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Pleasantville

Westchester County, New York

VIEW 69 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
2 Old Sleepy Hollow Road
Pleasantville, NY $1,475,000

2 Old Sleepy Hollow Road

Pleasantville, NY

$1,475,000
  • 4 Beds
  • 4/1 Baths
  • 3,426 Sqft
GET MORE DETAILS
45 Great Oak Lane #Apt 2
Pleasantville, NY $4,500/mo

45 Great Oak Lane #Apt 2

Pleasantville, NY

$4,500/mo
  • 4 Beds
  • 2 Baths
  • 1,905 Sqft
GET MORE DETAILS
110 Columbus Avenue #1-Upper
Pleasantville, NY $4,400/mo

110 Columbus Avenue #1-Upper

Pleasantville, NY

$4,400/mo
  • 3 Beds
  • 2 Baths
  • 1,640 Sqft
GET MORE DETAILS
45 Great Oak Lane #Apt 1
Pleasantville, NY $4,300/mo

45 Great Oak Lane #Apt 1

Pleasantville, NY

$4,300/mo
  • 3 Beds
  • 3 Baths
  • 2,207 Sqft
GET MORE DETAILS
110 Columbus #2
Pleasantville, NY $2,800/mo

110 Columbus #2

Pleasantville, NY

$2,800/mo
  • 2 Beds
  • 1 Baths
  • 1,018 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
17 Marble Avenue
Pleasantville, NY $3,200,000

17 Marble Avenue

Pleasantville, NY

$3,200,000
  • 17,588 Sqft
GET MORE DETAILS
view all 69 Pleasantville listings

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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  • 200 Rye Town
  • 200 Scarsdale
  • 83 Sleepy Hollow
  • 36 South Salem
  • 70 Tarrytown
  • 39 Tuckahoe
  • 7 Waccabuc
  • 415 White Plains
  • 680 Yonkers
  • 1 Yorktown
+-

Pleasantville

(Pleasantville School District)

Market Snapshot

Average Days on Market

Single Family Homes

61 October 2024
image description +0.8% image description +271.3% vs

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Avg. Price Sqft

Single Family Homes

$456 October 2024
image description +22.1% image description +11.5% vs

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Units Sold

October 2024

4 TOTAL UNITS

image description -20.0% image description -55.6% vs

Median Sales Price

October 2024 - Single Family Homes

$1.2M
image description +81.8% image description +29.9% vs

Percentage of Asking Price

October 2024 Single Family Homes

94%
image description -0.6% image description -9.0% vs
94%
image description -0.6% image description -9.0% vs
94%
image description -0.6% image description -9.0% vs
94%
image description -0.6% image description -9.0% vs
94%
image description -0.6% image description -9.0% vs
94%
image description -0.6% image description -9.0% vs
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