Oak Bluffs Homes

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  /21

  $1,650,000

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

  

  Alice Pierce

  Coldwell Banker Realty - Hingham

  (508) 715-6242

  9 Brunswick Ave, Oak Bluffs, MA 02557
• 

  Explore Oak Bluffs

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  /41

  $8,750 per month plus fees

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  11 High Meadow Ln, Vineyard Haven, MA 02568

  Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor full bath, plus additional half bath on main level. The

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
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  /26

  $1,450,000 Sold Sep 12, 2025

  • 3,352 Sq Ft
  • $433/SF
  • 8 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1975

  48 Brewster Ave, Oak Bluffs, MA 02557

  EAST CHOP - LOCATION- LOCATION . A RENOVATOR'S DREAM - A 5 bedroom multi-level home with an approved Title 5 septic system for 5 bedrooms - and just 1/2 mile to the harbor and town center. One lot from the East Chop Association Tennis Club. "You can change your house - but not your neighborhood" and this is a very special neighborhood. House needs much TLC - to be sold AS IS. Priced well

  Patti Dean Wiggy's Pond Real Estate

  48 Brewster Ave, Oak Bluffs, MA 02557
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  /3

  Est $1,634,299 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  18 Towanticut Ave, Oak Bluffs, MA 02557

  18 Towanticut Ave, Oak Bluffs, MA 02557
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  /42

  $5,995,000

  • 3 Beds
  • 6 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

  

  Wendy Harman

  Compass

  (508) 205-8817

  385 Barnes Rd, Vineyard Haven, MA 02568
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  /20

  $14,000 per month plus fees

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  55 Samoset Ave, Oak Bluffs, MA 02557

  Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  55 Samoset Ave, Oak Bluffs, MA 02557
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  /21

  $500,000 Sold Sep 12, 2025

  • 604 Sq Ft
  • $828/SF
  • 58 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1870

  21 Rock Ave, Oak Bluffs, MA 02557

  Experience the charm of 21 Rock Avenue, nestled in the Historic Martha's Vineyard Camp Meeting Association. This year-round cottage features 1 bedroom and 1 bath, and is just moments away from Oak Bluffs Harbor, ferry ports, sandy beaches, art galleries, and delightful restaurants. Recent exterior enhancements include cedar fencing, refreshed house trim, new paint, and an upgraded roof. Please

  Marilyn Moses Ocean Park Realty Inc

  21 Rock Ave, Oak Bluffs, MA 02557
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  /21

  Est $1,115,009 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  10 Lagoon Rd, Oak Bluffs, MA 02557

  10 Lagoon Rd, Oak Bluffs, MA 02557
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  /32

  $985,000

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

  Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 514-5238

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
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  /30

  $28,500 per month plus fees

  • 9 Beds
  • 6.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design.

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /40

  $650,000 Sold Sep 10, 2025

  • 759 Sq Ft
  • $856/SF
  • 251 Days On Market

  • 2 Beds
  • 0.5 Baths
  • Built 1900

  25 Oak Ave, Oak Bluffs, MA 02557

  WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the existing building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) bedrooms as it’s not in a Board of Health area of concern -

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  25 Oak Ave, Oak Bluffs, MA 02557
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  /31

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  12 Fairway Dr, Vineyard Haven, MA 02568

  12 Fairway Dr, Vineyard Haven, MA 02568
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  /24

  $935,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

  Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 422-4131

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
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  /10

  $20,000 per month plus fees

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
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  /20

  $1,295,000 Sold Sep 05, 2025

  • 1,584 Sq Ft
  • $818/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1988

  2 Upper Douglas Ln, Oak Bluffs, MA 02557

  Are you still looking for a year-round, island home for your family and only finding homes that are either not in your price range or are badly in need of renovation? Look no further because all that work has been done for you with this property. Just move in and enjoy the convenient location -- close to town, schools, hospital and public transportation. This low-maintenance, 4 bedroom, 2 bath

  Lynn Buder Sandpiper Realty

  2 Upper Douglas Ln, Oak Bluffs, MA 02557
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  /37

  Est $1,475,463 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  12 Fairway Dr, Oak Bluffs, MA 02557

  12 Fairway Dr, Oak Bluffs, MA 02557
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  /34

  $2,500,000

  • 6 Beds
  • 2.5 Baths
  • 1,666 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 348-7972

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /20

  $20,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
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  /30

  $1,995,000 Sold Aug 29, 2025

  • 2,891 Sq Ft
  • $690/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  26 Box Turtle Ln, Oak Bluffs, MA 02557

  This delightful home is on a scenic lot nestled within the Sengekontacket Association. Every room in the home is filled with natural light and beautiful views. It is a very short walking distance to the community boat dock and kayaking, as well as the walking trails of Sengy.Updated in 2008 by the architect owner, this home has 3 bedrooms in the main house and a lovely bedroom and bathroom in

  Jayne Isford Ocean Park Realty Inc

  26 Box Turtle Ln, Oak Bluffs, MA 02557
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  /38

  Est $1,035,943 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  287 County Rd, Vineyard Haven, MA 02568

