Oak Bluffs Homes For Sale

Oak Bluffs, MA, is Martha Vineyard’s original summer resort, dating back to the late Victorian era. Oak Bluffs real estate includes a wide range of homes including quaint capes, charming bungalows, and waterfront estates. You’ll also find homes in Oak Bluffs with the hallmark colorful "gingerbread" aesthetic and views of the ocean. Oak Bluffs residents revel in the lively scene of Circuit Avenue and the harbor front, day and night, while the outlying neighborhoods contrast in serenity. Find some of the most in-demand Martha’s Vineyard real estate including luxurious waterfront houses and vacation condos in Oak Bluffs. Learn more about Oak Bluffs.

Contact us online or call 508-693-6866 for more information or to visit any of the Martha's Vineyard properties in Oak Bluffs below. We will help you find the right vacation home or year round residence!

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52 Head of the Pond Road

MLS ID 34050

  • Residential
  • Square Feet 3100
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 1

This contemporary 5 bedroom home is located in a nice area of fine homes and close to farm fields and conservation walking trails. The open floor plan includes a newly renovated kitchen, spacious living ,dining room with sliders to a screened-in porch and deck. First floor master bedroom and bath. The second floor includes 2 bedrooms, an office and great room with cathedral ceiling and skylights. An efficiency apartment can be accessed from the main house as well as it's own entry. The third floor has been finished for additional studio space with skylights. 2-car garage and an attached office space for an in-home business. A great value in this market.

Listed by Karen M. Overtoom R.E.

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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225 East Chop Drive

Price$3,950,000

Est. Mortgage: $/month

MLS ID 33942

  • Residential
  • Square Feet 2449
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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311 East Chop Drive

Price$2,250,000

Est. Mortgage: $/month

MLS ID 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathrooms 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

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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 Nahomon Street

Price$710,000

Est. Mortgage: $/month

MLS ID 33679

  • Residential
  • Square Feet 1131
  • Bedrooms 2
  • Bathrooms 2
  • Acreage 0.1199

Don't miss this opportunity to own the perfect Oak Bluffs get-away with a pool. Every inch of this Cape-style home has been well cared for. The home features brazilian cherry floors, updated kitchen with stainless appliances, spacious living room with brick fireplace, first floor bedroom and tile bath. Second floor offers a bedroom suite with jacuzzi tub and tile shower. Enjoy lush gardens, large farmers porch, outdoor deck plus a second grilling area all overlooking an in-ground pool. Just a short distance to Oak Bluffs center and Harbor. Excellent rental history!!

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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32 Iron Hill Road

Price$829,000

Est. Mortgage: $/month

MLS ID 33283

  • Residential
  • Square Feet 1534
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 1.517

A must see hidden gem this home lies on 1.52 acres featuring over 100k of reclaimed antique stone work. Located in a very private setting down island, 10 minutes from ferry and 15 minutes from beaches, this home has the feel and tranquility of being up island. The main house offers 3 bedrooms 2 baths with an airy and open floor plan. Beautiful reclaimed wide antique oak flooring as well as other artistic touches truly gives this home the authentic feel of Marhtas Vineyard. An attatched 1400 sq ft 2 story addition with beautiful large stain glass windows ( 4x6ft ) is ready to be easily finished and offers an opportunity to almost double the homes square footage at 2900 sq ft. In addition to added living space it would also make a great home office or artist studio.The property setting is on high ground and overlooks a 9 acre pasture with rights to graze two horses. Access to Little Duarts Pond also accompanies ownership. This property is a great opportunity as a rental/investment home with the additional opportunity to add substantial value with finished addition. Difficult to capture this home in pictures, truly a must see !! And ,YES !, the clock works and keeps perfect time. It is fully modernized with a gps unit for accuracy.

Listed by Jane Brown Assoc.

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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20 Bayes Hill Road

Price$925,000

Est. Mortgage: $/month

MLS ID 33198

  • Residential
  • Square Feet 2401
  • Bedrooms 3
  • Bathrooms 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

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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76 Trinity Park

Price$499,000

Est. Mortgage: $/month

MLS ID 32837

  • Residential
  • Square Feet 640
  • Bedrooms 2
  • Bathrooms 1

Oak Bluffs in the VILLAGE! Located on Trinity Park~ is this CHARMING Year Round Campground Cottage in HISTORIC MARTHA'S VINEYARD CAMP MEETING ASSOCIATION. Open spacious living area with high painted ceilings, 2 bedrooms one bedroom area is " loft style" with wood floors! Enjoy all the wonderful tabernacle events front your porch overlooking large lawn on Trinity Park and The Tabernacle. Onsite parking outside the back door. Oil forced hot water and a newer hot water heater, cottage is fully insulated. Only a short walk to Circuit Avenue, beaches and ferry ports! VACANT EASY TO SHOW!!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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32 Temahigan Avenue

Price$4,350,000

Est. Mortgage: $/month

MLS ID 32756

  • Residential
  • Square Feet 6441
  • Bedrooms 6
  • Bathrooms 5
  • Half Bath 2

HISTORIC EAST CHOP WATERFRONT ESTATE WITH BOATHOUSE AND DEEP WATER DOCK. Originally built in 1870 with all of the grandeur of a 19th century seaside estate, this grand historic home features over 6,000 square feet of finished interior living space which was meticulously renovated from top to bottom in the year 2000, under the direction of noted architect, Joseph Dick and island builder, Everett Whorton. Today, this luxurious home maintains all of the original character and architectural details of the era, including beautiful coffered ceilings, gorgeous custom wood paneling, and finely crafted millwork throughout. The property boasts sweeping views from three floors of living space -- plus a spacious outdoor deck -- across the 3.2-acre property with rolling lawn, patio with stone fireplace and beautifully landscaped grounds to Vineyard Haven Harbor and Vineyard Sound beyond. A wooden boardwalk crosses over a small pond, leading to the water's edge where a 750-sf boathouse with stone fireplace, kitchen and bath sits adjacent to a deep water dock and moorings. The property also includes a detached 2-car garage with unfinished living space above which can be easily transformed into a beautiful Guest House, also with water views. This iconic property is the ultimate place to gather family and friends and create treasured Vineyard memories for years to come. Furnishings are available separately.

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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 Beach Road

Price$1,595,000

Est. Mortgage: $/month

MLS ID 32752

  • Residential
  • Square Feet 1800
  • Bedrooms 4
  • Bathrooms 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, HOT TUB 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. Rentals in place for the Summer of 2019. Purchase the home and get the rental income at the closing! Home is solar-ready.

Listed by Island Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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10 Elliott Avenue

Price$499,000

Est. Mortgage: $/month

MLS ID 32661

  • Residential
  • Square Feet 996
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.1

Charming two bedroom Cape style ranch property located on a dead end street within close proximity to downtown Oak Bluffs, public transportation, beaches, and East Chop tennis courts. Upon entry, you are welcomed into the sunlit living room with fireplace, kitchen with lots of cabinet and counter space includes small dining area. Front deck running the length of the house and and grassy yard are the perfect compliments to this move in ready, year-round home. New Title V septic for 2-bedroom house installed April 2018. Easy to show.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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