Oak Bluffs Homes $1.5M+

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.

34 Windemere Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Windemere Road

Price$3,999,000

Est. Mortgage: $/month

MLS Number 38803

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.7242

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbath. Two story Beach Cottage, first floor kitchen leads to the dining, living and sunroom, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with waterview, Guest Bunk bedroom and Twin bedroom which both share full bath. Hardwood floors, waterviews throughout, new outdoor shower, Shed, and a Gazebo. Leases are in place for 2022 to be transferred to Buyer at closing. Easy to show.

Listed by JoJo Lambert of Island Home Realty Inc.

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%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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60 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA60 Pennacook Avenue

Price$1,550,000

Est. Mortgage: $/month

MLS Number 38838

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.06

Nestled in the heart of the Cottage City and Copeland Historic Districts, this antique home is within walking distance to everything. Beaches, Boats, Restaurants, Shopping, Playground, Basketball, Pickleball, Tennis, Parks, Bike Path and more. Watch the world go by as you laze on your shaded front porch after a day on the beach and a soak in the hot tub. This corner lot in a quintessential Victorian neighborhood offers much privacy overlooking Pennacook Park and much convenience with its central location. Assessors office has it as a 3 bedroom house. Oak Bluffs Wastewater has it listed as a 5 bedroom home already hooked up to Town sewer. Written documentation supporting 5 bedroom capacity available.

Listed by Christine Todd of Anchor Realty of Martha's Vineyard

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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113 Dukes County Avenue Oak Bluffs MA 02557

Oak Bluffs, MA113 Dukes County Avenue

Price$1,899,000

Est. Mortgage: $/month

MLS Number 32334

  • MultiFamily
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.0826

Rare offering IN TOWN OAK BLUFFS! Commercially Zoned multi family with a solid SUBSTANTIAL existing rental history. Built in 2017 in excellent condition and within walking distance to Oak Bluffs Harbor, Sandy Beaches, Art Galleries, Shopping, Restaurants and STEPS to Historic Martha's Vineyard Camp Meeting Association and Circuit Avenue! Recently, JULY 2021 NEW SOLAR PANELS! Features include State of the Art Energy Efficient Utilities and Low Maintenance decking, 1.5"closed cell foam insulation on the walls 3"closed cell on the roof and interior walls. Extremely energy efficient. Anderson Craftsmen series energy compliant. Energy Efficient Heat and AC Pumps throughout! Seller has not booked any rentals for 2022. FLEXIBLE INVESTMENT -HIGH RENTS & or CONDO CONVERSION..$$$$$$$$$$$$$$$ 3 Properties being sold as a multi family ! Unit A offers 2 BR1.5 bath, living/ dining area closets throughout partial basement, yard, decks, outside shower, energy efficient throughout ! Unit B is attached with 1 bedroom full bath and living area partial basement interior access, outside shower, yard energy efficient throughout! 3rd unit is a stand alone cottage with open bright high vaulted ceiling,1 bedroom and loft full bathroom energy efficient throughout! Notice required there are rentals in place call listing agent today. NEW PHOTOS COMING SOON! PHOTOS IN LISTING PRIOR to be FURNISHED..

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Atlantic Avenue Oak Bluffs MA 02557

Oak Bluffs, MA16 Atlantic Avenue

Price$2,095,000

Est. Mortgage: $/month

MLS Number 38261

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 2.5
  • Acreage 0.4971

Incredible Opportunity, Location and property. Main House and new Detached Studio and Full Basement. Atlantic Avenue is a short road that runs parallel to East Chop Drive, a block over from the East Chop Lighthouse and within earshot of the soothing sounds of the ocean. The Main house, built in 1890, is a classic example of traditional Victorian architecture and has been carefully restored to summer-living condition with painted ginger bread trim and a wrap around porch. A huge open kitchen w/cathedral ceiling is simple and functional. The back door off the kitchen leads to a screened in porch for alfresco dining and lounging. The beautifully refinished wood floors and leaded glass windows extol the simplicity and traits of days gone by. With 4 existing bedrooms and 1.5 baths, the house has been newly insulated and is painted waiting for your finishing touches. A brick fireplace and wide open living area will stir some creative juices and allow you to imprint your personal style of this neutral background. This property is being sold As Is. There is a new 7 bedroom septic system to allow for future expansion.

Listed by Kerry Quinlan-Potter of Breakwater MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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125 Sea View Avenue Oak Bluffs MA 02557

Oak Bluffs, MA125 Sea View Avenue

Price$2,497,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38620

  • Residential
  • Bedrooms 6
  • Bathroom 3.5
  • Acreage 0.1

Forever Views, Views and more Views! This Ocean facing Victorian home has sweeping water views across Nantucket Sound as well as Farm Pond. Loaded with charming details, the generous rooms offer ease for summertime gatherings and entertaining. Delightfully sited and expanded over time, the large welcoming porch sets the comfortable pace as each room flows to another. Front parlor, den, dining room, convenient laundry/storage room and a renovated kitchen - plus a multitasking overflow room with bathroom and a bedroom suite with private entrance at the rear. Front and back, the two staircases lead to the five bedrooms and two bathrooms. Plenty of convenient parking and easy access to the grassy backyard complete with BBQ area and outdoor shower. Impressive rental history, this treasured cottage style home is steeped in happy Vineyard vibes!

