Chilmark, MA Real Estate & Homes For Sale

39 homes

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NEW - 1 DAY AGO
3.8 ACRES
$2,850,000
4 Beds
2.5 Baths
2,630 sqft
11 Lookout Pl,
Chilmark, MA 02535
Tea Lane Associates
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3D VIEW
3 ACRES
$7,900,000
7 Beds
6 Baths
4,150 sqft
1 Clam Point Cove Rd,
Chilmark, MA 02535
Tea Lane Associates
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3.5 ACRES
$1,649,000
3 Beds
2 Baths
1,540 sqft
43 N Slope Lane,
Chilmark, MA 02535
North Star Real Estate, LLC
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2.6 ACRES
$5,300,000
5 Beds
3.5 Baths
2,210 sqft
8 Wauwompauque Trl,
Chilmark, MA 02535
Tea Lane Associates
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10.69 ACRES
$16,250,000
6 Beds
7 Baths
8,648 sqft
25 Brickyard Road,
Chilmark, MA 02535
Studio Realty LLC
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3.9 ACRES
$3,900,000
3 Beds
4 Baths
2,960 sqft
3 Bens Way,
Chilmark, MA 02535
Russell Maloney Real Estate
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3.3 ACRES
$1,995,000
4 Beds
3 Baths
1,918 sqft
21 & 25 Fulling Mill Rd,
Chilmark, MA 02535
Jessica Holtham, Wallace & Co. Sotheby's International Realty
7.6 ACRES
$2,725,000
34 Ebens Lane,
Chilmark, MA 02535
Studio Realty LLC
9.61 ACRES
$15,400,000
6 Beds
8 Baths
6,967 sqft
8 Snail Road,
Chilmark, MA 02535
Corcoran Property Advisors
3D VIEW
9.8 ACRES
$5,200,000
5 Beds
3.5 Baths
4,044 sqft
49 Gosnolds Way,
Chilmark, MA 02535
Wallace & Co. Sotheby's
5.3 ACRES
$4,995,000
3 Beds
2 Baths
2,710 sqft
35 S Bowl Rd,
Chilmark, MA 02535
Donnelly + Co
$3,950,000
3 Beds
2 Baths
1,260 sqft
131 State Rd,
Chilmark, MA 02535
Feiner Real Estate
1.9 ACRES
$1,250,000
15 Menemsha Inn Rd,
Chilmark, MA 02535
Tea Lane Associates
5 ACRES
$3,300,000
4 Beds
2.5 Baths
2,383 sqft
100 Gosnolds Way,
Chilmark, MA 02535
Flanders Real Estate
1 ACRE
$4,950,000
2 Beds
1 Bath
808 sqft
17 Chockers Ln,
Chilmark, MA 02535
Flanders Real Estate
4 ACRES
$9,875,000
6 Beds
5.5 Baths
3,758 sqft
6 Wakeman Rd,
Chilmark, MA 02535
Tea Lane Associates
3D VIEW
4.9 ACRES
$45,000,000
7 Beds
12 Baths
14,780 sqft
18 Point Inner Way,
Chilmark, MA 02535
Wallace & Co. Sotheby's
3D VIEW
46 ACRES
$16,000,000
2 Beds
