Pleasantville, NY Homes

• 

  

  

  /22

  $479,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  590 Bedford Rd Unit 1, Pleasantville, NY 10570

  Easy Living in the Heart of Pleasantville!Welcome to this beautiful two-bedroom, first-floor condo in the desirable Greenwood Condominiums, offering no steps and effortless one-level living.Freshly painted and filled with natural light, this spacious home features a welcoming living room, updated kitchen with stainless steel appliances, warm wood cabinetry and a convenient

  Maura Mcspedon William Raveis Real Estate

  590 Bedford Rd Unit 1, Pleasantville, NY 10570
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• 

  $999,000

  Sold Nov 17, 2025

  60 Cedar Ave, Pleasantville, NY 10570

  • 4 Beds
  • 4 Baths
  • 2,461 Sq Ft
  • Built 1927

  Last Sold Summary

  • 9% Below List Price
  • $406/SF
  • 65 Days On Market

  Current Estimated Value $1,029,660

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  60 Cedar Ave, Pleasantville, NY 10570
• 

  Est $468,620

  Not Listed For Sale

  33 Roselle Ave Unit L, Pleasantville, NY 10570

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft
  • Built 1983

  33 Roselle Ave Unit L, Pleasantville, NY 10570

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Peter Giner Giner Real Estate Inc.
• 

  

  

  /19

  $879,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,825 Sq Ft

  460 Washington Ave, Pleasantville, NY 10570

  There are homes that need a project list. This isn't one of them. An impeccably maintained split-level offering that rare opportunity to simply move in and start enjoying from day one. Every major improvement has already been completed, inviting you in with confidence. A stunningly redesigned kitchen, updated baths, central air, young roof and siding, and a brand new boiler and hot water heater

  Maria Fitzgerald Compass Greater NY, LLC

  460 Washington Ave, Pleasantville, NY 10570
• 

  $950,000

  Sold Sep 10, 2026

  37 Orchard St, Pleasantville, NY 10570

  • 3 Beds
  • 1.5 Baths
  • 1,568 Sq Ft
  • Built 1910

  Last Sold Summary

  • 12% Above List Price
  • $606/SF
  • 15 Days On Market

  Current Estimated Value $947,649

  Last Listing Agent Maura Mcspedon William Raveis Real Estate

  37 Orchard St, Pleasantville, NY 10570
• 

  Est $1,983,667

  Not Listed For Sale

  96 Deerfield Ln N, Pleasantville, NY 10570

  • 5 Beds
  • 8 Baths
  • 4,551 Sq Ft
  • Built 1981

  96 Deerfield Ln N, Pleasantville, NY 10570

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Grace LoBello William Raveis Real Estate
• 

  

  /39

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 3,866 Sq Ft

  29 Country Club Ln, Pleasantville, NY 10570

  Enjoy this beautifully updated, and stylishly appointed, corner unit home in the highly desirable Pleasantville Country Club community. You will appreciate the ease of a maintenance-free, resort-style living, where you can spend more time enjoying the wonderful amenities and less time worrying about upkeep. Offering three levels of spacious living, the home welcomes you with a dramatic two-story

  Maura Mcspedon William Raveis Real Estate

  29 Country Club Ln, Pleasantville, NY 10570
• 

  $485,000

  Sold Dec 12, 2025

  590 Bedford Rd Unit 7, Pleasantville, NY 10570

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Above List Price
  • $539/SF
  • 27 Days On Market

  Last Listing Agent Felicia Marquie Houlihan Lawrence Inc.

  590 Bedford Rd Unit 7, Pleasantville, NY 10570
• 

  Est $1,685,333

  Not Listed For Sale

  23 Heritage Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,853 Sq Ft
  • Built 1981

  23 Heritage Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Stacy Levey William Raveis-New York, LLC
• 

  

  /31

  $475,000

  Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  590 Bedford Rd Unit 3, Pleasantville, NY 10570

  Welcome home to effortless, low-maintenance living in the highly sought-after Greenwood Condominium complex. Located on the first floor with seamless, step-free access, this bright and inviting 2-bedroom home pairs mid-century charm with smart, modern updates. Inside, refinished hardwood floors and generous natural light frame serene views of the beautifully landscaped grounds. The thoughtful

