Airbnb Properties for Sale in Pawling, NY

Looking for a vacation rental investment in Pawling, NY with high ROI ?

Explore a range of newly added short-term rental homes in Pawling, NY. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Pawling, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6 Byrds Hill Rd Pawling, NY Eighteenth century farmhouse set on 2.7 acres on Quaker Hill, waiting for a lover of antiq...	3 beds \| 2 baths \| 3,035 sq.ft.	$995,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 0.92% Airbnb Rental Income: $4478 Traditional Rental Income: $3028 Airbnb ROI: 1.47% Traditional ROI: 0.92%
140 Hurds Corners Rd Pawling, NY Wonderful light-filled home enjoys a pretty, private setting w/truly gorgeous property, in...	3 beds \| 2 baths \| 1,329 sq.ft.	$599,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.94% Airbnb Rental Income: $4478 Traditional Rental Income: $3131 Airbnb ROI: 3.68% Traditional ROI: 2.94%
921 W Dover Rd Pawling, NY Custom 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: 3.22% Traditional cash on cash: 3.16% Airbnb Rental Income: $4478 Traditional Rental Income: $3505 Airbnb ROI: 3.22% Traditional ROI: 3.16%
Lot C Oblong Ln Pawling, NY Lot C Oblong Ln, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$190,000	Airbnb cash on cash: 5.58% Traditional cash on cash: 3.53% Airbnb Rental Income: $2129 Traditional Rental Income: $1215 Airbnb ROI: 5.58% Traditional ROI: 3.53%
Lot 25 Brady Brook Farm Rd Pawling, NY Lot 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% Traditional cash on cash: 0.64% Airbnb Rental Income: $2129 Traditional Rental Income: $1093 Airbnb ROI: 2.91% Traditional ROI: 0.64%
Lot 21 Cox Rd Pawling, NY Lot 21 Cox Rd, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$229,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 0.63% Airbnb Rental Income: $2129 Traditional Rental Income: $1091 Airbnb ROI: 2.91% Traditional ROI: 0.63%
Walnut St Pawling, NY Walnut St, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: 9.72% Traditional cash on cash: 6.38% Airbnb Rental Income: $2129 Traditional Rental Income: $1183 Airbnb ROI: 9.72% Traditional ROI: 6.38%
20 Hickory Ln Pawling, NY 20 Hickory Ln, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$140,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 4.03% Airbnb Rental Income: $2129 Traditional Rental Income: $995 Airbnb ROI: 8.43% Traditional ROI: 4.03%
Lakeview Dr Pawling, NY Lakeview Dr, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$79,000	Airbnb cash on cash: 5.1% Traditional cash on cash: -1.25% Airbnb Rental Income: $2129 Traditional Rental Income: $1091 Airbnb ROI: 5.1% Traditional ROI: -1.25%
Prospect Street Pawling, NY TO BE BUILT - Build your dream home in the charming Village of Pawling! Ideally located ju...	3 beds \| 3 baths \| 1,652 sq.ft.	$619,900	Airbnb cash on cash: 3.25% Traditional cash on cash: -0.79% Airbnb Rental Income: $4478 Traditional Rental Income: $1201 Airbnb ROI: 3.25% Traditional ROI: -0.79%
103 S Harmony Hill Road Pawling, NY Properties 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: 1.84% Traditional cash on cash: 1.67% Airbnb Rental Income: $4478 Traditional Rental Income: $3420 Airbnb ROI: 1.84% Traditional ROI: 1.67%
57 Buhleir Rd Pawling, NY 57 Buhleir Rd, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 1,768 sq.ft.	$619,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.31% Airbnb Rental Income: $4478 Traditional Rental Income: $2999 Airbnb ROI: 3.25% Traditional ROI: 2.31%
978 W Dover Road Pawling, NY Welcome 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: 5.9% Traditional cash on cash: 5.11% Airbnb Rental Income: $4478 Traditional Rental Income: $3215 Airbnb ROI: 5.9% Traditional ROI: 5.11%
0 Prospect St Pawling, NY 0 Prospect St, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 1,652 sq.ft.	$619,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.44% Airbnb Rental Income: $4478 Traditional Rental Income: $3074 Airbnb ROI: 3.25% Traditional ROI: 2.44%
357 W Dover Rd Pawling, NY 357 W Dover Rd, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 2,137 sq.ft.	$365,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 5.8% Airbnb Rental Income: $4478 Traditional Rental Income: $3004 Airbnb ROI: 7.37% Traditional ROI: 5.8%
17 Spring St Pawling, NY 17 Spring St, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 2,202 sq.ft.	$575,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.61% Airbnb Rental Income: $4478 Traditional Rental Income: $2947 Airbnb ROI: 3.72% Traditional ROI: 2.61%
Woodin Ln Pawling, NY Woodin Ln, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 3.87% Airbnb Rental Income: $2129 Traditional Rental Income: $1186 Airbnb ROI: 6.26% Traditional ROI: 3.87%
21 Overlook Dr Pawling, NY 21 Overlook Dr, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 1,460 sq.ft.	$699,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.57% Airbnb Rental Income: $4478 Traditional Rental Income: $2879 Airbnb ROI: 2.58% Traditional ROI: 1.57%
66 Reservoir Rd Pawling, NY 66 Reservoir Rd, Pawling, NY 12564 \| Single Family Residential	3 beds \| 3 baths \| 1,950 sq.ft.	$525,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.05% Airbnb Rental Income: $4478 Traditional Rental Income: $3409 Airbnb ROI: 4.32% Traditional ROI: 4.05%
49 Millstream Ct Pawling, NY 49 Millstream Ct, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 2,737 sq.ft.	$699,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.76% Airbnb Rental Income: $4478 Traditional Rental Income: $3005 Airbnb ROI: 2.58% Traditional ROI: 1.76%
46 Harmony Hill Rd Pawling, NY 46 Harmony Hill Rd, Pawling, NY 12564 \| Single Family Residential	3 beds \| 2 baths \| 1,828 sq.ft.	$589,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 2.48% Airbnb Rental Income: $4478 Traditional Rental Income: $2943 Airbnb ROI: 3.57% Traditional ROI: 2.48%
00 Route 55 Pawling, NY 00 Route 55, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.1% Airbnb Rental Income: $2129 Traditional Rental Income: $1165 Airbnb ROI: 2.58% Traditional ROI: 1.1%
0 Route 55 Pawling, NY 0 Route 55, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 1.85% Airbnb Rental Income: $2129 Traditional Rental Income: $1165 Airbnb ROI: 3.63% Traditional ROI: 1.85%

