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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150 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA150 East Chop Drive

Price$13,200,000

Est. Mortgage: $/month

MLS Number 42039

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 8
  • Acreage 0.64

Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home, it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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47 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA47 East Chop Drive

Price$11,000,000

Est. Mortgage: $/month

MLS Number 40789

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 6
  • Acreage 0.29

East Chop waterfront – Once in a lifetime, a property of this caliber becomes available, with an on-the-water East Chop location, a wide range of amenities, and multi-functional use! Uses include -- 1.) Currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 2.) Use it as a residential home or family compound, or live in a portion and rent a portion, 3.) Potential to convert to condominiums, paperwork presently in process but would be a buyers choice. Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 6-unit property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Private outdoor shower with dressing area. On town sewer.

Listed by MV Luxury Homes

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 Ocean Avenue Oak Bluffs MA 02557

Oak Bluffs, MA89 Ocean Avenue

Price$5,950,000

Est. Mortgage: $/month

MLS Number 36402

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 4.5
  • Acreage 0.23

The GRAND DAME of HISTORIC OCEAN PARK ~A VICTORIAN MASTERPIECE, meticulously restored and renovated with careful attention to detail throughout, is situated on OCEAN PARK, Oak Bluffs’ most popular and attractive neighborhood just steps to the white sandy beaches on Vineyard Sound, fine shopping, art galleries, restaurants, Harbor, and Ferry ports! This Victorian treasure is the epitome of the coveted Oak Bluffs porch culture where families have enjoyed the dramatic sunsets and spectacular Summer fireworks for generations. Situated on a professionally landscaped quarter acre, bursting with shrubs and seasonal flowers, that offers a commanding view over Ocean Park and a stunning panorama that sweeps across Nantucket Sound to the shores of Cape Cod. The site has plenty of parking and a broad expanse of lawn in the back yard offering privacy and recreational space. This cheerful design with its luxurious French Doors and abundance of windows captures the natural light that flows through the cozy rooms and seamlessly connects the interior to the outdoor oasis. The 3265 sq feet of interior living area offers the perfect combination of spacious entertaining and intimate settings ideal for the comfort and enjoyment of family and guests. There are 7 charming bedrooms, 3 are primary en-suites with one featuring a soaking tub….a total of 4 and 1/2 exquisite bathrooms. The Chef's kitchen is not just efficient, but a delight and fun place to work and hang out; and the formal dining room features a custom fine woodwork table that seats 12(included in the sale) and efficient propane stove. There are several living/parlor rooms in both the front and rear that complement the overall interior arrangement. Other highlights in this exceptional residence include the impressive millwork, classic beadboard, high ceilings, the walk-in pantry, separate prep kitchen, and a Dry Full Basement! From this desirable location you will enjoy the casual walk around town, jog on the beach, and bike along Sea View Avenue overlooking the Sound. THIS IS TRULY A SPECIAL PROPERTY…and it comes with a proven rental history in place. TITLE 5 PASSED report in documents for 7 Bedrooms !

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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0 Eastville Avenue Oak Bluffs MA 02557

Oak Bluffs, MA0 Eastville Avenue

Price$4,400,000

Est. Mortgage: $/month

MLS Number 40762

  • Land
  • Mls Status Active
  • Acreage 4.8

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling. Septic permits in place for two lots. Lot #1 - 147.2 (45,782sq.ft.) Permit in place for an APPROVED 6 Bedroom Septic System; Lot #2 - 147.3 - (31,320sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #3 - 147.4 - (34,824sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #4 - (52,451sq.ft.) 6 Bedroom Septic System Designed, NOT YET submitted; Lot #5 - (45,074sq.ft.) - Permit in place, APPROVED for a 4 Bedroom Septic System. Lot # 5 - May have access directly from Wapello Street. Ten (10) Bedrooms have been approved. Applications for an additional Twelve (12) Bedrooms are in process. Lot#2 - Application for 6 bedrooms. Lot#3 - Application for 6 Bedrooms. Lot #4 is undetermined at this point. Access may be allowed via Sunset Road or Eastville Avenue. Water is available via Sunset Road, at the property. Electricity is on site. Buyer is responsible for verifying any and all information on this property.

