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.
Single Family Homes for Sale in Pawling, NY
Search for Single Family Residential for Sale in Pawling, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 17 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| 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%
|