Pleasantville Real Estate Guide

Westchester County, New York

VIEW 46 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

26 Cecilia Lane
Pleasantville, NY $2,499,999

26 Cecilia Lane

Pleasantville, NY

$2,499,999
  • 5 Beds
  • 3/2 Baths
  • 5,055 Sqft
10 Crestview Drive
Pleasantville, NY $2,200,000

10 Crestview Drive

Pleasantville, NY

$2,200,000
  • 4 Beds
  • 3/1 Baths
  • 6,165 Sqft
590 Bedford Road  #3
Pleasantville, NY $475,000

590 Bedford Road #3

Pleasantville, NY

$475,000
  • 2 Beds
  • 1 Baths
  • 900 Sqft
590 Bedford Road  #22
Pleasantville, NY $389,000

590 Bedford Road #22

Pleasantville, NY

$389,000
  • 1 Beds
  • 1 Baths
  • 750 Sqft
15 Heritage Drive
Pleasantville, NY $3,350,000

15 Heritage Drive

Pleasantville, NY

$3,350,000
  • 5 Beds
  • 5/1 Baths
  • 7,388 Sqft
413-415 Bedford Road
Pleasantville, NY $2,600,000

413-415 Bedford Road

Pleasantville, NY

$2,600,000
  • 8,320 Sqft
2 Broadway
Pleasantville, NY $1,900,000

2 Broadway

Pleasantville, NY

$1,900,000
  • 4,091 Sqft
37 Pheasant Run Road
Pleasantville, NY $1,500,000

37 Pheasant Run Road

Pleasantville, NY

$1,500,000
  • 4 Beds
  • 2/1 Baths
  • 3,663 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

September 2026

11 TOTAL UNITS

image description +120.0% image description +175.0% vs

Median Sales Price

September 2026 - Single Family Homes

$950K
image description -4.9% image description -17.6% vs

Percentage of Asking Price

September 2026 Single Family Homes

111%
image description +7.2% image description +8.4% vs
111%
image description +7.2% image description +8.4% vs
111%
image description +7.2% image description +8.4% vs
111%
image description +7.2% image description +8.4% vs
111%
image description +7.2% image description +8.4% vs
111%
image description +7.2% image description +8.4% vs