Pleasantville, NY Homes

• 

  

  

  /49

  $1,495,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,955 Sq Ft

  280 Bedford Rd, Pleasantville, NY 10570

  Stunning four-bedroom Village Victorian in the heart of Pleasantville, rich with late 1800s character and timeless architectural detail. This exceptional home showcases exquisite original features including ornate crown molding, soaring 10-foot ceilings, bay windows, hardwood floors, and a beautifully crafted wood banister spanning all three levels. The first floor offers a gracious and welcoming

  Maura Mcspedon William Raveis Real Estate

  280 Bedford Rd, Pleasantville, NY 10570
• 

  

  

  /3

  $1,950 Per Month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Apartment for Rent

  474 Bedford Rd Unit 1, Pleasantville, NY 10570

  Fantastic 1 bedroom 1 bath apartment in historic downtown building in Pleasantville. 1 Block to the train station, close to shops and restaurants. Granite counters, Crown Moulding, stainless appliances, hardwood floors and lots of light. Great apartment right in the middle of the Village.

  Steven Vescio Eastern Oaks Realty, LLC

  474 Bedford Rd Unit 1, Pleasantville, NY 10570
• 

  $1,285,000

  Sold Nov 12, 2025

  61 Walnut St, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,858 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $450/SF
  • 22 Days On Market

  Current Estimated Value $1,315,333

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  61 Walnut St, Pleasantville, NY 10570
• 

  Est $1,279,333

  Not Listed For Sale

  20 Brook Manor, Pleasantville, NY 10570

  • 5 Beds
  • 2 Baths
  • 2,570 Sq Ft
  • Built 1938

  20 Brook Manor, Pleasantville, NY 10570

  Last Sold Summary

  • 8 Days On Market
• 

  

  

  /27

  $850,000

  Pending

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

  37 Orchard St, Pleasantville, NY 10570

  Welcome home to 37 Orchard Street, a timeless Colonial nestled in the heart of the Village of Pleasantville. Ideally located just steps from everything this beloved community has to offer, you'll enjoy award-winning schools, the acclaimed Jacob Burns Film Center, the Pleasantville Farmers Market, charming shops, restaurants, cafes, and the Metro-North train station. Built in 1910, this special

  Maura Mcspedon William Raveis Real Estate

  37 Orchard St, Pleasantville, NY 10570
• 

  

  /11

  $2,950 Per Month

  • 1 Bed
  • 1 Bath
  • 1,400 Sq Ft
  • Apartment for Rent

  132 Woodland Dr, Pleasantville, NY 10570

  Discover the charm of 132 Woodland Drive, an excellent value for a rental in Pleasantville. All utilities, heat, electricity, water, sewer, and trash are included in the rent. This large one-bedroom legal accessory apartment on the lower level of a single-family home provides a unique living experience. Your private step-down entrance welcomes you to a sunlit eat-in kitchen equipped with

  Hiralben Trivedi Compass Greater NY, LLC

  132 Woodland Dr, Pleasantville, NY 10570
• 

  $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 $1,021,113

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  60 Cedar Ave, Pleasantville, NY 10570
• 

  Est $1,875,085

  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
• 

  

  /24

  $919,000

  $40K PRICE DROP Pending

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

  33 Brookside Place, Pleasantville, NY 10570

  Beautifully maintained 3-bedroom, 2 full bath raised ranch offering an open and airy floor plan, perfectly situated on a quiet cul-de-sac in a highly desirable location. This inviting home features spacious living areas filled with natural light, ideal for both everyday living and entertaining. Enjoy the convenience of being within walking distance to both the charming villages of Chappaqua and

  Sharon Foley ERA Insite Realty Services

  33 Brookside Place, 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 $1,558,143

  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
• 

  

  /30

  $1,499,000

  Pending

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

  3 Banks Hill Rd, Pleasantville, NY 10570

  Set on over an acre of private, bucolic property, this spacious mid-century modern inspired home offers the perfect blend of stylish design and warm, inviting living spaces. Soaring ceilings, natural materials, and an open floor plan create an airy, light-filled atmosphere. Thoughtfully updated throughout, the home features a renovated kitchen and updated bathrooms, along with four bedrooms and

  Amy Singer Houlihan Lawrence Inc.

  3 Banks Hill Rd, Pleasantville, NY 10570
• 

  $773,000

  Sold Aug 13, 2025

  9 Samson Dr, Pleasantville, NY 10570

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1980

  Last Sold Summary

  • $386/SF
  • 20 Days On Market

  Current Estimated Value $826,112

  Last Listing Agent John Buoninfante Real Broker NY LLC

  9 Samson Dr, Pleasantville, NY 10570
• 

  Est $1,828,000

  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
• 

  

  /35

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,891 Sq Ft

  4 Depew St, Pleasantville, NY 10570

  ATTEENTION WORK-AT -HOME PROFESSIONALS AND THOSE SEEKING MOTHER DAUGHTER SET UP! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to

  Al Posillico Keller Williams Realty Group

  4 Depew St, 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 $1,027,250

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  4 Rockledge Ln, Pleasantville, NY 10570
• 

  Est $1,577,667

  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
• 

  

  /43

  $869,999

  Pending

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

  28 Summit Place, Pleasantville, NY 10570

  Lovely modern Ranch on a cul-de-sac that offers 3+ bedrooms and 3 baths. A covered screened in back deck, where you can view nature and beautiful surroundings, with plenty of privacy. The first floor has very good circular motion, with open access to the living room, kitchen and dining room. Square footage does not include the lower level. With easy living on the main level and fabulous space on

