Chappaqua Homes with Driveway Parking features

Chappaqua Homes with Driveway Parking features

Welcome to Chappaqua, a picturesque community nestled in Westchester County, New York, renowned for its exceptional school district and charming suburban atmosphere. With a rich history and a vibrant local culture, Chappaqua is not only a desirable place to live but also an ideal environment for families seeking quality education and a sense of community.

The Chappaqua Central School District is consistently recognized for its outstanding academic programs and dedicated faculty. With a commitment to fostering a love of learning, the district offers a robust curriculum that includes a wide range of Advanced Placement courses, arts programs, and extracurricular activities. The schools are equipped with state-of-the-art facilities and resources, ensuring that students receive a top-notch education. Parents can feel confident that their children are being prepared for success in an increasingly competitive world.

In addition to the educational advantages, Chappaqua boasts a variety of beautiful homes, many of which feature convenient driveway parking. These residences provide not only ease of access but also the comfort and security that homeowners desire. Imagine coming home to your charming abode, with a designated space for your vehicle, allowing you to relax and unwind after a busy day.

Chappaqua's enchanting neighborhoods, coupled with its top-rated schools and inviting homes, create a perfect blend for families and individuals alike. Whether you’re looking for a cozy cottage or a spacious family home, you’ll find that Chappaqua offers a welcoming atmosphere and a strong sense of community that makes it a truly special place to call home. Discover the magic of Chappaqua today!

Newest Chappaqua Homes with Driveway Parking features

$1,150,000
4 Beds ⋅ 3 Baths ⋅ 1024331 MLS
***CHAPPAQUA SCHOOL DISTRICT*** Tucked away on a quiet cul-de-sac and set on nearly half an acre of beautifully landscaped property, this sun-filled Colonial offers the perfect combination of space, comfort, and convenience. Thoughtfully maintained and move-in ready, the home features almost 3,000 square feet of inviting living space for everyday living and effortless entertaining. A welcoming foyer leads to the spacious eat-in kitchen appointed with granite countertops, stainless steel appliances, and generous prep space with an adjoining dining room ideal for hosting gatherings. The fully enclosed family room anchored by a wood-burning fireplace and framed by oversized windows can be used as a bright, spacious office or a fifth room. A versatile office/mudroom, powder room, and access to the attached two-car garage complete this level. Just a few steps up, the expansive living room offers a bright, airy retreat with hardwood floors and large windows overlooking the surrounding property—creating the perfect space to relax or entertain. A few more steps lead to the private bedroom level, where the spacious primary suite features an en-suite bath and generous closet space. Three additional well-proportioned bedrooms share a full hall bath, offering comfortable accommodations for guests or flexible work-from-home needs. The finished walk-out lower level provides exceptional bonus space ideal for a recreation room, playroom, fitness area, or media room, along with laundry and abundant storage. Outside, a spacious recently refinished deck overlooks the private, tree-lined backyard, creating a peaceful setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings. Ideally located 7 minutes from downtown Mount Kisco and the Metro North station and 5 minutes from Chappaqua Crossing, Whole Foods, and Lifetime Fitness. You’ll enjoy easy access to acclaimed restaurants, shopping, parks, all within the highly regarded Chappaqua School District. Offering an ideal blend of space, location, and lifestyle, this is a home you’ll enjoy for years to come.

49 E Ridge Lane, Mount Kisco
$1,550,000
3 Beds ⋅ 3 Baths ⋅ 1023910 MLS
1926 Colonial with timeless character on a private and level half-acre, walkable to the train station and village in Chappaqua, NY. Circular driveway and classic curb appeal set the tone; inside, hardwood floors flow through an open, light-filled layout. The kitchen opens to a fireplaced family room with deck access, plus a formal dining room and a living room with its own wood-burning fireplace and screened porch. Upstairs, lives as a four-bedroom layout, the primary suite is a true retreat - en-suite bath with sauna and private balcony overlooking the yard with Koi pond plus an office/den, and a full hall bath. The partially finished lower level adds a playroom, wine closet, and storage. Brand new central air conditioning, plus a gas line on the street, offers possible future conversion.

