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

MLS Number 35291

  • MultiFamily
  • Mls Status Active
  • 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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Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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89 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA89 East Chop Drive

Price$3,395,000

Est. Mortgage: $/month

MLS Number 37747

  • Residential
  • Mls Status Active
  • Village East Chop
  • Bedrooms 7
  • Bathroom 5.5

This spectacular direct oceanfront residence is located in East Chop an exclusive area of historic Oak Bluffs on Martha's Vineyard. With nearly one acre of land, there are endless opportunities to keep the home as is or build the new home of your dreams. Enjoy spectacular unobstructed and panoramic views of Nantucket Sound. Wake up to amazing sunrises, enjoy the daily "boat show" and watch the sun go down as you roast marshmallows on your own private beach area. An easy stroll takes you to the harbor, town, great restaurants, shops, and an abundance of other activities that make East Chop a very special place for the whole family to enjoy. In the market for more space for your home-based business or work from office - the finished lower level provides ocean views as well as its own entrance giving you the best of both worlds! This unbelievable setting must be seen to be appreciated. Don't miss out on the opportunity to acquire this generational asset! For those looking for an investment property, this beautiful home also has a great rental history. Video Tour: https://youtu.be/Qjn-BOGKzRk

Listed by Gayle Kiley of New England Property Shoppe

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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$1,995,000

Est. Mortgage: $/month

MLS Number 37706

  • Residential
  • Mls Status Active
  • 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: 2.97% last updated on Feb 25, 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

MLS Number 37052

  • Residential
  • Mls Status Active
  • 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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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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246 Newton Avenue Oak Bluffs MA 02557

Oak Bluffs, MA246 Newton Avenue

Price$1,750,000

Est. Mortgage: $/month

Pending

MLS Number 36905

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 4
  • Bathroom 2

Four bedroom family home OVERLOOKING and FRONTING Lagoon Pond. Commanding views up and down the Pond, across to VH harbor, Vineyard Sound & beyond to Falmouth. A picture perfect setting with active views and outstanding sunsets. Plus your own DEEPWATER DOCK, extending 115ft for boating and swimming pleasure. The first floor of this residence has a dining area, galley kitchen, 2 bedrooms, bath & utility room. 2nd floor has two add'l bedrooms, bath, entry den & large, open living room with sliders to a spacious deck. The grounds and embankment are lush green providing privacy yet yielding to the vast view. 2 car garage to rear with lots of storage space. This homes comes mostly furnished.

Listed by Robert Murphy of Towne & Country Realty

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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

MLS Number 35358

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

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: 2.97% last updated on Feb 25, 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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10 Pequot Avenue Oak Bluffs MA 02557

Oak Bluffs, MA10 Pequot Avenue

Price$1,550,000

Est. Mortgage: $/month

Active With Contract

MLS Number 37781

  • Residential
  • Village Downtown
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.06

Beautifully restored Vintage Victorian year-round home located less than a block to the Inkwell Beach and walk to town. Views of Nantucket Sound from the wrap-around front porch and the second floor master balcony. The exquisitely detailed front porch is made of solid mahogany with hand-turned mahogany posts. This home was taken down to the studs 5 years ago and finished to perfection. This home offers 4 bedrooms, 2.5 baths, a bright kitchen with granite counters and stainless steel appliances a large living room, dining room, full bath, laundry room, and first floor bedroom. The second floor contains 3 additional bedrooms and one full bathroom with access via two separate staircases, one via the living room and one via the dining room. There is a bonus living area attached to the rear of the home with a small living area and 1/2 bath...ideal for an in-law suite. Solid rental history of $50k per season with potential for more. Fully insulated with air conditioning and heating, along with a cozy gas fireplace makes this home perfect for year-round living. There is also a rear deck and enclosed outdoor shower. An in-town gem with some furnishings included, makes it virtually turn-key.

