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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 39 properties

11 Lookout Place

For sale

$2,850,000

Listed Oct 26, 2026

11 Lookout Place

Chilmark, MA 02535

Beds
4
Baths
2.5
Acres
3.8
Built
1987
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1 Clam Point Cove Road

For sale

$7,900,000

Listed Oct 5, 2026

1 Clam Point Cove Road

Chilmark, MA 02535

Beds
7
Baths
6
Acres
3
Built
1976
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8 Wauwompauque Trail

For sale

$5,300,000

Listed Aug 22, 2026

8 Wauwompauque Trail

Chilmark, MA 02535

Beds
5
Baths
3.5
Acres
2.6
Built
1966
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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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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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132 South Road

For sale

$1,100,000

Listed Jul 8, 2026

132 South Road

Chilmark, MA 02535

Beds
4
Baths
3
Acres
1.9
Built
1950
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8 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
3.5
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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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

$4,950,000

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
2.5
Acres
5
Built
1994
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6 Wakeman Road

For sale

$9,875,000

Listed May 27, 2026

6 Wakeman Road

Chilmark, MA 02535

Beds
6
Baths
5.5
Acres
4
Built
1934
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18 Point Inner Way

For sale

$45,000,000

Listed May 25, 2026

18 Point Inner Way

Chilmark, MA 02535

Beds
7
Baths
12
Acres
4.9
Built
2012
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0, 36, 38 Black Point Road

For sale

$16,000,000

Listed May 18, 2026

0, 36, 38 Black Point Road

Chilmark, MA 02535

Acres
46
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0, 36, 38 Black Point Road

For sale

$16,000,000

Listed May 18, 2026

0, 36, 38 Black Point Road

Chilmark, MA 02535

Beds
2
Baths
2
Acres
46
Built
1973
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