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: -1.45% Traditional cash on cash: 0.3% Airbnb Rental Income: $3084 Traditional Rental Income: $4324 Airbnb ROI: -1.45% Traditional ROI: 0.3%
34 Andrews Ln Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow. Discover Sunset Villas, an ex...	2 beds \| 3 baths \| 1,512 sq.ft.	$899,999	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.71% Airbnb Rental Income: $3084 Traditional Rental Income: $4313 Airbnb ROI: -1.59% Traditional ROI: 0.71%
42 Andrews Ln Sleepy Hollow, NY Welcome home to Sunset Villas on Andrews Lane. A new community of nine luxury townhomes (f...	2 beds \| 3 baths \| 1,512 sq.ft.	$999,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.54% Airbnb Rental Income: $3084 Traditional Rental Income: $4306 Airbnb ROI: -1.54% Traditional ROI: 0.54%
167 Millard Avenue Sleepy Hollow, NY As does Frank Lloyd Wright's "Fallingwater," this hilltop enclave provides privacy, luxury...	4 beds \| 5 baths \| 5,700 sq.ft.	$3,300,000	Airbnb cash on cash: -2.28% Traditional cash on cash: -0.63% Airbnb Rental Income: $2397 Traditional Rental Income: $6867 Airbnb ROI: -2.28% Traditional ROI: -0.63%
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: -3.93% Traditional cash on cash: -0.88% Airbnb Rental Income: $176 Traditional Rental Income: $4204 Airbnb ROI: -3.93% 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.	$3,795,000	Airbnb cash on cash: -3.38% Traditional cash on cash: -2.04% Airbnb Rental Income: $176 Traditional Rental Income: $4667 Airbnb ROI: -3.38% Traditional ROI: -2.04%
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.	$1,550,000	Airbnb cash on cash: -2.46% Traditional cash on cash: -1% Airbnb Rental Income: $3084 Traditional Rental Income: $4482 Airbnb ROI: -2.46% Traditional ROI: -1%
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.	$2,200,000	Airbnb cash on cash: -4.18% Traditional cash on cash: -1.38% Airbnb Rental Income: $176 Traditional Rental Income: $5673 Airbnb ROI: -4.18% Traditional ROI: -1.38%
32 Andrews Ln Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow. Discover Sunset Villas, an ex...	2 beds \| 3 baths \| 1,512 sq.ft.	$899,999	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.64% Airbnb Rental Income: $3084 Traditional Rental Income: $4250 Airbnb ROI: -1.59% 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.	$3,745,000	Airbnb cash on cash: -3.38% Traditional cash on cash: -2.02% Airbnb Rental Income: $176 Traditional Rental Income: $4710 Airbnb ROI: -3.38% Traditional ROI: -2.02%
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: -1.81% Traditional cash on cash: 0.08% Airbnb Rental Income: $2397 Traditional Rental Income: $4963 Airbnb ROI: -1.81% Traditional ROI: 0.08%
203 Palisades Blvd Sleepy Hollow, NY Please send pof or pre app to phyllis before showing...Beautiful 4-bedroom, 3 full and 2 h...	4 beds \| 3 baths \| 2,936 sq.ft.	$1,850,000	Airbnb cash on cash: -2.54% Traditional cash on cash: 0.63% Airbnb Rental Income: $2397 Traditional Rental Income: $7251 Airbnb ROI: -2.54% Traditional ROI: 0.63%
201 Horseman Blvd #101 Sleepy Hollow, NY Welcome to Horseman Boulevard. Just 25 miles north of NYC, Sleepy Hollow offers luxury liv...	2 beds \| 2 baths \| 1,228 sq.ft.	$1,250,000	Airbnb cash on cash: -1.78% Traditional cash on cash: -0.4% Airbnb Rental Income: $3084 Traditional Rental Income: $3985 Airbnb ROI: -1.78% Traditional ROI: -0.4%
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 \| 1,512 sq.ft.	$1,199,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.5% Airbnb Rental Income: $3084 Traditional Rental Income: $5179 Airbnb ROI: -1.01% 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 \| 1,512 sq.ft.	$1,099,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.27% Airbnb Rental Income: $3084 Traditional Rental Income: $5179 Airbnb ROI: -0.47% 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.	$599,900	Airbnb cash on cash: -2.95% Traditional cash on cash: 3.28% Airbnb Rental Income: $176 Traditional Rental Income: $3446 Airbnb ROI: -2.95% Traditional ROI: 3.28%
206 Legend Dr Sleepy Hollow, NY 206 Legend Dr, Sleepy Hollow, NY 10591 \| Single Family Residential	4 beds \| 3 baths \| 2,676 sq.ft.	$1,595,000	Airbnb cash on cash: -1.97% Traditional cash on cash: 0.06% Airbnb Rental Income: $2397 Traditional Rental Income: $4813 Airbnb ROI: -1.97% Traditional ROI: 0.06%
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: -3.36% Traditional cash on cash: -2.03% Airbnb Rental Income: $176 Traditional Rental Income: $3809 Airbnb ROI: -3.36% 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: -3.45% Traditional cash on cash: 2.63% Airbnb Rental Income: $176 Traditional Rental Income: $3167 Airbnb ROI: -3.45% Traditional ROI: 2.63%
30 Andrews Ln Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover S...	2 beds \| 3 baths \| 1,512 sq.ft.	$999,999	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.52% Airbnb Rental Income: $3084 Traditional Rental Income: $4296 Airbnb ROI: -1.53% Traditional ROI: 0.52%
