Nestled in the wooded hills of northern Westchester County, Chappaqua has long been one of the most coveted communities in the New York metropolitan area. This charming hamlet in the town of New Castle combines nationally ranked schools, a walkable downtown village, and abundant natural beauty — all with a direct train commute to Manhattan.
Whether you’re relocating from New York City or considering a move within Westchester, this guide covers everything you need to know about living in Chappaqua.
Why Choose Chappaqua?
Chappaqua offers what few communities can: a nationally ranked school district, a genuinely charming village center, and a wooded, nature-rich setting — all within a direct 47-minute train ride of Grand Central Terminal. Families choose Chappaqua for larger lots and more space per dollar than nearby Scarsdale, without sacrificing school quality or commute convenience.
Chappaqua by the Numbers
Why Chappaqua?
The Chappaqua Difference
Chappaqua delivers a rare combination: the academic prestige of a top-5% school district, the natural beauty of a wooded, semi-rural setting with 126 acres of parkland, and a charming village center with farm-to-table dining and a nationally known farmers’ market — all 30 miles north of midtown Manhattan.
Who Lives in Chappaqua?
Chappaqua attracts families who value education, nature, and community over proximity to the city. The median household income is $241,432, reflecting the community’s affluent, professional character. The population is 64.4% White, 17.6% Asian, with 23.7% of residents born outside the United States — creating a cosmopolitan community with deep local roots.
The median age is 45.8, with a significant concentration of families with school-age children. Homeownership is 76.6%, and the poverty rate is just 1.05%.
Chappaqua’s Distinct Areas
Unlike communities with formally named neighborhoods such as Scarsdale’s Heathcote and Fox Meadow, Chappaqua functions as a unified hamlet. However, distinct areas offer different experiences.
Downtown / Village Center
Character: Walkable, vibrant, commuter-friendly
Best For: Commuters, empty-nesters, walkability seekers
The heart of Chappaqua centers on King Street and South Greeley Avenue. Restaurants, shops, and the library sit within steps of the train station. Homes here offer smaller lots with charming village character and walk-to-train convenience.
Old Chappaqua Historic District
Character: Historic, distinctive, deeply rooted
Best For: History lovers, character-home seekers
Centered around the 1753 Quaker Meeting House, this area was added to the National Register of Historic Places in 1974. Some of the community’s oldest and most architecturally significant homes are found here. Weekly Quaker meetings still connect residents to over 270 years of history.
Northern Chappaqua
Character: Wooded, spacious, private
Best For: Families seeking acreage, privacy, nature
The areas toward Bedford and Chappaqua Crossing offer larger lots, more wooded settings, and a more rural feel. Homes range from renovated historic properties to new custom builds on multi-acre parcels.
Southern Chappaqua
Character: Accessible, value-oriented
Best For: Buyers seeking Chappaqua schools at more accessible price points
The southern sections of New Castle blend toward Pleasantville, offering a mix of housing styles. This area provides good value while still benefiting from the Chappaqua Central School District.
World-Class Schools
Education is the cornerstone of Chappaqua’s identity. The Chappaqua Central School District (CCSD) is nationally renowned, ranked in the top 5% of all school districts in New York State and rated 5 out of 5 stars by SchoolDigger.
District Highlights
Top 5% of all NY school districts | Blue Ribbon award-winning high school | Top 1% math and reading proficiency | 6 schools serving approximately 3,800 students | Actively involved parent community
Elementary Schools by Area
| School | Grades | Highlights |
|---|---|---|
| Douglas G. Grafflin Elementary | K – 4 | Small class sizes, enrichment programs |
| Roaring Brook Elementary | K – 4 | Strong community involvement, dedicated faculty |
| Westorchard Elementary | K – 4 | Academic excellence, creative arts programming |
Middle & High School
| School | Grades | Rating | Key Features |
|---|---|---|---|
| Robert E. Bell Middle School | 5 – 8 | A+ | Advanced coursework, arts and music, competitive athletics |
| Seven Bridges Middle School | 5 – 8 | A+ | STEM focus, project-based learning |
| Horace Greeley High School | 9 – 12 | A+ / Top 1% | Blue Ribbon, ~1,100 students, 96.9% science proficiency, Ivy League feeder |
Horace Greeley High School is the crown jewel — a Blue Ribbon award-winning institution with math and reading proficiency both ranking in the top 1% statewide. Greeley offers an extensive AP program, award-winning performing arts, and competitive athletics. Graduates regularly attend Ivy League and top-tier universities.
