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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3 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA3 Canonicus Avenue

Price$2,495,000

Est. Mortgage: $/month

MLS Number 41509

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.0899

WATER VIEWS!!! Steps to the Beach - walk along the most scenic drive on Martha's Vineyard! This stunning property is a true gem, offering an exceptional combination of classic charm, modern amenities, and an ideal location for enjoying the island's relaxed lifestyle. Nestled in the heart of Oak Bluffs, this home is a short stroll to beaches, restaurants, and shops. The scenic harbor and parks are also just moments away, making it perfect for experiencing the best of the Vineyard. This renovated antique home boasts timeless architectural features and a welcoming front porch creating an inviting and picturesque curb appeal. The interior is a blend of elegance and modern convenience offering an inviting atmosphere for family and friends to gather. Enjoy the serene outdoor spaces, including a patio area for outdoor dining and rooftop deck (widow's walk) that features panoramic ocean views! With its prime location and strong rental income history, this property can serve as both your idyllic vacation retreat and a smart real estate investment. Don't miss the garage and surprise bonus area. Come experience the timeless allure of Martha's Vineyard, and make this extraordinary property your island haven. OWNER FINANCING IS AVAILABLE.

Listed by Compass | Point B

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$2,295,000

Est. Mortgage: $/month

MLS Number 41067

  • Land
  • Mls Status Active
  • Acreage 1.867
  • Bedrooms 6
  • Bathroom 6.5

THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground utilities and town water in place and each lot has been approved for up to six bedrooms per Oak Bluffs Board of Health. A peaceful and private setting abutting conservation land and trails for hiking, walking and biking! Don't wait to bepart of this lifestyle!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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19 Wendall Avenue Oak Bluffs MA 02568

Oak Bluffs, MA19 Wendall Avenue

Price$2,289,000

Est. Mortgage: $/month

MLS Number 40661

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.307

Location Location Location! Quick stroll to the beach and to Town just 0.3 miles to Harbor & East Chop Drive! Opportunity in The Highlands in East Chop!!! This exclusive four bedroom one and a quarter bath three season home with existing garage boasts expansion option to six bedrooms. This home exudes relaxing timeless charm and remarkable architectural design with high vaulted ceilings, abundant natural light, beach stone wood burning fireplace wood flooring built in cupboards and closets throughout. Quiet and peaceful set high on the Bluff this large Lot is sheltered by an additional 12,197SF of East Chop Conservation land, a lovely moat of mature plantings, adding greater privacy to the Property. On Island Time with sounds of the sea hear the buoy's chime and the ferry blasts. Enjoy the wonderful breeze while entertaining and relaxing on the front porch extended living area. Your MV beach retreat for many generations to come. Navigate with quick access, OB harbor, beaches, EC Tennis, EC Beach Club, Downtown, restaurants, clubs, shopping, and multiple Ferry Terminals. Driving up the custom laid brick driveway to the existing garage brings you Home. A rare and highly coveted Property!!!

Listed by Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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2 Farm Path Oak Bluffs MA 02557

Oak Bluffs, MA2 Farm Path

Price$2,250,000

Est. Mortgage: $/month

MLS Number 41356

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.89

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard and a pool! The large detached two-bay garage has a new attached studio with full bath, laundry, kitchen and a private deck. Newer exterior cedar shingles and trim, and a new 4 bedroom septic installed. Equidistant to each down-Island village, it resides within a mature neighborhood with attractive curb appeal.

Listed by Landmarks at TODAY Real Estate

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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28 Rogers Way Oak Bluffs MA 02568

Oak Bluffs, MA28 Rogers Way

Price$2,100,000

Est. Mortgage: $/month

MLS Number 40849

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.2299

UNDER CONSTRUCTION, contemporary farmhouse style home with wrap around deck and outdoor shower. This home features a first floor en-suite bedroom with a full bath, a half bath off the foyer entry, an open kitchen/dining and living room area with a gas fireplace, a wall of glass with windows and sliding glass doors from the dining area and living room area. There is a well designed mudroom area with a first floor laundry, a large overflow pantry and a built in bench seating area. The second offers two en-suite bedrooms, a large second floor living room area and a second laundry area. A full poured foundation with a walk out door completes this new construction offering. The property location offers close proximity to the center of town, beaches, and bike paths. This quiet location, with attractive homes, is convenient to everything that Oak Bluffs has to offer. Come and enjoy NEW CONSTRUCTION with COASTAL STYLE!

