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

Questions about buying a home in Oak Bluffs? Call Coldwell Banker Landmarks Real Estate: 508-693-6866

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21 Paddock Road

Oak Bluffs, MA21 Paddock Road

Price$2,397,000

Est. Mortgage: $/month

MLS ID 36690

  • Residential
  • Square Feet 4353
  • Bedrooms 6
  • Bathrooms 5
  • Half Bath 1

THE PRESERVE AT THE WOODLANDS - PRE-CONSTRUCTION OPPORTUNITY. Welcome to Oak Bluff's newest luxury enclave ,nestled in a beautiful woodland setting with bucolic meadow views and a lovely pond. This gorgeous property connects with miles of walking/hiking trails and a bike path to Farm Neck Golf Club and all three down island towns and beaches. Carefully crafted association covenants have been developed to preserve the character, integrity and value of this distinctive property. Your new construction dream home awaits with designs by noted island architect, Chuck Sullivan.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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 Sengekontacket Road

Oak Bluffs, MA3 Sengekontacket Road

Price$1,999,000

Est. Mortgage: $/month

MLS ID 36665

  • Residential
  • Square Feet 3400
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 1

SENGEKONTACKET A WATERFRONT COMMUNITY: Situated on almost 2 acres of land, gently south sloping, abutting conservation land, this sun-filled Vineyard design has all of the features for a gracious year round or vacation lifestyle. The very special Sengekontacket community offers 2 tennis courts, a clubhouse on a spring fed freshwater pond, and a private salt water dock with easy access to Vineyard Sound. The house design has a cheerfully engaging great room with lots of windows, granite and quartz counters, a black granite gas fireplace highlights the built-in cabinetry, beautiful wide oak flooring, and access to a stone patio, and a sweeping back yard meadow. Also, on the first floor, is a convenient mud room with separate laundry room, a half bathroom and at the other end is en suite master with private deck. The second floor, with brilliant Caribbean Pine flooring, has 4 more spacious bedrooms serviced by 3 more tiled bathrooms. Accessed from the mudroom is a stairway to a 6th unfinished bedroom/full bath over the garage. With high end appliances, irrigation, central AC, and exquisite custom detail, this is a property of exceptional value. PERFECT SETTING FOR A BACKYARD POOL! EXCELLENT RENTAL HISTORY!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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48 Prospect Avenue

Oak Bluffs, MA48 Prospect Avenue

Price$849,000

Est. Mortgage: $/month

MLS ID 36411

  • Residential
  • Square Feet 2016
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

This "Home Sweet Home" tucked away on a residential street is conveniently located, less than a mile from Oak Bluffs center and easy access to all necessities. Sitting on a .28-acre lot, this home features spacious rooms, high ceilings, plus a bonus walk-out basement with 3 finished rooms, and a full bathroom. The first floor has custom oak flooring, with an inlaid design in the living area accenting the stone fireplace. The kitchen and dining area has ample space for gathering with easy access to the deck. The second-floor features wall to wall carpet, a large inviting master bedroom suite with private bathroom and walk-in closet. Two other spacious bedrooms share a full hall bathroom off the hallway. The sunny back deck, with custom built-in bench seating, and a shed completes the backyard. The house flows nicely through large sun filled rooms -a must see in this area.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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102 Pond View Drive

Oak Bluffs, MA102 Pond View Drive

Price$790,000

Est. Mortgage: $/month

MLS ID 36605

  • Residential
  • Square Feet 1310
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.589

LOCATION,LOCATION,LOCATION! BUYERS looking to be in Oak Bluffs close enough to town, yet far enough out of town to realize the country feel of what Oak Bluffs really has to offer. Shopping, schools, ferries, and harbor just a 2 minute drive and a very short walk to Lagoon Pond. What more can you ask for? Deeded rights to Lagoon Pond....directly across the street (Barnes Road) from this 4 bedroom two bath home located in the lovely Vineyard Hills Community. This established subdivision offers larger lots along with open space/common areas and has become a very popular go to location of Oak Bluffs. The 1310 square ft home is settled into a hill in the rear of the property thus creating a great opportunity to utilize the walk out basement. In the front yard there may be room enough for a potential guest house/garage with the proper permits and approvals from the town boards. Entering the home into the spacious unfinished mudroom gives you the chance to personalize your entry with your own ideas. The owner has done some renovations about 8 years ago adding new stainless steel appliances, new bathrooms, and A/C,. This is a must see. Yes, there are areas that could use sprucing up but just think 4 Bedrooms, 2 full baths and full walk out basement with oil forced hot air. Outside shower already in place. All this on just over a half acre of land. Tenants in place 24 hr NOTICE.

