319

Homes for Sale near Martha's Vineyard Regional High School

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  • 48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    /9

    $1,399,000

    • 3 Beds
    • 3 Baths
    • 1,959 Sq Ft

    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539

    This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3-bedroom, 3-bathroom property checks all the boxes. With numerous bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval), this is a truly exceptional

    Mavis Francis eXp Realty

    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
  • 48 W Tisbury Rd, Edgartown, MA 02539
    48 W Tisbury Rd, Edgartown, MA 02539
    48 W Tisbury Rd, Edgartown, MA 02539
    /8

    $1,350,000

    • 3 Beds
    • 3 Baths
    • 1,959 Sq Ft

    48 W Tisbury Rd, Edgartown, MA 02539

    This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3 bedrooms, 3 bathrooms property checks all the boxes. With lots of bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval) this is a truly exceptional find.

    Mavis Francis eXp Realty

    48 W Tisbury Rd, Edgartown, MA 02539
  • 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
  • 7 Clay Pit Ln, Aquinnah, MA 02535
    7 Clay Pit Ln, Aquinnah, MA 02535
    7 Clay Pit Ln, Aquinnah, MA 02535
    /28

    $7,450,000

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    7 Clay Pit Ln, Aquinnah, MA 02535

    Stunning waterfront home with panoramic waterviews. The home was designed by Hutker Associates, built by Andrew Flake, and landscaped by Michael Van Valkenburgh - three of the most renowned names in Martha's Vineyard home creation. Little wonder it was featured on the cover of Beautiful Home magazine and has been included in several other home design magazines and books. The 5000 sq ft house

    Mark Jenkins Wallace & Co. Sotheby's

    7 Clay Pit Ln, Aquinnah, MA 02535
  • 825 Main St, Vineyard Haven, MA 02568
    825 Main St, Vineyard Haven, MA 02568
    825 Main St, Vineyard Haven, MA 02568
    /46

    $14,500,000

    • 6 Beds
    • 5 Baths
    • 4,964 Sq Ft

    825 Main St, Vineyard Haven, MA 02568

    Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

    Judy Federowicz Landmarks at TODAY Real Estate

    825 Main St, Vineyard Haven, MA 02568
  • 24 Katama Bay View Rd, Edgartown, MA 02539
    24 Katama Bay View Rd, Edgartown, MA 02539
    24 Katama Bay View Rd, Edgartown, MA 02539
    /26

    $8,500,000

    • 4 Beds
    • 6 Baths
    • 3,497 Sq Ft

    24 Katama Bay View Rd, Edgartown, MA 02539

    This classic New England waterview home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    24 Katama Bay View Rd, Edgartown, MA 02539
  • 56 N Neck Rd, Edgartown, MA 02539
    56 N Neck Rd, Edgartown, MA 02539
    56 N Neck Rd, Edgartown, MA 02539
    /51

    $3,995,000

    • 4 Beds
    • 4 Baths
    • 4,920 Sq Ft

    56 N Neck Rd, Edgartown, MA 02539

    A RARE CHAPPAQUIDDICK LEGACY ESTATE -- Privacy & Island Living at its finest. Step into a world where time slows, ocean breezes carry the scent of salt and cedar, and each day begins and ends with the relaxing sounds of the local fauna and the Vineyard Sound. This 18.4-acre multi-residence estate, with 4 conforming parcels, on Martha's Vineyard's treasured Chappaquiddick Island is more than a

    Leslie Floyd Portfolio Properties

    56 N Neck Rd, Edgartown, MA 02539
  • 15 Night Heron Rd, Edgartown, MA 02539
    15 Night Heron Rd, Edgartown, MA 02539
    15 Night Heron Rd, Edgartown, MA 02539
    /76

    $2,345,000

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    15 Night Heron Rd, Edgartown, MA 02539

    KATAMA - NEWLY RENOVATED! This Quintessential Martha’s Vineyard saltbox blends timeless island character with wonderful thoughtful updates, having been recently renovated. Set in a quiet location, Island Grove, one of the most popular locations in Edgartown, you're just a short drive to Wilson's Landing, South Beach and downtown Edgartown, an ideal location for summer escapes, year-round living,

