Real Estate Investment Properties for Sale in Pawling, NY
Looking for investment property in Pawling, NY with high ROI ?
Explore a variety of short-term homes & houses in Pawling, NY. Invest wisely with VRBO & Pawling, NY 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 Pawling, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1125 Old Quaker Hill RoadPawling, NYTucked away in the prestigious Quaker Hill area of Pawling, this cozy ranch-style country ... |
3 beds | 2 baths | 2,048 sq.ft. |
$875,000 |
Airbnb cash on cash: -1.27%
|
13 Cushing Green SPawling, NYA rare find and an incredible opportunity awaits in Squire Green with this two-story end-u... |
2 beds | 3 baths | 1,567 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.5%
|
14 Old Route 55Pawling, NYWelcome HOME to this charming and historic 3-bedroom, 1-bath residence located in the hear... |
3 beds | 1 baths | 1,653 sq.ft. |
$269,950 |
Airbnb cash on cash: 2.72%
|
126 Old Route 55Pawling, NYBack on the market, the deal fell through from the buyer side. 9/17/2025 This house is own... |
4 beds | 5 baths | 2,361 sq.ft. |
$598,500 |
Airbnb cash on cash: -0.73%
|
7 Juniper LanePawling, NYWelcome home to your spacious and cozy tri-level end unit in the Cedar Valley complex! The... |
2 beds | 2 baths | 2,596 sq.ft. |
$420,000 |
Airbnb cash on cash: -0.52%
|
26 Rodina DrivePawling, NYBe the first to live in this stunning four bedroom, two and a half bath home nestled on a ... |
4 beds | 3 baths | 3,200 sq.ft. |
$799,000 |
Airbnb cash on cash: -1.28%
|
15 Kirby Hill RoadPawling, NYKirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest... |
4 beds | 4 baths | 3,942 sq.ft. |
$14,995,000 |
Airbnb cash on cash: -2.34%
|
21 Kings WayPawling, NYWelcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderfu... |
3 beds | 3 baths | 1,960 sq.ft. |
$368,888 |
Airbnb cash on cash: 1.09%
|
4 Mane WayPawling, NYElegant and Updated Center Hall Colonial, ideally situated in The Highlands-a beautiful an... |
4 beds | 3 baths | 3,611 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.72%
|
64 S Quaker Hill RoadPawling, NYWelcome to Country Living at Its Finest! Nestled on 24.5 scenic acres, this classic 1910 f... |
5 beds | 4 baths | 4,248 sq.ft. |
$1,175,000 |
Airbnb cash on cash: -2.99%
|
40 Walnut StreetPawling, NYSpacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful wes... |
4 beds | 2 baths | 1,776 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.3%
|
168 Old Route 55Pawling, NYStep into the very year our nation was born and own a piece of American history! Originall... |
2 beds | 2 baths | 2,196 sq.ft. |
$599,000 |
Airbnb cash on cash: -0.88%
|
20 Saratoga StreetPawling, NYWelcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Dee... |
3 beds | 4 baths | 2,503 sq.ft. |
$485,000 |
Airbnb cash on cash: 0.37%
|
1 Cushing Green NPawling, NYThis great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attac... |
2 beds | 3 baths | 1,567 sq.ft. |
$345,000 |
Airbnb cash on cash: -0.65%
|
58 Pine DrivePawling, NYTucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.8... |
3 beds | 2 baths | 1,706 sq.ft. |
$530,000 |
Airbnb cash on cash: 0.2%
|
Real Estate investment in Pawling, NY
There are 16 properties for sale in the city of Pawling . The median list price in Pawling is $598,500 and the average price per square foot is $224. In April 2026, the average monthly cash on cash return in Pawling is 3.00%. The average monthly rental income in Pawling is $3,182.