Pleasantville Homes for Sale

Welcome to Pleasantville, New York—an enchanting village nestled in the heart of Westchester County. This charming community is renowned for its picturesque landscapes, vibrant downtown, and a strong sense of community, making it one of the most desirable places to call home in the Hudson Valley.

Pleasantville boasts a rich history and a quaint, small-town atmosphere, complemented by modern amenities. Residents enjoy a variety of local shops, cozy cafes, and fine dining options, all within walking distance. The village is also home to several parks and recreational facilities, providing ample opportunities for outdoor activities and family fun. With its excellent schools and family-friendly environment, Pleasantville is an ideal location for families looking to settle down.

When it comes to real estate, Pleasantville offers a diverse selection of homes for sale, catering to various tastes and budgets. From charming Victorian homes and modern townhouses to spacious single-family residences, there’s something for everyone. Many properties feature beautifully landscaped yards, updated interiors, and proximity to local parks and schools, ensuring a perfect blend of comfort and convenience.

The real estate market in Pleasantville is thriving, with homes that not only provide a sanctuary but also represent a sound investment in a community that values quality of life. Whether you’re a first-time homebuyer or looking to upgrade, Pleasantville is ready to welcome you with open arms. Explore the available homes for sale today and discover the unique charm that makes Pleasantville a truly special place to live!

Newest Pleasantville Homes for Sale

$639,000

3 Beds ⋅ 1 Baths ⋅ 1048822 MLS

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.

1 Brentwood Drive, Pleasantville

$1,225,000

4 Beds ⋅ 2 Baths ⋅ 1048225 MLS

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!

1 Grandview Circle, Pleasantville

$350,000

5 Beds ⋅ 3 Baths ⋅ NJAC2026578 MLS

Very spacious home in good location easy access to shopping, public transportation and shore points. This is a 5 bedroom with office or 6 bedroom your choice. Enter into the living room with the view of the dining room. The kitchen is big enough for a small table. Lower level has a full bathroom, another bedroom and family room. Upper level all with good size bedrooms and 2 more full baths.The property is being sold in as -is condition. Loads of potential with this property. 1st floor AC does not work. Lower and Upper AC does work.

717 New Maple Rd, Pleasantville

$724,900

4 Beds ⋅ 1 Baths ⋅ 1047856 MLS

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!

45 Leroy Street, Pleasantville

$1,300,000

3 Beds ⋅ 4 Baths ⋅ 1042845 MLS

Enjoy this beautifully updated, and stylishly appointed, corner unit home in the highly desirable Pleasantville Country Club community. You will appreciate the ease of a maintenance-free, resort-style living, where you can spend more time enjoying the wonderful amenities and less time worrying about upkeep. Offering three levels of spacious living, the home welcomes you with a dramatic two-story entryway leading to inviting living and dining rooms. The main level also features a comfortable family room with fireplace and an open kitchen with a sunny breakfast nook complete with built-in banquette seating. Sliders leading to a private deck overlooking the 6th hole of this beautiful golf course and a powder room finish off the main floor. The second floor offers a primary bedroom with ensuite bath and WIC, a second bedroom with an ensuite bath, along with a flexible office space or third bedroom featuring custom built-ins, ideal for working from home. The finished lower level provides a full bath and an expansive recreation room with sliders leading to a lower patio, creating additional space for entertaining, relaxing or enjoying the peaceful golf course setting. For added convenience and ease of living, the home includes an elevator and a two-car garage. Residents of the Pleasantville Country Club enjoy a well manicured property framed by perennial gardens and exceptional amenities including a golf course, tennis/pickleball, pool and clubhouse, all while enjoying a truly easy and convenient lifestyle. Additionally, this home is in the award winning Pleasantville school district and residents can enjoy the Farmers Market, Jacob Burns Theater, restaurants, shops and all that the charming village has to offer.

29 Country Club Lane, Pleasantville

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 1042508 MLS

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!

35 Grandview Avenue, Pleasantville

$249,900

4 Beds ⋅ 2 Baths ⋅ NJAC2026502 MLS

This 3-story home has a lot of character and space for a large family. However, it needs restoration and a good clean-out. It has 4 large bedrooms, with the master suite located on the 3rd floor. The master bedroom is huge, with a full en suite, cedarwood walk-in closet, outside entrance to the backyard, and a wood-burning fireplace. The 2nd floor has 3 large bedrooms and a sitting room/den/office. The 1st floor has a large kitchen, dining room, living room, covered front porch, and a wood-burning fireplace. Off-street parking and a 2-car detached garage are included. It also has a full basement with inside and outside entrances. If you are willing to restore this historic home, then call now to schedule your showing!

