A suburb of New York City in northern Westchester County, the small, bucolic hamlet of Chappaqua blends seamlessly into the countryside as streets fan out from downtown, many becoming winding roads lined with maples, sugar oaks and beeches. “The area has an old-fashioned country feel to it. Life in Chappaqua is private and reserved and yet homey. It’s very Norman Rockwell-esque,” says Bridgette Bacon, a Realtor with American Family Realty. Downtown is the heart of Chappaqua, home to the train station, restaurants and shops. The area has an abundance of spaces, parks and nature preserves. In a large gazebo at the center of this fan-shaped community, the hamlet holds summer concerts. Many notable people have called the neighborhood home, including Horace Greeley, editor of the New-York Tribune. Former President Bill Clinton and his wife, former Secretary of State Hillary Clinton, still live in Chappaqua.
Downtown Chappaqua provides an assortment of shopping and dining options.
Bright artwork adorns the walls of a walkway in downtown Chappaqua.
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Homes that tell a story
“What makes Chappaqua so unique is that the older homes here were built with love. Husbands built homes for their wives and fathers built homes for their families. Every old home has a story, and many have engraved cornerstones that still attest to that love,” says Realtor Bacon, who has 7 years of experience selling real estate in the general area. Home prices range from around $325,000 for a one-bedroom condominium in town to $2.5 million or more for a four-bedroom craftsman on 2 acres. Single-family homes include a range of styles from ranch to contemporary to modern colonials. Streets in the town have sidewalks, roads further out do not. “If you live in town, it’s very walkable. You can come home on the train, go to the grocery store and Starbucks, and then walk home,” explains Bacon.
West Place homes in eastern Chappaqua provide tranquility and nice sized yards.
A modern home on Haights Cross Road in Chappaqua.
A contemporary home on West Pl in Chappaqua.
A cute and cozy washed brick home on West Pl in eastern Chappaqua.
The bright red door on this larger home on West Pl in Chappaqua really makes it stand out.
Classic tudor homes can be found across Chappaqua, NY.
Classic colonial homes can be seen across Chappaqua hilly streets.
Springfield Ct in Chappaqua has modern, new construction, in a convenient location to downtown.
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Strong scholastics and sports
Schools in the neighborhood fall under the Chappaqua Central School District. “The schools here excel both scholastically and athletically. No stone is left unturned to make sure every kid gets the best education possible,” says Bacon. Douglas G. Grafflin elementary has an A-plus rating from Niche and a student-teacher ratio of 13 to 1. Seven Bridges Middle School has an A-plus rating and a 10-1 student-teacher ratio. Horace Greeley High School also has an A-plus rating and a 10-1 student-teacher ratio. In 2015, U.S. News & World Report ranked it as the No. 1 school in the country.
Horace Greeley High School has great academic and athletic opportunities for students.
Educational opportunities abound at Robert E Bell School.
Roaring Brook School has dozens of effective and excellent teachers and staff.
Douglas G Grafflin School provides a safe, positive, nurturing environment for students.
Students are the highest priority at Coman Hill School.
The courses at West Patent Elementary School encourage critical thinking and creativity.
Byram Hills High School has great academic and athletic opportunities for students.
H.C. Crittenden Middle School has dozens of effective and excellent teachers and staff.
Students are the highest priority at Wampus Elementary School.
EF Academy High School is a private school in the area.
Fox Lane High School on S Bedford Road in Bedford, NY.
In Armonk, the Montessori Children's Room shapes curious young minds.
Briarcliff Manor's beacon of religious education, St Theresa School.
The Westfield Day School, where Armonk's dreams and aspirations take flight.
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Playgrounds, parks and ponds
Gedney Park in Chappaqua features playgrounds, baseball and soccer fields, walking trails, a little free library, a pond and picnic areas. In the winter, it’s a popular spot for sledding and ice skating. Whippoorwill Park is the largest park in Chappaqua. It offers 3.5-miles of looped trail that takes hikers past heavily forested hills and rocky outcroppings. At the lower elevations, visitors will meet streams, wetlands and the tranquil Whippoorwill Lake.