Listed by Vineyard Village Realty

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Paddock Road (lot 15) Oak Bluffs MA 02557

Oak Bluffs, MA34 Paddock Road (lot 15)

Price$2,000,000

Est. Mortgage: $/month

MLS Number 40763

  • Land
  • Mls Status Active
  • Acreage 2.059

The Preserve at the Woodlands - A terrific opportunity to build to your specifications in an exclusive and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. Abutting dedicated open space on two sides with a southern exposure, the orientation is perfect for a backyard pool and patio. The lot has been perk tested and is ready for you to build your ultimate Vineyard compound. The Preserve Homeowners Association is well organized with a strong financial foundation and is presently commencing a beautification initiative to further enhance the entrance and open spaces.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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4 Hopes Way Oak Bluffs MA 02557

Oak Bluffs, MA4 Hopes Way

Price$1,949,900

Est. Mortgage: $/month

MLS Number 41339

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 2.5
  • Acreage 0.2645

~UNDER CONSTRUCTION- BRAND NEW~ Located in LAGOON RIDGE "Oak Bluffs NEWEST NEIGHBORHOOD" - EXCEPTIONAL offering in a community with all new homes perched 95' above the Lagoon! Easy access to all the down island towns, beaches, shopping, ferry ports and harbors! Featuring a Stylish and Spacious Primary En-suite Bedroom on each floor, functional and convenient second floor office/ Flex Room, and 2.5 Tiled Bathrooms are included in over 2,400 square feet of prime living space. On the exterior you are greeted by the grand covered wrap-around porch that heightens one’s sense of arrival and provides the perfect setting for enjoying those cool summer breezes and refreshing morning air. Architecturally designed that leverages a smart and efficient floor plan that connects its chef’s kitchen to living and dining areas forming a generous space to host large gatherings of family and friends where life-long memories will be made. Top of the line finishes include 5" wood flooring, crisp white cabinetry, ACRE Flooring (a revolutionary new eco-friendly building material that is an alternative to wood) and a striking double-sided fireplace. RESORT LIVING with So MUCH STYLE! MORE PHOTOS COMING SOON!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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3 Poplar Lane Oak Bluffs MA 02557

Oak Bluffs, MA3 Poplar Lane

Price$1,799,000

Est. Mortgage: $/month

MLS Number 40267

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 0.6279

Gracious Colonial in Oak Bluffs - This spacious home in Vineyard Hills is waiting for you to make it your own. The home features 3 floors of living space that include 5 bedrooms and 3.5 baths. There is 2,380 sq. ft. of living space on the first 2 floors PLUS an additional 600+ sq. ft. in the walk-out lower-level in-law space. The backyard is an oasis with tiered landscaping, an in-ground pool, deck, pergola with trumpet vines, and a large, partially finished shed that can be transformed into your pool house. There have been many improvements over the last couple of years, including a new furnace, new hot water heater, new stainless appliances with gas cooktop and double wall ovens, a new 5 bedroom septic, new windows, and doors, remodeled full bath and powder room, and more. The first floor features a kitchen, dining, den/office space, mudroom with laundry, and living room with gas fireplace. Sliding doors from the living room and dining area open to a deck. The second floor features a primary bedroom en suite bath and a walk-in closet. Three additional bedrooms with a shared hall bath complete the second floor. The partially finished, walk-out lower level has a kitchenette, the 5th bedroom, and an additional living room that opens to a private deck. The lower level is also home to the new furnace and hot water heater as well as plenty of storage and a bulkhead. This house is waiting for you to make it your Vineyard home. Vineyard Hills has deeded beach rights to a quiet beach on the Lagoon. Homeowner will give a credit at closing towards 5-years of association fees.

