$958,626Average Value$468Average Price per Sq Ft10Homes 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
Frederick Cindrich,
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 39 days on the market compared to the national average of 58 days. The median sale price for homes in Pleasantville, NY over the last 12 months is $845,000, down 9% from the median home sale price over the previous 12 months.
Enjoy the best of village living in this beautifully updated one-bedroom co-op, ideally situated in the heart of Pleasantville. Just moments from the park, local shops, and Metro-North, the location offers unmatched convenience for both daily living and commuting. The open-concept kitchen is thoughtfully updated with warm wood cabinetry, granite countertops, stainless steel appliances, and a tile
Welcome to 119 Manville Road — a beautifully maintained 4-bedroom, 2-bath split level on a peaceful dead-end street in Pleasantville, freshly painted throughout and ready to welcome its new owners. The updated kitchen features quartz countertops and stainless steel appliances, while hardwood and carpeted floors run seamlessly through the home. Central A/C, an included washer/dryer, and a 1-car
Stunning four-bedroom Village Victorian in the heart of Pleasantville, rich with late 1800s character and timeless architectural detail. This exceptional home showcases exquisite original features including ornate crown molding, soaring 10-foot ceilings, bay windows, hardwood floors, and a beautifully crafted wood banister spanning all three levels. The first floor offers a gracious and welcoming
Beautifully maintained 3-bedroom, 2 full bath raised ranch offering an open and airy floor plan, perfectly situated on a quiet cul-de-sac in a highly desirable location. This inviting home features spacious living areas filled with natural light, ideal for both everyday living and entertaining. Enjoy the convenience of being within walking distance to both the charming villages of Chappaqua and
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,
Welcome to 294 Bedford Road - this enchanting antique home, built in 1902, is nestled in the heart of Pleasantville. With a prime in-town location just half a mile from the train station, you’ll enjoy the perfect blend of historic charm and modern convenience. This 5-bedroom gem boasts a classic front porch that invites you to sit back and relax while sipping your morning coffee. The spacious
Welcome to Pleasantville! This beautifully maintained 3-bedroom, 2-bathroom home offers space, comfort, and exceptional value in a picturesque setting. Step into a light-filled living room featuring an oversized bay window that creates a warm and inviting atmosphere. The space flows seamlessly into a formal dining area, perfect for entertaining and everyday gatherings. Glass sliders open to a
Welcome to this truly stunning residence in Pocantico Hills, where timeless design meets modern updates-all complemented by remarkably low taxes. This exceptional home features four spacious bedrooms and four full baths, including a brand-new roof (January 2024) and a newly painted chef’s kitchen designed for both function and style.At the heart of the home is the breathtaking Great Room,
Excellent investment or owner-occupant opportunity in the heart of Pleasantville! This well-maintained multi-family property features three apartments, including one 3-bedroom unit and two 2-bedroom units—ideal for generating steady rental income.Each unit offers 1 full bathroom, a functional layout, and great natural light throughout. The 2-bedroom apartments located on the second and third
Looking to immerse yourself in the vibrant Pleasantville community? Don’t miss this rare opportunity to own a beautifully updated village home just steps from the award-winning Bedford Road Elementary School. This charming, light-filled residence offers 3 spacious bedrooms and 2.5 bathrooms, with thoughtful updates, abundant storage, and flexible living spaces throughout. The eat-in kitchen and
Welcome to 20 Robbins Road—perfectly set on a quiet cul-de-sac on a half-acre with a fenced in backyard in one of Westchester’s most desirable communities. Step inside to an inviting living and dining area where oversized windows and a cathedral ceiling with skylight fill the space with natural light. A cut-stone fireplace, recessed lighting, and oak floors create a warm, stylish setting for
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.
Spacious rental of a raised ranch home with an open and inviting main level floor plan. The updated kitchen features granite countertops and opens to a formal dining room, ideal for entertaining. The expansive family room showcases a cathedral beamed ceiling and door leading to a newly installed travertine stone patio and level, private yard. The rental also includes a portion of the lower level,
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
Modern, and bright two-bedroom apartment in the center of Pleasantville across the street from the train station- corner of Bedford Rd and Memorial Plaza. The apartment is 1150 square feet, on the second floor of a 4-apartment building. It has 2 bedrooms, living room with fireplace, modern kitchen with dishwasher and a large bathroom. It is in excellent condition, with 9-foot high ceilings, lots
Cute, bright, and spacious 1-bedroom plus den apartment on the second floor of a two-family home.Private front entrance with porch access. Includes new bedroom carpet, 1 full bathroom, in-unit washer/dryer, and access to the lawn and garden.Located in a quiet neighborhood on a sidewalk, with easy access to village shops, Metro-North, and parks.Included: Heat, water, and
Newly Renovated 2BR Apartment Be the first to live in this newly renovated 2 bedroom, 1 bath second-floor apartment in the heart of Pleasantville! Apartment Features: 2 comfortable bedrooms with good closet space 1 modern, updated bathroom Stainless steel appliances Dishwasher – no more washing dishes by hand In-unit washer & dryer – real convenience Central A/C – stay cool all summer Bright
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, Washer/Dryer in Unit, Radiant heated floors in primary bathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout the kitchen and baths,
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, Washer/Dryer in Unit, Radiant heated floors in primary bathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout the kitchen and baths,
Unpack and enjoy life in this immaculately maintained 3BR, RR on a cul-de-sac.Home features new state of the art furnace, new washer/dryer, private deck and side yard.
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, Washer/Dryer in Unit, Radiant heated floors in primary bathroom, Heated toilet seats, Smart Thermostat, LED Under cabinet lighting, Quartz Countertops throughout the kitchen and baths,
This distinctive four-bedroom, four-bath home in the Heart of Pocantico Hills features a New roof (January 2024), Brand New Primary Bath (January 2026). The chef’s kitchen opens to a captivating Great Room, highlighted by exquisite woodwork and soaring vaulted ceilings—a stunning centerpiece for entertaining or relaxing. The main floor also includes a sun-filled home office, a screened-in porch,
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