7 Most Expensive Cities in Westchester County: Luxurious Living in New York

Westchester Most Expensive Cities

Westchester County, New York, is renowned for its opulent homes, scenic landscapes, and proximity to Manhattan. These attributes, coupled with its historical significance, make it a sought-after destination for discerning buyers. Several cities within the county stand out for their premium real estate values, drawing attention from investors, industry enthusiasts, and homebuyers moving to Westchester County. To learn about the most expensive cities in Westchester County, it's time to shed light on their unique characteristics and the factors driving their high real estate prices.


Located in the northern half of Westchester County, the town of Bedford is known for its historic district, rural atmosphere, and convenient schools. 

The median household income is over $300,000, with monthly expenses averaging $4,000 per adult. The town consists of three hamlets: Bedford Hills, Katonah, and Bedford Village. The Metro-North Railroad's Harlem Line connects to Bedford Hills and the hamlet of Katonah, enabling residents to commute into New York City in about one hour and 20 minutes.

Bedford offers many upscale amenities, from its namesake Golf & Tennis Club to the Bedford Post Inn. Founded in 1860, the Bedford Post Inn offers a luxury hotel, two fine-dining restaurants, and a yoga studio. Shoppers and history buffs alike will enjoy the Bedford Village Historic District, home to several boutiques and a museum housed in an 18th-century courthouse. 

The district also boasts a variety of restaurants and entertainment venues, from the artisanal American eatery Bedford 234 to the Bedford Playhouse movie theater.

Single-family homes in Bedford range from 1,500-square-foot Colonials to 10,000-square-foot estates. These sit on expansive lots that offer plenty of outdoor space and privacy. Home prices range from $1 million to upwards of $10 million.

Bedford Amenities

  • The Bedford Store
  • Bedford Hills Museum
  • Fox Lane Middle School
  • John Jay Homestead
  • GlenArbor Golf Club
  • Mianus River Gorge Preserve


Reasons to Live in Rye, NY

Located in Southern Westchester County, Scarsdale is known for its luxury real estate market and convenient commuter rail service to New York City. It ranks as one of the wealthiest New York City suburbs, with a median household income of around $500,000. 

In contrast, the county-wide average stands at approximately $110,000. When considering the cost of living in Scarsdale, a four-person household typically spends $14,000 per month on housing, utilities, food, and other daily expenses.

Apart from its stately homes and popular schools, Scarsdale also offers residents several top-tier amenities, including Fenway Golf Club, Quaker Ridge Golf Club, and an Equinox gym. 

Other local attractions include an abundance of parks and trails, plus a variety of restaurants, cafes, and shops in the city's charming downtown area. The Italian eatery Tutta Bella and the seasonal American restaurant Meritage are two of Scarsdale's most popular fine-dining spots.

Many homes in Scarsdale are part of the Tudor Revival and Young Colonial architectural styles that typify the area. Other popular home styles include new construction, traditional Craftsman styles, and Cape Cods. Homes for sale in Scarsdale range from $700,000 for a 1,200-square-foot property to $3 million for a 6,000-square-foot home. Scarsdale luxury homes list from $3–$8 million.

Scarsdale Amenities

  • Saxon Woods Park
  • DeCicco Family Market
  • Vernon Hills Shopping Center
  • Fox Meadow Elementary School
  • Boulder Brook Equestrian Center


Harrison lies in the southern part of Westchester County, close to the county's South Shore beaches. With a median household income of roughly $250,000 and a four-person household typically spending around $13,500 per month on necessities, it's one of Westchester'smost expensive cities.

Residents enjoy convenient access to the Metro North train station on the Hudson Line and I-95, making it an ideal option for residents commuting to their jobs in Westchester County or NYC. The city offers several public schools, including Louis M. Klein Middle School and Harrison High School. 

Upscale amenities include Harrison Meadows Golf Course. The club features an outdoor pool, seven fitness studios, and several athletic courts. For shopping, dining, and entertainment, residents head to downtown Harrison, where they can watch a show at the New York Performing Arts Center, dine at Trattoria Vivolo, and shop at locally owned stores.

Homes in Harrison are mostly single-family detached structures, with a selection of townhouses and condos. Popular architectural styles include Colonial, French Country, and Craftsman. Single-family detached homes typically start at around $600,000, while Harrison's luxury homes can list for more than $4 million.

Harrison Amenities

  • Brentwood Field
  • Riis Park
  • DeCicco & Sons
  • The Harrison Market
  • St. Vincent's Hospital
  • Laughing Horse Coffee


Reasons to Live in Rye, NY

Located on the picturesque Long Island Sound, the city of Rye offers a classic suburban lifestyle with upscale homes and plenty of outdoor recreation. The median household income hovers around $380,000, over three times the county-wide average. The cost of living in Rye is also high, with a four-person household typically spending around $16,000 per month on essential needs.

Many residents commute to New York City via the Metro-North Railroad's New Haven line, which has stops in Rye and nearby Harrison. Locally, Purchase Street in downtown Rye—one of Westchester's most walkable cities—is the city's main retail hub. This walkable district boasts several locally-owned boutiques and restaurants, like Misfit Bazaar and Frankie & Johnnie's Steakhouse.

Outdoor recreation is also abundant, with Rye Town Park & Beach located on Long Island Sound. Another option is Marshlands Conservancy, which offers 147 acres of trails and natural areas to explore. The city is also home to the beachside Westchester Country Club location and Rye Country Day School, a private college prep institution.

