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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348 Sea View Avenue, Oak Bluffs, MA

Price$6,490,000

Est. Mortgage: $/month

MLS Number 18014

  • Multi-Family
  • Village State Beach
  • Bedrooms 10
  • Bathroom 5
  • Half Bath 1

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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Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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$4,750,000

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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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14 Temahigan Avenue, Oak Bluffs, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 32282

  • Residential
  • Village East Chop
  • Square Feet 4821
  • Bedrooms 7
  • Bathroom 3

Historic Water View Home with views of endless sunsets and sailboat races! On the market for the first time in over 50 years. Originally built in 1915, this stately Dutch Colonial has been enjoyed as a family gathering and celebration place every summer. Everything about this house....the 7 bedrooms, grand foyer, imposing dining and living rooms (both with water view), the original hand crafted woodwork details and the full length wrap around covered veranda overlooking West Chop and Vineyard Sound....will help you create your own family legacy and memories on the island. You will be amazed by the classic architecture of the home and the sweeping back yard inviting games for the young and old alike. A deeded walkway to the beach is included where you can keep a dingy to row out to your moored boat, sit and watch the sun set over West Chop or take a quick dip in the Sound. Remember...this is a home where porch parties are a must!

Listed by RE/MAX on Island

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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 Old Harbor Lane, Oak Bluffs, MA

Price$2,925,000

Est. Mortgage: $/month

MLS Number 33797

  • Residential
  • Village Sengy
  • Square Feet 2488
  • Bedrooms 4
  • Bathroom 4

Waterview Farms Opportunity: One of the most spectacular vistas of Sengekontacket Pond and Nantucket Sound. Beautifully landscaped with specimen plantings, perennial hydrangea, seasonal flowers, and semi bordered by stone walls. Open floor plan, large living room, kitchen with granite counter tops, and stainless appliances. Living room opens to a large deck with hot tub. Contemporary ranch with four bedrooms and four full baths. Three of which are suites. Adjacent to "Farm Neck” is the 3rd green… Short stroll through the meadow leads to the beach access for water sports. ( 24 hr notice required for showings)

Listed by Island Home Realty Inc.

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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335 East Chop Drive, Oak Bluffs, MA

Price$2,390,000

Est. Mortgage: $/month

MLS Number 30026

  • Residential
  • Village East Chop
  • Square Feet 1751
  • Bedrooms 3
  • Bathroom 2

After almost 2 years of permits ,board meetings and approvals a complete renovation has been completed on this home! This has all been accomplished with finishings in excess of one thousand dollars a foot. Let me describe some of the features! Starting in the kitchen there is a Wolf 6 Burner Cook top with 2 Wolf Ovens underneath and one Wolf Microwave; a Sub Zero Cooling center with Glass Doors and drawers with Separate under counter Freezer with cooling drawers. Miele Coffee center, trash compactor and Sub Zero Red wine with separate white wine fridge with 2 cooling drawers for soda and beer; and Sub Zero ice maker. Custom Brazilian Granite counters with walnut floors. Central vacuum, Radiant heat in all floors through out the whole home! No cold toes! In addition to the radiant heat there is a Hi Velocity heat and A/C system. The original 1900 stone fireplace is redone and in place with a modern gas option. Control 4 security, lighting, video and alarm. Surround sound inside every room and outside whole home for the ultimate music experience. Let's talk about the "Bones" The home was raised to meet the one hundred year flood plan. Each stud in the home was removed, replaced screwed and glued in place to make a home as strong as a boat! Besides that, state of the art insulation and the most modern sound proofing was installed along the road to completely diminish any sounds. Every detail was scrutinized and completed with the best of the best. The master bedroom has a look and feel of being "in the water" and the master bath is complete with a Steam Bath with 10 shower heads , and a Ultra Bayne tub. The second floor deck has a top of the line hot tub overlooking the ocean. Because of the layout of the home, changing rooms, outdoor bathroom, and garage, a private beach compound has been created whereby the occupants can sit,lounge, and swim in complete serenity. It is a "turn key", "state of the art" home that measures up to today's standard of "the ultimate Vineyard experience!"

Listed by Jane Brown Assoc.

