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, 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 that 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, 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 that 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, 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 that 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

399 Old Sleepy Hollow Road
Pleasantville, NY $1,250,000

399 Old Sleepy Hollow Road

Pleasantville, NY

$1,250,000
  • 3.21 Acres
2 Great Oak Lane
Pleasantville, NY $2,300,000

2 Great Oak Lane

Pleasantville, NY

$2,300,000
  •    
6 Far Hill Lane
Pleasantville, NY $2,199,000

6 Far Hill Lane

Pleasantville, NY

$2,199,000
  • 5 Beds
  • 4/2 Baths
  • 5,735 Sqft
13 Pond Hollow Court
Pleasantville, NY $1,950,000

13 Pond Hollow Court

Pleasantville, NY

$1,950,000
  • 4 Beds
  • 2/1 Baths
  • 6,225 Sqft
22 Cecilia Lane
Pleasantville, NY $1,499,000

22 Cecilia Lane

Pleasantville, NY

$1,499,000
  • 4 Beds
  • 3/2 Baths
  • 3,547 Sqft
22 Bedford Road
Pleasantville, NY $1,495,000

22 Bedford Road

Pleasantville, NY

$1,495,000
  • 4 Beds
  • 3/1 Baths
  • 3,309 Sqft
176 Deerfield Lane N
Pleasantville, NY $1,445,000

176 Deerfield Lane N

Pleasantville, NY

$1,445,000
  • 4 Beds
  • 3/2 Baths
  • 3,411 Sqft
17 Suzanne Lane
Pleasantville, NY $1,315,000

17 Suzanne Lane

Pleasantville, NY

$1,315,000
  • 4 Beds
  • 3/1 Baths
  • 3,415 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

April 2022

9 TOTAL UNITS

image description +28.6% image description +125.0% vs

Median Sales Price

April 2022 - Single Family Homes

$784K
image description +15.3% image description +1.6% vs

Percentage of Asking Price

April 2022 Single Family Homes

104%
image description +9.8% image description +15.0% vs
104%
image description +9.8% image description +15.0% vs
104%
image description +9.8% image description +15.0% vs
104%
image description +9.8% image description +15.0% vs