Oak Bluffs Homes for Sale

Oak Bluffs has a wonderful array of single family homes on Martha’s Vineyard. From beach cottages and waterfront homes to homes within walking distance to downtown, shops, and restaurants, you’re sure to find the perfect Martha’s Vineyard home in Oak Bluffs. Scroll down to explore Oak Bluffs houses for sale on Martha’s Vineyard. Learn about the town of Oak Bluffs >>

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9 Brunswick Avenue Oak Bluffs MA 02557

Oak Bluffs, MA9 Brunswick Avenue

Price$1,299,000

Est. Mortgage: $/month

MLS Number 39572

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.08

Built in 1862, this original MVCMA cottage was relocated from the Vineyard Highlands area to its current site in 1907. Affectionately referred to as “Talawa”, a Jamaican phrase meaning “small but stalwart” after surviving 6 major hurricanes, this cottage is full of history, charm, and original architecture. The interior features bold pops of color, painted pine floors, a modest kitchen, full bath and two bedrooms on the second floor. An Oak Bluffs Historical Survey was conducted on the structure in 1978 in which typical Campground cottage features were identified such as gothic doors, windows made with Sandwich, MA glass, gingerbread bargeboards, and front and side gables. Updates along the way include a 5-year-old roof, new composite porches, railings and decking 3 years ago, and a total re-wire of the cottage to code. Expansion possibilities with a variance. It is the buyer’s responsibility to upgrade the current cesspool to a Title V system. The cottage is not only being offered turnkey, less a few personal items, but also includes a two-week timeshare at The Harborside Inn, Edgartown. These highly desirable, and rarely available for sale weeks are the first week of August in Unit - Interval 410-31, and the third week of September in Unit - Interval 515-37. Enjoy the benefit of extra space for visiting friends and family, or let the hotel do the work and rent the unit to collect revenue.

Listed by Cheri Mason of Landvest MV

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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67 Madison Avenue Oak Bluffs MA 02557

Oak Bluffs, MA67 Madison Avenue

Price$2,200,000

Est. Mortgage: $/month

MLS Number 39587

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.65

Rare East Chop Opportunity – Nestled on the corner of Madison and Green Avenues is a vintage two-story summer home with all the charm of a by-gone era. A superb location, only one block from the East Chop Tennis Club, two blocks from the East Chop Lighthouse and gorgeous bluff views. Ownership of this address provides East Chop Membership access. Explore the opportunities that exist; the large acreage allows room for additional building and expansion. The central hub of the home is the dining room, flanked by a living room with fireplace on one side and a cozy den with bath on the other. The kitchen is conveniently located off the dining room and has access to the backyard and outdoor shower. Four bedrooms and a shared bath are on the second level and feature vaulted ceilings with exposed rafters. The screened porch and stone patio are the perfect places to enjoy the tranquil and private setting. East Chop is a quintessential, close-knit community only a short distance from the harbor and downtown Oak Bluffs.

Listed by Lesley Heidt of Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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34 Windemere Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Windemere Road

Price$3,200,000

Est. Mortgage: $/month

Open House

MLS Number 39595

  • Residential
  • Next Open House: Sat 05/28 3:00 pm. to 6:00 pm.
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3

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 sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has instore for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2022 to be transferred to Buyer at closing.

Listed by JoJo Lambert of Island Home Realty Inc.

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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 West Clinton Avenue Oak Bluffs MA 02557

MLS Number 39344

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 1.5

This spacious antique cottage boasts a wonderful setting abutting MVCMA park grounds to the south and Oak Park to the east plus ample on-site parking and a convenient access road nearby. The front section offers a unique mansard/gambrel roofline that allows for unusual ceiling height on both the first second floors. Vintage double doors, wood floors, two staircases, storage closets and large windows add to the charm of yesteryear. Generous first floor rooms flow front to back with a double parlor, dining room, kitchen and bathroom/storage/utility room. The second floor has five bedrooms and a large ½ bathroom. This is an appealing package for those who value antique homes, a fabulous seaside location in the heart of Oak Bluffs and the MVCMA community preserved lifestyle amenities. Handy attached shed for beach chairs, bikes and garden tools. Minutes to the Oak Bluffs harbor, ferries, village amenities and island beaches. Serviced by town water and town sewer with the betterment balance paid off in full. Come see how sweet life can be in this beloved setting!

