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

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267 Barnes Road Oak Bluffs MA

Price$4,500,000

Est. Mortgage: $/month

MLS Number 34265

  • Residential
  • Square Feet 4046
  • Bedrooms 3
  • Bathroom 5
  • Half Baths 1

Well appointed 4000+ sq ft Contemporary home surrounded by a little more than one acre of lush landscaped greenery on Lagoon Pond with private beach and potential for a dock. Spacious 3 bedroom 5.5 bathroom with high ceilings, two first floor offices, open living/ dining areas all with views of the Lagoon. The large gourmet kitchen. Sweeping waterviews from every room. A wrap around deck and a screened sun room adjoins the upstairs bedrooms. Full basement ready to be finished. This house has spacious rooms perfect for entertaining . Being sold mostly furnished.

Listed by Martha's Vineyard Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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225 East Chop Drive Oak Bluffs MA

Price$3,950,000

Est. Mortgage: $/month

MLS Number 33942

  • Residential
  • Square Feet 2449
  • Bedrooms 3
  • Bathroom 3
  • Half Baths 1

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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32 Temahigan Avenue Oak Bluffs MA

Price$3,500,000

Est. Mortgage: $/month

MLS Number 32756

  • Residential
  • Square Feet 6441
  • Bedrooms 6
  • Bathroom 5
  • Half Baths 2

HISTORIC EAST CHOP WATERFRONT ESTATE WITH BOATHOUSE AND DEEP WATER DOCK. Originally built in 1870 with all of the grandeur of a 19th century seaside estate, this grand historic home features over 6,000 square feet of finished interior living space which was meticulously renovated from top to bottom in the year 2000, under the direction of noted architect, Joseph Dick and island builder, Everett Whorton. Today, this luxurious home maintains all of the original character and architectural details of the era, including beautiful coffered ceilings, gorgeous custom wood paneling, and finely crafted millwork throughout. The property boasts sweeping views from three floors of living space -- plus a spacious outdoor deck -- across the 3.2-acre property with rolling lawn, patio with stone fireplace and beautifully landscaped grounds to Vineyard Haven Harbor and Vineyard Sound beyond. A wooden boardwalk crosses over a small pond, leading to the water's edge where a 750-sf boathouse with stone fireplace, kitchen and bath sits adjacent to a deep water dock and moorings. The property also includes a detached 2-car garage with unfinished living space above which can be easily transformed into a beautiful Guest House, also with water views. This iconic property is the ultimate place to gather family and friends and create treasured Vineyard memories for years to come. Furnishings are available separately. Note: Sale subject to bank approval.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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311 East Chop Drive Oak Bluffs MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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15 Dover Street Oak Bluffs MA

Price$2,195,000

Est. Mortgage: $/month

MLS Number 34382

  • Residential
  • Square Feet 3884
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.37

This Custom built home, with SENSATIONAL WATER VIEWS CONTEMPORARY DESIGN SITS HIGH ON A LANDSCAPED HILLTOP with penetrating views of Vineyard Haven Outer Harbor and Vineyard Sound to the coast of Cape Cod. This exciting residence, in PRISTINE CONDITION, includes most of the designer top of the line furnishings, has amazing SUNSETS over the Outer Harbor! Offering 2 master suites, a total of 5 bedrooms and 4 sparkling marbled bathrooms (renovated 2016), SPACIOUS OPEN CONCEPT! Features include multiple private balconies, 3 porches, 2 car garage, and parking for 8 vehicles, Granite fireplace, GOURMET KITCHEN (renovated 2016), CENTRAL AC, GLEAMING HARDWOOD FLOORING, media room, outside pond, mature plantings, and MANY QUALITY CUSTOM DETAILS THROUGHOUT! Comes with entertainment systems and TV's mounted on walls, and a security system installed. A special property, in a unique and historical location, that offers privacy and accessibility, as you watch the ferries come and go!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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7 Quail Run Oak Bluffs MA

