Pleasantville

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

42 Old Sleepy Hollow Road
Pleasantville, NY $2,665,000

42 Old Sleepy Hollow Road

Pleasantville, NY

$2,665,000
  • 4 Beds
  • 4/1 Baths
  • 6,677 Sqft
4 Old Farm Road S
Pleasantville, NY $1,825,000

4 Old Farm Road S

Pleasantville, NY

$1,825,000
  • 4 Beds
  • 4/1 Baths
  • 5,298 Sqft
182 Fairview Drive
Pleasantville, NY $899,999

182 Fairview Drive

Pleasantville, NY

$899,999
  • 3 Beds
  • 2 Baths
  • 2,586 Sqft
399 Old Sleepy Hollow Road
Pleasantville, NY $899,000

399 Old Sleepy Hollow Road

Pleasantville, NY

$899,000
  • 3.21 Acres
66 Old Farm Road S
Pleasantville, NY $1,699,999

66 Old Farm Road S

Pleasantville, NY

$1,699,999
  • 4 Beds
  • 4/1 Baths
  • 4,067 Sqft
33 Ashland Avenue
Pleasantville, NY $1,580,000

33 Ashland Avenue

Pleasantville, NY

$1,580,000
  • 4 Beds
  • 3/1 Baths
  • 3,600 Sqft
5 Heritage Drive
Pleasantville, NY $1,290,000

5 Heritage Drive

Pleasantville, NY

$1,290,000
  • 4 Beds
  • 3/1 Baths
  • 3,245 Sqft
6 Bayberry Drive
Pleasantville, NY $1,200,000

6 Bayberry Drive

Pleasantville, NY

$1,200,000
  • 3 Beds
  • 2 Baths
  • 1,960 Sqft

Pleasantville

Area Map

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Pleasantville

(Pleasantville School District)

Market Snapshot

Units Sold

February 2023

3 TOTAL UNITS

image description -57.1% image description -62.5% vs

Median Sales Price

February 2023 - Single Family Homes

$815K
image description -2.2% image description -3.0% vs

Percentage of Asking Price

February 2023 Single Family Homes

85%
image description -13.1% image description -14.9% vs
85%
image description -13.1% image description -14.9% vs
85%
image description -13.1% image description -14.9% vs