Oak Bluffs Homes for Sale

If you are looking to purchase a home the town of Oak Bluffs, Breakwater is here to assist you along the way. You will find listings in the famous Martha's Vineyard Camp Grounds "Gingerbread cottages",  along Ocean Park, or on East Chop as well as other areas within the Village.  Purchasing a home in this classic beach town can range from a small summer cottage to a luxury waterfront home.   

Find Homes For Sale in Oak Bluffs

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348 Sea View Avenue Oak Bluffs MA 02557

Oak Bluffs, MA348 Sea View Avenue

Price$5,995,000

Est. Mortgage: $/month

Pending

MLS Number 35291

  • MultiFamily
  • Mls Status Pending
  • Village State Beach
  • Bedrooms 13
  • Bathroom 6.5

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - Perched high on a bluff with 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Wood-burning fireplace. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage with additional space above, bath and outdoor shower, there is lots of possibilities to to be creative. The garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option. Please view Video of the Property to get a full feel for this one of a kind waterfront property.

Listed by Michele Moore of Island Real Estate

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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9 Crescent Road Oak Bluffs MA 02557

Oak Bluffs, MA9 Crescent Road

Price$3,650,000

Est. Mortgage: $/month

Pending

MLS Number 37888

  • Residential
  • Mls Status Pending
  • Village East Chop
  • Bedrooms 3
  • Bathroom 3

EAST CHOP: Dramatic WATER VIEW property features a refined open design with meticulous attention to detail integrating the highest quality materials that makes this offering soundly stand out from other fine homes in this price range. The exquisite landscaping surrounding the residence is an established arboretum of exotic trees, plantings, and stone work highlighted by a crystal clear Koi pond with a soothing waterfall. The interior, both comfortable and visual, flows from one intimate setting to another offering dreamy views of NANTUCKET SOUND complemented by the artistic combination of colors, materials and textures...gleaming Birch flooring throughout, imported marble accents in bathrooms and kitchen, Venetian Plaster ceilings and walls with inset railings in the stairways, broad commercial grade Fleetwood windows, Lutron lighting system, Viking and Sub Zero Appliances, the finest contemporary finishes and fixtures...SO MUCH MORE TO EXPERIENCE....Situated in a protective setting on the Bluffs of East Chop...an easy walk to Beaches, Harbor and Town Center.

Listed by Amy Goldson 202-251-2922 of Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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90 Dukes County Avenue Oak Bluffs MA 02557

Oak Bluffs, MA90 Dukes County Avenue

Price$2,195,000

Est. Mortgage: $/month

Pending

MLS Number 37831

  • MultiFamily
  • Mls Status Pending
  • Village Downtown
  • Bedrooms 5
  • Bathroom 5.5

Downtown Oak Bluffs – Entrepreneurs, savvy business owners, investors or those simply seeking downtown living, this property is a must-see to understand the opportunities it presents. Located in the Art’s District, this collection of boutique residences offers upscale and stylish interiors with hand-selected designer finishes. Carefully spaced to ensure privacy, each oasis is extended by intimate courtyards for open air dining or relaxation. The compound includes a highly-visible commercial/office space and plenty of parking for residents or customers. This dynamic embraces the work from home trend and is an income-producing opportunity. Zoned in B1 where flexibility exists to cater to alternative uses. Pedestrian-friendly where a stroll or bike ride will take you to the picturesque harbor, sandy beaches, shopping and eclectic eateries - all the best of Oak Bluffs is steps away.

Listed by Lesley Heidt of Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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3 Pond View Drive Oak Bluffs MA 02557

Oak Bluffs, MA3 Pond View Drive

Price$1,950,000

Est. Mortgage: $/month

Pending

MLS Number 37052

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 3
  • Bathroom 3

3 Pond View has a striking modern 3600 sq.ft home & 750 sq. ft. studio nestled in a private setting abutting a greenbelt of conservation land. The house and studio were designed by Vineyard architect, Bruce MacNelly. It is spacious with high ceilings, white oak floors, an open floor plan which enhances all of its light-filled spaces. The large high windows frame the outdoors, providing visual interest all year long. It is the perfect spot for entertaining and features large walls for exhibiting artwork. The main level offers a large dining room, galley kitchen, living room, large master bedroom, 1.5 baths, laundry & ample closets. Outside the kitchen, there is a bluestone terrace perfect for outdoor dining and entertaining. On the ground floor, there are two walk-out bedrooms, a bath, a large family room & two workrooms that open to a rice stone patio and gardens. The separate spacious studio is ideal for an artist, writer or anyone working remotely. The property has deeded access to 25 feet of beach on Lagoon Pond, a short walk from the residence. Owner's abutting parcel of land is available to purchase by the buyer.