Price$1,325,000

Est. Mortgage: $/month

MLS Number 34677

  • Residential
  • Square Feet 2877
  • Bedrooms 3
  • Bathroom 3
  • Half Baths 1

IMMACULATE Residence impeccably maintained is in the desirable Sengekontacket Community of Oak Bluffs! This Exquisite custom design, comfortably on one level, is situated on almost an acre of land with mature landscaping, stone walls and colorful perennial flower beds. Enter an impressive foyer into an OPEN BRIGHT living room highlighted with a beautiful stone European wood burning fireplace and 12 ft ceilings. CENTRAL AC ! The interior design is complemented by attractive furnishings that add to the graceful flow of the floor plan. Gracious Master Suite and 2 additional bedrooms are all spacious and inviting with custom closets, the kitchen is large with high end appliances, and there is a cozy separate den, and a dining room with sunsets. SURPRISE! There is a lower level, fully finished, offering a large media/rec room and multiple gathering spaces along with a full tiled bathroom & spacious workshop with walk out access! TERRIFIC LOCATION with private amenities that include access to both fresh and salt water ponds, community dock, mooring available, with kayak storage and boat ramp, a community clubhouse on the fresh pond (available for private events), tennis courts, and community services such as curbside trash pick-up and snow removal. MUST SEE HOME!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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61 Bayes Hill Road Oak Bluffs MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 22464

  • Residential
  • Square Feet 2745
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1

A must see in Bayes Hill! This spacious two story home on an acre of land with a fantastic backyard is the perfect place to call home. Traditional in style with formal and casual spaces that flow nicely to the multiple gathering areas. The dining room, kitchen and family room span the back of the house and all feature glass doors to the pool area. The outside spaces are amazing - heated gunite pool with pebble tec finish with patio surround and cabana for lounging in the shade. A screened porch offers more outside yet sheltered space, and the expansive decking unifies it all. Four great sized bedrooms occupy the second level including a grand master with walk-in closet and luxuriously appointed bath. A first-floor office/den can also serve as a fifth bedroom. The lower level is nicely finished and offers an additional 700+ square feet of space - perfect for movie watching and gaming. This home has it all - laundry room/mud room, two car garage, attic for storage and more. Bayes Hill is an attractive neighborhood with substantial homes and large parcels providing good privacy; and enjoy association tennis!

Listed by Sandpiper Realty

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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27 Bayes Hill Road Oak Bluffs MA

Price$1,189,000

Est. Mortgage: $/month

MLS Number 34713

  • Residential
  • Square Feet 3000
  • Bedrooms 4
  • Bathroom 4
  • Half Baths 2

A builder's own custom colonial home nestled in a private setting of the Bayes Hill Association in Oak Bluffs. It is a desirable community of substantial homes with private tennis and easy access to the Lagoon & Sailing Camp. This home is situated on a .75 acre lot with an abundance of mature landscaping offering privacy. The home offers a tremendous amount of living space . It has a spacious open kitchen with bar, 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 woodburning fireplace and a formal dining room 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”. The suite is complemented with a beautiful atrium window, wet bar and bathroom. Designed for year around living, with gas FHA heating zones and central A/C,ample storage ,huge garage and laundry room with sink. In addition,the attic has been converted into a spacious and bright office space with large skylights and built in shelving. The basement is fully finished with a second washer / dryer & bath. Well sited on the lot with a back deck, patio, big yard and garden.Surrounded by an abundance of mature trees and rows of hydrangeas. 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

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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71 Pennacook Avenue Oak Bluffs MA

Price$1,149,000

Est. Mortgage: $/month

MLS Number 34791

  • Residential
  • Square Feet 2108
  • Bedrooms 6
  • Bathroom 2
  • Half Baths 1

CLASSIC BEAUTY IN THE HEART OF OAK BLUFFS, The Pennacook House is set on a slight hill on a large landscaped yard. YEAR ROUND 6 bedroom, 2.5 bath home has a lovely eat-in kitchen, formal dining and living rooms with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period details and many updates throughout. Brand new state of the art propane hot water heating system and new electrical panel. Full walk-out basement with laundry and plenty of storage space. Home is sunny and warm in the winter and catches the cool breezes in the summer. GREAT LOCATION just a few blocks to town center, ferry, Ocean Park, and beaches. VERY STRONG RENTAL HISTORY!

