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Pleasantville, NY Homes for Sale

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  • /45

    $1,395,000

    • 3 Beds
    • 3.5 Baths
    • 3,703 Sq Ft

    46 Dennis Ln, Pleasantville, NY 10570

    Enjoy carefree living in this exquisite private townhome located in the highly desirable Enclave in Pleasantville. Meticulously upgraded with luxurious finishes, the primary suite is conveniently situated on the main level for those looking for one-level living. Natural light floods the home through a two-story entryway, flanked by a formal dining room and a den featuring built-in shelves and a

    Agent Photo

    Maria Teresa Duguet

    Houlihan Lawrence Inc.

    (914) 877-2498

    46 Dennis Ln, Pleasantville, NY 10570
  • /23

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,491 Sq Ft

    184 Deerfield Ln N, Pleasantville, NY 10570

    Step into timeless elegance with this stately colonial in a highly desirable neighborhood. The grand two-story entry welcomes you and bathes the home in natural sunlight. High ceilings, skylights, expansive windows and the beautiful flow enhance every inch of this home.The step-down living room is flooded with natural light, while the adjacent family room with a fireplace complete with wet

    Joanne Georgiou William Raveis-New York, LLC

    184 Deerfield Ln N, Pleasantville, NY 10570
  • /36

    $1,695,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 4.5 Baths
    • 4,707 Sq Ft

    117 Deerfield Ln N, Pleasantville, NY 10570

    This refreshed, sun-filled Colonial home with a lovely gunite pool, located in the award winning Byram Hills School District, is ready for it's next owner. The remodeled gourmet kitchen featuring high-end appliances, a center island, custom cabinets and stunning new counters seamlessly connects to the family room, where a stone fireplace sets the stage for cozy gatherings. The living and dining

    Patti Howard Compass Greater NY, LLC

    117 Deerfield Ln N, Pleasantville, NY 10570
  • /34

    $1,450,000 Open Sun 3PM - 4:30PM

    • 6 Beds
    • 3.5 Baths
    • 3,144 Sq Ft

    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 kitchen,

    Christine Bamford Elegran LLC

    49 Walnut St, Pleasantville, NY 10570
  • /29

    $1,395,000

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

    140 Old Farm Rd S, Pleasantville, NY 10570

    Welcome to your exclusive paradise. Surrounded by beautiful level yard, the pool entertainment area will take your breath away. Professionally landscaped, illuminated and fully fenced, this property is truly one of a kind, prioritizing privacy and tranquility. A custom-built stone barbecue enhances everyday entertainment. Interior is impressive with an open flow layout, lots of large windows

    Jaimme Pudalov Houlihan Lawrence Inc.

    140 Old Farm Rd S, Pleasantville, NY 10570
  • /13

    $1,249,000

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    133 Lake Shore Dr, Pleasantville, NY 10570

    Don’t miss the chance to create your perfect home! This modern young colonial, is currently under construction by an experienced builder, offers a unique opportunity to tailor the design to your preferences. There is still time to customize! Currently under construction, frame, windows, siding, and plumbing is completed. Built with high-quality materials, including Andersen 400 Series windows and

    Natalia Wixom Compass Greater NY, LLC

    133 Lake Shore Dr, Pleasantville, NY 10570
  • /46

    $1,150,000

    • 4 Beds
    • 4 Baths
    • 3,444 Sq Ft

    263 Mill River Rd, Chappaqua, NY 10514

    Step through the automatic double gates into your private sanctuary, framed by a stately stone wall entrance, a charming blue stone and Belgium block walkway, and elegant wrought iron railings. This breathtaking property is beautifully landscaped with lush flower gardens, expansive emerald lawns, and an array of specimen trees and fruit plants that create a serene, park-like setting.Located just

    Carolina Vinciguerra RE/MAX Town & Country

    263 Mill River Rd, Chappaqua, NY 10514
  • /23

    $1,725,000

    • 4 Beds
    • 4.5 Baths
    • 3,561 Sq Ft

    260 Mill River Rd, Chappaqua, NY 10514

    Discover the perfect townhouse alternative or an ideal first home just north of NYC! Nestled on Mill River Road, this inviting 4-bedroom residence offers the best of both worlds—walking distance to the charming town of Chappaqua, with its shops, restaurants, and train station, while benefiting from the highly regarded Pleasantville schools. Commuting is a breeze with the Chappaqua train station

    Sari Shaw Compass Greater NY, LLC

    260 Mill River Rd, Chappaqua, NY 10514
  • /27

    $569,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    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
  • /33

    $839,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    52 Seneca Ln, Pleasantville, NY 10570

    Do not miss this lovely three-bedroom, two-and-a-half-bath, tastefully appointed and renovated cozy home. Located on a serene cul-de-sac, yet just a short stroll from the lively village center with great community spirit, and the proximity to a public swimming pool. The home also sits right next to the golf course, offering sweeping views of the lush natural greens. Enjoy the perfect balance of

    Denis Knox Howard Hanna Rand Realty

    52 Seneca Ln, Pleasantville, NY 10570
  • /29

    $749,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,771 Sq Ft

    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
  • /4

    $300,000

    • Land
    • 0.11 Acre
    • $2,727,273 per Acre

    85 Sarles Ln, Pleasantville, NY 10570

    Calling all builders! With variances this is a buildable lot in prime village location. Water and sewer available.

