The Stranger Next Door

Do any of these contiguous communities share anything besides borders, or are they as different as they seem?

City photos by Ken Gabrielson

Do these contiguous communities share anything besides borders, or are they as different as they seem? Westchester Magazine investigates.

— Rye/Port Chester —


Rye and Port Chester are both nestled along beautiful Long Island Sound, with easy access to highways and a quick train ride to Manhattan. Both have a strong sense of pride, yet in many respects, these neighboring communities in Southern Westchester couldn’t be more different.

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The city of Rye, incorporated in 1942, is Westchester’s smallest city (6 square miles). An affluent bedroom community with 16,000 residents, Rye has a charming Insta-worthy downtown with high-end boutiques, salons, and fashionable, upscale restaurants.

While the median sales price for single-family homes is $1,850,000, properties regularly sell for more than $5 million. In 2015, Forbes ranked Rye as the most expensive town in Westchester County. Approximately 83 percent of Rye’s population is white.

With an award-winning school system, Rye attracts city dwellers seeking a top-notch education in a bucolic, suburban setting. Rye High School (approximately 1,000 students) was ranked #20 in New York State and #114 nationwide by U.S. News & World Report’s “Best High Schools 2018.”

In stark contrast to Rye, the village of Port Chester is a vibrant, bustling community that’s more working-class and immigrant-centric than its quieter neighbor (the village’s former name was the-not-so-elegant Saw Pit, named so after its shipbuilding industry). When downtown Rye calls it quits, around 10 p.m., Port Chester is just getting started, thanks in part to the renowned 1,800-seat Capitol Theatre. The historic venue that opened in 1926 and became a catering hall in 1997 was reopened as a concert venue in 2011. During the 1960s and ’70s, the Grateful Dead, Janis Joplin, and Pink Floyd graced the stage — more recently, Steve Winwood, Phish, Neil Young, Foreigner, Courtney Love, and Bob Dylan have rocked the iconic theater.


Population: 16,000
Median Age: 42.5
Race: White: 83.2% Hispanic: 7.4% Asian: 5.4% Black: 0.3%
Median Household Income: $168,954
Persons in Poverty: 3.3%
Persons With a Bachelor’s Degree or Higher: 73.2%

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Port Chester

Population: 29,522
Median Age: 36.5
Race: Hispanic: 59.4% White: 31.6% Black: 5.3% Asian: 2%
Median Household Income: $58,807
Persons in Poverty: 12.9%
Persons With a Bachelor’s Degree or Higher: 22.2%

*Stats from

Port Chester

Incorporated in 1868, Port Chester spans 2.4 square miles, yet its population (roughly 30,000) is almost twice that of Rye. Approximately 60 percent of its residents are Hispanic. The median household income is $58,807 (compared with Rye city’s $168,954), while the median sales price for single-family homes ($485,000) is significantly lower than in Rye, and roughly 13 percent of residents live below the poverty line.

A major revitalization of Port Chester’s waterfront began in 1999, and today it boasts a multiplex theater, retail, and restaurants — including the recently opened Colony Grill and Bona Bona Ice Cream. Like Rye, Port Chester’s downtown has numerous fashionable dining-out options (e.g., Tarry Lodge, Saltaire, Sonora, Capers) but has essentially outpaced Rye as a local foodie mecca, with a pastiche of eateries serving a greater breadth of cuisine — including Moroccan, Peruvian, Mexican, Colombian — to an ethnically diverse clientele.

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Despite their differences, both towns foster a strong sense of community pride and are grateful for each other’s contributions. Port Chester police chief Richard Conway, a longtime Rye resident, says spirit runs high in both towns — citing the famed Rye-Harrison football game (a 90-year rivalry) and the Port Chester High School Marching Band — “the pride of our community.”

Port Chester native Anthony Francella, co-owner of Rye Art Gallery & Framing, notes: “Rye has wrapped its arms around Port Chester.” With countless hours and resources dedicated to the village’s Carver Center and Open Door Family Medical Center, “Rye residents are committed to making a difference in Port Chester.”

Rye mayor Josh Cohn adds, “There is a strong appreciation for what Rye does in the Port Chester community — and Rye values the fact that Port Chester is taking a hard look at where they are headed in the future.” With a large-scale commercial project proposed at the former United Hospital site that nearly straddles the Rye border, “there is a desire to ensure that whatever happens is beneficial to both towns.”

— Chappaqua/Mount Kisco —

Mount Kisco

I like Chappaqua, but my wardrobe is more Mount Kisco,” or “Chappaqua used to be a bit snooty,” are two off-the-record comments made by Northern Westchester residents when asked to compare Chappaqua and Mount Kisco. For a change, the most interesting remarks were made by those willing to stand by what they had to say.

“Mount Kisco has a good number of folks who are newly arrived to our country,” says Mayor Gina Picinich. “We also have folks who have been here for five generations. My children go to school with children who don’t look like them, who maybe speak a different language, and that’s a positive.”

Statistically, according to a recent article in the New York Times, close to 45 percent of Mount Kisco’s roughly 11,000 residents are Hispanic. The town’s population is also socio-economically diverse, Picinich adds. Housing options reflect that: A quick perusal of available residences there reveals an incredibly wide range, from multimillion-dollar homes to designated affordable housing.

