6 Most Popular Gated Communities in Westchester County: Private Luxury in NY

Westchester County Gated Communities

Westchester County, New York, renowned for its serene landscapes and upscale living, is home to many popular gated communities. These communities offer enhanced security and a host of luxurious amenities, all of which contribute to the highly sought-after real estate within their gates. For homebuyers moving to Westchester County, the unique features of the region's gated communities, from meticulously landscaped grounds to state-of-the-art facilities, can help guide the homebuying process. Discover the elegance and tranquility that these gated communities in Westchester County offer.

Greystone on Hudson (Tarrytown)

Greystone on Hudson is a community of 23 luxurious estates designed in the style of Gilded Age architecture. The community is located 13 miles north of Manhattan in the village of Tarrytown on 100 acres of picturesque countryside, offering stunning views of the Hudson River. Each grand mansion has over 8,000 square feet of living space and at least six bedrooms and eight bathrooms. The largest estate offers double the size of the others, with roughly 30 acres of impeccably maintained lawns and gardens. Modern amenities include custom-designed gourmet kitchens, home gyms, spa-inspired bathrooms, and outdoor pools. 

Greystone on Hudson's location offers easy access to schools, golf courses, equestrian centers, and more, making real estate there some of the most sought-after luxury homes in Westchester County. The Irvington Public School District and private options like Horace Mann, Rye Country Day, and Hackley School are nearby. Sleepy Hollow Country Club and Ardsley Country Club offer world-class amenities, while Blue Hill at Stone Barns provides a high-end, farm-to-table dining experience. Irvington's historic district offers additional entertainment, with an array of restaurants, cafes, and shops, plus a performing arts theater and a farmers market.

Home prices at Greystone on Hudson range from $6 million to $20 million, depending on property size, style, and acreage. HOA fees are around $1,300 monthly, including 24/7 security, doorman, and concierge services.

Greystone on Hudson Amenities

  • Westchester Mall
  • Black Cat Cafe
  • Red Hat on the River
  • The Masters School
  • Irvington High School
  • Irvington Boat Club

The Greens at Cherry Lawn (New Rochelle)

Living in New Rochelle's Greens at Cherry Lawn Neighbourhood

The Greens at Cherry Lawn is a neighborhood of luxurious gated community homes in New RochelleEach home boasts a minimum size of 3,500 square feet and sits on approximately half an acre. These homes feature bright, airy spaces with high ceilings, living and dining rooms with fireplaces, gourmet kitchens, and high-end finishes. The private community is on a 17-acre hillscape with mature trees, fountain gardens, and manicured lawns.

Located in Southern Westchester County, the Greens at Cherry Lawn is a highly desirable community for those seeking luxury living in a serene and private environment conveniently close to New York City. Commuters enjoy a 45-minute train ride to Grand Central Station via Metro-North, while drivers can take I-95 or the Hutchinson Parkway. The community is surrounded by local amenities such as Quaker Ridge Golf Club, Ward Elementary School, and Ward Acres Park, all within a five-minute drive. Another favorite spot is Cherry Lawn Farm, serving fresh produce and deli items since 1936.

Prices for the New Rochelle luxury homes at The Greens at Cherry Lawn vary depending on the size and features of each property but typically range from $1.5 million to $2.5 million. The common charges are roughly $1,344, covering the clubhouse, pool, and tennis court maintenance and access.

The Greens at Cherry Lawn Amenities

  • Pinebrook Park
  • Pinebrook Tennis Center
  • Winged Foot Golf Club
  • Golden Horseshoe Mall
  • Da Giorgio Restaurant
  • New Rochelle High School

Park Lane Preserve (West Harrison)

Park Lane Preserve is a picturesque lakeside community in the city of West Harrison primarily completed in 2000. It's located on a hill, and views of Rye Lake add to the allure of the community’s waterfront homes in Westchester. Spread across 400 acres of lush vegetation, this 306-lot subdivision features luxurious single-family homes ranging in size from 3,000 to over 5,000 square feet. Many of these properties sit on half-acre to 1.5-acre lots, providing ample green space and privacy amid the tall and dense trees. Residents enjoy a suite of amenities, including an in-ground pool, playground, clubhouse, spa, and fitness facilities. 

Residents of Park Lane Preserve enjoy the peace and seclusion of the area while still being just a short drive away from shopping, dining, and entertainment. Popular attractions in the area include Kensico Dam Plaza and Cranberry Lake Preserve, plus various shops, restaurants, and services along North Broadway. The community is located in the highly-rated Harrison School District, with several schools, such as Purchase Elementary, Klein Middle School, and Harrison High School. Commuters to New York City can easily access the North White Plains or Valhalla train stations along the Metro-North. Additional routes are available via the Bronx River Parkway, I-287, and I-684. 

Park Lane Preserve homes for sale typically range from the mid-$700s to just over $2 million. The HOA fees are approximately $500 and are paid twice a year.

