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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
46 Andrews LaneSleepy Hollow, NYWelcome 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: -1.27%
|
34 Andrews LaneSleepy Hollow, NYWelcome 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: -1.37%
|
42 Andrews LaneSleepy Hollow, NYWelcome home to Sunset Villas on Andrews Lane. A new community of nine luxury townhomes (f... |
2 beds | 4 baths | 1,512 sq.ft. |
$999,000 |
Airbnb cash on cash: -1.33%
|
167 Millard AvenueSleepy Hollow, NYAs 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: -1.83%
|
48 Raafenberg RdSleepy Hollow, NY48 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
|
11 River Street #401Sleepy Hollow, NYThis 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: -3.83%
|
4 Lighthouse Lndg #210Sleepy Hollow, NY4 Lighthouse Lndg #210, Sleepy Hollow, NY 10591 | Condo/Coop |
3 beds | 3 baths | 2,357 sq.ft. |
$3,895,000 |
Airbnb cash on cash: -3.33%
|
4 Lighthouse Lndg #TH13Sleepy Hollow, NY4 Lighthouse Lndg #TH13, Sleepy Hollow, NY 10591 | Condo/Coop |
2 beds | 3 baths | 2,101 sq.ft. |
$1,690,000 |
Airbnb cash on cash: -2.36%
|
4 Lighthouse Lndg #TH14Sleepy Hollow, NY4 Lighthouse Lndg #TH14, Sleepy Hollow, NY 10591 | Condo/Coop |
3 beds | 4 baths | 3,093 sq.ft. |
$2,620,000 |
Airbnb cash on cash: -3.89%
|
32 Andrews LaneSleepy Hollow, NYWelcome 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: -1.37%
|
4 Lighthouse Lndg #204Sleepy Hollow, NY4 Lighthouse Lndg #204, Sleepy Hollow, NY 10591 | Condo/Coop |
3 beds | 3 baths | 2,356 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -3.3%
|
34 Hemlock DriveSleepy Hollow, NYThis 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: -0.98%
|
203 Palisades BoulevardSleepy Hollow, NYPlease send pof or pre app to phyllis before showing...Beautiful 4-bedroom, 3 full and 2 h... |
4 beds | 5 baths | 2,936 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -1.73%
|
201 Horseman Boulevard #101Sleepy Hollow, NYWelcome 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: -1.59%
|
46 Andrews Lane #46Sleepy Hollow, NYWelcome 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: -0.84%
|
42 Andrews Lane #42Sleepy Hollow, NYWelcome 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: -0.28%
|
30 Kendall AveSleepy Hollow, NY30 Kendall Ave, Sleepy Hollow, NY 10591 | Single Family Residential |
3 beds | 2 baths | 2,200 sq.ft. |
$599,900 |
Airbnb cash on cash: -2.7%
|
206 Legend DrSleepy Hollow, NY206 Legend Dr, Sleepy Hollow, NY 10591 | Single Family Residential |
4 beds | 3 baths | 2,676 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -1.03%
|
4 Lighthouse Lndg #424Sleepy Hollow, NY4 Lighthouse Lndg #424, Sleepy Hollow, NY 10591 | Condo/Coop |
3 beds | 2 baths | 1,886 sq.ft. |
$3,115,000 |
Airbnb cash on cash: -3.31%
|
49 Howard StreetSleepy Hollow, NYThis 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
|
17 Anderson AvenueSleepy Hollow, NYNestled 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: -3.18%
|
30 Andrews LaneSleepy Hollow, NYWelcome 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: -1.33%
|
36 Andrews LaneSleepy Hollow, NYWelcome 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: -1.33%
|
144 Beekman AvenueSleepy Hollow, NYRare Sleepy Hollow 2-Family Double-Duplex with River & Bridge Views.....!! This opportunit... |
5 beds | 4 baths | N/A |
$1,500,000 |
Airbnb cash on cash: N/A
|
34 Cedar StSleepy Hollow, NY34 Cedar St, Sleepy Hollow, NY 10591 | Multi Family |
5 beds | 2 baths | 1,991 sq.ft. |
$699,000 |
Airbnb cash on cash: N/A
|
324 Horseman BoulevardSleepy Hollow, NYThe Layout and First Impressions Living in this modern, four-level end-unit brownstone is ... |
4 beds | 5 baths | 2,646 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -1.93%
|
12 Webb RoadSleepy Hollow, NYSituated 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
|
102 Legend Dr #301Sleepy Hollow, NY102 Legend Dr #301, Sleepy Hollow, NY 10591 | Condo/Coop |
1 beds | 1 baths | 1,178 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -2.67%
|
100 Legend Dr #206Sleepy Hollow, NY100 Legend Dr #206, Sleepy Hollow, NY 10591 | Condo/Coop |
2 beds | 2 baths | 1,190 sq.ft. |
$1,249,500 |
Airbnb cash on cash: -1.37%
|
207 Palisades BlvdSleepy Hollow, NY207 Palisades Blvd, Sleepy Hollow, NY 10591 | Condo/Coop |
4 beds | 3 baths | 3,051 sq.ft. |
$2,100,000 |
Airbnb cash on cash: -1.43%
|
4 Lighthouse Lndg #305Sleepy Hollow, NY4 Lighthouse Lndg #305, Sleepy Hollow, NY 10591 | Condo/Coop |
2 beds | 2 baths | 1,688 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -2.21%
|
340 Horseman BlvdSleepy Hollow, NY340 Horseman Blvd, Sleepy Hollow, NY 10591 | Condo/Coop |
4 beds | 3 baths | 3,060 sq.ft. |
$2,175,000 |
Airbnb cash on cash: -1.48%
|
10 Clinton StreetSleepy Hollow, NYExceptional investment opportunity in the heart of Sleepy Hollow! This legal two-family pr... |
4 beds | 2 baths | N/A |
$479,500 |
Airbnb cash on cash: 5.45%
|
62 Hemlock DriveSleepy Hollow, NYDiscover timeless Colonial charm at 62 Hemlock Drive, ideally situated in the sought-after... |
4 beds | 3 baths | 2,032 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -0.36%
|
Real Estate investment in Sleepy-hollow, NY
There are 34 properties for sale in the city of Sleepy Hollow . The median list price in Sleepy Hollow is $1,677,496 and the average price per square foot is $723. In July 2026, the average monthly cash on cash return in Sleepy Hollow is N/A%. The average monthly rental income in Sleepy Hollow is $4,319.