A Guide to Some of the Most Upscale Communities to Live in the New York Area

New York City

Below, we explore the region’s most prestigious enclaves and what makes them so coveted within the world of luxury real estate. 

Greenwich, CT

A gem of Connecticut’s Gold Coast, Greenwich is known as one of the richest cities in the United States, boasting sprawling estates nestled along winding roads. Hedge fund owners and top executives call this idyllic town home, drawn by its exclusive yacht and country clubs, top-ranking schools, and its seamless connection to Manhattan. 

Residents can enjoy premier shopping and fine dining along the charming Greenwich Avenue, while the area’s homes include architectural masterpieces and sprawling properties with manicured grounds. 

Scarsdale, NY

Located a short drive from Manhattan, Scarsdale is a historic suburb famed for its excellent golf and country clubs, such as the Quaker Ridge Golf Club and Scarsdale Golf Club, which cater to its elite residents. Families are especially attracted to Scarsdale for its exceptional school system and serene surroundings. 

The real estate market here is a blend of timeless elegance and modern luxury. Buyers can find stately colonial homes with sprawling lots alongside impeccably designed new-build mansions. 

Southampton, NY

Few places rival Southampton’s reputation as a luxurious summer retreat. Perched along Long Island’s East End, this charming coastal village is embraced by breathtaking beaches and historic allure.

Southampton’s boutique shops and fine dining destinations attract many visitors. Also, its lavish beachfront estates, complete with private access to shimmering shores, command jaw-dropping price points that can regularly exceed tens of millions of dollars. 

East Hampton, NY

East Hampton, another crown jewel of the Hamptons, offers a blend of historic richness and cultural vibrancy. Renowned for its thriving arts scene, this picturesque destination hosts notable galleries and the iconic Guild Hall, a multidisciplinary cultural institution of national significance. 

Residents enjoy access to private beach clubs and golf locales such as Maidstone Golf Club. The real estate options in East Hampton feature immaculate estates with waterfront views and expansive grounds, ensuring exclusivity and luxury at every turn. 

Rye, NY

Nestled along Long Island Sound, Rye exudes charm and elegance. This quaint waterfront community is a sanctuary for families, thanks to its acclaimed public schools and family-friendly attractions like the historical Playland Park amusement area. 

Rye’s upscale lifestyle is enhanced by its marinas, golf courses, and country clubs, creating a sense of leisure and refinement. Its real estate portfolio includes a mix of waterfront estates and luxurious historic properties tucked into quiet residential streets, making it a haven for those seeking a balance of tranquility and splendor. 

New Canaan, CT

For those who appreciate classic New England charm, New Canaan is an ideal locale. This picturesque Gold Coast town features red-brick architecture, stately public parks, and a lively downtown with boutique shops and high-end dining establishments. 

The real estate showcases the town’s storied past, with expansive estates and century-old properties that have been meticulously preserved and updated to fit modern standards of luxury. 

Westport, CT

Westport is another coastal treasure along the Gold Coast, celebrated for its scenic beauty and upper-class charm. The downtown area is notable for its boutique stores, gourmet dining, and a community-centric atmosphere that brings a quintessential New England vibe to life. 

With miles of beaches and convenient access to local marinas, Westport is a paradise for ocean lovers. Its real estate offerings include exquisitely designed waterfront homes and custom-built properties that epitomize sophistication and taste. 

Darien, CT

As the smallest town on the Gold Coast, Darien epitomizes exclusivity. This intimate community is prized for its waterfront views, yacht clubs, and remarkable privacy. Its charming downtown has a distinct, upscale character, and the Country Club of Darien attracts residents with its top-tier golf, racket sports, and fine dining amenities. 

Darien’s real estate market offers stunning homes on generous lots. Many properties here highlight traditional New England architectural aesthetics, marrying timeless designs with luxurious, modern comforts.