2 Baths
1,041 sqft
36-38 Black Point Rd,
Chilmark, MA 02535
Tea Lane Associates
2.36 ACRES
$2,150,000
1 Bed
1 Bath
726 sqft
18 Allen Farm Rd,
Chilmark, MA 02535
Kendall & Kendall
1.2 ACRES
$2,195,000
3 Beds
2 Baths
2,510 sqft
26 Bijahs Way,
Chilmark, MA 02535
Karen M. Overtoom R.E.
17.16 ACRES
$4,975,000
4 Beds
3 Baths
3,432 sqft
44 Cencelle St,
Chilmark, MA 02535
Tea Lane Associates
3.8 ACRES
$6,250,000
5 Beds
2.5 Baths
2,269 sqft
34 Edys Island Way,
Chilmark, MA 02535
Tea Lane Associates
4.28 ACRES
$1,325,000
N 15th,
Chilmark, MA 02535
Stacy Ickes, Donnelly + Co.
15.05 ACRES
$1,900,000
High Mark,
Chilmark, MA 02535
Russell Maloney Real Estate
4.5 ACRES
$2,650,000
4 Beds
3 Baths
2,967 sqft
11 By The Woods,
Chilmark, MA 02535
Flanders Real Estate
0.5 ACRES
$1,375,000
5 Beds
5 Baths
2,266 sqft
345 North Rd,
Chilmark, MA 02535
Flanders Real Estate
3D VIEW
60 ACRES
$32,500,000
8 Beds
6 Baths
6,841 sqft
146 Quenames Rd,
Chilmark, MA 02535
Grace Hagerty Real Estate Inc
4.28 ACRES
$1,325,000
North Road 15 Belhaven Way,
Chilmark, MA 02535
Donnelly + Co
3.1 ACRES
$3,295,000
3 Beds
3 Baths
2,500 sqft
27 Clambelly Rd,
Chilmark, MA 02535
Flanders Real Estate
3D VIEW
3.8 ACRES
$6,750,000
5 Beds
3.5 Baths
4,050 sqft
78 Hammett Rd,
Chilmark, MA 02535
Tea Lane Associates
3.6 ACRES
$2,150,000
4 Beds
2.5 Baths
2,522 sqft
29 Old Nursery Ln,
Chilmark, MA 02535
Flanders Real Estate
3.02 ACRES
$1,125,000
2 Beds
1 Bath
896 sqft
45 Quenames Rd,
Chilmark, MA 02535
Sandpiper Realty
3.02 ACRES
$1,150,000
2 Beds
1 Bath
924 sqft
47 Quenames Rd,
Chilmark, MA 02535
Sandpiper Realty
7.6 ACRES
$2,725,000
31 Tower Ln #34,
Chilmark, MA 02535
Studio Realty
4.3 ACRES
$3,795,000
4 Beds
3.5 Baths
3,426 sqft
96 Hammett Ln,
Chilmark, MA 02535
Karen M. Overtoom R.E.
4.4 ACRES
$1,245,000
37 Bijahs Way,
Chilmark, MA 02535
Tea Lane Associates
3.6 ACRES
$10,950,000
4 Beds
3.5 Baths
2,050 sqft
16 Shotnaigher Ln,
Chilmark, MA 02535
Conroy & Company R.E., Inc.
1.4 ACRES
$2,250,000
2 Other House Rd,
Chilmark, MA 02535
Russell Maloney Real Estate
3D VIEW
3.3 ACRES
$14,500,000
4 Beds
4.5 Baths
3,705 sqft
64 Squibnocket Farm Rd,
Chilmark, MA 02535
Wallace & Co. Sotheby's
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Real Estate & Homes For Sale Near Chilmark, MA

