Oak Bluffs Homes from $1M-$3M

Search with Sandpiper Realty, Inc. to find current luxury homes, between $1M-$3M, for sale in Martha's Vineyard's town of Oak Blufss. Look through a variety of listings to find your new home. Register with us to save your favorite properties, and you can get email updates when new listings match your search criteria.

For more information, questions, or to schedule a showing, contact us today!

You can also search all homes for sale in Oak Bluffs.

61 Bayes Hill Road, Oak Bluffs, MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 22464

  • Residential
  • Square Feet 2745
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1

A must see in Bayes Hill! This spacious two story home on an acre of land with a fantastic backyard is the perfect place to call home. Traditional in style with formal and casual spaces that flow nicely to the multiple gathering areas. The dining room, kitchen and family room span the back of the house and all feature glass doors to the pool area. The outside spaces are amazing - heated gunite pool with pebble tec finish with patio surround and cabana for lounging in the shade. A screened porch offers more outside yet sheltered space, and the expansive decking unifies it all. Four great sized bedrooms occupy the second level including a grand master with walk-in closet and luxuriously appointed bath. A first-floor office/den can also serve as a fifth bedroom. The lower level is nicely finished and offers an additional 700+ square feet of space - perfect for movie watching and gaming. This home has it all - laundry room/mud room, two car garage, attic for storage and more. Bayes Hill is an attractive neighborhood with substantial homes and large parcels providing good privacy; and enjoy association tennis!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

31 Tuckernuck Avenue, Oak Bluffs, MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 34488

  • Residential
  • Square Feet 1738
  • Bedrooms 4
  • Bathroom 1
  • Half Bath 1

A rare opportunity to own a property bordering Waban Park looking out to the ocean beyond. This spacious house with over 1700 square feet of interior space is tied into town sewer. Sit back and relax on the wrap around porch as you gaze over one of the most famous of Oak Bluffs parks an open grassy field and the ocean beyond. The sandy beach is just a block away. The house has been updated with a large kitchen, dining room with built in cabinets, a sun porch and spacious living room that runs the width of the house. Lovingly maintained wood floors and freshly painted walls throughout. Presently there are 4 bedrooms with with an additional second floor sitting room that could be another bathroom or another bedroom. The two front bedrooms have doors that open onto the 2nd floor large porch. Just a short distance to all the shops restaurants and entertainment of downtown Oak Bluffs.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

7 Harbor Lane, Oak Bluffs, MA

Price$1,590,000

Est. Mortgage: $/month

MLS Number 34320

  • 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: 4.94% last updated on Nov 15, 2018
* 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

15 Dover Street, Oak Bluffs, MA

Price$2,295,000

Est. Mortgage: $/month

MLS Number 34382

  • Residential
  • Square Feet 3884
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.37

Sensational water view contemporary design set high on a landscaped hilltop with penetrating views of vineyard haven outer harbor and vineyard sound to the coast of cape cod. This exciting residence, in pristine condition, has amazing sunsets each evening over the outer harbor! Offering 2 master suites, a total of 5 bedrooms and 4 sparkling tiled bathrooms (renovated 2016), spacious open concept ! Features include multiple private balconies, 3 porches, 2 car garage, granite gas fireplace, gourmet kitchen (renovated 2016), central ac, gleaming hardwood flooring, media room, koi pond, mature plantings, and many quality custom details throughout!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

71 Pennacook Avenue, Oak Bluffs, MA

Price$1,149,000

Est. Mortgage: $/month

MLS Number 33425

  • Residential
  • Square Feet 2108
  • Bedrooms 6
  • Bathroom 2
  • Half Bath 1

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 bath home has a lovely eat-in kitchen, formal dining and living rooms with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period details and many updates throughout. Brand new propane hot water and heating system. Full walk-out basement with laundry and plenty of storage space. Home is sunny and warm in the winter and catches the cool summer breezes. GREAT LOCATION just a few blocks to town center, ferry, Ocean Park, and beaches. VERY STRONG RENTAL HISTORY!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

10 Paddock Road, Oak Bluffs, MA

Price$2,320,000

Est. Mortgage: $/month

MLS Number 33638

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day. To be completed in the Fall of 2018. ***** interior pictures shown are of a similar house built by the builder to give you an idea of quality and finishes.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

33 Beach Road, Oak Bluffs, MA

Price$1,500,000

Est. Mortgage: $/month

MLS Number 34185

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

Smell it! Feel it! Taste it...the sea that is! Waterfront 3 season cottage looking westerly over Vineyard Haven Harbor. Sunsets and sailboats everyday plus a DEEPWATER DOCK for all your boating needs. Originally known as "Station #7" of the NY Yacht Club, this historic home was used "back in the day" to give club members a comfortable place to tie up their tenders and step ashore while sailing the waters around the Vineyard. Classic cottage appeal inside and out.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

227 Buddys Drive, Oak Bluffs, MA

Price$1,035,000

Est. Mortgage: $/month

MLS Number 33978

  • Residential
  • Square Feet 2762
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 1

