Oak Bluffs Real Estate

Oak Bluffs is a classic beach resort town on the northeast shore of Martha's Vineyard. Real estate in Oak Bluffs includes condos, single family homes, homes with dock access, acreage, and more. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

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400 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA400 Barnes Road

Price$7,300,000

Est. Mortgage: $/month

MLS Number 38540

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 2.417

A gated drive sweeps up to the contemporary-designed home. There are 7,000 square feet of luxurious open plan living on 3 levels with multiple rooms connecting you to outdoor entertaining patios and terraces. Relax in the infinity pool with waterfalls on 2 sides or the Spa pool while taking in the views of Lagoon Pond. The distinctive interior features generous living spaces designed with high open ceilings, full-length windows, exquisite materials, and high-end finishes throughout. Solar panels installed. There are 6 bedrooms, 5 bathrooms situated in areas throughout the floor plan to provide privacy when there is a full house. An elegant media and entertainment room with 106” flat-screen TV, full bar and wine cellar and a full bath. The gym is outfitted with professional equipment with a full wall of glass opens up to the outside lounging terrace and around to the pool and an outdoor rain shower. Enter from the two-car attached garage and an elevator provides a lift to the other living levels. The residence is surrounded by beautiful landscaping and terraced gardens, and further protected by the abutting 190 acres of the Land Bank Southern Woodlands property.

Listed by Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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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 Island Real Estate

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 displays 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 Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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

Pending

MLS Number 38509

  • MultiFamily
  • Mls Status Pending
  • 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 RE/MAX on Island

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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6 Brewster Avenue Oak Bluffs MA 02557

Oak Bluffs, MA6 Brewster Avenue

Price$2,775,000

Est. Mortgage: $/month

MLS Number 38609

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.1147

Panoramic Ocean Views. This exceptional Victorian style family home and guest cottage has dramatic water views from inside and outside of its ideal location. A park across the way will remain park land in perpetuity, adding to the expansive feel and play opportunities that any family would cherish for a lifetime. The historic Victorian style family home built in 1883 was completely rebuilt in 2010 to allow for comfortable year round living. The 4 bedroom main house was carefully elevated and a full foundation was poured, winterizing with FHA heat and insulation. Impeccable care was taken in order to retain all of the vintage architectural features and details of the home while allowing for modern touches and comfort. Original built-in's, cross beams and wide plank floors protect the whimsical style of this much loved family home. The new full basement creates storage and safe keeping of utilities and the potential for additional living space if desired. Walk to town, beach, tennis and East Chop parkland including the historic East Chop Lighthouse. Facing a park, many evening games , laughter and joy have been tradition for this Vineyard family home.

Listed by Breakwater MV

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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125 Seaview Avenue Oak Bluffs MA 02557

Oak Bluffs, MA125 Seaview Avenue

Price$2,497,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38620

  • Residential
  • Bedrooms 6
  • Bathroom 3.5
  • Acreage 0.1

Forever Views, Views and more Views! This Ocean facing Victorian home has sweeping water views across Nantucket Sound as well as Farm Pond. Loaded with charming details, the generous rooms offer ease for summertime gatherings and entertaining. Delightfully sited and expanded over time, the large welcoming porch sets the comfortable pace as each room flows to another. Front parlor, den, dining room, convenient laundry/storage room and a renovated kitchen - plus a multitasking overflow room with bathroom and a bedroom suite with private entrance at the rear. Front and back, the two staircases lead to the five bedrooms and two bathrooms. Plenty of convenient parking and easy access to the grassy backyard complete with BBQ area and outdoor shower. Impressive rental history, this treasured cottage style home is steeped in happy Vineyard vibes!

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Austin R.E. Properties of MV

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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16 Atlantic Avenue Oak Bluffs MA 02557

Oak Bluffs, MA16 Atlantic Avenue

Price$2,095,000

Est. Mortgage: $/month

MLS Number 38261

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 2.5
  • Acreage 0.4971

Incredible Opportunity, Location and property. Main House and new Detached Studio and Full Basement. Atlantic Avenue is a short road that runs parallel to East Chop Drive, a block over from the East Chop Lighthouse and within earshot of the soothing sounds of the ocean. The Main house, built in 1890, is a classic example of traditional Victorian architecture and has been carefully restored to summer-living condition with painted ginger bread trim and a wrap around porch. A huge open kitchen w/cathedral ceiling is simple and functional. The back door off the kitchen leads to a screened in porch for alfresco dining and lounging. The beautifully refinished wood floors and leaded glass windows extol the simplicity and traits of days gone by. With 4 existing bedrooms and 1.5 baths, the house has been newly insulated and is painted waiting for your finishing touches. A brick fireplace and wide open living area will stir some creative juices and allow you to imprint your personal style of this neutral background. There is a new 7 bedroom septic system to allow for future expansion.

Listed by Breakwater MV

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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$1,950,000

Est. Mortgage: $/month

Pending

MLS Number 28261

  • Residential
  • Mls Status Pending
  • 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 Anchor Realty of Martha's Vineyard

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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113 Dukes County Avenue Oak Bluffs MA 02557

Oak Bluffs, MA113 Dukes County Avenue

Price$1,899,000

Est. Mortgage: $/month

MLS Number 32334

  • MultiFamily
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 0.0826

Rare offering IN TOWN OAK BLUFFS! Commercially Zoned multi family with a solid SUBSTANTIAL existing rental history. Built in 2017 in excellent condition and within walking distance to Oak Bluffs Harbor, Sandy Beaches, Art Galleries, Shopping, Restaurants and STEPS to Historic Martha's Vineyard Camp Meeting Association and Circuit Avenue! Recently, JULY 2021 NEW SOLAR PANELS! Features include State of the Art Energy Efficient Utilities and Low Maintenance decking, 1.5"closed cell foam insulation on the walls 3"closed cell on the roof and interior walls. Extremely energy efficient. Anderson Craftsmen series energy compliant. Energy Efficient Heat and AC Pumps throughout! Seller has not booked any rentals for 2022. FLEXIBLE INVESTMENT -HIGH RENTS & or CONDO CONVERSION..$$$$$$$$$$$$$$$ 3 Properties being sold as a multi family ! Unit A offers 2 BR1.5 bath, living/ dining area closets throughout partial basement, yard, decks, outside shower, energy efficient throughout ! Unit B is attached with 1 bedroom full bath and living area partial basement interior access, outside shower, yard energy efficient throughout! 3rd unit is a stand alone cottage with open bright high vaulted ceiling,1 bedroom and loft full bathroom energy efficient throughout! Notice required there are rentals in place call listing agent today. NEW PHOTOS COMING SOON! PHOTOS IN LISTING PRIOR to be FURNISHED..

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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

Pending

MLS Number 38461

  • Residential
  • Mls Status Pending
  • 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 Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 September 24, 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."