Armonk is about 10 miles inland from Long Island Sound in Westchester County on the southwestern border of Connecticut and about 40 miles north of New York City. It is one of three hamlets in North Castle—the other two are North White Plains and Banksville. Commuting into New York City involves a 10-minute drive to the North White Plains Metro-North Railroad station, where the Harlem Line will take you to Grand Central Terminal in about an hour. Or you could drive all the way on Interstate-684 to the Hutchinson River Parkway South and into the city via the George Washington Bridge or continue farther east to the FDR Drive.

Bucolic Bedford Village, Bedford Hills, and Katonah—the three hamlets of Bedford, New York— provide estate living less than 2 hours from Manhattan. All three family-oriented hamlets in Westchester County are served by seven highly-rated public schools covering grades K–12. Winding roads through rural neighborhoods feature stone and shingle-style colonial homes on large lots, or manor estates behind gated entries on large acreages. The rural hamlets are known for their remove from the pressures and pace of the city, making them popular enclaves with celebrities past and present—and home to those who seek a lifestyle of grace and quietude and have the means to create it.

Tudor and Colonial homes set back from lushly landscaped lawns characterize the village of Bronxville, New York. While the village has the look and feel of the English countryside, it is an easy 40-minute commute to Manhattan—a trip more than half its residents make every weekday. One of the community’s early 20th-century developers, William Van Duzer Lawrence, also founded Sarah Lawrence College in 1926 on the grounds of his estate. Natural and architectural splendor abound in Bronxville and allow residents the sense of a rural lifestyle without sacrificing any of the cultural or professional opportunities of New York City.

The picturesque hamlet of Chappaqua is part of the town of New Castle in northern Westchester County, New York. Although small (less than half a square mile), the hamlet has much to offer in the way of culture and recreation. It’s also known for its celebrity residents; most notably Bill and Hillary Clinton, who’ve lived in the town since the 1990s. Chappaqua has a historic, walkable downtown, high-end restaurants and shops, popular weekend farmers’ market, and world-class performing arts center. Historic homes set within woodland, scenic parks and nature trails, golf courses, country clubs, and one of the highest-ranked school systems in the United States, all just an hour’s drive, or a 45-minute train journey, to Midtown Manhattan. Westchester County Airport is a 20-minute drive.

Montebello, New York, began as an experiment in self-sustenance and communal living as an alternative to the unemployment, poverty, and other hardships city-dwellers faced during the Great Depression. The experiment faded in the post-World War II years, though its stone structures still lend character to the village that was formally incorporated as Montebello in 1986. The name means beautiful mountain and it’s appropriate: the village, which lies between Suffern, New York, and Palisades Park, New Jersey, has beautiful views of the Ramapo Mountains. Montebello is decidedly rural living and a lifestyle choice given the 70-minute commute into Manhattan and an entertainment venue that features outdoor activities over dining out, cinema, or shopping, which are all available in nearby villages and shopping malls.

Mount Vernon, New York, in Westchester County is just north of the Bronx, the northernmost borough of New York City, but is still considered an inner suburb of the city—as opposed to the leafy hamlets, villages, and towns that populate the rest of the Westchester County. The south side of Mount Vernon is closer to the Bronx in geography as well as look and feel and much more urban than the northern part of the city, which is largely residential. Mount Vernon’s civic and commercial district is in the southern part of the city too.

Nanuet is a hamlet of almost 19,000 residents in the town of Clarkstown in the center of Rockland County New York. The community is centered between Spring Valley to the west, Pearl River to the south, West Nyack to the east, and New City to the north.

New City, an affluent hamlet in the city of Clarkstown, New York, has a distinguished history, ample green space and parks, and plenty of local charm. It is ideal for community for commuters, thanks to its proximity to New York City, just 45 minutes’ drive. Palisades Interstate Parkway runs through the southwest corner of the town, and route 9W wraps around the east, separating it from the Hudson River and Hook Mountain State Park. New City is renowned for its outstanding public school system. Excellent across all grades, K-18, its high schools rank highly on college readiness and participation in Advanced Placement courses.

North Salem, New York, a town tucked away in the North East corner of Westchester is known for its horse country, open land, and stone walls. The town is full of colonial equestrian estates with lots of open space. For commuters from Manhattan, it is a short 55 mile trip. MetroNorth has two convenient train stations available. North Salem is not only home for locals but also is a home for weekenders, equestrians, and nearby neighbors.

An hour’s commute via car to Midtown Manhattan, Nyack comprises five villages, which are spread across two towns in Rockland County, New York. Formerly a shipbuilding and manufacturing center, the town is now a suburban haven of Cape Cod and colonial homes, nature parks and walks along the Hudson River, chic cafés and eateries . From elegant country estates to luxury condos near the village center, any of the villages named Nyack offer art and soul on the Hudson.