  287 County Rd, Vineyard Haven, MA 02568
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  /27

  $1,200,000

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  70 Carol Ln, Oak Bluffs, MA 02557

  Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 456-5742

  70 Carol Ln, Oak Bluffs, MA 02557
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  /29

  $64,000 per month plus fees

  • 4 Beds
  • 7 Baths
  • 3,600 Sq Ft
  • House for Rent

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
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  /23

  $1,800,000 Sold Aug 26, 2025

  • 1,351 Sq Ft
  • $1,332/SF
  • 0 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1910

  12 Martha's Park Rd, Oak Bluffs, MA 02557

  Harthaven Cottage - This magical cottage, tucked away just 2/10's of a mile from the private association beach, is waiting for you to call it your own. A covered porch welcomes you. Once inside, you begin to take in the charming details of this classic 3-season home. There are cathedral ceilings with exposes painted beams. Home features 4 bedrooms, 1 1/2 baths and outdoor shower. Both bathrooms

  Michele Moore Island Real Estate

  12 Martha's Park Rd, Oak Bluffs, MA 02557
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  /17

  Est $1,560,673 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft

  19 Quantapog Rd, Vineyard Haven, MA 02568

  19 Quantapog Rd, Vineyard Haven, MA 02568
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  /32

  $1,550,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,304 Sq Ft

  11 John Wesley Ave, Oak Bluffs, MA 02568

  East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 682-5574

  11 John Wesley Ave, Oak Bluffs, MA 02568
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  /25

  $24,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
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  /19

  $1,449,000 Sold Aug 19, 2025

  • 2,284 Sq Ft
  • $634/SF
  • 263 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  14 High Meadow Ln, Oak Bluffs, MA 02557

  MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open floor plan with cathedral ceilings and 3 sliding doors that

  Michele Moore Island Real Estate

  14 High Meadow Ln, Oak Bluffs, MA 02557
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  /12

  Est $1,304,936 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft

  3 Carole Ave, Vineyard Haven, MA 02568

  3 Carole Ave, Vineyard Haven, MA 02568
• 

  

  /22

  $1,250,000

  • 2 Beds
  • 1 Bath
  • 742 Sq Ft

  47 Winemack St, Oak Bluffs, MA 02557

  Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 403-9601

  47 Winemack St, Oak Bluffs, MA 02557
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  /30

  $20,000 per month plus fees

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
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  /41

  $1,310,000 Sold Aug 18, 2025

  • 1,964 Sq Ft
  • $667/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  35 E Side Rd, Oak Bluffs, MA 02557

  Close to the Lagoon - This three-bedroom, two-bath home sits on an oversized corner lot and has been lovingly maintained over the years. Recent upgrades include the addition of mini splits, interior painting, and lighting. The sunroom provides additional year-round living space and the wraparound deck is ideal for summer use. Bring your vision to the partially finished lower level where

  Kristin Buck Donnelly + Co

  35 E Side Rd, Oak Bluffs, MA 02557
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  /13

  Est $1,256,744 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  33 Menahan St, Vineyard Haven, MA 02568

  33 Menahan St, Vineyard Haven, MA 02568
• 

  

  /40

  $1,825,000

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

  Nora Jardin Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
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  /14

  $14,200 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
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  /36

  $1,765,000 Sold Aug 18, 2025

  • 2,450 Sq Ft
  • $720/SF
  • 25 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1988

  34 Tower Ridge Rd, Oak Bluffs, MA 02568

  Nestled on a beautifully landscaped lot with lush gardens and mature trees, 34 Tower Ridge offers the perfect blend of privacy and convenience. Ideally located just minutes from downtown Oak Bluffs and the Farm Neck Golf Course, this well-maintained property is suited for comfortable year-round living or as a serene Island retreat. Inside, the bright and open layout features an updated kitchen

  Katie Donahue Sandpiper Realty

  34 Tower Ridge Rd, Oak Bluffs, MA 02568
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  /14

  Est $995,457 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Manchester Ave, Vineyard Haven, MA 02568

  51 Manchester Ave, Vineyard Haven, MA 02568
• 

  

  /46

  $1,795,000

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  17 John Wesley Ave, Vineyard Haven, MA 02568

  Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

  kyle Neyer Tea Lane Associates

  17 John Wesley Ave, Vineyard Haven, MA 02568
• 

  

  /15

  $21,000 per month plus fees

  • 6 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • House for Rent

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

  Karen Overtoom Karen M. Overtoom R.E.

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
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  /4

  $1,350,000 Sold Aug 15, 2025

  • 1,864 Sq Ft
  • $724/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  Charming Home Steps from Lagoon Pond - This three bedroom, two bath home is just 550 feet from the sandy shores and calm waters of Lagoon Pond, perfect for swimming, boating and shell fishing. Ideal for both year-round living or vacationing, the home offers an open floor plan, a private primary suite with a walk-in closet and en-suite bath, two guest bedrooms plus a den/office. The finished

  Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
• 

  

  /31

  Est $1,466,046 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568

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