Pleasantville

Westchester County, New York

VIEW 58 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

306 Mountain Road
Pleasantville, NY $1,425,000

306 Mountain Road

Pleasantville, NY

$1,425,000
  • 4 Beds
  • 2/1 Baths
  • 3,800 Sqft
60 Cedar Avenue
Pleasantville, NY $1,099,000

60 Cedar Avenue

Pleasantville, NY

$1,099,000
  • 4 Beds
  • 2/2 Baths
  • 2,461 Sqft
55 Sarles Lane
Pleasantville, NY $899,000

55 Sarles Lane

Pleasantville, NY

$899,000
  • 3 Beds
  • 1/1 Baths
  • 1,770 Sqft
33 Roselle Avenue  #M
Pleasantville, NY $549,000

33 Roselle Avenue #M

Pleasantville, NY

$549,000
  • 1 Beds
  • 1 Baths
  • 1,190 Sqft
14 Mountain Trail
Pleasantville, NY $3,950/mo

14 Mountain Trail

Pleasantville, NY

$3,950/mo
  • 2 Beds
  • 1 Baths
  • 901 Sqft
413-415 Bedford Road
Pleasantville, NY $2,998,000

413-415 Bedford Road

Pleasantville, NY

$2,998,000
  • 0.33 Acres
29 Cedar Lane
Pleasantville, NY $1,899,000

29 Cedar Lane

Pleasantville, NY

$1,899,000
  • 4 Beds
  • 3/1 Baths
  • 3,917 Sqft
112 Great Oak Lane
Pleasantville, NY $1,600,000

112 Great Oak Lane

Pleasantville, NY

$1,600,000
  • 4 Beds
  • 3/1 Baths
  • 2,467 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

August 2025

10 TOTAL UNITS

image description -9.1% image description +0.0% vs

Median Sales Price

August 2025 - Single Family Homes

$998K
image description -10.8% image description +21.7% vs

Percentage of Asking Price

August 2025 Single Family Homes

97%
image description -11.6% image description -6.5% vs
97%
image description -11.6% image description -6.5% vs
97%
image description -11.6% image description -6.5% vs
97%
image description -11.6% image description -6.5% vs