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.

267 Farm Neck Way Oak Bluffs MA 02557

Oak Bluffs, MA267 Farm Neck Way

Price$15,500,000

Est. Mortgage: $/month

MLS Number 39712

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 7.5
  • Acreage 2.11

A RARE OFFERING, a merger of water views and unparalleled views of fairways at FARM NECK, a world premier golf course and club. This offering comes with an immediate STOCKHOLDER MEMBERSHIP! The architecturally designed home is in excess of 10,000 sf of exquisite living space, providing 5 bedrooms, 9 bathrooms, masonry fireplace, home gym, game room, and home office, an expansive heated pool and hot tub, outdoor grill area, five 2nd floor decks, a 3 car garage, and a private dock on Sengekontacket Pond. The combination of Golf, Water Access and an Exquisite Home offers endless options for enjoyment. Upon entry you are greeted with layered water views from Sengekontacket Pond, to Nantucket Sound, to the Edgartown Outer Harbor and beyond to the North Neck Cliffs of Chappaquiddick. A true feast for the eyes! The architectural marvel of curves within the home, is a repeating element throughout. The foyer, dining room, living room bar, and home office all echo the repetition of circular curvatures and movement throughout.This circular motif repeats in the upper floors suspended stairways and hallway areas bringing one's eyes to curved windows and curved doorways.The home is centered around the large round dining room with its 2 story curved wall of windows and curved custom built in cabinetry. The circular motion of the dining room lends itself to easy and comfortable movement to the gourmet kitchen, the family room with its fieldstone fireplace, the home office and then to the crown jewel, the vast, outdoor entertaining area. The outdoor entertaining features a round hot tub and round half moon area at the head of the heated gunite pool. Numerous lounge areas offer spaces to absorb and enjoy the exquisite surroundings. This is a home where one gathers to soak up the sun, absorb the vistas, play amongst the water sports on Sengekontacket and immerse themselves in the GOLF offered at FARM NECK. Each bedroom has its own private bath. Two of the guest en-suites have their own private deck with spectacular views overlooking the outdoor entertaining area, fairways and the layered water views beyond. A true feast for the eyes. The attached private apartment offers its own kitchen, dining and living room space. Come to experience, come to stay, come to buy.

Listed by Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

14 Tylers Creek Oak Bluffs MA 02557

Oak Bluffs, MA14 Tylers Creek

Price$12,000,000

Est. Mortgage: $/month

MLS Number 39576

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 5.5
  • Acreage 2.56

Private Farm Neck Retreat. Situated at the end of Tylers Creek this property offers expansive water views of Sengekontacket Pond and the surrounding golf course. The floor to ceiling windows in the large living room allow you to experience the views of the Pond as soon as you enter the home. The primary bedroom is in its own wing on the first floor and is complete with two office spaces, a full bathroom that flows effortlessly outside to the hot tub and outdoor shower, and many beautifully crafted built-ins for storage. The large kitchen is flanked by a formal dining room on one side and a sunny more casual dining nook on the other. Both allowing for large gatherings and impressive views. The remaining three bedrooms are located on the second floor, each with a private bath, and views of Sengy. The finished basement with movie theater and game room completes this Vineyard retreat.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

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: 4.99% last updated on Aug 4, 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$3,585,000

Est. Mortgage: $/month

Pending

MLS Number 39529

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathroom 3.5
  • Acreage 0.11

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: 4.99% last updated on Aug 4, 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

MLS Number 39595

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.72

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 in store 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. I will be doing showings only on Sunday from 12:00pm until 2:30pm during the rental season.

Listed by Island Home Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

24 Sumner Park Road Oak Bluffs MA 02557

Oak Bluffs, MA24 Sumner Park Road

Price$3,200,000

Est. Mortgage: $/month

Pending

MLS Number 39265

  • MultiFamily
  • Mls Status Pending
  • 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: 4.99% last updated on Aug 4, 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

MLS Number 39430

  • Residential
  • Mls Status Active
  • 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: 4.99% last updated on Aug 4, 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

4 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 High Meadow Lane

Price$3,000,000

Est. Mortgage: $/month

MLS Number 39624

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.8899

This incredibly insulated sun bathed SIP Post and Beam is state of the art Vineyard living. A 5 bedroom septic in the ground this 4 bedroom 4.5 bath home is finished magnificently! Central a/c and radiant heat through the floors make for perfect temperature control of whatever you desire! Mature landscaping with a large garage and bonus room over the garage there is room for everyone. The master bedroom suite is ground level and has a wonderful large bath/spa area. If furnishings are agreeable they can be negotiated and this home could be sold turn key! A must see!

Listed by Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

19 Ocean Avenue Oak Bluffs MA 02557

Oak Bluffs, MA19 Ocean Avenue

Price$3,000,000

Est. Mortgage: $/month

MLS Number 38735

  • MultiFamily
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 3.5
  • Acreage 0.0699

Ocean Park Beauty: This historic home on Ocean Park has been loving maintained and ready to pass along to the next generation. The four season two-family home is equipped With 2 separate kitchens, living areas, and dining rooms. There is plenty of space for the whole family with seven bedrooms, 3.5 bathrooms, and 2 large porches. The views of Ocean Park and the Sea beyond are spectacular. Conveniently located amongst shops, restaurants, and beaches. Houses on the park don't come up for sale often so don't miss your chance to own this amazing home with a great rental history.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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 Narragansett Avenue Oak Bluffs MA 02557

Oak Bluffs, MA28 Narragansett Avenue

Price$2,750,000

Est. Mortgage: $/month

MLS Number 39849

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 4
  • Acreage 0.1

This historic home, with over 3,000 square feet of interior space, nine bedrooms and four bathrooms. Sitting on a corner lot on Narragansett Avenues with a direct view of Ocean Park. Conveniently located close to shops and restaurants, and only steps away from Inkwell beach. Renovated top to bottom in 2022. All new and with a great rental history. The house features a double living room stone decorative fireplace, large dining area. and kitchen with exposed brick wall. The first floor has a private primary suite with separate entrances. This suite includes a sitting area, bedroom, kitchen, and bathroom. There is a second, first floor bedroom, a Laundry area and bathroom. On the 2nd floor are seven additional bedrooms, four with private balconies, two bathrooms and storage room. The grand front wrap-around porch with many seating areas. A private gravel driveway for 2 cars, a large back deck with BBQ grill with seating, and an outdoor shower complete the yard.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

79 Circuit Avenue Oak Bluffs MA 02557

Oak Bluffs, MA79 Circuit Avenue

Price$2,750,000

Est. Mortgage: $/month

MLS Number 39276

  • MultiFamily
  • Mls Status Active
  • Bedrooms 4
  • 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: 4.99% last updated on Aug 4, 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

25 Harthaven Road Oak Bluffs MA 02557

Oak Bluffs, MA25 Harthaven Road

Price$2,700,000

Est. Mortgage: $/month

Open House

MLS Number 39790

  • Residential
  • Next Open House: Sat 08/13 1:00 pm. to 3:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5

Harthaven ~ An opportunity that doesn't come often! An expanded Cape in pristine condition with over 3,500s/f, 4 spacious bedrooms, 3.5 baths, great room, large cook's kitchen, dining area plus cozy den. The location and amenities included in Harthaven are exceptional and especially unique for a down-island property. No longer will finding parking at the beach be an issue as this includes use of an expansive private association Nantucket Sound beach, access to Farm Pond and neighborhood tennis/pickleball courts are steps away. Bike or walk into OB on the path at the entrance of the neighborhood. Privacy, summer amenities and proximity to town make for the ultimate vacation retreat!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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 August 8, 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."