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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
126 Old Route 55 Pawling, NY Back 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% Traditional cash on cash: 6.9% Airbnb Rental Income: $2384 Traditional Rental Income: $5636 Airbnb ROI: 0.03% Traditional ROI: 6.9%
2 Coburn Road W, Sherman Coburn Road W Pawling, NY Discover 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% Traditional cash on cash: 2.13% Airbnb Rental Income: $2332 Traditional Rental Income: $3793 Airbnb ROI: 0.38% Traditional ROI: 2.13%
Investment Properties for Sale in Other Cities of New-york
15 DEWEY Place New York , NY Welcome to this impeccably rebuilt masterpiece in the historic Stuyvesant Heights section ...	3 beds \| 5 baths \| 2,031 sq.ft.	$1,599,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.93% Airbnb Rental Income: $2152 Traditional Rental Income: $4835 Airbnb ROI: -0.24% Traditional ROI: 1.93%
124 E 28th Street New York , NY Opportunity Awaits in Flatbush! Welcome to this semi-detached single-family home nestled ...	5 beds \| 2 baths \| 1,333 sq.ft.	$649,999	Airbnb cash on cash: 6.83% Traditional cash on cash: 4.14% Airbnb Rental Income: $6559 Traditional Rental Income: $3648 Airbnb ROI: 6.83% Traditional ROI: 4.14%
976 Schenectady Ave New York , NY 976 Schenectady Ave, New York, NY 11203 \| Single Family Residential	4 beds \| 1 baths \| 1,504 sq.ft.	$580,880	Airbnb cash on cash: 9.54% Traditional cash on cash: 3.47% Airbnb Rental Income: $8309 Traditional Rental Income: $3444 Airbnb ROI: 9.54% Traditional ROI: 3.47%
1621 70th St New York , NY Fully detached huge one family home in Bensonhurst. First and second floor a four bedroom ...	4 beds \| 3 baths \| 1,493 sq.ft.	$1,378,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 1.46% Airbnb Rental Income: $10021 Traditional Rental Income: $3917 Airbnb ROI: 4.78% Traditional ROI: 1.46%
30-33 92nd Street New York , NY This beautifully maintained 4-bedroom, 2.5-bathroom home is designed for comfort, flexibil...	4 beds \| 3 baths \| 1,716 sq.ft.	$880,000	Airbnb cash on cash: 7.28% Traditional cash on cash: 2.76% Airbnb Rental Income: $9164 Traditional Rental Income: $3738 Airbnb ROI: 7.28% Traditional ROI: 2.76%
118 Cannon Ave New York , NY Located in the Travis area, this detached bungalow sits on an extra-deep 28' x 155' lot, o...	2 beds \| 1 baths \| 804 sq.ft.	$569,900	Airbnb cash on cash: 4.76% Traditional cash on cash: 1.85% Airbnb Rental Income: $4501 Traditional Rental Income: $2015 Airbnb ROI: 4.76% Traditional ROI: 1.85%
469 Minnieford Ave New York , NY 469 Minnieford Ave, New York, NY 10464 \| Single Family Residential	3 beds \| 2 baths \| 1,630 sq.ft.	$859,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 1.58% Airbnb Rental Income: $1699 Traditional Rental Income: $3528 Airbnb ROI: -1.29% Traditional ROI: 1.58%
64-05 Yellowstone Blvd Ph 509 New York , NY Welcome to this stunning 2-bedroom, 2-bathroom residence at the coveted NOVO 64. Offering ...	2 beds \| 2 baths \| 1,291 sq.ft.	$1,190,000	Airbnb cash on cash: -4.18% Traditional cash on cash: -2.27% Airbnb Rental Income: $1593 Traditional Rental Income: $3258 Airbnb ROI: -4.18% Traditional ROI: -2.27%
53 Gibson Ave New York , NY Welcome to 53 Gibson Avenue, situated on a quiet one-way street. This well-maintained home...	3 beds \| 2 baths \| 1,364 sq.ft.	$899,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 0.65% Airbnb Rental Income: $5662 Traditional Rental Income: $2904 Airbnb ROI: 2.59% Traditional ROI: 0.65%
289 Ocean Ter New York , NY 289 Ocean Ter, New York, NY 10301 \| Single Family Residential	5 beds \| 6 baths \| 7,800 sq.ft.	$3,499,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.23% Airbnb Rental Income: $null Traditional Rental Income: $8154 Airbnb ROI: N/A Traditional ROI: -0.23%
10 Token St New York , NY 10 Token St, New York, NY 10312 \| Single Family Residential	3 beds \| 2 baths \| 1,920 sq.ft.	$819,900	Airbnb cash on cash: 3.1% Traditional cash on cash: 1.08% Airbnb Rental Income: $5662 Traditional Rental Income: $2986 Airbnb ROI: 3.1% Traditional ROI: 1.08%
217-14 133rd Road New York , NY Discover this spectacular luxuriously renovated, turnkey, move in ready massive fully deta...	3 beds \| 4 baths \| 1,638 sq.ft.	$899,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.29% Airbnb Rental Income: $1059 Traditional Rental Income: $3388 Airbnb ROI: -0.93% Traditional ROI: 2.29%
99-03 207th Street New York , NY Welcome to 99-03 207th St, a New construction Detached Single Family house situated in a 5...	5 beds \| 4 baths \| 3,653 sq.ft.	$1,299,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $4817 Airbnb ROI: N/A Traditional ROI: 2.44%
4725 Independence Ave New York , NY 4725 Independence Ave, New York, NY 10471 \| Single Family Residential	7 beds \| 7 baths \| 4,784 sq.ft.	$2,695,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.13% Airbnb Rental Income: $null Traditional Rental Income: $6562 Airbnb ROI: N/A Traditional ROI: -0.13%
6015 Independence Avenue New York , NY Unique 4 bedroom 5 bath cliff-top home in an exclusive North Riverdale enclave. Live perch...	4 beds \| 5 baths \| 2,244 sq.ft.	$1,300,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 2.38% Airbnb Rental Income: $8454 Traditional Rental Income: $5331 Airbnb ROI: 3.64% Traditional ROI: 2.38%

