10

Pleasantville, NY Homes for Sale

Section Image Section Image
  • /42

    $1,350,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 3,228 Sq Ft

    57 Dennis Ln, Pleasantville, NY 10570

    Experience the pinnacle of sophisticated, maintenance-free living in this stunning end-unit townhouse at The Enclave. Built in 2019 by renowned builder Toll Brothers, this impeccably maintained 3-bedroom, 2.5-bath home enjoys premier southern exposure, filling the interior with natural light throughout the day. The open-concept main level is designed for modern living and effortless entertaining,

    Agent Photo

    Maria Teresa Duguet

    Houlihan Lawrence Inc.

    (914) 281-2581

    57 Dennis Ln, 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 powder

    Agent Photo

    Miriam Dunn

    RE/MAX Prime Properties

    (914) 604-3484

    31 Pierce Dr, Pleasantville, NY 10570
  • /35

    $249,900

    • 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
  • /22

    $600,000

    • 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
  • /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
  • /30

    $459,000

    • 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
  • /47

    $875,000

    • 3 Beds
    • 1 Bath
    • 1,456 Sq Ft

    175 Washington Ave, Pleasantville, NY 10570

    Offered for the first time in over 90 years, this cherished village home presents a rare opportunity to become part of Pleasantville’s rich community fabric. Lovingly held by the same family for generations, this 3-bedroom, 1.5-bath residence is ready for its next chapter, offering endless potential for renovation, expansion, or personalization.The home features a classic layout filled with

    Mary McCabe William Raveis-New York LLC

    175 Washington Ave, Pleasantville, NY 10570
  • /39

    $899,000

    • 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
  • /2

    $399,999

    • Land
    • 0.11 Acre
    • $3,636,355 per Acre

    85 Sarles Ln, Pleasantville, NY 10570

    Rare vacant lot opportunity in the Village of Pleasantville with major pre-development work already completed. Property will be delivered ready for building permit submission, including survey, topo, site plan, drainage plan, architectural plans, color floor plans, and renderings. All required variances have been obtained from the Village of Pleasantville. Designed for a 2,315 SF single-family

    Anthony Crecco Crecco Real Estate

    85 Sarles Ln, Pleasantville, NY 10570
  • /17

    $480,000

    • 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

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.

Frequently Asked Questions

What is the average home price in Pleasantville, NY?
Homes for sale in Pleasantville, NY have an average home price of $822,519.
Are home prices dropping in Pleasantville?
Yes, home prices in Pleasantville are down 8% in the last 12 months.
How many homes have sold over the last 12 months in Pleasantville, NY?
71 homes have sold in Pleasantville, NY over the last 12 months.
What are the most popular zip codes in Pleasantville, NY?
The most popular zip codes in Pleasantville, NY include 10570, 10514, 10594, 10549 and 10510.
How much do you need to make to afford a house in Pleasantville?
The median home price in Pleasantville is $799,499. If you put a 20% down payment of $159,900 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $4,030 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $173K a year to afford the median home price in Pleasantville. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Pleasantville, NY?
Pleasantville, NY has highly rated public and private schools. Some of the best schools in Pleasantville based on Niche Grades are Briarcliff High School, Horace Greeley High School and Briarcliff Middle School. Browse all the schools in Pleasantville, NY to learn more.

Home Trends in Pleasantville, NY

Housing Trends

Median Sale Price
$836,500
Median Single Family Sale Price
$840,000
Median Townhouse Sale Price
$1,318,750
Median 2 Bedroom Sale Price
$554,500
Median 1 Bedroom Sale Price
$447,500
Average Price Per Sq Ft
$478
Number of Homes for Sale
7
Last 12 months Home Sales
71
Months of Supply
1.20
Median List Price
$799,499
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
-13%
How to Buy a Home How to Finance a Home How to Sell a Home