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

11 Rockledge Road
Pleasantville, NY $1,999,500

11 Rockledge Road

Pleasantville, NY

$1,999,500
  • 4 Beds
  • 4 Baths
  • 5,214 Sqft
559 Bedford Road #1st Floor
Pleasantville, NY $2,800/mo

559 Bedford Road #1st Floor

Pleasantville, NY

$2,800/mo
  • 1 Beds
  • 1/4 Baths
  • 950 Sqft
110 Columbus #2
Pleasantville, NY $2,500/mo

110 Columbus #2

Pleasantville, NY

$2,500/mo
  • 1 Beds
  • 1 Baths
  • 1,018 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
17 Marble Avenue
Pleasantville, NY $2,990,000

17 Marble Avenue

Pleasantville, NY

$2,990,000
  • 17,588 Sqft
20 Clark Street
Pleasantville, NY $2,200,000

20 Clark Street

Pleasantville, NY

$2,200,000
  • 5 Beds
  • 4/1 Baths
  • 4,100 Sqft
11 Vista Court
Pleasantville, NY $2,200,000

11 Vista Court

Pleasantville, NY

$2,200,000
  • 6 Beds
  • 4/2 Baths
  • 8,685 Sqft
325 Manville Road
Pleasantville, NY $1,775,000

325 Manville Road

Pleasantville, NY

$1,775,000
  • 5,786 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

Market Snapshot

Units Sold

December 2024

5 TOTAL UNITS

image description +66.7% image description -16.7% since

Median Sales Price

December 2024 - Single Family Homes

$698K
image description -36.5% image description -20.7% since

Percentage of Asking Price

December 2024 Single Family Homes

102%
image description +2.3% image description +6.1% since
102%
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102%
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102%
image description +2.3% image description +6.1% since