Real estate in Rye ranges from 600-square-foot condos to 10,000-square-foot estates. Waterfront homes list for a median price of almost $3 million, and while luxury homes in Rye can list for more than $10 million, most homes can be found from $1–$4 million. Colonial, Tudor, and Contemporary Ranch are among the popular home styles, with brick and wood exteriors that exude an old-world charm. Home prices range from $1 million to upwards of $7 million.

Rye Amenities

  • Rye Nature Center
  • Playland Park
  • Rye YMCA
  • Apawamis Country Club
  • Milton Elementary School
  • Rye Country Store

Pound Ridge

Luxury buyers looking for seclusion and natural beauty will find Pound Ridge to be an attractive option. Located on the eastern side of Northern Westchester County and surrounded by rolling hills, it offers some of the most scenic real estate in New York. 

The median household income stands at around $350,000 per year, helping residents handle the cost of living in Westchester County—approximately 55% above the national average. They enjoy a high quality of life, with commuter options to New York City and plenty of outdoor activities.

Pound Ridge Golf Club is one of the area's main attractions, featuring 18 holes that comprise one of the best public golf courses near New York City. Additional outdoor recreation is available at the 4,300-acre Ward Pound Ridge Reservation and Pound Ridge Town Park, where residents can access a pool, playground, and athletic courts.

The Inn at Pound Ridge is another popular destination, with a fine dining menu curated by renowned chef Jean-Georges Vongerichten. Schools in the area include Pound Ridge Elementary and Rippowam Cisqua School, which offers private education.

Pound Ridge boasts a visually appealing real estate landscape characterized by stately single-family residences, and multi-family buildings and condominium communities are noticeably absent. Popular architectural styles include French Country, Colonial, and Contemporary. Homes for sale in Pound Ridge typically range from $1 million to $7 million.

Pound Ridge Amenities

  • Blue Heron Lake
  • The Huntress Boutique
  • Pound Ridge Tennis Club
  • North Star Restaurant
  • Blind Charlie's Cafe
  • The Market at Pound Ridge Square


Reasons to Live in Rye, NY

Bronxville is an upscale village in Westchester County, known for its Tudor Revival architecture and winding tree-lined streets. The median household income stands at around $200,000, with a four-person household spending approximately $15,000 on monthly expenses. Just north of the Bronx, the Bronxville station on Metro-North's Harlem Line offers easy access to Grand Central Station in about 40 minutes.

The village is home to Sarah Lawrence College, which provides a vibrant academic atmosphere. Local amenities include the Siwanoy Country Club, Pure Barre Fitness, and a seasonal farmers market. Residents head to the city's downtown district for shopping, dining, and entertainment. Here, they can explore upscale boutiques like The Silk Road and Whim, plus local staples like the Bronxville Diner and Park Place Bagels. Private educational facilities include the Chapel School, St. Joseph's School, and Bronxville Montessori.

Real estate in Bronxville consists mostly of single-family homes, with a handful of condos near the Metro-North station in the city center. Popular architectural styles include Arts & Crafts, Colonial, and Tudor Revival. Home prices in the detached market typically start just under $1 million, but the community's share of Westchester County luxury homes can list for more than $4 million.

Bronxville Amenities

  • Bronx River Pathway
  • Scalini Osteria
  • Slave to the Grind Cafe
  • Underhills Crossing Restaurant
  • Bronxville Field Club
  • New York-Presbyterian Hospital


Armonk, located near the Connecticut border, is a charming hamlet nestled within the town of North Castle. The average household earns approximately $300,000 per year, with monthly expenses totaling around $4,000 per adult. 

The city is home to IBM's global headquarters, which overlooks Kensico Lake, plus a variety of shops, restaurants, and entertainment venues. Residents commuting to NYC typically drive 15 minutes south to the North White Plains station on Metro-North's Harlem Line, then take the train from there.

Residents of Armonk enjoy a vibrant commercial and entertainment district along Main Street. This flower-basket-lined corridor is home to places like Armonk Country Kitchen, the Bagel Emporium, and Tazza Cafe. Another popular spot is Hickory & Tweed, selling bike and ski gear since 1961. Green spaces include John Lombardi Park and Wampus Brook Park, where visitors can enjoy nature trails and water activities in the summer. 

In terms of upscale amenities, Armonk offers two prestigious country clubs complete with golf courses, pools, and restaurants: the Summit Club and Whippoorwill Club.

Armonk real estate offers a diverse range of homes, catering to various preferences and budgets. Cozy one-bedroom Westchester condos are priced around $500,000, while detached homes in Armonk list from the $600s to more than $5 million. Popular architectural styles include Colonial, Contemporary, French Country, and Ranch, with many homes dating from the 1990s.

Armonk Amenities

  • Wine Geeks
  • La Mer Seafood
  • Beascakes Bakery
  • Equinox Armonk
  • North Castle Library
  • Armonk Indoor Sports Center

Luxury Abounds in Westchester County

Westchester County's most expensive cities are not just about price tags; they epitomize luxury, convenience, and prestige that few regions can match. All generally considered among Westchester County's best cities, each of these communities boasts its distinct charm, from waterfront views to architectural masterpieces. As the demand for prime locations continues to rise, Westchester stands as a testament to the ever-evolving definition of upscale living. For anyone intrigued by elite real estate, understanding Westchester's priciest cities offers valuable insights into what makes a location truly exceptional. 

Ready to call Westchester County home? Contact the Bizzarro Agency at (917) 979-2259 to get in touch with an NYC real estate agent and discover your Westchester County dream home today.

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