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

26 Cecilia Lane
Pleasantville, NY $2,299,000

26 Cecilia Lane

Pleasantville, NY

$2,299,000
  • 5 Beds
  • 3/2 Baths
  • 5,055 Sqft
54 High View Terrace
Pleasantville, NY $760,000

54 High View Terrace

Pleasantville, NY

$760,000
  • 3 Beds
  • 1 Baths
  • 1,930 Sqft
16 Locust Road
Pleasantville, NY $7,900/mo

16 Locust Road

Pleasantville, NY

$7,900/mo
  • 4 Beds
  • 2/1 Baths
  • 2,354 Sqft
413-415 Bedford Road
Pleasantville, NY $2,600,000

413-415 Bedford Road

Pleasantville, NY

$2,600,000
  • 8,320 Sqft
2 Broadway
Pleasantville, NY $1,900,000

2 Broadway

Pleasantville, NY

$1,900,000
  • 4,091 Sqft
8 Heritage Drive
Pleasantville, NY $1,750,000

8 Heritage Drive

Pleasantville, NY

$1,750,000
  • 4 Beds
  • 3 Baths
  • 3,750 Sqft
39 Choate Lane
Pleasantville, NY $1,600,000

39 Choate Lane

Pleasantville, NY

$1,600,000
  • 5 Beds
  • 3/1 Baths
  • 3,802 Sqft
32 Eastview Avenue
Pleasantville, NY $1,599,999

32 Eastview Avenue

Pleasantville, NY

$1,599,999
  • 4 Beds
  • 3/1 Baths
  • 3,400 Sqft

Pleasantville

Area Map

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Pleasantville

(Pleasantville School District)

Market Snapshot

Units Sold

October 2026

6 TOTAL UNITS

image description -33.3% image description +50.0% vs

Median Sales Price

October 2026 - Single Family Homes

$915K
image description -32.2% image description -20.4% vs

Percentage of Asking Price

October 2026 Single Family Homes

103%
image description +5.3% image description +10.0% vs
103%
image description +5.3% image description +10.0% vs
103%
image description +5.3% image description +10.0% vs
103%
image description +5.3% image description +10.0% vs
103%
image description +5.3% image description +10.0% vs