Up-Island Regional School District Real Estate & Homes For Sale

93 homes

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NEW - 1 DAY AGO
5.4 ACRES
$2,950,000
3 Beds
3 Baths
1,469 sqft
28 Black Point Road,
Chilmark, MA 02535
Island Real Estate
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NEW - 2 DAYS AGO
2 ACRES
$1,600,000
4 Beds
3 Baths
2,334 sqft
150 Field View Ln,
West Tisbury, MA 02575
Island Real Estate
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OPEN SAT, 10-12PM
0.92 ACRES
$1,225,000
3 Beds
2 Baths
1,800 sqft
52 Oak Knoll Rd,
West Tisbury, MA 02575
Donnelly + Co
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2 ACRES
$3,600,000
6 Beds
6 Baths
4,104 sqft
12 Brook Hollow Rd,
West Tisbury, MA 02575
Conroy & Company R.E., Inc.
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OPEN SAT, 11-12:30PM
7.52 ACRES
$3,995,000
6 Beds
3.5 Baths
3,070 sqft
30-40 Elias Ln,
West Tisbury, MA 02575
Tea Lane Associates
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OPEN SUN, 12-2PM
1.9 ACRES
$1,600,000
3 Beds
3 Baths
2,155 sqft
132 South Rd,
Chilmark, MA 02535
Signal House Group at Compass
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2.1 ACRES
$799,000
42 Field View Ln,
West Tisbury, MA 02575
Tea Lane Associates
2.2 ACRES
$3,495,000
4 Beds
4 Baths
3,000 sqft
64 Christiantown Rd,
West Tisbury, MA 02575
Karen M. Overtoom R.E.
3.6 ACRES
$3,750,000
131 Pond View Farm Rd,
West Tisbury, MA 02575
Tea Lane Associates
0.5 ACRES
$1,550,000
4 Beds
2 Baths
1,757 sqft
8 Rumpus Ridge Rd,
Chilmark, MA 02535
Flanders Real Estate
4.8 ACRES
$2,195,000
3 Beds
3 Baths
2,363 sqft
139 Tea Ln,
Chilmark, MA 02535
Tea Lane Associates
1.6 ACRES
$1,399,000
2 Beds
1 Bath
1,996 sqft
29 Scotchmans Ln,
West Tisbury, MA 02575
Island Real Estate
3.42 ACRES
$1,200,000
23 Onkokemmy Rd,
West Tisbury, MA 02575
Sandpiper Realty
0.27 ACRES
$1,550,000
3 Beds
2.5 Baths
1,593 sqft
832 State Rd,
Aquinnah, MA 02535
Gay Head Realty
9.61 ACRES
$15,400,000
6 Beds
8 Baths
6,967 sqft
8 Snail Road,
Chilmark, MA 02535
Corcoran Property Advisors
OPEN SAT, 10-12PM
1.6 ACRES
$1,399,000
4 Beds
2 Baths
1,436 sqft
145 Vineyard Meadow Fms Rd,
West Tisbury, MA 02575
Ocean Park Realty Inc
$1,175,000
4 Beds
2 Baths
2,059 sqft
4 Rock Pond Rd,
West Tisbury, MA 02575
Compass | Point B
3D VIEW
3.4 ACRES
$7,350,000
4 Beds
4.5 Baths
3,490 sqft
308 South Road,
Chilmark, MA 02535
Wallace & Co. Sotheby's International Realty
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
$5,400,000
3 Beds
2 Baths
2,710 sqft
35 S Bowl Rd,
Chilmark, MA 02535
Donnelly + Co
$4,350,000
3 Beds
2 Baths
1,260 sqft
131 State Rd,
Chilmark, MA 02535
Feiner Real Estate
3D VIEW
4.38 ACRES
$2,995,000
4 Beds
3.5 Baths
2,515 sqft
300 North Road 18 Belhaven Way,
Chilmark, MA 02535
Wallace & Co. Sotheby's
16.96 ACRES
$6,950,000
7 Beds
4.5 Baths
6,921 sqft
19 Locust Lane,
Aquinnah, MA 02535
eXp Realty, LLC
3D VIEW
3.4 ACRES
$4,995,000
3 Beds
3 Baths
2,095 sqft
63 Putnam Rd,
Chilmark, MA 02535
Compass | Point B
3D VIEW
1.7 ACRES
$4,000,000
5 Beds
3 Baths
2,304 sqft
41 Moshup Trl,
Aquinnah, MA 02535
Tea Lane Associates
1.9 ACRES
$1,250,000
15 Menemsha Inn Rd,
Chilmark, MA 02535
Tea Lane Associates
5 ACRES
$3,400,000
4 Beds
2.5 Baths
2,383 sqft
100 Gosnolds Way,
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
1 ACRE
$5,500,000
2 Beds
1 Bath
808 sqft
17 Chockers Ln,
Chilmark, MA 02535
Flanders Real Estate
4.51 ACRES
$3,600,000
5 Beds
3 Baths
2,701 sqft
20 James Pond Way,
West Tisbury, MA 02575
Island Real Estate
OPEN SAT, 10-12PM
3.1 ACRES
$4,125,000
7 Beds
4.5 Baths
3,312 sqft
31 Josiah Sachem Way,
West Tisbury, MA 02575
Studio Realty
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
5.45 ACRES
$2,475,000
4 Beds
4 Baths
2,250 sqft
14 Ephriam Allen Rd,
West Tisbury, MA 02575
Tea Lane Associates
0.9 ACRES
$1,450,000
3 Beds
2 Baths
1,749 sqft
10 Abels Neck Rd,
Chilmark, MA 02535
Flanders Real Estate
5.7 ACRES
$1,195,000
14 Ridge Rd,
Aquinnah, MA 02535
Tea Lane Associates
4.5 ACRES
$5,450,000
5 Beds
4 Baths
3,513 sqft
61 Stonewall Road,
Chilmark, MA 02535
Wallace & Co. Sotheby's International Realty
0.4 ACRES
$1,400,000
4 Beds
3 Baths
2,345 sqft
318 Lamberts Cove Rd,
West Tisbury, MA 02575
Tashmoo Realty
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
1.2 ACRES
$2,395,000
3 Beds
2 Baths
2,510 sqft
26 Bijahs Way,
Chilmark, MA 02535
Karen M. Overtoom R.E.
17.16 ACRES
$5,295,000
4 Beds
3 Baths
3,432 sqft
44 Cencelle St,
Chilmark, MA 02535
Tea Lane Associates

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 2022-04-05 08:58:10 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2022© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

© 2026 LINK, All Rights Reserved. Data last updated: 2026-07-15 10:47:55 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.

Up-Island Regional School District Real Estate & Homes For Sale

93 homes

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