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 15 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Old Field Circle Pawling, NY Welcome 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: -0.16% Traditional cash on cash: 4.05% Airbnb Rental Income: $2089 Traditional Rental Income: $3710 Airbnb ROI: -0.16% Traditional ROI: 4.05%
13 Cushing Green S Pawling, NY A rare find and an incredible opportunity awaits in Squire Green with this two-story end-u...	2 beds \| 3 baths \| 1,567 sq.ft.	$425,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.38% Airbnb Rental Income: $1988 Traditional Rental Income: $3014 Airbnb ROI: -0.51% Traditional ROI: 3.38%
7 Juniper Lane Pawling, NY Welcome home to your spacious and cozy tri-level end unit in the Cedar Valley complex! The...	2 beds \| 2 baths \| 2,596 sq.ft.	$420,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.45% Airbnb Rental Income: $1988 Traditional Rental Income: $3033 Airbnb ROI: -0.53% Traditional ROI: 3.45%
26 Rodina Drive Pawling, NY Be the first to live in this stunning four bedroom, two and a half bath home nestled on a ...	4 beds \| 3 baths \| 3,200 sq.ft.	$799,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 3.19% Airbnb Rental Income: $1873 Traditional Rental Income: $4692 Airbnb ROI: -1.27% Traditional ROI: 3.19%
15 Kirby Hill Road Pawling, NY Kirby 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: -2.34% Traditional cash on cash: -2.1% Airbnb Rental Income: $1873 Traditional Rental Income: $4629 Airbnb ROI: -2.34% Traditional ROI: -2.1%
21 Kings Way Pawling, NY Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderfu...	3 beds \| 3 baths \| 1,960 sq.ft.	$368,888	Airbnb cash on cash: 1.08% Traditional cash on cash: 6.31% Airbnb Rental Income: $2089 Traditional Rental Income: $3362 Airbnb ROI: 1.08% Traditional ROI: 6.31%
4 Mane Way Pawling, NY Elegant and Updated Center Hall Colonial, ideally situated in The Highlands-a beautiful an...	4 beds \| 3 baths \| 3,611 sq.ft.	$775,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 2.31% Airbnb Rental Income: $1873 Traditional Rental Income: $4279 Airbnb ROI: -1.72% Traditional ROI: 2.31%
40 Walnut Street Pawling, NY Spacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful wes...	4 beds \| 2 baths \| 1,776 sq.ft.	$425,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 5.35% Airbnb Rental Income: $1873 Traditional Rental Income: $3619 Airbnb ROI: -0.29% Traditional ROI: 5.35%
168 Old Route 55 Pawling, NY Step into the very year our nation was born and own a piece of American history! Originall...	2 beds \| 2 baths \| 2,196 sq.ft.	$599,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 1.59% Airbnb Rental Income: $1988 Traditional Rental Income: $2850 Airbnb ROI: -0.88% Traditional ROI: 1.59%
20 Saratoga Street Pawling, NY Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Dee...	3 beds \| 4 baths \| 2,503 sq.ft.	$485,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 6.5% Airbnb Rental Income: $2089 Traditional Rental Income: $4335 Airbnb ROI: 0.36% Traditional ROI: 6.5%
58 Pine Drive Pawling, NY Tucked 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: 0.2% Traditional cash on cash: 3.63% Airbnb Rental Income: $2089 Traditional Rental Income: $3251 Airbnb ROI: 0.2% Traditional ROI: 3.63%
16 Juniper Lane Pawling, NY Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and c...	2 beds \| 2 baths \| 1,639 sq.ft.	$375,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.06% Airbnb Rental Income: $1988 Traditional Rental Income: $2918 Airbnb ROI: 0.94% Traditional ROI: 5.06%

Your search for investment property begins and ends here

Single Family Homes for Sale in Pawling, NY

5 Old Field Circle

Pawling, NY

3 beds | 3 baths | 2,104 sq.ft.

$549,222

Airbnb cash on cash: -0.16%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $2089

Traditional Rental Income: $3710

Airbnb ROI: -0.16%

Traditional ROI: 4.05%

13 Cushing Green S

Pawling, NY

2 beds | 3 baths | 1,567 sq.ft.

$425,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1988

Traditional Rental Income: $3014

Airbnb ROI: -0.51%

Traditional ROI: 3.38%

7 Juniper Lane

Pawling, NY

2 beds | 2 baths | 2,596 sq.ft.

$420,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1988

Traditional Rental Income: $3033

Airbnb ROI: -0.53%

Traditional ROI: 3.45%

26 Rodina Drive

Pawling, NY

4 beds | 3 baths | 3,200 sq.ft.

$799,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1873

Traditional Rental Income: $4692

Airbnb ROI: -1.27%

Traditional ROI: 3.19%

15 Kirby Hill Road

Pawling, NY

4 beds | 4 baths | 3,942 sq.ft.

$14,995,000

Airbnb cash on cash: -2.34%

Traditional cash on cash: -2.1%

Airbnb Rental Income: $1873

Traditional Rental Income: $4629

Airbnb ROI: -2.34%

Traditional ROI: -2.1%

21 Kings Way

Pawling, NY

3 beds | 3 baths | 1,960 sq.ft.

$368,888

Airbnb cash on cash: 1.08%

Traditional cash on cash: 6.31%

Airbnb Rental Income: $2089

Traditional Rental Income: $3362

Airbnb ROI: 1.08%

Traditional ROI: 6.31%

4 Mane Way

Pawling, NY

4 beds | 3 baths | 3,611 sq.ft.

$775,000

Airbnb cash on cash: -1.72%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $1873

Traditional Rental Income: $4279

Airbnb ROI: -1.72%

Traditional ROI: 2.31%

40 Walnut Street

Pawling, NY

4 beds | 2 baths | 1,776 sq.ft.

$425,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $1873

Traditional Rental Income: $3619

Airbnb ROI: -0.29%