Courtesy: Julia B Fee Sothebys Int. Rlty
914-295-3500
Welcome to this spacious contemporary home featuring three bedrooms and three baths, perfectly situated on a half-acre lot on a desirable cul-de-sac. Inside you'll find a bright dining room and an eat-in kitchen with a separate laundry room for added convenience. The kitchen enjoys easy outdoor access to a double deck, which is perfect for outdoor entertaining and offers a front-row seat to spectacular sunsets in a peaceful setting. The living room features vaulted ceilings and one of two wood-burning fireplaces, creating a warm and inviting space for both everyday living and entertaining. The home includes a generous primary bedroom suite with a tastefully renovated full bathroom next to two additional bedrooms that share a hall bath with a tub. The finished lower level features a spacious casual living room with a second wood burning fireplace, wet bar and built-ins, plus additional rooms for a home gym, private remote office, or recreation space as well as a renovated third full bath. All of these areas have walkout sliders to the expansive patio. A 2-car garage and a driveway that easily fits six cars completes the property. This home is located just minutes from the Pleasantville pool and the scenic trails and open space of Nannahagan Park, which is perfect for outdoor recreation and relaxation. It is also minutes from the vibrant downtown Pleasantville Village scene, offering numerous dining options, the Jacob Burns Film Center, the train station, and Saturday's Farmers Market. This home perfectly blends privacy, comfort, and convenience.
Courtesy: RE/MAX Prime Properties
914-723-1212
Welcome to a half acre of heaven. You will fall in love with the incredible landscaping and gardening that has entertained garden club members. The glorious interior is light and bright with lots of windows strategically placed for viewing the beautiful outdoors. Plus, there is additional recessed lighting. The main level consists of a gracious entry foyer and guest closet, along with a powder room. Additionally, on this level, there is the large living room with an easy gas fire plae and door to a lanai style wrap around trex deck. There is also the dining room and an eat-in-kitchen with all the accoutrements and stainless steel appliances. plus a door to the back deck and oversized patio. The second level is a short and artful staircase to the second level. Here you will find the large primary suite with beautiful bathroom and several customized closets. There are two other bedrooms on this level and a full bathroom. Enjoy the comfort of radiant floor heating in both the kitchen and primary bathroom. You will spend a lot of time on the lower level, which has a large muti-purpose room with plenty of space for an exercise area, an entertainment area, and a possible office area. You will also find a bedroom, a full bath, the laundry room, garage access, and doors to the huge back patio where you can relax--a hot tub and firepit are there for you and come with the house! The house is situated between Chappaqua and Pleasantville and provides easy access to both downtown areas, recreation, trains and highways. This is a move-in ready home you will always remember.
Courtesy: Compass Greater NY, LLC
914-228-2656
Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry, breakfast room with terrace access, formal dining room, private library, and an inviting family room with fireplace. A dramatic two-story entry foyer, generous mudroom with laundry, and attached 3-car garage complete the level. Upstairs, the luxurious primary suite is a true retreat, highlighted by a vaulted ceiling, fireplace, dressing room with island, and a spa-inspired dual bath with soaking tub and oversized shower with separate entries. Three additional ensuite bedrooms and a second laundry provide comfort and functionality. Nearly one acre of usable grounds, with town approved pool site, creates the ideal backdrop for the finest outdoor living. Next to 2026 new build by Tavo, in the Chappaqua school district. Convenient to town, schools, highways, and approximately 50 minutes to NYC. House has a 5 bedroom septic system.
Courtesy: William Raveis-New York LLC
914-967-1333
Offered for the first time in over 90 years, this cherished village home presents a rare opportunity to become part of Pleasantville’s rich community fabric. Lovingly held by the same family for generations, this 3-bedroom, 1.5-bath residence is ready for its next chapter, offering endless potential for renovation, expansion, or personalization. The home features a classic layout filled with warmth and timeless character. An expansive, level yard provides exceptional outdoor space, ideal for gardening, recreation, entertaining, or future enhancements. A detached garage adds convenience and valuable storage. Ideally located in the heart of Pleasantville, this property is surrounded by tree-lined streets and a vibrant village atmosphere. Enjoy close proximity to the Jacob Burns Film Center, the popular Pleasantville Farmers Market, local cafés, shops, and dining. Commuters will appreciate easy access to the Metro-North train and the Saw Mill River Parkway. Outdoor and recreational amenities abound nearby, including Rockefeller State Park Preserve, private tennis facilities, and a community pool. Whether restoring its original charm or creating a modern vision, this is a unique opportunity to own a piece of Pleasantville history in one of Westchester County’s most desirable communities.
