Pleasantville, NY Homes

• 

  Est $827,690

  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
• 

  

  

  /46

  $1,499,000

  • 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
• 

  $1,400,000

  Sold Aug 26, 2025

  17 Country Club Ln, Pleasantville, NY 10570

  • 3 Beds
  • 3.5 Baths
  • 3,434 Sq Ft
  • Built 1996

  Last Sold Summary

  • 9% Above List Price
  • $408/SF
  • 23 Days On Market

  Current Estimated Value $1,418,916

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  17 Country Club Ln, Pleasantville, NY 10570
• 

  Est $1,056,848

  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
• 

  

  

  /39

  $899,000

  Pending

  • 5 Beds
  • 1.5 Baths
  • 2,123 Sq Ft

  294 Bedford Rd, Pleasantville, NY 10570

  Welcome to 294 Bedford Road - this enchanting antique home, built in 1902, is nestled in the heart of Pleasantville. With a prime in-town location just half a mile from the train station, you’ll enjoy the perfect blend of historic charm and modern convenience. This 5-bedroom gem boasts a classic front porch that invites you to sit back and relax while sipping your morning coffee. The spacious

  Cyndi David William Raveis-New York, LLC

  294 Bedford Rd, Pleasantville, NY 10570
• 

  $960,555

  Sold Dec 16, 2025

  159 Sarles Ln, Pleasantville, NY 10570

  • 2 Beds
  • 2.5 Baths
  • 2,018 Sq Ft
  • Built 1905

  Last Sold Summary

  • 20% Above List Price
  • $476/SF
  • 14 Days On Market

  Current Estimated Value $926,581

  Last Listing Agent Vanessa Catalano Julia B Fee Sothebys Int. Rlty

  159 Sarles Ln, Pleasantville, NY 10570
• 

  Est $1,072,407

  Not Listed For Sale

  22 Hillside Ave, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,208 Sq Ft
  • Built 1971

  22 Hillside Ave, Pleasantville, NY 10570

  Last Sold Summary

  • 14 Days On Market
• 

  

  /34

  $745,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft

  61 Ridgewood Dr, Pleasantville, NY 10570

  Welcome to 61 Ridgewood Drive, a beautifully maintained 3-bedroom, 2 bath home nestled on a picturesque tree-lined street in the heart of Pleasantville. Filled with natural light and timeless appeal, this inviting residence offers warmth and charm from the moment you arrive. New windows throughout brighten every room, while high ceilings in the main living area add an airy feel and enhance the

  Wendy Holt Houlihan Lawrence Inc.

  61 Ridgewood Dr, Pleasantville, NY 10570
• 

  $1,351,000

  Sold Dec 02, 2025

  200 Central Ave, Pleasantville, NY 10570

  • 3 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 1991

  Last Sold Summary

  • 29% Above List Price
  • $549/SF
  • 22 Days On Market

  Current Estimated Value $1,295,155

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  200 Central Ave, Pleasantville, NY 10570
• 

  Est $867,490

  Not Listed For Sale

  12 Hillcrest Ave, Pleasantville, NY 10570

  • 2 Beds
  • 1.5 Baths
  • 1,850 Sq Ft
  • Built 2002

  12 Hillcrest Ave, Pleasantville, NY 10570

  Last Sold Summary

  • 14 Days On Market
• 

  

  /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
• 

  $780,000

  Sold Oct 23, 2025

  414 Bear Ridge Rd, Pleasantville, NY 10570

  • 4 Beds
  • 1 Bath
  • 1,890 Sq Ft
  • Built 1870

  Last Sold Summary

  • 10% Below List Price
  • $413/SF
  • 81 Days On Market

  Current Estimated Value $820,099

  Last Listing Agent Stacy Weinberg Giner Real Estate Inc.

  414 Bear Ridge Rd, Pleasantville, NY 10570
• 

  Est $1,602,333

  Not Listed For Sale

  184 Deerfield Ln N, Pleasantville, NY 10570

  • 5 Beds
  • 4.5 Baths
  • 3,491 Sq Ft
  • Built 1987

  184 Deerfield Ln N, Pleasantville, NY 10570

  Last Sold Summary

  • 8 Days On Market
• 

  

  /31

  $1,275,000

  $50K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,423 Sq Ft

  10 Grandview Ave, Pleasantville, NY 10570

  Looking to immerse yourself in the vibrant Pleasantville community? Don’t miss this rare opportunity to own a beautifully updated village home just steps from the award-winning Bedford Road Elementary School. This charming, light-filled residence offers 3 spacious bedrooms and 2.5 bathrooms, with thoughtful updates, abundant storage, and flexible living spaces throughout. The eat-in kitchen and

  Theresa Szuhany RE/MAX Ace Realty

  10 Grandview Ave, Pleasantville, NY 10570
• 

  $975,000

  Sold Aug 06, 2025

  22 Church St, Pleasantville, NY 10570

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1815

  Last Sold Summary

  • 3% Above List Price
  • $488/SF
  • 11 Days On Market

  Current Estimated Value $938,168

  Last Listing Agent Joseph Lukic Compass Greater NY, LLC

  22 Church St, Pleasantville, NY 10570
• 

  Est $1,780,000

  Not Listed For Sale

  66 Heritage Dr, Pleasantville, NY 10570

  • 5 Beds
  • 3.5 Baths
  • 5,160 Sq Ft
  • Built 1982

  66 Heritage Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 14 Days On Market
• 

  