Listed by Alisan Lohan-Conway Properties

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9 Weston Avenue Oak Bluffs MA 02557

Oak Bluffs, MA9 Weston Avenue

Price$4,295,000

Est. Mortgage: $/month

MLS Number 41083

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.4

East Chop charmer. This property is nestled in the heart of East Chop and offers spectacular views of the Sound from the living room, screened porch, primary bedroom, and two large water-facing porches. You can watch the ferries coming and going and the sailboats cruising by. East Chop Drive is one of the island's favorite walking spots and it's right in front of this property. The house has been well cared-for and there is also ample opportunity to put your finishing touches on it. In addition to the 4-bedroom, 3-bath home there is a large garage that offers options for the future owner.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 Oak Bluffs MA 02557

Oak Bluffs, MA28 Beach Road

Price$4,200,000

Est. Mortgage: $/month

MLS Number 41767

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

Designed to Capture the views of the Vineyard Sound and beyond. Built in 2017 and created to be a comfortable home for year round or Summer living. 4 Over-sized Bedrooms, 2.5 bath Rooms on Two levels with covered decks facing Vineyard Sound and the lagoon. First Level features 3 bedroom, spacious family room, full bath with laundry and storage . The second Level features open floor plan with a gourmet kitchen, stainless steel Thermador appliances, stone counter tops, gas fire place and abundance of cabinets. The master en suite has high ceilings with master bathroom , spacious closet and amazing views of the Sound and Lagoon ( unobstructed views ) Come tour - it's a must see. Whether you're looking for passive income or year round relaxation this is the perfect home ! The exterior offers an outside shower , grilling area , spacious front and rear yards , walking distance to Eastville and Martha's Vineyard Land Bank Parking and Beach

Listed by Lewis Real Estate Services,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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311 East Chop Drive Oak Bluffs MA 02557

Oak Bluffs, MA311 East Chop Drive

Price$3,250,000

Est. Mortgage: $/month

MLS Number 41412

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.25

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 Greenleaf Avenue Oak Bluffs MA 02539

Oak Bluffs, MA22 Greenleaf Avenue

Price$2,990,000

Est. Mortgage: $/month

MLS Number 42013

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.18

Immersed in the picturesque setting of Oak Bluffs on Martha's Vineyard, Fairview on Greenleaf Avenue, one of only ten homes in this coveted location, harmoniously blends historical charm with coastal serenity. This cherished family home holds a special place in the hearts of its owners, with roots tracing back to childhood memories and the family's Rochester, NY home on Fairview Crescent. Architecturally designed to echo the local gingerbread cottages, an addition seamlessly integrates with Oak Bluffs' historical aesthetic. The highlight? A rooftop deck, offering unparalleled views—the highest point on Greenleaf Ave—overlooking Lakeside Park, the rejuvenated Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound beyond. This commanding viewpoint makes Fairview the ideal spot for enjoying the annual Oak Bluffs fireworks display and glorious sunrises. For over 27 years, Fairview has been a sanctuary of family memories, lovingly maintained and enjoyed by multiple generations. It features three bedrooms and a finished basement that provides additional flexible living space. See the included photos to envision how the lower level would look with furniture and a traditional staircase. The spacious backyard and the large multipurpose building, which functions as both a shed and garage, add to the property's charm and utility. The large lot includes ample parking off of Gorham Ave. Located on a peaceful side street, Fairview enjoys proximity to the heart of Oak Bluffs' vibrant community life, including traditions like Illumination Night, concerts at the Tabernacle, and walks to Ocean Park. Yet, it offers a quiet retreat, close to all the town's amenities without being in the midst of the hustle and bustle. Noteworthy is the involvement of Island architect Jaime Weisman in the addition, ensuring thoughtful design and execution. Fairview isn't just a home; it's a gateway to a lifestyle enriched by the enchantment of Oak Bluffs, celebrated for its historic landmarks and coastal charm. It represents a rare opportunity to continue a legacy of creating memories in a setting that combines the best of Martha's Vineyard's natural beauty and cultural richness.

