Pleasantville, NY Homes

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  /25

  $1,200,000 Pending

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

  4 Watch Hill Rd, Pleasantville, NY 10570

  Unlock the potential of this spacious 4-bedroom home, offering 3,500 sq ft of living space on nearly an acre of serene, private land. This is your opportunity to customize and create your dream home in the highly desirable Byram Hills School District. Enjoy endless possibilities with an in-ground pool, charming gazebo, and expansive yard—perfect for entertaining or relaxing in your own backyard

  Maura Mcspedon William Raveis Real Estate

  4 Watch Hill Rd, Pleasantville, NY 10570
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• 

  

  

  /20

  $6,300 per month

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

  39 Washington Ave Unit 304, Pleasantville, NY 10570

  Welcome to Washington Avenue Lofts, where luxury meets convenience. Our residences offer a variety of layouts, including studios, 1-bedroom, and 2-bedroom options. Each home is designed with premium finishes, featuring quartz countertops, custom cabinetry and closets, wood flooring, recessed lighting, GE stainless steel appliances, in-unit washer/dryer, and more. On-site amenities include a Latch

  John Oliveira Douglas Elliman Real Estate

  39 Washington Ave Unit 304, 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 $366,463 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  580 Bedford Rd Unit 16, Pleasantville, NY 10570

  580 Bedford Rd Unit 16, Pleasantville, NY 10570
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  /32

  $1,100,000 Pending

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

  750 Bedford Rd, Pleasantville, NY 10570

  Step into your private oasis in this enchanting 4-bedroom colonial, nestled in the award-winning Pleasantville school district! With its spacious living room featuring French doors to the patio and a cozy wood-burning fireplace, you’ll love the warmth and elegance this home exudes. The inviting dining room flows seamlessly into an eat-in kitchen, complete with doors that lead to a fantastic back

  Cynthia Leite ERA Insite Realty Services

  750 Bedford Rd, 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 $389,846 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft

  33 Roselle Ave Unit L, Pleasantville, NY 10570

  33 Roselle Ave Unit L, 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
• 

  $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 $2,226,825 Not Listed For Sale

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

  4 Old Farm Rd S, Pleasantville, NY 10570

  4 Old Farm Rd S, Pleasantville, NY 10570
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  /32

  $1,595,000 Pending

  • 5 Beds
  • 6 Baths
  • 4,771 Sq Ft

  19 Trapping Way, Pleasantville, NY 10570

  Welcome Home! This meticulously maintained 5-bedroom Colonial is located in The Estates, in one of the most sought-after school districts Byram Hills School. Set on a beautifully landscaped, level corner lot just under an acre, the property offers both privacy and space—perfect for relaxing or entertaining. The first floor features a chef’s kitchen that opens to a spacious great room, along with

  Stacey Sporn William Raveis Real Estate

  19 Trapping Way, 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
• 

  Est $1,172,538 Not Listed For Sale

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

  20 Brook Manor, Pleasantville, NY 10570

  20 Brook Manor, Pleasantville, NY 10570
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  /26

  $1,175,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,779 Sq Ft

  698 Bear Ridge Rd, Pleasantville, NY 10570

  AO - Your Dream Home Awaits in the award winning Byram Hills School District. Discover contemporary elegance in this beautifully maintained 3-bedroom, 2-bath ranch. Set back from the road, a long driveway leads to a two-car garage with extra storage, offering both privacy and convenience. The inviting foyer welcomes you with a skylight and soaring cathedral ceiling. The open living area features

  Keri Cipriano William Raveis Real Estate

  698 Bear Ridge Rd, Pleasantville, NY 10570
• 

  $1,087,000 Sold Jun 10, 2025

  • 2,600 Sq Ft
  • $418/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  3 Court St, Pleasantville, NY 10570

  Welcome to this contemporary raised ranch in the heart of Pleasantville, offering both convenience and comfort. The impressive oversized bluestone front steps set the stage for this home. An open floor plan on the main level boasts a living room and dining room with a cathedral ceiling, a cozy fireplace, natural sunlight from the large clerestory windows, and access to the deck. The kitchen

  Donna McKenna Edlund Coldwell Banker Realty

  3 Court St, Pleasantville, NY 10570
• 

  Est $1,751,910 Not Listed For Sale

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

  96 Deerfield Ln N, Pleasantville, NY 10570

  96 Deerfield Ln N, Pleasantville, NY 10570
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  /40

  $999,999 Open Sun 12PM - 3PM

  • 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
• 

  $825,000 Sold Jun 09, 2025

  • 1,771 Sq Ft
  • $466/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  70 Oak Ridge Rd, Pleasantville, NY 10570