Listed by Kathryn Tate of Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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220 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA220 East Chop Drive

Price$1,895,000

Est. Mortgage: $/month

Pending

MLS Number 37706

  • Residential
  • Mls Status Pending
  • Village East Chop
  • Bedrooms 4
  • Bathroom 2.5

Prime home in desirable East Chop diagonally across from one of the Vineyard's most photogenic lighthouses, the East Chop Light. With dramatic views from this uniquely designed 4-bedroom, 2 ½ bathroom, year-round or vacation house, this property should be at the top of your list if you're looking for water views, sunsets over West Chop, and close proximity to beaches, tennis courts, the Oak Bluffs harbor and downtown areas. The home -- known locally as "Pilot House", was built true to its name to replicate the bridge of a ship's Pilot House to allow the Captain views of a wide sweep of the sea. Wrap around decks off the second floor provide panoramic water views, in addition to the roof-top Widow's Walk which boasts 180-degree water views of Nantucket and Vineyard Sounds. Built to take advantage of the views, the second floor’s open floor plan has walls of large windows in the living room, dining room and kitchen which provide ample water views, sunsets to the west, sunrises to the east and night-time starry evening viewing. A master bedroom and full bath complete the floor. First floor includes 3 bedrooms, and 1 ½ bathrooms, in addition to access to the basement storage areas and garage. Property includes outdoor shower, and parking for several cars on each side of the house. Title V septic certified 12/19/2020. Deck is in need of repairs/replacement and is the buyer's responsibility, as it can either be repaired or redesigned to suit the buyer's taste. The house is being sold fully furnished. The lot is large enough to allow for expansion of the house but please confirm any plans with appropriate town offices.

Listed by Perry Patterson of RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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21 Tower Ridge Road Oak Bluffs MA 02557

Oak Bluffs, MA21 Tower Ridge Road

Price$1,725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 35358

  • Residential
  • Village Central
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.78

Located in the highly desirable Tower Ridge neighborhood offering, privacy, tennis, and easy access to Farm Neck Golf Club, the Island bike path and miles of hiking trails. This lovingly maintained home has undergone many sensible upgrades and recent renovations including, new windows, renovated gourmet kitchen, copper gutters, red cedar siding, 2-sided granite fireplace, renovated tile baths, sun-room, sauna, fireplace in master bedroom, cathedral ceilings, finished basement, and plenty of outdoor space, are among the many features this home offers. A detached 2-car garage with 15ft ceilings is perfect for boat storage. Above the garage is a spacious studio with cathedral ceilings and private second floor deck. A picture-perfect garden shed was fully renovated and features a covered porch, wood detail throughout, loft storage space, updated windows and is set up for year-round use. This is an incredible investment opportunity not to be missed!

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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312 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA312 East Chop Drive

Price$1,695,000

Est. Mortgage: $/month

MLS Number 37959

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2502

"The Doll House" is an iconic home on East Chop Drive with waterfront on Crystal Lake and views of Vineyard Sound. Once a quaint fishing cottage, this home has been carefully renovated and meticulously maintained over the years. With nearly 150 feet of waterfront on Crystal Lake, you can enjoy swimming, kayaking or paddling from your backyard. The main house features a comfortable sunporch, open living room with a stone fireplace, a sun filled master bedroom with waterviews, updated cook's kitchen and dining room both featuring stunning brick floors. French doors in the kitchen open to a spacious yard for outdoor entertaining and a charming "boathouse" that has been converted to a dining area. A modern spiral staircase takes you to an expansive rooftop deck where you can spend the day bathing in the sun and watching the Ferry boats come and go. A delightful guest cottage offers 2 additional guest bedrooms with high ceilings and a full bath. Other amenities include a private outdoor shower and a one-car garage with an attached artist studio. This wonderful location is also an easy bike ride to the East Chop tennis, beach and yacht clubs and to both downtown Oak Bluffs and Vineyard Haven. Truly a magical island home.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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11 Isaac Avenue Oak Bluffs MA 02557

Oak Bluffs, MA11 Isaac Avenue

Price$1,400,000

Est. Mortgage: $/month

MLS Number 38024

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.2513

New Construction Underway in Oak Bluffs! Just a short walk to the Lagoon or a quick bike or drive to downtown, this new home is conveniently located for year round or summer use. The property features an open concept kitchen and dining area with hardwood floors throughout the first floor. The kitchen has quartz countertops and a center island with induction cooktop and range hood. The dining area has access to the mahogany side deck for outdoor entertaining, and to the living room with pocket doors for added privacy. A home office, half bathroom and laundry/mudroom finish off the first floor living space. The second floor includes two guest bedrooms and a shared full bathroom with carrara marble double sink vanity, tile floors and tub/shower tile surround. The Primary Bedroom Suite includes a walk-in closet and private bath with carrara marble double sink vanity, walk-in shower, dual rain and hand held shower heads and tile floors. A functional and thoughtful floor plan with many of the features you're looking for in a home. Estimated completed construction date ~ end of August 2021.

