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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5 John Wesley Park Oak Bluffs MA

Price$1,649,000

Est. Mortgage: $/month

MLS Number 34510

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

EAST CHOP - Have it all, top tier craftsmanship and a phenomenal location! With dedicated attention to detail, this 2,600 sq. foot home features exquisite luxury finishes with every possible modern convenience, and is nestled in a most coveted East Chop enclave. It's truly the best of both worlds, brand new construction, in an iconic Martha's Vineyard setting. This beautifully proportioned home offers 4 generous bedrooms and 4.5 baths, as well as a 1,000 sq. foot ground level finished basement that provides even more living space, with lots of storage. The spacious open floor plan with 9 foot high ceilings is perfect for entertaining. The gourmet kitchen has center island with seating and flows easily to the dining room with dramatic coffered ceiling. The living room has multiple seating spaces. The attached garage conveniently stores your island car. The sweet back yard area will be hardscaped to flow seamlessly from the ground level finished basement space. And of course, the perfect finishing touch in this neighborhood is the subtle and inviting front porch. Is there anything more quintessentially “east chop” than rocking in a chair and greeting your neighbors as they stroll through these quiet, timeless avenues? You and your guests will be walking to the beach (.5 mile), the harbor (.56 mile), the Lighthouse (.75 mile), and possibly spend just as much time in downtown Oak Bluffs as you will in this stunning home.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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 Tower Ridge Road Oak Bluffs MA

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

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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7 Old Harbor Lane Oak Bluffs MA

Price$1,590,000

Est. Mortgage: $/month

MLS Number 35090

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1
  • Acreage 0.8

VIEWS, VIEWS, VIEWS! This wonderful summer vacation home offers views in every direction whether it's Sengy Pond, State Beach, Nantucket Sound, or natural preserve open space, you'll be captivated by each vista. This retreat boasts inviting, spacious, vaulted ceilings, light and bright bedrooms that each look to the water offering summer living at its best. Bask in the rising sun from one deck and the setting sun from the other deck! LOCATION! This parcel adjoins conservation land offering unobstructed views that reach all the way to Sengy Pond, State Beach and beyond. Waterview Farms is centrally located between three towns; Oak Bluffs, Vineyard Haven & Edgartown yet still very private being an exclusive community adjacent to Farm Neck Golf Course. This neighborhood provides beach access with boat storage and docking available. This spacious parcel is great for events & parties, or flying kites & out door games. Explore quaint nearby walking trails to Pecoy Point, or use your paddle board or kayak to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! Two adjoining build-able lots may be available for purchase, please inquire. Owner carry financing available. Agent holds interest in property.

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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55 Worcester Avenue Oak Bluffs MA

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. 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 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 Master Bedrooms - they each have their own private bathrooms and private balconies. There's also a third living room upstairs which leads to a Third bedroom, sharing the full guest bathroom. Custom tile work throughout. Full size windows in part of the full basement. 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: 3.69% last updated on Oct 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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33 Beach Road Oak Bluffs MA

Price$1,375,000

Est. Mortgage: $/month

MLS Number 35787

  • Residential
  • Square Feet 1622
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.1899

Gorgeous waterfront cottage with deep water dock. This 4-bedroom home is a slice of paradise on Martha's Vineyard. Located on bustling Beach Road close to Eastville Beach, the home is a peaceful oasis once you have entered the home through the covered porch and closed the front door behind you. The property looks westerly over Vineyard Haven harbor and is blessed not just with fabulous water views and sunsets, but also an incredible vista filled with passing ferries, classic wooden sailboats, modern motor yachts, and all manner of small craft from kayaks to paddle-boards. These are also the waters where world class kiteboarders train for international competition and you can enjoy a front row seat to watch them swooping back and forth. The deep water dock has a 7' draft at low tide and has accommodated large boats. There is also a mooring close by. It is fitting that the setting should have such a strong nautical bent - the house was originally "Station #7" of the NY Yacht Club, a place where NYYC members could tie up their tenders and step ashore while visiting the waters around the Vineyard. The interior of the home is as quaint as you could possibly imagine, with painted beams, wainscoting, and the beachstone fireplace creating a distinctly Vineyard ambience. The ground floor master bedroom suite is spacious, and there are three additional bedrooms upstairs, including one with a king size bed. Want to spend the day at the beach but be able to come home for lunch and go back again - well, popular Eastville Beach is virtually next door, just 600 feet away. The current owners have cared for the house well, and made many improvements since purchasing it, including renovating the kitchen and bathrooms, lining the chimney, putting on a 40-year roof, replacing all upstairs windows, replacing the plumbing and wiring, replacing appliances in the last 2 years, replacing Rennai gas monitor in the last 2 years, and more. LEXAN window shutters increase the cottage's 'weather tightness' and allow you to use the cottage from spring to fall. Note that present and future owners of this property have the right to maintain and/or replace their licensed dock and seawall.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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7 Quail Run Oak Bluffs MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 34677

  • Residential
  • Square Feet 2877
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Custom Contemporary Design!! ! This home shows like a new home! IMMACULATE Residence impeccably maintained is in the desirable Sengekontacket Community of Oak Bluffs! This Exquisite custom design, comfortably on one level, is situated on almost an acre of land with mature landscaping, stone walls and colorful perennial flower beds. Enter an impressive foyer into an OPEN BRIGHT living room highlighted with a beautiful stone European wood burning fireplace and 12 ft ceilings. CENTRAL AC ! The interior design is complemented by attractive furnishings that add to the graceful flow of the floor plan. Gracious Master Suite and 2 additional bedrooms are all spacious and inviting with custom closets, the kitchen is large with high end appliances, and there is a cozy separate den, and a dining room with sunsets. SURPRISE! There is a lower level, fully finished, offering a large media/rec room and multiple gathering spaces along with a full tiled bathroom & spacious workshop with walk out access! TERRIFIC LOCATION with private amenities that include access to both fresh and salt water ponds, community dock, mooring available, with kayak storage and boat ramp, a community clubhouse on the fresh pond (available for private events), tennis courts, and community services such as curbside trash pick-up and snow removal. MUST SEE HOME!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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34 Waterview Road Oak Bluffs MA