312 Quaker Road, Chappaqua
$1,590,000
3 Beds ⋅ 3 Baths ⋅ 1017997 MLS
Enter into this enduring Colonial blending elegance with today's lifestyle. This home lives like a 4-bedroom and has 4 BR septic. Set on beautifully landscaped property moments away from town, the train and Chappaqua schools. Tastefully expanded and renovated in 2008, this home showcases classic architectural details everywhere. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs EIK with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace and a wall of windows to view the private setting. The sunroom offers custom built-ins and an abundance of natural light. A first floor bonus room and full bathroom works well for guests or an au pair. A mudroom with custom built-ins. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study, and en-suite bath with double sinks, marble shower and whirpool bath. Two additional bedrooms, one with custom built-ins, custom closets, and a hall bath. New laundry is located conveniently on the second floor. Outdoors, an expansive deck extending the living space and creating the perfect setting for entertaining, dining and relaxing while overlooking mature landscaping and private grounds that back up to protected green space. Completing the property is a detached two car-garage with generous storage above. The home was extensively renovated and expanded in 2008 offering the finest architectural finishes. An exceptional offering. New roof 2024 and new 4 bedroom septic 2026.

131 Douglas Road, Chappaqua
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 882412 MLS
Nestled on a picturesque tree-lined street in the highly sought-after Chappaqua School District, this beautifully renovated 4-bedroom Colonial combines timeless charm with thoughtfully updated living spaces. A welcoming front porch offers the perfect place to enjoy a quiet morning coffee or relax on a summer evening. A gracious entry foyer introduces the home's warm and inviting interior. The sun-filled living room features oversized windows, custom built-ins, and elegant proportions, creating a comfortable space for everyday living and entertaining. At the heart of the home is the beautifully renovated chef's kitchen with top of the line stainless appliances, designed for both function and style, with a spacious center island with seating, a sunny dining area, built-in desk, generous walk-in pantry, and access to the deck for seamless indoor-outdoor living. Just beyond the kitchen, the inviting family room is anchored by a raised-hearth wood-burning fireplace, offering a warm and comfortable gathering space. The first floor also includes a formal dining room and a versatile room with walls of windows, ideal as a second family room, home office, playroom, or sunroom, a full bath and laundry room. Upstairs, the primary suite has a renovated bath and large walk-in closets. Three additional bedrooms share a well-appointed hall bath, providing ample space for family and guests. The expansive lower level offers exceptional storage and outstanding potential for future finished recreation, fitness, or media space. Throughout the home, rich hardwood floors, custom millwork, abundant natural light, and a thoughtfully designed open floor plan create an atmosphere that is both elegant and welcoming. Ideally located in one of Chappaqua's most desirable neighborhoods, this is a home that offers timeless appeal, exceptional comfort, and a setting you'll enjoy for years to come. A must see home!!

12 Brandon Drive, Mount Kisco
$1,998,999
4 Beds ⋅ 4 Baths ⋅ 1011189 MLS
Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining. The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace. The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs. Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation. A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

4 Old House Lane, Chappaqua
$879,000
3 Beds ⋅ 3 Baths ⋅ 1006886 MLS
Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5 Bathrooms, many updates throughout the home, including the exterior deck. The Living Room has custom built-ins. An inviting Dining Room for memorable meals and an Eat-in-Kitchen with quartz countertops and stainless steel appliances, both rooms have sliding doors onto the deck. It features hardwood floors throughout, many closets and storage spaces. The Primary Bedroom has a Juliet Balcony, En-Suite bathroom with Double sink vanity, Second Bedroom with Skylights, Third Bedroom with Hallway Bathroom. Close to Train, Close to Downtown Dining and Shops, Close to Schools. Property includes 1-Car Attached Garage with Driveway for 1 additional car. Amenities include: Inground Pool and Tennis Courts.

2 Timberland Pass, Chappaqua
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 997307 MLS
Private access to the scenic North County Trailway, offering miles of paved trails for walking, running, and biking, is just one of the many highlights of this beautifully maintained home. Not to be missed, this sun-filled 3-bedroom, 3-bath raised ranch offers a comfortable layout ideal for both everyday living and entertaining. Set privately on over 1.3 level acres and screened from the road by a row of mature trees, the property provides exceptional privacy and a peaceful setting. Enjoy summers by the in-ground pool, a spacious backyard perfect for play and gatherings, and the convenience of a 2-car garage. Ideally located in the heart of Millwood, close to shopping, restaurants, and major parkways and in Chappaqua Schools, this home offers the perfect balance of privacy, recreation, and convenience. New AC!

