Oak Bluffs Real Estate

Oak Bluffs is a classic beach resort town on the northeast shore of Martha's Vineyard. Real estate in Oak Bluffs includes condos, single family homes, homes with dock access, acreage, and more. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

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274 Sea View Avenue, Oak Bluffs, MA

Price$4,995,000

Est. Mortgage: $/month

MLS Number 34138

  • Residential
  • Square Feet 3460
  • Bedrooms 6
  • Bathroom 5
  • Half Bath 1

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: 4.45% last updated on Jan 17, 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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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 Bath 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: 4.45% last updated on Jan 17, 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$4,350,000

Est. Mortgage: $/month

MLS Number 32756

  • Residential
  • Square Feet 6441
  • Bedrooms 6
  • Bathroom 5
  • Half Bath 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.

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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 Bath 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: 4.45% last updated on Jan 17, 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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21 Ice Pond Lane, Oak Bluffs, MA

Price$2,400,000

Est. Mortgage: $/month

MLS Number 34503

  • Residential
  • Square Feet 2950
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

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: 4.45% last updated on Jan 17, 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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10 Paddock Road, Oak Bluffs, MA

Price$2,320,000

Est. Mortgage: $/month

MLS Number 33638

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

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. ******* 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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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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$2,295,000

Est. Mortgage: $/month

MLS Number 34382

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

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: 4.45% last updated on Jan 17, 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 Bath 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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28 Beach Road, Oak Bluffs, MA

Price$1,595,000

Est. Mortgage: $/month

MLS Number 32752

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2

VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound and beyond to Woods Holes as well as a straight shot down the Lagoon, but this home was also created to be a comfortable home for year-round and summer living. Newly built 4 bedroom/2.5 bath home has commanding views from almost EVERY room with 2-levels of covered decks on the Vineyard Sound side of the home and 2-levels of decks on the Lagoon side. First level features 3 bedrooms, spacious family room, a full bath with laundry and ample storage. The second level features a sun-drenched open floor plan with a gourmet kitchen with stainless Thermador appliances, Silestone counters and an abundance of cabinets. Take in the long view down the Lagoon from the living area with gas fireplace and custom mantel. The master en suite has high ceilings with bathroom features that include a double-sink vanity with marble counters and glass shower enclosure finish this level of the home. There are sliding doors on both levels that open to the front and side decks. High-efficiency heat pump system, central air, HOT TUB and more. Home is ready for you to pack your bags and move in. Did we mention the views? Come tour this unique home and see them for yourself. Rentals in place for the Summer of 2019. Purchase the home and get the rental income at the closing! Home is solar-ready.

Listed by Island Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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
  • Village Lagoon/Harbor
  • Square Feet 2745
  • Bedrooms 5
  • Bathroom 3

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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
  • Village Downtown
  • Square Feet 1738
  • Bedrooms 4
  • Bathroom 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 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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