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 |
|---|---|---|---|
36 Byrds Hill RoadPawling, NYSet on a quiet, scenic road in the prestigious Quaker Hill area, this home offers the perf... |
2 beds | 3 baths | 1,820 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.64%
|
36 Elm StreetPawling, NYA historic Village Colonial on a quiet street, is a delight to show. Immaculate, well mai... |
3 beds | 2 baths | 1,680 sq.ft. |
$449,000 |
Airbnb cash on cash: 3.44%
|
5 Red Tail CourtPawling, NYTucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tai... |
5 beds | 3 baths | 2,924 sq.ft. |
$699,000 |
Airbnb cash on cash: -1.01%
|
21 Brady Brook Farm RoadPawling, NYNestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, ... |
4 beds | 4 baths | 4,683 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -0.79%
|
7 Glen CourtPawling, NYWelcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,30... |
3 beds | 3 baths | 2,318 sq.ft. |
$595,000 |
Airbnb cash on cash: 1.77%
|
14 Old Route 55Pawling, NYWelcome home to this historic and charming 3 bedroom, 1 bathroom beauty located above a st... |
3 beds | 1 baths | 1,653 sq.ft. |
$299,950 |
Airbnb cash on cash: 6.19%
|
126 Old Route 55Pawling, NYFULLY AVAIIABLE This house is owned by a church and in New York a sale has to be approved... |
4 beds | 5 baths | 2,361 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.9%
|
85 Harmony Hill RoadPawling, NYThis charming fully remodeled, bright, and sunny ranchâfeaturing 3 bedrooms, 3 full bath... |
3 beds | 3 baths | 1,640 sq.ft. |
$675,000 |
Airbnb cash on cash: 0.76%
|
26 Rodina DrivePawling, NYWelcome to your brand new dream home! Nestled on a beautiful and peaceful two and half ac... |
4 beds | 3 baths | 3,200 sq.ft. |
$869,000 |
Airbnb cash on cash: 0.4%
|
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: -2.21%
|
51 Estate DrivePawling, NYDon't miss this opportunity to have your dream home built and custom designed to your fini... |
5 beds | 4 baths | 3,500 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.21%
|
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. |
$348,888 |
Airbnb cash on cash: 4.51%
|
27 Millstream CourtPawling, NYWelcome to your new home in the neighborhood you want and with all the amenities you want.... |
4 beds | 3 baths | 3,283 sq.ft. |
$734,900 |
Airbnb cash on cash: 0.93%
|
19 Cushing Green S.Pawling, NYComfortable Townhouse Living at Squire Green Welcome to this spacious and bright end-unit ... |
3 beds | 3 baths | 1,835 sq.ft. |
$456,600 |
Airbnb cash on cash: 2.32%
|
28 Gobblers Knob RoadPawling, NYWelcome to 28 Gobblers Knob Road â A Hudson Valley Retreat! Nestled in the heart of the ... |
3 beds | 2 baths | 2,107 sq.ft. |
$649,900 |
Airbnb cash on cash: 2.07%
|
175 Old Quaker Hill RoadPawling, NYA Stately Cape Cod Estate with Exceptional Potential awaits. Set on an expansive, flat pa... |
4 beds | 5 baths | 4,018 sq.ft. |
$699,000 |
Airbnb cash on cash: -0.61%
|
33 Grandview AvenuePawling, NYCharming Cape Cod in the village of Pawling, one owner since it was built in 1953. The hom... |
4 beds | 1 baths | 1,157 sq.ft. |
$395,000 |
Airbnb cash on cash: 4.48%
|
36 Spruce Street #36Pawling, NYComfortable Townhouse Living at Cedar Valley 36 Spruce Street, Pawling, NY located in ced... |
2 beds | 3 baths | 1,414 sq.ft. |
$335,000 |
Airbnb cash on cash: 1.3%
|
7 Elm StreetPawling, NYHistorical Home in the Village of Pawling - Come make this your special home - 3 Bedrooms,... |
3 beds | 2 baths | 1,800 sq.ft. |
$319,000 |
Airbnb cash on cash: 5.88%
|
Real Estate investment in Pawling, NY
There are 19 properties for sale in the city of Pawling . The median list price in Pawling is $599,000 and the average price per square foot is $241. In September 2025, the average monthly cash on cash return in Pawling is 4.00%. The average monthly rental income in Pawling is $3,477.