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Pleasantville, NY Homes for Sale

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  • /21

    $425,000

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 762 Sq Ft

    8 Foxwood Dr Unit 8, Pleasantville, NY 10570

    Step into elegance and comfort in this beautifully maintained, rarely available second-floor Pembroke model condominium in the highly sought-after Foxwood community. This move-in-ready home offers the perfect blend of style, convenience, and low-maintenance living.The bright eat-in kitchen features attractive butcher block-style countertops, beautiful white cabinetry, abundant storage and

    Agent Photo

    Michael Dunstan

    RE/MAX Town & Country

    8 Foxwood Dr Unit 8, Pleasantville, NY 10570
  • /15

    $275,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    73 Broadway Unit 2J, Pleasantville, NY 10570

    Updated and meticulously maintained co-op ideally located just moments from both the heart of Pleasantville and the Metro-North station, offering an effortless commute and vibrant village living. This inviting home features a modern, comfortable layout and quality finishes throughout. The updated kitchen offers clean lines, ample cabinetry, and functional workspace designed for everyday living

    Thomas Consaga RE/MAX Ace Realty

    73 Broadway Unit 2J, Pleasantville, NY 10570
  • /35

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    4 Depew St, Pleasantville, NY 10570

    ATTEENTION WORK-AT -HOME PROFESSIONALS AND THOSE SEEKING MOTHER DAUGHTER SET UP! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to

    Al Posillico Keller Williams Realty Group

    4 Depew St, Pleasantville, NY 10570
  • /31

    $475,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    590 Bedford Rd Unit 3, Pleasantville, NY 10570

    Welcome home to effortless, low-maintenance living in the highly sought-after Greenwood Condominium complex. Located on the first floor with seamless, step-free access, this bright and inviting 2-bedroom home pairs mid-century charm with smart, modern updates. Inside, refinished hardwood floors and generous natural light frame serene views of the beautifully landscaped grounds. The thoughtful

    Susan Hawkins Julia B Fee Sothebys Int. Rlty

    590 Bedford Rd Unit 3, Pleasantville, NY 10570
  • /48

    $748,000

    • 2 Beds
    • 2 Baths
    • 1,275 Sq Ft

    21 Foxwood Dr Unit 2, Pleasantville, NY 10570

    Foxwood Condominium Pleasantville, Picturesque Country Setting with Meticulously Kept Grounds.. Foxwood's 1st Floor " Stuart " Model with1,275 Square Feet of 1 Level Living.. Beautifully Updated Eat in Kitchen with Additional Cabinetry and Granite Counters, Decorative Tile Backsplash, Accommodating Dining Area and Pantry.. Entry Foyer with Closet, Spacious Living Room with Picture Window, Wood

    Vincent Vetrano Douglas Elliman Real Estate

    21 Foxwood Dr Unit 2, Pleasantville, NY 10570
  • /24

    $2,100,000

    $250K PRICE DROP
    • 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
  • /32

    $1,399,000

    Open Sun 1PM - 2:30PM
    • 3 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    18 Brookview Dr, Pleasantville, NY 10570

    Enjoy carefree and resort-style living in the Pleasantville Country Club community! Perfectly situated as one of only ten homes at the end of a private cul-de-sac, this beautifully updated 3-bedroom, 3.5-bath townhome offers 3,434 square feet of elegant living space. The main level features a fabulous Kingswood gourmet kitchen, complete with a large granite center island, top-of-the-line

    Justine Flanagan Houlihan Lawrence Inc.

    18 Brookview Dr, Pleasantville, NY 10570
  • /16

    $435,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    600 Bedford Rd Unit 9, Pleasantville, NY 10570

    Rare opportunities like this are almost impossible to find in Pleasantville. Completely renovated from top to bottom and never lived in after the renovation, this mint-condition Greenwood Condominium offers true turnkey living in one of Westchester's most walkable communities. Every inch of the home has been thoughtfully updated, including brand-new flooring throughout, a stunning new kitchen

    Matthew Gluck Nestedge Realty

    600 Bedford Rd Unit 9, Pleasantville, NY 10570
  • /23

    $689,000

    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft

    660 Washington Ave, Pleasantville, NY 10570

    Welcome to 660 Washington Avenue, a ranch-style home offering the ease of single-level living with the added benefit of flexible lower-level space. The main level features a sun-filled living room, dining area, eat-in kitchen, three comfortable bedrooms, and an updated full bath with radiant heated floors. Large windows throughout the home fill the interior with natural light and create a warm,

    Regina Martinez eXp Realty

    660 Washington Ave, Pleasantville, NY 10570
  • /27

    $199,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 750 Sq Ft

    310 Manville Rd Unit S4, Pleasantville, NY 10570

    COMMONS OF PLEASANTVILLE. This beautifully updated one-bedroom Co-op in the charming Village of Pleasantville NY, offers the perfect blend of style and convenience . The unit features a brand new kitchen with sleek stainless steel appliances, a newly renovated bath, rich wood floors, and impressive high ceilings that create a bright and airy feel. Ideally located just moments from the metro-north

    Lena O'Neill Howard Hanna Rand Realty

    310 Manville Rd Unit S4, Pleasantville, NY 10570
  • /33

    $849,999

    $49K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    249 Mill River Rd, Chappaqua, NY 10514

    NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed

    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.

Frequently Asked Questions

What is the average home price in Pleasantville, NY?
Homes for sale in Pleasantville, NY have an average home price of $825,840.
Are home prices dropping in Pleasantville?
Yes, home prices in Pleasantville are down 4% in the last 12 months.
How many homes have sold over the last 12 months in Pleasantville, NY?
70 homes have sold in Pleasantville, NY over the last 12 months.
What is the average household income in Pleasantville, NY?
The average household income in Pleasantville, NY is $190K.
What are the most popular zip codes in Pleasantville, NY?
The most popular zip codes in Pleasantville, NY include 10570, 10514, 10594, 10532 and 10510.
How much do you need to make to afford a house in Pleasantville?
The median home price in Pleasantville is $775,000. If you put a 20% down payment of $155,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $4,000 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $171K a year to afford the median home price in Pleasantville. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Pleasantville is $190K.
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, Briarcliff Middle School and Horace Greeley High School. Browse all the schools in Pleasantville, NY to learn more.

Home Price Trends

Median Sale Price
$818,250
Median Single Family Sale Price
$836,500
Median Townhouse Sale Price
$1,237,500
Median 2 Bedroom Sale Price
$649,000
Median 1 Bedroom Sale Price
$420,500
Average Price Per Sq Ft
$474
Number of Homes for Sale
9
Last 12 months Home Sales
70
Months of Supply
1.50
Median List Price
$775,000
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-8%
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