Oak Bluffs Homes for Sale

From charming Cape styles to classic Colonials, you’ll find a great selection of homes in Oak Bluffs. No matter if you’re looking for a summer home or year-round residence, you’ll find some great options to choose from on Martha’s Vineyard. Find current homes for sale in Oak Bluffs below.

Houses for Sale in Oak Bluffs MA

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220 East Chop Drive

Oak Bluffs, MA220 East Chop Drive

Price$1,995,000

Est. Mortgage: $/month

MLS ID 37706

  • Residential
  • MlsStatus Active
  • Square Feet 1977
  • Bedrooms 4
  • Bathrooms 2

Prime home in desirable East Chop diagonally across from one of the Vineyard's most photogenic lighthouses, the East Chop Light. With dramatic views from this uniquely designed 4-bedroom, 2 ½ bathroom, year-round or vacation house, this property should be at the top of your list if you're looking for water views, sunsets over West Chop, and close proximity to beaches, tennis courts, the Oak Bluffs harbor and downtown areas. The home -- known locally as "Pilot House", was built true to its name to replicate the bridge of a ship's Pilot House to allow the Captain views of a wide sweep of the sea. Wrap around decks off the second floor provide panoramic water views, in addition to the roof-top Widow's Walk which boasts 180-degree water views of Nantucket and Vineyard Sounds. Built to take advantage of the views, the second floor's open floor plan has walls of large windows in the living room, dining room and kitchen which provide ample water views, sunsets to the west, sunrises to the east and night-time starry evening viewing. A master bedroom and full bath complete the floor. First floor includes 3 bedrooms, and 1 ½ bathrooms, in addition to access to the basement storage areas and garage. Property includes outdoor shower, and parking for several cars on each side of the house. Title V septic certified 12/19/2020. Deck is in need of repairs/replacement and is the buyer's responsibility, as it can either be repaired or redesigned to suit the buyer's taste. The house is being sold fully furnished. The lot is large enough to allow for expansion of the house but please confirm any plans with appropriate town offices.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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4 Winemack Street

Oak Bluffs, MA4 Winemack Street

Price$695,000

Est. Mortgage: $/month

MLS ID 37702

  • Residential
  • MlsStatus Active
  • Square Feet 857
  • Bedrooms 2
  • Bathrooms 1

This charming vintage year-round insulated home, located on a quiet street, sits on a wooded, shaded lot surrounded by Rhododendrons. Features include wood floors throughout, recently updated kitchen with all new appliances, living room with wood burning stove for those cool, early spring and late fall days, and mini-split heat/AC on both floors for the winter and summer months and, a full bath on the first floor. Both bedrooms are on the second floor, with sitting room in between. Front porch, side deck, outdoor shower and shed complete the property. The house was reportedly moved from the Camp Ground behind the Summercamp (Wesley) Hotel in the 1920s-30s. Roof replaced in 2004. Title V installed in early 1990s, inspection passed 8-20-2015. Recent exterior improvements include painting the exterior trim and front porch, driveway moved and topped with pea stone, the yard landscaped and irrigation system installed. New hot water tank. Property is in R-1 zone, and lot is large enough to allow for expansion of the house with town approval.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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75 Carol Lane

Oak Bluffs, MA75 Carol Lane

Price$765,000

Est. Mortgage: $/month

MLS ID 37694

  • Residential
  • MlsStatus Active
  • Square Feet 1300
  • Bedrooms 3
  • Bathrooms 2

Don't miss this turnkey opportunity! Recently renovated and ready to move in, this 3 bedroom, 2 full bath ranch sits on .34 acres and features covered porch, ample patio space and a fully fenced yard with children's fort, swings and sandbox. Open-concept living room with vaulted ceiling and exposed beams adjoins modernized kitchen and dining area. Pergo wood laminate flooring throughout, with luxury vinyl tiling in kitchen and bathrooms. Master bedroom with ensuite bath, updated vanity, walk-in closet. Additional full bathroom features convenient, stacked laundry center, large updated vanity. 2018 improvements include new roof, gutters, all new windows, sliding door, new siding, patio and roofed porch and new on-demand propane furnace for heat and hot water. Central air-conditioning added in 2019. Newly constructed large, 10 x18 shed just completed. Walking distance to elementary school and less than 2 miles to the beach. Convenient circular drive and parking pad easily accommodate 4 cars. A great family home or vacation investment property, all major improvements have been done for you! Listing agent is related to sellers.

