Pleasantville Homes under $1 million

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Newest Pleasantville Homes under $1 million

$850,000

3 Beds ⋅ 2 Baths ⋅ 1052833 MLS

Well-maintained two-family home ideally located in the heart of Pleasantville Village. Situated on a flat, usable lot, this property features a detached two-car garage plus ample driveway parking. Both kitchens and bathrooms have been updated, and the home offers low-maintenance vinyl siding and newer windows throughout. Key improvements include a roof approximately 14 years old and a furnace replaced just 8 years ago, providing added peace of mind. The full unfinished basement offers abundant storage space, mechanicals, and convenient walkout access. Enjoy the convenience of being just minutes from everything Pleasantville has to offer, including shopping, restaurants, delis, schools, the library, farmers market, parks, recreation facilities, and the Metro-North train station. With quick access to major highways and an easy commute to New York City, this property is an exceptional opportunity for both homeowners and investors alike.

7 Hopper Street, Pleasantville

$929,000

4 Beds ⋅ 3 Baths ⋅ 1051611 MLS

Welcome to this inviting 4-bedroom, 2.5-bath home ideally located just outside the heart of Pleasantville Village. Enjoy the convenience of being within easy walking distance to town, with its restaurants, shops, entertainment, and everyday amenities. The home offers a flexible layout with a private in-law/guest suite, perfect for extended family, guests, or additional living space. A spacious backyard provides plenty of room for outdoor entertaining, play, gardening, or simply relaxing. A wonderful opportunity to enjoy the best of Pleasantville living in a convenient, walkable location

1 Brookfield Place, Pleasantville

$750,000

3 Beds ⋅ 2 Baths ⋅ 1048774 MLS

Live in the heart of Pleasantville in a home as distinctive as its location. Just 0.4 mile from Metro North and moments from the village center, 3 Elm Street pairs an exceptionally convenient location with interiors that feel anything but expected. Fully renovated, this three bedroom Colonial features dark painted trim, rich color, patterned wallpaper and thoughtfully chosen finishes that give the home a collected, design forward feel. The formal dining room makes a memorable first impression, while the renovated kitchen mixes soft gray cabinetry, graphic flooring and a substantial center island. The adjoining living room is bright and comfortable, with direct access to the patio and fenced backyard. An oversized garage offers tremendous potential for a workshop, studio, gym or additional storage, while the generous driveway provides parking for multiple cars. Outside, the patio and fenced yard extend the living space with room for dinner, a garden or a quiet afternoon at home. This is an exceptional entry point into Pleasantville and the lifestyle that comes with it. Walk into the village for coffee, dinner or a show. Spend Saturday morning at the farmers market. Walk to Metro North for the commute into Manhattan, or enjoy the dog park, parades, festivals and community events throughout the year. There is an extraordinary amount of life packed into this 1.8 square mile village, and 3 Elm Street puts you right in the heart of it. This is a home that makes it remarkably easy to become part of the community around it.

3 Elm Street, Pleasantville

$739,000

3 Beds ⋅ 1 Baths ⋅ 1050254 MLS

Welcome to 82 Birch Drive, a charming 3-bedroom, 1-bath home situated on two parcels along a quiet dead-end street in Pleasantville, offering a peaceful hillside setting surrounded by mature trees. Inside, hardwood floors throughout add warmth and character, while a beautiful arched doorway connects the living and dining rooms. The extended living room area features skylights and a high ceiling, bringing additional natural light and an open, airy feel to the space. The partially finished basement provides additional flexible space and was previously used as a home office, with additional areas available for storage and other needs. Outside, the two-parcel setting provides additional outdoor space to enjoy, along with ample parking. Located adjacent to Graham Hills Park, the home offers convenient access to outdoor recreation while remaining just minutes from the Pleasantville Metro-North station, downtown Pleasantville, shopping, dining, and major roadways. With its tranquil setting, hardwood floors, charming architectural details, extended living room, flexible lower-level space, ample parking, two-parcel property, and convenient location, 82 Birch Drive offers a wonderful combination of character, space, and convenience.

82 Birch Drive, Pleasantville

$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

$425,000

1 Beds ⋅ 1 Baths ⋅ 1049438 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

$619,000

2 Beds ⋅ 2 Baths ⋅ 1045921 MLS

Welcome to desirable Foxwood Condominiums in Pleasantville! A rare opportunity to unlock the full potential of this 2 bedroom 2 full bath Somerset unit. Entry Foyer with 2 Closets, Spacious Eat-in Kitchen with Dining area, additional Cabinetry, Formal Dining and Living Room with Picture Window and a Door Out to the Deck. Hall Bathroom, Hall Linen and Laundry Closets, Primary Bedroom with Primary Bath, Walk-in Closet and a 2nd Bedroom with sliding doors, closet. A true diamond in the rough. The property is being offered in its present condition. With the right vision, this home presents an opportunity to create a home tailored to your style in a sought after location. Heat and hot water are included in the common charges, along with full landscaping and snow removal. Amenities include 3 swimming pools, village tennis courts and playground. Foxwood is just minutes from everything Pleasantville has to offer, from Jacob Burns Film Center, to Saturday's Farmers' Market, to shopping, Restaurants, Metro north train and major highways.

16 Foxwood Drive Unit #8, Pleasantville

$689,000

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

590 Bedford Road Unit #1A, Pleasantville

$479,000

2 Beds ⋅ 1 Baths ⋅ 1036136 MLS

Easy Living in the Heart of Pleasantville! Welcome to this beautiful two-bedroom, first-floor condo in the desirable Greenwood Condominiums, offering no steps and effortless one-level living. Freshly painted and filled with natural light, this spacious home features a welcoming living room, updated kitchen with stainless steel appliances, warm wood cabinetry and a convenient breakfast bar, along with beautiful hardwood floors throughout. A detached one-car garage provides covered parking and additional storage. The location is hard to beat! Just steps from the Metro-North train station, Farmers Market, Jacob Burns Film Center, schools, shops, restaurants, and all that the Village of Pleasantville has to offer. Whether you're a first-time buyer, downsizing, or simply looking for a home that makes everyday life easier, this is easy living in an unbeatable village location.

590 Bedford Road Unit #1A, Pleasantville

$899,000

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

$259,000

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

$849,999

4 Beds ⋅ 2 Baths ⋅ 996830 MLS

NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday living and entertaining. The spacious living room provides the ideal setting for gatherings and holidays, while multiple freshly stained multi-level decks create seamless indoor-outdoor living perfect for entertaining, summer barbecues, or relaxing evenings overlooking the expansive park-like property. The large yard offers endless possibilities for play, gardening, and recreation, plus three storage sheds for added convenience. Also included is a 11'x54' triangular shaped lot on north side of primary lot. .46 Acre Total Recent updates including a newer roof and boiler provide peace of mind, while the attached garage adds practicality and storage. Commuters will love the easy 5-minute walk to the Chappaqua train station with approximately 45-minute access to Grand Central Terminal. Rarely offered, this home also includes FREE school bus pickup within Pleasantville’s walking district. Ideally located just minutes from the farmers market, shops, restaurants, parks, and Metro-North, this move-in ready home delivers comfort, charm, and an exceptional lifestyle in one of Westchester’s most sought-after communities. Easy to show same day showings are ok now.

249 Mill River Road, Chappaqua

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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.