Park Lane Preserve Amenities

  • Townhouse Diner
  • Abatino's Pizza & Pasta
  • Valhalla Animal Hospital
  • Westchester County Airport
  • Charles Dawson History Center
  • Performing Arts Center (at Purchase)

Kensington Woods (New Rochelle)

Completed in 2005, Kensington Woods is a neighborhood of 52 luxury stone and stucco gated community homes in New Rochelle conveniently located off the Hutchinson Parkway. Its architectural landscape is quintessentially Westchester, with winding roads, lush greenery, and elegant designs that blend seamlessly with the natural surroundings. Homeowners enjoy a peaceful and aesthetically pleasing environment on 17 acres while being just 20 miles away from New York City. The homes prioritize low-maintenance living, with first-floor suites and elevators that provide easy access to all floors. An active homeowner's association handles snow removal and lot maintenance, among other services.

Kensington Woods’ share of the luxury homes in New Rochelle offers several flex-use spaces that can be customized per the buyer's interests, leaving room for creativity and personalization. These spaces can be used as home offices, yoga studios, wine cellars, and more. Neighborhood amenities include schools, parks, golf courses, and shopping centers, providing residents with diverse options for leisure activities. Ward Acres Park, Wykagyl Country Club—one of Westchester’s best golf courses—Quaker Ridge Shopping Center are among the most visited local attractions. Vernon Hills shopping district is also nearby, with popular amenities like Trader Joe's, Equinox gym, and Tutta Bella restaurant.

Homes in Kensington Woods range in size from 3,000 to 4,500 square feet. Prices generally fall between $1 million and $1.6 million.

Kensington Woods Amenities

  • Iona Prep School
  • Ward Elementary
  • Twin Lakes Park
  • North End Tavern
  • Cherry Lawn Farm
  • Lake Isle Country Club

Cobblefield (White Plains)

Living in White Plains' Cobblefield Neighbourhood

Cobblefield is a community of gated homes in White Plains, west of Hutchinson Parkway and east of Rosedale Avenue. Completed in 1993, it features 94 luxurious homes spread over 54 acres of lush greenery. Homes showcase classic Westchester stone architecture with stunning facades that combine stonework and stained cedar siding for a sophisticated look. The properties range in size from 2,600 to 3,700 square feet and are all equipped with fireplaces, nine-foot ceilings, and two-car garages. The homeowner's association provides a 24-hour manned security gate and access to two all-weather tennis courts, an outdoor heated pool, and a hot tub. 

Cobblefield is a five-minute drive to popular local amenities such as Lombardo's Pizza & Pasta and Maple Moor Golf Course. Nature enthusiasts can go hiking and swimming at Saxon Woods Park, while shoppers can find everything they need in Downtown White Plains, just ten minutes away by car. Additionally, the White Plains Metro-North Station is only two miles away, providing frequent trains to Grand Central Station and Midtown Manhattan East in just over 30 minutes.

Pricing in Cobblefield varies based on six distinctive floor plans, with home values ranging from $900,000 to $2 million. The average HOA fee ranges from $700–$900.

Cobblefield Amenities

  • Saxon Woods Trail
  • The Leffell School
  • Clover Hill Daycare
  • Life Time Fitness Center
  • Montessori Garden School
  • Westchester Hills Golf Club

St. Regis Residences (Rye)

St. Regis Residences in Rye is the first residential community by the five-star hotel chain without an attached hotel. It opened in July 2021 and boasts 92 contemporary condos in Rye, all of which boast high-end features, including hardwood and stone flooring, quartz and marble countertops, Wolf/Sub-Zero appliances, and French doors that open to spacious balconies and terraces. The St. Regis brand epitomizes the best in ultra-luxury living, with on-site amenities that include a 15-seat movie theater, a golf simulator, a curated art gallery, and a state-of-the-art fitness center with an indoor pool and spa. The outdoor amenities showcase a central indoor/outdoor pavilion, a wellness court, gardens with seating and water features, and a fenced dog run. 

Homeowners of St. Regis Residences are conveniently located near Rye's most popular attractions, including the Rye Roadhouse Cajun-Creole restaurant, the Rye Nature Center, and the historic Downtown Rye. The residences are situated on Old Post Road between I-95 and US 1, making it a convenient spot for commuters. Other nearby amenities include Apawamis Country Club, Rye Arts Center, Rye Beach, and Playland Park.

St. Regis Residences homes—which can be found among the highest-priced luxury homes in Rye—offer 1,600–3,000 square feet and are typically priced between $1.8 million and $5 million. Association fees range from $2,000 to $6,000.

St. Regis Residences Amenities

  • Rye Racquet Club
  • Rye Grill and Bar
  • Ruby's Oyster Bar
  • Rye Country Store
  • Village Social Kitchen
  • Rye Country Day School

Behind the Gates in Westchester County

Westchester County's gated communities epitomize luxury and privacy, set against the backdrop of the county's natural beauty. Each community is located in one of Westchester County’s popular towns and offers its residents a unique blend of comfort and high-end amenities. For those seeking a quality living environment, Westchester County’s gated communities present an array of options that cater to discerning tastes and preferences.

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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