Oak Bluffs Homes for Sale

If you are looking to purchase a home the town of Oak Bluffs, Breakwater is here to assist you along the way. You will find listings in the famous Martha's Vineyard Camp Grounds "Gingerbread cottages",  along Ocean Park, or on East Chop as well as other areas within the Village.  Purchasing a home in this classic beach town can range from a small summer cottage to a luxury waterfront home.   

Find Homes For Sale in Oak Bluffs

Contact us if you have any questions, or if you would like to schedule a showing. Create an account to save favorite listings and to receive email notifications when similar listings 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 Michele Casavant of Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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$9,750,000

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 Cassie Bradley of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

400 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA400 Barnes Road

Price$7,300,000

Est. Mortgage: $/month

Open House

MLS Number 40141

  • Residential
  • Next Open House: Sun 10/9 11:00 am. to 3:00 pm.
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 5.5

Welcome to 400 Barnes Road, Oak Bluffs. This stunning contemporary is lavish with architectural design. Every detail was thoughtfully selected to provide the ultimate luxurious experience. The quality of materials used to build this home are unmatched by any other property currently on island. The elevator travels silently to each floor and opens to the oasis of every living area. There are over 7000 square feet of open living space with multiple rooms connecting and flowing effortlessly throughout the 3 levels of the home. The distinctive interior features high-end materials and appliances, designer lighting fixtures and a chef's open kitchen. High ceilings and full length windows with motorized privacy shades let in tons of natural light during the day and feature magnificent sunsets in the evening. The media room full bar area with wine cellar and the gym are truly a must see.. On the exterior you will find relaxation at its finest with beautiful infinity pool with access to the pond for Boating and other Water activities -

Listed by Scott Lewis of Lewis Real Estate Services,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

4 Troy Street Oak Bluffs MA 02557

Oak Bluffs, MA4 Troy Street

Price$5,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 40000

  • MultiFamily
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.8386

Standing majestically on this beautiful double lot overlooking Vineyard Sound is this distinctive Victorian style home that incorporates the best of the new and old-world design. The home offers multiple patios, porches, decks and balconies from which to enjoy the lovely view over to Falmouth, a vintage wine tasting library, formal and informal living areas as well as a workout room and recreational room in the basement with a full-service bar area and media area in which to entertain guests and family on movie nights. The home offers two large, beautiful primary suites as well as 2 large guest bedrooms and a full third floor with lots of sleeping area for the kids. There is a four-season porch with a mini split for year-round enjoyment. Built in sound system. In addition to the main house there is a separate guest house which offers full privacy from the main house, its own deck, shower, a guest bedroom with a balcony, living room, full kitchen and a 2-car heated garage. Please note that the finished basement and third floor represent another 3538 sq feet for a total of 7103 sq ft of finished space. Hot Tub on the back deck is included with the sale and the lovely furnishings package is negotiable.

Listed by Jean Kelleher of Kelleher R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$4,995,000

Est. Mortgage: $/month

Pending

MLS Number 38557

  • Residential
  • Mls Status Pending
  • 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 Marilyn Moses Cell 617-462-0381 ANYTIME ! of Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 JoJo Lambert of Island Home Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 Antulio Goncalves 774-232-0059 of Premiere Broker Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

19 Ocean Avenue Oak Bluffs MA 02557

Oak Bluffs, MA19 Ocean Avenue

Price$3,000,000

Est. Mortgage: $/month

MLS Number 38735

  • Residential
  • 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 Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 Fred Mascolo of Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

20 East Side Road Oak Bluffs MA 02557

Oak Bluffs, MA20 East Side Road

Price$2,900,000

Est. Mortgage: $/month

MLS Number 40165

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.3901

The property boasts of an expansive Lagoon Waterfront and stunning sunsets that take your breath away. There are a few steps to small beach area for sunbathing, swiming or kayaking. There is also a transfer of a mooring that is included in the sale. Buyer pays annual fee. Open floor plan includes modern kitchen with two ovens, granite counters and custom glass-front cabinets. A center-piece stone wood-burning fireplace graces the living room, kitchen and dining area. French doors lead out to the deck area for relaxing, dining, or just taking in the view. The first floor has two bedrooms and a full bath. Kitchen area also has a pantry and wide hallway leading to upstairs. The second floor primary bedroom has sweeping views of the Lagoon and shares a full bath with another room that can be a bedroom or study. Tons of closet space along the hallway.There are lovely architectural details throughout the home designed by Bruce MacNelly. This desirable location is only a little over a mile to either Vineyard Haven or Oak Bluffs. Bus line and bike paths are at the end of the road for easy access to all Island locations. Mini- splits are located throughout the home. The laundry area is located in a large basement which also houses a work area and a walk-in owners cedar closet.

Listed by Joanna Fairchild 617-413-8681 of eXp Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 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, including the option to return to a Single Family dwelling. Good Dog Goods, beloved by furry ones and their humans for 22 years, currently 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 Leslie C. Floyd 508-221-4643 of Portfolio Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

"Based on information submitted to MA_LINKMV as of October 5, 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."