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SEARCH RESULTS: 42 Listings
CHILMARK - All Property Types
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Town: CHILMARK | All Chilmark listings
Address:
18 Point Inner Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
4.90 Acres /
213,444 sq.ft.
$45,000,000.00
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 ...
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Town: CHILMARK | All Chilmark listings
Address:
146 Quenames Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
60.00 Acres /
2,613,600 sq.ft.
$32,500,000.00
Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of Atlantic barrier beach frontage, the property offers an extraordinary sense...
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Town: CHILMARK | All Chilmark listings
Address:
25 Brickyard Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
10.69 Acres /
465,656 sq.ft.
$16,250,000.00
Perched on an elevated 10.69-acre site just off picturesque North Road in Chilmark, this exceptional private compound brings together natural beauty and architectural distinction. Designed by renowned architect Patrick Ahearn, the residence enjoys dramatic views across the Menemsha Hills and Vineyar...
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Town: CHILMARK | All Chilmark listings
Address:
0, 36, 38 Black Point Road, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
46.00 Acres /
2,003,760 sq.ft.
Beach Key: Yes
$16,000,000.00
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 bed...
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Town: CHILMARK | All Chilmark listings
Address:
0, 36, 38 Black Point Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
46.00 Acres /
2,003,760 sq.ft.
$16,000,000.00
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 be...
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Town: CHILMARK | All Chilmark listings
Address:
8 Snail Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
9.61 Acres /
418,611 sq.ft.
$15,400,000.00
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 ...
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Town: CHILMARK | All Chilmark listings
Address:
64 Squibnocket Farm Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.30 Acres /
143,748 sq.ft.
$14,500,000.00
Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore.
Squibnocket Farm Road is renowned for its unspoiled beauty an...
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Town: CHILMARK | All Chilmark listings
Address:
16 Shotnaigher Lane, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.60 Acres /
156,816 sq.ft.
$10,950,000.00
New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound...
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Town: CHILMARK | All Chilmark listings
Address:
6 Wakeman Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
4.00 Acres /
174,240 sq.ft.
$9,875,000.00
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, a...
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Town: CHILMARK | All Chilmark listings
Address:
1 Clam Point Cove Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.00 Acres /
130,680 sq.ft.
$7,900,000.00
Martha's Vineyard has many fine waterfront properties but only a handful of exceptional ones. The Lee Family Compound is an exceptional 3 acre waterfront property with breathtaking unobstructed pond views from an elevated secure location, 750+ ft of pond frontage, 48 ft dock with separate mooring f...
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Town: CHILMARK | All Chilmark listings
Address:
78 Hammett Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.80 Acres /
165,528 sq.ft.
$6,750,000.00
This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets.
The property at the end of a well maintai...
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Town: CHILMARK | All Chilmark listings
Address:
34 Edys Island Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.80 Acres /
165,528 sq.ft.
$6,250,000.00
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 fo...
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Town: CHILMARK | All Chilmark listings
Address:
8 Wauwompauque Trail, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
2.60 Acres /
113,256 sq.ft.
$5,300,000.00
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, Ch...
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Town: CHILMARK | All Chilmark listings
Address:
49 Gosnolds Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
9.80 Acres /
426,888 sq.ft.
$5,200,000.00
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 floo...
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Town: CHILMARK | All Chilmark listings
Address:
35 South Bowl Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
5.30 Acres /
230,868 sq.ft.
$4,995,000.00
Rare opportunity in the Seven Gates Farm community of Chilmark.
Designed by acclaimed architects Jane & Christian Langmuir, this exceptional home is nestled on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace warmth, natural light, and its surrounding environment, the th...
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Town: CHILMARK | All Chilmark listings
Address:
44 Cencelle, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
17.16 Acres /
747,489 sq.ft.
$4,975,000.00
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 out...
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Town: CHILMARK | All Chilmark listings
Address:
17 Chockers Lane, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
1.00 Acres /
43,560 sq.ft.
$4,950,000.00
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 w...
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Town: CHILMARK | All Chilmark listings
Address:
131 State Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
0.10 Acres /
4,356 sq.ft.
$3,950,000.00
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 s...
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Town: CHILMARK | All Chilmark listings
Address:
3 Ben's Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.90 Acres /
169,884 sq.ft.
$3,900,000.00
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...
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Town: CHILMARK | All Chilmark listings
Address:
96 Hammett Lane, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
4.30 Acres /
187,308 sq.ft.
$3,795,000.00
This 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,...
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Town: CHILMARK | All Chilmark listings
Address:
100 Gosnolds Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
5.00 Acres /
217,800 sq.ft.
$3,300,000.00
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...
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Town: CHILMARK | All Chilmark listings
Address:
27 Clambelly Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.10 Acres /
135,036 sq.ft.
$3,295,000.00
A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 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. ...
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Town: CHILMARK | All Chilmark listings
Address:
28 Black Point Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
5.40 Acres /
235,224 sq.ft.