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    15 Night Heron Rd, Edgartown, MA 02539
  • 0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
    /10

    $619,000

    • Land
    • 0.61 Acre
    • $1,014,754 per Acre

    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568

    Vacant Land - NO LIMIT on bedroom count! You just have to meet setbacks. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy the peace of a rural setting, yet remain conveniently close to the ferry

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

    0 Red Buoy Ln Unit Lot 147 32500278, Tisbury, MA 02568
  • 3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
    3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
    3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
    /13

    $4,950,000

    • Land
    • 14.4 Acres
    • $343,750 per Acre

    3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539

    Build your dream home or homes on the special 14+ acre private wooded lot surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates. BWA amenities also

    Robert Kenney Tea Lane Associates

    3 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
  • 16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    /44

    $4,695,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    16 Frog Hollow, Vineyard Haven, MA 02568

    Timeless Water View Home on Vineyard Haven Harbor. Nestled between historic Main Street and the exclusivity of West Chop, this property combines private coastal living with access to the best of Vineyard Haven. With access to the calm waters of the Harbor, the residence sits at the edge of a sweeping meadow with uninterrupted water views. Built in 2015 the three-bedroom, two-bathroom home is a

    Rose Ryley Sandpiper Realty Inc

    16 Frog Hollow, Vineyard Haven, MA 02568
  • 10 Putnam Way, Vineyard Haven, MA 02568
    10 Putnam Way, Vineyard Haven, MA 02568
    10 Putnam Way, Vineyard Haven, MA 02568
    /7

    $700,000

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft

    10 Putnam Way, Vineyard Haven, MA 02568

    Raised ranch style house on a corner lot near the lagoon. This could be the ''fixer upper'' buyers always ask about. Location is in the Lagoon Pond watershed and BUYER will have to replace the septic system to bring up to latest environmental requirements.

    Kathleen Dawson Donnelly + Co.

    10 Putnam Way, Vineyard Haven, MA 02568
  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $4,250,000

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • 58 Road To the Plains, Edgartown, MA 02539
    58 Road To the Plains, Edgartown, MA 02539
    58 Road To the Plains, Edgartown, MA 02539
    /42

    $1,750,000

    • 4 Beds
    • 2 Baths
    • 1,342 Sq Ft

    58 Road To the Plains, Edgartown, MA 02539

    KATAMA BEACH HOUSE - This turnkey Katama retreat blends coastal charm with modern comfort, offering a rare combination of location, amenities, and style. A 19-foot heated swim spa with current, and beautiful wooden deck, lets you swim year-round or unwind in the attached Jacuzzi. The property comes fully furnished, making it an effortless purchase, and boasts a strong rental history for

    Dawn Bellante-Holand Sandpiper Realty

    58 Road To the Plains, Edgartown, MA 02539
  • 67 12th St S, Edgartown, MA 02539
    67 12th St S, Edgartown, MA 02539
    67 12th St S, Edgartown, MA 02539
    /24

    $1,049,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    67 12th St S, Edgartown, MA 02539

    This ranch style 3 bedroom home centrally located in a quiet neighborhood is close to the bike path with easy access to town and beaches. Sited on a 12,000 square foot parcel with a spacious privately enclosed yard and mature gardens. First floor includes an efficient galley kitchen with a quaint dining area. The living room leads out to a cozy front porch. There is also a spacious side deck that

    Brenda Galligan Karen M. Overtoom R.E.