Prospective buyers researching similar info on Chappaqua real estate demographics will come across such stats as 75.5 percent white, with a median income of $155,232, which is more than twice that of Mount Kisco. Median home value in Chappaqua is estimated at more than $800,000 — some $200,000 higher than its neighbor. So, the numbers bear out the common assumption that Mount Kisco is the more diverse community while Chappaqua the more monied. Yet both boast celebrity residents: Ben Stiller, Vanessa Williams, and, of course, the Clintons have homes in Chappaqua; Robert Kennedy Jr., meanwhile, resides in Mount Kisco, and Gov. Andrew Cuomo and longtime girlfriend Sandra Lee also have a home there.


Population: 1,436
Median Age: 43.6
Race: White: 75.5%, Asian: 12.5%, Hispanic: 7.8%, Black: 1.9%
Median Household Income: $155,232
Persons in Poverty: 2.3%
Persons With a Bachelor’s Degree or Higher: 88.8%

Mount Kisco

Population: 11,103
Median Age: 37.2
Race: White: 53.9%, Hispanic: 35.1%, Asian: 4.7%, Black: 4.6%
Median Household Income: $68,942
Persons in Poverty: 12.1%
Persons With a Bachelor’s Degree or Higher: 37.1%

*Stats from


Chappaqua town supervisor Robert Greenstein points out that relative size is another main difference between Chappaqua and Mount Kisco, as it impacts population density. Mount Kisco is three square miles total, with a big business district, while the town of New Castle, which contains Chappaqua, is 23 square miles, “with many tree-lined country roads, lending it a more rural feel,” he explains.

Practically speaking, “The two towns feel like extensions of one another,” says local Realtor and Chappaqua resident Carmel Riggs. But, of course, most residents made their respective choices for a reason. Gigi Gardon says she moved to Mount Kisco in 1998 because she liked its “ethnic mix and proximity to the train station” and that “people can walk into town on sidewalks.” Mount Kisco is the more bustling, with Northern Westchester Hospital, a movie theater, fun restaurants, cute boutiques, and chain stores. Riggs, on the other hand, says she loves her “quaint, little” Chappaqua, where “everybody knows each other.”

So, while both municipalities might be technically in competition for local dollars, truth is they are both doing battle with a national trend away from small-town retail. Mayor Picinich is the first to mention that many locals were alarmed by empty storefronts in Mount Kisco a couple of years ago. She says she is dedicated to encouraging new business by “streamlining the process” required to set up shop, already signing “a lot of new leases.” For example, plans are in the works to turn Heller’s shoe store into a chocolate factory, and many are interested in repurposing the former JH Crane & Son site. Chappaqua is in the midst of a downtown revitalization and has added Chappaqua Crossing, a major shopping center complete with a Whole Foods, at the old Reader’s Digest site.

Local Sylvia Herzog, who lives just minutes from downtown Mount Kisco, sums up the compare/contrast issue perfectly. “We have straddled the two towns for 24 years,” she says. “Each has always been so warm and welcoming; I would never choose one over the other when I can have the benefits of both.”

— Briarcliff Manor/Ossining —


On the surface, the differences between neighbors Briarcliff Manor and Ossining village seem obvious. Aside from their size (Ossining village’s population is more than three times Briarcliff’s), the residents who make up those villages are decidedly dissimilar.

“I think it’s pretty apparent that the village of Ossining is certainly far more diverse than Briarcliff,” says Miguel Hernandez, former mayor of the village of Ossining. “And there’s also a difference in terms of income: The median income of the two is vastly different.”

The median household income is nearly 2.5 times higher in Briarcliff Manor than Ossining. Home prices are also strikingly varied, with Houlihan Lawrence placing Ossining’s median home cost at roughly $430,000. In Briarcliff, that figure is north of $800K.

Still, choosing a place to live between the two proved difficult for Reva Druskin, who felt that each offered its own set of benefits. Ultimately, she discovered the best of both worlds: choosing a home in Briarcliff that sits within the town of Ossining.

For Druskin, the ability to take advantage of Briarcliff’s recreation — including its outdoor pool — while still being able to send her two children to the Ossining school district were important factors in her decision. “I like the diversity of Ossining schools and the programs they offer,” she says.

Fifty percent of Ossining residents identified themselves as Hispanic or Latino. That compares with just 5.3 percent in Briarcliff Manor.

Ossining’s diversity is reflected in its burgeoning restaurant scene, with eateries ranging from vegan to Portuguese to Jamaican. Diners from both municipalities are keen to take advantage of that food scene. Kathryn Corena, who co-owns Ossining’s popular First Village Coffee, says their shop gets a mix of customers from both Briarcliff Manor and Ossining.

