Pleasantville Homes with Byram Hills School district

Welcome to Pleasantville, New York—an enchanting village nestled in the heart of Westchester County. Known for its picturesque landscapes and tight-knit community, Pleasantville offers a unique blend of small-town charm and modern convenience. With its tree-lined streets, delightful shops, and vibrant dining scene, this charming locale is perfect for families, professionals, and anyone seeking a serene lifestyle just a stone's throw from the hustle and bustle of New York City.

One of the standout features of Pleasantville is its highly regarded Byram Hills School District, which consistently ranks among the top districts in the state. Families are drawn to this area not only for its excellent educational opportunities but also for the community spirit that thrives within the schools. With a commitment to academic excellence, innovative programs, and a focus on holistic development, Byram Hills nurtures the next generation of leaders.

The real estate market in Pleasantville is diverse, offering a range of homes from quaint cottages to spacious family residences. Many properties boast beautiful gardens, modern amenities, and easy access to parks and recreational facilities. Whether you're looking for a charming starter home or a luxurious estate, Pleasantville has something to suit every taste and budget.

With its rich history, vibrant community, and exceptional schools, Pleasantville is more than just a place to live—it's a place to thrive. Explore the opportunities that await you in this delightful village, and discover why it’s considered one of Westchester County’s hidden gems. Your dream home in Pleasantville is waiting!

Newest Pleasantville Homes with Byram Hills School district

$3,350,000

5 Beds ⋅ 6 Baths ⋅ 1023249 MLS

Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of thoughtfully curated living space designed for the most discerning buyer. From the moment you step inside, you're greeted by soaring ceilings, sun-filled interiors, and beautifully appointed living spaces that seamlessly blend everyday comfort with grand-scale entertaining. Every detail has been carefully considered, creating an atmosphere of refined luxury throughout. The home's versatile floor plan features five spacious bedrooms, including a desirable first-floor guest suite with a full bath—perfect for extended family, overnight guests, or a private executive home office. The spectacular primary suite is a private sanctuary unlike any other, offering a spacious bedroom retreat, expansive custom walk-in closets, and luxurious his-and-her spa-inspired bathrooms, providing the ultimate in comfort, privacy, and everyday indulgence. Designed for effortless indoor-outdoor living, the resort-style backyard is an entertainer's dream. Spend summer days relaxing beside the stunning in-ground pool and spa or host unforgettable gatherings beneath the covered patio, complete with built-in heaters, integrated speakers, and a fully equipped outdoor kitchen—allowing you to enjoy every season in style. The expansive walk-out lower level offers endless possibilities, whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, or additional living quarters. Its exceptional scale provides the flexibility to accommodate every lifestyle. Perfectly positioned in one of the area's most desirable neighborhoods, this remarkable estate is just minutes from Armonk's vibrant downtown, Metro-North, award-winning schools, fine dining, boutique shopping, parks, and convenient access to New York City.

15 Heritage Drive, Pleasantville

$1,499,000

3 Beds ⋅ 3 Baths ⋅ 1012440 MLS

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.

15 Deerfield Lane S, Pleasantville

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