Listed by Helena Kirschenbaum of Compass | MV Team

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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77 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA77 Pennacook Avenue

Price$1,595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 39496

  • Residential
  • Bedrooms 5
  • Bathroom 1.5
  • Acreage 0.11

A rare opportunity to own this quintessential Victorian home in the heart of downtown Oak Bluffs. Find yourself within walking distance to Inkwell Beach, shopping, restaurants, ferries, tennis, basketball, parks and more. This lovely property has been meticulously maintained both inside and out and comes with a strong rental history. The land fronts both Pennacook and Massasoit Avenues with a large garage beyond the back yard.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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 Sunset Road Oak Bluffs MA 02557

Oak Bluffs, MA33 Sunset Road

Price$1,290,000

Est. Mortgage: $/month

Active With Contract

MLS Number 39533

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2304

This is a great opportunity to be your next family home, investment rental property, or even workforce housing. It works for everyone! This home has been loved and lived in by the same owners for the past 18.5 years. Close enough to downtown Oak Bluffs for an easy walk, but yet far enough away to have some privacy on this quiet dead-end residential street. The partially finished basement with a full bathroom adds extra space to the already large and open home. In 2018 there were many upgrades including a new roof, all new kitchen appliances, a new propane furnace, & a new electric hot water tank! SELLER to replace at their cost the septic system leaching field. Property is a legally permitted 3-bedroom home. Public record is incorrect.

Listed by David Holmberg of HomeSmart Heritage Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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 Oak Avenue Oak Bluffs MA 02557

Oak Bluffs, MA25 Oak Avenue

Price$729,000

Est. Mortgage: $/month

MLS Number 39551

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 0.5
  • Acreage 0.2318

One of just three buildable lots in Oak Bluffs, this nearly quarter-acre property is close to the town of Oak Bluffs and its shops, restaurants, attractions and ferry dock. (Go down Simpson Avenue and it's a straight shot to Sunset Lake and town.) Oak Avenue is a quiet, dead-end street with little traffic. There are few trees on this level lot which can support up to five bedrooms. An enhanced septic system is not required, which will save thousands. The home has not been used for a while and should be considered a tear-down. The garage, which should also be replaced, is non-conforming, but the footprint can serve as the starting point for a new structure. Located in a neighborhood of nice homes, this attractive parcel offers much potential for your new Vineyard home and much-in-demand, close-to-Oak-Bluffs rental opportunities. Being offered "As Is."

Listed by David Lott of Vineyard Open House Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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8 Siloam Avenue Oak Bluffs MA 02557

Oak Bluffs, MA8 Siloam Avenue

Price$649,000

Est. Mortgage: $/month

MLS Number 39519

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

SEA SIDE COTTAGE CHARMER - You've found a heavenly setting for endless summers and nightly sunsets! Directly across from famed Sunset Lake and steps to the Oak Bluffs harbor, ferries, village amenities and minutes to island beaches. WATER VIEWS await you - just pull up a rocker on the ample porch or enjoy the balcony above. Neat, tidy plus loaded with charm and vintage details. First floor bedroom, washer/dryer and the sunny eat-in kitchen has high ceilings and a bank of south facing windows. This summer season cottage enjoys a propane rinnai heater to take the chill off of spring and fall days. The newly created Sunset Lake betterment walkway adds a useful and delightful visual directly across the street. Life by the sea is sweet as can be!

Listed by Helena Kirschenbaum of Compass | MV Team

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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 Buena Vista Street Oak Bluffs MA 02557

Oak Bluffs, MA47 Buena Vista Street

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 39545

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.3317

Gracious 2 story home located at the end of quiet street. Well maintained, this one owner home has an open floor plan with cozy gas free standing stove in the living room, a large main level bedroom with private bath and 2 bedrooms (one ensuite) upstairs, a hallway bath and an office. The full basement has heat so can easily be finished into a playroom/REC room. Outside is a 12x10 storage shed, a private back yard with room for a pool, garden or garage. Outdoor shower and irrigation in the yard too! Lot runs from Buena Vista to Menahan St., so "possible" to build a garage or guest house(after 5 years) off Menahan St. Buyer to verify. Close to town, East Chop and Eastville Beach. Closing late June/early July works for seller...so be in for the summer 2022!