Listed by Upper Cape & Vineyard Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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309 County Road

Oak Bluffs, MA309 County Road

Price$1,289,000

Est. Mortgage: $/month

MLS ID 37448

  • Residential
  • MlsStatus Active
  • Bedrooms 4
  • Bathrooms 6
  • Acreage 0.38

The Opportunity You Have Been Waiting For! This conveniently located four-bedroom home is situated on a double size lot and offers space for everyone. The primary dwelling is four bedrooms and four full bathrooms. To the left of the foyer, there is a bedroom with a completely renovated luxurious bathroom. To the right of the foyer, there is a family room, wet bar, bedroom, full bathroom, and a private deck. Upstairs one will find an expansive family / living room, oversized bedroom, full bathroom, and kitchen. A large deck provides privacy and plenty of room for outdoor dining / lounging. The lower level offers additional living space, a large bedroom, a full bathroom, and a wet bar. The detached garage offers an oversized three-bay garage + office space above. There is a coin-operated laundry room, shed for additional storage, and plenty of parking. This property generated $142.8K of rental income in 2020.

Listed by Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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22 Rock Avenue

Oak Bluffs, MA22 Rock Avenue

Price$619,000

Est. Mortgage: $/month

MLS ID 37519

  • Residential
  • MlsStatus Active
  • Square Feet 826
  • Bedrooms 2
  • Bathrooms 1

Outstanding Vintage Sea Side Cottage! One block from harbor activities and summertime fun - minutes to ferries, beaches and all that is charming Oak Bluffs village. Association amenities and MVCMA community benefits are many in this treasured historic setting. Uniquely designed with decorative filagree scroll work and a rich history, this victorian cottage once served as the MVCMA cottage museum. Enter from the raised porch into the front parlor with high ceilings and clever use of space. Kitchen with pantry, a multi tasking bedroom/den and a full bath complete the first floor. High ceilinged second level has an enormous front bedroom with double doors plus another guest room both with beautiful wood floors and cross breeze windows. Impressive insulated roof renovations and a propane heater allow for comfortable three season use. The attached private deck adds a wonderful outdoor entertaining area to this vintage cottage home.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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25 Butler Avenue

Oak Bluffs, MA25 Butler Avenue

Price$635,000

Est. Mortgage: $/month

MLS ID 37510

  • Residential
  • MlsStatus Active
  • Square Feet 787
  • Bedrooms 2
  • Bathrooms 1

The Pink House: One of the most well-known cottages in the Martha's Vineyard Camp Meeting Association. The 2017 restoration includes refinished pine floors, new kitchen & appliances, total interior and exterior painting. Exterior paint was sanded down to bare wood and repainted in 2016 & 2017. Backyard with a new brick patio and stone alleyway installed. All four sides of the cottage are tongue and groove wood construction. Three gothic double doors (downstairs front & side, and front balcony), plus a stained window door (side balcony). The cottage is brighter than most with a unique picture window in the living area. This well-maintained cottage is being sold Turn-Key including the artwork!

