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 |
|---|---|---|---|
5 Old Field CirclePawling, NYWelcome to this beautifully maintained Victorian-style home, ideally situated in the highl... |
3 beds | 3 baths | 2,104 sq.ft. |
$549,222 |
Airbnb cash on cash: 0.41%
|
188 N Quaker Hill RoadPawling, NYFantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.... |
3 beds | 3 baths | 2,636 sq.ft. |
$595,000 |
Airbnb cash on cash: 1.13%
|
5 Red Tail CourtPawling, NYTucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tai... |
4 beds | 2 baths | 2,924 sq.ft. |
$600,000 |
Airbnb cash on cash: -0.9%
|
921 W Dover RdPawling, NYCustom Quality Built Ranch nestled on 8+ private acres. One level living at its best in a ... |
3 beds | 3 baths | 3,629 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.34%
|
15 Dykeman StPawling, NYFantastic vacant lot available on a dead end street. Just minutes from the Village of Pawl... |
N/A beds | N/A baths | N/A |
$215,000 |
Airbnb cash on cash: 4.63%
|
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: -2.31%
|
104 N Garden DrPawling, NY104 North Garden Dr, Pawling, NY 12564 | Single Family Residential |
9 beds | 9 baths | 55,000 sq.ft. |
$39,000,000 |
Airbnb cash on cash: -2.67%
|
120 Harmony RdPawling, NY120 Harmony Rd, Pawling, NY 12564 | Single Family Residential |
5 beds | 4 baths | 3,920 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -1.21%
|
178 Charles Colman BlvdPawling, NY178 Charles Colman Blvd, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$1,350,000 |
Airbnb cash on cash: -1.52%
|
225 Route 22Pawling, NY225 Route 22, Pawling, NY 12564 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$9,750,000 |
Airbnb cash on cash: -2.55%
|
Lot C Oblong LnPawling, NYLot C Oblong Ln, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$190,000 |
Airbnb cash on cash: 5.58%
|
Lot 25 Brady Brook Farm RdPawling, NYLot 25 Brady Brook Farm Rd, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$229,000 |
Airbnb cash on cash: 2.91%
|
Lot 21 Cox RdPawling, NYLot 21 Cox Rd, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$229,000 |
Airbnb cash on cash: 2.91%
|
Walnut StPawling, NYWalnut St, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$135,000 |
Airbnb cash on cash: 8.83%
|
20 Hickory LnPawling, NY20 Hickory Ln, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$140,000 |
Airbnb cash on cash: 8.43%
|
128 Old Pawling RdPawling, NY128 Old Pawling Rd, Pawling, NY 12564 | Single Family Residential |
4 beds | 3 baths | 3,434 sq.ft. |
$900,000 |
Airbnb cash on cash: -0.7%
|
17 Townsend BlvdPawling, NY17 Townsend Blvd, Pawling, NY 12564 | Single Family Residential |
2 beds | 2 baths | 1,088 sq.ft. |
$495,000 |
Airbnb cash on cash: -0.73%
|
3302 Route 55Pawling, NY3302 Route 55, Pawling, NY 12564 | Single Family Residential |
6 beds | 6 baths | 6,625 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -1.96%
|
168 Old Route 55Pawling, NYStep into the year our nation was born and own a piece of living American history. Origina... |
2 beds | 2 baths | 2,194 sq.ft. |
$565,000 |
Airbnb cash on cash: -1.29%
|
1 Cushing Green NPawling, NYThis great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attac... |
2 beds | 3 baths | 1,567 sq.ft. |
$335,000 |
Airbnb cash on cash: -2.12%
|
194 South RdPawling, NY194 South Rd, Pawling, NY 12531 | Single Family Residential |
4 beds | 3 baths | 3,768 sq.ft. |
$990,000 |
Airbnb cash on cash: -0.88%
|
Lakeview DrPawling, NYLakeview Dr, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$79,000 |
Airbnb cash on cash: 5.1%
|
