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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Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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22 Paddock Road Oak Bluffs MA 02557

Oak Bluffs, MA22 Paddock Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 38557

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 1.867

THIS IS THE ONLY LOT AVAILABLE in the PRESERVE at The WOODLANDS! COMING SOON...TO BE BUILT...by SHAWN CHAPPS...UNDER EARLY STAGES OF DESIGN and STILL TIME to CUSTOMIZE with YOUR OWN PERSONAL TOUCHES! Sophisticated Sprawling Contemporary Barn Style Residence with Clean Classic Lines, Natural Timber Beams, Field Stone Fireplace and Soaring Ceilings. This Spacious Airy Open Floor Plan will have no shortage of living areas with multiple intimate gathering spaces surrounded by lots of glass that ddisplays an unobstructed panorama of the lush landscaped backyard and 20x 40 Gunite Pool and Spa. The Decked Out Chefs Kitchen will be a fusion of modern design, rustic accents and State of the Art Appliances. Boasting 6 en suite luxury bedrooms and unmatched bathrooms, with deep soaking tubs, artistic tiled showers, custom vanities, walk-in closets, and sitting areas all designed for convenience and comfort. A generous walk-out finished basement, containing over 2000 square feet, will include additional living areas along with a custom home bar, gym/media room and or wine cellar. Other Rare feature is the "Show Stopping Two Story Vaulted Stairway" This Unparalleled design with exceptional visuals highlighted by exquisitely detailed finishes will be SUPER DELUXE; So Be prepared for the "WOW FACTOR " Don't Wait...Call Today to Secure this RARE OFFERING in the POSH PRESERVE Oak Bluffs' Newest Luxury En Clave abutting conservation land and trails for hiking, walking and biking!

Listed by Marilyn Moses Cell 617-462-0381 ANYTIME ! of Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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7 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA7 East Chop Drive

Price$3,000,000

Est. Mortgage: $/month

MLS Number 38509

  • MultiFamily
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.1199

OAK BLUFFS HARBOR/BEACH FRONT THREE FAMILY with a fully equipped DOCK! Perfectly sited EAST CHOP location between harbor and Washington Park. Outstanding water views of Oak Bluffs Harbor and Nantucket Sound beyond. Loaded with island charm and just steps to historic Oak Bluffs village shopping, eateries, ferries and beaches. Tucked in to its very own corner, abutting only one residential property, the setting is unexpectedly private. INCOME PRODUCER this renovated three family waterfront property has a deep water dock that’s conveniently serviced with water and electricity. The first floor is comprised of two apartments; a 2 bedroom, 1 bathroom unit plus a 1 bedroom, 1 bathroom unit with utility room - both have living/kitchen/dining rooms that lead to patio areas facing harbor, beach and dock. The second floor is a spacious retreat with 3 bedrooms and over 1,500 sq. ft. of comfortable open space with living, dining, kitchen and a fabulous den with wood stove and access to the covered deck. PANORAMIC VIEWS and the MARINA at your fingertips – all in the heart of this picturesque seaside town! Excellent rental history and endless possibilities.

Listed by Helena Kirschenbaum of RE/MAX on Island

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Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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104 Winemack Avenue & 101 Park Street Oak Bluffs MA 02557
Pending

MLS Number 38203

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.6887

The Rose Cottage in East Chop - this bright and airy, waterview ca 1920 home with detached garage offers the perfect expanse to spread out in a highly desirable location. Spanning Winemack and Park streets, the property is perfectly set with a beautifully framed view of Vineyard Sound, including regular ferries and boats in passing by. The home is immaculate and deceptively spacious, with five bedrooms and open living areas graciously incorporated on two levels. Indoor and outdoor living is truly superb at this property, with upper and lower decks and a sun room complementing the exceptionally bright and positive interior. Recent renovations include all new siding on three sides, interior and exterior paint, new septic, hvac system upgrades and more. Come grab this rare opportunity in a prime East Chop location - conveniently located to town, beaches and more.

Listed by Peyton Wallace of Compass

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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168 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA168 East Chop Drive

Price$2,650,000

Est. Mortgage: $/month

MLS Number 38342

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.0002

Dramatic Vineyard Sound Views on East Chop Drive - Charming cottage on desirable East Chop Drive - Enjoy spectacular views of Vineyard Sound & boats passing by from your front deck of this cozy Martha's Vineyard retreat. The cottage is just under 1,000 Sf and sits on 12,256 SF of land, and currently features 2 bedrooms and 1 bath. Permits are being prepared for the potential of a new 4 bedroom septic system. This setting offers unbelievable views from a remarkable location in Oak Bluffs.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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26 Pequot Avenue Oak Bluffs MA 02557

