344

Dukes County MA Homes for Sale

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  • 131 State Rd, Chilmark, MA 02535
    131 State Rd, Chilmark, MA 02535
    131 State Rd, Chilmark, MA 02535
    /29

    $3,950,000

    $400K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    131 State Rd, Chilmark, MA 02535

    Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller

    Jim Feiner Feiner Real Estate

    131 State Rd, Chilmark, MA 02535
  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the beach. Two Year-round 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

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • 52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
    /5

    $639,000

    • Land
    • 12,998 Sq Ft
    • $2,141,421 per Acre

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
  • 52 Heath Hen Ln, Vineyard Haven, MA 02568
    52 Heath Hen Ln, Vineyard Haven, MA 02568
    52 Heath Hen Ln, Vineyard Haven, MA 02568
    /3

    $639,000

    • Land
    • 13,068 Sq Ft
    • $2,130,000 per Acre

    52 Heath Hen Ln, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot sunny lot is ready for your Vineyard home. The property comes with a complete six bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

    Tina Miller Donnelly + Co.

    52 Heath Hen Ln, Vineyard Haven, MA 02568
  • 19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    /14

    $825,000

    • 2 Beds
    • 1 Bath
    • 985 Sq Ft

    19 Perkins Ave, Oak Bluffs, MA 02557

    Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

    Katherine Donahue Sandpiper Realty

    19 Perkins Ave, Oak Bluffs, MA 02557
  • 312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    /36

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    312 E Chop Dr, Oak Bluffs, MA 02557

    “The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

    Alyssa Halisky Wallace & Co. Sotheby's

    312 E Chop Dr, Oak Bluffs, MA 02557
  • 312 E Chop Dr, Vineyard Haven, MA 02568
    312 E Chop Dr, Vineyard Haven, MA 02568
    312 E Chop Dr, Vineyard Haven, MA 02568
    /36

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    312 E Chop Dr, Vineyard Haven, MA 02568

    ''The Doll House'' is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    312 E Chop Dr, Vineyard Haven, MA 02568
  • 41 Moshup Trail, Aquinnah, MA 02535
    41 Moshup Trail, Aquinnah, MA 02535
    41 Moshup Trail, Aquinnah, MA 02535
    /43

    $3,875,000

    $125K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,304 Sq Ft

    41 Moshup Trail, Aquinnah, MA 02535

    The Best of Aquinnah: Surf, Views, and Total Privacy. There is nothing quite like the south shore of Aquinnah, and this five-bedroom home puts you right in the heart of it. Tucked away along Moshup Trail, the property, lovingly referred to as "Surfside", is all about the Atlantic views and the effortless, barefoot lifestyle that comes with being this close to the water. The house is bright and

    Heidi Vanderhoop Tea Lane Associates

    41 Moshup Trail, Aquinnah, MA 02535
  • 19 Locust Ln, Aquinnah, MA 02535
    19 Locust Ln, Aquinnah, MA 02535
    19 Locust Ln, Aquinnah, MA 02535
    /43

    $6,950,000

    • 7 Beds
    • 4.5 Baths
    • 6,921 Sq Ft

    19 Locust Ln, Aquinnah, MA 02535

    There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah — the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here.19 Locust Lane is one of them.Nearly 17 acres high above Vineyard Sound, with open water views to

    Creatini Group eXp Realty

    19 Locust Ln, Aquinnah, MA 02535
  • 7 Ploughshare Ln, Oak Bluffs, MA 02557
    7 Ploughshare Ln, Oak Bluffs, MA 02557
    7 Ploughshare Ln, Oak Bluffs, MA 02557
    /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • 9 Sutton's Way, Edgartown, MA 02539
    9 Sutton's Way, Edgartown, MA 02539
    9 Sutton's Way, Edgartown, MA 02539
    /65

    $7,999,000

    • 7 Beds
    • 6.5 Baths
    • 7,133 Sq Ft

    9 Sutton's Way, Edgartown, MA 02539

    Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a

    Jennifer DaSilva Compass | Point B

    9 Sutton's Way, Edgartown, MA 02539
  • 3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    /26

    $1,349,000

    • 3 Beds
    • 2 Baths
    • 1,863 Sq Ft

    3 Troy St, Oak Bluffs, MA 02557

    Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    3 Troy St, Oak Bluffs, MA 02557
  • 15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    /11

    $1,250,000

    • Land
    • 1.9 Acres
    • $657,895 per Acre

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

    Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

    Jill Napior Tea Lane Associates

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
  • 37 Dodgers Hole Rd, Edgartown, MA 02539
    37 Dodgers Hole Rd, Edgartown, MA 02539
    37 Dodgers Hole Rd, Edgartown, MA 02539
    /33

