Courtesy: ERA Insite Realty Services
914-769-2222
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 backyard provides plenty of room for outdoor entertaining, play, gardening, or simply relaxing. A wonderful opportunity to enjoy the best of Pleasantville living in a convenient, walkable location
Courtesy: Compass Greater NY, LLC
914-327-2777
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 main level effortlessly connects bright, expansive gathering spaces to a magnificent rear deck and backyard oasis complete with a custom stone fireplace. Upstairs features spacious bedrooms, including a primary suite with a steam shower and a generous walk-in closet. The home also offers a dedicated office, two-car attached garage, warm fireplace accents, and a flexible lower level ideal for guest accommodations or recreation, all located within the Byram Hills School District and just minutes from Pleasantville village, the Metro-North train, local shops, and major commuting routes.
Courtesy: Julia B Fee Sothebys Int. Rlty
914-725-3305
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 the rare option to choose between the award-winning Byram Hills or Chappaqua school districts. A gracious foyer sets the tone, opening to living spaces designed for comfortable daily activities and effortless entertaining. The living room opens through sliding glass doors to an expansive bluestone patio, blurring the line between indoor and out against a backdrop of lush private grounds. The formal dining room flows seamlessly into a sun-filled eat-in kitchen, which opens directly to the patio for easy indoor-outdoor dining and gathering. At the heart of the home is a dramatic family room with vaulted ceilings, anchored by a wood-burning fireplace and framed by an abundance of windows overlooking the surrounding landscape. Warm, inviting and filled with natural light, it is an ideal gathering space in every season. A private bedroom wing places all five bedrooms conveniently on the main level. The serene primary suite features generous walk-in closets and an en-suite bathroom while three additional well-proportioned bedrooms share an oversized hall bathroom. A fifth bedroom adds flexibility as a guest suite or home office. A beautifully appointed powder room, an oversized mudroom with laundry, along with direct access to the attached two-car garage round out the main level with everyday luxury and convenience. The home’s impressive scale continues upstairs, where a versatile loft and full bathroom offer abundant space for recreation, work, fitness or guests. The finished walkout lower level offers additional flexibility, complete with its own powder room and direct access to the backyard. Outside, the expansive lawn, established perennial gardens, mature trees and thriving vegetable garden create a private park-like setting with abundant room to relax, play, garden and entertain. Set in a peaceful, sought-after neighborhood, this home is close to the North White Plains and Pleasantville train stations, the Pleasantville Farmers Market, Jacob Burns Film Center, and shopping in both Armonk and Chappaqua. Rare in its scale, light, privacy and flexibility, 26 Cecilia Lane delivers a turnkey offering of elegance and expansive outdoor living in one of Westchester's most prime locations. VERY ATTRACTIVE TAXES!
Courtesy: Compass Greater NY, LLC
914-238-0676
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 the home a collected, design forward feel. The formal dining room makes a memorable first impression, while the renovated kitchen mixes soft gray cabinetry, graphic flooring and a substantial center island. The adjoining living room is bright and comfortable, with direct access to the patio and fenced backyard. An oversized garage offers tremendous potential for a workshop, studio, gym or additional storage, while the generous driveway provides parking for multiple cars. Outside, the patio and fenced yard extend the living space with room for dinner, a garden or a quiet afternoon at home. This is an exceptional entry point into Pleasantville and the lifestyle that comes with it. Walk into the village for coffee, dinner or a show. Spend Saturday morning at the farmers market. Walk to Metro North for the commute into Manhattan, or enjoy the dog park, parades, festivals and community events throughout the year. There is an extraordinary amount of life packed into this 1.8 square mile village, and 3 Elm Street puts you right in the heart of it. This is a home that makes it remarkably easy to become part of the community around it.
Courtesy: Coldwell Banker Realty
914-245-3400
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, bringing additional natural light and an open, airy feel to the space. The partially finished basement provides additional flexible space and was previously used as a home office, with additional areas available for storage and other needs. Outside, the two-parcel setting provides additional outdoor space to enjoy, along with ample parking. Located adjacent to Graham Hills Park, the home offers convenient access to outdoor recreation while remaining just minutes from the Pleasantville Metro-North station, downtown Pleasantville, shopping, dining, and major roadways. With its tranquil setting, hardwood floors, charming architectural details, extended living room, flexible lower-level space, ample parking, two-parcel property, and convenient location, 82 Birch Drive offers a wonderful combination of character, space, and convenience.
