Real Estate Investment Properties for Sale in Chilmark, MA
Looking for investment property in Chilmark, MA with high ROI ?
Explore a variety of short-term homes & houses in Chilmark, MA. Invest wisely with VRBO & Chilmark, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Chilmark, MA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
16 Shotnaigher LaneChilmark, MANew to market this completely renovated water view home is located in a private enclave of... |
4 beds | 4 baths | 2,050 sq.ft. |
$10,950,000 |
Airbnb cash on cash: -0.93%
|
308 South RdChilmark, MAWaterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilm... |
4 beds | 4 baths | 3,490 sq.ft. |
$7,350,000 |
Airbnb cash on cash: -0.92%
|
18 Spruce Gate RdChilmark, MAWelcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of... |
5 beds | 3 baths | 3,700 sq.ft. |
$12,500,000 |
Airbnb cash on cash: -1.11%
|
47 Quenames RdChilmark, MAOn a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding ... |
2 beds | 1 baths | 924 sq.ft. |
$1,325,000 |
Airbnb cash on cash: -0.81%
|
45 Quenames RdChilmark, MASet on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and ... |
2 beds | 1 baths | 896 sq.ft. |
$1,300,000 |
Airbnb cash on cash: 0.42%
|
8 Snail RdChilmark, MA8 Snail Rd, Chilmark, MA 02535 | Single Family Residential |
6 beds | 7 baths | 6,967 sq.ft. |
$15,400,000 |
Airbnb cash on cash: -2.13%
|
96 Hammett LnChilmark, MA96 Hammett Ln, Chilmark, MA 02535 | Single Family Residential |
3 beds | 2 baths | 3,426 sq.ft. |
$3,795,000 |
Airbnb cash on cash: -1.63%
|
21 & 25 Fulling Mill RdChilmark, MA
|
4 beds | 3 baths | 1,918 sq.ft. |
$2,250,000 |
Airbnb cash on cash: -1.19%
|
61 Stonewall RdChilmark, MAIntroducing a refined contemporary Chilmark beach house with water views and deeded access... |
5 beds | 4 baths | 3,513 sq.ft. |
$5,450,000 |
Airbnb cash on cash: -0.85%
|
132 South RdChilmark, MANestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming Ne... |
3 beds | 3 baths | 2,155 sq.ft. |
$1,600,000 |
Airbnb cash on cash: 0.19%
|
21 Eliot AveChilmark, MAAn iconic retreat in Chilmark, this totally renovated beach house captures sweeping views ... |
4 beds | 3 baths | 2,746 sq.ft. |
$5,250,000 |
Airbnb cash on cash: -0.56%
|
18 Point Inner WayChilmark, MA18 Point Inner Way, Chilmark, MA 02535 | Single Family Residential |
7 beds | 11 baths | 11,200 sq.ft. |
$45,000,000 |
Airbnb cash on cash: -2.19%
|
28 Black Point RdChilmark, MA28 Black Point Rd, Chilmark, MA 02535 | Single Family Residential |
3 beds | 3 baths | 1,469 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -1.47%
|
63 Putnam RdChilmark, MA63 Putnam Rd, Chilmark, MA 02535 | Single Family Residential |
3 beds | 2 baths | 2,095 sq.ft. |
$4,995,000 |
Airbnb cash on cash: -1.85%
|
35 South Bowl RdChilmark, MA35 South Bowl Rd, Chilmark, MA 02535 | Single Family Residential |
3 beds | 2 baths | 2,710 sq.ft. |
$5,400,000 |
Airbnb cash on cash: -1.81%
|
49 Gosnolds WayChilmark, MA49 Gosnolds Way, Chilmark, MA 02535 | Single Family Residential |
5 beds | 3 baths | 4,044 sq.ft. |
$5,200,000 |
Airbnb cash on cash: -1.95%
|
26 Bijahs WayChilmark, MA26 Bijahs Way, Chilmark, MA 02535 | Single Family Residential |
3 beds | 2 baths | 2,510 sq.ft. |
$2,395,000 |
Airbnb cash on cash: -1.35%
|
34 Ebens LnChilmark, MA34 Ebens Ln, Chilmark, MA 02535 | Other |
N/A beds | N/A baths | N/A |
$2,725,000 |
Airbnb cash on cash: -1.68%
|
Real Estate investment in Chilmark, MA
There are 19 properties for sale in the city of Chilmark . The median list price in Chilmark is $3,707,781 and the average price per square foot is $1,090. In August 2026, the average monthly cash on cash return in Chilmark is -1.00%. The average monthly rental income in Chilmark is $3,475.