Pleasantville, NY Homes

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  /30

  $830,000 Pending

  • 4 Beds
  • 1 Bath
  • 1,890 Sq Ft

  414 Bear Ridge Rd, Pleasantville, NY 10570

  Charming Historic Colonial built in 1870 with original hardwood floors throughout and unique moldings that showcase artisanal craftsmanship from the mid-19th century. Every room has its own character, just waiting for you to fill it with your own touches and memories. Kitchen has been updated with plenty of storage. Large front porch with tons of privacy. Expansive newer windows throughout

  Stacy Weinberg Giner Real Estate Inc.

  414 Bear Ridge Rd, Pleasantville, NY 10570
• 

  $810,000 Sold Jul 23, 2025

  • 1,920 Sq Ft
  • $422/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  8 Douglas Dr, Pleasantville, NY 10570

  AO, 4/30, 1/2 Signed Contracts. From the moment you step into this impeccably maintained Raised Ranch you will feel at home. Home boasts gleaming hardwood flooring, bay window in living room, and newer windows throughout. Nestled at the end of a cul-de-sac, this home is bright and airy with an open concept living and dining area that streams natural light with vaulted ceilings. Expanded kitchen

  Jeanne Beckley Howard Hanna Rand Realty

  8 Douglas Dr, Pleasantville, NY 10570
• 

  Est $961,993 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,885 Sq Ft

  36 Lake Shore Dr, Pleasantville, NY 10570

  36 Lake Shore Dr, Pleasantville, NY 10570
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  /48

  $1,350,000 Pending

  • 2 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  5 Country Club Ln, Pleasantville, NY 10570

  Welcome to this beautifully designed END + CORNER UNIT townhome offering 2 spacious bedrooms, plus 2 extra rooms, with flexible options for guest rooms, additional bedrooms, or a home office. Perfectly situated just across from the Clubhouse, pool, restaurant, and pro shop, this home puts world-class amenities right at your doorstep. With two attached garages and a spacious open layout, comfort

  Marina Suh Keller Williams Realty Group

  5 Country Club Ln, Pleasantville, NY 10570
• 

  $925,000 Sold Jul 11, 2025

  • 2,438 Sq Ft
  • $379/SF
  • 27 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  1 Country Club Ln, Pleasantville, NY 10570

  Discover exceptional curb appeal with this stunning 4-bedroom colonial nestled in the highly sought-after Country Club neighborhood. Set on a professionally landscaped property, this home offers a fenced-in backyard for added privacy and outdoor enjoyment. Inviting bright sunlit home with an open kitchen that seamlessly flows into a spacious family room featuring vaulted ceilings, skylights, and

  Brendan Preston Houlihan Lawrence Inc.

  1 Country Club Ln, Pleasantville, NY 10570
• 

  Est $1,007,098 Not Listed For Sale

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

  40 Lake Shore Dr, Pleasantville, NY 10570

  40 Lake Shore Dr, Pleasantville, NY 10570
• 

  

  /19

  $245,000 Pending

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  70 Manville Rd Unit 1, Pleasantville, NY 10570

  Welcome to this beautifully updated first-floor 1-bedroom, 1-bathroom unit in the sought-after Ledgerock Gardens co-op community. Featuring a modern open floor plan with a seamless flow between living, dining, and kitchen areas, this home offers both comfort and style. Enjoy the convenience of being just a short distance from Pleasantville Village’s charming restaurants, shops, public library,

  Rita Longo Howard Hanna Rand Realty

  70 Manville Rd Unit 1, Pleasantville, NY 10570
• 

  $435,000 Sold Jul 11, 2025

  • 762 Sq Ft
  • $571/SF
  • 57 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1978

  76 Foxwood Dr Unit 4, Pleasantville, NY 10570

  Whether starting out or downsizing, this first-floor 1-bedroom, 1-bathroom condo offers comfortable living in a prime location. Featuring a spacious living room, a well-appointed kitchen, a dedicated dining area with a door leading to your own deck, storage and plenty of parking. Nestled in the desirable Foxwood Condominium complex with amenities including pool and adjacent tennis courts. Just a

  Rita Longo Howard Hanna Rand Realty

  76 Foxwood Dr Unit 4, Pleasantville, NY 10570
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  Est $1,018,280 Not Listed For Sale

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

  267 Mountain Rd, Pleasantville, NY 10570

  267 Mountain Rd, Pleasantville, NY 10570
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  /40

  $999,999 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft

  55 Deerfield Ln S, Pleasantville, NY 10570

  Welcome to 55 Deerfield Lane, Perfectly situated on nearly an acre of lush grounds in the coveted Byram Hills School District this beautifully maintained 4-bedroom, 2.5-bath home is bursting with natural light from large windows and gleaming hardwood floors throughout that create an inviting, warm atmosphere perfect for making lifelong memories.Start your day in the bright eat-in kitchen

