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

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 1036792 MLS

Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood burning fireplace, this one brick, spanning floor-to-ceiling with raised hearth. Sliding glass doors lead from the Family Room to an Azek deck installed in 2016. Walk through the formal dining room accented with chair rail and crown molding, into a chef's kitchen with Richmaid cabinetry and tumbled marble backsplash with hand painted accents, a center island, and GE Monogram 6 burner gas stove with convection oven, farm sink, GE Monogram side/side refrigerator, microwave and dishwasher. Sliding glass doors open from the kitchen to deck with internal shades. The second floor Primary bedroom has a private bath with steam shower, double vanity and a Crema Marfil counter, whirlpool tub and radiant heated stone floors. The walk out lower level is included in the square footage and has a laundry room, playroom and a full bath. The mechanicals include: 4 zone heat, 3 zone AC, sophisticated sound system and CAT 5 wiring, full house generator (2014) Azek deck with an automated awning, fenced in yard, above ground oil tank (2024) and irrigation system. Enjoy this professionally landscaped retreat, minutes from downtown with easy Metro-North railroad service to New York City.

20 Hitching Post Lane, Chappaqua

$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

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 992104 MLS

Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this November 2026. Early buyers will have the rare chance to customize some of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives like a larger home thanks to additional flexible living spaces. The main level features an open-concept design with seamless flow between the kitchen, dining area, and informal living room with fireplace. The kitchen is equipped with a premium Thermador appliance package and includes sliding glass doors leading to the back patio, while the family room also features sliders to the covered patio—creating a seamless connection and the perfect setting for indoor-outdoor entertaining. In addition to the formal dining room, formal living room, and powder room, the main level also includes a versatile room adjacent to a full bathroom, ideal for use as a private office, den, or guest accommodations. The fully finished walk-out lower level adds substantial additional living space, including an additional room with sliding glass doors and access to a full bathroom—well-suited for a variety of uses including extended living, recreation, or work-from-home needs. The primary suite is a true retreat, showcasing a tray ceiling, two oversized walk-in closets, and a luxurious bathroom with double vanity, soaking tub, separate shower, and private toilet room. A second-floor laundry room adds everyday convenience. Just a few additional highlights include 9-foot ceilings throughout, 4" oak hardwood floors, high-end finishes across all levels, an oversized two-car garage leading to a mudroom with custom cubbies and closet, a high-efficiency heat pump and cooling system, pre-wiring for a future electric vehicle charging station, and a security system. Privately set on over an acre of land on a cul-de-sac street and surrounded by mature trees, this home offers a peaceful setting while remaining close to parks, town, schools, and transportation. A rare opportunity to own a brand-new, thoughtfully designed home with exceptional flexibility in an ideal Chappaqua location.

39 Barnes Lane, 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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.