  Welcome to the sought-after Bear Ridge Neighborhood and to this meticulously renovated, south-facing modern Ranch, nestled in the quaint and desirable village of Pleasantville. From the moment you get out of your car and walk through the front door, you’re warmly welcomed by an open, flowing floorplan bathed in natural light. Inside, beautiful hardwood floors lead you through a spacious living

  David Calabrese Howard Hanna Rand Realty

  70 Oak Ridge Rd, Pleasantville, NY 10570
• 

  Est $1,105,567 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  105 Deerfield Ln N, Pleasantville, NY 10570

  105 Deerfield Ln N, Pleasantville, NY 10570
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  /36

  $2,650,000

  • 5 Beds
  • 4.5 Baths
  • 5,947 Sq Ft

  14 Vista Ct, Pleasantville, NY 10570

  This house offers approximately 5,900 square feet of living space with five bedrooms and four and a half bathrooms. The primary bedroom features ample space with a private en-suite bathroom, offering a serene retreat. The four additional bedrooms provide comfortable accommodations for guests or family members. The home boasts a well-appointed kitchen with high-end appliances, ample counter space,

  James Garcia Coldwell Banker Realty

  14 Vista Ct, Pleasantville, NY 10570
• 

  $1,050,000 Sold Jun 03, 2025

  • 2,448 Sq Ft
  • $429/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1995

  10 Club Ct, Pleasantville, NY 10570

  Welcome to Pleasantville Country Club where luxury meets convenience in this desirable and private end unit townhome centrally situated on a Cul de sac. Reminiscent of the classic style brownstone complete with front stoop perfect for sipping summer lemonade. This meticulous home is perfect for entertaining and offers a luxurious kitchen adorned by solid wood inset custom cabinetry, beautiful

  Kile Boga-Ibric Houlihan Lawrence Inc.

  10 Club Ct, Pleasantville, NY 10570
• 

  Est $1,457,543 Not Listed For Sale

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

  23 Heritage Dr, Pleasantville, NY 10570

  23 Heritage Dr, Pleasantville, NY 10570
• 

  

  /19

  $510,000

  • 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
• 

  $1,350,000 Sold Jun 03, 2025

  • 2,468 Sq Ft
  • $547/SF
  • 14 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1920

  34 Sarles Ln, Pleasantville, NY 10570

  Step into this beautifully maintained early 1900's home, where classic charm meets modern convenience. With three stories of gracious living space and high ceilings, this home offers a warm and inviting atmosphere. Nestled in a neighborhood easily accessible to schools, parks, restaurants, transportation, and more; all just moments from your doorstep. As you enter, you encounter a light-filled

  Danielle Orellana William Raveis Real Estate

  34 Sarles Ln, Pleasantville, NY 10570
• 

  Est $1,543,359 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,245 Sq Ft

  5 Heritage Dr, Pleasantville, NY 10570

  5 Heritage Dr, Pleasantville, NY 10570
• 

  

  /19

  $245,000

  • 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
• 

  $1,405,521 Sold May 28, 2025

  • 2,856 Sq Ft
  • $492/SF
  • 20 Days On Market

  • 6 Beds
  • 2.5 Baths
  • Built 1906

  214 Edgewood Ave, Pleasantville, NY 10570

  First time on the market in 25 years, this grand, yet warmly inviting 1906 gem is nestled in the heart of Pleasantville on one of the most sought-after village streets. This property effortlessly combines timeless charm with the modern amenities sophisticated buyers expect. The architectural artistry is evident throughout, with crown molding, coffered ceilings, a stone fireplace, and beautiful

  Loretta Fleming Chiavetta Coldwell Banker Realty

  214 Edgewood Ave, Pleasantville, NY 10570
• 

  Est $745,056 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft

  161 Lake Shore Dr, Pleasantville, NY 10570

  161 Lake Shore Dr, Pleasantville, NY 10570
• 

  

  /50

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 3,917 Sq Ft

  29 Cedar Ln, Pleasantville, NY 10570

  Welcome to your dream home nestled in the serene cul-de-sac of Pleasantville. This stunning 4-bedroom, 4-bathroom residence spans an impressive 3917 square feet, offering luxurious living with a touch of modern elegance. Step inside to discover a home that was rebuilt in 2023 and designed by local architect Tim Leonard. A beautiful open floor plan adorned with exquisite wood floors that flow

  Karen O'Connor Compass Greater NY, LLC

  29 Cedar Ln, Pleasantville, NY 10570
• 

  $800,000 Sold May 28, 2025

  • 2,000 Sq Ft
  • $400/SF
  • 16 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1881

  19 Elm St, Pleasantville, NY 10570

  Beautifully renovated, 4 bedroom Colonial perfectly situated near all Pleasantville has to offer! Walking distance to the iconic Jacob Burns Film Center, local boutiques and shops, multiple restaurants, Metro North and the heart of Pleasantville. This wonderfully appointed home will not disappoint! Updated in 2020, this home features new hardwood floors throughout. Enter through a welcoming foyer