OAK BLUFFS CUSTOM COLONIAL SITUATED on.59 ACRES with an UPDATED & RENOVATED BRIGHT & SUN FILLED GREAT ROOM and an EXPANSIVE living/dining area and NEWER kitchen with STAINLESS STEEL APPLIANCES & GLEAMING GRANITE COUNTERS! The interior of the home is inviting and generous with an abundance of ROOMS! This open design has striking natural wood ship lap ceilings. Glass doors offer access to a huge exterior deck and penetrating views into the abutting State Forest ...The attention to detail includes the luxury of 2 Master Suites, on the first floor and second floor.There is a total of 6 bedrooms, 3. 5 bathrooms and a huge unfinished space above the two bay garage!..STRONG EXISTING RENTAL HISTORY in PLACE! OUTSTANDING LOCATION & TERRIFIC VALUE! ROOM for a POOL TOO! here is a break down of square footage 1st floor sf 1820 2nd floor sf 1280 3rd floor sf 520 Total current finished SF 3620 Above garage unfinished sf 750 Total possibly finished SF 4370 Additional current spaces. Basement sf 1428 Two car Garage sf 550

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

311 East Chop Drive, Oak Bluffs, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

283 East Chop Drive, Oak Bluffs, MA

Price$1,699,000

Est. Mortgage: $/month

MLS Number 33651

  • Residential
  • Square Feet 2456
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Private beach on East Chop with gorgeous water views of the Vineyard Sound from each room, including all bedrooms! Quintessential Vineyard shingled house right on the water; swim, kayak or watch the ferry and boats from your private deck or porch just a few steps to the Sound. 2456 square foot house with four bedrooms (two of them enormous), two and one half baths, large separate laundry room, open floor plan to include fully equipped kitchen, dining room and living room with a large stone fireplace, all with stunning water views. Second floor family room and ample closet space in every bedroom. Enjoy countless hours relaxing on the side deck with outdoor living space in addition to the new stone patio for all your grilling needs. Convenient to both Oak Bluffs, Vineyard Haven and to the Telegraph Hill Lighthouse. Perfectly situated within one mile of East Chop Beach Club, Yacht Club and Tennis Club. Great rental history too. This home will not disappoint.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

117 Barnes Road, Oak Bluffs, MA

Price$1,200,000

Est. Mortgage: $/month

MLS Number 33648

  • Residential
  • Square Feet 560
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.2099

Moved to the current site in 1916 this charming cottage offers expansive views of the Lagoon and outer harbor. Known as "The Outlook" the views extend past West Chop to the Cape. A wraparound porch provides the perfect spot for relaxing, either with a good book or an al fresco meal. Grab a front row seat and enjoy the spectacular sunsets. The comfortable living/dining room, kitchen and two bedrooms and bath, plus outdoor shower, provide a carefree get away. Walk down the path to the 100+ feet of beach. Pull up your kayak or moor your boat. This is summer living at its best.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

32 Harthaven Road (formerly 72), Oak Bluffs, MA

MLS Number 19565

  • Residential
  • Square Feet 2990
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

Harthaven Gem. Beautiful Colonial-style home is located in desirable Harthaven and has access to association beaches, private small boat harbor, tennis and more. This lovely home features 4 bedrooms with private baths and walk-in closets. Enjoy your evenings on the spacious, screened-in porch overlooking acres of conservation land. There is a spacious living room with sliders to the porch. Kitchen has granite counters and ample storage. It opens to the dining area and porch perfect for entertaining. Office/family room in lower level. Home has many special features including central air conditioning, ceiling fans, alarm, irrigation and more. Two-car attached garage. Property abuts Tradewinds, a 71 acre land bank property. Very successfully rental history. Home is being sold turn-key.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

20 Bayes Hill Road, Oak Bluffs, MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 33198

  • Residential
  • Square Feet 2401
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Bayes Hill Charmer...Three bedroom three and a half bath home surrounded by lovely perennial gardens with a wonderful open porch on the front and large private deck across the back of the home.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

28 Beach Road, Oak Bluffs, MA

Price$1,595,000

Est. Mortgage: $/month

MLS Number 32752

  • Residential
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound and beyond to Woods Holes as well as a straight shot down the Lagoon, but this home was also created to be a comfortable home for year-round and summer living. Newly built 4 bedroom/2.5 bath home has commanding views from almost EVERY room with 2-levels of covered decks on the Vineyard Sound side of the home and 2-levels of decks on the Lagoon side. First level features 3 bedrooms, spacious family room, a full bath with laundry and ample storage. The second level features a sun-drenched open floor plan with a gourmet kitchen with stainless Thermador appliances, Silestone counters and an abundance of cabinets. Take in the long view down the Lagoon from the living area with gas fireplace and custom mantel. The master en suite has high ceilings with bathroom features that include a double-sink vanity with marble counters and glass shower enclosure finish this level of the home. There are sliding doors on both levels that open to the front and side decks. High-efficiency heat pump system, central air and more. Home is ready for you to pack your bags and move in. Did we mention the views? Come tour this unique home and see them for yourself. Home is being sold furnished.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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