Real Estate Investment Properties for Sale in Smallwood, NY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
91 W Oak Street Smallwood, NY Serene Smallwood private oasis on .63 acres is year round and now on the market. This peac...	3 beds \| 1 baths \| 676 sq.ft.	$265,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.03% Airbnb Rental Income: $1546 Traditional Rental Income: $1616 Airbnb ROI: 1.96% Traditional ROI: 4.03%
7 Hemlock Avenue Smallwood, NY Year round 2 bedroom, 1 full bath home in the hip hamlet of Smallwood is now on the market...	2 beds \| 1 baths \| 996 sq.ft.	$224,500	Airbnb cash on cash: 3.98% Traditional cash on cash: 5.18% Airbnb Rental Income: $1930 Traditional Rental Income: $1675 Airbnb ROI: 3.98% Traditional ROI: 5.18%
51 E Oak Street Smallwood, NY Newly restored Smallwood cottage with reclaimed metal and wood has a very cool rustic char...	2 beds \| 1 baths \| 806 sq.ft.	$189,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 6.53% Airbnb Rental Income: $1930 Traditional Rental Income: $1672 Airbnb ROI: 5.12% Traditional ROI: 6.53%
45 W Adirondack Trail Smallwood, NY This charming move in ready well-maintained year around 3 BR 2 full bath home is on one of...	3 beds \| 2 baths \| 1,554 sq.ft.	$424,500	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.27% Airbnb Rental Income: $1546 Traditional Rental Income: $2137 Airbnb ROI: 0.66% Traditional ROI: 3.27%
39 E James Avenue Smallwood, NY Your Smallwood search is over! Beautifully situated at the end of a dead end, this fun cab...	3 beds \| 2 baths \| 829 sq.ft.	$289,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 5.22% Airbnb Rental Income: $1546 Traditional Rental Income: $2064 Airbnb ROI: 1.69% Traditional ROI: 5.22%
21 E Sullivan Place Smallwood, NY Charming Catskills Retreat in Smallwood Lake Community. Welcome to your peaceful getaway i...	2 beds \| 1 baths \| 936 sq.ft.	$285,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.15% Airbnb Rental Income: $1930 Traditional Rental Income: $1741 Airbnb ROI: 2.96% Traditional ROI: 4.15%
36 W Read Avenue Smallwood, NY This charming cabin-style ranch home is move-in ready and waiting for its next owner! ALL ...	3 beds \| 1 baths \| 1,140 sq.ft.	$229,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 5.28% Airbnb Rental Income: $1546 Traditional Rental Income: $1739 Airbnb ROI: 2.33% Traditional ROI: 5.28%
74 E Thompson Place Smallwood, NY Sweet Smallwood 3 season cottage is now on the market. Considerable eat in kitchen has ple...	2 beds \| 1 baths \| 780 sq.ft.	$124,500	Airbnb cash on cash: 8.42% Traditional cash on cash: 9.61% Airbnb Rental Income: $1930 Traditional Rental Income: $1562 Airbnb ROI: 8.42% Traditional ROI: 9.61%
30 N Mohican Trail Smallwood, NY Step into the charm of the 1930s with this beautiful home in Bethel/Smallwood. Featuring s...	3 beds \| 1 baths \| 1,310 sq.ft.	$260,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 4.43% Airbnb Rental Income: $1546 Traditional Rental Income: $1673 Airbnb ROI: 2.09% Traditional ROI: 4.43%
23 W James Avenue Smallwood, NY Ideal for weekends get away or to spend summer vacations in the Catskill Mountains, this ...	2 beds \| 1 baths \| 735 sq.ft.	$129,500	Airbnb cash on cash: 8.24% Traditional cash on cash: 9.15% Airbnb Rental Income: $1930 Traditional Rental Income: $1533 Airbnb ROI: 8.24% Traditional ROI: 9.15%
99 W Starlight Drive Smallwood, NY Motivated Seller!!! Bring an offer!!! Once in a lifetime opportunity to own one of the bes...	3 beds \| 2 baths \| 1,592 sq.ft.	$625,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.67% Airbnb Rental Income: $1546 Traditional Rental Income: $2411 Airbnb ROI: -0.58% Traditional ROI: 1.67%
23 Woodland Way Smallwood, NY Step into TRANQUILITY at This Charming RETREAT Near Bethel Woods & Outdoor Adventures! Esc...	3 beds \| 2 baths \| 1,395 sq.ft.	$293,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 5.91% Airbnb Rental Income: $1546 Traditional Rental Income: $2229 Airbnb ROI: 1.81% Traditional ROI: 5.91%
5 Dietrich Place Smallwood, NY This vintage Smallwood Lake cabin has been lovingly owned by the same family for over 60 y...	3 beds \| 2 baths \| 1,900 sq.ft.	$549,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.36% Airbnb Rental Income: $1546 Traditional Rental Income: $2788 Airbnb ROI: 0.07% Traditional ROI: 3.36%
11 W Mongaup Trail Smallwood, NY Welcome to Shangri-La, a peaceful 3-bedroom, 3-bath retreat tucked away on a quiet cul-de-...	3 beds \| 3 baths \| 1,517 sq.ft.	$394,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 5.22% Airbnb Rental Income: $1546 Traditional Rental Income: $2807 Airbnb ROI: 0.6% Traditional ROI: 5.22%
45 W Kenoza Place Smallwood, NY Charming and spacious 1 bedroom, 1 full bath cottage in the popular lake community of Smal...	1 beds \| 1 baths \| 760 sq.ft.	$224,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 4.44% Airbnb Rental Income: $1165 Traditional Rental Income: $1481 Airbnb ROI: 1.15% Traditional ROI: 4.44%
65 Berkshire Trail Smallwood, NY Updated 4BR/3BA Raised Ranch on nearly 1/2 acre Beautifully updated 1970 raised ranch wit...	4 beds \| 3 baths \| 2,112 sq.ft.	$370,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 7.21% Airbnb Rental Income: $2260 Traditional Rental Income: $3339 Airbnb ROI: 2.47% Traditional ROI: 7.21%
71 Keller Avenue Smallwood, NY Welcome to this well-loved and beautifully maintained two-bedroom cabin that blends old-wo...	2 beds \| 2 baths \| 810 sq.ft.	$264,900	Airbnb cash on cash: 3.21% Traditional cash on cash: 4.74% Airbnb Rental Income: $1930 Traditional Rental Income: $1803 Airbnb ROI: 3.21% Traditional ROI: 4.74%
82 Gina Lane #TR 127 Smallwood, NY Tranquil Catskills Retreat â Just Under 2 Hours from NYC! Located on a quiet road, priv...	3 beds \| 2 baths \| 1,352 sq.ft.	$385,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 2.98% Airbnb Rental Income: $1546 Traditional Rental Income: $2097 Airbnb ROI: 0.22% Traditional ROI: 2.98%
65 W James Avenue Smallwood, NY On the lakeside of Smallwood, this 3 season cottage has 2 bedrooms and 1 full bath. Low ta...	2 beds \| 1 baths \| 640 sq.ft.	$119,900	Airbnb cash on cash: 9.29% Traditional cash on cash: 10.82% Airbnb Rental Income: $1930 Traditional Rental Income: $1596 Airbnb ROI: 9.29% Traditional ROI: 10.82%

