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

$1,500,000

4 Beds ⋅ 3 Baths ⋅ 1053161 MLS

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.

37 Pheasant Run Road, Pleasantville

$2,499,999

5 Beds ⋅ 5 Baths ⋅ 1043619 MLS

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!

26 Cecilia Lane, 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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