14

Pleasantville, NY Houses for Sale

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  • /38

    $1,175,000

    • 3 Beds
    • 3 Baths
    • 3,728 Sq Ft

    57 Hamilton Dr, Chappaqua, NY 10514

    Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom

    Agent Photo

    Sherry Wiggs

    Houlihan Lawrence Inc.

    (914) 862-7931

    57 Hamilton Dr, Chappaqua, NY 10514
  • /50

    $1,499,999

    • 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
  • /37

    $1,525,000

    • 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
  • /40

    $1,425,000

    • 4 Beds
    • 2.5 Baths
    • 3,800 Sq Ft

    306 Mountain Rd, Pleasantville, NY 10570

    Welcome to Pleasantville! This spectacular Center Hall Colonial combines timeless elegance with modern updates and exceptional quality throughout. Featuring four generously sized bedrooms, this meticulously maintained home offers space, comfort, and style at every turn. Step into the updated chef’s kitchen, beautifully appointed with granite countertops, stainless steel appliances, and a cozy

    SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

    306 Mountain Rd, Pleasantville, NY 10570
  • /31

    $1,300,000

    • 3 Beds
    • 2.5 Baths
    • 2,912 Sq Ft

    140 Old Farm Rd S, Pleasantville, NY 10570

    Enjoy vacation like living everyday in this spacious home located on 1 acre of parklike property. This home features a no-step ranch with open floorplan and a beautiful primary suite on the main level. Doors out to a spacious deck overlooking private pool complete with outside kitchen/barbecue area make for a vacation at home. The lower level consists of family room with door out to

    Sharon Foley ERA Insite Realty Services

    140 Old Farm Rd S, Pleasantville, NY 10570
  • /49

    $1,435,000

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

    31 Pierce Dr, Pleasantville, NY 10570

    Welcome to a half acre of heaven. You will fall in love with the incredible landscaping and gardening that has entertained garden club members. The glorious interior is light and bright with lots of windows strategically placed for viewing the beautiful outdoors. Plus, there is additional recessed lighting. The main level consists of a gracious entry foyer and guest closet, along with a

    Miriam Dunn RE/MAX Prime Properties

    31 Pierce Dr, Pleasantville, NY 10570
  • /40

    $999,999

    • 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
  • /32

    $1,099,000

    • 4 Beds
    • 4 Baths
    • 2,461 Sq Ft

    60 Cedar Ave, Pleasantville, NY 10570

    Nestled in a peaceful and private setting on two lots totaling 0.81 acres, this enchanting 1927 French Normandy Tudor home blends timeless charm and modern comfort, including central air. Rich in character, the home showcases original architectural details such as beamed ceilings, classic casement Tudor windows, arched doorways, and a distinctive Belgian tile roof. A gracious tiled entry leads

    Donna McKenna Edlund Coldwell Banker Realty

    60 Cedar Ave, Pleasantville, NY 10570
  • /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
  • /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
  • /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
  • /30

    $830,000

    • 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
  • /45

    $1,025,000

    • 5 Beds
    • 4 Baths
    • 2,916 Sq Ft

    27 Bedford Rd, Pleasantville, NY 10570

    Set in the desirable Village of Pleasantville, this enchanting Colonial home, built in 1830 and sited on .78 acres, offers timeless character, unique architectural details, and endless potential. A true diamond in the rough, this residence, dubbed "Pierce House", is ready to be transformed into something truly spectacular. Far from cookie-cutter, this home tells a story. With its original charm

    Grace LoBello William Raveis Real Estate

    27 Bedford Rd, Pleasantville, NY 10570
  • /49

    $824,000

    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    249 Mill River Rd, Chappaqua, NY 10514

    Contemporary bi-level 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler, and sanitary system. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers

    Harry Donofrio Town and Village Real Estate

    249 Mill River Rd, Chappaqua, NY 10514

Why Live in Pleasantville

Pleasantville, New York, is a small community known for its quaint homes, tree-lined streets, and strong sense of community. The town's highly rated schools, including Bedford Road School, Pleasantville Middle School, and Pleasantville High School, are part of the Pleasantville Union Free School District. The architectural landscape features New England-style colonials, Craftsman-style homes, sprawling ranchers, and custom-built properties, often set on large private lots. Residents enjoy numerous things to do, such as exploring the 45 miles of scenic trails at Rockefeller State Park Preserve or hiking and mountain biking at Graham Hills Park. The Pleasantville Country Club offers golfing opportunities, while the central downtown area is home to charming boutiques, restaurants, and annual events like Pleasantville Day. Popular dining spots include Jean Jacques and Pleasantville Diner, and The Garage at Lucy’s provides a lively atmosphere with live music and arcade games. Essential amenities such as Key Food Marketplace and LA Fitness are conveniently located, and the Jacob Burns Film Center and Pleasantville farmers market offer weekend entertainment. The town is well-connected with access to the Saw Mill River Parkway, various bus stops, and a nearby train station, making commuting to New York City, 35 miles away, straightforward.

Home Trends in Pleasantville, NY

Housing Trends

Median Sale Price
$1,400,444
Median Single Family Sale Price
$1,400,444
Average Price Per Sq Ft
$676
Number of Homes for Sale
2
Last 12 months Home Sales
6
Months of Supply
4.00
Median List Price
$1,200,000
Median Change From 1st List Price
-17%
Median Home Sale Price YoY Change
30%
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