Real Estate Market Overview
2025–2026 Market Snapshot
Median sale price $1.4M – $1.5M | Price per sq ft $609 | Market condition Seller’s Market | Year-over-year trend Up 1.8% – 16.3% | Price range $500K – $5M+
Chappaqua’s real estate market remains competitive, driven primarily by school district demand. Homes range from condos and smaller properties starting around $500,000 to luxury estates exceeding $5 million on multi-acre parcels.
Types of Homes
- Colonial homes: The most prevalent style, from classic center-hall to Dutch Colonial, many with period details and mature landscaping
- Tudor homes: Distinctive half-timbered facades found throughout, particularly near the village center
- Contemporary builds: Newer construction with open floor plans, walls of glass, and modern amenities on wooded lots
- Ranch homes: Single-story options popular with empty-nesters and those seeking accessibility
- Luxury townhomes: Chappaqua Crossing Carriages by Toll Brothers offers 91 Georgian-style townhomes starting at ~$1.2M with five floor plans (Briarcliff, Greeley, Millwood, Millwood Elite, Byram)
- Estates on acreage: Larger lots of 1–5+ acres available, particularly in northern sections toward Bedford
Market Insight
Chappaqua offers significantly more land and home per dollar than Scarsdale ($1.4M vs $2.1M median), making it one of the best values in Westchester for families prioritizing top-tier schools with generous lot sizes.
Commute & Transportation
Metro-North Railroad
Chappaqua Station sits right in the village center on the Harlem Line. Direct service to Grand Central Terminal in approximately 47 minutes, with trains running hourly and more frequently during peak commute hours. One-way fares: $11–$17. Commuter parking available with permit and metered options. Many residents walk to the station.
By Car
The Saw Mill River Parkway runs through the area, connecting to I-87 (New York State Thruway) and the broader Westchester parkway network. Driving to midtown Manhattan takes approximately 45–75 minutes depending on traffic.
Nearby Airports
Westchester County Airport (HPN) is approximately 15 minutes away, with JFK, LaGuardia, and Newark all accessible within 45–90 minutes.
Lifestyle & Recreation
Downtown Dining
Crabtree’s Kittle House — built in 1790, internationally renowned for its Wine Spectator Grand Award wine list and farm-to-table cuisine. Basso by PXK — contemporary Italian at 11 King Street under Chef Peter X. Kelly. Le Jardin du Roi — beloved French-American bistro known for award-winning BBQ and all-day breakfast. Plus dozens of cafes, bakeries, and casual dining along King Street.
Chappaqua Farmers’ Market
One of Westchester’s best, drawing foodies from across the county with local produce, artisanal foods, craft beer, hot sauce, dumplings, and specialty items.
Gedney Park
126 acres of hiking trails, ballfields, playgrounds, and open space — the community’s premier outdoor gathering spot year-round. Nearby Whippoorwill Park adds 169 acres of woodland trails with rocky ridges, stream crossings, and wetlands.
Arts & Culture
Chappaqua Performing Arts Center brings diverse programming. The Children’s Book Festival is the largest in the tri-state region, drawing nationally known authors. The Chappaqua Library serves as a community hub with programming for all ages.
