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Oak Bluffs Homes for Sale

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

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 348-7972

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /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

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 456-5742

    70 Carol Ln, Oak Bluffs, MA 02557
  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /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

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 403-9601

    47 Winemack St, Oak Bluffs, MA 02557
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /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

    Agent Photo

    Alice Pierce

    Coldwell Banker Realty - Hingham

    (508) 715-6242

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • 385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    /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

    Agent Photo

    Wendy Harman

    Compass

    (508) 205-8817

    385 Barnes Rd, Vineyard Haven, MA 02568
  • 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    /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

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    /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

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 422-4131

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • 6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    /34

    $3,450,000

    • 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
  • 44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    /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
  • 17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley 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
  • 35 Tower Ridge Rd, Oak Bluffs, MA 02557
    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    /42

    $1,895,000

    • 3 Beds
    • 4 Baths
    • 2,558 Sq Ft

    35 Tower Ridge Rd, Oak Bluffs, MA 02557

    Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

    Katherine Donahue Sandpiper Realty Inc

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
  • 50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, Edgartown, MA 02539
    /46

    $2,395,000

    • 5 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • 5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    /46

    $1,800,000

    • 4 Beds
    • 2.5 Baths
    • 2,127 Sq Ft

    5 Bayes Hill Cir, Vineyard Haven, MA 02568

    Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with

    Rene Jackson Island Real Estate

    5 Bayes Hill Cir, Vineyard Haven, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /26

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 11 Beach Rd, Oak Bluffs, MA 02557
    11 Beach Rd, Oak Bluffs, MA 02557
    11 Beach Rd, Oak Bluffs, MA 02557
    /23

    $1,790,000

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    11 Beach Rd, Oak Bluffs, MA 02557

    Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

    Alan Schweikert Ocean Park Realty Inc

    11 Beach Rd, Oak Bluffs, MA 02557
  • 16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    /39

    $2,495,000

    • 5 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    16 Atlantic Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

    Katherine Donahue Sandpiper Realty Inc

    16 Atlantic Ave, Oak Bluffs, MA 02557
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /44

    $2,699,000

    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    Motivated Seller!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    /19

    $2,295,000

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft

    71 Netock Ave, Oak Bluffs, MA 02557

    On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

    Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
  • 4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    /30

    $2,195,000

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

    4 Dempster Park, Oak Bluffs, MA 02568

    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. First 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 the rear patio.

    Perry Patterson MV Luxury Homes LLC

    4 Dempster Park, Oak Bluffs, MA 02568
  • 22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    /37

    $2,240,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02557

    Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

    Jennifer O'hanlon Compass

    22 Greenleaf Ave, Oak Bluffs, MA 02557
  • 22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    /39

    $2,240,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02539

    Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

    Jen O'Hanlon Compass | The O'Hanlon Group

    22 Greenleaf Ave, Oak Bluffs, MA 02539
  • 79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    /64

    $2,100,000

    • 4 Beds
    • 4 Baths
    • 3,076 Sq Ft

    79 Circuit Ave, Oak Bluffs, MA 02557

    Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities

    kyle Neyer Tea Lane Associates

    79 Circuit Ave, Oak Bluffs, MA 02557
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    /24

    $2,195,000

    • 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
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /24

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co.

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 23 Laurel Ave, Oak Bluffs, MA 02557
    23 Laurel Ave, Oak Bluffs, MA 02557
    23 Laurel Ave, Oak Bluffs, MA 02557
    /25

    $1,500,000

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft

    23 Laurel Ave, Oak Bluffs, MA 02557

    LOCATION! YEAR ROUND HOUSE!INVESTMENT PROPERTY!STARTER HOME!A comfortable home in an established, East Chop neighborhood, this four bedroom, two bathroom house is located within walking distance to the Harbor, downtown Oak Bluffs, and the Oak Bluffs Ferries. There is easy access to shops, family entertainment, and the beach. This home provides a welcoming porch and a spacious backyard patio

    Sandra Grymes Martha's Vineyard Island-Wide Realty

    23 Laurel Ave, Oak Bluffs, MA 02557
  • 9 Grovedale Rd, Oak Bluffs, MA 02557
    9 Grovedale Rd, Oak Bluffs, MA 02557
    9 Grovedale Rd, Oak Bluffs, MA 02557
    /28

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,637 Sq Ft

    9 Grovedale Rd, Oak Bluffs, MA 02557

    Welcome to a home full of character and charm in the heart of Oak Bluffs. This 3-bedroom, 2-bathroom property offers comfortable living with a sun-filled open kitchen and dining area featuring a picturesque bay window that flows seamlessly into a warm living room centered around a welcoming fireplace. Just a short distance from the Lagoon, the setting is enhanced by mature plantings that surround

    Bonnie Pierce Wallace & Co. Sotheby's

    9 Grovedale Rd, Oak Bluffs, MA 02557
  • 8 Hitchings Cir, Oak Bluffs, MA 02557
    8 Hitchings Cir, Oak Bluffs, MA 02557
    8 Hitchings Cir, Oak Bluffs, MA 02557
    /11