Briarcliff Manor

Population: 7,991
Median Age: 47.4
Race: White: 83.2%, Asian: 6.9%, Hispanic: 5.3%, Black: 3.1%
Median Household Income: $153,573
Persons in Poverty: 2.5%
Persons With a Bachelor’s Degree or Higher: 72.8%


Population: 25,359
Median Age: 37.1
Race: Hispanic: 50%, White: 30.3%, Black: 15.2%, Asian: 3.8%
Median Household Income: $65,458
Persons in Poverty: 11.8%
Persons With a Bachelor’s Degree or Higher: 31.5%

*Stats from

Briarcliff Manor

For Briarcliff residents, though, the eateries in their hometown maintain a special appeal. “It almost feels like family,” resident Sheryl Dennis says of walking into many Briarcliff restaurants. At 105-Ten Bar & Grill at 127 Woodside Avenue, she says owner Anthony Fortunate makes a point of knowing many of his patrons’ names and even their children’s names.

In recent years, the two villages have experienced a divergence in development. Ossining saw Ginsburg Development unveil its 188-unit luxury waterfront apartment complex, Harbor Square, in 2016.

There’s also a strong interest by potential developers in providing new housing in Briarcliff Manor, Village Manager Philip Zegarelli says, but because Briarcliff straddles two towns and two school districts, development can prove challenging.

“You have these overlapping, somewhat competing, different entities, which makes for a very interesting process of addressing various programs, such as development,” he says. “It’s like three-dimensional chess trying to figure everything out here.”

Despite their differences, the two have commonalities. Because both are largely in the same town, with about 90 percent of Briarcliff Manor sitting within the town of Ossining, they share a range of services, including the town tax assessor. They also come together to host an annual 9/11-remembrance ceremony, which includes first responders from both villages.

Zegarelli adds that both villages consistently search for ways to assist each other.

“If there are opportunities to help, we help, and they do the same,” Zegarelli says. “It’s a good relationship.”

— Bronxville/Mount Vernon —


At a mere one square mile in size and with a population of about 6,400 people, Bronxville instantly gives you that unmistakable provincial narrative. There’s more than one quaint bookstore, a small flower shop, and a local hardware store. Around noon, high school and middle school students bustle into Dobbs and Bishop Fine Cheese shop to grab a grilled cheese for lunch. At the end of town and fused together by historical Tudor homes and co-ops is its neighboring city, Mount Vernon. With a population of 68,000, six ZIP codes, three Metro-North stations, and spanning 4.4 square miles, it is difficult to compare the two. Bronxville is known for its pristine, affluent neighborhoods and incredible schools. Mount Vernon, meanwhile, is becoming known for its potential as a new urban center, but with a persistent reputation of corruption and crime.

While both cities seem to be worlds apart despite their adjacency, they do share similar municipal problems. Like most small businesses, the stores in Mount Vernon and Bronxville deal with the challenge of rising rent costs and competing in a new era of online shopping. Bronxville has had to change outdated zoning laws after experiencing a 20 percent decrease in its store capacity. “It’s very hard to sell something in a brick-and-mortar store when you can buy it at midnight on Amazon,” explains Bronxville mayor Mary Marvin. Updated laws now will allow services to be provided in dry-goods businesses, meaning a salon can now provide other services, such as microblading, or a cosmetics store can provide makeup application for its clients. “We have to adapt to how the world is today, because it’s not going backwards,” Marvin adds.


Median Age: 41.7
Race: White: 87.1%, Asian: 5.2%, Hispanic: 4.4%, Black: 1.3%
Median Household Income: $200,000+
Persons in Poverty: 3.4%
Persons with a Bachelor’s Degree or Higher: 80.1%

Mount Vernon

Population: 68,348
Median Age: 40.9
Race: Black: 63.9%, Hispanic: 16.8%, White: 15.7%, Asian: 2.5%
Median Household Income: $52,684
Persons in Poverty: 16.9 %
Persons with a Bachelor’s Degree or Higher: 29.3%

*stats from

Mount Vernon

Some Bronxville residents feel that there has been a socioeconomic divide between the towns that has been brewing for some time. According to 40-year Bronxville resident Florence K., there are nice parts of Mount Vernon but adds, “We were taught when we were young ‘If you didn’t pay for it, you didn’t care for it,’ and we have too many people down in Mount Vernon who are in section 8 places, and they don’t really care…. You really can’t compare Bronxville and Mount Vernon.”

In a city where the median personal income is about $30,000, the expansion of large companies in NYC, like Amazon’s HQ2, might well bring much needed revenue to Mount Vernon and renewed interest among investors. According to Mount Vernon mayor Richard Thomas, one of the things the city will be exploring is a ferry line that links to City Island, LaGuardia Airport, and Long Island City. “People should think of Mount Vernon as a smart, clean, green city of today and into the future,” says Thomas. One of the projects, The Enclave, a collection of midrise buildings, will be targeting Millennials as the city tries to balance an aging demographic.

“We’ve been Mother Theresa for the longest time,” explains Tricia Fraser, a Mount Vernon resident. “We’ve really opened our doors to low-income housing,” but, she adds, “it’s a breath of fresh of air when you have a fair-market-value development coming up that can support the neighborhood.”

“When I look out my window,” says Marvin, sitting in her office in Village Hall, “I’m looking at Mount Vernon. Do we help each other out when we can? Absolutely, and I wouldn’t hesitate to call someone and ask for help.”

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