20

Oak Bluffs Houses for Sale

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  • /32

    $2,285,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    4 Dempster Park, Oak Bluffs, MA 02568

    East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. The 1st floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to

    Perry Patterson MV Luxury Homes, LLC

    4 Dempster Park, Oak Bluffs, MA 02568
  • /40

    $4,500,000

    • 3 Beds
    • 5.5 Baths
    • 4,046 Sq Ft

    267 Barnes Rd, Oak Bluffs, MA 02557

    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 water views 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,

    Stephanie Roache Donnelly + Co.

    267 Barnes Rd, Oak Bluffs, MA 02557
  • /60

    $3,500,000

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    Picture yourself in this beautifully designed custom home offering the ultimate in privacy. The first floor has an open floor plan which includes the dining room, kitchen, wet bar, and living space. Bypass siding doors separate the living space from the dining and kitchen. Experience the ultimate in culinary luxury with a gourmet kitchen featuring custom cabinets, high end appliances, and ample

    Casandra Hyland Landmarks at TODAY Real Estate

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
  • /42

    $2,495,000

    • 3 Beds
    • 4.5 Baths
    • 3,200 Sq Ft

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

    Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

    Jennifer B. DaSilva Compass

    6 Martha's Park Rd, Oak Bluffs, MA 02557
  • /28

    $3,500,000

    • 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

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • /59

    $4,950,000

    • 5 Beds
    • 5.5 Baths
    • 2,651 Sq Ft

    31 Old Harbor Ln, Oak Bluffs, MA 02557

    Enjoy spectacular views of Sengekontacket Pond and State Beach all the way to Chappaquiddick from this newly constructed home that has been only lightly used in the 3 years since it was built. There are also beautiful views of the third, fourth and fifth holes at Farm Neck Golf Club. The fresh and bright home was built by top-notch Stedman Construction and is set on the largest lot in Waterview

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    31 Old Harbor Ln, Oak Bluffs, MA 02557
  • /24

    $2,375,000

    • 4 Beds
    • 3 Baths
    • 2,262 Sq Ft

    30 Sengekontacket Rd, Oak Bluffs, MA 02557

    Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

    Cassie Bradley Wallace & Co. Sotheby's International Realty

    30 Sengekontacket Rd, Oak Bluffs, MA 02557
  • /23

    $2,495,000

    • 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

    Brian Smith Portfolio Real Estate Inc.

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • /34

    $1,895,000

    • 5 Beds
    • 2 Baths
    • 1,918 Sq Ft

    35 Tuckernuck Ave, Oak Bluffs, MA 02557

    Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience.As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a generous

    Jennifer B. DaSilva Compass

    35 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /9

    $975,000

    • 1 Bed
    • 2 Baths
    • 1,000 Sq Ft

    128 Manchester Ave, Oak Bluffs, MA 02568

    This delightful, modern cape-style home features thoughtful and impressive finish details. It is almost ready for move in day! The covered porch welcomes you into the home where you will find a well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, a French-door refrigerator, dishwasher, and back splash finished with subway tiles. There is an

    Michele Moore Island Real Estate

    128 Manchester Ave, Oak Bluffs, MA 02568
  • /18

    $1,050,000

    • 1 Bed
    • 2 Baths
    • 1,401 Sq Ft

    249 County Rd, Oak Bluffs, MA 02557

    This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy

    Katherine Donahue Sandpiper Realty Inc

    249 County Rd, Oak Bluffs, MA 02557
  • /39

    $10,500,000

    • 8 Beds
    • 6 Baths
    • 3,888 Sq Ft

    47 E Chop Dr, Oak Bluffs, MA 02568

    East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr, Oak Bluffs, MA 02568
  • /17

    $1,169,999

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    96 Manchester Ave, Oak Bluffs, MA 02557

    Nestled in the sought-after Lagoon Heights in Oak Bluffs, 96 Manchester Ave is a charming Cape-style home offering a perfect blend of comfort and coastal charm. This well-maintained residence features three spacious bedrooms and two bathrooms. Recent updates enhance both style and functionality, including a new roof, numerous Andersen windows, an outdoor shower, and fresh interior paint. The

    Jordan Pavao Keller Williams South Watuppa

    96 Manchester Ave, Oak Bluffs, MA 02557
  • /17

    $749,000

    • 3 Beds
    • 1 Bath
    • 725 Sq Ft

    2 Fisk Ave, Oak Bluffs, MA 02557

    Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

    Julie Walker Century 21 North East

    2 Fisk Ave, Oak Bluffs, MA 02557
  • /33

    $1,690,000

    • 4 Beds
    • 3.5 Baths
    • 2,336 Sq Ft

    8 Schoolhouse Village, Oak Bluffs, MA 02557

    Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors

    Stephanie Roache Donnelly + Co.

    8 Schoolhouse Village, Oak Bluffs, MA 02557
  • /17

    $1,250,000

    • 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. With a large open kitchen, dining area, and living room with plenty of room for a large gatherings. The primary bedroom has a bathroom ensuite. Another bedroom has easy access to the hall bath. The finished basement could have an

    Lisa Lucier Anchor Realty of MV

    70 Carol Ln, Oak Bluffs, MA 02557
  • /17

    $995,000

    • 2 Beds
    • 0.5 Baths
    • 952 Sq Ft

    50 Canonicus Ave, Oak Bluffs, MA 02557

    Coming Soon! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to beach,

    Michele Moore Island Real Estate

    50 Canonicus Ave, Oak Bluffs, MA 02557
  • /18

    $1,449,000

    • 3 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    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
  • /76

    $13,200,000

    • 8 Beds
    • 9 Baths
    • 8,170 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02568

    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

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    150 E Chop Dr, Oak Bluffs, MA 02568
  • /28

    $10,500,000

    • 7 Beds
    • 6 Baths
    • 3,888 Sq Ft

    47 E Chop Dr, Oak Bluffs, MA 02568

    East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular water views, dock with 9 slips, and just steps from beaches, tennis club, downtown and ferries to mainland! Property has been extensively renovated recently. Uses include -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion,2.) Currently

    Perry Patterson MV Luxury Homes LLC

    47 E Chop Dr, Oak Bluffs, MA 02568

About Oak Bluffs

Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses and historical significance as a summer haven for Black Americans. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.

Home Trends in Oak Bluffs, MA

Home Trends

Median Price (12 Mo)
$1,162,500
Median Single Family Price
$1,325,000
Median 2 Bedroom Price
$925,000
Median 1 Bedroom Price
$935,000
Average Price Per Sq Ft
$956
Number of Homes for Sale
22
Last 12 months Home Sales
59
Months of Supply
4.50
Median List Price
$1,400,000
Median Discount From 1st List Price
6%
Median Home Sale Price YoY Change
-16%
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