Listed by Terie Geary of Donnelly + Co

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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5 Sages Way Oak Bluffs MA 02557

Oak Bluffs, MA5 Sages Way

Price$1,399,000

Est. Mortgage: $/month

MLS Number 38125

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.7329

Inviting colonial set in the desirable Pond View neighborhood of Oak Bluffs. Plenty of room to spread out in this recently built home that has central heat/ac. With abundant light and beautiful wood floors throughout, the floor plan is casual and open with several areas to entertain both inside and out. Three bedrooms are perched upstairs, including an oversized primary bedroom suite with walk-in closet. Perfect for both year round and summer/seasonal enjoyment, the home also features a full basement with walkout two car garage - amazing for storage. There is also room on the property for a detached bedroom or carriage house with 4 bedroom septic in the ground. Make this property yours today!

Listed by Peyton Wallace of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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111 New York Avenue Oak Bluffs MA 02557

Oak Bluffs, MA111 New York Avenue

Price$1,395,000

Est. Mortgage: $/month

Pending

MLS Number 36072

  • Residential
  • Mls Status Pending
  • Village East Chop
  • Bedrooms 6
  • Bathroom 8

Exceptional and unique opportunity in East Chop -- walking distance to beaches, restaurants, galleries, harbor and ferries! Known for many years as the Martha’s Vineyard Resort/B&B, this 6-bedroom/8-bathroom property with enormous 1st floor great room, 5-ensuite bedrooms upstairs (one with living room and fireplace), and connected property manager's office with 1-bedroom plus loft living quarters, speaks to its use as a rental property within walking distance to everything downtown. The inviting and spacious outdoor entertainment spaces include wrap around front covered porch, rear covered porch running the length of the house, and a 2nd floor balcony deck also running the length of the house. The full finished basement, with bar, and bathrooms, adds another 1,600 sq feet. The private property manager's quarters located off the main floor has an open living-kitchen-office area, bedroom and bathroom on the first floor, and a spiral staircase to the 2nd floor loft bedroom. House comes partially furnished. A great investment/rental property, or transform into your vacation or year-round home. Property has recently received town approval for subdivision of the lot which expands the lot to approximately 17,252 sq ft, or by adding an additional approx. 7,234 sq ft of land (this includes 4,161 sq ft running the length of the driveway side of the lot to rectify the setbacks, and another 3,071 sq ft behind the house to expand the back yard). See subdivision plan in the documents section.

Listed by Perry Patterson of RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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17 Tower Ridge Road Oak Bluffs MA 02575

Oak Bluffs, MA17 Tower Ridge Road

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38046

  • Residential
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.7617

This gorgeous fully renovated cape in Tower Ridge has so much to offer! From the moment one steps in the door of this property, everything feels just right. The home has a beautifully open floor plan, with a central island kitchen with updated appliances and quartz counters. One side of the kitchen leads first to an open dining area, and onward to cozy seating/tv space. There is a primary bedroom suite on the first floor with a beautiful private bathroom. The first level also includes a second sitting room, mud room with laundry and a two car attached garage. Upstairs are two generously sized bedrooms that share the second full bathroom. The full basement is unfinished but excellent for storage. Above the garage is another ~400 sf that may be finished with permitting from the town. Outdoors there are comfortable front and back yards, a back deck and outdoor shower. Overall this is a superb offering that is well-suited for both year-round and seasonal use. The location is convenient to Farm Neck Golf Club and downtown Oak Bluffs, yet still private and quiet on nearly 3/4 of an acre. Furnishings are negotiable.

Listed by Peyton Wallace of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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56 Temahigan Avenue Oak Bluffs MA 02557

Oak Bluffs, MA56 Temahigan Avenue

Price$1,295,000

Est. Mortgage: $/month

Pending

MLS Number 36968

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 5
  • Bathroom 3

Perfect Eastville location, for year-round or vacation living w/distant views to West Chop, Vineyard Sound and Vineyard Haven outer harbor. The property consists of 2.48 acres of elevated land, scenic marshes and woodlands, with numerous wildlife species and lots of privacy. The present raised Ranch style home is sturdy but in need of a major makeover. Remodeling and elevated levels will open up a whole new vista coupled with tree maintenance and brush cutting. Orientation of living and outside activities would be to the rear of the present structure. Property comes with deeded DEEPWATER ACCESS via a co-owned, non-buildable lot, known as #10 (a/k/a #5) Beach Rd. Ext. Deed reference for beach lot is Bk12Page413. This gives the Buyer 50% undivided ownership, steps from their frontage and also offers potential for a dock or mooring access. In place is a NEW title V septic for 6bedrooms.... What an opportunity for creative buyer...

Listed by Robert Murphy of Towne & Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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"Based on information submitted to MA_LINKMV as of May 9, 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."