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

Contact us if you have any questions, or if you would like to schedule a showing. Create an account to save favorite listings and to receive email notifications when similar listings become available. 

348 Sea View Avenue, Oak Bluffs, MA

Price$6,490,000

Est. Mortgage: $/month

MLS Number 18014

  • Residential
  • Square Feet 3891
  • Bedrooms 10
  • Bathroom 5
  • Half Baths 1

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - 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. Two wood-burning fireplaces. 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

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

32 Temahigan Avenue, Oak Bluffs, MA

Price$4,995,000

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.

Listed by Point B Realty LLC

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

14 Temahigan Avenue, Oak Bluffs, MA

Price$3,300,000

Est. Mortgage: $/month

MLS Number 32282

  • Residential
  • Square Feet 4821
  • Bedrooms 7
  • Bathroom 3
  • Half Baths 2

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

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

23 East Chop Drive, Oak Bluffs, MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 30153

  • Residential
  • Square Feet 2702
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.54

East Chop - This charming harbor front home has been EXTENSIVELY RENOVATED over the winter. It now features a completely new, modern kitchen that includes an island breakfast bar and opens to the waterside sun porch. New hardwood floors in many of the bedrooms and the bathrooms have also been renovated with new fixtures, tiling and bead board with chair rail - These improvements along with updated electric and plumbing and more make the “Red House” feel like a whole new home. Plus the new outside shower is a welcome addition for beach goers. With five spacious bedrooms and stunning water views from almost every room, this is where summer memories are made. Extra space for overflow can be found over the boathouse/garage and let's not forget the covered veranda - the place where all will convene to admire the views and enjoy the harbor activity. A private deep water dock and 175' of harbor frontage make this the perfect property for the boating enthusiast. Enjoy the luxury of living on the water with the town and beach just a stroll away. (Please see "List of Improvements" under Documents tab for a complete list of improvements).

Listed by Sandpiper Realty

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

15 Dover Street, Oak Bluffs, MA

Price$2,600,000

Est. Mortgage: $/month

MLS Number 32913

  • Residential
  • Square Feet 3800
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.35

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 complement 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.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

55 Ocean Avenue, Oak Bluffs, MA

Price$2,395,000

Est. Mortgage: $/month

MLS Number 32742

  • Residential
  • Square Feet 2997
  • Bedrooms 4
  • Bathroom 5
  • Half Baths 1

Possible OWNER FINANCING AVAILABLE for this BEAUTIFUL, FULLY RENOVATED LUXURIOUS Victorian home with waterviews from almost every room. Enjoy two stories of verandas overlooking Ocean Park and Nantucket Sound. Attention to detail has been paid throughout all three floors of living which feature a gourmet kitchen, all new bathrooms, a parlor/livingroom with waterviews, a walk out lower level with full bath and laundry, four bedrooms and a brick terrace. This in-town property offers off-street parking on Kennebec Avenue, which can accomodate 2-3 cars.

Listed by Vineyard Village Realty

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

335 East Chop Drive, Oak Bluffs, MA

Price$2,390,000

Est. Mortgage: $/month

MLS Number 30026

  • Residential
  • Square Feet 1751
  • Bedrooms 3
  • Bathroom 2
  • Half Baths 1

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.

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

41 & 43 Ocean Avenue, Oak Bluffs, MA

Price$2,300,000

Est. Mortgage: $/month

MLS Number 31605

  • Residential
  • Square Feet 2451
  • Bedrooms 7
  • Bathroom 2
  • Half Baths 1

41 & 43 Ocean Park ~2 BEAUTIFUL PROPERTIES LOCATED ON HISTORIC OCEAN PARK~43 Ocean Ave - 5 BR 1.5 bathrooms~Located on Historic Ocean Park with PANORAMIC WATER VIEWS of VINEYARD SOUND, OCEAN PARK and all the way to CAPE POGUE! 43 Ocean Avenue includes 1987 sq feet ..with 5 bedrooms 1.5 baths This RENOVATED HOME is a block to the Village of Oak Bluffs to explore and enjoy all the wonderful restaurants, galleries, shopping and ferry ports! 41 Ocean Ave is a Year Round Ocean Park Ranch Style home with 464 sq ft 1 bedroom and 1 bath & enclosed sun porch(an additional 184 sq ft.)! WONDERFUL WATER VIEWS OVER HISTORIC OCEAN PARK ALL the WAY TO VINEYARD SOUND! ACTIVE VIEWS OF PARK and located a block to Oak Bluffs Circuit Avenue, ferry ports and beach across the street! STUNNING VIEWS of FAMOUS GAZEBO..Enjoy your wonderful private fenced in grassy yard..onsite parking in garage.. 2 houses 41 & 43 Ocean Avenue ..both houses are being sold together..for $2,300,000

Listed by Ocean Park Realty Inc

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

41 & 43 Ocean Avenue, Oak Bluffs, MA

Price$2,300,000

Est. Mortgage: $/month

MLS Number 30901

  • Residential
  • Square Feet 2451
  • Bedrooms 7
  • Bathroom 2
  • Half Baths 1