    Sharon Foley ERA Insite Realty Services

    85 Sarles Ln, Pleasantville, NY 10570
  • /35

    $725,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    8 Douglas Dr, Pleasantville, NY 10570

    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 offers ample cabinetry, and large

    Jeanne Beckley Howard Hanna Rand Realty

    8 Douglas Dr, Pleasantville, NY 10570
  • /19

    $435,000

    • 1 Bed
    • 1 Bath
    • 760 Sq Ft

    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
  • /32

    $889,000

    • 3 Beds
    • 3 Baths
    • 1,848 Sq Ft

    9 Grandview Dr, Pleasantville, NY 10570

    Location, Location, Location. There are no truer words. This house has the perfect location. Walking distance to Pleasantville Schools and all that the Village of Pleasantville has to offer, from its many restaurants to the famous farmer's market to the acclaimed Jacob Burns movie theater. Bring your dreams to this home and make it your own. The opportunities are endless.

    Sharon Foley ERA Insite Realty Services

    9 Grandview Dr, Pleasantville, NY 10570
  • /24

    $929,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,766 Sq Ft

    80 Madison Ave, Pleasantville, NY 10570

    Welcome home to this immaculate colonial, perfectly nestled at the end of a peaceful street for ultimate privacy. Thoughtfully designed and impeccably maintained, this home offers a blend of classic charm and modern comfort. Step inside to discover an inviting open-concept kitchen connected to the outside covered deck and dining area, perfect for both casual meals and entertaining. The spacious

    James Campbell Houlihan Lawrence Inc.

    80 Madison Ave, Pleasantville, NY 10570
  • /40

    $1,075,000

    • 6 Beds
    • 4 Baths
    • 3,000 Sq Ft

    41 Saratoga Ave, Pleasantville, NY 10570

    Incredible opportunity in Mount Pleasant! Yes! It’s TWO Investment properties on ONE Lot! The front house holds the first Unit which is a 3-bed, 1-bath first-floor unit featuring a spacious living room, and kitchen. Open Kitchen just recently renovated. Hardwood floors throughout, bright natural lighting, and a newly tiled kitchen floor. Enjoy the convenience of the downstairs storage and

    Christine Ricci Keller Williams NY Realty

    41 Saratoga Ave, Pleasantville, NY 10570
  • /34

    $3,300,000

    • 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 3 picturesque acres. This sunlit residence boasts 6 spacious bedrooms and 4 1/2 bathrooms, making it the perfect sanctuary for large families and entertaining guests. Step inside to experience the remarkable craftsmanship that defines this home. With oversized rooms designed for both formal gatherings and

    Stacey Sporn William Raveis Real Estate

    235 Bear Ridge Rd, Pleasantville, NY 10570

About Pleasantville

Pleasantville, New York, is a page from a storybook with its quaint homes, tree-lined streets, lovely downtown, and emphasis on community. “Every town has a community, but there’s something unique about the sense of community here. The village is small, and everything is easily accessible. We don’t have school buses, so children, parents and caregivers walk to and from school and get to know each other. Through this, kids become friends with their friend’s siblings, parents become friends with each other, and it continues to build close relatio ...

Frequently Asked Questions

What is the average home price in Pleasantville, NY?
Homes for sale in Pleasantville, NY have an average home price of $1,065,684.
How many homes have sold over the last 12 months in Pleasantville, NY?
52 homes have sold in Pleasantville, NY over the last 12 months.
Is Pleasantville, NY a safe city?
In general, the safest neighborhood in Pleasantville, NY with lower crime scores is Pleasantville.
What are the most popular zip codes in Pleasantville, NY?
The most popular zip codes in Pleasantville, NY include 10463, 10471, 10583, 10708 and 06830.
What are the most popular neighborhoods in Pleasantville, NY?
The most popular neighborhood in Pleasantville, NY with the most homes for sale is Pleasantville.
How much do you need to make to afford a house in Pleasantville?
The median home price in Pleasantville is $1,100,000. If you put a 20% down payment of $220,000 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $5,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $246K a year to afford the median home price in Pleasantville.
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 Todd Elementary School. The neighborhood in Pleasantville with the highest rated schools is Pleasantville. Browse all the schools in Pleasantville, NY to learn more.

Home Trends in Pleasantville, NY

Home Trends

Median Price (12 Mo)
$1,132,500
Median Single Family Price
$1,140,000
Median Townhouse Price
$790,000
Median 2 Bedroom Price
$275,000
Median 1 Bedroom Price
$500,000
Average Price Per Sq Ft
$445
Number of Homes for Sale
7
Last 12 months Home Sales
52
Months of Supply
1.60
Median List Price
$1,100,000
Median Discount From 1st List Price
-1%
Median Home Sale Price YoY Change
32%
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