Pleasantville, NY Real Estate & Homes For Sale

9 homes

  • 267 Mountain Road, Pleasantville, NY 10570
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    $965,000
    4bd
    3ba
    3,112 sqft
    267 Mountain Road,
    Pleasantville, NY 10570
    Listing by: Houlihan Lawrence Inc.
  • 3 Northview Court, Pleasantville, NY 10570
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    0.92 ACRES
    $1,879,000
    4bd
    4ba
    5,432 sqft (on 0.92 acres)
    3 Northview Court,
    Pleasantville, NY 10570
    Listing by: Houlihan Lawrence Inc.
  • 27 Sunset Drive, Thornwood, NY 10594
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    2 ACRES
    $2,250,000
    4bd
    6ba
    6,331 sqft (on 2 acres)
    27 Sunset Drive,
    Thornwood, NY 10594
    Listing by: Julia B Fee Sothebys Int. Rlty
  • 60 Saratoga Avenue, Pleasantville, NY 10570
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    $1,250,000
    6bd
    4ba
    3,556 sqft
    60 Saratoga Avenue,
    Pleasantville, NY 10570
    Listing by: Compass Greater NY, LLC
  • 322 Sarles Lane, Pleasantville, NY 10570
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    0.26 ACRES
    $219,999
    322 Sarles Lane,
    Pleasantville, NY 10570
    Listing by: Coldwell Banker Realty
  • 133 Lake Shore Drive, Pleasantville, NY 10570
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    $979,000
    4bd
    3ba
    2,300 sqft
    133 Lake Shore Drive,
    Pleasantville, NY 10570
    Listing by: Compass Greater NY, LLC
  • 45 Great Oak Lane, Pleasantville, NY 10570
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    $1,190,000
    Studio
    2,902 sqft
    45 Great Oak Lane,
    Pleasantville, NY 10570
    Listing by: Real Broker NY LLC
  • 63 Ridgewood Drive, Pleasantville, NY 10570
    $325,000
    63 Ridgewood Drive,
    Pleasantville, NY 10570
    Listing by: Patricia Forgione's Realty
  • Lakeshore Drive Lot 14, Pleasantville, NY 10570
    $290,000
    Lakeshore Drive Lot 14,
    Pleasantville, NY 10570
    Listing by: Coldwell Banker Realty

