Pleasantville, NY Homes for Sale with Parking

Welcome to 302 Washington Avenue, a beautifully crafted 5-bedroom, 4-bathroom Colonial located in one of Pleasantville’s most sought-after neighborhoods. This newly constructed home combines timeless design with modern amenities, all within walking distance to Metro North, local shops, restaurants, and scenic parks—perfect for those seeking convenience without compromising on luxury.Step

Cathy DeBow William Raveis Real Estate

Don’t walk—run to this rare 3,500 square foot end-unit townhome in The Enclave, Pleasantville. Perfectly situated on one of the community’s most desirable lots, it offers a private oversized backyard, expansive deck, and patio. Inside, the light-filled open layout showcases a Chef’s kitchen with stainless steel appliances, a walk-in pantry, hardwood floors, custom millwork, and plantation

Sari Shaw Compass Greater NY, LLC

Historic 1830's home, original Pleasantville School Building located on a small private road in the heart of Pleasantville. Just a short walk to all this beautiful town has to offer. Beautiful features such as a wrap around porch, cozy family room with a fire place, large eat in kitchen and a private primary bedroom, will have you wanting to move right in and make this house your home. All of

Sharon Foley ERA Insite Realty Services

Final and best on 9/12 at 12:00. This custom-built Contemporary Colonial offers the best of modern luxury, elegant amenities with attention to detail all in this private park like setting at the end of a cul-de sac. This lovely home is impeccably maintained and shows pride of ownership with an expansive yet intimate environment for comfortable family living, and great flow for entertaining. As

Jeanne Beckley Howard Hanna Rand Realty

**Back on Market - Buyer’s Financing Fell Through! ** This is your chance to own the lowest-priced home in The Enclave at Pleasantville, one of the area’s most sought-after communities. With other residences selling at significantly higher price points, this property offers exceptional value and tremendous upside potential - especially with the opportunity to finish the basement and

Daniela Grisanti HomeSmart Homes & Estates

This sophisticated four-bedroom residence offers an ideal blend of convenience and tranquility just north of New York City. Enjoy the ease of walking to the vibrant village of Chappaqua—with its boutiques, cafes, and train station—while benefiting from the highly regarded Pleasantville School District. Commuting is effortless with the Chappaqua station mere minutes away and seamless access to the

Sari Shaw Compass Greater NY, LLC

Modern convenience meets the tranquility of nature in this mid-century inspired retreat. Set on 1.04 acres, this 3,160 SF contemporary home blends privacy, clean lines, and seamless indoor-outdoor living. Expansive Marvin windows, vaulted ceilings with skylights, exposed beams, and a sunken living room connect every space to the outdoors. Multiple decks invite you to read, bird watch, or simply

Kim Tromba Keller Williams Prestige Prop

Set privately in the highly sought-after Enclave neighborhood, this beautiful end unit offers the perfect blend of luxury, space, and convenience. Exceptionally upgraded and meticulously maintained, this home is truly move-in ready. Step inside to discover an open and inviting floor plan featuring a light-filled great room with vaulted ceilings, a gas fireplace, and sliding doors that open to a

Alaina Bainlardi William Raveis-New York LLC

Welcome to 23 Brookside Place in Pleasantville, NY — a beautifully maintained, energy-efficient home set on three tax lots with room to expand. The main level offers timeless details including crown and baseboard molding, a spacious entry foyer with coat closet, and a bright living room featuring recessed lighting and a wood-burning fireplace with wood mantle and stone surround. The updated

Suzan Zeolla Houlihan Lawrence Inc.

Welcome to your slice of Pleasantville—where small-town charm meets everyday convenience. This 3-bedroom, 1.5-bath Craftsman-style home offers warmth, character, and a lifestyle that’s hard to resist. Start your mornings on the classic front porch, then head to the local Saturday farmers market just a short stroll away for fresh produce and friendly faces. Inside, the vintage kitchen features

Vanessa Catalano Julia B Fee Sothebys Int. Rlty

Welcome to this beautifully maintained one-bedroom co-op offering an abundance of natural light and classic charm in sought-after Pleasantville, NY. This bright and airy home features hardwood floors throughout, a spacious living area, and a well-proportioned bedroom—perfect for comfortable everyday living. Ideally situated less than one mile from the center of town and the Metro-North train

Tom Consaga RE/MAX Ace Realty

Welcome to your dream home nestled in the serene cul-de-sac of Pleasantville. This stunning 4-bedroom, 4-bathroom residence spans an impressive 3917 square feet, offering luxurious living with a touch of modern elegance. Step inside to discover a home that was rebuilt in 2023 and designed by local architect Tim Lener. A beautiful open floor plan adorned with exquisite wood floors that flow

Karen O'Connor Compass Greater NY, LLC

Modern Living Meets Natural Beauty in the Heart of Pleasantville. Perched above the charming village of Pleasantville, this modern masterpiece has been completely rebuilt from the ground up, offering a one-of-a-kind blend of contemporary design and character. Set on nearly three-quarters of an acre, the home offers privacy and serenity—yet is located under a mile from Metro North, with express

Matthew Valvano Berkshire Hathaway HS NY Prop

Set in the desirable Village of Pleasantville, this enchanting Colonial home, built in 1830 and sited on .78 acres, offers timeless character, unique architectural details, and endless potential. A true diamond in the rough, this residence, dubbed "Pierce House", is ready to be transformed into something truly spectacular. Far from cookie-cutter, this home tells a story. With its original charm

Grace LoBello William Raveis Real Estate

Just steps from downtown Pleasantville and train station, award-winning Pleasantville schools and local playgrounds, this charming home blends convenience with classic character. Bursting with curb appeal, this sun-drenched home features gleaming hardwood floors, a welcoming country kitchen complete with a butler’s pantry and access to formal dining room, perfect for entertaining or everyday

Theresa Szuhany RE/MAX Ace Realty

Executive Raised Ranch 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers plenty of storage .

Harry Donofrio Town and Village Real Estate

This bright and beautiful townhouse has everything you’re looking for—an open concept layout that feels spacious and welcoming with warm hardwood floors that instantly make it feel like home. The fully renovated eat-in kitchen features sleek quartzite countertops and modern finishes elevating and simplifying your everyday cooking experience. Natural light pours in from every angle and for all the

Vanessa Catalano Julia B Fee Sothebys Int. Rlty

Move right in to this 2-bedroom + loft, 2.5-bathroom townhouse in the highly sought-after Chappaqua School District. Freshly painted throughout and updated with brand-new quartz countertops, new dishwasher and new kitchen flooring, this home offers immediate comfort with the flexibility to personalize. The dining area features sliding doors that open to a grassy green space, while the kitchen

Karin Kimtis Compass Greater NY, LLC

All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.

Karin Kimtis Compass Greater NY, LLC