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

$260,500

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

$999,000

3 Beds ⋅ 2 Baths ⋅ 1027975 MLS

ATTEENTION 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

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 1013140 MLS

Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living. Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living room stretches the full width of the home and is bathed in natural light from eastern, southern, and western exposures. A wood-burning fireplace serves as a warm focal point, while a wall of windows showcases picturesque views of mature trees, a tranquil pond, and abundant wildlife. The formal dining room is perfectly suited for both holiday entertaining and intimate gatherings. The spacious eat-in kitchen, complete with two pantries, provides direct access to an expansive deck—ideal for outdoor dining—and the attached two-car garage. A convenient powder room completes the main level. Upstairs, you’ll find a gracious primary suite, three additional bedrooms, and a beautifully renovated full hall bath. The lower level offers remarkable versatility, featuring a welcoming family room with a fireplace, as well as a workshop, laundry area, ample storage space and more. Wood floors, crown molding, central air-conditioning and an oversized two car garage are just some of the special features you will enjoy. The grounds are truly extraordinary, highlighted by exquisite stonework, garden beds, and meticulously maintained landscaping. The backyard invites out door fun, recreation and relaxation, while serene water views create a breathtaking natural backdrop. This stately home boarders scenic Opperman's Pond, where all-season activities from fishing and birdwatching to ice skating - can be enjoyed. This exceptional property is more than a home—it will be your sanctuary offering comfort, beauty, and memories.

1 Woodland Drive, Pleasantville

$369,900

4 Beds ⋅ 2 Baths ⋅ NJAC2025674 MLS

This fully renovated, move-in ready home in the heart of Pleasantville boasts 4 bedrooms, 2 full bathrooms, and modern style throughout. Recently upgraded with a new roof, HVAC system, brand-new kitchen with stainless steel appliances, and a new washer and dryer, this home offers both comfort and convenience. Complete with a detached garage and ready for immediate occupancy, this exceptional opportunity is one you won't want to miss!

220 N First St, Pleasantville

$689,000

3 Beds ⋅ 2 Baths ⋅ 1025216 MLS

Welcome to 660 Washington Avenue, a ranch-style home offering the ease of single-level living with the added benefit of flexible lower-level space. The main level features a sun-filled living room, dining area, eat-in kitchen, three comfortable bedrooms, and an updated full bath with radiant heated floors. Large windows throughout the home fill the interior with natural light and create a warm, inviting atmosphere. The walk-out lower level significantly expands the home's functionality, offering a spacious recreation area with direct access to the backyard patio, along with a private bedroom and full bath. This separate living area is ideal for extended family, in-laws, a live-in nanny, guests, or anyone seeking additional privacy and independence. Laundry, storage, and utility areas complete the lower level. Set on a beautifully landscaped property with mature trees providing privacy and shade, the home has been freshly painted and benefits from a newer furnace, heat pump, and HVAC system installed in 2021. Located just a short stroll from Chappaqua's train station, library, farmers market, downtown shops, restaurants, and community amenities, this home offers an exceptional combination of comfort, convenience, and versatility. Whether you're a first-time buyer, downsizing, or looking for a home with multi-generational living potential, 660 Washington Avenue presents a wonderful opportunity in one of Westchester County's most desirable communities.

660 Washington Avenue, Pleasantville

$1,399,000

3 Beds ⋅ 4 Baths ⋅ 1018220 MLS

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!

18 Brookview Drive, Pleasantville

$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

$323,000

3 Beds ⋅ 3 Baths ⋅ NJAC2025062 MLS

Welcome to 224 S Chester Ave, a fully updated property situated in Pleasantville, NJ. This single-family detached two-story home has been completely renovated. Enter from the sidewalk to an inviting front porch into a bright, spacious living area, open to the dining room. The renovated kitchen includes a passthrough to the dining area, and utility room including laundry. The open dining room includes a full bathroom. For optimal comfort and energy efficiency, the home features a mini-split cooling system on the open first floor. Access the full-fenced back yard through the kitchen entrance. Enjoy Lake Bay views from the private back porch. Upstairs, you will find three bedrooms and two full bathrooms. The primary bedroom suite serves as a scenic retreat, including views of the Atlantic City skyline and the bay. Plenty of street parking is available, in addition to the private driveway and detached garage. This turn-key opportunity will be delivered tenant-occupied, making it an excellent opportunity for immediate cash-flow. Easy access to public transit - bus stops are within .25 miles.