Courtesy: ERA Insite Realty Services
914-769-2222
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 popular Jacob Burns Film Center. A wonderful selection of restaurants, shops, and community amenities are all just moments away. With its inviting living spaces and unbeatable location, this home is a fantastic opportunity to enjoy all that Pleasantville has to offer!
Courtesy: Howard Hanna Rand Realty
914-769-3584
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 Bath, Walk-in Closet and a 2nd Bedroom with sliding doors, closet. A true diamond in the rough. The property is being offered in its present condition. With the right vision, this home presents an opportunity to create a home tailored to your style in a sought after location. Heat and hot water are included in the common charges, along with full landscaping and snow removal. Amenities include 3 swimming pools, village tennis courts and playground. Foxwood is just minutes from everything Pleasantville has to offer, from Jacob Burns Film Center, to Saturday's Farmers' Market, to shopping, Restaurants, Metro north train and major highways.
Courtesy: RE/MAX Town & Country
845-765-6128
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 plenty of space for casual dining. Just off the dining area, step onto your private covered balcony overlooking the beautifully maintained community grounds an ideal spot to enjoy your morning coffee or unwind after a long day. Back inside, you'll find a spacious living room filled with natural light, a convenient in-unit washer and dryer, a beautiful full bathroom and a generously sized bedroom featuring a ceiling fan and a large walk-in closet. Additional highlights include a secure private storage area. Common charges include heat, hot water, landscaping, snow removal, Tennis or Pickleball courts and access to three community swimming pools. Perfectly situated in the heart of Pleasantville, Foxwood is just minutes from the Jacob Burns Film Center, the renowned Pleasantville Farmers Market, shopping, dining, parks, and recreation. Commuters will appreciate being just 1.4 miles from the Metro-North train station, offering an easy commute to New York City, along with quick access to major highways. Enjoy the best of Central Westchester living where everything is close and convenience meets comfort.
Courtesy: Howard Hanna Rand Realty
914-328-0333
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, Metro-North, downtown shopping and dining, the Jacob Burns Film Center, Pleasantville Farmers Market, parks and recreation. With the train, schools and vibrant Village center all nearby, everyday errands, commuting and enjoying the community couldn’t be easier. A great starter home in one of Westchester’s most desirable and welcoming villages—bring your vision and make 1 Brentwood Drive your own.
Courtesy: Howard Hanna Rand Realty
914-769-3584
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 front porch. It’s the kind of porch that makes you want to slow down, sit for a while, and enjoy the company of friends. Use it as a place to entertain, read the newspaper, enjoy your morning coffee, or simply relax. It truly feels like a second living room and adds so much to the personality of this home. The house has been recognized for its charm and has even been featured on Pleasantville home tours. There’s also plenty of opportunity to make the home work for your needs. The attic space could potentially be transformed into a primary bedroom suite, home office, study, playroom, or whatever space your wishes desire. You’re just blocks from Bedford Road Elementary, the library, the middle and high schools, and both uptown and downtown Pleasantville. Stroll to town for dinner, grab a coffee, browse the shops, catch a movie at the coveted Jacob Burn’s theatre or enjoy the many community events that make Pleasantville such a great place to live. The Metro-North station is also right in town making the commute to New York City and White Plains super convenient. For those who love the outdoors, Rockefeller State Park Preserve, Opperman’s Pond, the amazing Pleasantville town pool and other nearby parks offer beautiful places to walk, hike, and enjoy nature. The Pleasantville Music Festival and frequent town concerts contribute to the cultural elements that make this town one of a kind. This is a home with personality, history, and possibilities. You can move right in and enjoy it as it is or take advantage of the additional space and make it your own. If you’ve been looking for a home that feels welcoming the minute you arrive—and a community where you can truly put down roots—this Pleasantville Craftsman is a must see!
Courtesy: Coldwell Banker Realty
914-997-0097
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 with stone trim. At the opposite end of the room is a huge picture window with expansive views of the glorious outdoors. Also on this level is a generously-proportioned master bedroom with custom woodwork and 4 windows that allow in natural light and views of the unspoiled park land located directly in front of this home. Three additional bedrooms are also on this level, one of which is currently used as an office. Step downstairs to a remodeled kitchen with a pocket door to a large, clean all-purpose room. Doors from this room and the kitchen lead out to an expansive stone patio with views over the property and out to the street. Guests can transition easily from the all-purpose room to the patio. Custom woodwork and built-ins are evident throughout this home, as well as upgraded lighting, shed ceilings and other notable features which give it a unique, eclectic style. Once outdoors, the large property lends itself to privacy, and yet there is ample room for gardening, for fur babies to roam and for relaxation and basking in the sun. Everything is here to conveniently work from home. However this home's proximity to the Pleasantville Metro-North Station makes commuting to New York City an equally desirable option. This home must be seen in person to be appreciated!