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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 32913

  • Residential
  • Village East Chop
  • Square Feet 3800
  • Bedrooms 5
  • Bathroom 4

Water views, lots of square footage, prime location, and a big bedroom count - you get all this and more in this stunning home. Even in a neighborhood of such substantial properties, 15 Dover Street has the ability to turn heads. This grand dame of East Chop surveys the harbor and all else from her elevated position. The residence is perfectly at ease in this area of classic antique homes, but was actually constructed in 1998 by a respected Island builder who took his inspiration from the distinguished shingled homes that are found in the more desirable enclaves of Martha's Vineyard. As soon as you step inside it becomes apparent that this is a very modern home with wide-open living spaces, multiple entertaining areas, two master bedroom suites, a renovated gourmet kitchen and bathrooms, hardwood floors, and a double-sided fireplace. The huge picture windows accentuate the water views and make it feel like you could reach out and touch the ferries passing by. Other important amenities include central AC, a modern 2-car garage, and a full basement. All the bedrooms are generously proportioned, and three of them have private decks. The landscaping and gardens are the perfect complements to the property. As you would expect, such a home is in extremely high demand by summer visitors, and so it generates a very handsome rental income. The home is easy to show during the off-season and comes completely furnished. Abundant waterviews - watch our video https://vimeo.com/245739832

Listed by Wallace & Co. Sotheby's

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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42 Paddock Road, Oak Bluffs, MA

Price$2,195,000

Est. Mortgage: $/month

MLS Number 33543

  • Residential
  • Village Sengy
  • Square Feet 4200
  • Bedrooms 5
  • Bathroom 4

OAK BLUFFS - new, luxury enclave - The Preserve at the Woodlands! Enjoy the best of both worlds in this lovely area abutting 200 acres of conservation land yet centrally located off County Road near Farm Neck Golf Club with bike paths that provide EASY ACCESS into downtown Oak Bluffs, Edgartown and Vineyard Haven. Relax and enjoy POND VIEWS and panoramic meadow views. This HIGH QUALITY NEW CONSTRUCTION offers 5 bedrooms and 4.5 bathrooms with 9 foot high ceilings. The wooded 1.8 acre lot offers a spacious backyard with a bluestone patio for entertaining, outdoor shower and borders conservation land for complete privacy. The option to add a POOL is available upon request. An OPEN FLOOR PLAN features a large gourmet kitchen with a Sub-Zero fridge, Wolf range and other professional stainless steel appliances. The living and dining area has lovely views of the pond, custom built-ins and a gas fireplace. A first floor master bedroom contains an en suite bath, dressing area and walk-in closet. For your convenience, there is a first floor laundry room, mud room and powder room. Upstairs there are four SPACIOUS bedrooms - two of which are master bedrooms with en suite baths and vaulted ceilings. The two additional bedrooms share a hallway bathroom with double sinks. Two of the bedrooms offer pond views. There is an additional washer and dryer upstairs. Enjoy UP-ISLAND PRIVACY with DOWN-ISLAND CONVENIENCE! Don't miss this opportunity to enjoy this beautiful INVESTMENT property and begin to earn income right away. Or enjoy it all year round yourself with family and friends!! MOVE IN BY AUGUST!!

Listed by Ocean Park Realty Inc

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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71 Ocean Avenue, Oak Bluffs, MA

Price$1,900,000

Est. Mortgage: $/month

MLS Number 32448

  • Residential
  • Village Downtown
  • Square Feet 2334
  • Bedrooms 7
  • Bathroom 4

Ocean Park Gem. Located on historic Ocean Park in the heart of Oak Bluffs near shops, restaurants, and beaches this Ocean-View property has a total of 7 bedrooms 4.5 bathrooms - It's 2 houses in 1. A multi-family property that offers a 5 bedroom, 3 bathroom home on Ocean Ave. with water view AND a 2 bedroom 1.5 bathroom home on Samoset Avenue. A common wall and adjoining deck bring these two great spaces together. These houses are updated and ready for new investors. This property has a great rental history and is an amazing income producer.

Listed by Anchor Realty of Martha's Vineyard

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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112 Park Street, Oak Bluffs, MA

Price$1,785,000

Est. Mortgage: $/month

MLS Number 30743

  • Residential
  • Village East Chop
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 3

WATER VIEWS and SPECTACULAR SUNSETS are yours from this gorgeous, FULLY FURNISHED, East Chop home nestled on a large double lot in this highly desirable neighborhood. This dazzling home offers classic charm with modern, luxury amenities. The 75 ft. wrap around deck and covered dining rotunda were built for enjoying true Vineyard living. This home has 4 bedrooms and 3 full bathrooms with marble, custom tile and original hard wood floors. Incredible customized high end kitchen and cozy sunroom have double french doors that opens onto a pergola covered deck creating a flowing indoor/outdoor living experience. Make this your year round home or keep as an investment property with over $70,000 a year of rental income in place. Your Island Dream Home Awaits.

Listed by Laer Realty Partners

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 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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