19

Pleasantville, NY Homes for Sale

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  • /27

    $739,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    82 Birch Dr, Pleasantville, NY 10570

    Welcome to 82 Birch Drive, a charming 3-bedroom, 1-bath home situated on two parcels along a quiet dead-end street in Pleasantville, offering a peaceful hillside setting surrounded by mature trees. Inside, hardwood floors throughout add warmth and character, while a beautiful arched doorway connects the living and dining rooms. The extended living room area features skylights and a high ceiling,

    Agent Photo

    Jenny Colon

    Coldwell Banker Realty

    82 Birch Dr, Pleasantville, NY 10570
  • /20

    $425,000

    • 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
  • /50

    $1,200,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 1.5 Baths
    • 1,745 Sq Ft

    35 Grandview Ave, Pleasantville, NY 10570

    There’s something truly special about this captivating Pleasantville Craftsman. It has the kind of charm and character that is hard to find in newer homes, along with a wonderful location right in the heart of Pleasantville. The moment you enter, you’ll notice the hardwood floors, large windows, and abundance of natural light filling the rooms. But the real star of the show may be the oversized

    Agent Photo

    Donald Dwyer

    Howard Hanna Rand Realty

    35 Grandview Ave, Pleasantville, NY 10570
  • /15

    $259,000

    $16K PRICE DROP
    • 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

    $1,225,000

    • 4 Beds
    • 2 Baths
    • 2,722 Sq Ft

    1 Grandview Cir, Pleasantville, NY 10570

    Welcome to this beautifully situated 4-bedroom, 2-full-bath home in the heart of Pleasantville! Featuring a spacious primary bedroom, a large formal living room, and plenty of room to live, work, and entertain, this home offers both comfort and convenience. Enjoy the best of Pleasantville living with a truly walkable location close to schools, the train station, local farmers markets, and the

    Sharon Foley ERA Insite Realty Services

    1 Grandview Cir, Pleasantville, NY 10570
  • /29

    $819,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,733 Sq Ft

    3 Douglas Dr, Pleasantville, NY 10570

    Beautifully maintained and lovingly cared for, this inviting home is nestled on a private cul-de-sac and offers a true sense of sanctuary. The main level is filled with natural sunlight from large windows and two sliding glass doors, creating a warm and welcoming atmosphere throughout. The spacious living room features sliding glass doors leading to an expansive deck, seamlessly connecting the

    Aileen Riordan Houlihan Lawrence Inc.

    3 Douglas Dr, Pleasantville, NY 10570
  • /25

    $639,000

    • 3 Beds
    • 1 Bath
    • 855 Sq Ft

    1 Brentwood Dr, Pleasantville, NY 10570

    Welcome to this charming 3-bedroom, 1-bath Pleasantville ranch. This home offers a wonderful opportunity for a first-time buyer or anyone looking for the ease of one-level living. Situated on a corner lot, the home offers comfortable living spaces and an opportunity to make it your own.The location is a standout. Enjoy the convenience of being centrally located near Pleasantville schools,

    Concetta Connie Gallo Howard Hanna Rand Realty

    1 Brentwood Dr, Pleasantville, NY 10570
  • /35

    $899,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    4 Depew St, Pleasantville, NY 10570

    ATTENTION 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
  • /38

    $750,000

    Open Sat 10:30AM - 12:30PM
    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    3 Elm St, Pleasantville, NY 10570

    Live in the heart of Pleasantville in a home as distinctive as its location. Just 0.4 mile from Metro North and moments from the village center, 3 Elm Street pairs an exceptionally convenient location with interiors that feel anything but expected. Fully renovated, this three bedroom Colonial features dark painted trim, rich color, patterned wallpaper and thoughtfully chosen finishes that give

    Melissa Colabella Compass Greater NY, LLC

    3 Elm St, Pleasantville, NY 10570
  • /22

    $479,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    590 Bedford Rd Unit 1, Pleasantville, NY 10570

    Easy Living in the Heart of Pleasantville!Welcome to this beautiful two-bedroom, first-floor condo in the desirable Greenwood Condominiums, offering no steps and effortless one-level living.Freshly painted and filled with natural light, this spacious home features a welcoming living room, updated kitchen with stainless steel appliances, warm wood cabinetry and a convenient

    Maura Mcspedon William Raveis Real Estate

    590 Bedford Rd Unit 1, Pleasantville, NY 10570
  • /39

    $1,300,000

    • 3 Beds
    • 3.5 Baths
    • 3,866 Sq Ft

    29 Country Club Ln, Pleasantville, NY 10570

    Enjoy this beautifully updated, and stylishly appointed, corner unit home in the highly desirable Pleasantville Country Club community. You will appreciate the ease of a maintenance-free, resort-style living, where you can spend more time enjoying the wonderful amenities and less time worrying about upkeep. Offering three levels of spacious living, the home welcomes you with a dramatic two-story