8 N 2nd St, Pleasantville

$359,900

4 Beds ⋅ 3 Baths ⋅ NJAC2026424 MLS

WOW! Check out this Beautifully done, completely renovated & updated 4-bedroom, 3-full bathroom home offering an open, flexible living space!Let's start upstairs, where you’ll find one large bedroom, a full bath with eye-popping tile work and fixtures, in addition to an open area perfect for a home office, playroom, guest space, or make the entire second floor YOUR personal oasis or even an In-Law Suite, that's the greatness of it. Now the main level; We have two more perfect sized bedrooms for the kiddos, another full bathroom with eye-popping tile work and radiant fixtures. Then we go into an amazing kitchen with a granite waterfall countertop, all stainless-steel appliances, eye catching tile backsplash, and stunning fixtures. The master bedroom is located perfectly for privacy and has its own full bathroom laden with beautiful tile work and gorgeous fixtures. Now to the basement; amazing marble tile floors, hook-ups for washer/dryer, tremendous storage area, outside access to rear yard and access to the one car garage that has its own, oversized workshop area or possible home gym area. All of this beautifully crafted, fully renovated, updated, modern living feel will be yours, so what are you waiting for!

114 S Chester Ave, Pleasantville

$879,000

3 Beds ⋅ 2 Baths ⋅ 1043937 MLS

Beautifully maintained and lovingly cared for, this inviting home is nestled on a private cul-de-sac and offers a true sense of sanctuary. The main level is filled with natural sunlight from large windows and two sliding glass doors, creating a warm and welcoming atmosphere throughout. The spacious living room features sliding glass doors leading to an expansive deck, seamlessly connecting the indoor and outdoor living spaces. The deck opens directly to both the kitchen and living room, making entertaining a breeze. The elegant dining room is highlighted by a picturesque bay window, while the eat-in kitchen offers granite countertops, stainless steel appliances, and sliding doors providing easy access to the deck. Three generously sized bedrooms, each with ample closet space, and a beautifully appointed full bathroom complete the main level. The finished lower level adds even more living and entertaining space, featuring a large family room with a stunning floor-to-ceiling stone fireplace and sliding glass doors leading to a covered patio. This private outdoor retreat is perfect for summer gatherings or relaxing with a favorite drink and watching TV—even on a rainy day. A versatile bonus room, ideal as a office, den or guest space, offers generous closet space, with an additional full bathroom conveniently located nearby. The fenced-in backyard provides added privacy and completes this wonderful outdoor setting. With a one-car attached garage and convenient nearby school bus pickup, this home is truly move-in ready. Simply unpack, settle in, and enjoy! Notable items: Driveway can hold 5 cars in addition to one car garage, school bus pickup steps from home, 6 zone built in ceiling speakers with Bluetooth easy connect lets you enjoy different music in different rooms or join them all together lastly, all light switches are smart so you can program them with your phone. A true delight!

3 Douglas Drive, Pleasantville

$258,000

2 Beds ⋅ 2 Baths ⋅ NJAC2025750 MLS

Charming Single-Story Living on a Spacious Corner Lot! Welcome home to 815 Broad Street, a bright and inviting 2-bedroom, 1.5-bathroom single-family ranch offering low-maintenance single-level living. Situated on a prime 5,000+ sq. ft. corner lot, this move-in-ready home features a functional open flow across 915 sq. ft. of comfortable interior space. Step inside to resilient vinyl flooring, bright natural light, and a cozy main living area perfect for everyday relaxing or entertaining. The kitchen comes fully equipped with a gas stove and refrigerator, paired with convenient main-level half and full bath access. Central air conditioning and forced-air natural gas heating keep you comfortable year-round. Enjoy a fully fenced, oversized yard — ideal for kids, pets, gardening, or outdoor gatherings. Situated steps from South Main Street, public transit options, and quick access to major commuting routes heading into Atlantic City and nearby shore points. Whether you're a first-time homebuyer, looking to downsize, or searching for a turnkey investment property, this charming home is a must-see! Schedule your tour today!

815 Broad St, Pleasantville

$925,000

3 Beds ⋅ 2 Baths ⋅ 1027975 MLS

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. .

4 Depew Street, Pleasantville

$359,900

4 Beds ⋅ 2 Baths ⋅ NJAC2025674 MLS

Welcome home to 220 N 1st Street! This fully renovated, move-in-ready 4-bedroom, 2-full-bath residence offers seamless modern living in the heart of Pleasantville. Key Updates & Highlights: Chef-Inspired Kitchen: Brand-new cabinetry, sleek counter surfaces, and stainless steel appliances. Major Upgrades: Brand-new roof, updated HVAC system, and newly installed washer & dryer. Layout & Living: Generous 1,917 sq. ft. layout featuring a convenient primary bedroom on the main level and stylish vinyl flooring throughout. Outdoor & Extras: Spacious fenced yard with a deck ideal for entertaining, plus a versatile detached 1-car garage. Pack your bags and move right in—this turnkey opportunity is ready for immediate occupancy!

220 N First St, Pleasantville

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