    67 12th St S, Edgartown, MA 02539
  • 1 Saddle Club Rd, Edgartown, MA 02539
    1 Saddle Club Rd, Edgartown, MA 02539
    1 Saddle Club Rd, Edgartown, MA 02539
    /41

    $1,475,000

    • 3 Beds
    • 2.5 Baths
    • 1,822 Sq Ft

    1 Saddle Club Rd, Edgartown, MA 02539

    Welcome to your perfect island retreat in the heart of Edgartown conveniently located in a quiet neighborhood off of Edgartown West Tisbury Road. This charming 3-bedroom, 2.5 bathroom home offers the ideal blend of comfort, and functionality. Nestled on a quiet street, the property features an oversized two-car garage--perfect for storing vehicles, bikes, and beach gear, or even setting up a

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    1 Saddle Club Rd, Edgartown, MA 02539
  • 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
  • 6 Janes Cove Rd, Edgartown, MA 02539
    6 Janes Cove Rd, Edgartown, MA 02539
    6 Janes Cove Rd, Edgartown, MA 02539
    /78

    $8,500,000

    • 6 Beds
    • 6.5 Baths
    • 6,927 Sq Ft

    6 Janes Cove Rd, Edgartown, MA 02539

    Waterfront on Edgartown Great Pond, this newly-renovated Coastal Colonial is set on a very private 9.2 acre lot on Janes Cove. You know you are somewhere very special the moment you enter through the gates. As you travel along the cobblestone lined driveway flanked by lush lawns, the gorgeous home rises before you. Stunning the day it was originally completed, it has now been completely renovated

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    6 Janes Cove Rd, Edgartown, MA 02539
  • 19 Locust Ln, Aquinnah, MA 02535
    19 Locust Ln, Aquinnah, MA 02535
    19 Locust Ln, Aquinnah, MA 02535
    /38

    $4,995,000

    • 7 Beds
    • 4.5 Baths
    • 5,982 Sq Ft

    19 Locust Ln, Aquinnah, MA 02535

    This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors take

    Brenda Galligan Karen M. Overtoom R.E.

    19 Locust Ln, Aquinnah, MA 02535
  • 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

    $825,000

    • 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

    $825,000

    • 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
  • 12 W Farm Rd, West Tisbury, MA 02575
    12 W Farm Rd, West Tisbury, MA 02575
    12 W Farm Rd, West Tisbury, MA 02575
    /42

    $1,845,000 Open Sun 1:30PM - 2:30PM

    • 3 Beds
    • 3 Baths
    • 1,389 Sq Ft

    12 W Farm Rd, West Tisbury, MA 02575

    Welcome to your dream home in the picturesque town of West Tisbury, nestled in the coveted Coffins Field neighborhood.This stunning home has undergone a total renovation, resulting in a fresh, modern, and inviting atmosphere. The home boasts an expansive layout with 3 bedrooms and 3 bathrooms and that includes a completely finished, unaccounted approximate 850 sqft walk-out basement. The

    Joe & Nicole Holland Vineyard Dream Realty LLC

    12 W Farm Rd, West Tisbury, MA 02575
  • 00 Bernard Cir Unit 10, Tisbury, MA 02568
    00 Bernard Cir Unit 10, Tisbury, MA 02568
    00 Bernard Cir Unit 10, Tisbury, MA 02568
    /4

    $600,000

    • Land
    • 0.23 Acre
    • $2,614,379 per Acre

    00 Bernard Cir Unit 10, Tisbury, MA 02568

    Rare opportunity to build your dream home in a quiet, well-established Vineyard Haven neighborhood. This level parcel offers excellent potential with flexible zoning that allows for as many bedrooms as will fit within the allowable footprint, governed by 20-foot front and rear setbacks and 10-foot sides. Not located in the watershed district, the property does not require an enhanced septic

    Patrick McCarthy Grace Hagerty Real Estate Inc

    00 Bernard Cir Unit 10, Tisbury, MA 02568
  • 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
  • 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

    $599,000

    • Land
    • 0.29 Acre
    • $2,065,517 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
  • 37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
    37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
    37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
    /9

    $599,000

    • Land
    • 0.29 Acre
    • $2,038,802 per Acre

    37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557

    This is your opportunity to get in on the ground floor of what will be a stunning, new development --- Lagoon Ridge. Several homes are already in place. This beautiful, wooded parcel 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

    Lynn Buder Sandpiper Realty

    37 Double Ox Rd Unit 44, Oak Bluffs, MA 02557
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /21

    $1,999,999

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

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

    Kristin Francoeur Gibson Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    /32