$2,950,000.00
Bright & Airy Black Point Retreat with Deeded Beach Lot 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 backdrop and the shoreline is just moments away...
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CONTINGENT OFFER
STILL SHOWING
Contingent
17th September 2026
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Town: CHILMARK | All Chilmark listings
Address:
11 Lookout Place, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.80 Acres /
165,528 sq.ft.
$2,850,000.00
Situated in the private and sought after Abel's Hill Association, 11 Lookout Place offers natural beauty and quiet tranquility as well as association tennis, private Atlantic ocean beach and Chilmark Pond access. Situated on almost 4 picturesque acres of rolling lawn, with graceful trees and old sto...
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NEW LISTING |
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Town: CHILMARK | All Chilmark listings
Address:
31 Tower Lane and 34 Ebens Lane, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
7.60 Acres /
331,056 sq.ft.
$2,725,000.00
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 gene...
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Town: CHILMARK | All Chilmark listings
Address:
11 By The Woods, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
4.50 Acres /
196,020 sq.ft.
$2,650,000.00
Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plan...
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Town: CHILMARK | All Chilmark listings
Address:
2 Other House Road, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
1.40 Acres /
60,983 sq.ft.
$2,250,000.00
Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with...
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Town: CHILMARK | All Chilmark listings
Address:
26 Bijahs Way, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
1.20 Acres /
52,272 sq.ft.
$2,195,000.00
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 heati...
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Town: CHILMARK | All Chilmark listings
Address:
220 North Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.00 Acres /
130,680 sq.ft.
$2,195,000.00
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 Lin...
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CONTINGENT OFFER
STILL SHOWING
Contingent
9th October 2026
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Town: CHILMARK | All Chilmark listings
Address:
220 North Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.00 Acres /
130,680 sq.ft.
$2,195,000.00
A wonderfully private, peaceful aerie in Chilmark on 3 acres (with a Guest House), featuring a
spacious, high, secluded, wrap-around Deck off of the Living Room and Dining Room. The house is built into the side of a hill which allows more light and 2 areas to be considered "ground level." There is a...
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CONTINGENT OFFER
STILL SHOWING
Contingent
10th October 2026
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Town: CHILMARK | All Chilmark listings
Address:
29 Old Nursery Lane, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.60 Acres /
156,816 sq.ft.
$2,150,000.00
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 proj...
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Town: CHILMARK | All Chilmark listings
Address:
18 Allen Farm Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
2.36 Acres /
102,801 sq.ft.
$2,150,000.00
Changed ↓ from $2,500,000
Was $2,250,000 | Now $2,150,000
Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, espec...
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BACK ON MARKET 23rd October,
2026 PRICE CHANGE |
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Town: CHILMARK | All Chilmark listings
Address:
25 Fulling Mill Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.30 Acres /
143,748 sq.ft.
$1,995,000.00
Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main...
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CONTINGENT OFFER
STILL SHOWING
Contingent
21st October 2026
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Town: CHILMARK | All Chilmark listings
Address:
0 High Mark, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
15.05 Acres /
655,578 sq.ft.
$1,900,000.00
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 ...
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Town: CHILMARK | All Chilmark listings
Address:
43 North Slope Lane, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.50 Acres /
152,460 sq.ft.
$1,649,000.00
Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while rem...
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Town: CHILMARK | All Chilmark listings
Address:
345 North Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
0.50 Acres /
21,780 sq.ft.
$1,375,000.00
This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two ...
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Town: CHILMARK | All Chilmark listings
Address:
0 North Road/15 Belhaven Way, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
4.28 Acres /
186,436 sq.ft.
$1,325,000.00
Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning.
The lot is perfectly sited capturing serene woodland views and the natural contours of Mi...
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Town: CHILMARK | All Chilmark listings
Address:
15 Menemsha Inn Road, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
1.90 Acres /
82,764 sq.ft.
$1,250,000.00
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 sto...
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Town: CHILMARK | All Chilmark listings
Address:
37 Bijahs Way, Chilmark MA 02535
Type: Unimproved Land
Lot Size:
4.40 Acres /
191,664 sq.ft.
$1,245,000.00
FRESHLY BRUSH CUT and EASY to WALK! This quiet and lovely four-and-a-half-acre lot in Chilmark is READY-TO-BUILD. The land has a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, ...
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Town: CHILMARK | All Chilmark listings
Address:
47 Quenames Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.02 Acres /
131,551 sq.ft.
$1,150,000.00
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A ...
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Town: CHILMARK | All Chilmark listings
Address:
45 Quenames Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
3.02 Acres /
131,551 sq.ft.
$1,125,000.00
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two bedrooms, a full bath with shower, an enormous three...
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Town: CHILMARK | All Chilmark listings
Address:
132 South Road, Chilmark MA 02535
Type: Single Family Residence
Lot Size:
1.90 Acres /
82,764 sq.ft.
$1,100,000.00
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 ...
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CONTINGENT OFFER
STILL SHOWING
Contingent
4th October 2026
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