224 S Chester Ave, Pleasantville

$459,000

3 Beds ⋅ 2 Baths ⋅ NJAC2024528 MLS

Stunning custom home just steps from the beach at Lakes Bay and a short drive to Atlantic City and the barrier island beaches and boardwalk.This beauty offers breathtaking panoramic water views and an unbeatable central location in Egg Harbor Township with convenient access toschools, shopping, dining, and shore attractions. This beautifully maintained home features a private backyard setting with mature hedging,sprinkler system, and enclosed outdoor shower—perfect for enjoying coastal living. Inside, oak flooring and staircases, casement windows, andskylights fill the home with natural light and timeless character. The welcoming foyer leads to a spacious first floor featuring a comfortable livingroom, dining area, and functional kitchen layout ideal for everyday living and entertaining. This level also offers two bedrooms, a full bath, and ahuge utility/laundry room providing exceptional storage and functionality. Upstairs, a unique, huge 27x14 second-floor den with wet bar opensinto an impressive living space featuring vaulted ceilings, ceiling fans, custom lighting, and dramatic double sliders leading to an enormous deckwith stunning water views, refreshing breezes, and incredible outdoor entertaining space. The second-floor primary suite offers soaring 10-footceilings, dual closets, and an oversized storage closet for added convenience. Additional highlights include a large concrete driveway and patio,beautifully designed outdoor spaces, and a rare opportunity to enjoy shore living with comfort, privacy, and spectacular scenery.

207 E Plaza Pl, Pleasantville

$674,000

5 Beds ⋅ 5 Baths ⋅ NJAC2024208 MLS

Rare Waterfront Opportunity at 333 Oakland Ave—offered at a fraction of the cost of the island! This direct waterfront estate, featuring distinct Mediterranean stylings, is situated on a sprawling half-acre lot with an incredible 233 feet of bulkhead and rip-rap. From your back door, enjoy a view that is quite simply breathtaking, offering a panoramic sweep of the glistening bay, serene marshlands, and the iconic Atlantic City Skyline. This 2,500 sq. ft. home features 5 spacious bedrooms and 5 full bathrooms, including multiple en-suite arrangements. The main level is designed to invite the beauty of the coast inside, with hardwood flooring throughout and a gourmet kitchen with a center island that opens into a grand living, dining, and sitting area—all framed by floor-to-ceiling vistas of the water. Outside, a 1-car garage and two separate driveways provide ultimate flexibility with ample room to store a boat, an RV, or provide overflow parking for guests. For the boater, the property sits on navigable water with a dock (in need of repair) that provides the foundation for private boat slips, plus a full-service marina located just a few hundred feet away. Take in the scenery from the expansive first-floor patio or the private second-floor deck, both offering front-row seats to the most impressive sunrises and sunsets on the coast. Relax to the gentle lapping of waves and the call of seagulls in your own private sanctuary. While the home needs some TLC, the Mediterranean-inspired architecture and massive footprint are irreplaceable. With nearly 250 feet of water frontage and a premier lot, the opportunities to renovate or reimagine this into a world-class estate are truly endless. Bring your vision and anchor your future at this waterfront gem—where every morning and evening is a masterpiece! Must see!

333 Oakland Ave, Pleasantville

$374,900

4 Beds ⋅ 3 Baths ⋅ NJAC2023416 MLS

Discover this spacious 4-bedroom, 3-bath split-level home offering comfort, versatility, and plenty of room to grow! The main level features a bright, open living room and dining room combination, perfect for entertaining, along with a well-sized kitchen ready for your personal touch. All bedrooms are generously sized, including a primary bedroom with a walk-in closet. The lower level includes a family room, an additional bedroom, and a full bath, making it an ideal setup for extended family or in-law living. Enjoy ample attic storage, newer central air, and a large yard with endless possibilities for outdoor living, gardening, or entertaining. A home with space, flexibility, and great potential—don’t miss the opportunity to make it yours!

804 Fernwood Ave, Pleasantville

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