  Kandy Kelly Collins Howard Hanna Rand Realty

  28 Summit Place, 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 $668,215

  Last Listing Agent Anthony Sibio Coldwell Banker Realty

  16 Manville Ln Unit 4, Pleasantville, NY 10570
• 

  Est $1,277,667

  Not Listed For Sale

  311 Bear Ridge Rd, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,936 Sq Ft
  • Built 1968

  311 Bear Ridge Rd, Pleasantville, NY 10570

  Last Sold Summary

  • 28 Days On Market
• 

  

  /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
• 

  $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 $1,413,000

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

  306 Mountain Rd, Pleasantville, NY 10570
• 

  Est $1,757,667

  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
• 

  

  /44

  $1,395,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,727 Sq Ft

  14 Briarwood Ln, Pleasantville, NY 10570

  Welcome to a truly special and rare opportunity located within the Briarcliff school district with Mt. Pleasant taxes. Nestled on a picturesque cul-de-sac in a sought-after part of the district, this beautifully updated 4 BR, 2.5 bath colonial offers the perfect blend of timeless charm, thoughtful design, and exceptional outdoor living. Set on a stunning, professionally landscaped property, this

  Suzan Zeolla Houlihan Lawrence Inc.

  14 Briarwood Ln, 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 $1,133,280

  Last Listing Agent Angela Lanni Houlihan Lawrence Inc.

  76 Sarles Ln, Pleasantville, NY 10570
• 

  Est $705,153

  Not Listed For Sale

  105 Lake Shore Dr, Pleasantville, NY 10570

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1959

  105 Lake Shore Dr, Pleasantville, NY 10570

  Last Sold Summary

  • 65 Days On Market
• 

  

  /17

  $649,000

  • 2 Beds
  • 1.5 Baths
  • 1,035 Sq Ft

  16 Manville Ln Unit 2, Pleasantville, NY 10570

  Welcome to this beautifully updated, move-in-ready 2-bedroom, 1.5-bath first-floor condominium offering 1,035 square feet of comfortable, low-maintenance living in the highly sought-after Foxwood community. This thoughtfully maintained home combines modern finishes, convenience, and an exceptional location in the heart of Pleasantville.Inside, you'll find beautiful hardwood floors throughout,

  Laura Pizzuti Berkshire Hathaway HS NY Prop

  16 Manville Ln Unit 2, 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 $962,502

  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
• 

  

  /50

  $3,350,000

  • 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
• 

  $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 $1,347,736

  Last Listing Agent Maria Teresa Duguet Houlihan Lawrence Inc.

  57 Dennis Ln, Pleasantville, NY 10570
• 

  Est $1,068,509

  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
• 

  

  /24

  $2,100,000

  $250K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 7,722 Sq Ft

  235 Bear Ridge Rd, Pleasantville, NY 10570

  Welcome to this extraordinary estate, a gem dating back to the 1900s, situated on over an acre of picturesque land. This sunlit residence boasts 6 spacious bedrooms and 4 1/2 bathrooms, making it the perfect sanctuary for entertaining guests. Step inside to experience the remarkable craftsmanship that defines this home. With oversized rooms designed for both formal gatherings and casual moments,

  Stacey Sporn William Raveis Real Estate

  235 Bear Ridge Rd, Pleasantville, NY 10570
• 

  $1,875,000

  Sold Aug 01, 2025

  22 Clark St, Pleasantville, NY 10570

  • 8 Beds
  • 7 Baths
  • 4,983 Sq Ft
  • Built 1916

  Last Sold Summary

  • 6% Below List Price
  • $376/SF
  • 72 Days On Market

  Current Estimated Value $1,942,000

  Last Listing Agent Imma Carletto Serhant LLC

  22 Clark St, Pleasantville, NY 10570
• 

  Est $843,224

  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
• 

  

  /38

  $1,100,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  88 Ridgeview Dr, Pleasantville, NY 10570

  Welcome to 88 Ridgeview Road, a place where quiet mornings, effortless entertaining, and the charm of Pleasantville come together in perfect harmony. Tucked away at the end of a coveted cul-de-sac and set on over an acre of beautifully landscaped property, this exceptional Colonial offers the rare combination of privacy, space, and convenience in one of Westchester County's most sought-after

  Kile Boga-Ibric Houlihan Lawrence Inc.

  88 Ridgeview Dr, Pleasantville, NY 10570
• 

  $649,000

  Sold May 13, 2026

  64 Foxwood Dr Unit 8, Pleasantville, NY 10570

  • 2 Beds
  • 1.5 Baths
  • 1,117 Sq Ft
  • Built 1979

  Last Sold Summary

  • $581/SF
  • 22 Days On Market

  Current Estimated Value $642,487

  Last Listing Agent Tom Consaga RE/MAX Ace Realty

  64 Foxwood Dr Unit 8, Pleasantville, NY 10570
• 

  Est $947,782

  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
• 

  

  /44

  $1,050,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,814 Sq Ft

  46 Bacon Hill Rd, Pleasantville, NY 10570

  Set far back from the street on a quiet residential street, this home sits on .94 beautifully landscaped, irrigated acres with charming stone walls. It also backs onto Pocantico Lake County Park for additional privacy and a country feel. Yet so close to the Briarcliff, Pleasantville and Tarrytown Village centers. Pleasantville PO with Briarcliff schools, and both Town of Mount Pleasant and

  Susan Strawgate Code Houlihan Lawrence Inc.

  46 Bacon Hill Rd, Pleasantville, NY 10570
• 

  $1,815,000

  Sold Jan 30, 2026

  153 Deerfield Ln N, Pleasantville, NY 10570

  • 4 Beds
  • 3 Baths
  • 3,534 Sq Ft
  • Built 1957

  Last Sold Summary

  • 14% Above List Price
  • $514/SF
  • 16 Days On Market

  Current Estimated Value $1,313,735

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC

  153 Deerfield Ln N, Pleasantville, NY 10570

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