36 Andrews Ln Sleepy Hollow, NY Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover S...	2 beds \| 3 baths \| 1,512 sq.ft.	$999,999	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.52% Airbnb Rental Income: $3084 Traditional Rental Income: $4296 Airbnb ROI: -1.53% Traditional ROI: 0.52%
144 Beekman Ave Sleepy Hollow, NY Rare Sleepy Hollow 2-Family Double-Duplex with River & Bridge Views.....!! This opportunit...	5 beds \| 4 baths \| 3,372 sq.ft.	$1,500,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.79% Airbnb Rental Income: $3084 Traditional Rental Income: $6012 Airbnb ROI: -0.82% Traditional ROI: 1.79%
34 Cedar St Sleepy Hollow, NY 34 Cedar St, Sleepy Hollow, NY 10591 \| Multi Family	5 beds \| 2 baths \| 1,991 sq.ft.	$699,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 2.81% Airbnb Rental Income: $3084 Traditional Rental Income: $3687 Airbnb ROI: 0.8% Traditional ROI: 2.81%
324 Horseman Blvd Sleepy Hollow, NY The Layout and First Impressions Living in this modern, four-level end-unit brownstone is ...	4 beds \| 4 baths \| 2,646 sq.ft.	$2,500,000	Airbnb cash on cash: -2.53% Traditional cash on cash: -0.61% Airbnb Rental Income: $2397 Traditional Rental Income: $6265 Airbnb ROI: -2.53% Traditional ROI: -0.61%
12 Webb Road Sleepy Hollow, NY Situated in "Sleepy Hollow Manor" (one of Westchester's most sought after neighborhoods) i...	5 beds \| 4 baths \| 2,762 sq.ft.	$1,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.06% Airbnb Rental Income: $null Traditional Rental Income: $5270 Airbnb ROI: N/A Traditional ROI: 1.06%
102 Legend Dr #301 Sleepy Hollow, NY 102 Legend Dr #301, Sleepy Hollow, NY 10591 \| Condo/Coop	1 beds \| 1 baths \| 1,178 sq.ft.	$1,195,000	Airbnb cash on cash: -2.55% Traditional cash on cash: -0.97% Airbnb Rental Income: $1227 Traditional Rental Income: $2593 Airbnb ROI: -2.55% Traditional ROI: -0.97%
100 Legend Dr #206 Sleepy Hollow, NY 100 Legend Dr #206, Sleepy Hollow, NY 10591 \| Condo/Coop	2 beds \| 2 baths \| 1,190 sq.ft.	$1,249,500	Airbnb cash on cash: -1.53% Traditional cash on cash: -0.66% Airbnb Rental Income: $3084 Traditional Rental Income: $3394 Airbnb ROI: -1.53% Traditional ROI: -0.66%
207 Palisades Blvd Sleepy Hollow, NY 207 Palisades Blvd, Sleepy Hollow, NY 10591 \| Condo/Coop	4 beds \| 3 baths \| 3,051 sq.ft.	$1,950,000	Airbnb cash on cash: -2.1% Traditional cash on cash: -0.25% Airbnb Rental Income: $2397 Traditional Rental Income: $5165 Airbnb ROI: -2.1% Traditional ROI: -0.25%
4 Lighthouse Lndg #305 Sleepy Hollow, NY 4 Lighthouse Lndg #305, Sleepy Hollow, NY 10591 \| Condo/Coop	2 beds \| 2 baths \| 1,688 sq.ft.	$1,840,000	Airbnb cash on cash: -2.28% Traditional cash on cash: -1.56% Airbnb Rental Income: $3084 Traditional Rental Income: $3611 Airbnb ROI: -2.28% Traditional ROI: -1.56%
340 Horseman Blvd Sleepy Hollow, NY 340 Horseman Blvd, Sleepy Hollow, NY 10591 \| Condo/Coop	4 beds \| 3 baths \| 3,060 sq.ft.	$2,075,000	Airbnb cash on cash: -2.14% Traditional cash on cash: -0.54% Airbnb Rental Income: $2397 Traditional Rental Income: $4893 Airbnb ROI: -2.14% Traditional ROI: -0.54%
10 Clinton St Sleepy Hollow, NY Exceptional investment opportunity in the heart of Sleepy Hollow! This legal two-family pr...	4 beds \| 2 baths \| 1,520 sq.ft.	$479,500	Airbnb cash on cash: 2.35% Traditional cash on cash: 6.54% Airbnb Rental Income: $2397 Traditional Rental Income: $3688 Airbnb ROI: 2.35% Traditional ROI: 6.54%
62 Hemlock Dr Sleepy Hollow, NY Discover timeless Colonial charm at 62 Hemlock Drive, ideally situated in the sought-after...	4 beds \| 2 baths \| 2,032 sq.ft.	$1,250,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 0.26% Airbnb Rental Income: $2397 Traditional Rental Income: $3920 Airbnb ROI: -1.56% Traditional ROI: 0.26%
9 Irving Pl Sleepy Hollow, NY 9 Irving Pl, Sleepy Hollow, NY 10591 \| Multi Family	7 beds \| 4 baths \| 4,052 sq.ft.	$970,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.79% Airbnb Rental Income: $2397 Traditional Rental Income: $5962 Airbnb ROI: -0.81% Traditional ROI: 3.79%
4 Lighthouse Lndg #302 Sleepy Hollow, NY 4 Lighthouse Lndg #302, Sleepy Hollow, NY 10591 \| Condo/Coop	2 beds \| 2 baths \| 1,593 sq.ft.	$1,780,000	Airbnb cash on cash: -2.22% Traditional cash on cash: -1.48% Airbnb Rental Income: $3084 Traditional Rental Income: $3595 Airbnb ROI: -2.22% Traditional ROI: -1.48%
540 Bedford Rd Sleepy Hollow, NY 540 Bedford Rd, Sleepy Hollow, NY 10591 \| Single Family Residential	3 beds \| 1 baths \| 1,748 sq.ft.	$949,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 0.61% Airbnb Rental Income: $176 Traditional Rental Income: $3028 Airbnb ROI: -2.86% Traditional ROI: 0.61%
5 Lakeview Ave Sleepy Hollow, NY 5 Lakeview Ave, Sleepy Hollow, NY 10591 \| Single Family Residential	3 beds \| 2 baths \| 1,884 sq.ft.	$935,000	Airbnb cash on cash: -2.87% Traditional cash on cash: 1.24% Airbnb Rental Income: $176 Traditional Rental Income: $3528 Airbnb ROI: -2.87% Traditional ROI: 1.24%
4 Lighthouse Lndg Ph 501 Sleepy Hollow, NY 4 Lighthouse Lndg Ph 501, Sleepy Hollow, NY 10591 \| Condo/Coop	2 beds \| 2 baths \| 1,296 sq.ft.	$1,540,000	Airbnb cash on cash: -1.94% Traditional cash on cash: -1.19% Airbnb Rental Income: $3084 Traditional Rental Income: $3461 Airbnb ROI: -1.94% Traditional ROI: -1.19%