  Susan Hawkins Julia B Fee Sothebys Int. Rlty

  590 Bedford Rd Unit 3, Pleasantville, NY 10570
• 

  $910,000

  Sold Aug 14, 2026

  33 Brookside Place, Pleasantville, NY 10570

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1964

  Last Sold Summary

  • 5% Below List Price
  • $535/SF
  • 43 Days On Market

  Current Estimated Value $921,109

  Last Listing Agent Sharon Foley ERA Insite Realty Services

  33 Brookside Place, Pleasantville, NY 10570
• 

  Est $2,179,000

  Not Listed For Sale

  117 Deerfield Ln N, Pleasantville, NY 10570

  • 4 Beds
  • 4.5 Baths
  • 4,707 Sq Ft
  • Built 1984

  117 Deerfield Ln N, Pleasantville, NY 10570

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Patti Howard Compass Greater NY, LLC
• 

  

  /50

  $3,350,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 7,388 Sq Ft

  15 Heritage Dr, Pleasantville, NY 10570

  Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of

  Imma Carletto Serhant LLC

  15 Heritage Dr, Pleasantville, NY 10570
• 

  $997,500

  Sold Apr 24, 2026

  4 Rockledge Ln, Pleasantville, NY 10570

  • 2 Beds
  • 3.5 Baths
  • 2,760 Sq Ft
  • Built 1994

  Last Sold Summary

  • 13% Below List Price
  • $361/SF
  • 155 Days On Market

  Current Estimated Value $1,039,691

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  4 Rockledge Ln, Pleasantville, NY 10570
• 

  Est $1,895,667

  Not Listed For Sale

  118 Deerfield Ln N, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 3,518 Sq Ft
  • Built 1983

  118 Deerfield Ln N, Pleasantville, NY 10570

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Stacey Sporn William Raveis Real Estate
• 

  

  /46

  $1,499,000

  Pending

  • 3 Beds
  • 3 Baths
  • 3,013 Sq Ft

  15 Deerfield Ln S, Pleasantville, NY 10570

  Enjoy the best of Westchester living with a Pleasantville address in the highly sought-after Byram Hills School District. Just minutes from the Pleasantville Farmers Market, Jacob Burns Film Center, downtown Armonk, Chappaqua shopping, dining, and Metro-North, this beautifully updated ranch offers the perfect blend of convenience, privacy, and one-level living.The open-concept floor plan

  Nancy Beard Houlihan Lawrence Inc.

  15 Deerfield Ln S, Pleasantville, NY 10570
• 

  $679,000

  Sold Nov 05, 2025

  16 Manville Ln Unit 4, Pleasantville, NY 10570

  • 1 Bed
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1979

  Last Sold Summary

  • 24% Above List Price
  • $643/SF
  • 12 Days On Market

  Current Estimated Value $672,658

  Last Listing Agent Anthony Sibio Coldwell Banker Realty

  16 Manville Ln Unit 4, Pleasantville, NY 10570
• 

  Est $1,725,000

  Not Listed For Sale

  114 Deerfield Ln N, Pleasantville, NY 10570

  • 4 Beds
  • 3.5 Baths
  • 3,374 Sq Ft
  • Built 1983

  114 Deerfield Ln N, Pleasantville, NY 10570

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Stacey Sporn William Raveis Real Estate
• 

  

  /35

  $1,500,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,663 Sq Ft

  37 Pheasant Run Rd, Pleasantville, NY 10570

  Welcome to 37 Pheasant Run Road, a sun-drenched sanctuary offering seamless indoor-outdoor living in Pleasantville’s premier Estates neighborhood. Set comfortably back from the road on a beautiful, private lot surrounded by lush gardens, this custom-crafted home features an open layout bathed in exceptional natural light. Designed for both dynamic entertaining and peaceful everyday living, the

  Jocelyn Cloder Compass Greater NY, LLC

  37 Pheasant Run Rd, Pleasantville, NY 10570
• 

  $1,400,000

  Sold Oct 24, 2025

  306 Mountain Rd, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 3,800 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $368/SF
  • 27 Days On Market

