$1,175,000
- 3 Beds
- 3 Baths
- 3,728 Sq Ft
57 Hamilton Dr, Chappaqua, NY 10514

Sherry Wiggs
Houlihan Lawrence Inc.
(914) 862-7931
$1,175,000
57 Hamilton Dr, Chappaqua, NY 10514
Sherry Wiggs
Houlihan Lawrence Inc.
(914) 862-7931
$1,499,999
302 Washington Ave, Pleasantville, NY 10570
Cathy DeBow William Raveis Real Estate
$1,525,000
9 Cy Ct, Pleasantville, NY 10570
Julie Schneider Compass Greater NY, LLC
$1,425,000
306 Mountain Rd, Pleasantville, NY 10570
SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty
$1,300,000
140 Old Farm Rd S, Pleasantville, NY 10570
Sharon Foley ERA Insite Realty Services
$1,435,000
31 Pierce Dr, Pleasantville, NY 10570
Miriam Dunn RE/MAX Prime Properties
$999,999
55 Deerfield Ln S, Pleasantville, NY 10570
Tulay Erdem Christie's Int. Real Estate
$1,099,000
60 Cedar Ave, Pleasantville, NY 10570
Donna McKenna Edlund Coldwell Banker Realty
$2,650,000
14 Vista Ct, Pleasantville, NY 10570
James Garcia Coldwell Banker Realty
$1,899,000
29 Cedar Ln, Pleasantville, NY 10570
Karen O'Connor Compass Greater NY, LLC
$977,700
290 Mountain Rd, Pleasantville, NY 10570
Matthew Valvano Berkshire Hathaway HS NY Prop
$830,000
414 Bear Ridge Rd, Pleasantville, NY 10570
Stacy Weinberg Giner Real Estate Inc.
$1,025,000
27 Bedford Rd, Pleasantville, NY 10570
Grace LoBello William Raveis Real Estate
$824,000
249 Mill River Rd, Chappaqua, NY 10514
Harry Donofrio Town and Village Real Estate
Pleasantville, New York, is a small community known for its quaint homes, tree-lined streets, and strong sense of community. The town's highly rated schools, including Bedford Road School, Pleasantville Middle School, and Pleasantville High School, are part of the Pleasantville Union Free School District. The architectural landscape features New England-style colonials, Craftsman-style homes, sprawling ranchers, and custom-built properties, often set on large private lots. Residents enjoy numerous things to do, such as exploring the 45 miles of scenic trails at Rockefeller State Park Preserve or hiking and mountain biking at Graham Hills Park. The Pleasantville Country Club offers golfing opportunities, while the central downtown area is home to charming boutiques, restaurants, and annual events like Pleasantville Day. Popular dining spots include Jean Jacques and Pleasantville Diner, and The Garage at Lucy’s provides a lively atmosphere with live music and arcade games. Essential amenities such as Key Food Marketplace and LA Fitness are conveniently located, and the Jacob Burns Film Center and Pleasantville farmers market offer weekend entertainment. The town is well-connected with access to the Saw Mill River Parkway, various bus stops, and a nearby train station, making commuting to New York City, 35 miles away, straightforward.
On average, homes in Pleasantville, NY sell after 21 days on the market compared to the national average of 70 days. The median sale price for homes in Pleasantville, NY over the last 12 months is $1,400,444, up 30% from the median home sale price over the previous 12 months.
In Pleasantville, there are currently 14 houses for sale, offering an array of options for potential buyers. With houses priced between $824,000 to $2,650,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Pleasantville is $1,200,000, while the average sale price is $1,400,444, offering insights into the local housing market. On average, houses spend 21 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Pleasantville, NY and find the perfect place to call home.