Living in Chappaqua: A Lifestyle and Real Estate Guide to Chappaqua, New York

High-end hamlet in a picturesque, wooded setting just 45 minutes from Midtown Manhattan

What and Where Is Chappaqua, New York

Part of the Town of New Castle in Westchester County, New York, the historic hamlet of Chappaqua is on the east bank of the Hudson River between Millwood and Mount Kisco. Midtown Manhattan is just 35 miles south. The commute to Grand Central Terminal takes just 45 minutes from Chappaqua Metro-North Railroad Station in the heart of town. By car, it’s just under an hour via Interstate 87 or the Saw Mill River Parkway and NY-9A S/Henry Hudson Parkway.

Chappaqua may be small (the hamlet is less than a square mile and has a population of just 1,434), but there’s no shortage of activities for the whole family, whether its playing golf, softball, or tennis; attending a live concert at Chappaqua Performing Arts Center; or shopping in the walkable downtown or at Chappaqua Crossing. The town of New Castle, which includes both Chappaqua and Millwood, encompasses nearly 550 acres of conservation land and green space, including public parks, managed state forests, and nature preserves.

Historical Chappaqua

The name Chappaqua originates from the First Peoples word meaning “the rustling land,” for the sound of the wind rustling through the trees. The hamlet was founded in the 1730s by a group of Quakers from Long Island, New York, who moved north to settle in the area known as "Shapequaw" (Chappaqua) and at Wampus Pond (now part of Armonk).

The Quaker Meeting House, the oldest documented building in the town of New Castle, and the original Quaker cemetery are designated national historic monuments. During the Revolutionary War, the Chappaqua Friends Meeting House served as a field hospital for George Washington’s soldiers wounded in the Battle of White Plains on October 28, 1776. Members of Chappaqua Friends Meeting House were abolitionists and participated in the Underground Railroad decades before the Emancipation Proclamation of 1863.

Before Bill and Hillary Clinton relocated to this quiet corner of Westchester in 1999, Horace Greeley, the 19th-century journalist, presidential candidate, and civil rights advocate, had long been Chappaqua’s most famous resident. Several buildings and landmarks throughout the town bear his name, including Horace Greeley High School, Greeley Woods, the Horace Greeley Statue, and the Horace Greeley House.

In 1853, Greeley built his country estate on 78 acres occupying what now comprises central Chappaqua. The original Greeley homestead, “The House in the Woods,” was located near a brook at the southern boundary of the property. In 1864, Greeley moved his family to an elegant, two-story shingle-style farmhouse at 100 King Street: The Horace Greeley House is now a museum maintained by the New Castle Historical Society and houses an extensive collection of historical memorabilia, artifacts, documents, and a prehistoric mammoth skull.

Three other properties, all listed on the National Register of Historic Places, are closely associated with Horace Greeley or his family and are situated on sites formerly part of the old Greeley farm in Chappaqua:

Rehoboth, a three-level, neo-Gothic barn built by Horace Greeley in 1857, is one of the first concrete structures in the United States. In the 1870s, Greeley’s daughter Gabrielle commissioned architect Ralph Adams Cram to remodel the barn as a private residence.

The Church of Saint Mary the Virgin was built by Gabrielle Greeley and her husband, the Reverend Dr. Frank Montrose Clendenin, as a memorial to their daughter Muriel. Set within a grove of evergreens on the Greeley homestead, the Gothic Revival building, constructed of fieldstone from the Greeley Farm, is a replica of a 13th-century English church of the same name in Monken Hadley in the London Borough of Barnet.

The Chappaqua Railroad Station and Depot Plaza was built on land from the Greeley farmstead. In addition to the 2.5 acres for the depot and plaza, Gabrielle Greeley also gifted land for an approach road (named Woodburn Avenue in honor of Horace Greeley's mother). The station was completed in 1902, connecting the hamlet to Grand Central Terminal in New York City. The original depot was reimagined as a restaurant, now Bobos’ Cafe. The station grounds also host outdoor events, such as the Chappaqua Farmers Market (Saturdays 8:30 a.m. to 1:00 p. m.) and the annual Halloween “Ragamuffin Parade and Carnival.”

Top-Rated Schools in Chappaqua

Chappaqua School District serves 3,653 students in grades K-12 with a student-teacher ratio of 12 to 1. The district’s six schools include Douglas Grafflin Elementary School, Roaring Brook Elementary School, West Orchard Elementary School, Robert E. Bell Middle School, and Seven Bridges Middle School, and Horace Greeley High School. In 2020, U.S. News & World Report ranked Chappaqua’s three elementary schools in the state’s top 75 and its two middle schools in the top 20. Horace Greeley High School consistently rates as one of the best public high schools in the country. Last year it was ranked 195th in the United States (out of 17,857 schools) and 23rd in New York state, with an overall score of 98.91/100. More than 10 percent of graduating seniors are awarded the National Merit Scholarship.

