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 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: 1.35%
|
7 Glen CourtPawling, NYWelcome to this exquisitely renovated 3-bedroom, 2.5-bath Colonial home, showcasing over 2... |
3 beds | 3 baths | 2,318 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.23%
|
14 Old Route 55Pawling, NYFULLY Available! Welcome home to this historic and charming 3 bedroom, 1 bathroom beauty ... |
3 beds | 1 baths | 1,653 sq.ft. |
$275,000 |
Airbnb cash on cash: 3.44%
|
29 Cunningham LanePawling, NYHarmony Woods, an enclave of beautiful homes on the outskirts of the Village. This contemp... |
4 beds | 5 baths | 4,199 sq.ft. |
$699,000 |
Airbnb cash on cash: -0.61%
|
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: 0.03%
|
85 Harmony Hill RoadPawling, NYThis charming fully remodeled, bright, and sunny ranch-featuring 3 bedrooms, 3 full bathro... |
3 beds | 3 baths | 1,640 sq.ft. |
$650,000 |
Airbnb cash on cash: -0.62%
|
26 Rodina DrivePawling, NYWelcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acr... |
4 beds | 3 baths | 3,200 sq.ft. |
$799,000 |
Airbnb cash on cash: -0.7%
|
94 S Quaker Hill RoadPawling, NYSet on 3.62 acres of picturesque and private land, this expansive 4-bedroom split-level ho... |
4 beds | 3 baths | 3,360 sq.ft. |
$749,000 |
Airbnb cash on cash: -0.76%
|
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: -0.59%
|
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. |
$574,900 |
Airbnb cash on cash: 0.83%
|
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: -2.21%
|
33 Spruce StreetPawling, NYWelcome to 33 Spruce Lane, a charming 2-bedroom, 2.5-bath home located in the sought-after... |
2 beds | 3 baths | 1,413 sq.ft. |
$359,999 |
Airbnb cash on cash: -0.19%
|
27 Washington CourtPawling, NYWelcome to 27 Washington Court, located in the sought-after Deerfield Ponds community! Thi... |
2 beds | 3 baths | 2,072 sq.ft. |
$450,000 |
Airbnb cash on cash: -0.56%
|
48 David LanePawling, NYEnjoy private, direct lakefront access and stunning views from this chic 3-bedroom, 2.5-ba... |
3 beds | 3 baths | 1,788 sq.ft. |
$695,000 |
Airbnb cash on cash: 0.01%
|
48 W Main StreetPawling, NYThe PERFECT location for a Weekend/Vacation home or Extended/Large Family. 19th Century Co... |
5 beds | 4 baths | 3,152 sq.ft. |
$699,900 |
Airbnb cash on cash: 0.78%
|
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: -1.13%
|
2 Coburn Road W,Sherman Coburn Road WPawling, NYDiscover the rare opportunity to build your custom modern ranch in the tranquil countrysid... |
3 beds | 2 baths | 2,240 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 0.38%
|
Real Estate investment in Pawling, NY
There are 17 properties for sale in the city of Pawling . The median list price in Pawling is $695,000 and the average price per square foot is $268. In December 2025, the average monthly cash on cash return in Pawling is 4.00%. The average monthly rental income in Pawling is $3,886.