Pleasantville, NY Homes

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  /44

  $1,390,000

  Open Sat 12PM - 3PM Coming Soon

  • 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
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  /39

  $5,100 Per Month

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Apartment for Rent

  325 Manville Rd Unit 102, Pleasantville, NY 10570

  Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with six apartments. Each apartment features 2 Bedrooms/2 Bathrooms, Washer/Dryer in Unit, Radiant heated floors in primary bathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout the kitchen and baths,

  Imma Carletto Christie's Int. Real Estate

  325 Manville Rd Unit 102, Pleasantville, NY 10570
• 

  $1,225,000

  Sold May 14, 2026

  19 Club Ct, Pleasantville, NY 10570

  • 2 Beds
  • 3.5 Baths
  • 2,880 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Below List Price
  • $425/SF
  • 110 Days On Market

  Current Estimated Value $1,307,500

  Last Listing Agent Sena Baron William Raveis-New York, LLC

  19 Club Ct, Pleasantville, NY 10570
• 

  Est $395,840

  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
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  /42

  $1,325,000

  • 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
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  /10

  $3,500 Per Month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  155 Washington Ave, Pleasantville, NY 10570

  First floor of a charming village colonial. Updated bath. Huge eat in kitchen. Laundry area in basement with private washer and dryer. DRIVEWAY PARKING. VERY CLOSE TO TRAIN/TOWN/RESTAURANTS/JACOB BURNS FILM CENTER. Patio and Large back yard. Just a short distance from everything that Pleasantville has to offer. Storage area in basement. Owner pays for landscaping/heat/water, tenant pays electric

  Tom Consaga RE/MAX Ace Realty

  155 Washington Ave, Pleasantville, NY 10570
• 

  $1,080,000

  Sold Aug 25, 2025

  750 Bedford Rd, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft
  • Built 1968

  Last Sold Summary

  • 10% Below List Price
  • $379/SF
  • 58 Days On Market

  Current Estimated Value $1,107,176

  Last Listing Agent Cynthia Leite ERA Insite Realty Services

  750 Bedford Rd, Pleasantville, NY 10570
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  Est $2,369,134

  Not Listed For Sale

  4 Old Farm Rd S, Pleasantville, NY 10570

  • 4 Beds
  • 4.5 Baths
  • 5,298 Sq Ft
  • Built 2009

  4 Old Farm Rd S, Pleasantville, NY 10570

  Last Sold Summary

  • 4 Days On Market
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  /39

  $950,000

  $49K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  60 Pleasant Ave, Pleasantville, NY 10570

  Welcome to 60 Pleasant Avenue, a beautifully renovated home in the heart of Pleasantville. Thoughtfully updated in 2020, this property blends modern finishes with everyday functionality, offering a truly move-in ready experience. Inside, you’ll find updated systems, stylish design elements, and a smart, efficient layout that maximizes every inch of space. Designed with practical living in mind,

  Stephen Zondorak Astor Lane Realty

  60 Pleasant Ave, Pleasantville, NY 10570
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  $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 $1,288,350

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  61 Walnut St, Pleasantville, NY 10570
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  Est $1,197,071

  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
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  /24

  $959,000

  Open Sat 11AM - 1PM

  • 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
• 

  $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 $1,001,025

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  60 Cedar Ave, Pleasantville, NY 10570
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  Est $1,812,842

  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
• 

  

  /35

  $249,900

  Pending

  • 1 Bath
  • 500 Sq Ft

  580 Bedford Rd Unit 8, Pleasantville, NY 10570

  This rare studio condo is a small starter home or pied-a-terre with mighty potential -- and a deeded one-care garage -- ideally located in one of Westchester's most desirable villages. This 500sf unit with a private entrance has an open main space with an in-line kitchen, a spacious bathroom, and a surprising amount of closet space. Being sold for the first time in 40 years, the low asking price

  Allison Jaffe Key Real Estate Services, LLC

  580 Bedford Rd Unit 8, Pleasantville, NY 10570
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  $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
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  Est $1,526,748

  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
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  /22

  $600,000

  Pending

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

  17 Foxwood Dr Unit 5, Pleasantville, NY 10570

  Welcome to 17-5 Foxwood Drive, nestled in the highly desirable Foxwood community. This beautifully updated, sun-filled 1-bedroom with versatile den/office and 1.5 baths offers the perfect blend of space, comfort, and style, with thoughtful updates completed within the last six years.The expansive living and dining area is bright and inviting, offering generous room to entertain or unwind.