Private schools in the area include The Hackley School; Rippowam Cisqua School, The Masters School; Rye Country Day School (all pre-K to grade 12), and The Harvey School (grades 6 to 12).

Sophisticated Town-and-Country Living

Chappaqua offers a refined town-and-country lifestyle in one of New York’s most affluent zip codes: 10514. Niche.com named Chappaqua the No. 1 place to buy a house in the New York City area. According to redfin.com, home sales went up by 21.6 percent in 2020. The current median house value is US$696,600 and the median rental is US$2,737 per month.

Historic Architecture in Chappaqua

The Old Chappaqua Historic District on Quaker Road was listed on the National Register of Historic Places in 1974. The 12 homes of the original Quaker settlers are clustered around the Friends Meeting House. Further along Quaker Road are restored 18th-century Colonial-style farmhouses, and Gothic and Greek Revival mansions with long driveways and several acres of private grounds. There are two private homeowners’ associations in Chappaqua, Lawrence Farms East and Lawrence Farms South; both are quiet, leafy neighborhoods near Horace Greeley High School. Other sought-after areas include the quiet, tree-lined roads between Mount Kisco Country Club, Whipperwool Park, and Glazier Arboretum Park.

Retail Therapy and Cultural Attractions

Chappaqua has a wealth of family-friendly recreation. Gedney Park is a 126-acre park offering miles of hiking trails, ball fields, green spaces, playgrounds, and even a sledding hill. Croton Gorge Park encompasses more than 97 acres of conservation land for fishing, hiking, and cross-country skiing. Hardscrabble Wilderness Area is a city-run nature reserve with over 235 acres of picturesque grounds with a pond and dog-friendly hiking trails.

The 169-acre Whippoorwill Park was originally part of a private 500-acre game reserve owned by Henry Berol, chairman of the Berol Corporation. It is designated as passive parkland and its 2.5-mile perimeter loop is a popular spot for hikers.

Pinecliff Audubon Sanctuary is one of eight nature preserves run by Saw Mill River Audubon, an environmental organization that protects over 300 acres of wildlife habitat in Westchester County. The seven-acre property has a quarter-mile accessible boardwalk through a red maple swamp. The sanctuary is open to visitors free of charge, seven days a week.

Chappaqua Swim and Tennis Club is a private, family-friendly summer club offering swimming, diving, tennis, and platform tennis. For the traditional country club experience, there are two members-only clubs within a five-minute drive: Mount Kisco Country Club is a family-oriented club with an 18-hole golf course, five Har-Tru tennis courts, paddle tennis courts, a swimming pool, and clubhouse. Whippoorwill Club in Armonk, New York, is a 170-acre country club with one of the top golf courses in the Northeast.

In the summer, the downtown gazebo features live music and entertainment and children’s activities. Another popular spot is the Chappaqua Farmers Market (at the railroad station), open every Saturday, year-round.

Chappaqua Crossing is an upscale retail village on the site of the former Reader’s Digest headquarters founded by DeWitt Wallace in 1922. The 115-acre mixed-use community has a Whole Foods Market, a community arts center, conference center, commercial offices, a medical center, luxury apartments and Georgian-style townhomes. Amenities include two fitness rooms, a club room, and a complimentary shuttle to the Metro-North train station in downtown Chappaqua.

For retail therapy, House of 29 Lifestyle Boutique By Sarah on South Greeley Avenue is a vintage emporium selling fine jewelry, fashion jewelry, clothing, and accessories. The Cosmetic Boutique & Medical Spa specializes in high-end makeup, skin care lines, and professional medical aesthetics.

Dining in Chappaqua

Crabtree’s Kittle House Restaurant & Inn

Crabtree's Kittle House Restaurant & Inn offers a taste of Old New York. Constructed in 1790, this elegant house on Ivy Hill formerly served as a post-Revolutionary farm, a Prohibition roadhouse, and a private girls’ school. The Crabtree family continues the property’s legacy with local, farm-to-table cuisine and outstanding service.

Le Jardin Du Roi

Le Jardin du Roi is an authentic French bistro in the heart of town offering breakfast, lunch, and dinner. According to a New York Times review, “the decor is shabby-chic Parisian...the food is both artful and robust, the service engaging and attentive.”

Chappaqua also offers a range of international fare, including a taste of Italy at Old Stone Trattoria, Spanish tapas at Ibiza Kitchen, and sushi and Asian fusion cuisine at Waka Asian Bistro.