Courtesy: Julia B Fee Sothebys Int. Rlty
914-295-3500
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, perfect for an in-law, au pair, extended family, or home office suite. Step outside to a charming brick patio and rear patio with new awning, creating seamless indoor-outdoor living. Thoughtful updates include freshly painted interiors on both levels (2025), new rear awning (2025), new vinyl flooring upstairs (2024), hot water heater (2024), oil tank (2021), central A/C (2021), and exterior painting (2020). Ideally located just minutes from town, train, shopping, dining, parks, and major highways, with an easy walk to the train station, this home offers both convenience and lifestyle. Additional highlights include 1-car garage and parking for four cars and a full attic for storage.
Courtesy: Key Real Estate Services, LLC
718-874-2877
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 reflects both the apartment's current wear and tear and the opportunity to create a modern home or home away from home. Outside is the leafy, walkable, convenient, and charming village of Pleasantville. Walk half a mile or less to Metro-North, bountiful shopping and dining, the renowned Jacob Burns Film Center, and a year-round weekly farmers market. Walk or drive less than a mile to Pace University's Westchester campus and two public (free) nature and recreation preserves. Drive up the street to jump on the Saw Mill River Pkwy and just a mile for easy access onto the Taconic Parkway and Rt 100. One cat or "small household pet" per unit; no dogs. Apartment can be rented with minimum one-year leases and approval; $150 fee and $500 deposit. Garage can be rented to another Greenwood Condo resident. Visitors and other residents can park in any space along the community's perimeter driveway. Current monthly Common Charge ($228.88) and ongoing monthly Capital Maintenance Assessment ($28.36) total $257.24/mth; CC includes heat and hot water. Current garage Common Charge: $31.48/mth. The common laundry is conveniently located next door. 2025 town and county taxes: $449.26; 2026 school taxes: $2,020.97; 2025 village taxes: $1,079.08.
Courtesy: Keller Williams NY Realty
914-437-6100
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. Your new home has ample closet space and stainless steel appliances so you'll have space to entertain or just relax. With lovely hardwood floors, modern updated kitchen, half bathroom (for ease of use when entertaining guests) and a dining area what more could one need (and that's only the main level)! Step down to the lower level where you will have a large bedroom with plenty of room for your furniture. With laundry in the unit and a modern full bath on the lower level you'll be in complete comfort. Located directly across from Roselle Park and close to Pleasantville with shops, restaurants and the train if you choose, you'll need to worry no more! Complete with one parking spot the possibilities for you to enjoy this lovely home are endless! Location, Location, Location!!! Make this home yours today!
Courtesy: William Raveis Real Estate
914-273-3074
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, you’ll find ample space to create lasting memories. The property features an amazing garden and a fenced outdoor area ideal for summer gatherings and outdoor enjoyment. Conveniently located near Pleasantville, Armonk, and Chappaqua, you’ll have easy access to shopping, dining & Metro North. Don’t miss your chance to own this one-of-a-kind home.
Courtesy: Houlihan Lawrence Inc.
914-238-4766
Welcome to Pleasantville Country Club where luxury meets ease and every day feels like a retreat. Perfectly positioned just steps from the tennis and pickleball courts, this sun-drenched townhome places you in the heart of one of Westchester’s most coveted lifestyle communities. Whether you’re a player, a spectator, or simply someone who enjoys the hum of an active, close-knit neighborhood, this is where you’ll feel instantly at home. Step inside to discover light cascading through walls of glass, illuminating the airy, open-concept living and dining areas. The kitchen, thoughtfully positioned to capture the morning sun, offers the perfect spot for coffee at the breakfast table as the day unfolds. Seamlessly connected to the living and dining spaces, the main level opens to an expansive deck, an entertainer’s dream where summer barbecues stretch into starlit evenings and lazy Sunday brunches overlook golfers teeing off in the distance. Upstairs, the primary suite serves as a serene sanctuary, featuring a spa-inspired bath with soaking tub, separate glass-enclosed shower, and generous walk-in closets. A secondary bedroom and hall bath provide comfort and privacy for family or guests, all bathed in gentle natural light. The lower level extends the home’s lifestyle versatility with space ideal for game nights, a fitness studio, or festive gatherings, complete with a full bath and sliding doors that open to a secluded patio. Picture mornings spent reading among hydrangeas or quiet evenings unwinding beneath a canopy of twilight. Life here is as effortless as it is exceptional. Weekends drift by poolside, meals arrive from the seasonal restaurant, and celebrations unfold under endless summer skies. The pickleball and tennis courts are just a stroll away, the pro shop stands ready to outfit your next round, and the fitness center beckons for early workouts before a leisurely afternoon on the golf course. When you crave a change of scenery, the charm of Pleasantville Village awaits just beyond the gates. Saturday mornings at the Farmers Market, evening screenings at the Jacob Burns Film Center, dinner at your favorite local restaurant, and when the city calls, an easy train ride delivers you to Manhattan in under an hour. Here, every detail is designed for comfort, connection, and the simple joy of everyday living, a rare offering where resort-style amenities and village convenience meet in perfect harmony.
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.