Homes Near Pleasantville, NY

We found 30 more homes matching your filters just outside Pleasantville

  • 517A Old Chappaqua Road, Briarcliff Manor, NY 10510
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    NEW - 5 HRS AGO0.96 ACRES
    $1,999,222
    4bd
    4ba
    4,050 sqft (on 0.96 acres)
    517A Old Chappaqua Road,
    Briarcliff Manor, NY 10510
    Listing by: Howard Hanna Rand Realty
  • 11 Boulder Trail, Chappaqua, NY 10514
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    NEW - 1 DAY AGO0.93 ACRES
    $2,499,000
    5bd
    5ba
    6,495 sqft (on 0.93 acres)
    11 Boulder Trail,
    Chappaqua, NY 10514
    Listing by: Compass Greater NY, LLC
  • 153 Fairfax Avenue, Hawthorne, NY 10532
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    NEWOPEN SAT, 11-3PMCOMING SOON 4/26
    $750,000
    3bd
    2ba
    1,600 sqft
    153 Fairfax Avenue,
    Hawthorne, NY 10532
    Listing by: Compass Greater NY, LLC
  • 206 River Road, Briarcliff Manor, NY 10510
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    NEWCOMING SOON 5/60.9 ACRES
    $2,890,000
    5bd
    4ba
    3,753 sqft (on 0.90 acres)
    206 River Road,
    Briarcliff Manor, NY 10510
    Listing by: Julia B Fee Sothebys Int. Rlty
  • 127 S Highland Avenue UNIT 2A4, Ossining, NY 10562
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    NEW - 2 DAYS AGO
    $140,000
    1bd
    1ba
    750 sqft
    127 S Highland Avenue UNIT 2A4,
    Ossining, NY 10562
    Listing by: Douglas Elliman Real Estate
  • 38 Brookwood Drive, Briarcliff Manor, NY 10510
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    NEWOPEN SAT, 1-3PM1.13 ACRES
    $1,475,000
    4bd
    4ba
    3,990 sqft (on 1.13 acres)
    38 Brookwood Drive,
    Briarcliff Manor, NY 10510
    Listing by: Christie's Int. Real Estate
  • 33 Matthes Road, Briarcliff Manor, NY 10510
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    OPEN SUN, 12-3PM0.3 ACRES
    $799,000
    3bd
    2ba
    1,304 sqft (on 0.30 acres)
    33 Matthes Road,
    Briarcliff Manor, NY 10510
    Listing by: Moda Realty LLC
  • 121 New Broadway, Sleepy Hollow, NY 10591
    OPEN SAT, 12-2PM
    $649,000
    3bd
    2ba
    1,392 sqft
    121 New Broadway,
    Sleepy Hollow, NY 10591
    Listing by: Corcoran Legends Realty
  • 26 Spring Street, Hawthorne, NY 10532
    OPEN SUN, 12-3PMCOMING SOON 4/28
    $999,000
    4bd
    3ba
    2,300 sqft
    26 Spring Street,
    Hawthorne, NY 10532
    Listing by: Howard Hanna Rand Realty
  • 19 Madison Avenue, Ossining, NY 10562
    $489,000
    2bd
    2ba
    1,504 sqft
    19 Madison Avenue,
    Ossining, NY 10562
    Listing by: Houlihan Lawrence Inc.
  • 24 Studio Hill Road, Briarcliff Manor, NY 10510
    0.98 ACRES
    $958,000
    4bd
    3ba
    2,832 sqft (on 0.98 acres)
    24 Studio Hill Road,
    Briarcliff Manor, NY 10510
    Listing by: Berkshire Hathaway HS NY Prop
  • 2 Attitash Street, Chappaqua, NY 10514
    COMING SOON 4/262 ACRES
    $1,349,000
    4bd
    4ba
    3,497 sqft (on 2 acres)
    2 Attitash Street,
    Chappaqua, NY 10514
    Listing by: Compass Greater NY, LLC
  • 40 Linden Circle, Briarcliff Manor, NY 10510
    0.8 ACRES
    $1,650,000
    5bd
    5ba
    4,856 sqft (on 0.80 acres)
    40 Linden Circle,
    Briarcliff Manor, NY 10510
    Listing by: Guard Hill Realty
  • 152 Mill River Road, Chappaqua, NY 10514
    0.37 ACRES
    $799,000
    3bd
    2ba
    2,079 sqft (on 0.37 acres)
    152 Mill River Road,
    Chappaqua, NY 10514
    Listing by: Compass Greater NY, LLC
  • 134 Bainbridge Avenue, Thornwood, NY 10594
    $539,000
    2bd
    2ba
    1,306 sqft
    134 Bainbridge Avenue,
    Thornwood, NY 10594
    Listing by: Howard Hanna Rand Realty
  • 463 Chappaqua Road, Briarcliff, NY 10510
    1.07 ACRES
    $899,000
    3bd
    2ba
    2,677 sqft (on 1.07 acres)
    463 Chappaqua Road,
    Briarcliff, NY 10510
    Listing by: Houlihan Lawrence Inc.
  • 11 Laurel Lane, Chappaqua, NY 10514
    1.96 ACRES
    $1,950,000
    5bd
    3ba
    5,121 sqft (on 1.96 acres)
    11 Laurel Lane,
    Chappaqua, NY 10514
    Listing by: Houlihan Lawrence Inc.
  • 5 Harwood Avenue, Sleepy Hollow, NY 10591
    OPEN SAT, 12-2PM0.33 ACRES
    $1,250,000
    4bd
    3ba
    1,812 sqft (on 0.33 acres)
    5 Harwood Avenue,
    Sleepy Hollow, NY 10591
    Listing by: eXp Realty
  • 9 Peck Place, Chappaqua, NY 10514
    COMING SOON 4/251.01 ACRES
    $1,699,000
    4bd
    4ba
    3,884 sqft (on 1.01 acres)
    9 Peck Place,
    Chappaqua, NY 10514
    Listing by: William Raveis-New York, LLC
  • 7 Laurel Hill Place, Armonk, NY 10504
    1 ACRE
    $912,000
    3bd
    3ba
    2,210 sqft (on 1 acre)
    7 Laurel Hill Place,
    Armonk, NY 10504
    Listing by: Compass Greater NY, LLC
  • 73 Spring Street UNIT 4R, Ossining, NY 10562
    $495,000
    2bd
    2ba
    1,514 sqft
    73 Spring Street UNIT 4R,
    Ossining, NY 10562
    Listing by: Keller Williams Realty Group
  • 465 Chappaqua Road, Briarcliff Manor, NY 10510
    1.61 ACRES
    $1,075,000
    5bd
    3ba
    3,296 sqft (on 1.61 acres)
    465 Chappaqua Road,
    Briarcliff Manor, NY 10510
    Listing by: Compass Greater NY, LLC
  • 75 Eton Road, Thornwood, NY 10594
    2.44 ACRES
    $989,000
    3bd
    2ba
    1,732 sqft (on 2.44 acres)
    75 Eton Road,
    Thornwood, NY 10594
    Listing by: United Real Estate LLC
  • 290 Central Drive, Briarcliff Manor, NY 10510
    3.52 ACRES
    $2,760,000
    6bd
    7ba
    6,958 sqft (on 3.52 acres)
    290 Central Drive,
    Briarcliff Manor, NY 10510
    Listing by: Julia B Fee Sothebys Int. Rlty
  • 129-5 S Highland Avenue UNIT B2, Ossining, NY 10562
    $199,000
    2bd
    1ba
    950 sqft
    129-5 S Highland Avenue UNIT B2,
    Ossining, NY 10562
    Listing by: Howard Hanna Rand Realty
  • 121 S Highland Avenue UNIT 2C, Ossining, NY 10562
    $149,000
    1bd
    1ba
    750 sqft
    121 S Highland Avenue UNIT 2C,
    Ossining, NY 10562
    Listing by: Coldwell Banker Realty
  • 71 Tripp Street, Mount Kisco, NY 10549
    2.02 ACRES
    $1,295,000
    4bd
    3ba
    3,614 sqft (on 2.02 acres)
    71 Tripp Street,
    Mount Kisco, NY 10549
    Listing by: Houlihan Lawrence Inc.
  • 121 S Highland Avenue UNIT 3L, Ossining, NY 10562
    $174,900
    2bd
    1ba
    900 sqft
    121 S Highland Avenue UNIT 3L,
    Ossining, NY 10562
    Listing by: eXp Realty
  • 44 & 50 Bischoff Avenue, Chappaqua, NY 10514
    0.38 ACRES
    $799,000
    5bd
    2ba
    2,241 sqft (on 0.38 acres)
    44 & 50 Bischoff Avenue,
    Chappaqua, NY 10514
    Listing by: Compass Greater NY, LLC
  • 86 Bainbridge Avenue, Thornwood, NY 10594
    0.25 ACRES
    $575,000
    3bd
    3ba
    1,626 sqft (on 0.25 acres)
    86 Bainbridge Avenue,
    Thornwood, NY 10594
    Listing by: Berkshire Hathaway HS NY Prop