  Indira Ranganathan Guard Hill Realty

  19 Elm St, Pleasantville, NY 10570
• 

  Est $1,129,333 Not Listed For Sale

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

  311 Bear Ridge Rd, Pleasantville, NY 10570

  311 Bear Ridge Rd, Pleasantville, NY 10570
• 

  

  /13

  $569,000

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

  9 Foxwood Dr Unit 4, Pleasantville, NY 10570

  Sophistication meets comfort at this stunning Tudor-style residence in the highly sought-after Foxwood community. One of the largest units in the complex, this sun-drenched home offers a gracious layout with one spacious bedroom, a versatile office/guest room, and 2 beautifully appointed baths. Expansive windows flood the living spaces with natural light, highlighting elegant finishes and

  Laurie Correia Houlihan Lawrence Inc.

  9 Foxwood Dr Unit 4, Pleasantville, NY 10570
• 

  $655,000 Sold May 27, 2025

  • 1,608 Sq Ft
  • $407/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1963

  109 Marble Ave, Pleasantville, NY 10570

  Attention Contractors and Homeowners! An opportunity has hit the market in the sought-after town of Pleasantville, zoned RO-3 for Residential/Commercial use. Whether you are looking for a property where you can live and work in the same place or an investor looking for income-generating homes, look no further! This multi-family property has many different opportunities to explore. Description of

  Lisa DaRos Houlihan Lawrence Inc.

  109 Marble Ave, Pleasantville, NY 10570
• 

  Est $1,633,575 Not Listed For Sale

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

  245 Bear Ridge Rd, Pleasantville, NY 10570

  245 Bear Ridge Rd, Pleasantville, NY 10570
• 

  

  /21

  $1,149,500

  • 3 Beds
  • 2.5 Baths
  • 2,714 Sq Ft

  20 Dennis Ln, Pleasantville, NY 10570

  Welcome to this stunning 3-bedroom, 2.5-bath home, thoughtfully designed newer construction with space, style, and comfort in mind. Featuring high ceilings and a bright, open floor plan, this home offers an ideal setting for both everyday living and entertaining. The gorgeous open kitchen flows seamlessly into the main living area and out to a private outdoor deck, perfect for relaxing or hosting

  Daniela Grisanti HomeSmart Homes & Estates

  20 Dennis Ln, Pleasantville, NY 10570
• 

  $621,000 Sold May 23, 2025

  • 1,036 Sq Ft
  • $599/SF
  • 12 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  48 Foxwood Dr Unit 4, Pleasantville, NY 10570

  This beautifully updated 2-bedroom, 1.5-bathroom townhome offers effortless one-level living with no stairs! Featuring wood floors throughout, a stylish kitchen with quartz countertops & stainless steel appliances, and an in-unit washer/dryer. A French door off the dining area opens to a private porch, perfect for morning coffee or fresh air. Located in the sought-after Pleasantville School

  Karin Kimtis Compass Greater NY, LLC

  48 Foxwood Dr Unit 4, Pleasantville, NY 10570
• 

  Est $677,903 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  105 Lake Shore Dr, Pleasantville, NY 10570

  105 Lake Shore Dr, Pleasantville, NY 10570
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  /43

  $977,700

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  290 Mountain Rd, Pleasantville, NY 10570

  Modern Living Meets Natural Beauty in the Heart of Pleasantville. Perched above the charming village of Pleasantville, this modern masterpiece has been completely rebuilt from the ground up, offering a one-of-a-kind blend of contemporary design and character. Set on nearly three-quarters of an acre, the home offers privacy and serenity—yet is located under a mile from Metro North, with express

  Matthew Valvano Berkshire Hathaway HS NY Prop

  290 Mountain Rd, Pleasantville, NY 10570
• 

  $800,000 Sold May 07, 2025

  • 1,830 Sq Ft
  • $437/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  679 Washington Ave, Pleasantville, NY 10570

  Welcome to this graceful split-level home featuring 3 bedrooms and 2 baths on a serene half-acre of property close to downtown Chappaqua. The exterior boasts a large circular driveway, stone front walkway, back patio, and beautifully maintained mature shrubs, trees and flower gardens. As you step inside you will find hardwood oak floors and crown molding adding warmth and elegance throughout.

  Donna McKenna Edlund Coldwell Banker Realty

  679 Washington Ave, Pleasantville, NY 10570
• 

  Est $729,445 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,650 Sq Ft

  135 Lake Shore Dr, Pleasantville, NY 10570

  135 Lake Shore Dr, Pleasantville, NY 10570

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