Recently Listed Oak Bluffs MA Real Estate

View the newest listings in Oak Bluffs on Martha's Vineyard below. You may also be interested in browsing all current Oak Bluffs real estate listings.

New Listings Oak Bluffs

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

Time Saving Tip - Sign up for a search account (it's free) to save your favorite Martha's Vineyard real estate listings and get notified when similar properties become available.

Learn about the town of Oak Bluffs >>

6 Little Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA6 Little Pond Road

Price$2,100,000

Est. Mortgage: $/month

Open House

MLS Number 39508

  • Residential
  • Next Open House: Fri 07/1 11:00 am. to 1:00 pm.
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1

An oasis of tranquility awaits you at this "end of the road" setting. Central yet tucked away, this custom built, cross-gabled crafted homestead truly takes advantage of its location. Surrounded by conservation land, including Tisbury Meadows, Greenlands Preserve, Wapatequa Woods, Thimble Farm and the picturesque Little Duarte's Pond - all yours to enjoy and explore. A welcoming front yard with abundant gardens, porch deck and a central entrance that leads the way into grand spaces. Stately and inviting with rich details throughout - the expanse of the intersecting great rooms offer spacious entertaining options and pizzazz! Large banks of windows allow the light to stream in from every direction. Impressive chef's kitchen with a beautifully crafted wood ceiling and terrific kitchen bar. Thoughtful design includes the ever-important mudroom area and interior access to the basement. Open dining room, living room with fireplace hearth and the dramatic beamed vaulted ceiling sets the pace. First floor bedroom has a surround of windows and glass doors that seems to bring the outside in. Large bathroom with bead board, vintage fixtures, soak tub, tiled shower and bidet. Stunning helical wooden staircase seems to float as it reaches to the second level with wrap around railings. Second floor has a bedroom suite as well as a multitasking office/guest nook and creative storage. Eastside deck with fenced yard, ornamental pond and nearby garden shed. Westward views of abutting conservation lands and the large acreage allows for a garage, pool, guesthouse and potential further development. Lush plantings, flowering trees and perennial gardens surrounding the house are ever evolving with the seasons. With well managed systems, a full basement and room for expansion. Showings begin Friday July 1st.

Listed by Helena Kirschenbaum of Compass | MV Team

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

90 Meadow Avenue Oak Bluffs MA 02557

Oak Bluffs, MA90 Meadow Avenue

Price$2,495,000

Est. Mortgage: $/month

MLS Number 39785

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.3499

Coastal living on East Chop! This well renovated, year-round, bungalow "cottage" is full of contemporary creature comforts, but honors the character and charm of "old Vineyard living". The architectural style draws one immediately to the wrap around porch, and upon entering the home, the sparkling vintage fir floors, beadboard wainscoting and beach stone fireplace with stove insert take you back to a simpler time. The three bedroom, two bath Main has house has received upgrades throughout to include; Daiken heating-HVAC system, Rinnai On-Demand hot water system, HDMI/Cat 5 and electrical systems, Lutron lighting, insulation, bathroom improvements, and a full kitchen makeover with Fischer-Paykel and Bosch appliances, in addition to the exterior spaces involving the outdoor shower, porch and decking areas. The detached one bedroom, one bath, guest cottage is light filled, spacious, with a mini-split heat & A/C, and a kitchenette. And the former garden shed is now a terrific, light-filled "flex space" with hardwoods, insulation and electricity. The property is professionally landscaped with mature plantings, a well manicured lawn and irrigation. It is being sold "turn-key" and has strong rental potential. Come and experience "Vineyard charm" on East Chop!

Listed by Sean Federowicz of Landmarks at TODAY Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

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. Showings begin July 1st.

Listed by Michele Casavant of Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

16 West Clinton Avenue Oak Bluffs MA 02557
Open House

MLS Number 39663

  • Residential
  • Next Open House: Sat 07/9 11:00 am. to 1:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5

Open House Saturday July 9th & Sunday July 10th 11 am - 1pm OAK BLUFFS Classic 4 Bedroom 1.5 Beautiful Victorian located in the Historic Martha's Vineyard Camp Meeting Association on desirable West Clinton Avenue with Inviting Views overlooking Oak Park. This Cottage is filled with Victorian Charm and Attractive Gingerbread Detail. A Terrific In -Town LOCATION... easy stroll to ART'S District, Oak Bluffs Harbor, Beaches, Ferries, Galleries and Restaurants! Exceptional offering with the perfect flow for both Summer living and entertainment. A first floor bedroom with bath and Dazzling Diamond Windows throughout! For more information on the Martha's Vineyard Camp-Meeting Association please visit www.mvcma.org .