    $1,249,900

    • 3 Beds
    • 2 Baths
    • 1,338 Sq Ft

    37 Dodgers Hole Rd, Edgartown, MA 02539

    This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with

    Beth Welch Viewpoints

    37 Dodgers Hole Rd, Edgartown, MA 02539
  • 4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    /31

    $1,150,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond Rd, Vineyard Haven, MA 02568

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home

    Patricia Lyman Compass

    4 Rock Pond Rd, Vineyard Haven, MA 02568
  • 17 Chockers Ln, Chilmark, MA 02535
    17 Chockers Ln, Chilmark, MA 02535
    17 Chockers Ln, Chilmark, MA 02535
    /22

    $5,500,000

    • 2 Beds
    • 1 Bath
    • 808 Sq Ft

    17 Chockers Ln, Chilmark, MA 02535

    Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard — a property that has

    Julianna Flanders Flanders Real Estate

    17 Chockers Ln, Chilmark, MA 02535
  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,400,000

    • 4 Beds
    • 2.5 Baths
    • 2,383 Sq Ft

    100 Gosnolds Way, Chilmark, MA 02535

    Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

    Julianna Flanders Flanders Real Estate

    100 Gosnolds Way, Chilmark, MA 02535
  • 20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    /33

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,701 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • 10 N Bog Rd, Edgartown, MA 02539
    10 N Bog Rd, Edgartown, MA 02539
    10 N Bog Rd, Edgartown, MA 02539
    /34

    $2,999,000

    $196K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,881 Sq Ft

    10 N Bog Rd, Edgartown, MA 02539

    Set on 2.2 acres in Edgartown, this five-bedroom home with a heated saltwater pool is just moments from Morning Glory Farm, South Beach, the bike path, and Edgartown Village. It features three finished levels designed for coastal living, with gathering spaces and indoor-outdoor flow. At the center of the home is the kitchen and dining area that opens onto an expansive deck overlooking the 16’ x

    Michele Casavant Vineyard Village Realty

    10 N Bog Rd, Edgartown, MA 02539
  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /53

    $9,875,000

    • 6 Beds
    • 5.5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended

    Jill Napior Tea Lane Associates

    6 Wakeman Rd, Chilmark, MA 02535
  • 31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    /70

    $4,125,000

    Open Sat 10:30AM - 12:30PM $525K PRICE DROP
    • 7 Beds
    • 4.5 Baths
    • 3,312 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    OPEN HOUSE Saturday, August 8th 10:30am-12:30pm. An Inspirational Oasis - Come unwind and experience a secluded multi-dwelling compound nestled along the gentle slopes of Indian Hill, where rural tranquility meets effortless island living on more than three acres of uncommon beauty. Centered around a heated saltwater pool reminiscent of a private resort, the main house, studio barn, and

    Helena Kirschenbaum Studio Realty

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • 299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
    /16

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Karen Overtoom Karen M. Overtoom R.E.

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
  • 18 Point Inner Way, Chilmark, MA 02535
    18 Point Inner Way, Chilmark, MA 02535
    18 Point Inner Way, Chilmark, MA 02535
    /65

    $45,000,000

    • 7 Beds
    • 13 Baths
    • 14,780 Sq Ft

    18 Point Inner Way, Chilmark, MA 02535

    A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Point Inner Way, Chilmark, MA 02535
  • 14 Ephriam Allen Rd, West Tisbury, MA 02568
    14 Ephriam Allen Rd, West Tisbury, MA 02568
    14 Ephriam Allen Rd, West Tisbury, MA 02568
    /25

    $2,475,000

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

    14 Ephriam Allen Rd, West Tisbury, MA 02568

    Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys waterviews of Vineyard Sound and the Sanctuary. There's also a sweet detached 1-br

    Michelle Kelly Tea Lane Associates

    14 Ephriam Allen Rd, West Tisbury, MA 02568
  • 61 Wood Chips Cir, Vineyard Haven, MA 02568
    61 Wood Chips Cir, Vineyard Haven, MA 02568
    61 Wood Chips Cir, Vineyard Haven, MA 02568
    /12

    $1,195,000

    • 1 Bed
    • 1 Bath
    • 768 Sq Ft

    61 Wood Chips Cir, Vineyard Haven, MA 02568

    Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature. The true value lies in the property’s remarkable expansion

    Andrew McElhinney Compass LLC

    61 Wood Chips Cir, Vineyard Haven, MA 02568
  • 299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    /21

    $1,175,000

    Open House 8/17 $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Alyson Parker Karen M. Overtoom R.E.

    299 Daggett Ave, Vineyard Haven, MA 02568
  • 21 Schoolhouse Rd, Edgartown, MA 02539
    21 Schoolhouse Rd, Edgartown, MA 02539
    21 Schoolhouse Rd, Edgartown, MA 02539
    /25

    $1,696,000

    $199K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,638 Sq Ft

    21 Schoolhouse Rd, Edgartown, MA 02539

    Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on

    Jim Joyce Carroll & Vincent R.E.

