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$475,000
2 Beds 1 Baths 1030479 MLS
Welcome home to effortless, low-maintenance living in the highly sought-after Greenwood Condominium complex. Located on the first floor with seamless, step-free access, this bright and inviting 2-bedroom home pairs mid-century charm with smart, modern updates. Inside, refinished hardwood floors and generous natural light frame serene views of the beautifully landscaped grounds. The thoughtful layout features an updated eat-in kitchen, an expansive living and dining area, 2 generously sized bedrooms, a full hall bath, and six impressive closets - including an oversized front hall closet. Best of all, the unit comes with a one-car garage that offers covered parking and ample storage. There is also plenty of on-site guest parking and nearby common laundry. Situated in the heart of the Village of Pleasantville - just steps from the Pleasantville Metro North station, the renowned Jacob Burns Film Center, local dining, boutique shops, the Pleasantville famer's market, Pleasantville schools, and the PACE University campus - the location is unbeatable. With low monthly HOA and annual taxes, this property is an ideal match for first-time homebuyers, downsizers, or anyone seeking an easy Westchester commute.

590 Bedford Road Unit #3, 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

$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

$349,000
1 Beds 1 Baths 1019926 MLS
Welcome to this spacious second-floor one-bedroom condo in the heart of the Village of Pleasantville! Offering a comfortable layout and an unbeatable location, this home is ready for its next owner to move right in and make it their own. The galley kitchen features natural oak cabinetry, a tile backsplash, tile flooring, and a cozy eat-in area. While the kitchen and bathroom retain their original 1980s finishes, they have been well maintained and offer a wonderful opportunity to update at your own pace. A fresh coat of paint is all that's needed to make this home shine from day one. The generously sized living room easily accommodates both a comfortable living/TV area and additional space for a dining area or home office. The spacious bedroom includes two double closets, providing excellent storage. New neutral wall-to-wall carpeting has been installed in the living room, bedroom, and the interior staircase leading to the apartment, creating a fresh, inviting feel throughout. Additional features include a dedicated one-car garage #50 and access to a common laundry room conveniently located beneath the 580 building. Ideally situated just 0.4 miles from the Metro-North train station, this condo is also within easy walking distance of the renowned Jacob Burns Film Center, charming shops, restaurants, and all that vibrant downtown Pleasantville has to offer. Whether you're a first-time buyer, downsizer, or commuter, this home offers outstanding value in one of Westchester's most desirable communities.

600 Bedford Road Unit #6, 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

$435,000
1 Beds 1 Baths 1014284 MLS
Step into elegance and comfort in this beautifully maintained, rarely available second-floor Pembroke model condominium in the highly sought-after Foxwood community. This move-in-ready home offers the perfect blend of style, convenience, and low-maintenance living. The bright eat-in kitchen features attractive butcher block-style countertops, beautiful white cabinetry, abundant storage and plenty of space for casual dining. Just off the dining area, step onto your private covered balcony overlooking the beautifully maintained community grounds an ideal spot to enjoy your morning coffee or unwind after a long day. Back inside, you'll find a spacious living room filled with natural light, a convenient in-unit washer and dryer, a beautiful full bathroom and a generously sized bedroom featuring a ceiling fan and a large walk-in closet. Additional highlights include a secure private storage area. Common charges include heat, hot water, landscaping, snow removal, Tennis or Pickleball courts and access to three community swimming pools. Perfectly situated in the heart of Pleasantville, Foxwood is just minutes from the Jacob Burns Film Center, the renowned Pleasantville Farmers Market, shopping, dining, parks, and recreation. Commuters will appreciate being just 1.4 miles from the Metro-North train station, offering an easy commute to New York City, along with quick access to major highways. Enjoy the best of Central Westchester living where everything is close and convenience meets comfort.

8 Foxwood Drive Unit #8, Pleasantville

$275,000
2 Beds 1 Baths 1012138 MLS
Updated and meticulously maintained co-op ideally located just moments from both the heart of Pleasantville and the Metro-North station, offering an effortless commute and vibrant village living. This inviting home features a modern, comfortable layout and quality finishes throughout. The updated kitchen offers clean lines, ample cabinetry, and functional workspace designed for everyday living and easy entertaining. The living and dining areas feel bright and open, with well-proportioned rooms that create a natural flow and a warm, welcoming atmosphere. The bedroom is generously sized with excellent closet space, while the updated bath reflects the same level of care and maintenance found throughout the home. Beautiful hardwood floors. Residents enjoy a peaceful residential setting while still incredibly close to everything. The Village of Pleasantville offers charming shops, restaurants, parks, and a lively downtown, all just a short distance away. Commuters will appreciate the easy access to the Metro-North Railroad station, making travel to NYC straightforward and convenient. One car garage is included. Attic area for additional storage. A rare combination of condition, location, and lifestyle, this is an excellent opportunity to enjoy low-maintenance living in one of Westchester’s most desirable villages.

73 Broadway Unit #2J, Pleasantville

$2,100,000
6 Beds 5 Baths 944741 MLS
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.

235 Bear Ridge Road, Pleasantville

$2,725,000
867179 MLS
The Marmaduke Forster House, nestled in the heart of Pleasantville, New York, is a living testament to history and architectural magnificence. This remarkable property, defined by its Queen Anne Victorian elegance and historic significance, offers an unparalleled opportunity for those pursuing a unique and promising investment in office spaces. The property comprises 13 offices, boasting a remarkable track record of consistently low vacancy rates. With a history dating back to 1785, the Marmaduke Forster House is a prominent staple in the Pleasantville community. Recognized by the Department of the Interior on its list of National Historic Places, this property showcases a wealth of historical context and heritage. Approaching this property, the immediate allure of architectural excellence is undeniable. The stately columns, symmetrical facade, and welcoming gabled roof draw attention, creating a striking first impression. The meticulously landscaped gardens and ample parking enhance the property's charm and functionality, ensuring an elegant and practical workspace. As you enter the property, you are transported to an era of luxury and meticulous craftsmanship. The grand entrance foyer, marked by soaring ceilings and intricate moldings, extends a warm embrace. Every corner has period-appropriate details, from original fireplaces to ornate woodwork. The Marmaduke Forster House offers versatile office spaces, accommodating diverse businesses and professional services. While preserving its historical charm, the Marmaduke Forster House was equipped with contemporary amenities. Updated HVAC and electrical systems ensure comfort and efficiency, while high-speed internet connectivity keeps your operations running smoothly. Additionally, modern kitchens and restroom facilities deliver convenience for all occupants. Pleasantville, New York, is experiencing a significant growth and redevelopment period. This thriving community is witnessing new development projects and revitalizing existing infrastructure. It's an exciting time for Pleasantville as it embraces the future while preserving its rich historic heritage. The property boasts a prime location within the village with many advantages. Easily accessible, it enjoys proximity to major highways and public transportation. The neighborhood provides numerous amenities, encompassing dining, shopping, and recreational activities. The Marmaduke Forster House is a rare and invaluable opportunity for prospective owners to acquire a piece of Pleasantville history. Its enduring architectural allure, versatile office spaces, and contemporary amenities highlight its status as a sound investment. Take the chance to make this unique property your own. Contact us today.

413-415 Bedford Road, Pleasantville

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.