Real Estate Investment Properties for Sale in Chautauqua, NY

Looking for investment property in Chautauqua, NY with high ROI ?

Explore a variety of short-term homes & houses in Chautauqua, NY. Invest wisely with VRBO & Chautauqua, 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 Chautauqua, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Elm Lane Chautauqua, NY Indulge in breathtaking lake views from this exquisite mid-century modern home at the corn...	5 beds \| 4 baths \| 2,722 sq.ft.	$3,500,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.74% Airbnb Rental Income: $2597 Traditional Rental Income: $3520 Airbnb ROI: -1.22% Traditional ROI: -0.74%
83 Pratt Avenue Chautauqua, NY Mid-Century Modern Gem in the Heart of Chautauqua Institution - 83 Pratt Avenue, Chautauqu...	5 beds \| 3 baths \| 2,384 sq.ft.	$1,275,000	Airbnb cash on cash: -1.44% Traditional cash on cash: -0.32% Airbnb Rental Income: $2597 Traditional Rental Income: $3311 Airbnb ROI: -1.44% Traditional ROI: -0.32%
6651 Webber Chautauqua, NY Stunning country home with log cabin feel! Escape to your own slice of country paradise! T...	4 beds \| 2 baths \| 2,240 sq.ft.	$249,500	Airbnb cash on cash: 1.69% Traditional cash on cash: 9.05% Airbnb Rental Income: $1322 Traditional Rental Income: $2647 Airbnb ROI: 1.69% Traditional ROI: 9.05%
Investment Properties for Sale in Other Cities of New-york
284 Bayview Avenue Inwood , NY Explore this inviting 4 bedrooms, 3 bathroom home with a main floor bedroom and full bath....	4 beds \| 3 baths \| 1,350 sq.ft.	$599,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 3.59% Airbnb Rental Income: $831 Traditional Rental Income: $3124 Airbnb ROI: -1.09% Traditional ROI: 3.59%
15 Dewey Pl New York , NY 15 Dewey Pl, New York, NY 11233 \| Single Family Residential	3 beds \| 5 baths \| 2,031 sq.ft.	$1,599,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.48% Airbnb Rental Income: $3767 Traditional Rental Income: $4835 Airbnb ROI: -0.79% Traditional ROI: 0.48%
188 Weston Road Rochester , NY OPEN HOUSES: FRIDAY 10/17 5PM TO 6:30PM & SUNDAY 10/19 12PM TO 1:30PM Step into this cozy ...	2 beds \| 2 baths \| 1,238 sq.ft.	$149,900	Airbnb cash on cash: 4.18% Traditional cash on cash: 9.08% Airbnb Rental Income: $1619 Traditional Rental Income: $1862 Airbnb ROI: 4.18% Traditional ROI: 9.08%
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: 5.69% Traditional cash on cash: 4.14% Airbnb Rental Income: $5736 Traditional Rental Income: $3648 Airbnb ROI: 5.69% Traditional ROI: 4.14%
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 Avenue 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%
75 Longview Road New York , NY Exquisite Contemporary Estate in Prestigious Grymes Hill Discover an architectural mast...	4 beds \| 4 baths \| 3,000 sq.ft.	$1,748,999	Airbnb cash on cash: 2.3% Traditional cash on cash: 1.03% Airbnb Rental Income: $7742 Traditional Rental Income: $4195 Airbnb ROI: 2.3% Traditional ROI: 1.03%
76 Douglas Road New York , NY Welcome to Douglas Road, nestled in the prestigious Emerson Hill neighborhood of Staten Is...	4 beds \| 3 baths \| 5,320 sq.ft.	$2,249,999	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.26% Airbnb Rental Income: $7742 Traditional Rental Income: $4207 Airbnb ROI: 1.24% Traditional ROI: 0.26%
64-05 Yellowstone Boulevard #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.	$1,230,000	Airbnb cash on cash: -3.41% Traditional cash on cash: -2.23% Airbnb Rental Income: $2515 Traditional Rental Income: $3258 Airbnb ROI: -3.41% Traditional ROI: -2.23%
200 Coverly Avenue New York , NY Experience the ultimate in transformative living, surrounded by nature and awakened to bre...	5 beds \| N/A baths \| 3,801 sq.ft.	$1,879,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $5073 Airbnb ROI: N/A Traditional ROI: 1.12%
16 Serenity Road Greenwood Lake , NY This is the Lake Life you've been waiting for. Newly painted 2 bedroom/1 bath log cabin w...	2 beds \| 1 baths \| 984 sq.ft.	$385,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.2% Airbnb Rental Income: $2063 Traditional Rental Income: $2409 Airbnb ROI: 0.76% Traditional ROI: 3.2%
17 Waterstone Road Greenwood Lake , NY 🌊 A Must-See Greenwood Lake Gem - Pictures Can't Capture These Views! 🌊Thi...	3 beds \| 3 baths \| 1,564 sq.ft.	$649,900	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.15% Airbnb Rental Income: $3082 Traditional Rental Income: $3400 Airbnb ROI: 1.46% Traditional ROI: 3.15%
183-36 Dunlop Avenue New York , NY Discover this meticulously maintained brick home in the vibrant neighborhood of St. Albans...	5 beds \| 2 baths \| 1,694 sq.ft.	$698,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $3768 Airbnb ROI: N/A Traditional ROI: 3.92%
16 Mapleton Avenue New York , NY Lot size 20x100, building size 12x55, Zoning R3-1. It is a great opportunity to use or inv...	2 beds \| 1 baths \| 528 sq.ft.	$350,000	Airbnb cash on cash: 8.83% Traditional cash on cash: 4.96% Airbnb Rental Income: $4328 Traditional Rental Income: $2147 Airbnb ROI: 8.83% Traditional ROI: 4.96%
144 Winchester Avenue New York , NY Location, location, location! This beautifully renovated single-family detached home is ne...	2 beds \| 2 baths \| 1,000 sq.ft.	$769,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 1.53% Airbnb Rental Income: $4328 Traditional Rental Income: $2430 Airbnb ROI: 2.91% Traditional ROI: 1.53%