Once immersed in this small town, one can see the deep pre-Revolutionary War roots that run throughout Ossining, New York. This three-square-mile village on the Hudson River was named “the Best Place for Architecture Admirers in Westchester” by Westchester Magazine. Ossining’s famous residents have included John Cheever, writer and winner of the 1979 Pulitzer Prize for Fiction, and actress Anne Francis, as well as the fictional character Don Draper, from the AMC television series Mad Men. Today, the town has a diverse population of approximately 25,000 residents.

Port Chester is a 2.4-mile coastal village within the town of Rye in Westchester County, New York. Nicknamed the “Gateway to New England,” Port Chester borders the state of Connecticut; just east is Greenwich, one of the most affluent cities in America. Port Chester evolved from an industrial town to a major seaport in the 19th century due to its location along the Byram River. Today, it’s an attractive suburban village with a scenic waterfront; parks and recreation areas; a historic downtown with a theater, galleries, fine shops, and excellent restaurants; and a train station with direct service to Midtown Manhattan. Port Chester has six parks, waterfront plazas, and a pedestrian-friendly downtown, making its “Walk Score” 78/100—higher than Washington, DC, Chicago, and Seattle.

Pound Ridge, New York is a small town about 50 miles outside Manhattan or, as they say, 50 miles and 50 years away from the hustle of the Big Apple. Well, they don’t say it, but it’s the distinct feeling one gets when venturing north from the city for a day of Americana.

Rye Brook is part of the town of Rye in Westchester County, New York. This close-knit village on Long Island Sound is just 40 minutes’ commute from Midtown Manhattan. The village has much to offer: a scenic location close to the beaches of Long Island Sound; outstanding recreation, shopping, and dining; highly rated schools; and a safe, family-friendly environment. Rye Brook has more than 100 acres of green space, comprising sports fields, public parkland, and nature preserves. The village is a designated Tree City USA, which is part of the USDA Forest Service program to encourage superior forestry stewardship. It’s also in one of the Northeast’s most coveted residential areas, neighboring the affluent towns of Rye, Purchase, and Greenwich, Connecticut.

Rye, New York, offers a variety of lifestyles from the purely rural, to small-town suburban, to seashore vistas. And it’s still an easy hour-long commute to Grand Central Terminal in Midtown Manhattan. The town’s claim to fame lies in its history. The Boston Post Road runs through the town, creating a National Historic District; Rye Playland is an Art Deco National Historic Landmark and has one of the oldest wooden roller coasters in the country. The schools in Rye are highly regarded and support the needs of families. Rye is a coveted zip code for those who want—and need—access to all Manhattan offers but require the space and choice suburban living along Long Island Sound can provide.

Smart. Sophisticated. Chic. All describe Scarsdale, the upscale suburb of 18,000 residents just 20 miles outside New York City, north of Bronxville and south of White Plains in the heart of Westchester County. Its public schools are among the best in the country, with low student-teacher ratios and high academic performance averages. The luxury residential market predominates real estate in Scarsdale—and is the prime impetus for choosing life in this New York City suburb. Shopping and restaurants match the varied needs of the population as do the conservation areas for nature lovers and the cultural attractions for those who want it all where they live. And living in Scarsdale offers country estates, gated communities, and tree-lined in-town neighborhoods with lush landscaping.

History and humanity define Tarrytown, New York. A village in Westchester County on the east bank of the Hudson River, Tarrytown provides suburban living less than an hour from Midtown Manhattan. Settled by the Dutch in the 17th century, inspiration to the Hudson River School artists of the 18th century, provider of safe houses along the Underground Railroad in the 19th century, home to John D. Rockefeller and other notable industrialists in the 20th century—and now a thriving enclave offering country manor living, good schools, an easy commute to New York City, and a variety of dining and shopping experiences for refined 21st-century living.

Tuxedo Park, a hamlet in the town of Tuxedo in Orange County New York, lent its name to the formal wear, not the other way around, at the turn of the 20th century. The hamlet is tiny—only 800 residents—and remains a gated community as it has since its founding in the late 18th century. Nestled in the shadows of the Ramapo Mountains, the hamlet’s second claim to fame, after becoming synonymous with satin-striped trousers and cummerbunds, is as the birthplace of the shingle-style of architecture that inspired the Modernists, most notably expressed by Frank Lloyd Wright.

White Plains, New York, a city of nearly 60,000 residents, is considered one of the best places to live in the United States. The schools—nine public schools for grades K–12—are served by White Plains’ own school district and are consistently highly rated. Since the Bronx River Parkway connected Westchester County to the rest of the world, namely New York City, in 1906, White Plains grew and thrived; it also is the county seat of Westchester. Numerous international and national company headquarters are within White Plains for those who want to live and work in the same area; for commuters to Midtown Manhattan, there are two Metro-North Railroad stations for the 25-mile trip. The small city offers estate living in its surrounds and, within the city, in landscaped neighborhoods with stately architecture.