    $2,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    29 Old Nursery Ln, Chilmark, MA 02535

    Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

    Julianna Flanders Flanders Real Estate

    29 Old Nursery Ln, Chilmark, MA 02535
  • 136 W Spring St, Vineyard Haven, MA 02568
    136 W Spring St, Vineyard Haven, MA 02568
    136 W Spring St, Vineyard Haven, MA 02568
    /6

    $900,000

    • 1 Bed
    • 1 Bath
    • 534 Sq Ft

    136 W Spring St, Vineyard Haven, MA 02568

    136 Spring Street - Sited on 0.32 acres and just moments from the Tisbury School and downtown Vineyard Haven, this one bedroom, one bathroom home is serviced by a 4-bedroom septic system, allowing for immediate expansion.Note: This property is also being marketed as a compound with the abutting 4BR/2.5BA home at 128 Spring Street.

    David Dickinson Compass | Point B

    136 W Spring St, Vineyard Haven, MA 02568
  • 128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    /32

    $1,600,000

    • 5 Beds
    • 3.5 Baths
    • 2,436 Sq Ft

    128 W Spring St, Vineyard Haven, MA 02568

    128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

    David Dickinson Compass | Point B

    128 W Spring St, 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
  • 78 Whalers Walk, Edgartown, MA 02539
    78 Whalers Walk, Edgartown, MA 02539
    78 Whalers Walk, Edgartown, MA 02539
    /32

    $1,725,000

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    78 Whalers Walk, Edgartown, MA 02539

    Nestled in a tranquil residential neighborhood, at the top of a curved drive through beautiful trees, this well-maintained home in move-in condition offers an idyllic Martha's Vineyard lifestyle. Custom-built for quality and convenience by a prestigious Island builder, every detail was thoughtfully planned for exclusive use by the family as a cherished year-round vacation home. The open floor

    Dawn Bellante Sandpiper Realty Inc

    78 Whalers Walk, Edgartown, MA 02539
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /42

    $3,995,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    /45

    $6,395,000

    • 6 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    400 Barnes Rd, Vineyard Haven, MA 02568

    Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

    Jennifer DaSilva Compass | Point B

    400 Barnes Rd, Vineyard Haven, MA 02568
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /39

    $3,500,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • 139 Main St, Vineyard Haven, MA 02568
    139 Main St, Vineyard Haven, MA 02568
    139 Main St, Vineyard Haven, MA 02568
    /52

    $3,750,000

    • 5 Beds
    • 6.5 Baths
    • 4,372 Sq Ft

    139 Main St, Vineyard Haven, MA 02568

    Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

    Leslie Floyd Portfolio Properties

    139 Main St, Vineyard Haven, MA 02568
  • 32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
    /25

    $3,200,000

    • Land
    • 19.3 Acres
    • $165,803 per Acre

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

    A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

    Jill Napior Tea Lane Associates

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
  • 5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
    /13

    $6,750,000

    • Land
    • 2.11 Acres
    • $3,199,052 per Acre

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

    Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

    Deb Levin Studio Realty

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
  • 108 Bay View Ave, Edgartown, MA 02539
    108 Bay View Ave, Edgartown, MA 02539
    108 Bay View Ave, Edgartown, MA 02539
    /26

    $1,700,000

    • 2 Beds
    • 0.5 Baths
    • 601 Sq Ft

    108 Bay View Ave, Edgartown, MA 02539

    Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

    Derick Freitas Amaral & Associates Real Estate

    108 Bay View Ave, Edgartown, MA 02539
  • 108 Bay View, Edgartown, MA 02539
    108 Bay View, Edgartown, MA 02539
    108 Bay View, Edgartown, MA 02539
    /26

    $1,700,000

    • Land
    • 0.96 Acre
    • $1,770,833 per Acre

    108 Bay View, Edgartown, MA 02539

    Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

    Derick Freitas Amaral & Associates RE

    108 Bay View, Edgartown, MA 02539

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