  /32

  $1,399,000

  • 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
• 

  $1,425,000

  Sold Aug 08, 2025

  4 Watch Hill Rd, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 3,456 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Above List Price
  • $412/SF
  • 7 Days On Market

  Current Estimated Value $1,487,022

  Last Listing Agent Maura Mcspedon William Raveis Real Estate

  4 Watch Hill Rd, Pleasantville, NY 10570
• 

  Est $1,663,000

  Not Listed For Sale

  8 Northview Ct, Pleasantville, NY 10570

  • 4 Beds
  • 3.5 Baths
  • 3,692 Sq Ft
  • Built 1981

  8 Northview Ct, Pleasantville, NY 10570

  Last Sold Summary

  • 12 Days On Market
• 

  

  /44

  $1,390,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,334 Sq Ft

  20 Robbins Rd, Pleasantville, NY 10570

  Welcome to 20 Robbins Road—perfectly set on a quiet cul-de-sac on a half-acre with a fenced in backyard in one of Westchester’s most desirable communities. Step inside to an inviting living and dining area where oversized windows and a cathedral ceiling with skylight fill the space with natural light. A cut-stone fireplace, recessed lighting, and oak floors create a warm, stylish setting for

  Anthony Carpenito North Country Sothebys Int Rlt

  20 Robbins Rd, Pleasantville, NY 10570
• 

  $795,000

  Sold Oct 09, 2025

  68 Foxwood Dr Unit 4, Pleasantville, NY 10570

  • 2 Beds
  • 2 Baths
  • 1,273 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Above List Price
  • $625/SF
  • 22 Days On Market

  Current Estimated Value $783,884

  Last Listing Agent Rita Longo Howard Hanna Rand Realty

  68 Foxwood Dr Unit 4, Pleasantville, NY 10570
• 

  Est $1,887,000

  Not Listed For Sale

  3 Northview Ct, Pleasantville, NY 10570

  • 4 Beds
  • 4 Baths
  • 5,432 Sq Ft
  • Built 1981

  3 Northview Ct, Pleasantville, NY 10570

  Last Sold Summary

  • 33 Days On Market
• 

  

  /16

  $445,000

  $65K PRICE DROP Pending

  • 1 Bed
  • 1.5 Baths
  • 1,000 Sq Ft

  33 Roselle Ave Unit K, Pleasantville, NY 10570

  This is the one you've been waiting for! Welcome home to 33 Roselle Avenue Unit #K! This spacious, modern style condo home is complete with high ceilings, one bedroom and one and a half Bathroom and is just waiting for you to call it your own! Welcome as you enter and gaze upon your large picture window. With a large living room, complete with plenty of space you can even have an in home office.

  Michael Ciofalo Keller Williams NY Realty

  33 Roselle Ave Unit K, Pleasantville, NY 10570
• 

  $790,000

  Sold Sep 10, 2025

  5 Ridgeview Dr, Pleasantville, NY 10570

  • 3 Beds
  • 2 Baths
  • 1,605 Sq Ft
  • Built 1948

  Last Sold Summary

  • 5% Above List Price
  • $492/SF
  • 28 Days On Market

  Current Estimated Value $883,809

  Last Listing Agent Matthew Valvano Berkshire Hathaway HS NY Prop

  5 Ridgeview Dr, Pleasantville, NY 10570
• 

  Est $1,869,333

  Not Listed For Sale

  67 Heritage Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 4,896 Sq Ft
  • Built 1982

  67 Heritage Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 7 Days On Market
• 

  

  /23

  $1,850,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 4,121 Sq Ft

  25 Pheasant Run Rd, Pleasantville, NY 10570

  Welcome to this meticulously maintained Colonial home in the heart of Pleasantville, offering modern, youthful style and the warmth of a true community. The light-filled interior is move-in ready, with four generous bedrooms, three full baths, and a convenient powder room designed for everyday living and effortless entertaining. The fully finished lower level expands the home’s footprint with a

  Stacee Lieberman-Massoni Julia B Fee Sothebys Int. Rlty

  25 Pheasant Run Rd, Pleasantville, NY 10570
• 

  $2,005,000

  Sold Jun 15, 2026

  301 Bear Ridge Rd, Pleasantville, NY 10570

  • 5 Beds
  • 4 Baths
  • 4,321 Sq Ft
  • Built 1945

  Last Sold Summary

  • 20% Above List Price
  • $464/SF
  • 14 Days On Market

  Current Estimated Value $1,653,147

  Last Listing Agent Loretta Fleming Chiavetta Coldwell Banker Realty

  301 Bear Ridge Rd, Pleasantville, NY 10570
• 

  Est $1,069,927

  Not Listed For Sale

  190 Lake Shore Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft
  • Built 1960

  190 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 21 Days On Market
• 

  

  /22

  $999,000

  Pending

  • 1 Bed
  • 3 Baths
  • 2,011 Sq Ft

  47 Brookfield Place, Pleasantville, NY 10570

  Tucked away on one of Pleasantville Village’s most picturesque, tree lined streets, where the setting feels as though it has been lifted straight from the pages of a storybook, 47 Brookfield offers a truly rare and special opportunity. Perfectly positioned on a quiet cul de sac, this is the kind of place where children play freely, neighbors stroll by with a friendly wave, and life slows down

  Kile Boga-Ibric Houlihan Lawrence Inc.

