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Properties For Sale In Chilmark

Properties For Sale In Chilmark

Noted for rolling hills, roaming wildlife, old stone walls and gorgeous coastline that create a scene straight out of a pastoral painting, Chilmark is a picturesque Up-Island town on Martha’s Vineyard.

1 - 18 of 46 properties

8 Wauwompauque Trail

For sale

$5,300,000

Listed Aug 22, 2026

8 Wauwompauque Trail

Chilmark, MA 02535

Beds
5
Baths
3
Acres
2.6
Built
1966
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0 Cencelle

For sale

$1,275,000

Listed Aug 15, 2026

0 Cencelle

Chilmark, MA 02535

Acres
3.91
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220 North Road

For sale

$2,195,000

Listed Aug 14, 2026

220 North Road

Chilmark, MA 02535

Beds
7
Baths
4
Acres
3
Built
1976
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220 North Road

For sale

$2,195,000

Listed Aug 12, 2026

220 North Road

Chilmark, MA 02535

Beds
7
Baths
4
Acres
3
Built
1976
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23 Flanders Lane

For sale

$9,750,000

Listed Aug 10, 2026

23 Flanders Lane

Chilmark, MA 02535

Beds
7
Baths
5
Acres
8.7
Built
1930
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25 Brickyard Road

For sale

$16,250,000

Listed Aug 9, 2026

25 Brickyard Road

Chilmark, MA 02535

Beds
6
Baths
7
Acres
10.69
Built
2020
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3 Ben's Way

For sale

$3,900,000

Listed Aug 7, 2026

3 Ben's Way

Chilmark, MA 02535

Beds
3
Baths
4
Acres
3.9
Built
1995
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28 Black Point Road

For sale

$2,950,000

Listed Jul 14, 2026

28 Black Point Road

Chilmark, MA 02535

Beds
3
Baths
3
Acres
5.4
Built
1982
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132 South Road

For sale

$1,300,000

Listed Jul 8, 2026

132 South Road

Chilmark, MA 02535

Beds
4
Baths
3
Acres
1.9
Built
1950
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8 Rumpus Ridge

For sale

$1,550,000

Listed Jul 2, 2026

8 Rumpus Ridge

Chilmark, MA 02535

Beds
4
Baths
2
Acres
0.5
Built
1968
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139 Tea Lane

For sale

$2,095,000

Listed Jul 1, 2026

139 Tea Lane

Chilmark, MA 02535

Beds
3
Baths
3
Acres
4.8
Built
2023
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8 Snail Road

For sale

$15,400,000

Listed Jun 18, 2026

8 Snail Road

Chilmark, MA 02535

Beds
6
Baths
8
Acres
9.61
Built
1961
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49 Gosnolds Way

For sale

$5,200,000

Listed Jun 7, 2026

49 Gosnolds Way

Chilmark, MA 02535

Beds
5
Baths
3
Acres
9.8
Built
2003
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35 South Bowl Road

For sale

$4,995,000

Listed Jun 7, 2026

35 South Bowl Road

Chilmark, MA 02535

Beds
3
Baths
2
Acres
5.3
Built
2016
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131 State Road

For sale

$3,950,000

Listed Jun 6, 2026

131 State Road

Chilmark, MA 02535

Beds
3
Baths
2
Acres
0.1
Built
2003
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15 Menemsha Inn Road

For sale

$1,250,000

Listed May 29, 2026

15 Menemsha Inn Road

Chilmark, MA 02535

Acres
1.9
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17 Chockers Lane

For sale

$5,500,000

Listed May 28, 2026

17 Chockers Lane

Chilmark, MA 02535

Beds
2
Baths
1
Acres
1
Built
1946
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100 Gosnolds Way

For sale

$3,300,000

Listed May 28, 2026

100 Gosnolds Way

Chilmark, MA 02535

Beds
4
Baths
2
Acres
5
Built
1994
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Martha's Vineyard Real Estate Properties By Town

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West Tisbury Areas

Chilmark

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Martha's Vineyard Real Estate Properties By Type

Single Family Homes in Martha's Vineyard

Single Family

Searching for a single-family home on Martha's Vineyard? With Anchor Realty Real Estate, you can count on receiving personalized service & solutions! Call +1 (508) 696-7777 today.

Condos for Sale in Martha's Vineyard

Condos

Anchor Realty Real Estate is your source for all of your real estate needs. Whether you're looking for a condo or a second home, we are here for you. Call +1 (508) 696-7777 today.

Commercial Properties for Sale in Martha's Vineyard

Commercial

Looking for commercial properties for sale in Martha's Vineyard? Count on the team at Anchor Realty Real Estate for all of your real estate needs. Call +1 (508) 696-7777 today.

Land for Sale in Martha's Vineyard

Land

Looking for land for sale in Martha's Vineyard? The team at Anchor Realty Real Estate is your source for expert real estate services, resources & more. Call +1 (508) 696-7777 today.

Multi-Family Homes in Martha's Vineyard

Multi Family

With Anchor Realty Real Estate, you can count on us to help you find the perfect multi-family home on Martha's Vineyard. Contact us today for listings & more. Call +1 (508) 696-7777 today.