Real Estate investment in Smallwood, NY

There are 19 properties for sale in the city of Smallwood . The median list price in Smallwood is $264,950 and the average price per square foot is $231. In September 2025, the average monthly cash on cash return in Smallwood is 5.00%. The average monthly rental income in Smallwood is $1,740.

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

There are 19 investment properties available for sale in Smallwood.

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

The ROI for Long-Term is higher than the Short-Term in Smallwood with average rental income of $1,740.

Your search for investment property begins and ends here

Investment Property for Sale in Smallwood, NY

91 W Oak Street

Smallwood, NY

3 beds | 1 baths | 676 sq.ft.

$265,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $1546

Traditional Rental Income: $1616

Airbnb ROI: 1.96%

Traditional ROI: 4.03%

7 Hemlock Avenue

Smallwood, NY

2 beds | 1 baths | 996 sq.ft.

$224,500

Airbnb cash on cash: 3.98%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $1930

Traditional Rental Income: $1675

Airbnb ROI: 3.98%

Traditional ROI: 5.18%

51 E Oak Street

Smallwood, NY

2 beds | 1 baths | 806 sq.ft.

$189,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $1930

Traditional Rental Income: $1672

Airbnb ROI: 5.12%

Traditional ROI: 6.53%

45 W Adirondack Trail

Smallwood, NY

3 beds | 2 baths | 1,554 sq.ft.

$424,500

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1546

Traditional Rental Income: $2137

Airbnb ROI: 0.66%

Traditional ROI: 3.27%

39 E James Avenue

Smallwood, NY

3 beds | 2 baths | 829 sq.ft.

$289,900

Airbnb cash on cash: 1.69%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $1546

Traditional Rental Income: $2064

Airbnb ROI: 1.69%

Traditional ROI: 5.22%

21 E Sullivan Place

Smallwood, NY

2 beds | 1 baths | 936 sq.ft.

$285,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1930

Traditional Rental Income: $1741

Airbnb ROI: 2.96%

Traditional ROI: 4.15%

36 W Read Avenue

Smallwood, NY

3 beds | 1 baths | 1,140 sq.ft.

$229,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $1546

Traditional Rental Income: $1739

Airbnb ROI: 2.33%

Traditional ROI: 5.28%

74 E Thompson Place

Smallwood, NY

2 beds | 1 baths | 780 sq.ft.

$124,500

Airbnb cash on cash: 8.42%

Traditional cash on cash: 9.61%

Airbnb Rental Income: $1930

Traditional Rental Income: $1562

Airbnb ROI: 8.42%