For many who are leaving the city and considering the NYC suburbs, one of the biggest hesitations is losing the walkability that the city offers and becoming isolated in a home away from conveniences. If you are looking for a home that is still within walking distance to the downtown amenities, schools and parks, there are a handful of towns we suggest exploring. Below are some of the most walkable towns in Westchester and Fairfield County.


This sought after Rivertown features a charming and lively downtown that is full of mom-and-pop shops, musical and cultural events, and diverse dining options. The train is situated near the waterfront along with the Scenic Hudson RiverWalk Park, which just another draws to this scenic and walkable village. New construction luxury townhouses and condos are sprawled along the waterfront while the streets surrounding downtown offer a single family homes within walking distance to the downtown amenities. If you’re looking for a character rich town with walkable features and an easy commute to the city, Tarrytown may be fit for you.


A small town with a large personality. Anyone from singles and young families to empty nesters will enjoy the quaint shops, cultural events, entertainment that this hip village has to offer. With the many of the town’s amenities spread across the stretch of downtown, you’ll discover new and exciting spots depending on the direction you explore. Touted as a “walk to all” town, the tree-lined streets are full of homes on compact lot sizes. Plus, Pleasantville is desirable location within the county, convenient to major highways and surrounding cities and shopping hubs.


As a quaint village with two separate downtown areas, this shoreline village offers walkability for many of life’s daily activities. From walking kids to school and their after school activities to everyday errands and shopping trips, you’ll find homes that accommodate this lifestyle. The train is also within walking distance for a convenient commute to the city. The town’s quiet sophistication along the Sound Shore appeals to many city transplants looking to ease into suburban living.

White Plains

As a centralized location with one of the county’s most diverse mix of housing options, White Plains is an ideal destination for those who still long for a city vibe. From co-ops and condos in the heart of the downtown, to single family homes on tree lined streets within city limits, there is a home and lifestyle for just about anyone. Its extremely walkable downtown is home to many commercial offices, a diverse mix of restaurants, and prime shopping malls. Plus, a quick 35 minute commute makes this neighborhood extra appealing for those still traveling to the city


Within this Northern Westchester hamlet, you’ll find a community that is full of pride for maintaining their heritage and small town appeal. Quaint yet energetic, the downtown has a variety of established and new mom and pop shops, artistic and cultural events, and plenty of green space for exploring. Being within walking distance to the village and train is a beloved lifestyle that many long to achieve. The surrounding homes are on picturesque streets and full of character, and the walkability to town allows residents to stay connected to the heart of this village. 


If you’re looking for true walkability, look no further than Downtown Stamford. With a true city vibe, you can have restaurants, shopping and entertainment within steps from your front door. 

Due to its flourishing restaurant and bar scene, Stamford attracts many young individuals, with Harbor Point recognized as the main entertainment area. Located directly on the Long Island Sound, Harbor Point is considered a “Live-Work-Play” community with an abundance of shopping and dining options. The Harbor Point Trolley is the most exciting way to get around the city, which runs everyday and makes 14 stops throughout - and best of all, it's free. 

Cos Cob

With only about 7,000 people and with a size of only 4.5 square miles, Cos Cob is an intimate and convenient community. Playgrounds, the post office and the terrific public library are often no more than a five-minute stroll away, and it is not uncommon to see people making their way there on the shoulders of roads, undeterred by the occasional lack of sidewalks. The town’s commercial hub, which houses coffee cafes, gourmet cheese shops, upscale juice bars and numerous dining options, is bordered by residential neighborhoods on both sides, allowing families to enjoy a variety of options only minutes from their doorsteps. 

New Canaan

New Canaan is a beautiful town that attracts many young families due to its highly rated public school system and its popular town center. You can find a classic colonial home or modern masterpiece within walking distance to fine restaurants, boutiques, antique shops, a movie theater, and interior design shops. Elm Street is considered the heart of downtown and from there you can walk up and down small alleyways to find hidden gems.  Surrounding town you can find a mix of newly built luxury townhouses that could cost as much as $3 million, as well as more modest condos, ranging from $350,000.

So if you’re considering leaving the city to explore life in the NYC suburbs, one of these towns may be a good option for you. They provide all of the charm and serenity of suburban life without sacrificing convenience. If you’re interested in learning more about any of these towns, reach out to us today. 

Take our quiz to find out which neighborhood best fits your personality or head over to our neighborhood guides to learn more about the lifestyle and appeal of other wonderful towns in the NYC suburbs.

Brought to you by Brittany + Christa


We're not your typical real estate agents. As former city dwellers, we appreciate the qualities that make city lifestyle so unique, from the convenience of walking to your favorite restaurant or corner store to the vast and diverse cultural and entertainment activities. But we’ve also experienced the challenges and frustrations that are motivating you to seek change. During our transition from the city to the suburbs, we had the same thoughts, concerns and questions, prompting us to create a better way to navigate the suburban home search process for others.