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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21 Tower Ridge Road Oak Bluffs MA

Oak Bluffs, MA21 Tower Ridge Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 35358

  • Residential
  • Square Feet 3957
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.78

Incredible investment opportunity in the highly desirable Tower Ridge neighborhood. This lovingly maintained home has undergone many sensible upgrades and is ready for a new owner's stress-free enjoyment. The property is situated on a quiet and private street, and is located close to Farm Neck Golf Club, bike path and miles of hiking trails. New windows, renovated gourmet kitchen, copper gutters, red cedar siding, 2-sided granite fireplace, renovated tile baths, sun-room, sauna, fireplace in master bedroom, cathedral ceilings, finished basement, and plenty of outdoor space, are among the many features this home offers. A detached 2-car garage with 15ft ceilings is perfect for boat storage. Above the garage is a spacious studio with cathedral ceilings and private second floor deck. A picture-perfect garden shed was fully renovated and features a covered porch, wood detail throughout, loft storage space, updated windows and is set up for year-round use. This is an investment opportunity not to be missed!

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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17 Jessica Lane Oak Bluffs MA

Oak Bluffs, MA17 Jessica Lane

Price$1,500,000

Est. Mortgage: $/month

MLS Number 36761

  • Residential
  • Square Feet 3020
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Get the most for your money! Over 3,000 sq ft. with all the features you may desire...Open, great room floor plan complete with gas fireplace in the living area, radiant "in floor" heat plus central AC, main level master bedroom with private porch, a massive rear deck and inviting covered front porch providing extended living areas and an enchanting water feature that includes Koi fish of all colors & and a babbling waterfall! Also, SOLAR Panels and a refreshing outdoor shower. Nicely nestled at the end of a private country lane not far from everything that is "down island", this is the right place for vacation or year round living. Beautiful gardens galore and quick access to the many hiking trails nearby. Solar panels and outdoor shower too! Plenty of room on the 1.3 acres for a guest house (with town permits) or a pool. Close to bike bath and Farm Neck Golf Course. This is one "opportunity knocking" that you don't want to miss.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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5 Winona Avenue Oak Bluffs MA

Oak Bluffs, MA5 Winona Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 35684

  • Residential
  • Square Feet 1524
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.35

RARE WATERFRONT setting on the Lagoon - perched up high on the hill, facing westward with expansive views, views and more views! Private and tucked away yet surprisingly convenient, this vintage single level home and cottage "bunk house" is a dreamy island retreat. Welcoming and open from the first steps inside, the main great room leads to water view sliders and a deck across the entire back. Grassy yard and mature plantings enhance the truly beautiful views of the Lagoon, Hines Point and Vineyard Haven harbor beyond. Perfectly sited to take advantage of this unique setting. Direct access to the Lagoon waterfront beach by way of a sturdy, large timber staircase. Look no further - you've found Home Sweet Vineyard Home! Open for showing appointments July 21st and after with notice!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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5 John Wesley Avenue Oak Bluffs MA

Oak Bluffs, MA5 John Wesley Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 36768

  • Residential
  • Square Feet 2600
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

MOVE IN THIS SUMMER! BRAND NEW HOME located in East Chop within walking distance to Oak Bluffs Harbor, Jetty Beach, Town, Shops and Ferry Ports! Custom Design with 4 BEDROOMS 4.5 Tiled Bathrooms with a SPACIOUS living and dining area! Over 2600 square feet of living space ! The kitchen includes TOP of the line APPLIANCES and beautiful cabinetry throughout! There is a finished walk out basement with about 1000sqft with access to a huge patio for entertaining BONUS a walk up LARGE un finished attic space offer options for the SAVVY BUYER ! Attached one car garage completes this offering! MANY BEAUTIFUL TOUCHES THROUGHOUT ! RARE OFFERING in this LOCATION & SIZE!! ** single split rail fence framed with roses will line the front yard. There is a patio in the backyard more photos coming soon and 360 tour!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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55 Worcester Avenue Oak Bluffs MA

Oak Bluffs, MA55 Worcester Avenue

Price$1,389,000

Est. Mortgage: $/month

MLS Number 35514

  • Residential
  • Square Feet 2446
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

