Chappaqua Homes with Attached Parking features

Welcome to Chappaqua, New York – a hidden gem nestled in the heart of Westchester County! Known for its picturesque landscapes and vibrant community, Chappaqua is not just a place to live; it’s a lifestyle. One of the standout features of this charming town is its exceptional school district, which consistently ranks among the top in the state.

The Chappaqua Central School District is renowned for its commitment to academic excellence, offering a robust curriculum that nurtures creativity and critical thinking. With a variety of extracurricular activities, advanced placement courses, and a dedicated faculty, students here are encouraged to thrive both academically and personally. Parents can take comfort in knowing their children are receiving a high-quality education in a supportive environment.

When it comes to finding your dream home in Chappaqua, you’ll be delighted to discover a range of properties that come with attached parking features. Imagine the convenience of having your vehicle just steps away from your front door, providing easy access for your busy lifestyle. Whether you’re looking for a cozy townhouse or a spacious family home, Chappaqua offers a variety of options that cater to your needs.

With its serene neighborhoods, top-rated schools, and convenient amenities, Chappaqua is the perfect place to plant roots and create lasting memories. Experience the charm of this vibrant community and explore the homes that come with the added benefit of attached parking – a true convenience for today’s homeowner!

Newest Chappaqua Homes with Attached Parking features

$5,750,000

6 Beds ⋅ 8 Baths ⋅ 1017994 MLS

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks its scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

24 Trails End, Chappaqua

$1,399,000

3 Beds ⋅ 3 Baths ⋅ 1046960 MLS

SoHo in Chappaqua! Chappaqua schools! Dramatic, Airy and Light-filled 3 Bedroom Contemporary in immaculate condition located in sought-after neighborhood and Cul-De-Sac. Set on almost an acre of private property with rocking-chair front porch. Elegant living room features a soaring cathedral ceiling, wall of built-in bookshelves and wall of windows opening to dining area with access to deck. Renovated eat-in-kitchen offers granite countertop, pantry closet, stainless steel appliances and breakfast area with access to deck. Large family room with wood stove and custom mantle. Den/Office/Study with closet and renovated new bath completes the first floor. Primary bedroom with walk-in-closet, an additional closet and freshly renovated in-suite full bathroom. Two addditional bedrooms with renovated Jack-and Jill bath. Full semi finished lower level with Library and Recreational/Gym room 281sqft with CO (included in total). This exceptional home with wall of windows, skylights, high/cathedral ceilings, open floor plan, two decks, Living Room, Family Room with Fireplace, Office/Den, Eat-In-Kitchen, hardwood floor with views of lush park property is ideal for indoor and outdoor entertaining. A must see!

10 Deborah Lane, Chappaqua

$1,575,000

4 Beds ⋅ 3 Baths ⋅ 1047882 MLS

Welcome home to Chappaqua's best kept secret right in town! This classic 1989 center hall colonial has been reimagined for the way we live today, blending sun drenched, open spaces with effortless modern style, all less than a mile to the charming village, convenient train and public library. Step inside to a first floor that flows beautifully from room to room. The open concept living and dining rooms and kitchen bask in natural light all day long, anchored by a striking fireplace that begs for cozy evenings in. Need a smaller spot to unwind? The family room off the kitchen is the perfect retreat for movie nights and quiet mornings. The chef's kitchen is where this home truly shines, with a generous island for gathering and doors that open onto a sprawling deck. From there, steps lead down to a private yard, made for summer barbecues, morning coffee, and everything in between. Indoor outdoor living has never felt so seamless. A well appointed laundry room and stylish half bath round out this level. Upstairs, four bedrooms offer a peaceful escape, headlined by a primary suite with a generous walk in closet and a spa like bath that feels like your own private retreat. The lower level delivers exceptional storage with convenient walk out access, and a two car garage with EV charging plus ample driveway space means there is room for everyone. This home has been loved and is ready for the next owner to enjoy it. Welcome home.

9 Lori Lane, Chappaqua

$1,359,000

3 Beds ⋅ 3 Baths ⋅ 1041830 MLS

Welcome to this spacious and private Millwood home, ideally located in the award-winning Chappaqua School District. This 3-bedroom, 2.5-bath home lives like a 4-bedroom (currently used as a dedicated home office/den). A charming woodland driveway leads to a light-filled home featuring hardwood floors, oversized windows, and beautiful decorative mouldings. The main level offers an eat-in kitchen with a bright breakfast nook, formal dining room, living room, large sunken entertaining room with a fireplace, powder room, and easy access to the private grounds. The outdoor deck, surrounded by lush woodland, natural rock formations, and mature landscaping, is perfect for relaxing and entertaining. Upstairs are three spacious bedrooms, a flexible home office/den, and two full baths. The primary suite features a separate sink and vanity area. A two-car garage adds convenience. Enjoy the best of the Chappaqua and Millwood lifestyle, with nearby hiking trails, Gedney Park, local shops and restaurants, and convenient access to Metro-North and Taconic Parkway for an easy NYC commute. A peaceful private retreat with the convenience of being close to it all.

180 Somerstown Road, Millwood

$839,999

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

$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

$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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