Listed by Island Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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31 Double Ox Road Oak Bluffs MA 02557

Oak Bluffs, MA31 Double Ox Road

Price$1,650,000

Est. Mortgage: $/month

Pending

MLS Number 38671

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.3502

TO BE BUILT on Lot 13 NAUSHON *** Larger Lot and a WALK OUT BASEMENT ~Featuring 3 bedrooms and 3 ½ bathrooms, offering over 2,400 square feet of living space, the Naushon is the flagship of the Homes at Lagoon Ridge. A grand, covered wrap-around porch at the front of the home heightens one’s sense of arrival and provides the perfect setting for enjoying those cool summer breezes and refreshing morning air. The Naushon leverages a smart and efficient floor plan that connects its chef’s kitchen to living and dining areas to form a generous space to host large gatherings of family and friends where life-long memories will be made. All three-bedroom suites feature tiled ensuite bathrooms with quartz surfaces, Kohler fixtures, and spacious closets, while the Naushon’s second floor suites offer the option for private bedroom balconies. The Naushon’s classic lines pay homage to the cottage history of Oak Bluffs while offering all of the benefits of modern technology and comfort. The Naushon is the realization of your island dream. **See Interactive Virtual Tour Attached ** See Lagoon Ridge Website** Options are available for many too**Call for an appointment and private tour. Don't wait RESERVE YOUR HOME TODAY!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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11 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA11 Canonicus Avenue

Price$1,650,000

Est. Mortgage: $/month

MLS Number 41344

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 1.5
  • Acreage 0.16

LOCATION LOCATION LOCATION! Nestled on the picturesque island of Martha's Vineyard, this historic charming 3-bedroom, 1.5-bathroom single-family home is a tranquil oasis awaiting your arrival.The location of this home is truly exceptional. Oak Bluffs is known for its vibrant community, stunning beaches, and a wide array of dining and entertainment options. You'll be just moments away from the bustling downtown area with its shops, restaurants, and cultural attractions, making it easy to enjoy all that Martha's Vineyard has to offer.Visionaries take note!11 Canonicus Ave offers you a gorgeous water view with access to the beach, a wrap around porch and an expansive backyard. The heart of this home is the spacious sun filled dining area that offers tons of natural light. Whether you're looking for a year-round residence or a seasonal retreat, 11 Canonicus is a rare find that offers both comfort and convenience in one of New England's most coveted islands!

Listed by Engel and Volkers Boston

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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25 Inca Road Oak Bluffs MA 02557

Oak Bluffs, MA25 Inca Road

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number 40907

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.2295

Thoughtfully renovated from top to bottom, inside and out, this 4 bedroom, 3.5 bath is ready for your move-in day. The custom kitchen with stainless appliances and quartz counters is open to the dining area. The first floor has an open-concept floor plan with a living room, dining area, and kitchen. The kitchen opens out to the spacious back deck and private, enclosed backyard. There is a first-floor primary bedroom with a beautiful en suite bath. All bathrooms are thoughtfully designed with beautiful tile. The first-floor shower has a glass enclosure. The laundry/powder room is on the first floor, off of the kitchen. The second primary bedroom has an en suite bath that mirrors the first-floor bathroom, with a tile shower and custom glass enclosure. Two additional, spacious bedrooms and a custom third full bath complete the second floor. The large, sun-drenched deck off the back of the house opens into the fenced-in backyard with irrigation. There is a full, walkout basement with the potential to finish. The other section of the basement has a new air handler for heat and central air. The yard has been thoughtfully landscaped with beautiful plantings and irrigation. Home is located just off the bike path and less than 2 miles to town. Truly a rare find in today's market.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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54 Cannahoot Street Oak Bluffs MA 02557

Oak Bluffs, MA54 Cannahoot Street

Price$1,575,000

Est. Mortgage: $/month

MLS Number 41535

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2295

Located on East Chop, in pristine condition and just a short walk to the beaches, tennis courts, yacht club/harbor, downtown restaurants and the ferries, is this contemporary style 2-bedroom main house, being sold partially furnished plus detached 1-bedroom/1-bathroom. The main house’ modern design features radiant floor heating, cathedral ceilings, modern kitchen, a central concrete block wall behind the floor to ceiling wood burning Rais-Wittus Shaker bench wood stove and access to exterior decks from both the main entrance and the downstairs bedroom. The steel staircase to the second floor is showcased by a wall of light from the hallway. The second floor features an ensuite master bedroom that has its own balcony deck with outdoor shower. It is located on 10,000 sq. ft. (0.23 acres), that includes a front and side yard and parking for 2-3 vehicles. New Title V septic installed 2022.

Listed by MV Luxury Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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Based on information submitted to LINKMV as of December 4, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.