Real Estate Investment Properties for Sale in Sleepy Hollow, NY

Looking for investment property in Sleepy Hollow, NY with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
46 Andrews Lane Sleepy Hollow, NY Welcome home to Sunset Villas on Andrews lane. A new community of nine luxury townhomes (f...	2 beds \| 4 baths \| 1,512 sq.ft.	$1,199,000	Airbnb cash on cash: -2.4% Traditional cash on cash: 0.3% Airbnb Rental Income: $1809 Traditional Rental Income: $4324 Airbnb ROI: -2.4% Traditional ROI: 0.3%
34 Andrews Lane Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow. Discover Sunset Villas, an ex...	2 beds \| 4 baths \| 1,512 sq.ft.	$899,999	Airbnb cash on cash: -2.86% Traditional cash on cash: 0.71% Airbnb Rental Income: $1809 Traditional Rental Income: $4313 Airbnb ROI: -2.86% Traditional ROI: 0.71%
42 Andrews Lane Sleepy Hollow, NY Welcome home to Sunset Villas on Andrews Lane. A new community of nine luxury townhomes (f...	2 beds \| 4 baths \| 1,512 sq.ft.	$1,099,000	Airbnb cash on cash: -2.53% Traditional cash on cash: 0.4% Airbnb Rental Income: $1809 Traditional Rental Income: $4306 Airbnb ROI: -2.53% Traditional ROI: 0.4%
11 River St #201 Sleepy Hollow, NY 11 River St #201, Tarrytown, NY 10591 \| Condo/Coop	3 beds \| 3 baths \| 1,864 sq.ft.	$1,450,000	Airbnb cash on cash: -1.85% Traditional cash on cash: -0.49% Airbnb Rental Income: $3089 Traditional Rental Income: $4227 Airbnb ROI: -1.85% Traditional ROI: -0.49%
48 Raafenberg Rd Sleepy Hollow, NY 48 Raafenberg Rd, Sleepy Hollow, NY 10591 \| Single Family Residential	5 beds \| 5 baths \| 7,538 sq.ft.	$12,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.08% Airbnb Rental Income: $null Traditional Rental Income: $7172 Airbnb ROI: N/A Traditional ROI: -2.08%
11 River Street #401 Sleepy Hollow, NY This meticulously maintained three-bedroom, three-full-bathroom residence represents one o...	3 beds \| 3 baths \| 1,864 sq.ft.	$1,499,000	Airbnb cash on cash: -2.18% Traditional cash on cash: -0.88% Airbnb Rental Income: $3089 Traditional Rental Income: $4204 Airbnb ROI: -2.18% Traditional ROI: -0.88%
4 Lighthouse Lndg #210 Sleepy Hollow, NY 4 Lighthouse Lndg #210, Sleepy Hollow, NY 10591 \| Condo/Coop	3 beds \| 3 baths \| 2,357 sq.ft.	$3,895,000	Airbnb cash on cash: -2.69% Traditional cash on cash: -2.06% Airbnb Rental Income: $3089 Traditional Rental Income: $4667 Airbnb ROI: -2.69% Traditional ROI: -2.06%
4 Lighthouse Lndg #TH13 Sleepy Hollow, NY 4 Lighthouse Lndg #TH13, Sleepy Hollow, NY 10591 \| Condo/Coop	2 beds \| 3 baths \| 2,101 sq.ft.	$1,690,000	Airbnb cash on cash: -3.16% Traditional cash on cash: -1.14% Airbnb Rental Income: $1809 Traditional Rental Income: $4482 Airbnb ROI: -3.16% Traditional ROI: -1.14%
4 Lighthouse Lndg #TH14 Sleepy Hollow, NY 4 Lighthouse Lndg #TH14, Sleepy Hollow, NY 10591 \| Condo/Coop	3 beds \| 4 baths \| 3,093 sq.ft.	$2,620,000	Airbnb cash on cash: -2.95% Traditional cash on cash: -1.59% Airbnb Rental Income: $3089 Traditional Rental Income: $5673 Airbnb ROI: -2.95% Traditional ROI: -1.59%
32 Andrews Lane Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow. Discover Sunset Villas, an ex...	2 beds \| 4 baths \| 1,512 sq.ft.	$899,999	Airbnb cash on cash: -2.86% Traditional cash on cash: 0.64% Airbnb Rental Income: $1809 Traditional Rental Income: $4250 Airbnb ROI: -2.86% Traditional ROI: 0.64%
4 Lighthouse Lndg #204 Sleepy Hollow, NY 4 Lighthouse Lndg #204, Sleepy Hollow, NY 10591 \| Condo/Coop	3 beds \| 3 baths \| 2,356 sq.ft.	$3,995,000	Airbnb cash on cash: -2.69% Traditional cash on cash: -2.06% Airbnb Rental Income: $3089 Traditional Rental Income: $4710 Airbnb ROI: -2.69% Traditional ROI: -2.06%
34 Hemlock Drive Sleepy Hollow, NY This immaculate four-bedroom residence offers the perfect blend of refined elegance and re...	4 beds \| 3 baths \| 3,120 sq.ft.	$1,795,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.08% Airbnb Rental Income: $4388 Traditional Rental Income: $4963 Airbnb ROI: -0.82% Traditional ROI: 0.08%
