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

The driveway sweeps up to the contemporary-designed 7,000 square foot home 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 french doors opening up to the outside Zen garden 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: 3.11% last updated on Dec 2, 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: 3.11% last updated on Dec 2, 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 Beach Road # 28 Oak Bluffs MA 02557

Oak Bluffs, MA28 Beach Road # 28

Price$4,500,000

Est. Mortgage: $/month

MLS Number 38934

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.99

A Coup d' Ville in Oak Bluffs! This property is built across 6 lots spanning about .99 acres of land. Newly constructed in 2017 perched upon concrete pillars with breakaway walls that serve as added garage space or entertainment space beneath the home. The home is perfectly located with spectacular, unobstructed views of the Harbor and Lagoon. Relaxing on the multi level deck while watching the sailboats and ferries come and go is sensational - watching the sunsets are a daily activity and something to boast about on a nightly basis. The sound and shatter proof windows allows the experience of the beautiful island scenery while affording the luxury of personal privacy at the same time. The lot is spacious enough to add another structure or the possibility of a privately fenced in ground pool . The Bedrooms are all oversized with the master featuring a walk in closet and suite bathroom . The views of the Harbor and Lagoon can be accessed from 90% of the home on both levels - There is 1800 sqft of living space with an additional 800 sqft of deck space big enough to enjoy lunch or dinner outdoors while taking in the views from all angles. Ash hardwood makes up the flooring throughout the home with open floor space to enjoy modern living. Central Air, propane fire place , electrical heat pump controlled with gas cooking add to the comfortability. The exterior boast enclosed out side shower , a garden aligned with beautiful flowering that surround decking for outside grilling with plenty of space left for yard games. The irrigation system keeps the yard plush and green .... The State is building a bike path that goes directly down beach road past the home .The project is expected to increase the value and visibility. A privacy fence can be added to the lot to enrich the property without obstructing its nature or views while increasing the rental value through such exposure. From an investment prospective the property produced over 150k in rental income over 6-7 month period in 2021. The property is fully booked from August 1, 2022 through September 17th , 2022 at a rate over 65K . The property rents all season long as we enjoyed rental income each month of the year . We take advantage of enjoying the property when not rented and strike the perfect balance of earning passive income while enjoying our home at the same time. The sale of this property is subject to Seller going into contract for another property that is currently in negotiations.

Listed by Lewis Real Estate Services,LLC

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%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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34 Windemere Road Oak Bluffs MA 02557

Oak Bluffs, MA34 Windemere Road

Price$3,999,000

Est. Mortgage: $/month

MLS Number 38803

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.7242

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbath. Two story Beach Cottage, first floor kitchen leads to the dining, living and sunroom, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with waterview, Guest Bunk bedroom and Twin bedroom which both share full bath. Wood floors, waterviews throughout, new outdoor shower, Shed, and a Gazebo. Leases are in place for 2022 to be transferred to Buyer at closing. Easy to show.

Listed by Island Home Realty Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

Pending

MLS Number 38609

  • Residential
  • Mls Status Pending
  • 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: 3.11% last updated on Dec 2, 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: 3.11% last updated on Dec 2, 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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375 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA375 Barnes Road

Price$2,500,000

Est. Mortgage: $/month

Pending

MLS Number 38836

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathroom 1.5
  • Acreage 1

RARE WATERFRONT OPPORTUNITY! With over 130’ of frontage on the Lagoon, enjoy a private sandy beach, perfect for swimming, kayaking or just sitting in the sun. Overlooking the Lagoon, the home, built and owned by one family for more than 50 years, offers spectacular views of wildlife and all that happens on the water as well as breathtaking sunsets. This year-round three-bedroom, one and a half bath home is set on a full acre of mature trees and flowering shrubs, which offer privacy but easy access to all the Island has to offer. Sourati Engineering Group has been engaged to design and obtain Town approvals for a three-bedroom sewerage disposal system and a comprehensive existing conditions site plan reflecting environmental areas. Sellers will contribute $35,000 at closing to the execution of the new Title V compliant system and elimination of the old cesspool.

Listed by Donnelly + Co

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 Sea View Avenue Oak Bluffs MA 02557

Oak Bluffs, MA125 Sea View Avenue

Price$2,497,000

Est. Mortgage: $/month

Pending

MLS Number 38620

  • Residential
  • Mls Status Pending
  • 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: 3.11% last updated on Dec 2, 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

Pending

MLS Number 38261

  • Residential
  • Mls Status Pending
  • 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. This property is being sold As Is. There is a new 7 bedroom septic system to allow for future expansion.

Listed by Breakwater MV

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$
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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 4
  • 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: 3.11% last updated on Dec 2, 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: 3.11% last updated on Dec 2, 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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60 Pennacook Avenue Oak Bluffs MA 02557

Oak Bluffs, MA60 Pennacook Avenue

Price$1,800,000

Est. Mortgage: $/month

MLS Number 38343

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.06

Nestled in the heart of the Cottage City and Copeland Historic Districts, this antique home is within walking distance to everything. Beaches, Boats, Restaurants, Shopping, Playground, Basketball, Pickleball, Tennis, Parks, Bike Path and more. Watch the world go by as you laze on your shaded front porch after a day on the beach and a soak in the hot tub. This corner lot in a quintessential Victorian neighborhood offers much privacy overlooking Pennacook Park and much convenience with it's central location.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 December 5, 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."