Country Clubs
The Whippoorwill Club, founded in 1928 on the second-highest point in Westchester County, features a Donald Ross-designed course ranked #73 among the best classic courses in the United States. Other private clubs in the New Castle area offer tennis, swimming, and dining.
Community Comparison
| Chappaqua | Scarsdale | Pleasantville | Armonk | |
|---|---|---|---|---|
| Median Price | $1.4M | $2.1M | $800K | $1.3M |
| Commute to GCT | 47 min | 35 min | 55 min | 50 min |
| School District | Chappaqua CSD | Scarsdale UFSD | Pleasantville UFSD | Byram Hills CSD |
| Character | Wooded, nature-rich | Walkable village | Compact, artsy | Country estates |
| Lot Size | Large (0.5–2+ acres) | Moderate | Smaller | Very large |
| Best For | Families wanting space + top schools | Walkability + prestige | Value + village charm | Privacy + country living |
Notable Facts
- Founded by Quakers in the 1730s: The 1753 Meeting House still holds weekly meetings today
- Home of the Clintons: Former President Bill Clinton and Secretary of State Hillary Clinton purchased their Dutch Colonial home for $1.7 million in 1999
- Named for the land: “Chappaqua” derives from a Lenape word meaning “the place of the laurels” or “rustling land”
- Horace Greeley connection: The legendary New York Tribune editor and U.S. congressman lived here, giving his name to the high school
- Nobel Prize town: Physicist Leo Esaki was living in Chappaqua when he won the Nobel Prize for Physics in 1973
- Railroad community since 1846: The New York and Harlem Railroad transformed Chappaqua into a commuter community nearly 180 years ago
- Celebrity draw: Vanessa Williams, Ben Stiller, Kelli O’Hara (Tony Award winner), and former Governor Andrew Cuomo have all called Chappaqua home
- Reader’s Digest headquarters: The iconic magazine was headquartered in Chappaqua from 1939; the 114-acre campus is now the Chappaqua Crossing development
Frequently Asked Questions
Is Chappaqua a good place to live?
Chappaqua is consistently ranked among the best places to live in Westchester County, offering a nationally renowned school district, charming downtown, abundant nature, and a direct 47-minute commute to Grand Central Terminal.
What is the average home price in Chappaqua?
The median home sale price is approximately $1.4 million to $1.5 million, with homes ranging from $500,000 to over $5 million. The median price per square foot is approximately $609.
How are the schools in Chappaqua?
The Chappaqua Central School District ranks in the top 5% statewide. Horace Greeley High School is a Blue Ribbon award-winning school ranking in the top 1% of all New York high schools, with three elementary schools, two middle schools, and strong college placement.
How long is the commute from Chappaqua to NYC?
The Metro-North Harlem Line provides a direct ride from Chappaqua station to Grand Central Terminal in approximately 47 minutes, with trains running hourly and more frequently during peak hours.
What are property taxes like in Chappaqua?
The effective property tax rate is approximately 2.69%, with a median annual tax bill of about $25,896. Residents consistently cite the school quality and community services as justifying the investment.
How does Chappaqua compare to Scarsdale?
Both offer top-rated schools and excellent quality of life. Chappaqua provides more land and a nature-oriented setting at a lower median price ($1.4M vs $2.1M), while Scarsdale offers a more walkable village and a shorter 35-minute commute.
What is Chappaqua Crossing?
Chappaqua Crossing is a mixed-use development on the 114-acre former Reader’s Digest campus, featuring 91 Toll Brothers luxury townhomes starting at ~$1.2 million, 64 apartments, and a retail village anchored by Whole Foods, Life Time Fitness, Starbucks, and Chase Bank.
Ready to Find Your Chappaqua Home?
The Francie Malina Team has sold more homes in Westchester County than any other team since 2021. Let local expertise guide you to the right home in Chappaqua, whether you’re drawn to the village center, a wooded estate, or the new construction at Chappaqua Crossing.
Contact The Francie Malina Team