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$5,995,000

Est. Mortgage: $/month

MLS Number 35291

  • Multi-Family
  • Village State Beach
  • Location 41.436238,-70.555927
  • Bedrooms 12
  • Bathroom 6

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 with additional space above, bath and outdoor shower, there is lots of possibilities to to be creative. The garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option. Please view Video of the Property to get a full feel for this one of a kind waterfront property.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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274 Sea View Avenue Oak Bluffs MA

Price$4,450,000

Est. Mortgage: $/month

MLS Number 35074

  • 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: 3.6% last updated on Aug 15, 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$3,900,000

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: 3.6% last updated on Aug 15, 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$3,550,000

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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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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53 Tia Anna Lane Oak Bluffs MA

Price$2,700,000

Est. Mortgage: $/month

MLS Number 34752

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 2442
  • Bedrooms 3
  • Bathroom 3

Never miss a sunset from this custom built waterfront home! Beautifully designed by Breese Architects with a focus on the stunning water views from each room, this three bedroom, three bath home is the perfect property for entertaining family and friends. Set on one acre of land with stairs to the Lagoon for easy water access and a large, grassy lawn area for all your summer games. The custom built home has a lovely open living space with a field stone gas fireplace anchoring the living room, french doors off of the dining area to the deck and an open kitchen with stainless steel appliances, custom cabinetry and granite counter tops. A second floor Master Bedroom Suite is the only room on this level, with water views from the private balcony, a spacious master bath with double vanity, tile floor and heated towel rack and an office/study area off of the bedroom. There are two guest room wings on the first floor along with two full bathrooms, offering your guests plenty of privacy. A den with built-in bookshelves has access to the loft with a private office space. Finishing off this well designed home is the laundry and mud room with access to a casual side door entry~perfect for coming in off the water. Enjoy the beauty of the Island right from your very own home!

Listed by Coldwell Banker Landmarks

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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14 Temahigan Avenue Oak Bluffs MA

Price$2,600,000

Est. Mortgage: $/month

MLS Number 35290

  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 Mill Square Road Oak Bluffs MA

Price$2,175,000

Est. Mortgage: $/month

MLS Number 34973

  • Residential
  • Village East Chop
  • Square Feet 2905
  • Bedrooms 4
  • Bathroom 3

EAST CHOP - WATER VIEWS - GREAT LOCATION! -- Totally renovated, year-round, 4-bedroom, Victorian, overlooks Nantucket Sound. Walk to beaches, harbor, yacht club, tennis courts, ferries and restaurants. Tastefully renovated in 2002 to retain its Victorian charm, its extensive renovations included replacement of all electric, plumbing, heating, many windows, and roof. Features include beach stone fireplace in living room, wrap around front porch, gourmet kitchen appliances, garage and parking for multiple vehicles. Seller agrees to credit buyer at closing, half the cost of design and installation of a new Title V septic system for 5-bedrooms up to $12,500.

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 Paddock Road Oak Bluffs MA

Price$1,999,000

Est. Mortgage: $/month

MLS Number 35025

  • 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 READY!!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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$1,995,000

Est. Mortgage: $/month

MLS Number 35251

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

Perched above Vineyard Haven harbor in the heart of East Chop, this beautiful home exemplifies the best of Martha's Vineyard. Three full floors of living, each with increasingly expansive water views, combine to offer 5 beds and nearly 4000 sf with multiple living rooms and high-end craftsmanship throughout. The 1st floor is ideal for entertaining, with a renovated kitchen offering premium counters, appliances and built-ins. The dining area and light-filled living room center on a gorgeous two-sided fireplace, which sets a stunning tone. There are balconied master suites on both the 2nd and 3rd floors, each including private baths with luxurious tile and fixtures. Forced air heat/AC provide reprieve through the seasons. The grounds are easily enjoyed from ample decking, and beautifully manicured lawn and garden beds adorn the home and detached two car garage. Inside and out, enjoy the sparkle and calm of the Sound, as well as sailboat/ferry activity. And, within a mile of the home are many Oak Bluffs attractions, including the harbor, East Chop lighthouse, campground, and more. Also, Vineyard Haven is under 2 miles away, making this an exceptionally convenient location amongst some of the true “grand dames” of East Chop. Perfect for year-round use with outstanding rental potential, this home is a rare offering below its assessed value - an opportunity not to be missed!

Listed by Compass

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$
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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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24 Paddock Road Oak Bluffs MA

Price$1,995,000

Est. Mortgage: $/month

MLS Number 35641

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 3450
  • Bedrooms 4
  • Bathroom 3

New custom home built by Dubin Construction. House includes upstairs and downstairs master bedrooms as well as upstairs and downstairs living rooms. Second floor includes two additional bedrooms with a shared bath. Custom kitchen and cabinets throughout. Hardwood flooring with tile in side entrance, laundry and bathrooms. Large luxurious bathrooms, large deck off living room and dining room. Stone patio off first floor master. Outdoor shower. Still time to customize landscaping.

Listed by Dubin & Reardon

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 Peter M. Williamson Boulevard Oak Bluffs MA

MLS Number 34857

  • Residential
  • Village Central
  • Square Feet 3100
  • Bedrooms 6
  • Bathroom 5

BRAND NEW!!! Custom design will be Ready for Occupancy this SEASON. Features over 3100 square feet with another 1000 in finished walkout basement including another bedroom. Beautiful marble/tile work in all bathrooms, wide oak hardwood flooring, gas fireplace with marble mantle, first floor en suite master, 8' sliders with access to sweeping deck, 9' ceilings and cathedral in the living room, and an open kitchen/dining area with Wolf stove, Sub Zero fridge, Bosch dishwasher, large center island. Also, attached 2 car garage with unfinished space above. This house flows comfortably through the intimate spaces offering easy living, privacy, and the yard has room for a pool. A must see!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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 Pennacook Avenue Oak Bluffs MA

Price$1,870,000

Est. Mortgage: $/month

MLS Number 33956

  • Multi-Family
  • Village Downtown
  • Bedrooms 8
  • Bathroom 4
  • Half Bath 1

In the coveted Copeland District, steps from beach and town: An unparalleled palace of a property awaits the fortunate investor. Dunmere-by-the-Sea, a soaring, three-story edifice was once an elegant hotel of Oak Bluffs' heyday as a swinging Victorian resort. For the past 40-plus years, this "wedding cake" with panaromic views of Nantucket Sound has served its owners well as a three-unit apartment building with vacation tenants from as near as Boston and as far as Budapest, including many longtime repeaters. Updates over the years have spared many elements of period charm, such as the mansard roof, substantial "gingerbread" trimmings and curvaceous interior stairway. Each unit enjoys bright and spacious floor-through living, with open common areas, full kitchens and baths, two-plus bedrooms and water views. They share use of a laundry, a deep wraparound porch, four parking spaces and generous yard space for lounging and cookouts. The raised finished basement, inclusive of full bath and laundry, has full windows and both indoor and outdoor entries. The opportunities abound: Glamorously upgrade or stay true to the "old school" cottage ambience. Continue the lucrative landlord tradition. Or create condominiums (subject to town permitting). Or go rogue and transform the building into your personal and amazing single-family domain. Property is eligible for tie-in to the town sewer.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 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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