Pleasantville

Westchester County, New York

VIEW 40 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

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
32 Orchard Street
Pleasantville, NY $1,199,000

32 Orchard Street

Pleasantville, NY

$1,199,000
  • 7 Beds
  • 5/1 Baths
  • 3,501 Sqft
399 Old Sleepy Hollow Road
Pleasantville, NY $899,000

399 Old Sleepy Hollow Road

Pleasantville, NY

$899,000
  • 3.21 Acres
16 Summit Place
Pleasantville, NY $555,000

16 Summit Place

Pleasantville, NY

$555,000
  • 3 Beds
  • 1/1 Baths
  • 1,653 Sqft
135 Deerfield Lane N
Pleasantville, NY $1,695,000

135 Deerfield Lane N

Pleasantville, NY

$1,695,000
  • 3 Beds
  • 3/1 Baths
  • 3,701 Sqft
7 Grove Street
Pleasantville, NY $1,450,000

7 Grove Street

Pleasantville, NY

$1,450,000
  • 5 Beds
  • 4 Baths
  • 3,294 Sqft
37 Pheasant Run Road
Pleasantville, NY $1,399,000

37 Pheasant Run Road

Pleasantville, NY

$1,399,000
  • 4 Beds
  • 2/1 Baths
  • 3,663 Sqft
45 Suzanne Lane
Pleasantville, NY $1,315,000

45 Suzanne Lane

Pleasantville, NY

$1,315,000
  • 4 Beds
  • 2/1 Baths
  • 3,050 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 2023

9 TOTAL UNITS

image description -40.0% image description -10.0% vs

Median Sales Price

August 2023 - Single Family Homes

$823K
image description -4.9% image description -17.1% vs

Percentage of Asking Price

August 2023 Single Family Homes

106%
image description +3.4% image description +5.5% vs
106%
image description +3.4% image description +5.5% vs
106%
image description +3.4% image description +5.5% vs