Take a boat out on the water at Wampus Pond Park.
Take a break from the sun at Gedney Park.
Gedney Park offers multiple play areas and many miles of hiking trails.
Your kids will never want to leave New Castle Playground.
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Fashion and food in Chappaqua
Discerning shoppers can find the latest women’s fashions at Royal New York, found near the Whole Foods at the Chappaqua Crossing Retail Center. The Chappaqua Farmers Market, next to the train station, is open from May through December. The market offers shoppers locally grown and prepared fresh meats, fruit, fish, produce and baked goods. When it's time to dine out, the Old Stone Trattoria may look unimposing from the outside, but once inside, the stone walls, Mediterranean-inspired decor and signature Italian dishes mentally transport diners to Bella Italia. Since 1967, Lange’s Little Store and Deli has been a Chappaqua favorite. The restaurant serves bagels and hearty breakfast sandwiches. Workers and high school students text in their lunch orders for subs and sandwiches. At the end of the day, it’s a popular stop for picking up healthy and delicious to-go dinners.
Get all your daily food needs at Whole Foods in Chappaqua Crossing.
Whole Foods is a popular shopping destination for Chappaqua residents.
Bobo's Cafe is located at the historic Chappaqua train station building.
Sweetgreen is a busy eatery in Chappaqua.
Taco Street is a small but wonderful local eatery in downtown Chappaqua.
Warm weather is enjoyed by all in downtown Chappaqua.
Le Jardin de Roi is a no-frills authentic French bar and restaurant in Chappaqua, NY.
Enjoy a date night at Le Jardin de Roi .
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Getting in, around and out of town
Only 28 miles from New York City and 35 miles from LaGuardia Airport, commuters have many travel options, including several highways and train service. Saw Mill River Parkway, which runs through the center of town, and Hutchinson Parkway offer drivers the most direct routes to the city. Metro-North Railroad runs train service between Chappaqua and Manhattan about every half-hour. Local shuttle service is available in Chappaqua.
Events
The Chappaqua Performing Arts Center brings diverse art, music and cultural programs to the area. In May, Chappaqua’s annual Memorial Day parade is a sight to see. Marchers include military bands, colonial reenactors, veterans and even a former president. Concluding with a concert at the gazebo, the event is a red, white and blue tribute to the fallen and a hello to summer.
Crime
Scoring a 1 out of 10, the city has one of the lowest crime rates in America.
Written By
Robin Beres
Photography Contributed By
Chris Mantz
Video By
Chris Norton
Interested in learning more about homes in this area?
Reach out to
Therese Herrero,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chappaqua, NY sell after 39 days on the market compared to the national average of 57 days. The median sale price for homes in Chappaqua, NY over the last 12 months is $1,607,015, up 4% from the median home sale price over the previous 12 months.
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
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
Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this Fall 2026. Early buyers will have the rare chance to customize many 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
Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch
Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, wellness retreat, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy.