Oak Bluffs ~2 homes with 2 separate deeds however sellers are selling both 43 & 41 Ocean Avenue.. 43 Ocean Ave -5 BR 1.5 baths! AMAZING BREATH TAKING COLORFUL SUNRISES from your wrap around porch! One of the 5 bedrooms is on the first floor and first floor laundry! Spacious and SUN FILLED living room and dining area! Beautiful STYLISH & RENOVATED eat in kitchen with lots of cabinets and cottage details throughout! This home is in impeccable condition and truly is a rare offering! 43 Ocean Avenue includes 1987 sq. feet..This RENOVATED HOME is a block to the Village of Oak Bluffs to explore and enjoy all the wonderful restaurants, galleries, shopping and ferry ports! 41 Ocean Ave is a Year Round Ranch Style home with 464 sq ft 1 bedroom and 1 bath & enclosed sun porch(an additional 184sq.ft.)! WONDERFUL WATERVIEWS OVER HISTORIC OCEAN PARK ALL the WAY TO VINEYARD SOUND! ACTIVE VIEWS OF PARK and located a block to Oak Bluffs Circuit Avenue, ferry ports and beach across the street! STUNNING VIEWS of FAMOUS GAZEBO..watch all the boats and Summer Activity from your porch!..Enjoy your wonderful private fenced in grassy yard..onsite parking in garage.. 2 houses 41 & 43 Ocean Avenue ...both houses are being sold together..for $2,300,000

Listed by Ocean Park Realty Inc

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

42 Paddock Road, Oak Bluffs, MA

Price$2,195,000

Est. Mortgage: $/month

MLS Number 32260

  • Residential
  • Square Feet 4200
  • Bedrooms 5
  • Bathroom 4
  • Half Baths 1

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 brand new home has high quality construction and features 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 and outdoor shower. 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 dining area has lovely views of the pond and the family room has 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. Don't miss this opportunity to select your finishes and enjoy this beautiful investment or year round home!

Listed by Ocean Park Realty Inc

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

325 East Chop Drive, Oak Bluffs, MA

Price$2,095,000

Est. Mortgage: $/month

MLS Number 31615

  • Residential
  • Square Feet 1709
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Fall asleep to the sound of a gently breaking surf in this carefully renovated and meticulously maintained turn of the century East Chop beach house. Nestled between the shore of the Vineyard Sound to the west and Crystal Lake to the east, this unique property boasts water views from every window. Enjoy spectacular sunrises from your breakfast table and sunsets over West Chop. Watch maritime activity of all kinds or just listen to the waves from numerous first and second floor oceanside porches. Nearly 150 feet of private beach permits direct access to the water for fishing, swimming, kayaking or paddling. The main living area of this exceptional summer home features a brick fireplace and is lined with large windows and French doors that open to a spacious, enclosed sun porch overlooking the water. The first floor also includes a sun drenched dining room, a home office or first floor bedroom, a half bath and an updated kitchen with high-end appliances, oversized antique porcelain sink and zinc countertops with copper accents. The staircase to the second floor leads to two guest bedrooms with a shared bath, a spacious hallway with built-in closets, laundry and extra storage space. The master bedroom suite features a private bath and sun porch. Other amenities include an enclosed drying yard with a cedar deck, a grilling area off the kitchen, a private outdoor shower on the beach and a one-car garage with a cabana for towels, chairs and beach toys. This wonderful location is also an easy bike ride to the East Chop tennis, beach and yacht clubs and to downtown Oak Bluffs. Frequently featured in island artwork, this spectacular waterfront home provides you with the best of Martha's Vineyard.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

46 Narragansett Avenue, Oak Bluffs, MA

Price$1,950,000

Est. Mortgage: $/month

MLS Number 32203

  • Residential
  • Square Feet 4294
  • Bedrooms 15
  • Bathroom 15
  • Acreage 0.1399

The Narragansett House is a gorgeous Victorian Inn, Built in 1880. Narragansett House has been an Inn for 138 years, and owned and lovingly operated by the same family for the past 31 years. Ideally located a couple of blocks from sandy beaches, fine restaurants, and shopping. This Multi-Use Property is presently run as 80% commercial and 20% residential, and could easily be converted to a private residence. This beautiful Inn is in the highly sought-after Copeland District neighborhood 1.5 blocks from Circuit Ave and 2 blocks from the beach. Situated on one of the largest lots in the area, the Narragansett House with 13 guest rooms all with private baths, some with balconies and ac/heat splits. The inviting and spacious wrap-around porch, and front parlor feature period details and stained-glass windows overlook beautiful perennial gardens. The Private owner's quarters located on the main floor has an open living-kitchen area, 2 bedrooms, 2 bathrooms, an office and private porch with gardens. Being sold fully furnished (less a dozen or so personal items) a fully turn key operation, bed linens and comforters and towels.

Listed by Anchor Realty of Martha's Vineyard

{$agent->Name}

Breakwater MV
30 Main Street
Suite 3
Vineyard Haven MA, 02568
Office: 508-693-6500

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details