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.

Condos for Sale in Pawling, NY

Search for Condo for Sale in Pawling, New York. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Condo 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
1 Cushing Green N Pawling, NY This 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% Traditional cash on cash: 4.56% Airbnb Rental Income: $1434 Traditional Rental Income: $3109 Airbnb ROI: -2.12% Traditional ROI: 4.56%
Other Investment Properties for Sale in Pawling
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: 0.41% Traditional cash on cash: 3.11% Airbnb Rental Income: $3010 Traditional Rental Income: $3710 Airbnb ROI: 0.41% Traditional ROI: 3.11%
188 N Quaker Hill Road Pawling , NY Fantastic 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% Traditional cash on cash: 4.21% Airbnb Rental Income: $3010 Traditional Rental Income: $4034 Airbnb ROI: 1.13% Traditional ROI: 4.21%
5 Red Tail Court Pawling , NY Tucked 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% Traditional cash on cash: 3.52% Airbnb Rental Income: $2359 Traditional Rental Income: $4252 Airbnb ROI: -0.9% Traditional ROI: 3.52%
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: 1.34% Traditional cash on cash: 3.16% Airbnb Rental Income: $3010 Traditional Rental Income: $3505 Airbnb ROI: 1.34% Traditional ROI: 3.16%
15 Dykeman St Pawling , NY Fantastic 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% Traditional cash on cash: 5.48% Airbnb Rental Income: $2129 Traditional Rental Income: $1758 Airbnb ROI: 4.63% Traditional ROI: 5.48%
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: -2.31% Traditional cash on cash: -2.1% Airbnb Rental Income: $2359 Traditional Rental Income: $4629 Airbnb ROI: -2.31% Traditional ROI: -2.1%
104 N Garden Dr Pawling , NY 104 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% Traditional cash on cash: -2.53% Airbnb Rental Income: $2434 Traditional Rental Income: $6757 Airbnb ROI: -2.67% Traditional ROI: -2.53%
120 Harmony Rd Pawling , NY 120 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% Traditional cash on cash: 2.71% Airbnb Rental Income: $2434 Traditional Rental Income: $6394 Airbnb ROI: -1.21% Traditional ROI: 2.71%
178 Charles Colman Blvd Pawling , NY 178 Charles Colman Blvd, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| N/A	$1,350,000	Airbnb cash on cash: -1.52% Traditional cash on cash: -1.93% Airbnb Rental Income: $2129 Traditional Rental Income: $1073 Airbnb ROI: -1.52% Traditional ROI: -1.93%
225 Route 22 Pawling , NY 225 Route 22, Pawling, NY 12564 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$9,750,000	Airbnb cash on cash: -2.55% Traditional cash on cash: -2.61% Airbnb Rental Income: $2129 Traditional Rental Income: $1077 Airbnb ROI: -2.55% Traditional ROI: -2.61%
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	$135,000	Airbnb cash on cash: 8.83% Traditional cash on cash: 5.72% Airbnb Rental Income: $2129 Traditional Rental Income: $1183 Airbnb ROI: 8.83% Traditional ROI: 5.72%
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%

Your search for investment property begins and ends here

Condos for Sale in Pawling, NY

1 Cushing Green N

Pawling, NY

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

$335,000

Airbnb cash on cash: -2.12%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1434

Traditional Rental Income: $3109

Airbnb ROI: -2.12%

Traditional ROI: 4.56%

Other Investment Properties for Sale in Pawling

Pawling , NY

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

$549,222

Airbnb cash on cash: 0.41%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $3010

Traditional Rental Income: $3710

Airbnb ROI: 0.41%

Traditional ROI: 3.11%

Pawling , NY

3 beds | 3 baths | 2,636 sq.ft.

$595,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3010

Traditional Rental Income: $4034

Airbnb ROI: 1.13%

Traditional ROI: 4.21%

Pawling , NY

4 beds | 2 baths | 2,924 sq.ft.

$600,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $2359

Traditional Rental Income: $4252

Airbnb ROI: -0.9%

Traditional ROI: 3.52%

Pawling , NY

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

$699,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3010

Traditional Rental Income: $3505

Airbnb ROI: 1.34%

Traditional ROI: 3.16%

Pawling , NY

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

$215,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $2129

Traditional Rental Income: $1758

Airbnb ROI: 4.63%

Traditional ROI: 5.48%

Pawling , NY

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

$14,995,000

Airbnb cash on cash: -2.31%

Traditional cash on cash: -2.1%

Airbnb Rental Income: $2359

Traditional Rental Income: $4629

Airbnb ROI: -2.31%

Traditional ROI: -2.1%

Pawling , NY

9 beds | 9 baths | 55,000 sq.ft.

$39,000,000

Airbnb cash on cash: -2.67%

Traditional cash on cash: -2.53%

Airbnb Rental Income: $2434

Traditional Rental Income: $6757

Airbnb ROI: -2.67%

Traditional ROI: -2.53%

Pawling , NY

5 beds | 4 baths | 3,920 sq.ft.

$1,250,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 2.71%