568 Saw Mill River Road, Millwood
$2,649,000
4 Beds ⋅ 5 Baths ⋅ 998577 MLS
Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the ultimate turnkey lifestyle only moments from downtown Chappaqua, Metro North, and top-ranked schools. A dramatic arrival sets the tone as you enter through oversized custom doors into sun-drenched interiors framed by soaring 10-foot ceilings, expansive walls of glass, and wide-plank white oak flooring throughout. The home’s seamless open-concept design was thoughtfully curated for both grand-scale entertaining and intimate everyday living, creating a warm yet elevated atmosphere in every room. At the heart of the home is a spectacular chef’s kitchen worthy of a luxury design showroom, featuring premium professional-grade appliances, bespoke custom cabinetry, oversized quartzite island, designer lighting, and exceptional prep and storage space. Flow effortlessly into the breathtaking great room anchored by a statement fireplace and oversized sliders that open to a covered outdoor lounge, creating a true indoor-outdoor living experience. The primary suite is a private sanctuary rivaling a five-star resort, complete with a boutique-inspired dressing room and a spa-caliber bath featuring radiant heated floors, custom marble steam shower, soaking tub, and designer vanities. Generously sized ensuite bedrooms provide exceptional comfort and privacy for family and guests alike. The fully finished walk-out lower level elevates the home even further, offering an extraordinary extension of living space ideal for a private wellness retreat, gym, media lounge, golf simulator, wine tasting room, or entertainment venue. A striking custom wine display serves as a dramatic focal point and conversation piece. Every inch of this residence reflects a commitment to luxury and modern convenience, including geothermal heating and cooling, smart-home integration, premium fixtures and finishes, oversized heated garage space, and meticulously curated landscaping designed for both beauty and privacy. A rare offering that blends modern elegance, privacy, and convenience just under an hour from Manhattan. Come see a flawless fusion of contemporary design, superior craftsmanship, and effortless luxury set within one of Westchester’s most coveted communities today.

40 Hamilton Drive, Chappaqua
$2,499,000
3 Beds ⋅ 4 Baths ⋅ 973551 MLS
Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat. Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

33 Greenbriar Drive, Chappaqua
$1,590,000
3 Beds ⋅ 4 Baths ⋅ 984583 MLS
Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor primary suite, providing a serene sanctuary with a spa-inspired ensuite bathroom and an expansive walk-in closet. The second level serves as a versatile retreat, home to a spacious second bedroom, a dedicated home office/bedroom, an inviting sitting area, and a gorgeous private terrace. Additional living space abounds in the fully finished lower level, perfectly suited for a high-end home gym and a cozy media den, while the attached two-car garage comes equipped with an EV charging station for modern convenience. Residents enjoy an unparalleled "village within a village" lifestyle defined by sprawling green space and scenic walking trails, with exclusive access to a luxury clubhouse and sparkling pool. Situated in the heart of Chappaqua, this residence is just steps from Whole Foods, Life Time Fitness, delicious restaurants, and offers the convenience of a private community shuttle to the Metro-North for a seamless commute to Manhattan.

17 Lila Lane, Chappaqua
$809,000
4 Beds ⋅ 3 Baths ⋅ 981423 MLS
Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and brand-new stainless-steel appliances. The spacious primary suite, versatile enough to serve as a large family room, includes a walk-in closet and a newly renovated en-suite bathroom. Upstairs, three generously sized bedrooms await, including a second primary suite with a walk-in closet, and a second full bathroom. Additional highlights include a welcoming front porch, expansive attic storage, a full basement with crawl space, and a circular driveway accommodating up to six cars for effortless access. Enjoy summer days in the fenced backyard—perfect for gatherings, gardening, or basking in the sunshine. This prime location is minutes from the Train Station, library, town hall, post office, shops, restaurants, top-rated schools, and easy access to major parkways. Zoned for versatility, this property offers a potential for conversion back to commercial use, for an attorney’s office, dental practice, or other professional ventures in the bustling heart of Chappaqua. Don’t miss your chance to own this delightful home with endless possibilities! The house is no longer furnished as shown in the photos.

73 S Bedford Road, Chappaqua
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 950756 MLS
1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua
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