Oak Bluffs Private Homes

Scroll down to find the latest private homes for sale in Martha's Vineyard, MA's town of Oak Bluffs. Look through a variety of listings to find your new home. Register with our site to save your favorite properties, and you can get email updates when new listings match your search criteria. For more information, questions, or to schedule a showing, please contact us today!

43 Tiffany Drive Oak Bluffs MA

Price$983,000

Est. Mortgage: $/month

MLS Number 35833

  • Residential
  • Square Feet 2114
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

This handsome 4-bedroom home has deeded access on the Lagoon for swimming and boating just a short distance away. The whole 3-story home has wonderful light through skylights and an abundance of windows. There are separate living spaces on each of the 3 floors; an updated kitchen with handsome cabinetry, a big island and soapstone countertops; nicely-sized guest bedrooms and a lovely, large master suite. Within the last year the owner has replaced flooring and carpeting, installed 8 HVAC units, painted the interior throughout, installed new hardscape and gardens and more! The owner tells me she loves the access to the trails of the Southern Woodlands - one which leads right over to the YMCA. The 1.65 acre lot offers an abundance of privacy and the detached 2-car garage, with its big finished space above and separate driveway, would make an excellent office or studio.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

58 Barnes Road Oak Bluffs MA

Price$650,000

Est. Mortgage: $/month

MLS Number 35546

  • Residential
  • Square Feet 1428
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.23

This charming Oak Bluffs home is perfectly located in close proximity to downtown Oak Bluffs, Vineyard Haven, and the Sailing Camp. The farmers porch spans the front of the home, and with the privacy of the mature trees is a great spot to sit any time of day. As you enter the front door you walk into an open kitchen, dining room and living area great for everyone to gather in. The second floor, while at the moment is two open rooms set up as bedrooms, could be made into two more private bedrooms or one large master suite. There is a full basement that holds the laundry and other storage, but could be finished off for additional living space. Whether you are looking for a property to rent out, use as a family, or renovate, this home has a lot of potential for any buyer.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

72 Norris Avenue Oak Bluffs MA

Price$899,000

Est. Mortgage: $/month

MLS Number 35426

  • Residential
  • Square Feet 1765
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.23

This well maintained home has it all! It's perfect for entertaining and convenient to town. Enjoy dinner and a movie, cocktails on the harbor, shopping or catch your ferry, all just a short 5 minute walk from the home. This corner lot is surrounded by landscaping giving you a sense of privacy. Invite friends over for a cookout and enjoy the outdoor fireplace on the chillier nights, or practice your putting game on the green (just don't get caught in the sand trap). If the day gets rained out you can always bring the party inside with the open concept living area and sun room. A smart choice for someone looking for an investment property or someone looking for their Martha's Vineyard home.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

1 Bird Street Oak Bluffs MA

Price$1,159,000

Est. Mortgage: $/month

MLS Number 34308

  • Residential
  • Square Feet 2472
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.22

Location! Location! A short 5 minute walk to the ferry, movie theater, town, beach, harbor and library. Come view this private gorgeous newly renovated Cape style home featuring (4) bedroom (3) full baths, attached garage and over 2400 SF of living space. This pristine open concept home includes custom white kitchen cabinets with quartz countertops, center island with seating and a separate eat-in dining area. The kitchen space flows into an oversized family great room. The first floor includes 2 sunny bedrooms with glass patio doors that open onto a private relaxing side deck overlooking the side yard and custom Japanese gardens. The second floor is comprised of brand new construction that includes 2 master bedroom suites with large walk-in closets and 2 modern tiled bathrooms. The home radiates with morning and afternoon sun. Property includes a brand new private custom cedar outdoor shower and a new extra wide driveway with a cobblestone apron. The yard is surrounded by mature plantings that bring color all season long and plenty of privacy. This property is a the perfect investors dream or family Vineyard getaway!

Listed by Premier Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

53 Tia Anna Lane Oak Bluffs MA

Price$2,550,000

Est. Mortgage: $/month

MLS Number 34752

  • Residential
  • Square Feet 2442
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1

Never miss a sunset from this custom built waterfront home! Beautifully designed by Breese Architects with a focus on the stunning water views from each room, this three bedroom, three bath home is the perfect property for entertaining family and friends. Set on one acre of land with stairs to the Lagoon for easy water access and a large, grassy lawn area for all your summer games. The custom built home has a lovely open living space with a field stone gas fireplace anchoring the living room, french doors off of the dining area to the deck and an open kitchen with stainless steel appliances, custom cabinetry and granite counter tops. A second floor Master Bedroom Suite is the only room on this level, with water views from the private balcony, a spacious master bath with double vanity, tile floor and heated towel rack and an office/study area off of the bedroom. There are two guest room wings on the first floor along with two full bathrooms, offering your guests plenty of privacy. A den with built-in bookshelves has access to the loft with a private office space. Finishing off this well designed home is the laundry and mud room with access to a casual side door entry~perfect for coming in off the water. Enjoy the beauty of the Island right from your very own home!

