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.
1/2
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.
1/8
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.
1/14
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.
1/4
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 .
1/8
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
Urs Klarer,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Chappaqua, NY sell after 36 days on the market compared to the national average of 49 days. The median sale price for homes in Chappaqua, NY over the last 12 months is $1,550,000, up 24% from the median home sale price over the previous 12 months.
REINTRODUCING 50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors, and beautiful staging, this one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the
Charm. Character. Convenience. Beautiful curb appeal! Welcome home to this wonderful home with rocking chair front porch. Original owners who built this delightful home in 1996. Impeccable 3 bedroom, 3.5 baths Traditional Colonial located in the heart of Chappaqua with level backyard. This home is better than new, it has been extensively renovated in the past 2 years. This modern home has it all:
Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom
REINTRODUCING 50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors, and beautiful staging, this one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the
Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.Inside, the open, sunlit layout features oversized windows that invite the outdoors in, 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
Move right in this updated 3-bedroom townhouse at Old Farm Lakes in Chappaqua, a beautiful renovated condo near everything. First floor: foyer, powder room, updated kitchen with stainless steel appliances, and patio. Large dining/living room with a wood-burning fireplace. Office/den with a walk-out to the deck. Second floor: primary bedroom with a large walk-in closet, en-suite bath featuring a
Large bright 1Bedroom plus loft in a two story apartment in Chestnut Oaks Condominium. Washer dryer in the unit. Wood fireplace. Short walk to the downtown center and train station. Complex offers Community Pool and Tennis. One car garage included, plus there is unassigned parking and guest parking. Tenant pays all utilities.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
