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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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: 7.22% last updated on Nov 30, 2023
* 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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267 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA267 Barnes Road

Price$5,850,000

Est. Mortgage: $/month

MLS Number 39954

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 5.5
  • Acreage 1.25

Enjoy waterfront living at its best with 163’ of Lagoon frontage including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning waterviews and spectacular sunsets. This is your time to enjoy Vineyard life on the water…boating, swimming, kayaking, clamming, and more. Perfect for entertaining and comfortable living, the immaculate 4,046 square foot home with a newly finished 2,000 square foot walk-out basement has a wonderful flow throughout and waterviews from almost every room. It was designed to capture the essence of waterfront life. It is rare to find a home in a setting like this on Martha’s Vineyard. Tucked away just off Barnes Road, it feels as if you are in a remote locale, yet close to all the Island has to offer. The main level, with soaring ceilings, is comprised of a large living area enjoying a wood-burning fireplace and wet bar, a sitting area, half-bath, dining room, and a large kitchen with eat-in dining, with full views of the Lagoon and access to the outdoor patio. Two additional rooms with a private deck and full bath are cleverly located in a separate wing of this floor and can be used as an office or den. Unique to the second floor is a wraparound deck and screened porch overlooking the Lagoon and adjoining the large primary suite with a second wood-burning fireplace and two spacious ensuite bedrooms, all with fabulous views. If you are looking for a quiet space, you can enjoy a second covered porch at the front of the house. Being sold furnished, this is the ultimate Vineyard Experience.

Listed by Donnelly + Co

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%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 (4.4 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 a 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 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. Currently clarifying height restriction and whether or not basements are allowed. 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: 7.22% last updated on Nov 30, 2023
* 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: 7.22% last updated on Nov 30, 2023
* 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: 7.22% last updated on Nov 30, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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111 Eastville Avenue Oak Bluffs MA 02557

Oak Bluffs, MA111 Eastville Avenue

Price$3,200,000

Est. Mortgage: $/month

MLS Number 41243

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 4
  • Acreage 0.43

Welcome to Captain Shaw Norris House, where luxury meets coastal charm! Situated in the picturesque Nab’s Corner neighborhood, 111 Eastville Ave is a stunning property that is steps from the ocean. This historic whaling captain’s house boasts six bedrooms and four luxurious marble bathrooms. Plenty of room for friends and family or you can use the property as a high-end rental. An outstanding feature of this exceptional property is the expansive roof deck. Ascend to the top and be greeted by breathtaking harbor and ocean views that will leave you in awe. Imagine sipping your morning coffee or hosting unforgettable gatherings against this captivating backdrop, with the rhythmic sounds of the waves providing a soothing soundtrack to your life. Marvel at the ever-changing colors of the sky as the sun sets, illuminating the harbor with a golden hue. Watch as boats sail by, a gentle reminder of the maritime heritage that defines this island community. This roof deck is an exquisite refuge to relax and unwind, gathering memories that will last a lifetime. ---------------------------------------------------------------------------------------------------------- This is the perfect Oak Bluffs location! Walk to the beach or take a leisurely walk to downtown Oak Bluffs with its exciting and lively restaurants on the harbor. Enjoy strolling along the quaint historic gingerbread cottages or the charming shops of downtown Oak Bluffs. Or you can walk or bike on a new bike path to Vineyard Haven. The historic Captain Shaw Norris House, built in 1859, has been completely renovated and features, new insulation, electrical wiring, plumbing, bathrooms, roofing, siding, trim, windows, HVAC, and a custom-designed kitchen. There are many original architectural elements featured in this Greek Revival, such as an ancient brick hearth. Whether you are looking for a year-round residence or an exquisite vacation home, this property presents an unparalleled opportunity to create lifelong memories against a backdrop of stunning harbor and ocean views. Prepare to indulge in the island lifestyle and make this Martha's Vineyard gem yours today! Broker has an equity interest in the property.