    21 Schoolhouse Rd, Edgartown, MA 02539
  • 15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    /42

    $4,600,000

    $350K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

    Stephanie Roache Donnelly + Co.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • 10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    10 Abels Neck Rd, Chilmark, MA 02535

    Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, Chilmark, MA 02535
  • 7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    /4

    $809,000

    • Land
    • 16,901 Sq Ft
    • $2,085,052 per Acre

    7 Highland Ave Unit 119, Vineyard Haven, MA 02568

    Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

    Shera Toledo eXp Realty

    7 Highland Ave Unit 119, Vineyard Haven, MA 02568
  • 15 21st St N, Edgartown, MA 02539
    15 21st St N, Edgartown, MA 02539
    15 21st St N, Edgartown, MA 02539
    /66

    $2,675,000

    $275K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 3,740 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

    Jennifer O'hanlon Compass LLC

    15 21st St N, Edgartown, MA 02539
  • 7 Pip'N Rd, Edgartown, MA 02539
    7 Pip'N Rd, Edgartown, MA 02539
    7 Pip'N Rd, Edgartown, MA 02539
    /52

    $2,195,000

    Open Sun 11AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pip'N Rd, Edgartown, MA 02539

    A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

    Dawn Bellante-Holand Sandpiper Realty

    7 Pip'N Rd, Edgartown, MA 02539
  • 13 Young St, Edgartown, MA 02539
    13 Young St, Edgartown, MA 02539
    13 Young St, Edgartown, MA 02539
    /29

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    13 Young St, Edgartown, MA 02539

    This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an

    Stacy Ickes Donnelly + Co.

    13 Young St, Edgartown, MA 02539
  • 14 Ridge Rd Unit 94, Aquinnah, MA 02535
    14 Ridge Rd Unit 94, Aquinnah, MA 02535
    14 Ridge Rd Unit 94, Aquinnah, MA 02535
    /15

    $1,195,000

    • Land
    • 5.7 Acres
    • $209,649 per Acre

    14 Ridge Rd Unit 94, Aquinnah, MA 02535

    Nearly 6 acres of land bordered by stonewalls on two sides. The property has been cleared, so you are able to see the level topography and mature trees. The location lends itself to a short walk to Lobsterville Beach or Red Beach on Menemsha Pond, where you can hop on your paddleboard or kayak or get to your mooring. There is fresh fish to catch off the beach or clams to gather from the Pond for

    Jill Napior Tea Lane Associates

    14 Ridge Rd Unit 94, Aquinnah, MA 02535
  • 27 Spring St, Vineyard Haven, MA 02568
    27 Spring St, Vineyard Haven, MA 02568
    27 Spring St, Vineyard Haven, MA 02568
    /58

    $2,895,000

    • 5 Beds
    • 4 Baths
    • 2,300 Sq Ft

    27 Spring St, Vineyard Haven, MA 02568

    Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • 7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    /13

    $5,100,000

    • Land
    • 2.34 Acres
    • $2,179,487 per Acre

    7 Overview Ln, Oak Bluffs, MA 02557

    A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    7 Overview Ln, Oak Bluffs, MA 02557
  • 61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    /55

    $5,100,000

    $350K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,513 Sq Ft

    61 Stonewall Rd, Chilmark, MA 02535

    Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    61 Stonewall Rd, Chilmark, MA 02535
  • 0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • 25 Lelands Path, Edgartown, MA 02539
    25 Lelands Path, Edgartown, MA 02539
    25 Lelands Path, Edgartown, MA 02539
    /56

    $9,995,000

    • 6 Beds
    • 7.5 Baths
    • 7,205 Sq Ft

    25 Lelands Path, Edgartown, MA 02539

    YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200

    Agent Photo

    Wendy Harman

    Compass | Point B

    25 Lelands Path, Edgartown, MA 02539
  • 0 Bayberry Hill Rd Unit 73520603, Gosnold, MA 02713
    0 Bayberry Hill Rd Unit 73520603, Gosnold, MA 02713
    0 Bayberry Hill Rd Unit 73520603, Gosnold, MA 02713
    /12

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    0 Bayberry Hill Rd Unit 73520603, Gosnold, MA 02713

    Perched high above the harbor on one of New England’s most secluded islands, Folly on Bayberry Hill is a classic Cuttyhunk retreat offering exceptional privacy, timeless coastal character, and sweeping panoramic water views. The home’s elevated setting creates a remarkable sense of openness, light, and connection to the surrounding coastal landscape. Inside, approximately 1,472 square feet of

    Slater Anderson LandVest, Inc.

    0 Bayberry Hill Rd Unit 73520603, Gosnold, MA 02713

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