Oak Bluffs Homes $1.5M+

Learn More About Oak Bluffs MA

View Martha's Vineyard homes for sale in Oak Bluffs priced at $1.5M and higher. You may also be interested in browsing all homes in Oak Bluffs.

Oak Bluffs Homes for Sale Over $1.5M

Call Ocean Park Realty at 508-693-4210 if you have questions about a listing or would like to see any of these properties in person.

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Under $600k | $600k-$900k | $900k-$1.5M

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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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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: 7.19% last updated on Sep 21, 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: 7.19% last updated on Sep 21, 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

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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: 7.19% last updated on Sep 21, 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

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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21 Hudson Avenue Oak Bluffs MA 02557

Oak Bluffs, MA21 Hudson Avenue

Price$2,950,000

Est. Mortgage: $/month

MLS Number 41237

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 5.5
  • Acreage 0.4399

This is a rare opportunity to own a large rental facility, and a two bedroom oversize apartment. On one side, there is a large two bedroom two bath apartment with an older, gourmet kitchen and two amazingly large size Bedrooms. On the other side is six bedrooms with three baths facility each bedroom having 2 to 3 beds with a total of 25 beds in the whole facility. It comes completely furnished and is turnkey. Originally set up for the Pequot Hotel as the owner’s apartment and housing for the entire staff of Pequot. Below is a large storage facility with half bath and office with 11 foot ceilings and completely shelved. The photos of the below space show the storage before everything was cleaned out. This would be great for a small business or a restaurant or hotel to take care of all your rental needs.

Listed by Fred Mascolo of Jane Brown Assoc.

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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 Mayhew Way Oak Bluffs MA 02557

Oak Bluffs, MA3 Mayhew Way

Price$3,149,000

Est. Mortgage: $/month

MLS Number 41195

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.7806

LOCATION, BEAUTY, PRIVACY AND EASE ... A unique, sprawling single story home sited in a private, gorgeous, landscaped property with a brand new custom pool 18x38, spa, and pool house 14x30. All designed by top Island design groups. The property is located in the desired Tower Ridge Private Community with abundant Common areas and right across from Farm Neck Golf Club. This is one of the best Island locations for easy and quick access to restaurants, shopping, bike paths, beaches, golf and tennis. From the house, you look through a wall of windows and French doors out to a large deck and blue stone patio, surrounded by Donaroma designed gardens and a beautiful stone wall. This area is back dropped by common area woodland and provides you with a sense of total serenity and seclusion. From the patio, you will look over lawn and gardens to the custom pool, spa and pool house totally secluded by landscaping and woodlands. As you step into the house, you enter a foyer that welcomes you into a great room with a large Rumford fireplace. On either side of the foyer, you have a room set up as a cozy TV room and a flexible room that is used as an additional sitting room, providing ample space for family or guests to spread out either in or outside the house. The great room flows into an open, airy dining space and the modern kitchen with a Bosch gas stove. The 3 bedrooms are separated so that the primary is away from the guest rooms and has a renovated bathroom with radiant floor heat. Additional unique features: —Attached heated 2 car garage — A gym with massage room — Pea stone driveway with granite aprons — New 4 bedroom septic —2 custom built outdoor showers, one off the Primary bedroom and the other attached to the pool house — Attached 3 seasons room open to the deck and patio — Granite patios surrounding the pool house and pool area — New pool house has both heat and air conditioning, full basement and remodeled shed provide great storage — New, extensive irrigation system — Unique and beautiful flowering trees provide color and enchantment from spring through fall. This is a unique property that you won't find anywhere else on Martha's Vineyard. Don't miss it.

Listed by Sheila Morse of Island Real Estate

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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 Beach Road Oak Bluffs MA 02557

Oak Bluffs, MA11 Beach Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 41088

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.22

Open active waterfront Vintage Cottage, featuring two bedrooms with the potential to add a private dock. Mooring available. In search of buyers to enjoy boating, swimming ,fishing, kayaking, paddle boarding living waterfront on Vineyard Haven Harbor! Watch the ferries passing to Woods Hole, the Black Dog Sail Boats and view spectacular sunsets over West Chop and beyond! Private sandy ,rose-covered beach as your backyard. A great investment property awaiting a builder/ home designer to renovate and FLIP or a family to enjoy as a quintessential charming Vineyard Cottage. The true value is the scarcity of oceanfront properties available in this price range on the Island. There exists a strong rental history "as is" in place and a vacant non-buildable lot abuts this property to increase your privacy.

Listed by Suzanne Lanzone of Suzanne Lanzone & Associates LLC

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$
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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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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9 Weston Avenue Oak Bluffs MA 02557

Oak Bluffs, MA9 Weston Avenue

Price$4,295,000

Est. Mortgage: $/month

MLS Number 41083

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.4

East Chop charmer. This property is nestled in the heart of East Chop and offers spectacular views of the Sound from the living room, screened porch, primary bedroom, and two large water-facing porches. You can watch the ferries coming and going and the sailboats cruising by. East Chop Drive is one of the island's favorite walking spots and it's right in front of this property. The house has been well cared-for and there is also ample opportunity to put your finishing touches on it. In addition to the 4-bedroom, 3-bath home there is a large garage that offers options for the future owner.

Listed by Bonnie Pierce of Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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! A Rare Opportunity to Own this Property in The Highlands in East Chop! Nestled in one of the most desired neighborhoods this exclusive four bedroom antique three season home with existing garage boasts the option for expansion. Owned by one family for the last 51 years this exquisite home exudes timeless charm and possesses remarkable unique architectural design and detail in each room with high vaulted ceilings, abundant natural light, beach stone wood burning fireplace, wood flooring, built in cupboards and closets throughout. 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. Be on Island Time with sounds of the sea hear the buoy's chime the ferry blasts and enjoy the wonderful breeze while entertaining and relaxing on the front porch. This will be your families 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 garage brings you Home. This is a rare and highly coveted Property! New electrical 200 amp service run underground as well as chase pipes phone/cable. Buyer is responsible for installing new Title V and Town Permitting. Don't miss this opportunity!!!

Listed by Janna O'Loughlin of Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 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 27, 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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