$923,828Average Value$477Average Price per Sq Ft7Homes For Sale
Ties to friends and family bind the community in 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 relationships in the neighborhood,” says Maria Fitzgerald, a town native and real estate salesperson with Coldwell Banker Realty with 17 years of experience.
The Pleasantville Diner on 10 Memorial Plaza serves residents all day.
Pleasantville, New York displays its patriotism throughout the area.
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Pleasantville students attend a roster of top-notch schools
The neighborhood is home to top-tier schools with high ratings on Niche within the Pleasantville Union Free School District. Students here attend Bedford Road School for elementary and Pleasantville Middle School, both scoring an A. Also boasting an A, Pleasantville High School offers a range of after-school activities and is best known for its competitive academics, with 72% of the student population participating in the Advanced Placement program.
Pleasantville Middle School serves the children of Pleasantville, New York.
Pleasantville High School serves all of the high school children of Pleasantville, New York.
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From classic colonials to Craftsman-style homes
Meandering through the tree-lined streets, the quintessential New England-style architecture, with classic colonials displaying front porches and Craftsman-style homes, adds to the small-town charm. However, the architectural landscape also includes sprawling ranchers and custom-built homes scattered throughout. Large private lots and sprawling green landscapes are characteristic of the area, providing ample space for kids and pets to run around. Here, the average home price hovers in the upper 800,000s, with a few modest ranchers starting in the mid 600,000s, to single-family colonials with 2-car garages listed from the upper $600,000s to the upper $900,000s. However, many properties on large lots start around $1 million for a 2.5 acre plot to over $3 million for a custom-designed home with an infinity pool and spa on close to 4 acres on the cusp of the neighborhood.
Colonial Revival homes are among the housing stock in Pleasantville, New York.
Tree lined streets are the norm in Pleasantville, New York.
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Area parks offer scenic trails for hikers and mountain bikers
Residents have endless access to the pristine views at Rockefeller State Park Preserve, with 45 miles of scenic paved trails and rolling landscapes that offer an escape from life’s stressors. For adventure seekers, Graham Hills Park is often filled with hikers and mountain bikers looking to ride the steep terrain against the backdrop of towering oaks, maples and undisturbed woodlands along Bedford Road. Pleasantville Country Club, in the heart of the town, offers a different kind of greenery for those looking to tee off on the range.
Graham Hills Park is one of the most used parks in Pleasantville, New York.
Rugged terrain make for an exciting ride in Graham Hills Park in Pleasantville, New York.
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Bookstores, film screenings and arcade games add charm to downtown
Pleasantville’s central downtown and shopping district is where visitors can enjoy charming boutiques, restaurants, and annual events that genuinely emulate a small-town atmosphere. “Every May, Pleasantville Day happens in the middle of town. All the local businesses come out and showcase what they do, and there are rides and games for the kids,” Fitzgerald says. Here, one can find quaint stores like The Village Book Store offering a range of classics and new reads, while popular eateries dot the streets like Jean Jacques offering French delights. Then there’s Pleasantville Diner, known for its American cuisine, which is a popular spot for the entire family. For a drink after work, The Garage at Lucy’s is the community watering hole, with live music every Tuesday night and a range of arcade games that fills the air with nostalgia. Along with essential establishments, such as Key Food Marketplace for groceries and LA Fitness for workouts, the strip is home to almost everything one could need. On the weekends, locals can watch a movie at the renowned Jacob Burns Film Center or spend Saturday mornings at the Pleasantville farmers market. “It feels like an event every Saturday, with live music, vendors, events for the kids and neighbors saying hello,” Fitzgerald says.
Tghe Black Cow Coffee Roasters is a great spot to grab an espresso mid day.
Locals wait for special orders at Jean Jacques' Culinary Creations in Pleasantville, New York.
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Pleasantville residents and students have access to major highways
Pace University’s secondary campus also calls Pleasantville home. Here, students can easily commute to and from school thanks to the nearby train station along Wheeler Avenue. Access to Saw Mill River Parkway and various bus stops along Pleasantville Road provide seamless connections around town for residents, with New York City about 35 miles away.
Commuters take the Metro North train from Pleasantville into New York City.
Buses offer transit options in Pleasantville, New York.
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Written By
Lillie Duston
Photography Contributed By
Leon Cato
Video By
Tyler Hall
Interested in learning more about homes in this area?
