Pleasantville

Pleasantville is a charming village in Westchester County New York, blending urban and suburban sensibilities, neighborliness, and tranquility.

The village’s relatively compact size at 1.8 square miles, means that its sidewalks get plenty of use. Residents enjoy local events and activities, meeting up with neighbors and friends at the local farmers market, and patronizing local shops, restaurants and cafes. The village, which at one time housed the headquarters of Reader’s Digest, is also known for its rich literary history and is home to numerous writers, editors and novelists who enjoy its close proximity to New York. An outstanding public library, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Pleasantville evolved with the later arrival of the New York Central Railroad. Prior to the 1800’s, Pleasantville was referred to as Leggett’s Corner, and then Clark’s Corner, named after local property owner Henry Clark. In 1828 the village’s present name was chosen by its postmaster, Henry Romer. By the 1870’s Pleasantville experienced rapid growth and was home to numerous businesses, including a pickle factory, and local farmland was replaced by residential subdivisions and stately Victorian homes for the burgeoning middle class. The village was incorporated on March 16, 1897, and Pleasantville soon evolved into a modern suburb of New York.

The village’s relatively compact size at 1.8 square miles, means that its sidewalks get plenty of use. Residents enjoy local events and activities, meeting up with neighbors and friends at the local farmers market, and patronizing local shops, restaurants and cafes. The village, which at one time housed the headquarters of Reader’s Digest, is also known for its rich literary history and is home to numerous writers, editors and novelists who enjoy its close proximity to New York. An outstanding public library, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Pleasantville evolved with the later arrival of the New York Central Railroad. Prior to the 1800’s, Pleasantville was referred to as Leggett’s Corner, and then Clark’s Corner, named after local property owner Henry Clark. In 1828 the village’s present name was chosen by its postmaster, Henry Romer. By the 1870’s Pleasantville experienced rapid growth and was home to numerous businesses, including a pickle factory, and local farmland was replaced by residential subdivisions and stately Victorian homes for the burgeoning middle class. The village was incorporated on March 16, 1897, and Pleasantville soon evolved into a modern suburb of New York.

The village’s relatively compact size at 1.8 square miles, means that its sidewalks get plenty of use. Residents enjoy local events and activities, meeting up with neighbors and friends at the local farmers market, and patronizing local shops, restaurants and cafes. The village, which at one time housed the headquarters of Reader’s Digest, is also known for its rich literary history and is home to numerous writers, editors and novelists who enjoy its close proximity to New York. An outstanding public library, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Pleasantville evolved with the later arrival of the New York Central Railroad. Prior to the 1800’s, Pleasantville was referred to as Leggett’s Corner, and then Clark’s Corner, named after local property owner Henry Clark. In 1828 the village’s present name was chosen by its postmaster, Henry Romer. By the 1870’s Pleasantville experienced rapid growth and was home to numerous businesses, including a pickle factory, and local farmland was replaced by residential subdivisions and stately Victorian homes for the burgeoning middle class. The village was incorporated on March 16, 1897, and Pleasantville soon evolved into a modern suburb of New York.

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Featured Listings

32 Larrys Lane
Pleasantville, NY $1,399,000

32 Larrys Lane

Pleasantville, NY

$1,399,000
  • 4 Beds
  • 4/1 Baths
  • 4,397 Sqft
6 Raven Way
Pleasantville, NY $1,299,000

6 Raven Way

Pleasantville, NY

$1,299,000
  • 4 Beds
  • 4 Baths
  • 2,437 Sqft
190 Lake Shore Drive
Pleasantville, NY $915,000

190 Lake Shore Drive

Pleasantville, NY

$915,000
  • 4 Beds
  • 2/1 Baths
  • 2,464 Sqft
14 Mountain Trail
Pleasantville, NY $499,000

14 Mountain Trail

Pleasantville, NY

$499,000
  • 2 Beds
  • 1 Baths
  • 942 Sqft
37 Broadway #2C
Pleasantville, NY $239,000

37 Broadway #2C

Pleasantville, NY

$239,000
  • 2 Beds
  • 1 Baths
  • 900 Sqft
413-415 Bedford Road
Pleasantville, NY $3,495,000

413-415 Bedford Road

Pleasantville, NY

$3,495,000
  • 8,072 Sqft
66 Heritage Drive
Pleasantville, NY $1,795,000

66 Heritage Drive

Pleasantville, NY

$1,795,000
  • 5 Beds
  • 3/1 Baths
  • 5,160 Sqft
135 Deerfield Lane N
Pleasantville, NY $1,695,000

135 Deerfield Lane N

Pleasantville, NY

$1,695,000
  • 3 Beds
  • 3/1 Baths
  • 3,701 Sqft

Pleasantville

Area Map

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Pleasantville

(Pleasantville School District)

Market Snapshot

Units Sold

January 2024

3 TOTAL UNITS

image description -40.0% image description -76.9% vs

Median Sales Price

January 2024 - Single Family Homes

$1.4M
image description +116.9% image description +85.4% vs

Percentage of Asking Price

January 2024 Single Family Homes

110%
image description +11.8% image description +14.6% vs
110%
image description +11.8% image description +14.6% vs
110%
image description +11.8% image description +14.6% vs