Listed by Helena Kirschenbaum of RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Montgomery Square Oak Bluffs MA 02557

Oak Bluffs, MA4 Montgomery Square

Price$1,500,000

Est. Mortgage: $/month

MLS Number 38541

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

Located in the heart of Oak Bluffs -Walk to the beach, town center, shops, and restaurants. A one-of-a-kind property on Montgomery Square in the MVCMA. This large building originally a store has a 16 X 31 artists studio in the front and 3 different living areas, there is space for the whole family to enjoy. With just under 2,000 square feet of interior space, 4 bedrooms, 3 bathrooms, a large private 2nd story deck, and covered porch below, 2 On-site parking spaces. A unique home and a great investment.

Listed by Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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400 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA400 Barnes Road

Price$7,300,000

Est. Mortgage: $/month

MLS Number 38540

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 2.417

The driveway sweeps up to the contemporary-designed 7,000 square foot home of luxurious open plan living on 3 levels with multiple rooms connecting you to outdoor entertaining patios and terraces. Relax in the infinity pool with waterfalls on 2 sides or the Spa pool while taking in the views of Lagoon Pond. The distinctive interior features generous living spaces designed with high open ceilings, full-length windows, exquisite materials, and high-end finishes throughout. Solar panels installed. There are 6 bedrooms, 5 bathrooms situated in areas throughout the floor plan to provide privacy when there is a full house. An elegant media and entertainment room with 106” flat-screen TV, full bar and wine cellar and a full bath. The gym is outfitted with professional equipment with a full wall of glass opens up to the outside lounging terrace and around to the pool and an outdoor rain shower. Enter from the two-car attached garage and an elevator provides a lift to the other living levels. The residence is surrounded by beautiful landscaping and terraced gardens, and further protected by the abutting 190 acres of the Land Bank Southern Woodlands property.

Listed by Kathryn Tate of Kendall & Kendall

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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47 Head of the Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA47 Head of the Pond Road

Price$1,695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38699

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.497

Meticulous craftsmanship, custom features and remarkable attention to detail by master carpenter owner/builder. Built in 1999, this 3 bedroom, two bath neat and pristine home decorated in Early American style with features like door transoms, hand-built exterior cedar shutters, pegged wood floors, custom-made beaded trim inside and outside, crown moldings, wainscoting, custom-built front entrance, reproduction cut nails and recently compacted and capped stately sea-shell driveway. Set well back from the road, surrounded by lawns and gardens, the main house is balanced visually by three outbuildings that comprise this remarkable compound that offers significant potential for a buyer looking for sizeable work and storage space. Allow lots of time for a showing because you'll need that time to absorb all the jaw-dropping details! Sellers in residence. Advance appointments and masks required.

Listed by Lynn Buder of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

31 Double Ox Road Oak Bluffs MA 02557

Oak Bluffs, MA31 Double Ox Road

Price$1,650,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38671

  • Residential
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Brewster Avenue Oak Bluffs MA 02557

Oak Bluffs, MA6 Brewster Avenue

Price$2,775,000

Est. Mortgage: $/month

Pending

MLS Number 38609

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.1147

Panoramic Ocean Views. This exceptional Victorian style family home and guest cottage has dramatic water views from inside and outside of its ideal location. A park across the way will remain park land in perpetuity, adding to the expansive feel and play opportunities that any family would cherish for a lifetime. The historic Victorian style family home built in 1883 was completely rebuilt in 2010 to allow for comfortable year round living. The 4 bedroom main house was carefully elevated and a full foundation was poured, winterizing with FHA heat and insulation. Impeccable care was taken in order to retain all of the vintage architectural features and details of the home while allowing for modern touches and comfort. Original built-in's, cross beams and wide plank floors protect the whimsical style of this much loved family home. The new full basement creates storage and safe keeping of utilities and the potential for additional living space if desired. Walk to town, beach, tennis and East Chop parkland including the historic East Chop Lighthouse. Facing a park, many evening games , laughter and joy have been tradition for this Vineyard family home.

Listed by Kerry Quinlan-Potter of Breakwater MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

71 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA71 Pennacook Avenue

Price$1,600,000

Est. Mortgage: $/month

Pending

MLS Number 38621

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathroom 2.5
  • Acreage 0.13

Classic Beauty in the heart of Oak Bluffs. The Pennacook House is set on a slight hill on a large landscaped yard.This year-round 6 bedroom, 2.5 bathroom home has a lovely eat in kitchen, formal dining and living room with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period detail and many upgrades throughout. Some upgrades include state-of-the-art propane Hot Water Heating system and Water Heater, new Electrical Panel and Service, new Dishwasher Irrigation in the lawn and flower beds and lots of painting inside and out. The full walkout basement has laundry and plenty of storage space. Great location just a few blocks from town center, ferries, harbor and beaches. Very strong rental history...Turn Key!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

8 Hopes Way Oak Bluffs MA 02557

Oak Bluffs, MA8 Hopes Way

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38617

  • Residential
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.3055

TO BE BUILT NAUSHON~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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of October 13, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_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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