemporary farmhouse style home with wrap around deck and outdoor shower. This home features a first floor en-suite bedroom with a full bath, a half bath off the foyer entry, an open kitchen/dining and living room area with a gas fireplace, with the rear wall sporting walls of glass with the sliding glass doors from both the dining area and living room area. There is a well designed mudroom area with a first floor laundry, a large overflow pantry and a built in bench seating area. The second offers two en-suite bedrooms, a large second floor living room area and a second laundry area. A full poured foundation with a walk out door completes this new construction offering. The property is located close to the Lagoon, and close to downtown.

Listed by Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of May 22, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."