NEW CONSTRUCTION - WALK TO WATER - Custom Three Bedroom, Three and a Half Bath Home with extensive interior trim including wainscoting, coffered ceilings and rustic beams. This house has a significant amount of features not typically found in this price range! The entire ground floor is L-Shaped with two living areas on opposite sides of the house, the kitchen being the central point. The main Living Room will have a Coffered Ceiling, Hardwood floors, direct access to a huge deck and a propane Fireplace. The Custom Kitchen will have Quartz counters, Stainless Steel Appliances and Rustic Beams. Two dining areas, one formal, one informal, provide a transition into each of the living areas. (See Floor Plans in Photos). Second Living Area/Den with built-in bookcases. Shiplap clad entrance hallway with half bath. Wainscoting throughout the main living level. Upstairs, two story landing overlooks the entrance hallway. There are Two Bedrooms with Ensuite - each have their own private bathrooms and private balconies. A loft, third living area upstairs which leads to a Third bedroom, both of which share the full guest bathroom. Custom tile work throughout. Full size windows in full basement and exterior access to back yard and outdoor shower. Forced Hot Air heat and Central Air-Conditioning. Huge mahogany Deck 12ft x 40ft.. Two Car Garage and off street parking. A short walk to the end of the road and you'll be at the Beach on the Lagoon - Great for swimming and boating - a Big Plus for renters! Minutes to bike or to drive to downtown Oak Bluffs and Ferry. Progress photos will be added regularly. Easy to Show! (Taxes only reflect land assessment.)

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 Eastville Avenue Oak Bluffs MA

Oak Bluffs, MA10 Eastville Avenue

Price$1,149,000

Est. Mortgage: $/month

MLS Number 34837

  • Residential
  • Square Feet 1966
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Walk to Town from this lovely 'Like new' four bedroom Home, with 2 Master Bedroom Suites (6 Bedroom Septic System) on an oversized 15,000 sq.ft. lot. Main living level has an open floor plan with clearly defined spaces. Living room has an Aspen Fieldstone clad fireplace, Bluestone hearth, crown molding, custom cabinetry for audio/visual equipment, recessed downlighters and beautiful rustic American Cherry floors that only get better with age. Breakfast area adjacent to the Kitchen leads directly to mahogany deck. Kitchen cabinets are a lovely Caramel Colored Maple with Giallo granite counter tops. The matching island provides great additional space to work on, or to sit at to keep the chef company. Kitchen leads to a separate dining room with built-in mirror feature and rustic cherry floors. Half bath w/travertine tiles, wainscoting and laundry. Also direct access to a one car garage with an automatic garage door opener. Second floor has two Master Bedrooms each with an ensuite. Two additional guest bedrooms share a guest bathroom. Each bathroom has travertine flooring, custom tiled baths/shower and granite counters. Berber carpet provides a soft touch in each bedroom, along with ceiling fans and recessed downlighters. Propane forced Central Air and Heat throughout. Basement is framed to accommodate two more bedrooms and a bathroom. Egress windows are already place for safety and additional light and ventilation! Town approval required in order to complete. Guest house potential when owner complies with town requirements. Asphalt driveway. Irrigation system around perimeter of house. Mahogany clad outdoor shower! Minutes to Eastville Beach, Oak Bluffs Harbor, the Ferry, Hospital and downtown restaurants and activities. Contents available for purchase separately. Room for a POOL! Easy to show.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

5 Upper Meadow Lane Oak Bluffs MA

Oak Bluffs, MA5 Upper Meadow Lane

Price$1,135,000

Est. Mortgage: $/month

MLS Number 35923

  • Residential
  • Square Feet 2072
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.81

This Meadow View Farms home offers tremendous value with lots of family space, 3+ bedrooms, and a spectacular, oversized post & beam garage with over 800 sq feet of additional living space above. Solar panels on the garage installed by South Mountain have significantly reduced year-round electric expenses. Meticulously maintained inside and out, this delightful home is attractively sited on .81 acres on a private cul-de-sac. The first floor offers a formal living room with gas fireplace and cathedral ceiling, dining room opening to a sun-filled kitchen, family room with tray ceiling, and glass doors leading to an inviting three-season screened porch. The first floor also features 2 guest bedrooms and a full bath. The second floor offers a master bedroom with en suite bath and large loft with full bath and laundry room. The beautifully landscaped yard features a striking Belgian block-lined driveway and front walk, garden shed, and a variety of trees, flowers gardens, and wild flowers. Located in a Private Association with tennis courts, near miles of walking trails, bike paths, Farm Neck Golf Club, and easy access to downtown Oak Bluffs. Look no further, this home has it all!