Listed by Arrowhead Homes

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%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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15 Peter Williamson Boulevard Oak Bluffs MA 02557
Pending

MLS Number 41389

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 1.37

Welcome to where elegance and tranquility meet! Nestled on a serene private lot, this exceptional property offers a lifestyle of luxury and comfort, making it the perfect island oasis for discerning homeowners. Step inside to discover an expansive open-concept floor plan flooded with natural light. High ceilings, hardwood floors, and elegant fixtures create an inviting atmosphere. The living area is perfect for entertaining, and a gourmet kitchen with top-of-the-line appliances makes cooking a pleasure. The property features 6 well-appointed bedrooms, including a luxurious master suite. Enjoy ample closet space, and unwind in the spa-like bathrooms. The beautifully landscaped grounds provide an outdoor paradise with lush gardens and mature trees adding to the ambiance. Enjoy al fresco dining on the spacious patio. This exquisite property promises an idyllic blend of comfort, style, and natural beauty, setting the stage for a lifetime of cherished memories. Comes fully furnished and boasts a strong rental income history!

Listed by Compass | Point B

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 2023 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: 7.22% last updated on Nov 30, 2023
* 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 Hudson Avenue Oak Bluffs MA 02557

Oak Bluffs, MA21 Hudson Avenue

Price$2,950,000

Est. Mortgage: $/month

MLS Number 41542

  • MultiFamily
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 4.5
  • Acreage 0.4399

Income Generating Wonder! Calling all Contractors, Business Owners, Entrepreneurs, Investors with vision., Now is the perfect time to make a smart move in real estate ownership that provides choices and many possibilities. Do you need housing for your employees? This property has it! Originally designed as the owner's apartment and housing for the entire staff of the Pequot Hotel, the property includes an oversize two-bedroom “owners’ apartment” with large kitchen and two baths. Alongside is a shared dormitory style rental space, 8 bedrooms with common XL Kitchen and three baths. There are two large garage bays with large storage ability, featuring a half bath and an office. 11-foot ceilings, and plentiful shelving, heat etc. Perfect for storing all types of equipment or even space for boats. Set back privately on the backside of the lot there is also plenty of parking and a lovely yard for outdoor enjoyment. 21 Hudson is situated in the sought-after zip code 02557, conveniently located within walking distance to the bus route and bike paths, off County Rd. Whether you're looking to live, work, or rent, this property is ready for you! A Truly RARE REAL ESTATE GEM! Square Footage is a total of both units and all data included here is from Town of OB Assessors.. This is a unique offering - A Must See to understand and appreciate all that it offers.

Listed by C McManus Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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37 Nashawena Park Oak Bluffs MA 02557

Oak Bluffs, MA37 Nashawena Park

Price$2,700,000

Est. Mortgage: $/month

MLS Number 40883

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 2.5
  • Acreage 0.18

Rare opportunity to own a charming 8 bedroom Classic Victorian Home in one of the most popular locations, which is in Cottage City and Copeland Historical District. Great neighborhood, just walking distance to Inkwell beach,Circuit Ave, Harbor, basketball, tennis, pickle ball courts and playground. Lovely large yard with a wonderful wrap around porch. This home features, living room, dining, kitchen, 8 bedrooms, and 2.5 baths. You will find the laundry room in the outdoor shed, with the attached outdoor shower . During shoulder season for comfort there is a Rinnai heater located in the kitchen. This home has been enjoyed by the family over 69 years and now it is time for a new family to experience just as many. The owner prefers no closing before November.

Listed by Island Home Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA107 Barnes Road

Price$2,675,000

Est. Mortgage: $/month

MLS Number 41001

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1.03

A water lover’s delight! Perched high on the Lagoon on a large wooded lot sits “The Yellow House”. Loved by the same family for generations you will be intrigued by what this property has to offer. Lagoon Pond is your playground, with easy access through the drawbridge to the Vineyard Haven harbor and the Nantucket Sound beyond. This four bedroom home is set back from the road and is awaiting a new owner's vision for the future and creating memories for a lifetime. 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. There is room for expansion of the main house as well as the possibility of a guest house with the proper permitting as there is a 5 bedroom Title V septic system currently in place. If that is not enough to excite and delight- this special offering comes with an additional, separate 14,000 sf parcel. A spectacular 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

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$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 2.5
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 December 5, 2023 . 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.