We found 30 more homes matching your filters just outside Chilmark

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NEW - 2 DAYS AGO
0.31 ACRES
$1,200,000
6 Beds
2.5 Baths
2,352 sqft
16 W Tashmoo Ave,
Vineyard Haven, MA 02568
Laer Realty Partners
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$1,077,000
2 Beds
2.5 Baths
1,800 sqft
122 Cove Rd #11,
Tisbury, MA 02568
Island Real Estate
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3.3 ACRES
$5,200,000
4 Beds
4.5 Baths
4,792 sqft
22 Bridge Ln,
West Tisbury, MA 02575
Tea Lane Associates
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$975,000
3 Beds
2 Baths
1,629 sqft
152 Edgartown Vineyard Haven Rd,
Vineyard Haven, MA 02568
Laer Realty Partners
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3.1 ACRES
$3,790,000
7 Beds
4.5 Baths
4,464 sqft
31 Josiah Sachem Way,
West Tisbury, MA 02575
Studio Realty LLC
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$1,195,000
3 Beds
2 Baths
1,188 sqft
67 Lagoon Ave,
Tisbury, MA 02568
C McManus Realty Group
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1.4 ACRES
$2,195,000
4 Beds
3.5 Baths
2,264 sqft
235 Longview Rd,
West Tisbury, MA 02575
Tea Lane Associates
$1,200,000
2 Beds
3 Baths
1,737 sqft
176 Sandpiper Ln #12,
Tisbury, MA 02568
Viewpoints
$1,395,000
4 Beds
2 Baths
1,776 sqft
95 Daggett Ave,
Tisbury, MA 02568
Landmarks at TODAY Real Estate
3.3 ACRES
$2,735,000
1 Bed
1 Bath
520 sqft
119 Old Thumb Point Rd,
West Tisbury, MA 02575
Feiner Real Estate
4.3 ACRES
$7,200,000
3 Beds
1 Bath
864 sqft
111 Old Herring Creek Rd,
West Tisbury, MA 02575
Landvest MV
5.3 ACRES
$11,400,000
4 Beds
3.5 Baths
2,480 sqft
104 Old Herring Creek Rd W,
Vineyard Haven, MA 02568
Landvest MV
2.44 ACRES
$1,795,000
4 Beds
1.5 Baths
1,871 sqft
487 Lamberts Cove Rd,
West Tisbury, MA 02575
Tea Lane Associates
1.19 ACRES
$2,295,000
4 Beds
3.5 Baths
3,056 sqft
125 Mayflower Ln,
Tisbury, MA 02568
Sandpiper Realty
1.4 ACRES
$1,850,000
4 Beds
2.5 Baths
2,811 sqft
78 Vineyard Meadow Farms Rd,
Vineyard Haven, MA 02568
Keller Williams Realty
0.86 ACRES
$995,000
Road To The Cemetry,
Cuttyhunk, MA 02713
Linda F. Hopps, Milbury and Company
0.34 ACRES
$2,095,000
4 Beds
4 Baths
2,876 sqft
18 Sylvan Avenue,
Tisbury, MA 02568
Wallace & Co. Sotheby's International Realty
0.25 ACRES
$905,000
3 Beds
1.5 Baths
2,208 sqft
74 Chase Lane & 25 Norton Ave,
Vineyard Haven, MA 02568
Portfolio Properties
0.47 ACRES
$450,000
Old Country Ln,
Vineyard Haven, MA 02568
Karen M. Overtoom R.E.
0.69 ACRES
$2,250,000
4 Beds
3 Baths
1,938 sqft
88 Franklin Street,
Tisbury, MA 02568
Island Real Estate
$1,359,900
4 Beds
4 Baths
2,552 sqft
70 Edgartown Vineyard Haven Rd,
Vineyard Haven, MA 02568
CB Realty
0.82 ACRES
$5,995,000
3 Beds
3 Baths
2,280 sqft
20 Sunnyside Ave,
Tisbury, MA 02568
Studio Realty
1.15 ACRES
$6,150,000
6 Beds
6 Baths
5,034 sqft
59 Hagerty Dr,
Tisbury, MA 02568
Donnelly + Co
5.15 ACRES
$1,600,000
60A Davis Look Rd,
West Tisbury, MA 02575
Flanders Real Estate
0.28 ACRES
$3,295,000
5 Beds
4 Baths
2,330 sqft
29 Lagoon Pond Rd #33,
Vineyard Haven, MA 02568
Madelyn Silvia, Wallace & Co. Sotheby's International Realty
1.6 ACRES
$1,289,000
2 Beds
2 Baths
1,996 sqft
29 Scotchmans Lane,
West Tisbury, MA 02575
Island Real Estate
$725,000
2 Beds
1 Bath
703 sqft
124 Skiff Avenue UNIT G-11,
Tisbury, MA 02568
Anchor Realty of MV
2 ACRES
$1,495,000
4 Beds
2.5 Baths
2,334 sqft
150 Field View Lane,
West Tisbury, MA 02575
Island Real Estate
2.1 ACRES
$2,490,000
3 Beds
3.5 Baths
3,579 sqft
8 Jeffers Way,
Aquinnah, MA 02535
Compass LLC
1.3 ACRES
$1,895,000
5 Beds
3 Baths
3,480 sqft
135 Mayflower Ln,
Tisbury, MA 02568
Donnelly + Co

Chilmark, MA Real Estate Trends

Learn about the Chilmark, MA housing market through trends and averages.

Affordability
Home Value
What Locals Say

Affordability of Living in Chilmark, MA

The median home value is $2,427,920

Month	Median home value
October 2025	$2.36M
November 2025	$2.37M
December 2025	$2.38M
January 2026	$2.39M
February 2026	$2.4M
March 2026	$2.41M
April 2026	$2.4M
May 2026	$2.4M
June 2026	$2.39M
July 2026	$2.39M
August 2026	$2.41M
September 2026	$2.43M

View as a graph

Trends and affordability stats are provided by third party data sources.

Average Home Value in Chilmark, MA, by Home Size

Currently, there is 1 new listing in Chilmark, MA and 39 homes for sale.

Home Size	Home Value*
2 bedrooms (4 homes)	$1,564,590
3 bedrooms (6 homes)	$2,119,233
4 bedrooms (10 homes)	$2,634,555

*Home value over the past month

What Locals Say about Chilmark

Elaine V.
12y ago
"I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-10-27 09:26:05 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

© 2026 LINK, All Rights Reserved. Data last updated: 2026-10-27 09:56:22 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Chilmark, MA Real Estate & Homes For Sale

39 homes