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Pleasantville

Westchester County, New York

VIEW 49 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

11 Rockledge Road
Pleasantville, NY $1,999,500

11 Rockledge Road

Pleasantville, NY

$1,999,500
  • 4 Beds
  • 4 Baths
  • 5,214 Sqft
GET MORE DETAILS
30 Broadway
Pleasantville, NY $589,900

30 Broadway

Pleasantville, NY

$589,900
  • 3 Beds
  • 2 Baths
  • 1,660 Sqft
GET MORE DETAILS
68 Columbus Avenue #2
Pleasantville, NY $2,750/mo

68 Columbus Avenue #2

Pleasantville, NY

$2,750/mo
  • 2 Beds
  • 1 Baths
  • 943 Sqft
GET MORE DETAILS
235 Bear Ridge Road
Pleasantville, NY $3,300,000

235 Bear Ridge Road

Pleasantville, NY

$3,300,000
  • 6 Beds
  • 4/1 Baths
  • 7,722 Sqft
GET MORE DETAILS
325 Manville Road
Pleasantville, NY $1,775,000

325 Manville Road

Pleasantville, NY

$1,775,000
  • 5,786 Sqft
GET MORE DETAILS
177 Deerfield Lane N
Pleasantville, NY $1,599,000

177 Deerfield Lane N

Pleasantville, NY

$1,599,000
  • 4 Beds
  • 3/1 Baths
  • 3,197 Sqft
GET MORE DETAILS
214 Edgewood Avenue
Pleasantville, NY $1,399,999

214 Edgewood Avenue

Pleasantville, NY

$1,399,999
  • 6 Beds
  • 2/1 Baths
  • 2,856 Sqft
GET MORE DETAILS
133 Lake Shore Drive
Pleasantville, NY $1,299,000

133 Lake Shore Drive

Pleasantville, NY

$1,299,000
  • 3 Beds
  • 2/1 Baths
  • 2,900 Sqft
GET MORE DETAILS
view all 49 Pleasantville listings

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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  • 33 Pound Ridge
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  • 102 Rye
  • 49 Rye Brook

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  • 169 Rye Town
  • 227 Scarsdale
  • 85 Sleepy Hollow
  • 27 South Salem
  • 62 Tarrytown
  • 35 Tuckahoe
  • 3 Waccabuc
  • 341 White Plains
  • 736 Yonkers
  • 121 Yorktown
+-

Pleasantville

(Pleasantville School District)

Market Snapshot

Average Days on Market

Single Family Homes

63 February 2025
image description +9.6% image description -34.6% vs

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Avg. Price Sqft

Single Family Homes

$431 February 2025
image description +69.8% image description +74.0% vs

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Units Sold

February 2025

3 TOTAL UNITS

image description +50.0% image description +0.0% vs

Median Sales Price

February 2025 - Single Family Homes

$790K
image description -18.6% image description -3.1% vs

Percentage of Asking Price

February 2025 Single Family Homes

96%
image description +8.9% image description +12.8% vs
96%
image description +8.9% image description +12.8% vs
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