  Tulay Erdem Christie's Int. Real Estate

  55 Deerfield Ln S, Pleasantville, NY 10570
• 

  $889,222 Sold Jul 11, 2025

  • 2,428 Sq Ft
  • $366/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  689 Washington Ave, Pleasantville, NY 10570

  Beautifully updated village charmer with all the bells and whistles! Hardwood floors, dual fireplace in living room, extensive dining room for large gatherings, eat in kitchen with stainless steel appliances, 4’ Sub Zero refrigerator, double convection oven, 4’ cook top with grill and griddle, cherry cabinetry with rollouts, under counter lighting, and granite counter tops. Custom built granite

  Mark Seiden Mark Seiden Real Estate Team

  689 Washington Ave, Pleasantville, NY 10570
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  Est $1,024,195 Not Listed For Sale

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

  22 Hillside Ave, Pleasantville, NY 10570

  22 Hillside Ave, Pleasantville, NY 10570
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  /37

  $1,525,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,620 Sq Ft

  9 Cy Ct, Pleasantville, NY 10570

  This fresh, young 4-bedroom Modern Colonial, in coveted Byram Hills school district, offers a private level yard and open living spaces on a charming cul de sac. In this bright and airy home, wide spacious rooms flow into one another, refinished light wood floors throughout and 9’ ceilings create a home that feels like new construction. The family room, with an elegant fireplace, opens into a

  Julie Schneider Compass Greater NY, LLC

  9 Cy Ct, Pleasantville, NY 10570
• 

  $1,475,000 Sold Jul 07, 2025

  • 3,144 Sq Ft
  • $469/SF
  • 59 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1920

  49 Walnut St, Pleasantville, NY 10570

  Welcome to 49 Walnut Street in the heart of Pleasantville! This spectacular home offers exceptional quality and thoughtful design, providing both space and comfort for modern living. Featuring six generously sized bedrooms, this beautifully manicured property offers ample space for comfortable living and entertaining, both inside and out.At the center of the home is an updated chef’s

  Christine Bamford Elegran LLC

  49 Walnut St, Pleasantville, NY 10570
• 

  Est $1,762,918 Not Listed For Sale

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

  66 Heritage Dr, Pleasantville, NY 10570

  66 Heritage Dr, Pleasantville, NY 10570
• 

  

  /28

  $715,000 Pending

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

  68 Foxwood Dr Unit 4, Pleasantville, NY 10570

  Welcome to this sought-after first-floor unit located in the highly desirable Foxwood Condo complex. This beautifully maintained unit offers 2 generous bedrooms and 2 full bathrooms, including a primary suite. The inviting living room features a door leading to a private balcony, perfect for relaxing. A separate dining room and an eat-in kitchen provide plenty of space for everyday living and

  Rita Longo Howard Hanna Rand Realty

  68 Foxwood Dr Unit 4, Pleasantville, NY 10570
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  $1,075,000 Sold Jul 01, 2025

  • 2,174 Sq Ft
  • $494/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1980

  8 Tumblebrook Ct, Pleasantville, NY 10570

  This Sprawling Ranch is located in a private Cul-De-Sac in Byram Hills School district. The open floor plan is perfect for entertaining. It features an updated kitchen with black granite counter tops, GE double oven, lots of cabinets and sliding glass doors leading to a patio. The den has Cathedral Ceilings and a wood burning fireplace which leads to an oversized gorgeous fenced backyard. The

  MARLENE STARR Signature Premier Properties

  8 Tumblebrook Ct, Pleasantville, NY 10570
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  Est $1,870,813 Not Listed For Sale

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

  3 Northview Ct, Pleasantville, NY 10570

  3 Northview Ct, Pleasantville, NY 10570
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  /19

  $510,000 Pending

  • 1 Bed
  • 1.5 Baths
  • 1,300 Sq Ft

  33 Roselle Ave Unit C, Pleasantville, NY 10570

  Downtown Living Meets Stylish Comfort in this move-in ready gem! An immaculate 1BR, 2BTH condo with a stunning blend of convenience and curated design - located just steps from the Metro North train, restaurants, shops, and all the vibrant energy of Pleasantville village life. So much to do, including weekly Farmer’s Market, annual Music Festival, and the world-renowned Jacob Burns Film Center.

