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: 1.88%
|
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: 0.64%
|
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: 4.29%
|
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: -0.25%
|
126 Old Route 55Pawling, NYBack on the market, the deal fell through from the buyer side. 9/17/2025 This house is... |
4 beds | 5 baths | 2,361 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.45%
|
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. |
$650,000 |
Airbnb cash on cash: -0.26%
|
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. |
$859,000 |
Airbnb cash on cash: -0.6%
|
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: -2.26%
|
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: 1.63%
|
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: -0.42%
|
27 Millstream CourtPawling, NYFULLY AVAILABLE. BUYER WAS UNABLE TO SECURE FINANCING (10/6/25). These remarks will be upd... |
4 beds | 3 baths | 3,283 sq.ft. |
$734,900 |
Airbnb cash on cash: -0.25%
|
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. |
$599,900 |
Airbnb cash on cash: 1.15%
|
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: -1.85%
|
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: 0.25%
|
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: -0.21%
|
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: 0.36%
|
48 W Main StreetPawling, NY19th Century Colonial/Farmhouse completely remodeled in 2025. EVERYTHING is brand new. Les... |
5 beds | 4 baths | 3,152 sq.ft. |
$699,900 |
Airbnb cash on cash: 2.12%
|
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 $259. In October 2025, the average monthly cash on cash return in Pawling is 4.00%. The average monthly rental income in Pawling is $4,508.