  Kathryn Weinberger Compass Greater NY, LLC

  17 Foxwood Dr Unit 5, Pleasantville, NY 10570
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  $975,000

  Sold Jun 20, 2025

  24 Spring St, Pleasantville, NY 10570

  • 4 Beds
  • 2.5 Baths
  • 2,019 Sq Ft
  • Built 1932

  Last Sold Summary

  • 15% Above List Price
  • $483/SF
  • 18 Days On Market

  Current Estimated Value $957,982

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

  24 Spring St, Pleasantville, NY 10570
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  Est $1,757,091

  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
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  /24

  $2,350,000

  • 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
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  $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 $799,727

  Last Listing Agent John Buoninfante Real Broker NY LLC

  9 Samson Dr, Pleasantville, NY 10570
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  Est $1,675,000

  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
• 

  

  /30

  $459,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  590 Bedford Rd Unit 2, Pleasantville, NY 10570

  Welcome to this bright and well-maintained 2-bedroom, 1-bath condo located in the desirable Greenwood Complex. Situated on the second floor, this home overlooks the beautifully landscaped courtyard with mature trees, shrubs, and lush lawns, creating a peaceful setting. The spacious living room features a large triple window that fills the space with natural light and brand-new wall-to-wall

  Patricia DelVecchio William Raveis Real Estate

  590 Bedford Rd Unit 2, Pleasantville, NY 10570
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  $1,350,000

  Sold Jun 03, 2025

  34 Sarles Ln, Pleasantville, NY 10570

  • 5 Beds
  • 2.5 Baths
  • 2,468 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Above List Price
  • $547/SF
  • 14 Days On Market

  Current Estimated Value $1,212,903

  Last Listing Agent Danielle Orellana William Raveis Real Estate

  34 Sarles Ln, Pleasantville, NY 10570
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  Est $1,312,667

  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
• 

  

  /39

  $899,000

  Open Sun 1PM - 3PM

  • 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
• 

  $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 $916,541

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  4 Rockledge Ln, Pleasantville, NY 10570
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  Est $1,771,667

  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
• 

  

  /35

  $1,025,000

  Coming Soon

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

  585 Bedford Rd, Pleasantville, NY 10570

  Welcome to Pleasantville! This beautifully maintained 3-bedroom, 2-bathroom home offers space, comfort, and exceptional value in a picturesque setting. Step into a light-filled living room featuring an oversized bay window that creates a warm and inviting atmosphere. The space flows seamlessly into a formal dining area, perfect for entertaining and everyday gatherings. Glass sliders open to a

  SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

  585 Bedford Rd, Pleasantville, NY 10570
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  $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 $673,803

  Last Listing Agent Anthony Sibio Coldwell Banker Realty

  16 Manville Ln Unit 4, Pleasantville, NY 10570
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  Est $703,557

  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
• 

  

  /39

  $899,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  161 Washington Ave, Pleasantville, NY 10570

  Location, location, location! Welcome to the heart of Pleasantville, NY, where walkability, convenience, and lifestyle come together. Just steps from the Metro-North train, village shops, restaurants, schools, and the Jacob Burns Film Center, this versatile property offers an exceptional opportunity for both investors and those seeking a multi-generational living solution. This sun-filled home

  Justine Flanagan Houlihan Lawrence Inc.

  161 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 $1,375,398

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

  306 Mountain Rd, Pleasantville, NY 10570
• 

  Est $987,634

  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
• 

  

  /17

  $950,000

  • 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
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  $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 $990,871

  Last Listing Agent Angela Lanni Houlihan Lawrence Inc.

  76 Sarles Ln, Pleasantville, NY 10570
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  Est $988,148

  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
• 

  

  /17

  $445,000

  $65K PRICE DROP

  • 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
• 

  $1,087,000

  Sold Jun 10, 2025

  3 Court St, Pleasantville, NY 10570

  • 3 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Above List Price
  • $418/SF
  • 15 Days On Market

  Current Estimated Value $1,108,451

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty

  3 Court St, Pleasantville, NY 10570

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