102

Homes for Sale in 02568

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  • 33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    /12

    $1,495,000 Open Sun 12PM - 3PM

    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    (508) 687-6441

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • 6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    /34

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    6 Brewster Ave, Oak Bluffs, MA 02557

    Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

    Katherine Donahue Sandpiper Realty Inc

    6 Brewster Ave, Oak Bluffs, MA 02557
  • 23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    /29

    $2,600,000

    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views.Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound—a setting that captures the

    Rene Ben David Ocean Park Realty Inc

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
  • 151 Tashmoo Ave, Vineyard Haven, MA 02568
    151 Tashmoo Ave, Vineyard Haven, MA 02568
    151 Tashmoo Ave, Vineyard Haven, MA 02568
    /28

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 2,690 Sq Ft

    151 Tashmoo Ave, Vineyard Haven, MA 02568

    The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

    Brenda Galligan Karen M. Overtoom R.E.

    151 Tashmoo Ave, Vineyard Haven, MA 02568
  • 4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    /23

    $2,260,000

    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • 378 State Rd, Vineyard Haven, MA 02568
    378 State Rd, Vineyard Haven, MA 02568
    378 State Rd, Vineyard Haven, MA 02568
    /25

    $1,950,000

    • 2 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    378 State Rd, Vineyard Haven, MA 02568

    MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT - Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with strong income-producing potential.The first floor offers four offices including a reception area, 1.5 baths, and a

    Lesley Heidt Sandpiper Realty Inc

    378 State Rd, Vineyard Haven, MA 02568
  • 81 Leland Ave, Vineyard Haven, MA 02568
    81 Leland Ave, Vineyard Haven, MA 02568
    81 Leland Ave, Vineyard Haven, MA 02568
    /46

    $1,975,000

    • 3 Beds
    • 2.5 Baths
    • 1,902 Sq Ft

    81 Leland Ave, Vineyard Haven, MA 02568

    Close to town with exceptional indoor / outdoor flow & privacy.Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor

    Jill Napior Tea Lane Associates

    81 Leland Ave, Vineyard Haven, MA 02568
  • 241 Daggett Ave, Vineyard Haven, MA 02568
    241 Daggett Ave, Vineyard Haven, MA 02568
    241 Daggett Ave, Vineyard Haven, MA 02568
    /39

    $3,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,068 Sq Ft

    241 Daggett Ave, Vineyard Haven, MA 02568

    Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    241 Daggett Ave, Vineyard Haven, MA 02568
  • 34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    34 Davis St, Tisbury, MA 02568
    /26

    $1,999,000

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft

    34 Davis St, Tisbury, MA 02568

    NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

    Andrew McElhinney Compass Massachusetts, LLC

    34 Davis St, Tisbury, MA 02568
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /24

    $1,999,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    /9

    $2,250,000

    • 3 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    35 Double Ox Rd, Oak Bluffs, MA 02557

    Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd, Oak Bluffs, MA 02557
  • 61 Causeway Rd, Vineyard Haven, MA 02568
    61 Causeway Rd, Vineyard Haven, MA 02568
    61 Causeway Rd, Vineyard Haven, MA 02568
    /58

    $2,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,530 Sq Ft

    61 Causeway Rd, Vineyard Haven, MA 02568

    Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience.

    Stephanie Roache Donnelly + Co

    61 Causeway Rd, Vineyard Haven, MA 02568
  • 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /42

    $2,150,000

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • 70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    /67

    $2,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    70 Spring St, Vineyard Haven, MA 02568

    Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

    June Flake Viewpoints

    70 Spring St, Vineyard Haven, MA 02568
  • 33 Ocean Ave, Oak Bluffs, MA 02557
    33 Ocean Ave, Oak Bluffs, MA 02557
    33 Ocean Ave, Oak Bluffs, MA 02557
    /30

    $2,950,000

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft

    33 Ocean Ave, Oak Bluffs, MA 02557

    A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

    Marcia Sullivan Garvey Donnelly + Co.

    33 Ocean Ave, Oak Bluffs, MA 02557
  • 21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    /32

    $560,000

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

    Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

    Diana Gilmore Island Real Estate

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
  • 25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /28

    $950,000

    • 2 Beds
    • 2 Baths
    • 1,583 Sq Ft

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

    Maranda Post Compass | The O'Hanlon Group

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    /36

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    4 Canonicus Ave, Oak Bluffs, MA 02557
  • 0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $625,000

    • Land
    • 0.34 Acre
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    /43

    $14,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Thomas Wallace Wallace & Co. Sotheby's

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • 11 Macs Ln, Tisbury, MA 02568
    11 Macs Ln, Tisbury, MA 02568
    11 Macs Ln, Tisbury, MA 02568
    /7

    $4,500,000

    • 15 Beds
    • 12.5 Baths
    • 7,250 Sq Ft

    11 Macs Ln, Tisbury, MA 02568

    A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    11 Macs Ln, Tisbury, MA 02568
  • 33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    /19

    $10,500,000

    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • 22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
    /30