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

34 Waterview Road Oak Bluffs MA

Oak Bluffs, MA34 Waterview Road

Price$1,125,000

Est. Mortgage: $/month

MLS Number 35933

  • Residential
  • Square Feet 1559
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2775

Waterview Farms - Water views from both living levels and expansive deck, walk to private association beach, kayaking, boarding and common lands from this ideal location. Adjacent to Farm Neck golf course if golf is your passion. This architecturally fabulous three-season home is set on a quiet meadow with views of 2.5 mile Sengekontacket coastal pond and Nantucket Sound beyond. Tastefully renovated, air conditioned home creates the ultimate Vineyard experience. With shiplap cathedral ceilings and walls, large windows, and three sets of sliders to oversize deck, the house lives large. It offers incredible natural light throughout the day. The open living room, dining room, and kitchen take advantage of the water views and exceptional wraparound deck. The master en suite is away from the heart of the house for privacy. It features a water view, sliders to the deck and outside shower. A cozy guest room, full bath, and laundry complete this floor. A delightful second floor suite will keep your guests coming back to visit. This large bedroom features a full bath, unique angles, skylights, and a relaxing loft to take in the panoramic water views. This property has a strong rental history and unique Vineyard appeal.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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40 Hidden Cove Road Oak Bluffs MA

Oak Bluffs, MA40 Hidden Cove Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 36017

  • Condominium
  • Village Sengy
  • Square Feet 2690
  • Bedrooms 3
  • Bathroom 2

This newly renovated Hidden Cove condo unit is located in an area that includes private pool, tennis, and access to a boat launch on Sengekontacket Pond. Many nice features include all new kitchen and baths, new flooring, carpeting and a new heat pump system for heating and cooling. The main level offers an open kitchen and dining room, living room with fireplace both that open to a private deck and offering stunning ocean and pond views. Second floor is the master suite, lower level includes 2 bedrooms, both with access through sliders to a private patio. Stunning ocean and pond views from each floor. There is also an oversized 1-care garage that includes additional storage of bikes and out door furniture.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

33 June Avenue Oak Bluffs MA

Oak Bluffs, MA33 June Avenue

Price$1,100,000

Est. Mortgage: $/month

MLS Number 36553

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1871
  • Bedrooms 3
  • Bathroom 3

Custom Craftsmanship in Oak Bluffs with quick access to the Lagoon Pond. This custom home has an open floor concept that has a natural flow throughout with Kitchen/living/dining. The chef's kitchen is ideal for those who have a passion for cooking and right off the kitchen you will find a screened-in porch perfect for those summer nights. The second floor is where you will find all three bedrooms. There is a shared bathroom for both guest bedrooms. The master is located at the end of the house and has its own private balcony perfect for your morning coffee or tea. The basement has both interior and exterior access and has been outfitted with egressed windows to provide natural light throughout. You will also find a full bathroom as well as the stackable washer/dryer unit. 24 hrs required for all showings at this time.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

22 Old Harbor Lane Oak Bluffs MA

Oak Bluffs, MA22 Old Harbor Lane

Price$1,100,000

Est. Mortgage: $/month

MLS Number 36734

  • Residential
  • Village Sengy
  • Square Feet 1833
  • Bedrooms 4
  • Bathroom 2

Year-round living in Waterview Farm! This 4 bedroom home is a short distance to the association beach and dock, and enjoys spectacular sunset views over a beautiful 10 acre, forever wild meadow. Many upgrades over the past few years make it move-in ready, and it has a very strong rental history, grossing over $40,000/season. Extend your own season or enjoy the peaceful bliss and stark beauty all year long. SHOWINGS ON SUNDAYS BETWEEN 10 & 2 - MASKS AND GLOVES MUST BE WORN.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

1 Bird Street Oak Bluffs MA

Oak Bluffs, MA1 Bird Street

Price$1,095,000

Est. Mortgage: $/month

MLS Number 36463

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 2330
  • Bedrooms 4
  • Bathroom 3

INVITING WITH COASTAL FLAIR! Tucked away yet walking distance to Oak Bluffs village amenities, harbor and beaches! The stonework, gardens and tidy brick path lead to the door of this charming expanded cape. Beautifully designed and maintained, this sturdy lightly used four bedroom home is open and spacious. Facing South the sunshine streams in and the many stylish details shine bright. Generous great room, exceptional kitchen design with quartz countertops and custom cabinetry. Two Bedrooms on the first floor take advantage of easy access with glass doors to the private yard and mini oasis of easy care plantings! Newly completed second floor has two enormous bedrooms, each ensuite with tons of closet space. All this plus a fabulous cedar outdoor shower and an attached garage - come see how sweet Island life can be!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details