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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348 Sea View Avenue, Oak Bluffs, MA

Price$6,490,000

Est. Mortgage: $/month

MLS Number 18014

  • Multi-Family
  • Village State Beach
  • Location 41.436238,-70.555927
  • Bedrooms 10
  • Bathroom 5

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - Perched high on a bluff with 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Wood-burning fireplace. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage and additional space to be creative with, the garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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274 Sea View Avenue, Oak Bluffs, MA

Price$4,995,000

Est. Mortgage: $/month

MLS Number 34138

  • Residential
  • Village State Beach
  • Square Feet 3460
  • Bedrooms 6
  • Bathroom 5

HARTHAVEN WATERFRONT WITH PRIVATE DOCK- An Undeniably special and unique property this Harthaven compound is one of only four homes situated on the picturesque and protected harbor with private dock. Elegant yet casual, vintage yet chic you'll find it all here at this tastefully renovated Oak Bluffs home. The expansive six bedroom property delivers all the amenities one would expect while retaining the charm and character of days gone by. The sprawling first floor boasts commanding water views with access to an expansive covered porch and deck overlooking the protected inlet, barrier beach, and Vineyard Sound - bound to ignite your inner explorer. The private first floor guest wing, complete with deck and beach stone fireplace, combined with the four additional bedrooms and baths on the second level provide the ideal layout for all your family and friends, evident in properties strong rental history. A large boathouse/garage, perched on the water's edge, great for storage of all beach and boating gear, is the perfect complement to this seaside escape. The expansive lawn, beckoning for yard games and laughter, slopes gently to a private dock, offering boaters both protection and easy access to the deeper waters of Nantucket Sound and nearby harbors. The highly sought after location, within the Harthaven community, provides you and your guests with access to tennis and a long stretch of association sandy beach on the calm waters of the sound. A magnificent offering!

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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267 Barnes Road, Oak Bluffs, MA

Price$4,500,000

Est. Mortgage: $/month

MLS Number 34265

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 4046
  • Bedrooms 3
  • Bathroom 5

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: 4.63% last updated on Dec 13, 2018
* 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$4,350,000

Est. Mortgage: $/month

MLS Number 32756

  • Residential
  • Village East Chop
  • Square Feet 6441
  • Bedrooms 6
  • Bathroom 5

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.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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
  • Village East Chop
  • Square Feet 2449
  • Bedrooms 3
  • Bathroom 3

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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$
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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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21 Ice Pond Lane, Oak Bluffs, MA

Price$2,400,000

Est. Mortgage: $/month

MLS Number 34503

  • Residential
  • Village Sengy
  • Square Feet 2950
  • Bedrooms 5
  • Bathroom 4

FARM NECK - This 3.74-acre property is part of the Farm Neck community and is being sold with a full stock membership which confers all the benefits of this Island institution. The 4-bedroom house is set overlooking Fresh Pond and has charming water views. Set a distance away through mature landscape there is a one-bedroom apartment above a 2-car garage. The property is extremely private and abuts 73 acres of conservation land to the east, west and north. To the south - literally at the bottom of the 250-ft backyard - is Fresh Pond. In addition to having access to boating in Fresh Pond, Sengekontacket Pond is a short distance away and Farm Neck stockholders may moor a boat there.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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10 Paddock Road, Oak Bluffs, MA

Price$2,320,000

Est. Mortgage: $/month

MLS Number 33638

  • Residential
  • Village Central
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4

Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day. To be completed in the Fall of 2018. ***** interior pictures shown are of a similar house built by the builder to give you an idea of quality and finishes.