203 Palisades Boulevard Sleepy Hollow, NY Beautiful 4-bedroom, 3 full and 2 half bath townhome at Brownstone- Edge on Hudson, perfec...	4 beds \| 5 baths \| 2,936 sq.ft.	$1,850,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.66% Airbnb Rental Income: $4388 Traditional Rental Income: $7251 Airbnb ROI: -1.54% Traditional ROI: 0.66%
201 Horseman Boulevard #101 Sleepy Hollow, NY Welcome to Horseman Boulevard. Just 25 miles north of NYC, Sleepy Hollow offers luxury liv...	2 beds \| 3 baths \| 1,228 sq.ft.	$1,299,000	Airbnb cash on cash: -2.63% Traditional cash on cash: -0.42% Airbnb Rental Income: $1809 Traditional Rental Income: $3985 Airbnb ROI: -2.63% Traditional ROI: -0.42%
46 Andrews Lane #46 Sleepy Hollow, NY Welcome home to Sunset Villas on Andrews lane. A new community of nine luxury townhomes (f...	2 beds \| 4 baths \| N/A	$1,199,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 1.5% Airbnb Rental Income: $1809 Traditional Rental Income: $5179 Airbnb ROI: -1.96% Traditional ROI: 1.5%
42 Andrews Lane #42 Sleepy Hollow, NY Welcome home to Sunset Villas on Andrews lane. A new community of nine luxury townhomes (f...	2 beds \| 4 baths \| N/A	$1,099,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 2.27% Airbnb Rental Income: $1809 Traditional Rental Income: $5179 Airbnb ROI: -1.51% Traditional ROI: 2.27%
30 Kendall Ave Sleepy Hollow, NY 30 Kendall Ave, Sleepy Hollow, NY 10591 \| Single Family Residential	3 beds \| 2 baths \| 2,200 sq.ft.	$629,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 3% Airbnb Rental Income: $3089 Traditional Rental Income: $3446 Airbnb ROI: 1.19% Traditional ROI: 3%
206 Legend Dr Sleepy Hollow, NY 206 Legend Dr, Sleepy Hollow, NY 10591 \| Single Family Residential	4 beds \| 3 baths \| 2,676 sq.ft.	$1,695,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.1% Airbnb Rental Income: $4388 Traditional Rental Income: $4813 Airbnb ROI: -0.96% Traditional ROI: -0.1%
348 Horseman Blvd Sleepy Hollow, NY 348 Horseman Blvd, Sleepy Hollow, NY 10591 \| Condo/Coop	3 beds \| 2 baths \| 2,913 sq.ft.	$1,900,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -1.03% Airbnb Rental Income: $3089 Traditional Rental Income: $3666 Airbnb ROI: -1.76% Traditional ROI: -1.03%
4 Lighthouse Lndg #424 Sleepy Hollow, NY 4 Lighthouse Lndg #424, Sleepy Hollow, NY 10591 \| Condo/Coop	3 beds \| 2 baths \| 1,886 sq.ft.	$3,115,000	Airbnb cash on cash: -2.52% Traditional cash on cash: -2.03% Airbnb Rental Income: $3089 Traditional Rental Income: $3809 Airbnb ROI: -2.52% Traditional ROI: -2.03%
49 Howard Street Sleepy Hollow, NY This well-appointed two-family residence presents a rare opportunity in the highly sought-...	7 beds \| 2 baths \| N/A	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $3721 Airbnb ROI: N/A Traditional ROI: 2.47%
17 Anderson Avenue Sleepy Hollow, NY Nestled on a lovely tree-lined street in Sleepy Hollow, this 3-bedroom, 1-bath 1930's Colo...	3 beds \| 1 baths \| 1,190 sq.ft.	$565,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.63% Airbnb Rental Income: $3089 Traditional Rental Income: $3167 Airbnb ROI: 1.15% Traditional ROI: 2.63%
30 Andrews Lane Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover S...	2 beds \| 4 baths \| 1,512 sq.ft.	$999,999	Airbnb cash on cash: -2.68% Traditional cash on cash: 0.52% Airbnb Rental Income: $1809 Traditional Rental Income: $4296 Airbnb ROI: -2.68% Traditional ROI: 0.52%
36 Andrews Lane Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover S...	2 beds \| 4 baths \| 1,512 sq.ft.	$999,999	Airbnb cash on cash: -2.68% Traditional cash on cash: 0.52% Airbnb Rental Income: $1809 Traditional Rental Income: $4296 Airbnb ROI: -2.68% Traditional ROI: 0.52%
34 Cedar St Sleepy Hollow, NY 34 Cedar St, Sleepy Hollow, NY 10591 \| Multi Family	5 beds \| 2 baths \| 1,991 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.18% Airbnb Rental Income: $null Traditional Rental Income: $3687 Airbnb ROI: N/A Traditional ROI: 2.18%
50 Hudson St Sleepy Hollow, NY 50 Hudson St, Sleepy Hollow, NY 10591 \| Single Family Residential	4 beds \| 1 baths \| 1,398 sq.ft.	$599,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.01% Airbnb Rental Income: $4388 Traditional Rental Income: $3289 Airbnb ROI: 3.33% Traditional ROI: 3.01%