Listed by Ocean Park Realty Inc

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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31 Tuckernuck Avenue Oak Bluffs MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 34488

  • Residential
  • Square Feet 1738
  • Bedrooms 4
  • Bathroom 1
  • Half Baths 1

A rare opportunity to own a property bordering Waban Park looking out to the ocean beyond. This spacious house with over 1700 square feet of interior space is tied into town sewer. Sit back and relax on the wrap around porch as you gaze over one of the most famous of Oak Bluffs parks an open grassy field and the ocean beyond. The sandy beach is just a block away. The house has been updated with a large kitchen, dining room with built in cabinets, a sun porch and spacious living room that runs the width of the house. Lovingly maintained wood floors and freshly painted walls throughout. Presently there are 4 bedrooms with with an additional second floor sitting room that could be another bathroom or another bedroom. The two front bedrooms have doors that open onto the 2nd floor large porch. Just a short distance to all the shops restaurants and entertainment of downtown Oak Bluffs.

Listed by Anchor Realty of Martha's Vineyard

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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52 Pennacook Avenue Oak Bluffs MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 34697

  • Residential
  • Square Feet 1926
  • Bedrooms 7
  • Bathroom 2
  • Half Baths 1

Downtown Oak Bluffs - Located in the heart of Oak Bluffs and in close proximity to beach, town and ferries is this sprawling Victorian-style home that was thoughtfully renovated in 2012. With 7 bedrooms, there is plenty of space for your family and friends. Enjoy your morning coffee or afternoon cocktail in a rocking chair on the covered porch overlooking a small town park. Walk through the arched doorway into a living area with 2 walls of windows. There is a spacious dining room with a bay window that welcomes in the afternoon light. Continue on into the eat-in kitchen,with large butler's pantry. The kitchen was recently updated with new appliances, cabinets and counter tops. Two bedrooms and a full bath complete the first floor. Upstairs features vaulted ceilings with painted wood paneling throughout the 5 bedrooms. There is a full bath and powder room that round out the second floor. The home features wood floors throughout. Tucked away on the side of the house is a welcoming outdoor living area with a patio. The requisite outdoor shower completes this well-appointed downtown home. Kitchen was renovated in 2017 and the rest of the home was renovated in 2012. Being sold furnished and with summer rentals already in place.

Listed by Island Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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42 Narragansett Avenue Oak Bluffs MA

MLS Number 34772

  • Multi-Family
  • Village Downtown
  • Bedrooms 6
  • Bathroom 3
  • Half Baths 1

EXCEPTIONAL OPPORTUNITY IN TOWN OAK BLUFFS WALK to BEACHES, GALLERIES, RESTAURANTS & FERRY PORTS ! This VICTORIAN MULTI FAMILY offers a total of 3 renovated apartments with newer kitchens, tiled bathrooms and wood floors! Apartment #1 in the front on the first floor offers high ceilings with open and bright living spaces with 2 ample size bedrooms and full tiled bathroom & half bath. Apartment #2 in the back of the building offers one 1 bedroom, an open living and updated kitchen with a tiled bathroom. Apartment #3 on the second floor offers an ABUNDANCE of SPACE, SUNSHINE, 3 BEDROOMS, UPDATED KITCHEN and TILED BATHROOM & BALCONY! Other features include NEWER WINDOWS, PARKING for 3 cars, outside shower, side yard and brick patio! INVESTMENT OPPORTUNITY!! TREMENDOUS RENTAL $$$$INCOME!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 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.

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