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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29 Bayes Hill Road

Oak Bluffs, MA29 Bayes Hill Road

Price$1,349,000

Est. Mortgage: $/month

MLS ID 37440

  • Residential
  • MlsStatus Active
  • Square Feet 3396
  • Bedrooms 4
  • Bathrooms 3

Extraordinary attention to detail! This spacious and open Contemporary home in the desirable Bayes Hill community is move-in ready, offering a unique blend of multiple gathering spaces and privacy. Continuously renovated, the home is in "cherry" condition---cherry wood floors and railings throughout all three levels; cherry cabinetry in the custom kitchen and all baths; and cherry bookcases in the finished lower level library/den. But the heart of this home is the intelligently designed gourmet kitchen with its quartzite counters, French porcelain tile backsplash, custom cherry cabinets, specialty lighting and quality stainless steel appliances including a commercial grade SubZero refrigerator/freezer, Wolf propane cooktop and double ovens, warming drawer, Bosch dishwasher, built-in microwave and even a built-in coffee maker! The essentials, plus some, are new------all new mechanicals including propane furnace, HVAC, geo/thermal hot water heater, roof, floors, windows, skylights, doors, bathrooms, lighting, ceiling fans etc. Too many details to mention. A must see!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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3 Pond View Drive

Oak Bluffs, MA3 Pond View Drive

Price$1,950,000

Est. Mortgage: $/month

MLS ID 37052

  • Residential
  • MlsStatus Active
  • Square Feet 4350
  • Bedrooms 3
  • Bathrooms 2

3 Pond View has a striking modern 3600 sq.ft home & 750 sq. ft. studio nestled in a private setting abutting a greenbelt of conservation land. The house and studio were designed by Vineyard architect, Bruce MacNelly. It is spacious with high ceilings, white oak floors, an open floor plan which enhances all of its light-filled spaces. The large high windows frame the outdoors, providing visual interest all year long. It is the perfect spot for entertaining and features large walls for exhibiting artwork. The main level offers a large dining room, galley kitchen, living room, large master bedroom, 1.5 baths, laundry & ample closets. Outside the kitchen, there is a bluestone terrace perfect for outdoor dining and entertaining. On the ground floor, there are two walk-out bedrooms, a bath, a large family room & two workrooms that open to a rice stone patio and gardens. The separate spacious studio is ideal for an artist, writer or anyone working remotely. The property has deeded access to 25 feet of beach on Lagoon Pond, a short walk from the residence. Owner's abutting parcel of land is available to purchase by the buyer.

Listed by Kendall & Kendall

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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67 Dukes County Avenue

MLS ID 37112

  • Residential
  • MlsStatus Active
  • Square Feet 974
  • Bedrooms 4
  • Acreage 0.12

IN-TOWN OPPORTUNITY for a home and/or business just waiting for the right investor. Walk to the Harbor, Circuit Ave, the Tabernacle and Beaches. Currently there is a 4 bedroom "home" on the property. Potential to hook up to town sewer based on capacity. Property is sold "As-Is." 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: 2.79% last updated on Jan 14, 2021
* 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.

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7 Old Harbor Lane

Oak Bluffs, MA7 Old Harbor Lane

Price$1,850,000

Est. Mortgage: $/month

MLS ID 37152

  • Residential
  • MlsStatus Active
  • Bedrooms 4
  • Bathrooms 2
  • Half Baths 1

Ocean Views and Neighborhood Beach access! This wonderful summer vacation retreat offers amazing view of Sengy Pond, State Beach, Nantucket Sound, & natural preserve open space. This home boasts inviting, spacious, vaulted ceilings, light and bright bedrooms that each look to the water. Take this house and turn it into your dream home! Bask in the rising sun from one deck and the setting sun from the other deck! This parcel adjoins conservation land offering peace and quiet while just an easy drive to the airport or two ferries. Waterview Farms is centrally located between three towns; Oak Bluffs, Vineyard Haven & Edgartown yet still very private being an exclusive community adjacent to Farm Neck Golf Course. This neighborhood provides beach access with boat storage and docking available. This spacious parcel is great for events & parties, or flying kites & out door games. Explore quaint nearby walking trails to Pecoy Point, or use your paddle board or kayak to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! Two adjoining build-able lots may be available for purchase, please inquire. Inquire about owner financing Please do not attempt to gain access to the house without being approved by listing agent. Additional photos of interior available upon request, houses are being rented. Thanks!

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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.

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