Listed by Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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$2,295,000

Est. Mortgage: $/month

MLS Number 34382

  • Residential
  • Village East Chop
  • Square Feet 3884
  • Bedrooms 5
  • Bathroom 4

Sensational water view contemporary design set 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, has amazing sunsets each evening over the outer harbor! Offering 2 master suites, a total of 5 bedrooms and 4 sparkling tiled bathrooms (renovated 2016), spacious open concept ! Features include multiple private balconies, 3 porches, 2 car garage, granite gas fireplace, gourmet kitchen (renovated 2016), central ac, gleaming hardwood flooring, media room, koi pond, mature plantings, and many quality custom details throughout!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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
  • Village East Chop
  • Square Feet 1496
  • Bedrooms 4
  • Bathroom 2

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: 4.63% last updated on Dec 13, 2018
* 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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90 Dukes County Avenue, Oak Bluffs, MA

Price$2,195,000

Est. Mortgage: $/month

MLS Number 34040

  • Multi-Family
  • Village Downtown
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

ULTRA CHIC + LUXE IN-TOWN MIXED-USE COMPOUND. Located within walking distance to Oak Bluffs town center and harbor, this luxurious designer's own property is a one-of-a-kind opportunity -- offering three residential living spaces, commercial office spaces, plus off-street parking spaces for up to nine (9) cars. Ideal for a savvy investor or business person looking for a smart, live-work situation and the ability to generate additional rental income, this property currently generates $120,000+/year in combined commercial and residential rental income. The compound is anchored by a private and beautifully landscaped courtyard and two levels of indoor and outdoor living spaces including the following: THE TREE HOUSE: (1,668 sq. feet): 3-Bedroom | 3-Bath (includes private second-story deck). THE GARDEN HOUSE: (797 sq. feet): 1-Bedroom | 1-Bath. THE GATE HOUSE: (1,350 sq. feet) 1-Bedroom | 1-Bath. LOWER LEVEL: (additional 1,466 sq. feet - not included in total SF shown) additional work and storage space. There is also a 1-car garage or storage shed on the first floor of the compound. There are superlative architectural and designer touches throughout this amazing property. Exquisite hand-selected furnishings are being offered for separate purchase or negotiation for a turnkey purchase opportunity. There is no other offering like this unique property . . truly a must see!

Listed by Point B Realty LLC

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$
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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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 Pennacook Avenue, Oak Bluffs, MA

Price$1,950,000

Est. Mortgage: $/month

MLS Number 34316

  • Multi-Family
  • Village Downtown
  • Location 41.452340,-70.555809
  • Bedrooms 8
  • Bathroom 4

Own a bit of history in the Copeland district! The Dunmere by the Sea has one hundred fifty years of hospitality behind it's name and under its roof. Built as a small hotel, it was converted to apartments by an architect in 1970. It has been family owned and operated for over 40 years. It is ideally situated, 150' from the famous Inkwell beach and minutes from shops and restaurants of "downtown" Oak Bluffs and the ferries. The town playground and tennis courts are two whole blocks away. Off road parking. Water views from every floor. Enjoy the ocean breeze and sunrise over Inkwell beach as you relax on the deep wrap around porch. Sewer hook up in place and approved.

Listed by Anchor Realty of Martha's Vineyard

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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283 East Chop Drive, Oak Bluffs, MA

Price$1,699,000

Est. Mortgage: $/month

MLS Number 33651

  • Residential
  • Village East Chop
  • Square Feet 2456
  • Bedrooms 4
  • Bathroom 2

Private beach on East Chop with gorgeous water views of the Vineyard Sound from each room, including all bedrooms! Quintessential Vineyard shingled house right on the water; swim, kayak or watch the ferry and boats from your private deck or porch just a few steps to the Sound. 2456 square foot house with four bedrooms (two of them enormous), two and one half baths, large separate laundry room, open floor plan to include fully equipped kitchen, dining room and living room with a large stone fireplace, all with stunning water views. Second floor family room and ample closet space in every bedroom. Enjoy countless hours relaxing on the side deck with outdoor living space in addition to the new stone patio for all your grilling needs. Convenient to both Oak Bluffs, Vineyard Haven and to the Telegraph Hill Lighthouse. Perfectly situated within one mile of East Chop Beach Club, Yacht Club and Tennis Club. Great rental history too. This home will not disappoint.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* 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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