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

17 Beach Road Oak Bluffs MA 02557

Oak Bluffs, MA17 Beach Road

Price$1,925,000

Est. Mortgage: $/month

Active With Contract

MLS Number 39735

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2899

OAK BLUFFS WATERFRONT WITH DOCK- Spectacular frontage and views of Vineyard Haven Harbor are achieved from this classic three-bedroom, two-bath home. The charming cottage has been well maintained and offers a practical layout that will easily accommodate all who visit. However, not much time will be spent indoors, with your days filled with boating, fishing, swimming, and everything in between, and your evenings enhanced by spectacular sunsets over West Chop and beyond. The additional vacant abutting parcel, included in this offering, provides extra privacy and water frontage. A Vineyard classic that can’t be missed!

Listed by Katherine Donahue of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

66 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA66 Canonicus Avenue

Price$950,000

Est. Mortgage: $/month

MLS Number 39563

  • Residential
  • Mls Status Active
  • Bedrooms 1
  • Bathroom 1
  • Acreage 0.23

Adorable Oak Bluffs Cottage "The Pinkeltink " located in a family- friendly setting on desirable Canonicus Avenue abutting serene salt marsh where there are singing Pinkeltinks in the early Spring along with an aviary of assorted birdlife including Red Wing Black Birds along with a variety of colorful natural vegitation. Easy walk or bike ride to Sandy Beaches, Town Parks, Circuit Avenue and Ferry Ports. **please see attached Title 5 official Report ** System failed and is a Cesspool* Buyer is responsible for upgrade seller is selling as is.. Buyer should confirm any possible upgrades and or expansion possibilities with the Town of Oak Bluffs.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

31 Second Avenue Oak Bluffs MA 02557

Oak Bluffs, MA31 Second Avenue

Price$575,000

Est. Mortgage: $/month

MLS Number 39703

  • Land
  • Mls Status Active
  • Acreage 0.28

Close to Oak Bluffs center and harbor. This lot has been staked and survey.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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 Lincoln Avenue Oak Bluffs MA 02557

Oak Bluffs, MA20 Lincoln Avenue

Price$779,000

Est. Mortgage: $/month

Pending

MLS Number 39697

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 1.5

This wonderful fully winterized and updated campground cottage was built in 1869 and is house tucked behind town. Nice spaces and easy living in town this is a great place to call home. Sellers did a number of significant upgrades making this home comfortable year-round and it has a full basement with oil heat. In fantastic condition it is ready to move into and available this summer. 3 bedrooms and 1.5 baths, there is a double living room and separate dining area which walks out to a screened in porch. 1 minute from your favorite OB restaurants, this home is the epitome of convenient. Living in the MVCMA provides wonderful opportunities for community, activities, arts and culture. One of the best and most affordable 3 bedroom homes on Martha's Vineyard under 1 million dollars.

Listed by Jim Feiner of Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

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 Cassie Bradley of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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: 5.7% last updated on Jun 30, 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

8 Dreamers Way Oak Bluffs MA 02557

Oak Bluffs, MA8 Dreamers Way

Price$1,399,999

Est. Mortgage: $/month

MLS Number 39687

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 3
  • Acreage 0.3

IMPRESSIVE! Spacious!! Almost 2,000 s/f of living space and everything in this home shows like NEW! The foyer invites you into a nicely appointed open floor plan where you will find a delightfully large kitchen with ample counter space and maple cabinets. This room seamlessly connects to the dining area and a large, open great room with wood burning stove. Hardwood floors throughout this space as well as 10 foot ceilings make the room open and inviting. Plenty of versatility and styling options to make this space your own (Furniture is negotiable). Sliding glass doors from both the kitchen and living room lead to a large, wrap around deck that overlooks the nicely manicured yard and provides access to an oversize, custom, outdoor shower. A spacious Primary Bedroom features an en suite bathroom with double sinks, quartz counter tops, beautifully tiled shower and a large walk-in closet. Primary bath also has a hook-up for a second washer and dryer. Across from the primary bedroom you will find a 2nd bedroom also with a large over-sized walk-in closet. To round everything out, there is a lower level 24' X 22' media room, an additional bonus room/den/office area, the third full bathroom, and a two car heated garage with a separate workshop and a utility room. A new air-conditioning system installed last year. Centrally located on a quiet side street that provides easy access to Circuit Ave, Beaches and all Island Towns! Thoughtful, custom touches throughout the home. **BONUS!!** Seller has finalized a new two bedroom septic design (subject to approval by the Board of Health).

Listed by Sheila Morse of Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

6 First Avenue Oak Bluffs MA 02557

Oak Bluffs, MA6 First Avenue

Price$800,000

Est. Mortgage: $/month

MLS Number 39692

  • MultiFamily
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.23

Two family home only a half mile from the Harbor and all the action on Circuit Ave in down town Oak Bluffs. Priced to sell in this ascending real estate market on the island of Martha’s Vineyard. Property is being sold “as is” and 'seller makes no representations or warranties”.

Listed by Nic Korba of Landmarks at TODAY Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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 July 1, 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."

beach entrance beach entrance
Ocean Park Realty Incorporated Logo

We would love to hear from you.

Say Hello

Contact Us

You deserve to live in the home of your dreams and we want to help facilitate that process. Contact us for more details.

Ocean Park Realty Incorporated Logo

Stay Updated

Send a Message