Pleasantville, NY Real Estate Trends

Learn about the Pleasantville, NY housing market through trends and averages.

Affordability of Living in Pleasantville, NY

The median home value is $882,091
MonthMedian home value
April 2023$820k
May 2023$824k
June 2023$828k
July 2023$832k
August 2023$840k
September 2023$849k
October 2023$857k
November 2023$861k
December 2023$864k
January 2024$865k
February 2024$872k
March 2024$882k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Pleasantville, NY, by Home Size

Currently, there are 1 new listing and 9 homes for sale in Pleasantville.
Home SizeHome Value*
3 bedrooms (See homes)$838,525
4 bedrooms (4 homes)$1,076,098
*Home value over the past month

What Locals Say about Pleasantville

  • Elizabeth Snees
    "It’s a great area. Security for the kids. Nice environment I have been lived over here for many years. I am really happy "
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  • Jeff
    "Amazing place to live. It is safe and the schools are great. Lots of good restaurants and the people are very friendly. "
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  • Katherinevonjan
    "Fireman’s parade, Pleasantville Day, Farmers Market, Pleasantville Music Festival, Revolutionary War Day"
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  • Greg
    "parade,farmers market, town pool,town tennis courts.......good schools and restaurants and ball fields "
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  • Joseescobrada
    "Safety and how people treat not only each other but the place where they live. Cleanliness. Local foods and local businesses "
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  • Katherinevonjan
    "Halloween, Fireman’s Parade, Jacob Burns Film Theater events, Farmers Market, Pleasantville Day, high school play, Pleasantville Music Festival..."
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  • Jami M.
    "We have the farmers market every Saturday, we have the Pleasantville music festival in the summer parades for the 4th of July"
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  • Ariel D.
    "This is a great area. I don’t personally commute but many people in this area will commute to New York City or White Plains "
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  • Joseph N
    "Great town for families. Good restaurants, shops, etc. greTvtown to walk in. Wonderful farmers market on Saturdays."
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  • Venizamarte
    "Nice busy area. Located very conveniently near metro north. Easy access to highways. "
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  • Carolynblankenship
    "Sidewalks are great for walking dogs. There’s a nice dog park as well. There are many dog owners in this town. "
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  • Halevale
    "People walk dogs of all shapes and sizes constantly. Seems a lovely dog community. Many restaurants also place water bowls outside during the warmer months. "
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  • Halevale
    "An incredible walkable village that lives up to its name. Amazing in all seasons, but has a great year round farmers market. Halloween is particularly awesome!"
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  • Ailun k.
    "People often seen walking dogs on sidewalk, fenced yards. Some children’s parks do not allow dogs, and the Farmer’s Market does not allow dogs. "
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  • Carolynblankenship
    "This is a walkable community commuting distance to Manhattan with excellent schools. There is a true sense of community here and people help each other. "
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  • Peter G.
    "I’ve lived here for 22 years and it’s a great place to raise kids, excellent school system, friendly, safe, with enough to do and a short train or car ride to Manhattan "
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