    $915,000

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

    8 Hitchings Cir, Oak Bluffs, MA 02557

    Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

    Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
  • 26 Winne Ave, Vineyard Haven, MA 02568
    26 Winne Ave, Vineyard Haven, MA 02568
    26 Winne Ave, Vineyard Haven, MA 02568
    /39

    $1,470,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    26 Winne Ave, Vineyard Haven, MA 02568

    Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

    Joe & Nicole Holland Vineyard Dream Realty LLC

    26 Winne Ave, Vineyard Haven, MA 02568
  • 41 Trinity Park, Oak Bluffs, MA 02557
    41 Trinity Park, Oak Bluffs, MA 02557
    41 Trinity Park, Oak Bluffs, MA 02557
    /19

    $795,000

    • 4 Beds
    • 1 Bath
    • 1,154 Sq Ft

    41 Trinity Park, Oak Bluffs, MA 02557

    Step back in time with this quintessential Martha’s Vineyard Campground Cottage, nestled in the heart of Wesleyan Grove. The cottage captures the spirit of the Island’s rich history, with its storybook architecture, vibrant community setting, and proximity to all that Oak Bluffs has to offer. The cottage features classic Victorian-era details, starting with its inviting front porch. The

    Stacy Ickes Donnelly + Co

    41 Trinity Park, Oak Bluffs, MA 02557
  • 16 Cottage Park, Oak Bluffs, MA 02557
    16 Cottage Park, Oak Bluffs, MA 02557
    16 Cottage Park, Oak Bluffs, MA 02557
    /33

    $839,000

    • 2 Beds
    • 1 Bath
    • 954 Sq Ft

    16 Cottage Park, Oak Bluffs, MA 02557

    Just steps from the iconic Tabernacle and Trinity Park, this charming cottage is nestled in the heart of the historic Martha's Vineyard Camp Meeting Association--a designated National Historic Landmark District. Surrounded by colorful gardens and picturesque pedestrian walkways, it offers an easy stroll to Oak Bluffs Harbor, beaches, ferries, art galleries, restaurants, and all the vibrant charm

    Marilyn Moses Ocean Park Realty, Inc.

    16 Cottage Park, Oak Bluffs, MA 02557
  • 25 Ice Pond Ln Unit 43, Oak Bluffs, MA 02568
    25 Ice Pond Ln Unit 43, Oak Bluffs, MA 02568
    25 Ice Pond Ln Unit 43, Oak Bluffs, MA 02568
    /7

    $1,750,000

    • Land
    • 3.08 Acres
    • $568,182 per Acre

    25 Ice Pond Ln Unit 43, Oak Bluffs, MA 02568

    FARM NECK LOT FOR SALE *This land is in CONSERVATION AND UNBUILDABLE. Ownership of this lot grants you Stockholder Membership at Farm Neck Golf Club with Farm Neck approval— a true jewel of Martha’s Vineyard. The current waiting list to join spans 12–15 years. Enjoy the Farm Neck lifestyle and a championship-caliber, semi-private golf club that includes tennis facilities, an association dock on

    Tina Miller Donnelly + Co

    25 Ice Pond Ln Unit 43, Oak Bluffs, MA 02568
  • 25 Ice Pond Ln, Oak Bluffs, MA 02568
    25 Ice Pond Ln, Oak Bluffs, MA 02568
    25 Ice Pond Ln, Oak Bluffs, MA 02568
    /7

    $1,750,000

    • Land
    • 3.08 Acres
    • $568,182 per Acre

    25 Ice Pond Ln, Oak Bluffs, MA 02568

    FARM NECK LOT FOR SALE *This land is in CONSERVATION AND UNBUILDABLE. Ownership of this lot grants you Stockholder Membership at Farm Neck Golf Club with Farm Neck approval— a true jewel of Martha’s Vineyard. The current waiting list to join spans 12–15 years. Enjoy the Farm Neck lifestyle and a championship-caliber, semi-private golf club that includes tennis facilities, an association dock on

    Tina Miller Donnelly + Co.