Real Estate investment in Chautauqua, NY

There are 3 properties for sale in the city of Chautauqua . The median list price in Chautauqua is $1,275,000 and the average price per square foot is $521. In October 2025, the average monthly cash on cash return in Chautauqua is N/A%. The average monthly rental income in Chautauqua is $3,311.

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

There are 3 investment properties available for sale in Chautauqua.

In 2025, the best neighborhood to buy investment property is Chautauqua.

The ROI for Long-Term is higher than the Short-Term in Chautauqua with average rental income of $3,311.

Your search for investment property begins and ends here

Investment Property for Sale in Chautauqua, NY

2 Elm Lane

Chautauqua, NY

5 beds | 4 baths | 2,722 sq.ft.

$3,500,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: -0.74%

Airbnb Rental Income: $2597

Traditional Rental Income: $3520

Airbnb ROI: -1.22%

Traditional ROI: -0.74%

83 Pratt Avenue

Chautauqua, NY

5 beds | 3 baths | 2,384 sq.ft.

$1,275,000

Airbnb cash on cash: -1.44%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $2597

Traditional Rental Income: $3311

Airbnb ROI: -1.44%

Traditional ROI: -0.32%

6651 Webber

Chautauqua, NY

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

$249,500

Airbnb cash on cash: 1.69%

Traditional cash on cash: 9.05%

Airbnb Rental Income: $1322

Traditional Rental Income: $2647

Airbnb ROI: 1.69%

Traditional ROI: 9.05%

Investment Properties for Sale in Other Cities of New-york

Inwood , NY

4 beds | 3 baths | 1,350 sq.ft.

$599,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $831

Traditional Rental Income: $3124

Airbnb ROI: -1.09%

Traditional ROI: 3.59%

New York , NY

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

$1,599,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $3767

Traditional Rental Income: $4835

Airbnb ROI: -0.79%

Traditional ROI: 0.48%

Rochester , NY

2 beds | 2 baths | 1,238 sq.ft.

$149,900

Airbnb cash on cash: 4.18%

Traditional cash on cash: 9.08%

Airbnb Rental Income: $1619

Traditional Rental Income: $1862

Airbnb ROI: 4.18%

Traditional ROI: 9.08%

New York , NY

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

$649,999

Airbnb cash on cash: 5.69%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $5736

Traditional Rental Income: $3648

Airbnb ROI: 5.69%

Traditional ROI: 4.14%

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