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Pleasantville

Westchester County, New York

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Pleasantville is a charming village in Westchester County New York, blending urban and suburban sensibilities, neighborliness, and tranquility.

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

Pleasantville is a charming village in the Town of Mount Pleasant,New York, in Westchester County which blends 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 walking to 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, exceptional public schools, a wealth of culture and community events and a closeness of community makes Pleasantville a desirable place to call home.

Present-day Pleasantville dates back to the settlement of an Iroquois tribe which grew corn here and established trading routes prior to the arrival of European settlers in the late 1600’s. The area’s development 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 desirable, modern suburb of New York.

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Lifestyle Features

Lifestyle Feature

Commuter Friendly

Providing an ideal balance between urban amenities and the suburban lifestyle, Fairfield County offers many excellent real estate choices for the New York City commuter. With its easy access to midtown Manhattan by Metro-North railroad, Fairfield County serves as a perfect city escape while still offering fantastic proximity. Start your search for commuter friendly listings here.

  • 6,938 Listings Within 90 minutes
    of Midtown Manhattan
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Getting to the City

Pleasantville is conveniently located about 31 miles north of New York City, and a 50-minute ride from Grand Central Terminal via Metro-North's Harlem Line.

Calculate your commute time

49 MINUTES
TO GRAND CENTRAL STATION

Travel times provided by Google - view all terms and conditions.

Featured Listings

36 Hillside Avenue
Pleasantville, NY $805,000

36 Hillside Avenue

Pleasantville, NY

$805,000
  • 6 Beds
  • 2/1 Baths
  • 2,251 Sqft
48 Cedar Avenue
Pleasantville, NY $789,000

48 Cedar Avenue

Pleasantville, NY

$789,000
  • 4 Beds
  • 2/1 Baths
  • 2,892 Sqft
443 Bear Ridge Road
Pleasantville, NY $629,000

443 Bear Ridge Road

Pleasantville, NY

$629,000
  • 3 Beds
  • 2 Baths
  • 1,965 Sqft
19 Grandview Avenue
Pleasantville, NY $3,500/mo

19 Grandview Avenue

Pleasantville, NY

$3,500/mo
  • 3 Beds
  • 1/1 Baths
  • 1,652 Sqft
204 Old Sleepy Hollow Road
Pleasantville, NY $2,800,000

204 Old Sleepy Hollow Road

Pleasantville, NY

$2,800,000
  • 560,181 Sqft
13 Crestview Drive
Pleasantville, NY $1,399,000

13 Crestview Drive

Pleasantville, NY

$1,399,000
  • 5 Beds
  • 3/1 Baths
  • 5,374 Sqft
58 Beech Hill Road
Pleasantville, NY $1,358,000

58 Beech Hill Road

Pleasantville, NY

$1,358,000
  • 5 Beds
  • 5/1 Baths
  • 6,100 Sqft
5 Spruce Hill Court
Pleasantville, NY $1,299,000

5 Spruce Hill Court

Pleasantville, NY

$1,299,000
  • 4 Beds
  • 3/1 Baths
  • 4,120 Sqft

Pleasantville

Area Map

Pleasantville is within Westchester County, New York and borders Briarcliff Manor and Chappaqua.

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Westchester County

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Pleasantville

Market Snapshot

Units Sold

October 2019

9 TOTAL UNITS

image description +0.0% image description -10.0% since

Median Sales Price

October 2019 - Single Family Homes

$750K
image description -17.4% image description +20.5% since

Percentage of Asking Price

October 2019 Single Family Homes

97%
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97%
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97%
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97%
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