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: 1.34%
|
13 Cushing Grn SPawling, NYA rare find and an incredible opportunity awaits in Squire Green with this two-story end-u... |
2 beds | 2 baths | 1,567 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.8%
|
16 Anderson RdPawling, NYBrand new and finished to perfection. You'll not need to lift a finger to prepare this hom... |
4 beds | 6 baths | 3,012 sq.ft. |
$1,175,000 |
Airbnb cash on cash: 0.21%
|
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. |
$299,500 |
Airbnb cash on cash: 3.06%
|
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 | 4 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: -0.63%
|
26 Rodina DrPawling, NYBe the first to live in this stunning four bedroom, two and a half bath home nestled on a ... |
4 beds | 2 baths | 3,200 sq.ft. |
$799,000 |
Airbnb cash on cash: -0.7%
|
21 Kings WayPawling, NYWelcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderfu... |
3 beds | 2 baths | 1,960 sq.ft. |
$368,888 |
Airbnb cash on cash: 1.66%
|
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%
|
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: -0.36%
|
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: -0.69%
|
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%
|
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%
|
64 S Quaker Hill RdPawling, 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. |
$1,200,000 |
Airbnb cash on cash: -1.59%
|
16 Townsend BoulevardPawling, NYWelcome to 16 Townsend Blvd, a lovely brick home set in the heart of picturesque Pawling, ... |
2 beds | 1 baths | 1,080 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.58%
|
215 Little Pond RdPawling, NY215 Little Pond Rd, Pawling, NY 12564 | Single Family Residential |
5 beds | N/A baths | 1,062 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.84%
|
20 Hickory LnPawling, NY20 Hickory Ln, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$150,000 |
Airbnb cash on cash: 7.71%
|
Real Estate investment in Pawling, NY
There are 30 properties for sale in the city of Pawling . The median list price in Pawling is $449,500 and the average price per square foot is $198. In February 2026, the average monthly cash on cash return in Pawling is 3.00%. The average monthly rental income in Pawling is $3,066.