Vacation Rentals in Pawling

There are 23 vacation rental properties available for sale in the city of Pawling . The median list price of Airbnb properties available for sale in Pawling is $486,894 and the average price per square foot is $176. The cash on cash return on vacation rentals in Pawling is 2.00%. The average monthly short term rental income in Pawling is $2,372.

Pawling, NY Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 23 Airbnb properties available for sale in Pawling.

In 2026, the best neighborhood to buy short term rental property is Pawling.

In September 2026, the average Airbnb occupancy rate in Pawling is 24%.

Airbnb data on vacation rentals in Pawling, NY is available at Mashvisor. You can access data such as listings, real-time pricing trends, Pawling, NY market insights, guest information and booking details, seasonality trends and historical Pawling, NY Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Pawling, NY

6 Byrds Hill Rd

Pawling, NY

3 beds | 2 baths | 3,035 sq.ft.

$995,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 0.92%

Airbnb Rental Income: $4478

Traditional Rental Income: $3028

Airbnb ROI: 1.47%

Traditional ROI: 0.92%

140 Hurds Corners Rd

Pawling, NY

3 beds | 2 baths | 1,329 sq.ft.

$599,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $4478

Traditional Rental Income: $3131

Airbnb ROI: 3.68%

Traditional ROI: 2.94%

921 W Dover Rd

Pawling, NY

3 beds | 3 baths | 3,629 sq.ft.

$699,000

Airbnb cash on cash: 3.22%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $4478

Traditional Rental Income: $3505

Airbnb ROI: 3.22%

Traditional ROI: 3.16%

Lot C Oblong Ln

Pawling, NY

N/A beds | N/A baths | N/A

$190,000

Airbnb cash on cash: 5.58%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2129

Traditional Rental Income: $1215

Airbnb ROI: 5.58%

Traditional ROI: 3.53%

Lot 25 Brady Brook Farm Rd

Pawling, NY

N/A beds | N/A baths | N/A

$229,000

Airbnb cash on cash: 2.91%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $2129

Traditional Rental Income: $1093

Airbnb ROI: 2.91%

Traditional ROI: 0.64%

Lot 21 Cox Rd

Pawling, NY

N/A beds | N/A baths | N/A

$229,000

Airbnb cash on cash: 2.91%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $2129

Traditional Rental Income: $1091

Airbnb ROI: 2.91%

Traditional ROI: 0.63%

Walnut St

Pawling, NY

N/A beds | N/A baths | N/A

$125,000

Airbnb cash on cash: 9.72%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $2129

Traditional Rental Income: $1183

Airbnb ROI: 9.72%

Traditional ROI: 6.38%

20 Hickory Ln

Pawling, NY

N/A beds | N/A baths | N/A

$140,000

Airbnb cash on cash: 8.43%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $2129

Traditional Rental Income: $995

Airbnb ROI: 8.43%