  Maria Fitzgerald Compass Greater NY, LLC

  33 Roselle Ave Unit C, Pleasantville, NY 10570
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  $1,087,800 Sold Jul 01, 2025

  • 2,245 Sq Ft
  • $485/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1902

  44 Weskora Ave, Pleasantville, NY 10570

  Nestled in the highly sought-after Roselle Park neighborhood of Pleasantville, this delightful four-bedroom Colonial home offers a perfect blend of timeless charm and modern comfort. As you approach, the inviting covered rocking chair front porch welcomes you to a warm and cozy atmosphere. Inside, the home exudes character with spacious rooms and classic details, including a formal oversized

  Maura Mcspedon William Raveis Real Estate

  44 Weskora Ave, Pleasantville, NY 10570
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  Est $1,608,667 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  55 Heritage Dr, Pleasantville, NY 10570

  55 Heritage Dr, Pleasantville, NY 10570
• 

  

  /45

  $749,000 Pending

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

  5 Ridgeview Dr, Pleasantville, NY 10570

  Welcome to 5 Ridgeview Drive – where comfort, charm, and convenience meet. Set upon a quiet cul-de-sac and surrounded by lush greenery, this beautifully maintained ranch offers easy living in a serene setting. Step inside to discover timeless hardwood floors, an abundance of natural light, and a desirable open-concept layout that invites effortless everyday living and entertaining. The spacious

  Matthew Valvano Berkshire Hathaway HS NY Prop

  5 Ridgeview Dr, Pleasantville, NY 10570
• 

  $405,000 Sold Jun 26, 2025

  • 760 Sq Ft
  • $533/SF
  • 38 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1977

  56 Foxwood Dr Unit 5, Pleasantville, NY 10570

  A beautiful 1-bedroom unit awaits you if you are starting out or downsizing. Located in a prime location just a short distance from the village of Pleasantville- you will have access to shopping, dining, Jacob Burns Theater, and the train station to get to NYC. Unit includes brand new carpeting, brand new refrigerator, and combo washer and dryer in unit. Additional storage located in basement

  Leslie Ishoo Coldwell Banker Realty

  56 Foxwood Dr Unit 5, Pleasantville, NY 10570
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  Est $1,712,154 Not Listed For Sale

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

  67 Heritage Dr, Pleasantville, NY 10570

  67 Heritage Dr, Pleasantville, NY 10570
• 

  

  /19

  $1,375,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,544 Sq Ft

  15 Rockledge Rd, Pleasantville, NY 10570

  Welcome to 15 Rockledge Road. Perfectly sited on a quiet cul-de-sac just five minutes from Pleasantville, Chappaqua, and Armonk, this extraordinary home blends mid-century architecture with sophisticated modern updates, offering complete privacy without sacrificing convenience. Zoned for the coveted Byram Hills School District, this stunning property is as functional as it is design-forward.

  Carine Nowak Compass Greater NY, LLC

  15 Rockledge Rd, Pleasantville, NY 10570
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  $574,500 Sold Jun 24, 2025

  • 1,036 Sq Ft
  • $555/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  44 Foxwood Dr Unit 7, Pleasantville, NY 10570

  Welcome to this 2-bedroom, 1.5-bathroom condo located in the highly desirable Foxwood complex. This second-floor unit offers a well-designed layout featuring a full hall bathroom and a convenient half bath in the primary bedroom, which also includes a generous walk-in closet for added storage. The open dining and living area flows beautifully to a private balcony—perfect for enjoying your

  Rita Longo Howard Hanna Rand Realty

  44 Foxwood Dr Unit 7, Pleasantville, NY 10570
• 

  Est $1,193,838 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  4 Laurel Ln, Pleasantville, NY 10570

  4 Laurel Ln, Pleasantville, NY 10570
• 

  

  /13

  $450,000 Pending

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  16 Foxwood Dr Unit 6, Pleasantville, NY 10570

  Welcome to 16 Foxwood Drive, Unit 6, a beautifully renovated one-bedroom condo in the heart of Pleasantville. The home boasts handsome large windows, a thoughtfully-designed layout, and it is drenched in sunlight throughout the day. Step inside to discover a spacious, sunny living area perfect for relaxation or entertaining. The windowed eat-in kitchen features crisp countertops, modern

  Robyn Herman Compass Greater NY, LLC

  16 Foxwood Dr Unit 6, Pleasantville, NY 10570
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  $850,000 Sold Jun 20, 2025

  • 1,850 Sq Ft
  • $459/SF
  • 14 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2002

  12 Hillcrest Ave, Pleasantville, NY 10570

  You will wake up every morning to the tree top views of the Village of Pleasantville and beyond. The morning sun will reflect breathtaking panoramic views of everything this village has to offer! The western sky lights up with hypnotic shades of purple and orange above the deck. This special Townhouse offers the lifestyle you have been searching for...privacy, stunning views, the walkability

  Loretta Fleming Chiavetta Coldwell Banker Realty

  12 Hillcrest Ave, Pleasantville, NY 10570
• 

  Est $1,560,398 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,652 Sq Ft

  191 Deerfield Ln N, Pleasantville, NY 10570

  191 Deerfield Ln N, Pleasantville, NY 10570
• 

  

  /11

  $375,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,200 Sq Ft

  139 Bedford Rd, Pleasantville, NY 10570

  Rare opportunity to create your dream home in the heart of Pleasantville! Bring your contractors and a vision to this demolition project and enjoy all life has to offer just steps away from downtown Pleasantville dining, shopping and schools. Generously-sized private backyard boasts endless potential. Please note this is a short sale.