Courtesy: William Raveis Real Estate
914-273-3074
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 breakfast bar, along with beautiful hardwood floors throughout. A detached one-car garage provides covered parking and additional storage. The location is hard to beat! Just steps from the Metro-North train station, Farmers Market, Jacob Burns Film Center, schools, shops, restaurants, and all that the Village of Pleasantville has to offer. Whether you're a first-time buyer, downsizing, or simply looking for a home that makes everyday life easier, this is easy living in an unbeatable village location.
Courtesy: Keller Williams Realty Group
914-713-3270
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 Bedford Road School, and 0.3 miles to both the Middle and High Schools, this home delivers effortless access to every part of town. Shops, dining, parks, the Farmers Market, and the Jacob Burns Film Center are all moments away, with easy ON/OFF access to the Saw Mill River Parkway for seamless commuting. County Tax classification code is R-02, the ground-floor unit is a standout feature — ideal as a professional home office (light business permitted) or as a 750 sq ft above ground living space. Previously used as a real estate office, it now functions as a comfortable residential space with endless potential with private entrance and second egress. . The main 3-bedroom apartment offers classic warmth and modern convenience, featuring a chef’s stove, EI kitchen w. SGD onto patio, formal dining room, sun room and living room. The second floor offers f primary bedroom, and two additional secondary bedrooms . The home has been fairly well maintained and is ready for you to personalize and make your own. This home offers off-street parking for at least three vehicles. With flexible zoning, walk-to-everything convenience, and timeless 1930’s character, 4 Depew Street is a one-of-a-kind Pleasantville opportunity. Zoning allows for 6 foot signage that is visible from Saw Mill River Parkway. .
Courtesy: Houlihan Lawrence Inc.
914-238-4766
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 appliances, and abundant counter space. Entertain with ease in the living room, accented by a cozy fireplace, or step out onto the spacious screened porch overlooking the 3rd green of the nine-hole golf course. Upstairs, the expansive primary suite offers a luxurious en-suite bath and generous closet space, accompanied by two additional bedrooms and a full hall bath. The lower level is an entertainer’s dream, featuring a bright, light-filled family room with a wall of doors opening to a beautifully landscaped private patio. This level also includes ample storage, a full bath, and French doors leading to a versatile space perfect for a guest room or private home office. Beyond the home, step out and enjoy the incredible community amenities, including a swimming pool, tennis and pickleball courts, workout facilities, and an on-site restaurant. With close proximity to the vibrant village of Pleasantville, this isn't just a home—it's a lifestyle waiting to be lived!
Courtesy: Houlihan Lawrence Inc.
914-762-7200
Enjoy the best of Westchester living with a Pleasantville address in the highly sought-after Byram Hills School District. Just minutes from the Pleasantville Farmers Market, Jacob Burns Film Center, downtown Armonk, Chappaqua shopping, dining, and Metro-North, this beautifully updated ranch offers the perfect blend of convenience, privacy, and one-level living. The open-concept floor plan features hardwood floors, a stone fireplace, and a renovated eat-in kitchen with granite countertops, stainless steel appliances, custom cabinetry, and built-in seating. A stunning great room/tv room with 12-foot beamed ceilings, skylights, and sliding doors opens to an expansive deck, creating seamless indoor-outdoor living. The resort-style backyard is a private retreat with a heated saltwater pool (2021), new hot tub (2025), and mature landscaping. The primary suite offers a walk-in closet, radiant heated bath floors, and peaceful woodland views. Additional bedrooms, updated baths, a home office/library, laundry area, and a finished lower-level recreation space provide flexibility for today's lifestyle. Complete with a two-car attached garage and easy access to major commuting routes and the Pleasantville Metro-North station, this exceptional home delivers luxury, comfort, and convenience in one of Northern Westchester's most desirable locations.
Pleasantville is located in New York. Pleasantville, New York has a population of 7,469. Pleasantville is more family-centric than the surrounding county with 42.99% of the households containing married families with children. The county average for households married with children is 35.32%.
The median household income in Pleasantville, New York is $165,987. The median household income for the surrounding county is $105,387 compared to the national median of $69,021. The median age of people living in Pleasantville is 40.2 years.
The average high temperature in July is 80.9 degrees, with an average low temperature in January of 18.3 degrees. The average rainfall is approximately 49.9 inches per year, with 29.7 inches of snow per year.