58 Pine DrivePawling, NYTucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.8... |
3 beds | 2 baths | 1,706 sq.ft. |
$530,000 |
Airbnb cash on cash: 1.75%
|
16 Juniper LanePawling, NYWelcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and c... |
2 beds | 2 baths | 1,639 sq.ft. |
$385,000 |
Airbnb cash on cash: -1.62%
|
Old Quaker Hill RdPawling, NYOld Quaker Hill Rd, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$999,000 |
Airbnb cash on cash: -1.11%
|
1141 Old Quaker Hill RoadPawling, NYWelcome Home! Tucked away along storied Old Quaker Hill, this antique charmer invites you ... |
2 beds | 1 baths | 1,347 sq.ft. |
$499,999 |
Airbnb cash on cash: -0.29%
|
34 Meeting House RoadPawling, NYNestled in the heart of historic Quaker Hill, this bucolic property offers timeless charm ... |
3 beds | 4 baths | 2,292 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -1.36%
|
103 S Harmony Hill RoadPawling, NYProperties like this don't come along often! As you turn off the road, the world quiets. T... |
3 beds | 3 baths | 3,729 sq.ft. |
$775,000 |
Airbnb cash on cash: 0.15%
|
117 S Quaker Hill RoadPawling, NYTucked away on historic Quaker Hill - known for its picturesque horse farms and country es... |
2 beds | 2 baths | 2,278 sq.ft. |
$859,000 |
Airbnb cash on cash: -1.77%
|
57 Buhleir RdPawling, NY57 Buhleir Rd, Pawling, NY 12564 | Single Family Residential |
3 beds | 2 baths | 1,768 sq.ft. |
$629,900 |
Airbnb cash on cash: 1.08%
|
41 and 43 Meeting House RdPawling, NY41 and 43 Meeting House Rd, Pawling, NY 12564 | Single Family Residential |
5 beds | 5 baths | 5,390 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -1.67%
|
978 W Dover RoadPawling, NYWelcome to 978 W Dover Road in Pawling, NY-where comfort, space, and scenic beauty come to... |
3 beds | 3 baths | 1,556 sq.ft. |
$440,000 |
Airbnb cash on cash: 2.93%
|
24 Overlook DrivePawling, NYTucked away on nearly two private acres, this inviting and versatile home offers the perfe... |
3 beds | 4 baths | 3,175 sq.ft. |
$689,000 |
Airbnb cash on cash: 0.39%
|
6 Martingale WayPawling, NYWelcome to 6 Martingale Way, an impressive 4-bedroom, 3.5-bathroom colonial offering nearl... |
4 beds | 4 baths | 4,687 sq.ft. |
$750,000 |
Airbnb cash on cash: -1.08%
|
12 John Kane CourtPawling, NYIt's the townhome in Deerfield Ponds you have been waiting for. The most sought-after layo... |
3 beds | 3 baths | 1,920 sq.ft. |
$460,000 |
Airbnb cash on cash: 1.22%
|
37 W Deer TrlPawling, NY37 W Deer Trl, Pawling, NY 12564 | Single Family Residential |
3 beds | 1 baths | 1,955 sq.ft. |
$525,000 |
Airbnb cash on cash: 0.79%
|
809 Quaker Hill RdPawling, NY809 Quaker Hill Rd, Pawling, NY 12564 | Single Family Residential |
3 beds | 3 baths | 3,600 sq.ft. |
$3,100,000 |
Airbnb cash on cash: -1.94%
|
618 Quaker Hill RdPawling, NY618 Quaker Hill Rd, Pawling, NY 12564 | Single Family Residential |
8 beds | 9 baths | 15,000 sq.ft. |
$5,000,000 |
Airbnb cash on cash: -2.34%
|
0 Marble LnPawling, NY0 Marble Ln, Pawling, NY 12564 | Other |
N/A beds | N/A baths | N/A |
$249,000 |
Airbnb cash on cash: 3.18%
|
3120 Route 55Pawling, NY3120 Route 55, Pawling, NY 12564 | Single Family Residential |
3 beds | 3 baths | 2,724 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.71%
|
Real Estate investment in Pawling, NY
There are 40 properties for sale in the city of Pawling . The median list price in Pawling is $614,950 and the average price per square foot is $125. In June 2026, the average monthly cash on cash return in Pawling is 2.00%. The average monthly rental income in Pawling is $3,199.