Listed by Compass | The O'Hanlon Group

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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$2,950,000

Est. Mortgage: $/month

MLS Number 40654

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.72

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 sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2024 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

Listed by Island Home Realty Inc.

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%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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2 East Side Road Oak Bluffs MA 02557

Oak Bluffs, MA2 East Side Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 41587

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.25

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the covered porch. Watch the ferries come and go and delight in the dazzling colors of the setting sun. Recent renovations include raising the house and the pouring of a foundation offering an additional 930 square feet of lower level living area. Experience true Vineyard living at its best, just steps away is easy access to the Lagoon with clamming, swimming, and boating. Bring your vision to the open and airy studio/ bunkhouse that is included in this offering at 60 Bay View Avenue and features the same wonderful vistas. Two unbuildable lots abut this property so you will never lose sight of the breathtaking scenery. This classic home is a rare Vineyard offering and not to be missed.

Listed by Donnelly + Co

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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4 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 High Meadow Lane

Price$2,650,000

Est. Mortgage: $/month

MLS Number 41548

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.8899

Set back and overlooking a sprawling front yard from the quintessential farmer’s porch you can envision family and friends enjoying the outdoors! Soaring cathedral ceilings and beautiful craftsmanship will immediately capture your attention upon entering this expansive cape style home. Many upgrades make this a gracious charmer from the get go.. The floor plan is fabulous, from the bright large kitchen outfitted with ample granite counters, rugged commercial Wolf stove, wine fridge and eat-in counter plus table eating is perfect for family gatherings and entertaining. SOLID is the best way to describe what you will experience when you visit this home. Post and Beam construction levels up with Energy Efficient SIP style of insulation plus Radiant heat through the floors. Central AC and great use of sized windows lets all the light in! First floor primary bedroom is spacious with walk in closet and full bathroom with tub. There is a 2nd bedroom that is currently being used as a TV room. 2 more sizeable bedrooms ensuite and closets complete the 2nd floor. The Lower level is partially finished with key and perfect for multigenerational flex space and or a game room or office. Bring your imagination and personalize the possibilities! There is more! A large Garage with additional space above that can be finished for other creative use. Situated on .89 acres of land, so much yard for all occasions. Lawn games, get togethers outdoor fun all surrounded by beautiful landscaping and Abutting a buffer of Common Land! This is an impressive home base perfect for year-round, a fabulous vacation spot and or generate impressive rental income. Meadow View Farms is a lovely welcoming community that offers beautiful walking paths, along with Association Tennis courts. Perfectly convenient to the bike paths, bus routes central to the down island towns. Title V inspection has been completed and passed.

Listed by C McManus Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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107 & 105 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA107 & 105 Barnes Road

Price$2,625,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41961

  • Residential
  • Bedrooms 5
  • Bathroom 2
  • Acreage 1.03

A Rare and Unique Waterfront Offering. This listing consists of two non-contiguous parcels separated by a "paper road". You will sure to be intrigued when you consider the possibilities of what these properties have to offer. 107 Barnes Road has been enjoyed by the same family for generations. The five bedroom home is well set back from the road on over an acre of beautiful land with direct water access from a staircase to the beach. There is room for expansion of the main house as well as the possibility of a guest house with the proper permitting. This property awaits a new owner's vision for the future and creating memories for a lifetime. Separated by a paper Road (Lagrange Ave) 105 Barnes Road is the second 14,375sf parcel offering even more flexibility and opportunity (the assessed value of this lot, 539,900, is included in the total land assessment) Lagoon Pond is your playground with easy access through the drawbridge to the Vineyard Haven harbor and the Nantucket Sound beyond. Grab your swimsuit and the kids and get ready for Summer fun. Swimming, clamming, and boating are all accessible right from your front doorstep. Relax with a glass of wine on your own private beach while enjoying exceptional sunsets and lazy afternoons. An incredible opportunity to create a one-of-a-kind waterfront family compound on Martha's Vineyard. An opportunity not to be missed.

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 LINKMV as of June 14, 2024 . All data is obtained from various sources and has not been, and will not be, verified by broker or 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.