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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42 Waterview Road

Oak Bluffs, MA42 Waterview Road

Price$975,000

Est. Mortgage: $/month

MLS ID 36572

  • Residential
  • Square Feet 1132
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.32

Waterview Farm - centrally located and near the Farm Neck Golf Course this private waterfront community features an association beach and dock on Sengekontacket Pond with access to Nantucket Sound and acres of common land offering views of the sound and pond. Bordering one of the meadows this well cared for contemporary catches the morning light filling the living, dining and kitchen area with sunshine. The spacious deck is embraced by the two wings of the house with multiple sliding doors granting access. The three bedrooms and two baths are separated from the main living area creating privacy and calm in the middle of everyday activities. A loft provides an additional sleeping area or study. Perfect for 3-season living with a woodstove to take the chill away in early spring and fall with backup electric heat, as well as air conditioning/heating splits for your summer comfort and insulated floors. A garden shed at the entrance of the driveway and a privacy fence along the road creates a pleasing entrance to the property. A welcoming deck, outdoor shower and a platform deck sited in the meadow offering distant water views of Sengekontacket Pond and Nantucket Sound complete this charming property. Well loved by the same family for many years and enjoyed by a regular cadre of repeat summer tenants, this home provides a memorable Vineyard experience. Offered furnished. List of exclusions available under documents.

Listed by Coldwell Banker Landmarks

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1 Hebron Avenue

Oak Bluffs, MA1 Hebron Avenue

Price$435,000

Est. Mortgage: $/month

MLS ID 36585

  • Residential
  • Square Feet 687
  • Bedrooms 2
  • Bathrooms 1

Sea Side Cottage with views of Oak Bluffs harbor! Walk to beaches, ferries, harbor and Oak Bluffs town activities. Original charm paired perfectly with comfortable amenities. Terrific location with views from both the covered porch and 2nd floor balcony. This tastefully remodeled 2 bedroom corner cottage is light filled and airy! With a newer roof, off street stone patio, outdoor shower and propane heater, it's ideal for shoulder season enjoyment as well as summertime fun! The Martha's Vineyard Camp Meeting Association is a treasured setting with over 300 antique gingerbread cottages, historic Tabernacle and beautiful park grounds. Community benefits and municipalities are many - This sweet vintage abode awaits you!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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1 Bird Street

Oak Bluffs, MA1 Bird Street

Price$1,095,000

Est. Mortgage: $/month

MLS ID 36463

  • Residential
  • Square Feet 2330
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.22

INVITING WITH COASTAL FLAIR! Tucked away yet walking distance to Oak Bluffs village amenities, harbor and beaches! The stonework, gardens and tidy brick path lead to the door of this charming expanded cape. Beautifully designed and maintained, this sturdy lightly used four bedroom home is open and spacious. Facing South the sunshine streams in and the many stylish details shine bright. Generous great room, exceptional kitchen design with quartz countertops and custom cabinetry. Two Bedrooms on the first floor take advantage of easy access with glass doors to the private yard and mini oasis of easy care plantings! Newly completed second floor has two enormous bedrooms, each ensuite with tons of closet space. All this plus a fabulous cedar outdoor shower and an attached garage - come see how sweet Island life can be!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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 Tia Anna Lane

Oak Bluffs, MA17 Tia Anna Lane

Price$1,025,000

Est. Mortgage: $/month

MLS ID 36290

  • Residential
  • Square Feet 2056
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

This is turnkey, ready to be yours fully furnished. Three bedrooms, and 2.5 baths (one of which is the Master suite). First floor Open living, kitchen, dining, half bath/laundry room, and Master suite. Deluxe Master Bath has dual vanities, large tiled walk-in shower, and a walk in closet. Kitchen is fully equipped, with an island/breakfast bar. French doors lead to a blue stone patio. Two bedrooms on the second floor share a full bath, open office/den with a large storage closet. Sits on a half acre with mature landscaping grounds, colorful plantings, a large back yard and a gardener's shed. Centrally located to all three towns, bike path, and just step away from the Lagoon Pond. Agent is related to the Seller.

Listed by Island Home Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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

7 Blueberry Path

Oak Bluffs, MA7 Blueberry Path

Price$1,800,000

Est. Mortgage: $/month

MLS ID 36036

  • Residential
  • Square Feet 3770
  • Bedrooms 4
  • Bathrooms 4
  • Half Bath 1

The Tower House - Sengekontacket, Oak Bluffs Water views of Sengekontacket Pond and the Nantucket Sound from almost every room in the unique hilltop contemporary. This large-bright 4+ bedroom/4.5 bath house has almost 4,000 sq/ft of living space with 2 master suites, multiple living areas and six private decks including a rooftop deck that provides 360-degree views of the Island. The original section of the house has been completely renovated and has a master suite with private balcony, two other bedrooms with a shared bath and a large open modern kitchen with Bosch appliances and Quartz countertops and large deck with lovely Vineyard views. The new section has two living areas and dining area, a master suite that spans the entire floor that includes a huge master bedroom with private office, walk-in closet and bathroom. The third floor provides another living or sleeping area with half bath and a private deck. A custom stainless-steel staircase brings you to a rooftop deck that provides a 360-degree view of the Island. Enjoy the great amenities that the Sengekontacket Association which offer walking trails, tennis/pickleball courts, a member clubhouse with large mahogany deck, private beach and kayak/canoe launch.

Listed by The Vineyard Life Brokered by eXp Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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74 Columbian Avenue

Oak Bluffs, MA74 Columbian Avenue

Price$699,000

Est. Mortgage: $/month

MLS ID 36475

  • Residential
  • Square Feet 1579
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.25

Classic Cape situated in desirable location close to Lagoon Pond. Open kitchen/dining area and living room with fireplace. This 3 bedroom 2 bath home is move in ready. Full basement for utility and storage needs.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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