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Pleasantville

Westchester County, New York

VIEW 50 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

44 Weskora Avenue
Pleasantville, NY $889,000

44 Weskora Avenue

Pleasantville, NY

$889,000
  • 4 Beds
  • 2/1 Baths
  • 2,245 Sqft
GET MORE DETAILS
24 Spring Street
Pleasantville, NY $850,000

24 Spring Street

Pleasantville, NY

$850,000
  • 4 Beds
  • 2/1 Baths
  • 2,019 Sqft
GET MORE DETAILS
24 Manville Lane #4
Pleasantville, NY $789,000

24 Manville Lane #4

Pleasantville, NY

$789,000
  • 3 Beds
  • 2/1 Baths
  • 1,627 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
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
49 Walnut Street
Pleasantville, NY $1,450,000

49 Walnut Street

Pleasantville, NY

$1,450,000
  • 6 Beds
  • 3/1 Baths
  • 3,144 Sqft
GET MORE DETAILS
view all 50 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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  • 32 Pound Ridge
  • 34 Purchase
  • 115 Rye
  • 53 Rye Brook

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  • 189 Rye Town
  • 248 Scarsdale
  • 87 Sleepy Hollow
  • 36 South Salem
  • 61 Tarrytown
  • 40 Tuckahoe
  • 4 Waccabuc
  • 369 White Plains
  • 622 Yonkers
  • 20 Yorktown
+-

Pleasantville

(Pleasantville School District)

Market Snapshot

Average Days on Market

Single Family Homes

55 March 2025

Avg. Price Sqft

Single Family Homes

$471 March 2025
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Units Sold

March 2025

4 TOTAL UNITS

image description -20.0% vs

Median Sales Price

March 2025 - Single Family Homes

$1M
image description +15.7% vs

Percentage of Asking Price

March 2025 Single Family Homes

95%
image description -4.2% vs
95%
image description -4.2% vs
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