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
Bill Reilly,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chappaqua, NY sell after 33 days on the market compared to the national average of 56 days. The median sale price for homes in Chappaqua, NY over the last 12 months is $1,630,000, up 3% from the median home sale price over the previous 12 months.
Welcome to 42 Hollow Oak Road, a captivating 3-bedroom, 2-bathroom sanctuary nestled in the heart of Chappaqua. Spanning 2,380 square feet, this home perfectly balances suburban tranquility with modern convenience. Step inside to discover a bright, airy layout flooded with natural light. The spacious living areas feature warm hardwood floors, fireplace and a seamless flow, ideal for daily living
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
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, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the
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
Welcome to a charming storybook Cape in the award-winning Chappaqua school district. This 3-bedroom, 2-bathroom home is sited on a beautiful, level property and features a 2-car garage attached by breezeway. Freshly painted and move-in ready, this inviting home offers comfortable living in one of Westchester's most sought-after communities. Enjoy the convenience of being just minutes to downtown
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
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,
Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,
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
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
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
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
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,
Experience refined country living in this beautifully crafted custom modern farmhouse, ideally located just minutes from downtown Chappaqua, local shops, restaurants, and the Metro-North train station. Set on a level, private property, this thoughtfully designed home blends timeless charm with modern comfort.The main level features a spacious primary bedroom suite, offering the
Beautifully renovated second-floor 2-bedroom, 1-bath apartment just a short walk to the Chappaqua train station, downtown shops and restaurants. This light-filled home offers approximately 1,200 square feet of thoughtfully updated living space featuring hardwood floors throughout, a stunning designer kitchen with quartz countertops, stainless steel appliances, shaker cabinetry, subway tile
Move right into this spacious Chappaqua end-unit condominium, ready for immediate occupancy. Located just a short distance from town, shops, restaurants and Metro-North, this sought-after community offers exceptional amenities, including a swimming pool, fitness center, tennis courts and clubhouse. One of the largest homes in the complex, this light-filled residence features three bedrooms and
Imagine starting the morning with a stroll into the heart of Chappaqua for coffee, having the Metro North station just moments away, and returning home to the ease of condominium living complete with an inground pool and tennis courts. Welcome to Chestnut Oaks, an ideally located Chappaqua community offering convenience, space and wonderful amenities.This spacious one bedroom residence
Welcome home to this charming, fully renovated rental nestled in Chappaqua and surrounded by beautifully landscaped grounds. This inviting home features 3 bedrooms, 2 full bathrooms, and a versatile den ideal for a home office, playroom, or additional living space. The bright and welcoming living room is centered around a cozy fireplace, creating the perfect place to relax and unwind. Enjoy your
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
Welcome to this pristine 2-bedroom Cape Cod-style home , offering a versatile layout that effortlessly lives like a 3-bedroom. Exuding charm and meticulous care throughout, the residence features 2 full bathrooms and a convenient half-bath. Its center-of-town location puts local shops, dining, and community conveniences right at your doorstep, making it a perfect blend of style, comfort, and
Spacious and sun drenched 3 bedroom, 2.5 bath townhouse with an attached 1 car garage, private driveway, and abundant storage in the highly desirable Old Farm Lake community, located within the award winning Chappaqua School District. This bright, updated, and well maintained home offers comfortable living space, thoughtfully designed for both everyday living and entertaining. Enjoy a private
Move In Ready, Recently Remodeled Townhouse in Old Farm Lake, Chappaqua. Discover this beautifully updated end unit townhouse offering 3 bedrooms, 3 baths, one car garage, deck, and a bonus room on each level. With a natural organic feel to compliment quiet community settings and landscaping, your new home offers calming sensory attentive features throughout to fit any mood. Enjoy New Designer
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