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

There are 39 investment properties available for sale in Sleepy-hollow.

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

The ROI for Short-Term is higher than the Long-Term in Sleepy-hollow with average rental income of $N/A.

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: -1.45%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $3084

Traditional Rental Income: $4324

Airbnb ROI: -1.45%

Traditional ROI: 0.3%

34 Andrews Ln

Sleepy Hollow, NY

2 beds | 3 baths | 1,512 sq.ft.

$899,999

Airbnb cash on cash: -1.59%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $3084

Traditional Rental Income: $4313

Airbnb ROI: -1.59%

Traditional ROI: 0.71%

42 Andrews Ln

Sleepy Hollow, NY

2 beds | 3 baths | 1,512 sq.ft.

$999,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 0.54%

Airbnb Rental Income: $3084

Traditional Rental Income: $4306

Airbnb ROI: -1.54%

Traditional ROI: 0.54%

167 Millard Avenue

Sleepy Hollow, NY

4 beds | 5 baths | 5,700 sq.ft.

$3,300,000

Airbnb cash on cash: -2.28%

Traditional cash on cash: -0.63%

Airbnb Rental Income: $2397

Traditional Rental Income: $6867

Airbnb ROI: -2.28%

Traditional ROI: -0.63%

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: -3.93%

Traditional cash on cash: -0.88%

Airbnb Rental Income: $176

Traditional Rental Income: $4204

Airbnb ROI: -3.93%

Traditional ROI: -0.88%

4 Lighthouse Lndg #210

Sleepy Hollow, NY

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

$3,795,000

Airbnb cash on cash: -3.38%

Traditional cash on cash: -2.04%

Airbnb Rental Income: $176

Traditional Rental Income: $4667

Airbnb ROI: -3.38%

Traditional ROI: -2.04%

4 Lighthouse Lndg #TH13

Sleepy Hollow, NY

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

$1,550,000

Airbnb cash on cash: -2.46%

Traditional cash on cash: -1%

Airbnb Rental Income: $3084

Traditional Rental Income: $4482

Airbnb ROI: -2.46%