Oak Bluffs, MA26 Pequot Avenue

Price$2,250,000

Est. Mortgage: $/month

Pending

MLS Number 38143

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.2

The Cinderella Cottage is a glamorous Victorian Seaside home. Meticulously renovated, this Gingerbread style home on Pequot Ave, puts you just steps from Inkwell Beach & the village of Oak Bluffs. Colorful and decorative detailed gingerbread trim adorns all. A gracious wrap around porch with large side seating area overlooks the grassy green yard. A quiet back slate patio is enclosed with greenery and gardens. The upstairs covered balcony charms with more gingerbread trim. The two story fairytale turret has upper level water views. The etched glass French doors will bring you into a beautiful living room whose high ceilings & decorative trim, marble mantel and hardwood floors delight. The sunny separate dining room continues with tasteful bright colors, etched glass door, high ceilings and its own marble mantel. Double pocket doors open up a big family room off to the side with more high ceilings, decorative trim and arched bay window. The modern kitchen fills the back section of home w/ top-notch appliances and cabinetry, center counter top w/built in snack bar for 4, and designer painted diamond wooden floors. A separate Laundry room, additional half bath and small side enclosed porch to patio complete this floor. Upstairs are three large bedrooms with an additional Extra room turned into a bunkroom for kids. Two full baths (two have gorgeous marble tiles on floors, walls and ceilings, & bead board wainscoting (one w/ claw foot tub, one w/ oversized shower). Each spacious bedroom room is a wonder, professionally decorated with color and style, bay windows and all with hardwood flooring. Additional open study area plus sitting areas outside the rooms are perfect for a quiet break or reading-TV nook. The 2 story turret has what feels like a secret staircase leading up to a game room and up again to a private sitting area with water views. There's so much more with full basement, heat, lovely grounds. This is a home perfect for family and entertaining friends. Keep as a family home or rent weekly. Wonderfully maintained, highly sought after rental area. (Inquire for rental income figures). Turnkey except for personal items. Broker must accompany clients. Showings can be set up for Sat & Sun after 3PM

Listed by Susan Austin of Austin R.E. Properties of MV

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Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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28 Narragansett Avenue Oak Bluffs MA 02557

Oak Bluffs, MA28 Narragansett Avenue

Price$2,195,000

Est. Mortgage: $/month

Active With Contract

MLS Number 28261

  • Residential
  • Bedrooms 9
  • Bathroom 3.5
  • Acreage 0.1

"The Pink Lady" -Located in the heart of Oak Bluffs in the historic Copeland District, this Grand Victorian home has 9 bedrooms; room for the whole family or a great rental property. Charming and spacious with a view of Ocean Park and the water beyond. Two first floor bedrooms including a separate bedroom suite, the second floor has 7 bedrooms many adorned with private porches or balconies. This great dame is just steps away from the beach and town center with shops, restaurants, and entertainment. A long rental history makes this property a solid investment.

Listed by Lisa Lucier of Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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: 2.78% last updated on Jul 22, 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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41 Bayes Hill Road Oak Bluffs MA 02539-4427

Oak Bluffs, MA41 Bayes Hill Road

Price$1,895,000

Est. Mortgage: $/month

MLS Number 38461

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.7699

CUSTOM DESIGN BUILD - exquisite craftsmanship and meticulously maintained - noted island architect, Phil Regan of Hutker Architects, brought his best when he designed this spacious, light filled home for family to enjoy. Character and charm is built into every room, from the glass doors and pantry cupboards of the "East Chop inspired" kitchen to the handwrought chandeliers and sconces by Vermont's Hubbardton Forge, and the fir, ash and maple hardwood accents throughout. Gracious sightlines and lofted ceilings complement airy living and sleeping spaces, including a first floor primary suite, plus spacious hallways that allow for special reading nooks and a kitchen office desk. Both the living and dining rooms open onto the large mahogany deck overlooking a serene park-like setting perfect for entertaining or relaxing at home. The grounds have been beautifully designed with the same care and creativity as the interior, orchestrating beautiful vistas on every side of the property from the lush lawns, hydrangeas, evergreens, ornamental trees, and Japanese maples, arranged for privacy and beauty. The privacy is enhanced by the common land and Land Bank conservation areas behind the property with miles of walking trails to enjoy. Granite steps and pathways, a pea stone drive and an ample one car garage built with the same sophisticated design as the main house, add the finishing touches to this enchanting home. Bayes Hill Association offers residents tennis and pickle ball courts plus easy access to Lagoon Pond for kayaking or swimming, plus immediate connection with the southern woodland trails and to Featherstone Center for the Arts.

Listed by Dawn Bellante Holand, 508.524.1601 of Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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69 Brush Pond Road Oak Bluffs MA 02557

Oak Bluffs, MA69 Brush Pond Road

Price$1,799,000

Est. Mortgage: $/month

MLS Number 38490

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.41

New to market— Oak Bluffs 3 bedroom, 2 bathroom waterfront home. Home office, fireplace, expansive red brick patio, rooftop sundeck which affords one of the most spectacular sunset views on Martha’s Vineyard.

Listed by Barbara Twiss of Laer Realty Partners

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

Pending

MLS Number 35358

  • Residential
  • Mls Status Pending
  • 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: 2.78% last updated on Jul 22, 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

Active With Contract

MLS Number 37959

  • Residential
  • 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: 2.78% last updated on Jul 22, 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 July 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."