Real Estate investment in Pawling, NY

There are 3 properties for sale in the city of Pawling . The median list price in Pawling is $650,000 and the average price per square foot is $260. In January 2026, the average monthly cash on cash return in Pawling is 4.00%. The average monthly rental income in Pawling is $3,793.

Pawling, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Pawling.

In 2026, the best neighborhood to buy investment property is Pawling.

The ROI for Short-Term is higher than the Long-Term in Pawling with average rental income of $2,332.

Your search for investment property begins and ends here

Investment Property for Sale in Pawling, NY

126 Old Route 55

Pawling, NY

4 beds | 4 baths | 2,361 sq.ft.

$598,500

Airbnb cash on cash: 0.03%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $2384

Traditional Rental Income: $5636

Airbnb ROI: 0.03%

Traditional ROI: 6.9%

2 Coburn Road W, Sherman Coburn Road W

Pawling, NY

3 beds | 2 baths | 2,240 sq.ft.

$1,250,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $2332

Traditional Rental Income: $3793

Airbnb ROI: 0.38%

Traditional ROI: 2.13%

Investment Properties for Sale in Other Cities of New-york

New York , NY

3 beds | 5 baths | 2,031 sq.ft.

$1,599,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $2152

Traditional Rental Income: $4835

Airbnb ROI: -0.24%

Traditional ROI: 1.93%

New York , NY

5 beds | 2 baths | 1,333 sq.ft.

$649,999

Airbnb cash on cash: 6.83%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $6559

Traditional Rental Income: $3648

Airbnb ROI: 6.83%

Traditional ROI: 4.14%

New York , NY

4 beds | 1 baths | 1,504 sq.ft.

$580,880

Airbnb cash on cash: 9.54%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $8309

Traditional Rental Income: $3444

Airbnb ROI: 9.54%

Traditional ROI: 3.47%

New York , NY

4 beds | 3 baths | 1,493 sq.ft.

$1,378,000

Airbnb cash on cash: 4.78%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $10021

Traditional Rental Income: $3917

Airbnb ROI: 4.78%

Traditional ROI: 1.46%

New York , NY

4 beds | 3 baths | 1,716 sq.ft.

$880,000

Airbnb cash on cash: 7.28%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $9164

Traditional Rental Income: $3738

Airbnb ROI: 7.28%

Traditional ROI: 2.76%

New York , NY

2 beds | 1 baths | 804 sq.ft.

$569,900

Airbnb cash on cash: 4.76%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $4501

Traditional Rental Income: $2015

Airbnb ROI: 4.76%

Traditional ROI: 1.85%

New York , NY

3 beds | 2 baths | 1,630 sq.ft.

$859,000

Airbnb cash on cash: -1.29%