  47 Brookfield Place, Pleasantville, NY 10570
• 

  $1,200,000

  Sold Mar 23, 2026

  300 Washington Ave, Pleasantville, NY 10570

  • 4 Beds
  • 4 Baths
  • 2,184 Sq Ft
  • Built 1947

  Last Sold Summary

  • 20% Above List Price
  • $549/SF
  • 7 Days On Market

  Current Estimated Value $1,154,914

  Last Listing Agent James Schunk Schunk Realty Group

  300 Washington Ave, Pleasantville, NY 10570
• 

  Est $1,000,847

  Not Listed For Sale

  99 Oak Ridge Rd, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,425 Sq Ft
  • Built 1954

  99 Oak Ridge Rd, Pleasantville, NY 10570

  Last Sold Summary

  • 16 Days On Market
• 

  

  /42

  $1,325,000

  Pending

  • 5 Beds
  • 4 Baths
  • 3,500 Sq Ft

  302 Washington Ave, Pleasantville, NY 10570

  Welcome to 302 Washington Avenue, a beautifully crafted 5-bedroom, 4-bathroom Colonial located in one of Pleasantville’s most sought-after neighborhoods. This newly constructed home combines timeless design with modern amenities, all within walking distance to Metro North, local shops, restaurants, and scenic parks—perfect for those seeking convenience without compromising on luxury.Step

  Cathy DeBow William Raveis Real Estate

  302 Washington Ave, Pleasantville, NY 10570
• 

  $605,000

  Sold Jun 24, 2026

  17 Foxwood Dr Unit 5, Pleasantville, NY 10570

  • 1 Bed
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $573/SF
  • 39 Days On Market

  Current Estimated Value $599,507

  Last Listing Agent Kathryn Weinberger Compass Greater NY, LLC

  17 Foxwood Dr Unit 5, Pleasantville, NY 10570
• 

  Est $649,756

  Not Listed For Sale

  14 Mountain Trail, Pleasantville, NY 10570

  • 2 Beds
  • 1 Bath
  • 942 Sq Ft
  • Built 1954

  14 Mountain Trail, Pleasantville, NY 10570

  Last Sold Summary

  • 13 Days On Market
• 

  

  /45

  $1,095,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  7 Hays Hill Rd, Pleasantville, NY 10570

  "HAYS HILL HAVEN" - Tucked at the end of a quiet cul-de-sac in the heart of one of Westchester's most beloved and vibrant villages, 7 Hays Hill Road is the kind of home that feels instantly comforting the moment you arrive. Framed by mature trees, thoughtful landscaping and glowing natural light throughout, this fully renovated striking Colonial offers a rare balance of timeless charm and modern

  Ryan Paige Corcoran Baer & McIntosh

  7 Hays Hill Rd, Pleasantville, NY 10570
• 

  $1,249,000

  Sold Mar 06, 2026

  133 Lake Shore Dr, Pleasantville, NY 10570

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $431/SF
  • 134 Days On Market

  Current Estimated Value $1,276,000

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC

  133 Lake Shore Dr, Pleasantville, NY 10570
• 

  Est $983,909

  Not Listed For Sale

  355 Lake Shore Dr, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,356 Sq Ft
  • Built 1984

  355 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 13 Days On Market
• 

  

  /22

  $265,000

  Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  53 Broadway Unit 1E, Pleasantville, NY 10570

  Welcome to Pleasant Manor, a charming cooperative community located just one block from Pleasantville’s Old Village, known for its boutique shops and restaurants. It’s also only a few blocks from schools, the library, train station, Jacob Burns Film Center, and the popular Farmers Market. This quiet first-level garden apartment features two bedrooms and one bathroom, with three exposures that

  Jerald Seti Coldwell Banker Realty

  53 Broadway Unit 1E, Pleasantville, NY 10570
• 

  $665,000

  Sold Apr 09, 2026

  4 Foxwood Dr Unit 5, Pleasantville, NY 10570

  • 2 Beds
  • 1.5 Baths
  • 1,117 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Above List Price
  • $595/SF
  • 14 Days On Market

  Current Estimated Value $663,576

  Last Listing Agent Jared Paletti Houlihan Lawrence Inc.

  4 Foxwood Dr Unit 5, Pleasantville, NY 10570
• 

  Est $892,902

  Not Listed For Sale

  353 Lake Shore Dr, Pleasantville, NY 10570

  • 3 Beds
  • 1.5 Baths
  • 1,618 Sq Ft
  • Built 1964

  353 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 15 Days On Market

Showing Results 81 - 120, Page 3 of 18