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

42 Paddock Road Oak Bluffs MA

Price$1,999,000

Est. Mortgage: $/month

MLS Number 35025

  • Residential
  • Square Feet 4200
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

OAK BLUFFS - new, luxury enclave - The Preserve at the Woodlands! Enjoy the best of both worlds in this lovely area abutting 200 acres of conservation land yet centrally located off County Road near Farm Neck Golf Club with bike paths that provide EASY ACCESS into downtown Oak Bluffs, Edgartown and Vineyard Haven. Relax and enjoy POND VIEWS and panoramic meadow views. This HIGH QUALITY NEW CONSTRUCTION offers 5 bedrooms and 4.5 bathrooms with 9 foot high ceilings. The wooded 1.8 acre lot offers a spacious backyard with a bluestone patio for entertaining, outdoor shower and borders conservation land for complete privacy. The option to add a POOL is available upon request. An OPEN FLOOR PLAN features a large gourmet kitchen with a Sub-Zero fridge, Wolf range and other professional stainless steel appliances. The living and dining area has lovely views of the pond, custom built-ins and a gas fireplace. A first floor master bedroom contains an en suite bath, dressing area and walk-in closet. For your convenience, there is a first floor laundry room, mud room and powder room. Upstairs there are four SPACIOUS bedrooms - two of which are master bedrooms with en suite baths and vaulted ceilings. The two additional bedrooms share a hallway bathroom with double sinks. Two of the bedrooms offer pond views. There is a set up for an additional washer and dryer upstairs. Enjoy UP-ISLAND PRIVACY with DOWN-ISLAND CONVENIENCE! Don't miss this opportunity to enjoy this beautiful INVESTMENT property and begin to earn income right away. Or enjoy it all year round yourself with family and friends!! MOVE IN READY!!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

15 Peter M. Williamson Boulevard Oak Bluffs MA

MLS Number 34857

  • Residential
  • Square Feet 3100
  • Bedrooms 6
  • Bathroom 5
  • Half Bath 1

BRAND NEW!!! Custom design will be Ready for Occupancy this SEASON. Features over 3100 square feet with another 1000 in finished walkout basement including another bedroom. Beautiful marble/tile work in all bathrooms, wide oak hardwood flooring, gas fireplace with marble mantle, first floor en suite master, 8' sliders with access to sweeping deck, 9' ceilings and cathedral in the living room, and an open kitchen/dining area with Wolf stove, Sub Zero fridge, Bosch dishwasher, large center island. Also, attached 2 car garage with unfinished space above. This house flows comfortably through the intimate spaces offering easy living, privacy, and the yard has room for a pool. A must see!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

27 Bayes Hill Road Oak Bluffs MA

Price$1,175,000

Est. Mortgage: $/month

MLS Number 34713

  • Residential
  • Square Feet 3500
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

A builder's own custom colonial home nestled in a private setting of the Bayes Hill Association in Oak Bluffs. A desirable community of substantial homes with private tennis and easy access to the Lagoon & Sailing Camp. This home is situated on a .76 acre lot with an abundance of mature landscaping offering privacy. This home comfortably accomodates multi-family living with its four floors of finished space. A spacious open kitchen with a eat-in bar and lots of cabinetry and dining area leading to the a TV room which includes custom built-ins for storage. The first floor also has a gracious living room with a woodburning fireplace and a formal dining room (or could be a 1st fl bdrm) with glass doors that lead to the back deck and patio area. The second floor is comprised of a master bedroom suite , three guest bedrooms with a shared bath, and a separate wing that functions as a perfect “in- law suite” or 2nd master suite. The suite is complemented with a beautiful atrium window, wet bar and full bathroom. Designed for year around living, with gas FHA heating zones and central A/C,ample storage ,huge garage and laundry room with sink and built- in ironing station. In addition, the attic has been converted into a spacious & bright office space with large skylights and built in shelving. The basement is fully finished with a second washer / dryer & bath - living room with wet bar area and plenty of storage. Well sited on the lot, with a back deck, patio, big yard and garden.Surrounded by an abundance of mature trees and colorful rhododendroms & hydrangeas with irrigation. This home was thoughtfully designed to comfortably accommodate all the family and friends that will come to visit!

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

507 Barnes Road Oak Bluffs MA

Price$889,000

Est. Mortgage: $/month

MLS Number 33389

  • Residential
  • Square Feet 2592
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.3842

COUNTRY LIVING in a location within about a 5 minute drive to 3 towns. A convenient central "down-island" location (Oak Bluffs-Barnes Road), complete with a 2 level 24' x 30' Horse Barn, Main house with full basement and an oversized Garage plus enclosed storage area, all on 1.38 acres of land abutting 35.3 acres of conservation land. Great property for anyone that wants a large lot, abundant storage and a 4 bedroom house, all within a 5 minute drive to town or the Ferry. Much of the value lies in the excellent location, degree of privacy, amount of land, and Brand New 4 bedroom Septic System has just been installed. Very close to Featherstone Art Gallery and the Lagoon Pond Herring Run. Only minutes to the VH Ferry. Great property for those wanting extra land and privacy in a convenient location. Please call a minimum of 24 hrs. before a requested showing. House occupied and security device is active.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

View Our

Recommended Searches

View Categories