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Pleasantville

Westchester County, New York

VIEW 60 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

80 Oak Ridge Road
Pleasantville, NY $949,000

80 Oak Ridge Road

Pleasantville, NY

$949,000
  • 3 Beds
  • 2 Baths
  • 2,100 Sqft
GET MORE DETAILS
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
385 Lake Shore Drive
Pleasantville, NY $849,000

385 Lake Shore Drive

Pleasantville, NY

$849,000
  • 4 Beds
  • 2 Baths
  • 2,048 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
224 Bedford Road
Pleasantville, NY $2,550/mo

224 Bedford Road

Pleasantville, NY

$2,550/mo
  • 1 Beds
  • 1 Baths
  • 650 Sqft
GET MORE DETAILS
413-415 Bedford Road
Pleasantville, NY $2,998,000

413-415 Bedford Road

Pleasantville, NY

$2,998,000
  • 0.33 Acres
GET MORE DETAILS
22 Clark Street
Pleasantville, NY $1,989,000

22 Clark Street

Pleasantville, NY

$1,989,000
  • 8 Beds
  • 5/2 Baths
  • 4,983 Sqft
GET MORE DETAILS
view all 60 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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  • 138 Hartsdale
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  • 60 Katonah
  • 159 Larchmont
  • 137 Mamaroneck
  • 103 Mount Kisco
  • 223 Mount Pleasant
  • 307 Mount Vernon
  • 336 New Rochelle
  • 34 North Salem
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  • 84 Pelham
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  • 115 Port Chester
  • 41 Pound Ridge
  • 31 Purchase
  • 139 Rye
  • 64 Rye Brook

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  • 221 Rye Town
  • 290 Scarsdale
  • 81 Sleepy Hollow
  • 44 South Salem
  • 59 Tarrytown
  • 37 Tuckahoe
  • 11 Waccabuc
  • 411 White Plains
  • 639 Yonkers
  • 12 Yorktown
+-

Pleasantville

(Pleasantville School District)

Market Snapshot

Average Days on Market

Single Family Homes

16 May 2025
image description -71.0% image description -35.9% vs

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Avg. Price Sqft

Single Family Homes

$443 May 2025
image description +11.0% image description +3.5% vs

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Units Sold

May 2025

6 TOTAL UNITS

image description -45.5% image description -33.3% vs

Median Sales Price

May 2025 - Single Family Homes

$800K
image description -22.0% image description -3.1% vs

Percentage of Asking Price

May 2025 Single Family Homes

103%
image description +1.0% image description -5.0% vs
103%
image description +1.0% image description -5.0% vs
103%
image description +1.0% image description -5.0% vs
103%
image description +1.0% image description -5.0% vs
103%
image description +1.0% image description -5.0% vs
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