  Current Estimated Value $1,385,667

  Last Listing Agent SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

  306 Mountain Rd, Pleasantville, NY 10570
• 

  Est $1,846,667

  Not Listed For Sale

  245 Bear Ridge Rd, Pleasantville, NY 10570

  • 4 Beds
  • 4.5 Baths
  • 6,677 Sq Ft
  • Built 1992

  245 Bear Ridge Rd, Pleasantville, NY 10570

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Stacey Sporn William Raveis Real Estate
• 

  

  /17

  $950,000

  Pending

  • 7 Beds
  • 3 Baths

  33 Hopper St, Pleasantville, NY 10570

  Excellent investment or owner-occupant opportunity in the heart of Pleasantville! This well-maintained multi-family property features three apartments, including one 3-bedroom unit and two 2-bedroom units—ideal for generating steady rental income.Each unit offers 1 full bathroom, a functional layout, and great natural light throughout. The 2-bedroom apartments located on the second and third

  Andreia Cordeiro eXp Realty

  33 Hopper St, Pleasantville, NY 10570
• 

  $1,110,000

  Sold Dec 10, 2025

  76 Sarles Ln, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • Built 2010

  Last Sold Summary

  • $475/SF
  • 21 Days On Market

  Current Estimated Value $1,124,000

  Last Listing Agent Angela Lanni Houlihan Lawrence Inc.

  76 Sarles Ln, Pleasantville, NY 10570
• 

  Est $951,077

  Not Listed For Sale

  34 Lake Shore Dr, Pleasantville, NY 10570

  • 3 Beds
  • 3 Baths
  • 2,570 Sq Ft
  • Built 1971

  34 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Anthony Carpenito North Country Sothebys Int Rlt
• 

  

  /32

  $1,325,000

  $74K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  18 Brookview Dr, Pleasantville, NY 10570

  Enjoy carefree and resort-style living in the Pleasantville Country Club community! Perfectly situated as one of only ten homes at the end of a private cul-de-sac, this beautifully updated 3-bedroom, 3.5-bath townhome offers 3,434 square feet of elegant living space.The main level features a fabulous Kingswood gourmet kitchen, complete with a large granite center island, top-of-the-line

  Justine Flanagan Houlihan Lawrence Inc.

  18 Brookview Dr, Pleasantville, NY 10570
• 

  $2,000,000

  Sold Aug 11, 2026

  3 Banks Hill Rd, Pleasantville, NY 10570

  • 4 Beds
  • 3 Baths
  • 3,340 Sq Ft
  • Built 1986

  Last Sold Summary

  • 33% Above List Price
  • $599/SF
  • 7 Days On Market

  Current Estimated Value $1,482,989

  Last Listing Agent Amy Singer Houlihan Lawrence Inc.

  3 Banks Hill Rd, Pleasantville, NY 10570
• 

  Est $1,079,946

  Not Listed For Sale

  40 Lake Shore Dr, Pleasantville, NY 10570

  • 5 Beds
  • 2.5 Baths
  • 3,300 Sq Ft
  • Built 2006

  40 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 252 Days On Market

  Last Listing Agent Justin Pieragostini Coldwell Banker Realty
• 

  

  /16

  $435,000

  Pending

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  600 Bedford Rd Unit 9, Pleasantville, NY 10570

  Rare opportunities like this are almost impossible to find in Pleasantville. Completely renovated from top to bottom and never lived in after the renovation, this mint-condition Greenwood Condominium offers true turnkey living in one of Westchester's most walkable communities. Every inch of the home has been thoughtfully updated, including brand-new flooring throughout, a stunning new kitchen

  Matthew Gluck Nestedge Realty

  600 Bedford Rd Unit 9, Pleasantville, NY 10570
• 

  $185,000

  Sold Aug 03, 2026

  300 Manville Rd Unit C22, Pleasantville, NY 10570

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Built 1948

  Last Sold Summary

  • $308/SF
  • 35 Days On Market

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  300 Manville Rd Unit C22, Pleasantville, NY 10570
• 

  Est $864,582

  Not Listed For Sale

  90 Lake Shore Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1963

  90 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Maura Mcspedon William Raveis Real Estate
• 

  

  /34

  $1,200,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  1 Woodland Dr, Pleasantville, NY 10570

  Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living.Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living

  Loretta Fleming Chiavetta Coldwell Banker Realty

  1 Woodland Dr, Pleasantville, NY 10570
• 

  $215,000

  Sold Jun 09, 2026

  580 Bedford Rd Unit 8, Pleasantville, NY 10570

  • 1 Bath
  • 500 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Below List Price
  • $430/SF
  • 36 Days On Market

  Last Listing Agent Allison Jaffe Key Real Estate Services, LLC

  580 Bedford Rd Unit 8, Pleasantville, NY 10570
• 

  Est $965,714

  Not Listed For Sale

  385 Lake Shore Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft
  • Built 1960

  385 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
• 

  

  /31

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,329 Sq Ft

  582 Washington Ave, Pleasantville, NY 10570

  First time on the market in over 50 years—an exciting opportunity to create something truly your own in an exceptional location! Ideally situated between the vibrant Villages of Pleasantville and Chappaqua, this split-level home offers a wonderful canvas for its next owner to renovate, reimagine, and make their own. Inside, hardwood floors and abundant natural light set the stage for a fresh

  Karin Morano Corcoran Legends Realty

  582 Washington Ave, Pleasantville, NY 10570
• 

  $1,375,000

  Sold Jun 08, 2026

  57 Dennis Ln, Pleasantville, NY 10570

  • 3 Beds
  • 2.5 Baths
  • 3,228 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Above List Price
  • $426/SF
  • 19 Days On Market

  Current Estimated Value $1,374,430

  Last Listing Agent Maria Teresa Duguet Houlihan Lawrence Inc.

  57 Dennis Ln, Pleasantville, NY 10570
• 

  Est $881,438

  Not Listed For Sale

  260 Sarles Ln, Pleasantville, NY 10570

  • 5 Beds
  • 2 Baths
  • 2,616 Sq Ft
  • Built 1964

  260 Sarles Ln, Pleasantville, NY 10570

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
• 

  

  /27

  $724,900

  • 4 Beds
  • 1 Bath
  • 1,626 Sq Ft

  45 Leroy St, Pleasantville, NY 10570

  Nestled in the midst of an idyllic, tree-filled, half-acre setting, this charming, character-filled gem is ideal for working from home, relaxing and entertaining!Upon entry, the foyer opens to a formal living room with several architectural features of note -- a beautiful arched, vaulted ceiling, hardwood floors and a fireplace withstone trim. At the opposite end of the room is a huge

  Pamela Jones Coldwell Banker Realty

  45 Leroy St, Pleasantville, NY 10570
• 

  $1,147,080

  Sold Aug 21, 2026

  28 Summit Place, Pleasantville, NY 10570

  • 3 Beds
  • 3 Baths
  • 1,869 Sq Ft
  • Built 1958

  Last Sold Summary

  • 32% Above List Price
  • $614/SF
  • 15 Days On Market

  Current Estimated Value $875,955

  Last Listing Agent Kandy Kelly Collins Howard Hanna Rand Realty

  28 Summit Place, Pleasantville, NY 10570
• 

  Est $1,140,188

  Not Listed For Sale

  267 Mountain Rd, Pleasantville, NY 10570

  • 4 Beds
  • 3 Baths
  • 3,112 Sq Ft
  • Built 1985

  267 Mountain Rd, Pleasantville, NY 10570

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Marcia Minassian Houlihan Lawrence Inc.
• 

  

  /49

  $2,499,999

  Open Sat 1PM - 3PM Coming Soon

  • 5 Beds
  • 5 Baths
  • 5,055 Sq Ft

  26 Cecilia Ln, Pleasantville, NY 10570

  Experience modern luxury at 26 Cecilia Lane, a completely move-in-ready, 5,055-square-foot contemporary ranch that pairs impressive scale with the effortless ease of predominantly first floor living. Flooded with natural light and set on more than 1.5 acres of professionally landscaped, flat and usable grounds, this exceptional residence offers 5 bedrooms, 3 full bathrooms, two powder rooms and

  Leslie Shemin-Lester Julia B Fee Sothebys Int. Rlty

  26 Cecilia Ln, Pleasantville, NY 10570

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