Listed by Doug Reece of On-Island Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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26 Greenleaf Avenue Oak Bluffs MA 02557

Oak Bluffs, MA26 Greenleaf Avenue

Price$3,800,000

Est. Mortgage: $/month

Open House

MLS Number 39529

  • Residential
  • Next Open House: Sat 05/28 4:00 pm. to 6:00 pm.
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 3.5

How often do you find a property with three different water views -pond (Sunset Lake), harbor (Oak Bluffs) and ocean (Vineyard Sound). Location is everything, and this bungalow has it all. You can practically hear the children squeal with joy after catching the brass ring at the famous Flying Horses Carousel, and a front row seat on your wrap-around porch for the annual August fireworks. As close as it is to the ferry, beaches, restaurants, shops, and even the public library, this getaway perched on a hill in a quiet neighborhood allows for a peaceful cup of morning coffee on the side patio. Thoughtfully renovated by a popular local architect, this bright and cheery cottage provides plenty of room for multiple guests. Each of the unique 6 bedrooms makes clever use of space and natural light. When you think of a seaside getaway with all the amenities, this is what you picture. And if you want to share, there is a strong rental history.

Listed by Carol McManus of C McManus Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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54 Cannahoot Street Oak Bluffs MA 02557

Oak Bluffs, MA54 Cannahoot Street

Price$1,375,000

Est. Mortgage: $/month

Pending

MLS Number 39391

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.229

Located on East Chop, in pristine condition and just a short walk to the beaches, tennis courts, yacht club/harbor, downtown restaurants and the ferries, is this contemporary/modern style 2-bedroom main house, being sold furnished plus detached 1-bedroom/1-bathroom detached bedroom. The main house’ modern design features radiant floor heating, cathedral ceilings, modern kitchen, a central concrete block wall behind the floor to ceiling wood burning Rais-Wittus Shaker bench woodstove and access to exterior decks from both the main entrance and the bedroom. The steel staircase to the second floor is showcased by a wall of light from the hallway. The second floor features an ensuite master bedroom that has its own balcony deck with outdoor shower. It is located on 10,000 sq. ft. (0.23 acres), that includes a front and side yard and has parking for 2-3 vehicles.

Listed by Perry Patterson of MV Luxury Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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5 Tabernacle Avenue Oak Bluffs MA 02557

Oak Bluffs, MA5 Tabernacle Avenue

Price$889,000

Est. Mortgage: $/month

Open House

MLS Number 39500

  • Residential
  • Next Open House: Sat 05/28 3:00 pm. to 5:00 pm.
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 1

5 Bedroom Beautiful Victorian located in the Historic Martha's Vineyard Camp Meeting Association on popular Tabernacle Way! RARE OFFERING with Victorian Charm and Attractive Vintage Detail on a generous fenced-in lot with BEAUTIFUL COLORFUL GARDENS! Terrific IN-TOWN LOCATION...easy stroll to Oak Bluffs Harbor, Beaches, Ferries, Galleries and Restaurants! From the sweeping wrap-around porch there are active post card views of Trinity Park and the historic Tabernacle where all the weekly services and events take place. The interior living space includes over 1536 sq feet with high ceilings, striking wood floors a welcoming dining room, an ample eat-in kitchen and a bright/airy generous parlor/ living room. Second floor features 5 comfortable bedrooms and 1 bathroom. A BONUS WALK-UP ATTIC SPACE offers MANY OPTIONS for possible expanded use! This Cottage has been enjoyed by this family for over 40 years! Exceptional offering with the perfect flow for both Summer living and entertainment. Savor the summer concerts from the comfort of your own porch! For more information on the Martha's Vineyard Camp-Meeting Association please visit www.mvcma.org .

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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"Based on information submitted to MA_LINKMV as of May 24, 2022 . 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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