73

Homes for Sale in 02535

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  • /27

    $1,649,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    North Star Real Estate, LLC

    43 N Slope Ln, Chilmark, MA 02535
  • /31

    $1,649,900

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate, LLC

    43 N Slope Ln, Chilmark, MA 02535
  • /15

    $6,250,000

    • Land
    • 21 Acres
    • $297,619 per Acre

    44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535

    This exceptional 21-acre estate offers sweeping ocean views, remarkable privacy, and a rare opportunity to create a truly special island retreat. Tucked among the rolling hills, open farmlands, and woodlands of Chilmark, the property combines a profound sense of seclusion with extraordinary natural beauty and the flexibility to shape the land to suit a variety of visions—including the potential

    Meg Bodnar Tea Lane Associates

    44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535
  • /79

    $5,300,000

    • 5 Beds
    • 3.5 Baths
    • 2,210 Sq Ft

    8 Wauwompauque Trail, Chilmark, MA 02535

    Abels Hill opportunity! Coastal living at its finest in this contemporary Abels Hill retreat, where south-facing ocean views and exceptional amenities define the lifestyle. Situated within one of Chilmark's most sought-after communities, the property enjoys exclusive access to the Atlantic Ocean, Chilmark Pond, and private association tennis courts.The property features a beautifully designed

    Jill Napior Tea Lane Associates

    8 Wauwompauque Trail, Chilmark, MA 02535
  • /14

    $1,275,000

    • Land
    • 3.91 Acres
    • $326,087 per Acre

    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535

    Set amid the rolling farmlands of Chilmark, this beautiful parcel offers an exceptional opportunity to create your own island retreat. Framed by stone walls, wooded surroundings, and open meadow views, the property combines privacy and natural beauty in a serene rural setting with glacial erratics and trails winding throughout. Elevated and peaceful, this is a rare opportunity to build a home

    Meg Bodnar Tea Lane Associates

    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
  • /39

    $2,400,000

    • 7 Beds
    • 4 Baths
    • 2,232 Sq Ft

    220 North Rd, Chilmark, MA 02535

    Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation

    David Lott Vineyard Open House Real Estate

    220 North Rd, Chilmark, MA 02535
  • /40

    $1,695,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,702 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • /46

    $2,490,000

    • 3 Beds
    • 3.5 Baths
    • 3,579 Sq Ft

    8 Jeffers Way, Aquinnah, MA 02535

    Tucked away on more than two acres along a private dirt road, this extensively updated post-and-beam home offers exceptional space and privacy in a peaceful Aquinnah setting. The property is surrounded by woodlands, open fields, streams, and ancient stone walls and is located approximately one mile from Aquinnah’s resident beaches.With over 3,500 square feet, this home offers generous

    Jennifer O'hanlon Compass LLC

    8 Jeffers Way, Aquinnah, MA 02535
  • /3

    $450,000

    • Land
    • 6,503 Sq Ft
    • $3,014,066 per Acre

    00 Moshup Trail Unit 14.2, Aquinnah, MA 02535

    Become one of only 21 members to access the exclusive Goff Beach, a gated community with parking. Traverse to the top of the sandy dune and overlook the sparkling ocean with wide sandy beach. A special opportunity rarely offered for sale. 0.15-acre parcel offers direct access to one of the most desirable stretches of shoreline on Martha’s Vineyard. Situated to the right of the Rainbow House, the

    Rebecca V Conroy Conroy & Company R.E., Inc.

    00 Moshup Trail Unit 14.2, Aquinnah, MA 02535
  • /49

    $9,750,000

    • 7 Beds
    • 5 Baths
    • 3,617 Sq Ft

    23 Flanders Ln, Chilmark, MA 02535

    A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

    Julianna Flanders Flanders Real Estate

    23 Flanders Ln, Chilmark, MA 02535
  • /56

    $16,250,000

    • 6 Beds
    • 8 Baths
    • 8,648 Sq Ft

    25 Brickyard Rd, Chilmark, MA 02535

    Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

    Peyton Wallace Studio Realty LLC

    25 Brickyard Rd, Chilmark, MA 02535
  • /46

    $3,900,000

    • 3 Beds
    • 4 Baths
    • 2,960 Sq Ft

    3 Bens Way, Chilmark, MA 02535

    Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and

    Russell Maloney Russell Maloney Real Estate

    3 Bens Way, Chilmark, MA 02535
  • /42

    $2,175,000

    $75K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
  • /8

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience --

    Peyton Wallace Studio Realty LLC

    34 Ebens Ln, Chilmark, MA 02535
  • /55

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 1,469 Sq Ft

    28 Black Point Rd, Chilmark, MA 02535

    Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach.