Reach out to
Loretta Fleming Chiavetta,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Pleasantville, NY sell after 33 days on the market compared to the national average of 54 days. The median sale price for homes in Pleasantville, NY over the last 12 months is $836,500, down 14% from the median home sale price over the previous 12 months.
Welcome to this beautifully updated 2-bedroom condo in the sought-after Foxwood Complex in Pleasantville. This meticulously maintained home offers comfort, convenience, and exceptional value — with HEAT INCLUDED in the monthly common charges. Inside, you’ll find new flooring throughout, creating a fresh, modern feel from the moment you enter. The spacious layout includes a versatile bonus room
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.
Discover the perfect opportunity to live in one of Pleasantville’s most desirable communities! This charming, beautifully maintained 2-bedroom, 1.5-bathroom condo offers a fantastic layout flooded with natural light, boasting a southern exposure that keeps the home bright all day long.Step into a generously sized living room that provides a welcoming space for relaxation and entertaining. The
Welcome to Pleasantville Country Club, the golf community where luxury meets convenience in this pristine unit with walls of windows and an expansive sunny golf course view. perfectly sited on a cul-de-sac, this home offers a newly renovated (2025) spectacular open sparkling white designer kitchen with top-of-the line appliances and cabinetry, a breakfast bar and pantry storage, and gleaming
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
Sun-filled and designed for easy living, this beautifully maintained 3-bedroom, 3-bath home offers the perfect blend of comfort and versatility. A private, level fenced yard creates an ideal setting for relaxing, entertaining, or everyday enjoyment. The walk-out lower level features its own private entrance and flexible living space complete with a studio setup, kitchenette, and guest room,
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,
TIMELESS APPEAL! This stunning Colonial is the perfect blend of traditional charm and modern functionality! The spacious two storied family room/ gas fireplace is ideal for everyday living and grand entertaining. Add a banquet sized dining room...perfect for memorable feasts makes hosting the holidays a joy. Tucked away, a formal living room for quiet moments. 2 car garage with entry convenient
All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.
Welcome home! This lovely light and bright first floor two bedroom unit in the sought after Greenwood Condominium complex. Located in the Village of Pleasantville, enjoy easy access to Metro North, restaurants, entertainment, parks and the Award Winning Pleasantville School District. The unit is newly painted with refinished hardwood floors, updated kitchen and bath, ample closets and more. The
An ode to the artists and laureates steeped in the history of Pleasantville, The Atwood is nestled just a block from downtown restaurants and shops. The Atwood is an upscale boutique apartment community with a multitude of comfort and health driven amenities. Enjoy complimentary freshly ground coffee as you relax in our finely appointed lobby lounge soaking in natural light. Head downstairs to
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with sixapartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primarybathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout
Perfectly situated directly across from the train station, this home offers unmatched convenience in the center of town, placing shopping, dining, and everyday essentials just steps away. Enjoy easy access to surrounding hotspots — Tarrytown, White Plains, and a quick 50-minute train ride to New York City, making this the ideal location for commuters and explorers alike.Inside, the unit
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with sixapartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primarybathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with sixapartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primarybathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with sixapartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primarybathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with sixapartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primarybathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout
Be the first to live in this Brand New Modern - Energy Efficient- Pet friendly - Boutique rental building in the heart of Pleasantville Village with six apartments. Each apartment features 2 Bedrooms/2 Bathrooms, 2 Parking Spaces, Washer/Dryer in Unit, Radiant heated floors in primary bathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout the
This sunny, 2 BR condo has just been renovated with a decorator's eye - gorgeous, updated and freshly painted. Complete with wood flooring throughout, laundry on-site, this apartment offers great space located a stone's throw (.3 mi) from downtown Pleasantville with restaurants, shopping, library, MetroNorth train and all major highways. Don't miss this opportunity to live in this fantastic town.
Experience the best of modern living at Pleasantville Lofts! These modern custom-designed residences offer a variety of layouts ranging from studios to 3-bedroom options and provide an elevated living experience throughout every enclave. The residences offer modern industrial-style elegance with smart home keyless entry, stunning wide plank flooring, exposed beams, and in-residence Bosch washers
Anthony Calzetta-RaymondDouglas Elliman Real Estate
Welcome to 95 King St #1. If you are looking for a beautiful Apartment in a Multi Family Rental Home that is unique and charming, look no more! This spacious 3 Bedroom, 2 Bathroom home offers comfort, convenience & room to breathe. Nestled in the heart of Pleasantville, this property is perfect for those seeking tranquility without sacrificing accessibility as the home is centrally located to so
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