    Maura Mcspedon William Raveis Real Estate

    29 Country Club Ln, Pleasantville, NY 10570
  • /39

    $1,500,000

    • 4 Beds
    • 2.5 Baths
    • 3,663 Sq Ft

    37 Pheasant Run Rd, Pleasantville, NY 10570

    Welcome to 37 Pheasant Run Road, a sun-drenched sanctuary offering seamless indoor-outdoor living in Pleasantville’s premier Estates neighborhood. Set comfortably back from the road on a beautiful, private lot surrounded by lush gardens, this custom-crafted home features an open layout bathed in exceptional natural light. Designed for both dynamic entertaining and peaceful everyday living, the

    Jocelyn Cloder Compass Greater NY, LLC

    37 Pheasant Run Rd, Pleasantville, NY 10570
  • /32

    $1,325,000

    $74K PRICE DROP
    • 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
  • /31

    $599,000

    • 3 Beds
    • 1 Bath
    • 1,329 Sq Ft

    582 Washington Ave, Pleasantville, NY 10570

    First time on the market in over 50 years—an exciting opportunity to create something truly your own in an exceptional location! Ideally situated between the vibrant Villages of Pleasantville and Chappaqua, this split-level home offers a wonderful canvas for its next owner to renovate, reimagine, and make their own. Inside, hardwood floors and abundant natural light set the stage for a fresh

    Karin Morano Corcoran Legends Realty

    582 Washington Ave, Pleasantville, NY 10570
  • /27

    $724,900

    • 4 Beds
    • 1 Bath
    • 1,626 Sq Ft

    45 Leroy St, Pleasantville, NY 10570

    Nestled in the midst of an idyllic, tree-filled, half-acre setting, this charming, character-filled gem is ideal for working from home, relaxing and entertaining!Upon entry, the foyer opens to a formal living room with several architectural features of note -- a beautiful arched, vaulted ceiling, hardwood floors and a fireplace withstone trim. At the opposite end of the room is a huge

    Pamela Jones Coldwell Banker Realty

    45 Leroy St, Pleasantville, NY 10570
  • /34

    $929,000

    • 4 Beds
    • 2.5 Baths
    • 2,390 Sq Ft

    1 Brookfield Place, Pleasantville, NY 10570

    Welcome to this inviting 4-bedroom, 2.5-bath home ideally located just outside the heart of Pleasantville Village. Enjoy the convenience of being within easy walking distance to town, with its restaurants, shops, entertainment, and everyday amenities. The home offers a flexible layout with a private in-law/guest suite, perfect for extended family, guests, or additional living space. A spacious

    Sharon Foley ERA Insite Realty Services

    1 Brookfield Place, Pleasantville, NY 10570
  • /49

    $2,499,999

    Open Sat 1PM - 3PM
    • 5 Beds
    • 5 Baths
    • 5,055 Sq Ft

    26 Cecilia Ln, Pleasantville, NY 10570

    Experience modern luxury at 26 Cecilia Lane, a completely move-in-ready, 5,055-square-foot contemporary ranch that pairs impressive scale with the effortless ease of predominantly first floor living. Flooded with natural light and set on more than 1.5 acres of professionally landscaped, flat and usable grounds, this exceptional residence offers 5 bedrooms, 3 full bathrooms, two powder rooms and

    Leslie Shemin-Lester Julia B Fee Sothebys Int. Rlty

    26 Cecilia Ln, Pleasantville, NY 10570
  • /35

    $619,000

    • 2 Beds
    • 2 Baths
    • 1,298 Sq Ft

    16 Foxwood Dr Unit 8, Pleasantville, NY 10570

    Welcome to desirable Foxwood Condominiums in Pleasantville! A rare opportunity to unlock the full potential of this 2 bedroom 2 full bath Somerset unit. Entry Foyer with 2 Closets, Spacious Eat-in Kitchen with Dining area, additional Cabinetry, Formal Dining and Living Room with Picture Window and a Door Out to the Deck. Hall Bathroom, Hall Linen and Laundry Closets, Primary Bedroom with Primary

    Lena O'Neill Howard Hanna Rand Realty

    16 Foxwood Dr Unit 8, Pleasantville, NY 10570
  • /31

    $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.

Pleasantville, NY Home Prices

Pleasantville, NY
Median Home Price
$849,000
Median Sale Price
$876,000
+4% YoY
Avg. Price per Square Foot
$487
Median Single Family Price
$919,500
Median Townhouse Price
$1,268,750
Median Condo Price
$270,000
Total Active Listings
19 listings
Market Conditions
2 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Pleasantville, NY?
Homes for sale in Pleasantville, NY have an average home price of $862,583.
How many homes have sold over the last 12 months in Pleasantville, NY?
79 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 $849,000. If you put a 20% down payment of $169,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $4,500 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $193K 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.
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