Pleasantville

Westchester County, New York

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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

44 Weskora Avenue
Pleasantville, NY $889,000

44 Weskora Avenue

Pleasantville, NY

$889,000
  • 4 Beds
  • 2/1 Baths
  • 2,245 Sqft
24 Spring Street
Pleasantville, NY $850,000

24 Spring Street

Pleasantville, NY

$850,000
  • 4 Beds
  • 2/1 Baths
  • 2,019 Sqft
385 Lake Shore Drive
Pleasantville, NY $849,000

385 Lake Shore Drive

Pleasantville, NY

$849,000
  • 4 Beds
  • 2 Baths
  • 2,048 Sqft
24 Manville Lane #4
Pleasantville, NY $789,000

24 Manville Lane #4

Pleasantville, NY

$789,000
  • 3 Beds
  • 2/1 Baths
  • 1,627 Sqft
70 Memorial Plaza #204
Pleasantville, NY $4,250/mo

70 Memorial Plaza #204

Pleasantville, NY

$4,250/mo
  • 1 Beds
  • 1 Baths
  • 758 Sqft
235 Bear Ridge Road
Pleasantville, NY $3,300,000

235 Bear Ridge Road

Pleasantville, NY

$3,300,000
  • 6 Beds
  • 4/1 Baths
  • 7,722 Sqft
22 Clark Street
Pleasantville, NY $1,989,000

22 Clark Street

Pleasantville, NY

$1,989,000
  • 8 Beds
  • 5/2 Baths
  • 4,983 Sqft
117 Deerfield Lane N
Pleasantville, NY $1,695,000

117 Deerfield Lane N

Pleasantville, NY

$1,695,000
  • 4 Beds
  • 4/1 Baths
  • 4,707 Sqft

Pleasantville

Area Map

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

Featured Communities Within

Westchester County

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Pleasantville

Market Snapshot

Units Sold

March 2025

4 TOTAL UNITS

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Median Sales Price

March 2025 - Single Family Homes

$1M
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Percentage of Asking Price

March 2025 Single Family Homes

95%
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95%
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