Price$1,250,000

Est. Mortgage: $/month

MLS Number 35933

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

Waterview Farm - Waterfront neighborhood with association beach, boating, and common lands is an ideal location. The architecturally fabulous three season home is set on a quiet meadow with water views of Sengekontacket Pond and Nantucket Sound. A short walk takes you to the association beach. The owners lovingly renovated the home, creating the ultimate Vineyard experience. With ship lap cathedral ceilings and walls, six skylights, large windows, and three sets of sliders to an oversized deck, the house lives large. It offers incredible natural light throughout the day. The open living room, dining room, and kitchen are intentionally at the back of the house to enjoy the views and exceptional wraparound deck. The master en suite is tucked away from the heart of the house for privacy, with 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. There is a large bedroom with unique angles, skylights, full bath 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: 3.69% last updated on Oct 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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16 Clay Avenue Oak Bluffs MA

Price$1,225,000

Est. Mortgage: $/month

MLS Number 35869

  • Residential
  • Square Feet 1973
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.46

East Chop - Great location on a quiet street, built in 2008, 4-bedroom, 3-bathroom wood shingled Cape Cod style, with landscaped yard, situated in the heart of East Chop walking distance to beaches, tennis courts, Oak Bluffs harbor and downtown areas. Covered front porch opens into the main living/dining/kitchen great room with fireplace, high ceilings and walls of large windows providing a bright sunlit warmth throughout the day! Screened in porch on one-side and rear deck looks out on to private back yard (0.46 acres). Full-unfinished basement, outdoor shower, propane heat, A/C and irrigation system. Room for a pool but please verify all such plans with appropriate town departments. Home comes partially furnished. Septic Title V passed 9/6/19.

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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1 Bird Street Oak Bluffs MA

Price$1,159,000

Est. Mortgage: $/month

MLS Number 34308

  • Residential
  • Square Feet 2472
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.22

Location! Location! A short 5 minute walk to the ferry, movie theater, town, beach, harbor and library. Come view this private gorgeous newly renovated Cape style home featuring (4) bedroom (3) full baths, attached garage and over 2400 SF of living space. This pristine open concept home includes custom white kitchen cabinets with quartz countertops, center island with seating and a separate eat-in dining area. The kitchen space flows into an oversized family great room. The first floor includes 2 sunny bedrooms with glass patio doors that open onto a private relaxing side deck overlooking the side yard and custom Japanese gardens. The second floor is comprised of brand new construction that includes 2 master bedroom suites with large walk-in closets and 2 modern tiled bathrooms. The home radiates with morning and afternoon sun. Property includes a brand new private custom cedar outdoor shower and a new extra wide driveway with a cobblestone apron. The yard is surrounded by mature plantings that bring color all season long and plenty of privacy. This property is a the perfect investors dream or family Vineyard getaway!

Listed by Premier Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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 Eastville Avenue Oak Bluffs MA

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: 3.69% last updated on Oct 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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6 Rogers Way Oak Bluffs MA

Price$1,135,000

Est. Mortgage: $/month

MLS Number 35633

  • Residential
  • Square Feet 2300
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

NEW CONSTRUCTION - PRE-CONSTRUCTION PRICE! Currently in the process of being built on Rogers Way, Oak Bluffs, with a Fall Completion date. This is a lovely location, in a well maintained Association and within walking distance to Oak Bluffs Harbor and Circuit Avenue. This home will have three (3) bedrooms, three and a half baths (3.5), an Open floor plan, living room with fireplace, kitchen with island and breakfast area and a formal dining room/additional living room. Custom kitchen will have white painted cabinetry, Stainless Steel appliances, a gas stove and a large island with stone countertops, amongst other features. Breakfast area will lead directly to the back yard. There's also a half bath with laundry and access to a one car garage. Upstairs - Two Master Bedrooms with private bathrooms, tiled floors and wainscoting. There's a third bedroom, another full bathroom for guests, as well as a large loft for a third living space or entertainment area! Central air, hardwood floors throughout. Full basement - poured masonry foundation. Minutes to the Library. Great location for year round living, Summer vacation or weekly rentals! Walk to the Harbor, town and ferry from this very appealing location. Easy access to all island towns. Minutes to Eastville Beach and Town Landing off Shirley Avenue. Photos will be updated as construction progresses.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 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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5 Upper Meadow Lane Oak Bluffs MA

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 living space, 3 bedrooms, an oversized post & beam garage with additional living space above, and solar. Meticulously maintained both inside and out, this delightful home is situated on .81 acres and tucked away on a private cul-de-sac. The first floor offers a formal living room with gas fireplace, dining room which opens to a sun-filled kitchen, family room with cathedral ceilings and French doors leading to a welcoming screened porch. The first floor also features 2 guest bedrooms and a full bath. The second floor offers a large loft with full bath and laundry room, along with a master bedroom suite with private bath. The beautifully landscaped yard features a variety of trees, flower gardens, garden shed, and a field of wild flowers. Located close to miles of walking trails, bike path, 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: 3.69% last updated on Oct 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details