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
Alicia Goldman,
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.
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On average, homes in Chappaqua, NY sell after 38 days on the market compared to the national average of 54 days. The median sale price for homes in Chappaqua, NY over the last 12 months is $1,600,000, up 3% from the median home sale price over the previous 12 months.
Updated end-unit townhome with an oversized patio, featuring 3 bedrooms, 2.1 baths, and a spacious loft in the sought-after Apple Hill Farm complex. Airy and private. Tranquil setting among apple orchards and woody walking trails by the pond. This beautiful unit has been extensively renovated and offers hardwood floors throughout, fresh paint, an updated kitchen with stainless steel appliances
A Timeless Colonial, Thoughtfully Reimagined for the Way We Live Today There is a certain feeling you get the moment you arrive, a sense of history, warmth, and quiet refinement. Set on a lush, level acre within the coveted Chappaqua School District, this stately Colonial has been beautifully renovated to honor its classic roots while embracing modern comfort and flexibility. The home’s striking
Immaculate townhouse in a desirable walk-to-town location close to shops, restaurants, and the train. Refinished maple hardwood floors, custom built-ins, and a fireplace define the main living level, highlighted by a dramatic wall of windows with sunset views. Newer Pella sliders open to a private deck for seamless indoor-outdoor living. Custom stair railings, upgraded solid interior doors, and
Updated end-unit townhome with an oversized patio, featuring 3 bedrooms, 2.1 baths, and a spacious loft in the sought-after Apple Hill Farm complex. Airy and private. Tranquil setting among apple orchards and woody walking trails by the pond. This beautiful unit has been extensively renovated and offers hardwood floors throughout, fresh paint, an updated kitchen with stainless steel appliances
Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two
Meticulously maintained, beautifully appointed 4-bedroom, 4 full and 1 half-bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal
Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an
A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment,
Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected.The main level makes an immediate impression with a dramatic
This classic center hall Colonial sits across the street, just steps from Gedney Park - one of the area’s most beloved parks, offering direct access to trails, fields, a playground, a sledding hill, a fishing pond, and year-round recreation. Inside, enjoy a sunlit living room with a wood-burning fireplace, French doors to a 3-season porch with new vinyl flooring, and refinished wood floors
Experience the art of living well in this extraordinary private retreat overlooking Heaptaugua Lake. Set on just under five acres, the property offers total serenity while remaining just minutes from Chappaqua’s quaint downtown, restaurants, Metro-North, and shopping. Enter through the gates and follow the sweeping driveway as it curves past the pool house and pool, passing a sweeping lawn before
Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides
A Timeless Colonial, Thoughtfully Reimagined for the Way We Live Today There is a certain feeling you get the moment you arrive, a sense of history, warmth, and quiet refinement. Set on a lush, level acre within the coveted Chappaqua School District, this stately Colonial has been beautifully renovated to honor its classic roots while embracing modern comfort and flexibility. The home’s striking
Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new 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
Welcome to the Jonathan Tompkins House, a true New Castle landmark dating back to 1750 where history and modern living intertwine. Ideally situated in the heart of Chappaqua and located within the award-winning Chappaqua School District, this fully furnished rental weaves centuries of New Castle’s past into its walls. Original hand-hewn beams and stained glass evoke timeless old-world charm,
Charming antique home ideally located in the heart of Chappaqua, just minutes to Armonk, Mount Kisco, major highways, and the Metro-North train station. Features include a bright white kitchen with stainless steel appliances, stone countertops, and tile backsplash, along with beautiful hardwood floors throughout. Enjoy the convenience of in-unit private laundry, private storage, and two driveway
Walk to town shops, restaurants, park, library, community garden, farmers market and commuter train from this conveniently located well established condo complex in the heart of Chappaqua. Bright, sunny, meticulously maintained ground floor one level unit is move-in ready and features a fireplace, patio, recessed lighting, renovated kitchen with quartzite counters, renovated bathroom and ample
Spacious, light filled townhouse close to restaurants, town and train. Features include a large great room with fireplace, walls of glass and sliders to large balcony. A kitchen, separate dining room , powder room and laundry complete the first floor. The 2nd floor offers a spacious primary with en suite bath and a 2nd private bedroom with en suite bath and loft space.2 assigned spaces and
Bright one=bedroom accessory apartment in Chappaqua. Open floor plan gives a spacious feel. Sliding glass door opens to large deck running the length of the unit. Enjoy beautiful vistas in this private setting. Heat, electricity, water, trash and snow removal included in the rent. Driveway parking available for one car. Home is equipped with a generator in case of power outage. No pets allowed.
Picture perfect center hall colonial. Ideal executive rental, walk to town and train. Living room with fireplace, dining room with sliders to large deck, and modern eat-in kitchen. Bedroom and full bath on first level, perfect for au-pair or guest suite. Primary bedroom with en-suite bath, featuring double sink vanity, jacuzzi tub and stand alone shower. Two more hall bedrooms, well-appointed
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