    Michele Moore Island Real Estate

    28 Black Point Rd, Chilmark, MA 02535
  • /34

    $1,600,000

    • 3 Beds
    • 3 Baths
    • 2,155 Sq Ft

    132 South Rd, Chilmark, MA 02535

    Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

    Lisa Da Silva Compass

    132 South Rd, Chilmark, MA 02535
  • /37

    $3,795,000

    • 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
  • /29

    $1,550,000

    • 4 Beds
    • 2 Baths
    • 1,757 Sq Ft

    8 Rumpus Ridge Rd, Chilmark, MA 02535

    Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the

    Julianna Flanders Flanders Real Estate

    8 Rumpus Ridge Rd, Chilmark, MA 02535
  • /7

    $349,000

    • Land
    • 1.26 Acres
    • $276,984 per Acre

    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535

    Lovely beach lot off Moshup Trail in Aquinnah. Enjoy the sandy beach, Atlantic Ocean water and beauty of the South shore. This private beach lot is shared with only seven other members. Parking is located a short walk across the road from the beach access.Private parking limited to one car per member. This is not a buildable lot.

    Julianna Flanders Flanders Real Estate

    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
  • /34

    $2,095,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    139 Tea Ln, Chilmark, MA 02535

    Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

    Meg Bodnar Tea Lane Associates

    139 Tea Ln, Chilmark, MA 02535
  • /31

    $15,400,000

    • 6 Beds
    • 9 Baths
    • 6,967 Sq Ft

    8 Snail Rd, Chilmark, MA 02535

    Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

    Brian Dougherty Corcoran Property Advisors

    8 Snail Rd, Chilmark, MA 02535
  • /20

    $325,000

    $5K PRICE DROP
    • Land
    • 7,405 Sq Ft
    • $1,911,765 per Acre

    00 Moshup Trail, Aquinnah, MA 02535

    Tucked along the south shore of Aquinnah on Martha's Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

    Sheila Morse Island Real Estate

    00 Moshup Trail, Aquinnah, MA 02535
  • /32

    $5,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnolds Way, Chilmark, MA 02535

    Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    49 Gosnolds Way, Chilmark, MA 02535
  • /35

    $5,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

    Bonnie Pierce Wallace & Co. Sotheby's

    49 Gosnold's Way, Chilmark, MA 02535
  • /42

    $4,995,000

    $405K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,710 Sq Ft

    35 S Bowl Rd, Chilmark, MA 02535

    Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking

    Tina Miller Donnelly + Co.

    35 S Bowl 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
  • /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
  • /42

    $5,900,000

    $1M PRICE DROP
    • 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 the

    Federico Creatini eXp Realty LLC - Corporate Office

    19 Locust Ln, Aquinnah, 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
  • /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
  • /46

    $3,300,000

    $100K PRICE DROP
    • 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
  • /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
  • /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
  • /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
  • /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
  • /39

    $16,000,000

    • 2 Beds
    • 2 Baths
    • 1,041 Sq Ft

    0, 36, 38 Black Point Rd, 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 home sits on one lot with two detached studios alongside. Close to nature, this seasonal home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd, Chilmark, MA 02535
  • /26

    $2,195,000

    $300K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,510 Sq Ft

    26 Bijahs Way, Chilmark, MA 02535

    This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living

    Brenda Galligan Karen M. Overtoom R.E.

    26 Bijahs Way, Chilmark, MA 02535
  • /46

    $6,250,000

    • 5 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • /52

    $4,975,000

    $320K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • /9

    $1,900,000

    • Land
    • 15.05 Acres
    • $126,246 per Acre

    0 High Mark Rd Unit 66, Chilmark, MA 02535

    A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today.The parcel directly abuts the nearly 80 acres of conservation land at the

    Russell Maloney Russell Maloney Real Estate

    0 High Mark Rd Unit 66, Chilmark, MA 02535

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