Real Estate investment in Sleepy-hollow, NY

There are 26 properties for sale in the city of Sleepy Hollow . The median list price in Sleepy Hollow is $1,524,213 and the average price per square foot is $677. In June 2026, the average monthly cash on cash return in Sleepy Hollow is N/A%. The average monthly rental income in Sleepy Hollow is $4,296.

Sleepy-hollow, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 26 investment properties available for sale in Sleepy-hollow.

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

The ROI for Long-Term is higher than the Short-Term in Sleepy-hollow with average rental income of $4,296.

Your search for investment property begins and ends here

Investment Property for Sale in Sleepy Hollow, NY

46 Andrews Lane

Sleepy Hollow, NY

2 beds | 4 baths | 1,512 sq.ft.

$1,199,000

Airbnb cash on cash: -2.4%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1809

Traditional Rental Income: $4324

Airbnb ROI: -2.4%

Traditional ROI: 0.3%

34 Andrews Lane

Sleepy Hollow, NY

2 beds | 4 baths | 1,512 sq.ft.

$899,999

Airbnb cash on cash: -2.86%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $1809

Traditional Rental Income: $4313

Airbnb ROI: -2.86%

Traditional ROI: 0.71%

42 Andrews Lane

Sleepy Hollow, NY

2 beds | 4 baths | 1,512 sq.ft.

$1,099,000

Airbnb cash on cash: -2.53%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $1809

Traditional Rental Income: $4306

Airbnb ROI: -2.53%

Traditional ROI: 0.4%

11 River St #201

Sleepy Hollow, NY

3 beds | 3 baths | 1,864 sq.ft.

$1,450,000

Airbnb cash on cash: -1.85%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $3089

Traditional Rental Income: $4227

Airbnb ROI: -1.85%

Traditional ROI: -0.49%

48 Raafenberg Rd

Sleepy Hollow, NY

5 beds | 5 baths | 7,538 sq.ft.

$12,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.08%

Airbnb Rental Income: $null

Traditional Rental Income: $7172

Airbnb ROI: N/A

Traditional ROI: -2.08%

11 River Street #401

Sleepy Hollow, NY

3 beds | 3 baths | 1,864 sq.ft.

$1,499,000

Airbnb cash on cash: -2.18%

Traditional cash on cash: -0.88%

Airbnb Rental Income: $3089

Traditional Rental Income: $4204

Airbnb ROI: -2.18%

Traditional ROI: -0.88%

4 Lighthouse Lndg #210

Sleepy Hollow, NY

3 beds | 3 baths | 2,357 sq.ft.

$3,895,000

Airbnb cash on cash: -2.69%

Traditional cash on cash: -2.06%

Airbnb Rental Income: $3089

Traditional Rental Income: $4667

Airbnb ROI: -2.69%

Traditional ROI: -2.06%

4 Lighthouse Lndg #TH13

Sleepy Hollow, NY

2 beds | 3 baths | 2,101 sq.ft.

$1,690,000

Airbnb cash on cash: -3.16%

Traditional cash on cash: -1.14%

Airbnb Rental Income: $1809

Traditional Rental Income: $4482

Airbnb ROI: -3.16%