Oak Bluffs Luxury Real Estate

Find current luxury real estate in Oak Bluffs on Martha’s Vineyard. Contact Ocean Park Realty or call us at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour. Sign up for an account (it's free) to save your favorite luxury properties in Oak Bluffs and get notified when similar properties become available.

Oak Bluffs Luxury Properties For Sale

2 Great Rock Road Oak Bluffs MA 02557

Oak Bluffs, MA2 Great Rock Road

Price$1,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41373

  • Residential
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 1.528

Stunning Oak Bluffs Home Featured in MV Home & Garden - Welcome to a unique and charming piece of Martha's Vineyard history, where design meets authenticity and creativity flows freely. Nestled in a magical country garden setting at the end of a winding road in a secluded enclave of Oak Bluffs, this nearly 1,400-square-foot, three-bedroom house isn't just a home; it's an inspiring narrative. The timber-framed beauty from the mid-1800s was moved beam by beam from its original location nearby, painstakingly disassembled and reassembled in its current location, giving it a new lease on life. Original details and repurposed additions seamlessly blend together, exuding an aura of history and happenstance. The entry to the home is a custom-built solarium, completely rebuilt in 2022, featuring Marvin windows, Velux skylights, a custom-painted concrete floor, Eastern white pine framing and beams, oak stairs, stainless cable railings, custom matte black door hardware. While the house may still have a few renovations on its horizon, many updates have been thoughtfully and artfully made over the last few years. Centrally located, all of the wondrous and plentiful offerings of the island are just minutes away. It is a life where every moment is an opportunity to create, to design, and to breathe deeply, much like the gentle exhale of the Vineyard itself.

Listed by Leslie C. Floyd 508-221-4643 of Portfolio Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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: 7.31% last updated on Sep 28, 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 Sean Federowicz of Landmarks at TODAY Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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7 Fairway Drive Oak Bluffs MA 02575

Oak Bluffs, MA7 Fairway Drive

Price$1,395,000

Est. Mortgage: $/month

MLS Number 41326

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.1918

Charming four-bedroom cape centrally located in Oak Bluffs. The well-maintained home offers inviting living spaces, generous-sized bedrooms, and a manicured yard with a large garden shed. The finished lower level, with a private walkout, serves as the perfect quiet office or additional recreation space. The best of both worlds as the quiet neighborhood provides easy access to all down island amenities- bustling main streets, beaches, and ferry!

Listed by Katherine Donahue of Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$1,975,000

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 Amber Henry of Engel and Volkers Boston

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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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 Hope's Way Oak Bluffs MA 02557

Oak Bluffs, MA4 Hope's 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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$1,650,000

Est. Mortgage: $/month

MLS Number 40907

  • Residential
  • Mls Status Active
  • 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 Michele Moore of Island Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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267 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA267 Barnes Road

Price$5,850,000

Est. Mortgage: $/month

MLS Number 39954

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 5.5
  • Acreage 1.25

Enjoy waterfront living at its best with 163’ of Lagoon frontage including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning waterviews and spectacular sunsets. This is your time to enjoy Vineyard life on the water…boating, swimming, kayaking, clamming, and more. Perfect for entertaining and comfortable living, the immaculate 4,046 square foot home with a newly finished 2,000 square foot walk-out basement has a wonderful flow throughout and waterviews from almost every room. It was designed to capture the essence of waterfront life. It is rare to find a home in a setting like this on Martha’s Vineyard. Tucked away just off Barnes Road, it feels as if you are in a remote locale, yet close to all the Island has to offer. The main level, with soaring ceilings, is comprised of a large living area enjoying a wood-burning fireplace and wet bar, a sitting area, half-bath, dining room, and a large kitchen with eat-in dining, with full views of the Lagoon and access to the outdoor patio. Two additional rooms with a private deck and full bath are cleverly located in a separate wing of this floor and can be used as an office or den. Unique to the second floor is a wraparound deck and screened porch overlooking the Lagoon and adjoining the large primary suite with a second wood-burning fireplace and two spacious ensuite bedrooms, all with fabulous views. If you are looking for a quiet space, you can enjoy a second covered porch at the front of the house. Being sold furnished, this is the ultimate Vineyard Experience.

Listed by Stephanie Roache of Donnelly + Co

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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55 Tuckernuck Avenue Oak Bluffs MA 02557

Oak Bluffs, MA55 Tuckernuck Avenue

Price$1,065,000

Est. Mortgage: $/month

MLS Number 41301

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.053

Quintessential in-town charmer! Antique farmhouse style, fronting Niantic Park, close to all that Oak Bluffs has to offer by way of beaches, parks, eateries, shops and ferry service. Three bedrooms plus a "flex" room, a comfortable sitting porch, and a rear patio facilitate enjoyment of the casual Vineyard lifestyle. Located within the Copeland and Cottage City Historic Districts.

Listed by Sean Federowicz of Landmarks at TODAY Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA11 High Meadow Lane

Price$1,950,000

Est. Mortgage: $/month

Open House

MLS Number 41296

  • Residential
  • Next Open House: Sat 10/7 11:00 am. to 1:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5

Lovingly cared for home located in a private setting tucked back from the road on top of a hill in Meadow View Farms. Close to Bike paths miles of walking paths, Farm Neck, Downtown Oak Bluffs and all that the Island has to offer. Well run association with Tennis and Pickleball courts. The contemporary designed Home features a bright open living area with cathedral ceilings, oversize windows, adjacent dining area, and kitchen leading to the exterior deck, outdoor shower and backyard. Featuring a large first floor primary suite with three more bedrooms with one full bathroom on the second floor and a loft study overlooking the living room, central air and heating throughout. Also includes irrigation system, outdoor shower and storage shed. Custom blinds finish off this move-in ready home. Excellent summer rental history. Furniture & contents may be available for a turnkey , easy occupancy.

Listed by Amy Goldson 202-251-2922 of Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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33 Menahan Street Oak Bluffs MA 02557

Oak Bluffs, MA33 Menahan Street

Price$1,185,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41265

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.1147

Charming three-bedroom, two-bath Cape moments away from downtown Oak Bluffs, with the shops, restaurants, beaches, and lively harbor attractions all close by! This well-maintained home, casual in design, offers an open-concept first-floor layout ideal for year-round or vacation use. A large fenced-in backyard extends the seasonal living space, perfect for those quiet summer nights, four-legged friends, and younger generations. A wonderful opportunity!

Listed by Katherine Donahue of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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 Winthrop Avenue Oak Bluffs MA 02557

Oak Bluffs, MA31 Winthrop Avenue

Price$1,099,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41201

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.3699

OAK BLUFFS, short walk to town. Stylishly Renovated Charmer with over 1646 Sq ft of Living Space 2 + bedrooms & 2 full bathrooms. Situated on an oversized(.34acre) landscaped, fenced level corner lot with an abundance of outdoor living space. Exceptional interior features include a warm and welcoming spacious first floor primary en-suite that includes custom built-in storage, cozy loft area and a striking tiled bathroom. The second floor includes a bedroom and bonus flex room. Additional features include an Energy Efficient Heating and Cooling System that is a central forced air heat pump(electric) installed in 2017. The model is Carrier Infinity Green Speed. Move-in ready and terrific investment opportunity with an established rental history! ALL OFFERS MUST INCLUDE a PRE APPROVAL and or PROOF of FUNDS .

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to LINKMV as of September 28, 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.

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