Pleasantville

Westchester County, New York

VIEW 35 COMMUNITY LISTINGS

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

11 Roselle Avenue
Pleasantville, NY $1,175,000

11 Roselle Avenue

Pleasantville, NY

$1,175,000
  • 3 Beds
  • 3 Baths
  • 2,393 Sqft
300 Washington Avenue
Pleasantville, NY $999,000

300 Washington Avenue

Pleasantville, NY

$999,000
  • 4 Beds
  • 4 Baths
  • 2,184 Sqft
5 Church Street  #1P
Pleasantville, NY $255,000

5 Church Street #1P

Pleasantville, NY

$255,000
  • 2 Beds
  • 1 Baths
  • 900 Sqft
6 Raven Way
Pleasantville, NY $7,500/mo

6 Raven Way

Pleasantville, NY

$7,500/mo
  • 4 Beds
  • 4 Baths
  • 2,437 Sqft
39 Washington Avenue  #209
Pleasantville, NY $4,850/mo

39 Washington Avenue #209

Pleasantville, NY

$4,850/mo
  • 2 Beds
  • 2 Baths
  • 948 Sqft
413-415 Bedford Road
Pleasantville, NY $2,825,000

413-415 Bedford Road

Pleasantville, NY

$2,825,000
  • 0.33 Acres
235 Bear Ridge Road
Pleasantville, NY $2,350,000

235 Bear Ridge Road

Pleasantville, NY

$2,350,000
  • 6 Beds
  • 4/1 Baths
  • 7,722 Sqft
26 Club Court
Pleasantville, NY $1,499,999

26 Club Court

Pleasantville, NY

$1,499,999
  • 2 Beds
  • 3/1 Baths
  • 4,132 Sqft

Pleasantville

Area Map

Pleasantville is within Westchester County, New York and borders Briarcliff Manor and Chappaqua.

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Featured Communities Within

Westchester County

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Pleasantville

(Pleasantville School District)

Market Snapshot

Units Sold

January 2026

7 TOTAL UNITS

image description +16.7% image description +133.3% vs

Median Sales Price

January 2026 - Single Family Homes

$1.1M
image description -10.5% image description -20.6% vs

Percentage of Asking Price

January 2026 Single Family Homes

98%
image description -3.7% image description -11.2% vs
98%
image description -3.7% image description -11.2% vs
98%
image description -3.7% image description -11.2% vs
98%
image description -3.7% image description -11.2% vs