Pleasantville

Westchester County, New York

VIEW 46 COMMUNITY LISTINGS

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

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

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Featured Listings

250 Washington Avenue
Pleasantville, NY $899,000

250 Washington Avenue

Pleasantville, NY

$899,000
  • 3 Beds
  • 2 Baths
  • 2,700 Sqft
50 Brentwood Drive
Pleasantville, NY $799,000

50 Brentwood Drive

Pleasantville, NY

$799,000
  • 3 Beds
  • 1/1 Baths
  • 1,811 Sqft
159 Sarles Lane
Pleasantville, NY $799,000

159 Sarles Lane

Pleasantville, NY

$799,000
  • 2 Beds
  • 2/1 Baths
  • 2,018 Sqft
624 Washington Avenue
Pleasantville, NY $649,000

624 Washington Avenue

Pleasantville, NY

$649,000
  • 3 Beds
  • 1 Baths
  • 1,326 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 $7,200/mo

6 Raven Way

Pleasantville, NY

$7,200/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 $2,950,000

413-415 Bedford Road

Pleasantville, NY

$2,950,000
  • 0.33 Acres

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

Market Snapshot

Units Sold

November 2025

9 TOTAL UNITS

image description +80.0% image description +28.6% since

Median Sales Price

November 2025 - Single Family Homes

$999K
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Percentage of Asking Price

November 2025 Single Family Homes

101%
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101%
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101%
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101%
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101%
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