  Theresa Szuhany RE/MAX Ace Realty

  139 Bedford Rd, Pleasantville, NY 10570
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  $975,000 Sold Jun 20, 2025

  • 2,019 Sq Ft
  • $483/SF
  • 18 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1932

  24 Spring St, Pleasantville, NY 10570

  Welcome to Pleasantville! This delightful Village Colonial offers a perfect blend of comfort and convenience. With its inviting front porch and beautiful perennial gardens, and curb appeal from the moment you arrive. Inside, you will find bright, airy spaces with hardwood floors throughout and a seamless flow between rooms.The kitchen with ample storage and counter space, making meal prep a

  SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

  24 Spring St, Pleasantville, NY 10570
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  Est $1,036,288 Not Listed For Sale

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

  190 Lake Shore Dr, Pleasantville, NY 10570

  190 Lake Shore Dr, Pleasantville, NY 10570
• 

  $950,000 Sold Jun 19, 2025

  • 2,048 Sq Ft
  • $464/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  385 Lake Shore Dr, Pleasantville, NY 10570

  Welcome to your serene retreat at 385 Lake Shore Drive in Pleasantville.Tucked away on a quiet cul-de-sac in a peaceful neighborhood with a scenic all-seasons lake, this beautifully maintained 4-bedroom, 2-bathroom ranch, surrounded by woods, offers comfortable, one-level living in a stunning natural setting. The open-concept layout features a spacious eat-in kitchen, dining, and living area that

  Natalia Wixom Compass Greater NY, LLC

  385 Lake Shore Dr, Pleasantville, NY 10570
• 

  Est $1,022,423 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,480 Sq Ft

  174 Lake Shore Dr, Pleasantville, NY 10570

  174 Lake Shore Dr, Pleasantville, NY 10570
• 

  $900,000 Sold Jun 19, 2025

  • 1,618 Sq Ft
  • $556/SF
  • 15 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  353 Lake Shore Dr, Pleasantville, NY 10570

  Discover picturesque, all-season views living in this contemporary raised ranch home on a quiet cul-de-sac street. With high cathedral ceilings and large windows opening to a wraparound deck, the connection to nature is seamless, offering an ideal setting for relaxation, entertaining, and work.Enter just a few steps to the spacious open eat-in kitchen and living room with panoramic lake views.

  Natalia Wixom Compass Greater NY, LLC

  353 Lake Shore Dr, Pleasantville, NY 10570
• 

  Est $918,548 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,847 Sq Ft

  115 Woodland Rd, Pleasantville, NY 10570

  115 Woodland Rd, Pleasantville, NY 10570
• 

  $888,888 Sold Jun 19, 2025

  • 1,627 Sq Ft
  • $546/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1977

  24 Manville Ln Unit 4, Pleasantville, NY 10570

  Beautiful Foxwood Condominium.. Picturesque Country Setting with Meticulously Kept Grounds.. Absolutely Stunning Renovation of a Rarely Offered " Westminster " Model Townhome in a Great Location at the Highest Elevation in Foxwood.. Fabulous Kitchen with an Abundance of Cabinetry and Island Accommodating Stool Seating, Storage Built in's and Pantry, Quartzite Counters, Tile Backsplash, Stainless

  Vincent Vetrano Douglas Elliman Real Estate

  24 Manville Ln Unit 4, Pleasantville, NY 10570
• 

  Est $682,568 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,102 Sq Ft

  25 Woodland Rd, Pleasantville, NY 10570

  25 Woodland Rd, Pleasantville, NY 10570
• 

  $881,230 Sold Jun 19, 2025

  • 1,762 Sq Ft
  • $500/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  105 Lake St, Pleasantville, NY 10570

  A/O continue to showWelcome to CLUB 105 A Home Like No Other!Nestled in the heart of Pleasantville, "CLUB 105" is more than just a home, it's a lifestyle. This charming Cape-style residence at 105 Lake Street offers a covered front porch, oversized driveway, formal living and dining rooms, chef's kitchen with breakfast bar, four bedrooms, two full bathrooms, and a two-car garage, perfectly

  Clayton Livingston McGrath Realty Inc

  105 Lake St, Pleasantville, NY 10570

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