    25 Ice Pond Ln, Oak Bluffs, MA 02568
  • 8 Paddock Rd, Oak Bluffs, MA 02557
    8 Paddock Rd, Oak Bluffs, MA 02557
    8 Paddock Rd, Oak Bluffs, MA 02557
    /47

    $5,450,000

    • 4 Beds
    • 5.5 Baths
    • 3,300 Sq Ft

    8 Paddock Rd, Oak Bluffs, MA 02557

    Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

    Lesley Heidt Sandpiper Realty Inc

    8 Paddock Rd, Oak Bluffs, MA 02557
  • 50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568
    50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568
    50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568
    /25

    $2,595,000

    • Land
    • 7.75 Acres
    • $334,839 per Acre

    50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568

    Nestled beside the beloved Island Alpaca Farm, this rare 7.75-acre parcel offers an exceptional blend of open space, agricultural use, and development potential. Approximately 4.38 acres are protected by a conservation restriction, allowing for limited farming and equestrian activities—perfect for those seeking a pastoral lifestyle. The remaining 3.37 acres provide a prime opportunity to build

    Trish Lyman Compass | Point B

    50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568
  • 60 -R Carol Ln, Oak Bluffs, MA 02557
    60 -R Carol Ln, Oak Bluffs, MA 02557
    60 -R Carol Ln, Oak Bluffs, MA 02557
    /15

    $845,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60 -R Carol Ln, Oak Bluffs, MA 02557

    Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

    Sheila Morse Island Real Estate

    60 -R Carol Ln, Oak Bluffs, MA 02557
  • 60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    /14

    $845,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60R Carol Ln, Oak Bluffs, MA 02557

    Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

    Nora Jardin Island Real Estate

    60R Carol Ln, Oak Bluffs, MA 02557
  • 170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    /28

    $1,325,000

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    170 Barnes Rd, Oak Bluffs, MA 02557

    Calling water and boating enthusiasts. Solid Cape-style home one block from Sailing Camp Park, water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

    Christine Rose Martha's Vineyard Island-Wide Realty

    170 Barnes Rd, Oak Bluffs, MA 02557
  • 50 Iron Hill Rd, Oak Bluffs, MA 02568
    50 Iron Hill Rd, Oak Bluffs, MA 02568
    50 Iron Hill Rd, Oak Bluffs, MA 02568
    /13

    $2,595,000

    • Land
    • 7.75 Acres
    • $334,839 per Acre

    50 Iron Hill Rd, Oak Bluffs, MA 02568

    This rare 7.75-acre parcel offers a unique combination of open space and development potential. Approximately 4.38 acres are protected by a conservation restriction, allowing for limited farming and equestrian use—ideal for those seeking pastoral pursuits. The remaining 3.37 acres offers the potential to build your dream home- while simply enjoying Island Life. The property features two barns

    Patricia Lyman Compass

    50 Iron Hill Rd, Oak Bluffs, MA 02568
  • 37 Double Ox Rd, Oak Bluffs, MA 02557
    37 Double Ox Rd, Oak Bluffs, MA 02557
    37 Double Ox Rd, Oak Bluffs, MA 02557
    /8

    $649,000

    • Land
    • 0.29 Acre
    • $2,237,931 per Acre

    37 Double Ox Rd, Oak Bluffs, MA 02557

    This is your opportunity to get in on the ground floor of Lagoon Ridge, a stunning, new development. Several homes are already in place. This beautiful, wooded Lot is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation lands. All utility

    Lynn Buder Sandpiper Realty Inc

    37 Double Ox Rd, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 3

Massachusetts Dukes County Marthas Vineyard Oak Bluffs

Real Estate & Homes for Sale in Oak Bluffs, Marthas Vineyard

Why Live in 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.
Learn more about living in Oak Bluffs

Frequently Asked Questions

Is Oak Bluffs a good place to live?
Oak Bluffs is a good place to live. Oak Bluffs is considered very car-dependent and somewhat bikeable. Oak Bluffs has 5 parks for recreational activities. It is sparse in population with 1.6 people per acre and a median age of 49. The average household income is $133,511 which is above the national average. College graduates make up 46.9% of residents. A majority of residents in Oak Bluffs are home owners, with 26.7% of residents renting and 73.3% of residents owning their home. A local real estate agent serving Oak Bluffs can help you decide if this neighborhood is the right one for you. Learn more on our Oak Bluffs neighborhood guide.
How much do you need to make to afford a house in Oak Bluffs?
The median home price in Oak Bluffs is $1,550,000. If you put a 20% down payment of $310,000 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $7,720 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $331K a year to afford the median home price in Oak Bluffs. The average household income in Oak Bluffs is $134K.
What are the best public schools in Oak Bluffs?
The best public schools that serve Oak Bluffs are:
What are the best private schools in Oak Bluffs?
The best private schools that serve Oak Bluffs are:
What are the most popular zip codes in Oak Bluffs, Marthas Vineyard, MA?
The most popular zip codes in Oak Bluffs, Marthas Vineyard, MA include 02568, 02536, 02539, 02575 and 02535.
What are the most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA?
The most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA are Vineyard Haven, Edgartown, West Tisbury, Falmouth Village and Chilmark.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 103 days on the market compared to the national average of 52 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,295,000, up 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,295,000
Median Single Family Sale Price
$1,590,000
Median 2 Bedroom Sale Price
$1,490,000
Median 1 Bedroom Sale Price
$1,495,000
Average Price Per Sq Ft
$1,107
Number of Homes for Sale
66
Last 12 months Home Sales
136
Months of Supply
5.80
Median List Price
$1,550,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
15%
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