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
A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential.The 1st floor as commercial and the 2nd and 3rd floors residential apartments.An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments.One example:1st
Timeless elegance meets relaxed country chic at this extraordinary Chappaqua retreat. Ideally situated on one of Chappaqua's most coveted streets, this remarkable residence was originally built in 1910 and completely renovated and reimagined in 200l and then again in 2009 for modern living. Privately set amid beautifully landscaped grounds, 40 Algonquin blends classic country manor-style
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
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,
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
Welcome to Old Farm Lake - one of Chappaqua's most desirable condominium communities, offering low-maintenance living with resort-style amenities. This 3-bedroom, 2.5-bath townhome is set in a private setting and lives beautifully with natural light across three levels. The main level features an open living and dining area with cathedral ceilings, a skylight, and a wood-burning fireplace. The
Wilder Balter Partners, Inc., Hudson valley's premier developer of luxury homes has written a new chapter for the iconic reader's digest building. The four-story structure has undergone an unprecedented renovation, and the finished product embraces the nostalgia of the old media empire's headquarters with the extravagance of contemporary housing. Chappaqua Crossing Apts is now open! Please call
Bright contemporary 2-bedroom and 2-bathroom townhouse in desirable Chestnut Oaks. Enter through the foyer to the eat-in kitchen featuring a counter and stainless steel appliances. The formal dining area overlooks the sun-filled living room with vaulted ceilings, a wood-burning fireplace, and a sliding door to a patio and fabulous yard. Upstairs, you will find a bedroom and a full bath. Off the
Modern Farmhouse - Prime Location! Experience luxury living in this newly constructed custom-built modern farmhouse, Mere minutes from downtown Chappaqua and the train station. Situated on a beautiful flat yard, this meticulously crafted home offers the epitome of comfort and style.Key Features:- Spacious first-floor bedroom, providing luxurious comfort and convenience.-
Charming Village Rental with outdoor space in Chappaqua! Step into the timeless charm of this 2-bedroom, 1 -bath rental nestled in a classic Chappaqua home, where character and comfort come together in one of the area's most convenient location. Just a short distance from the village, you'll enjoy easy access to local cafes, restaurants, boutique shops, parks, and the Metro-North train station,
Patricia DelVecchioWilliam Raveis Real Estate
$10,000 per month
Stunning Updated Home with Private Pond Views in Chappaqua
Nestled on a beautifully landscaped property, this exceptional home offers the perfect blend of tranquility and convenience. Featuring an airy open-concept layout across three levels, the residence is filled with natural light and scenic views throughout.The beautifully renovated eat-in kitchen and dining area include radiant heated floors and flow into the spacious living room, where
Set far back from the road in a private and peaceful setting, this beautifully maintained home offers exceptional flexibility in the highly sought-after Chappaqua School District, just moments to town, Metro-North train to NYC, parks, shopping, and restaurants. Offering a flexible layout with 2 legal bedrooms plus additional office and bonus spaces that can live like a 3- or 4-bedroom home, this
Two floors. Two balconies. One address that puts everything Chappaqua within reach. This fully renovated condo at 150 N Bedford delivers the kind of space most rentals only promise — open concept living and dining anchored by an ethanol fireplace, soaring ceilings, and a floating stair system that makes a statement the moment you walk in. The sleek eat-in kitchen flows naturally into your day,
Welcome to 359 N. Greeley Ave, a beautifully renovated, move-in-ready home in the highly sought-after Chestnut Oaks community of Chappaqua.Enjoy easy living in this bright and updated 2-bedroom, 2-bathroom rental, ideally located less than a mile from downtown Chappaqua, the Metro-North station, shops, restaurants, and local schools within the award-winning Chappaqua Central School District.
This spacious bi-level apartment is in Chestnut Oaks Condominium located just half a mile from the train station and downtown shops. It is bright and open with high cathedral ceiling. Kitchen, living room and powder room are on the main level, with sliding doors leading to a patio. On cold nights you will enjoy the fireplace that is decorating the llvingroom wall. On the second floor is a large
Privately set on two beautifully level acres in Chappaqua’s sought-after Whippoorwill neighborhood, this sophisticated contemporary offers exceptional light, space, and seamless indoor-outdoor living. Thoughtfully updated and impeccably maintained, the home is surrounded by tranquil natural beauty with picturesque views from nearly every room. A dramatic open floor plan is enhanced by soaring
Unparalleled opportunity to attain one of the only 2 exceptional apartments in the corner turret at the newly constructed building in the heart of Chappaqua. Quality construction by a highly regarded local builder. This apartment features a stunning octagonal living room/dining room, 2 bedrooms and 2 full baths/ADA shower. Glamorous modern styling quartz counters, island open to bright open floor
Recently renovated raised ranch at 507 Millwood Road in Chappaqua. This spacious home sits on 1.13 private acres featuring mature landscaping, a footbridge and a stream.The 3,136 sq ft home offers 3 bedrooms, 3 bathrooms plus flexible living spaces that can easily function as a office , etc. Updated gourmet kitchen with granite counters, tiled backsplash and stainless steel appliances. The
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