Pleasantville

Westchester County, New York

VIEW 62 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

32 Guion Street
Pleasantville, NY $875,000

32 Guion Street

Pleasantville, NY

$875,000
  • 4 Beds
  • 1/1 Baths
  • 1,982 Sqft
37 Broadway #2C
Pleasantville, NY $239,000

37 Broadway #2C

Pleasantville, NY

$239,000
  • 2 Beds
  • 1 Baths
  • 900 Sqft
49 Marble Avenue
Pleasantville, NY $2,795,000

49 Marble Avenue

Pleasantville, NY

$2,795,000
  • 13,460 Sqft
66 Heritage Drive
Pleasantville, NY $1,795,000

66 Heritage Drive

Pleasantville, NY

$1,795,000
  • 5 Beds
  • 3/1 Baths
  • 5,160 Sqft
23 Heritage Drive
Pleasantville, NY $1,439,000

23 Heritage Drive

Pleasantville, NY

$1,439,000
  • 4 Beds
  • 2/1 Baths
  • 2,853 Sqft
114 Ashland Avenue
Pleasantville, NY $1,399,000

114 Ashland Avenue

Pleasantville, NY

$1,399,000
  • 4 Beds
  • 3/1 Baths
  • 3,402 Sqft
67 Heritage Drive
Pleasantville, NY $1,329,000

67 Heritage Drive

Pleasantville, NY

$1,329,000
  • 4 Beds
  • 2/1 Baths
  • 4,896 Sqft
114 Deerfield Lane N
Pleasantville, NY $1,325,000

114 Deerfield Lane N

Pleasantville, NY

$1,325,000
  • 4 Beds
  • 3/1 Baths
  • 3,374 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

February 2024

2 TOTAL UNITS

image description -33.3% image description -66.7% vs

Median Sales Price

February 2024 - Single Family Homes

$970K
image description +19.0% image description +16.4% vs

Percentage of Asking Price

February 2024 Single Family Homes

88%
image description +3.5% image description -10.0% vs
88%
image description +3.5% image description -10.0% vs
88%
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