Listed by Cathy Gargiulo of Ocean Park Realty Inc

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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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

MLS Number 36072

  • Residential
  • Mls Status Active
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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55 Worcester Avenue Oak Bluffs MA 02557

Oak Bluffs, MA55 Worcester Avenue

Price$1,389,000

Est. Mortgage: $/month

Pending

MLS Number 35514

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 3
  • Bathroom 3.5

NEW CONSTRUCTION - WALK TO WATER - Custom Three Bedroom, Three and a Half Bath Home with extensive interior trim including wainscoting, coffered ceilings and rustic beams. This house has a significant amount of features not typically found in this price range! The entire ground floor is L-Shaped with two living areas on opposite sides of the house, the kitchen being the central point. The main Living Room has a Coffered Ceiling, Hardwood floors, direct access to a huge mahogany deck and a propane Fireplace. The Custom Kitchen has Quartz counters, Stainless Steel Appliances and Rustic Beams. Two dining areas, one formal, one informal, provide a transition into each of the living areas. (See Floor Plans in Photos). Second Living Area/Den with built-in bookcases. Shiplap clad entrance hallway with half bath. Wainscoting throughout the main living level. Upstairs, a dramatic, two story landing, with coffered ceiling and shiplapped feature wall overlooks the entrance hallway. There are Two Bedrooms with Ensuite - each have their own private bathrooms and private balconies. A loft, third living area upstairs which leads to a Third bedroom, both of which share the full guest bathroom. Custom tile work throughout. Full size windows in full basement and exterior access to back yard and outdoor shower. Forced Hot Air heat and Central Air-Conditioning. Huge mahogany Deck 12ft x 30ft. Two Car Garage with custom doors and off street parking. A short walk to the end of the road and you'll be at the Beach on the Lagoon - Great for swimming and boating - a Big Plus for renters! Minutes to bike or to drive to downtown Oak Bluffs and Ferry. Easy to Show! (Taxes only reflect land assessment.) PRICE INCLUDES A FINISHED BASEMENT and Cool Firepit with hardscape.

Listed by Alisan Lohan-Conway of Alisan Lohan-Conway Properties

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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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29 Bayes Hill Road Oak Bluffs MA 02557

Oak Bluffs, MA29 Bayes Hill Road

Price$1,349,000

Est. Mortgage: $/month

Pending

MLS Number 37440

  • Residential
  • Mls Status Pending
  • Village Lagoon/Harbor
  • Bedrooms 4
  • Bathroom 4

Extraordinary attention to detail! This spacious and open Contemporary home in the desirable Bayes Hill community is move-in ready, offering a unique blend of multiple gathering spaces and privacy. Continuously renovated, the home is in "cherry" condition---cherry wood floors and railings throughout all three levels; cherry cabinetry in the custom kitchen and all baths; and cherry bookcases in the finished lower level library/den. But the heart of this home is the intelligently designed gourmet kitchen with its quartzite counters, French porcelain tile backsplash, custom cherry cabinets, specialty lighting and quality stainless steel appliances including a commercial grade SubZero refrigerator/freezer, Wolf propane cooktop and double ovens, warming drawer, Bosch dishwasher, built-in microwave and even a built-in coffee maker! The essentials, plus some, are new------all new mechanicals including propane furnace, HVAC, geo/thermal hot water heater, roof, floors, windows, skylights, doors, bathrooms, lighting, ceiling fans etc. Too many details to mention. A must see!

Listed by Lynn Buder of Sandpiper Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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

Active With Contract

MLS Number 36968

  • Residential
  • Village Lagoon/Harbor
  • Bedrooms 5
  • Bathroom 3
  • Acreage 2.4786

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: 2.97% last updated on Feb 25, 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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309 County Road Oak Bluffs MA 02557

Oak Bluffs, MA309 County Road

Price$1,289,000

Est. Mortgage: $/month

MLS Number 37448

  • Residential
  • Mls Status Active
  • Village Central
  • Bedrooms 4
  • Bathroom 6

The Opportunity You Have Been Waiting For! This conveniently located four-bedroom home is situated on a double size lot and offers space for everyone. The primary dwelling is four bedrooms and four full bathrooms. To the left of the foyer, there is a bedroom with a completely renovated luxurious bathroom. To the right of the foyer, there is a family room, wet bar, bedroom, full bathroom, and a private deck. Upstairs one will find an expansive family / living room, oversized bedroom, full bathroom, and kitchen. A large deck provides privacy and plenty of room for outdoor dining / lounging. The lower level offers additional living space, a large bedroom, a full bathroom, and a wet bar. The detached garage offers an oversized three-bay garage + office space above. There is a coin-operated laundry room, shed for additional storage, and plenty of parking. This property generated $142.8K of rental income in 2020.

Listed by Jarrett Hurwitz of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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 February 28, 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."