    $1,595,000

    • 5 Beds
    • 3 Baths
    • 1,810 Sq Ft

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568

    Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical,

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
  • 51 Lantern Ln, Vineyard Haven, MA 02568
    51 Lantern Ln, Vineyard Haven, MA 02568
    51 Lantern Ln, Vineyard Haven, MA 02568
    /15

    $835,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    51 Lantern Ln, Vineyard Haven, MA 02568

    Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    51 Lantern Ln, Vineyard Haven, MA 02568
  • 124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    /15

    $610,000

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

    MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

    Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
  • 26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    /49

    $849,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    26 Winthrop Ave, Oak Bluffs, MA 02557

    Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    26 Winthrop Ave, Oak Bluffs, MA 02557
  • 40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    /36

    $1,390,000

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft

    40 Scotchmans Ln, Vineyard Haven, MA 02568

    A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

    Jim Osmundsen Donnelly + Co.

    40 Scotchmans Ln, Vineyard Haven, MA 02568
  • 43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    /31

    $5,995,000

    • 3 Beds
    • 3 Baths
    • 2,234 Sq Ft

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

    Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

    Peyton Wallace Studio Realty

    43 Sengekontacket Rd, Oak Bluffs, MA 02557
  • 4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /9

    $1,395,000

    • 0.5 Baths
    • 1,283 Sq Ft

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

    Jarrett Hurwitz Keller Williams Realty

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • 7 Highland Ave, Vineyard Haven, MA 02568
    7 Highland Ave, Vineyard Haven, MA 02568
    7 Highland Ave, Vineyard Haven, MA 02568
    /4

    $809,000

    • Land
    • 0.39 Acre
    • $2,074,359 per Acre

    7 Highland Ave, Vineyard Haven, MA 02568

    ''Rare opportunity in East Chop. Buildable lot in a beautiful wooded area, walking distance to town, beach, and ferries. Secluded yet accessible.

    Shera Toledo eXp Realty, LLC

    7 Highland Ave, Vineyard Haven, MA 02568
  • 22 Montgomery Square, Oak Bluffs, MA 02557
    22 Montgomery Square, Oak Bluffs, MA 02557
    22 Montgomery Square, Oak Bluffs, MA 02557
    /21

    $895,000

    • 3 Beds
    • 1 Bath
    • 931 Sq Ft

    22 Montgomery Square, Oak Bluffs, MA 02557

    COMING SOON 3/13 along with new photos..Located in the heart of Wesleyan Grove within the historic Martha's Vineyard Camp Meeting Association, this enchanting year-round Victorian cottage captures the timeless charm and vibrant spirit of Oak Bluffs living. Just steps from lively Circuit Avenue, picturesque Oak Bluffs Harbor, and sandy beaches, the location offers the very best of in-town

    Marilyn Moses Ocean Park Realty, Inc.

    22 Montgomery Square, Oak Bluffs, MA 02557
  • 22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    22 Oklahoma Ave, Vineyard Haven, MA 02568
    /21

    $1,445,000

    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • 24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    /3

    $857,000

    • Land
    • 0.39 Acre
    • $2,209,902 per Acre

    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

    OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time.

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
  • 7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    /28

    $1,799,000

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    Meadowview Farms -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

    Lesley Heidt Sandpiper Realty Inc

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
  • 33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    33 Alyssa Ln, Vineyard Haven, MA 02568
    /12

    $1,495,000 Open Sun 12PM - 3PM

    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

    Stephanie Burke Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • 12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    /54

    $1,830,000

    • 4 Beds
    • 4 Baths
    • 1,600 Sq Ft

    12 & 14 Maple Ave, Oak Bluffs, MA 02557

    Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

    Leslie Floyd Portfolio Properties

    12 & 14 Maple Ave, Oak Bluffs, MA 02557
  • 25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    /4

    $1,100,000

    • Land
    • 1 Acre
    • $1,100,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    Per the BOH, this property can accommodate a 3 bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studioProperty is not serviced by a well or septic system. Buyer is responsible for obtaining permits and installation.Association Dues $650.00

    Casandra Hyland Sandpiper Realty, Inc.

    25 Coffins Field Rd, Edgartown, MA 02539
  • 28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    /30

    $999,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    28 Barling Ave, Vineyard Haven, MA 02568

    Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

    Michael Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • 96 Dunham Ave, Vineyard Haven, MA 02568
    96 Dunham Ave, Vineyard Haven, MA 02568
    96 Dunham Ave, Vineyard Haven, MA 02568
    /35

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    96 Dunham Ave, Vineyard Haven, MA 02568

    This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land. The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has

    Peter Cronig Cronigs Real Estate

    96 Dunham Ave, Vineyard Haven, MA 02568
  • 103 Meadow View Rd, Oak Bluffs, MA 02557
    103 Meadow View Rd, Oak Bluffs, MA 02557
    103 Meadow View Rd, Oak Bluffs, MA 02557
    /26

    $1,750,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft

    103 Meadow View Rd, Oak Bluffs, MA 02557

    Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

    Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557

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