Long Island, NY is home to some of the most exclusive gated communities in the Hamptons (such as Southampton, East Hampton, or Water Mill) and the North Shore’s Gold Coast (like Sands Point or Old Westbury), offering residents a mix of luxury, privacy, and stunning coastal beauty. Known for its rich history, proximity to NYC, and vibrant culture, the area attracts homeowners who want a lifestyle centered on convenience and sophistication.
In this guide, we rank the Top 20 Most Expensive Gated Communities in Long Island, NY, based on exclusivity, location, and overall prestige. From prestigious Hamptons villages and North Shore enclaves to resort-style retreats on the South Shore or near Manhattan, these communities represent the very best in Long Island living and continue to define the region as a premier destination for luxury real estate.
20. The Hamlet Estates at Jericho
Kicking off our list is The Hamlet Estates at Jericho, a well-regarded gated community known for its luxurious homes and comprehensive amenities. This community offers a blend of spacious single-family homes and townhouses, appealing to a wide range of affluent buyers. The meticulously manicured grounds feature a clubhouse, swimming pool, tennis courts, and a fitness center, fostering a strong sense of community among its residents.
While still highly exclusive, The Hamlet Estates at Jericho is more accessible than some of its North Shore counterparts, with a broader range of property sizes and price points. Its prime location in Jericho, with its excellent school district and proximity to major transportation routes, adds to its desirability. It represents a gateway to the upper echelons of Long Island’s gated community lifestyle, offering a secure and luxurious environment without the extreme price tags of the top-tiered enclaves.
19. Mill Pond at Port Washington
Nestled in the picturesque town of Port Washington, Mill Pond is a serene and upscale gated community that offers a waterfront lifestyle. The community is centered around a beautiful pond and features a mix of elegant townhomes and single-family residences. Residents enjoy access to a private marina, tennis courts, and a clubhouse, creating a resort-like atmosphere.
The exclusivity of Mill Pond lies in its unique waterfront setting and the limited number of homes, which fosters a close-knit and private community. While not as sprawling or opulent as some of the larger estates on this list, its charm, location, and boating amenities make it a highly desirable address for those seeking a tranquil and luxurious lifestyle on the North Shore.
18. The Chatham at North Hills
The Chatham at North Hills is a sophisticated gated community that caters to a discerning clientele seeking luxury and convenience. This community features elegant condominium-style residences with high-end finishes and access to a wealth of amenities. The centerpiece is a grand clubhouse with an indoor pool, fitness center, and social rooms, fostering a vibrant community life.
Known for its meticulous landscaping and maintenance-free living, The Chatham attracts affluent professionals and empty-nesters. Its location provides easy access to the Long Island Expressway and the upscale shopping and dining of the Miracle Mile. While the residences are not sprawling estates, the level of service, security, and quality of life places it firmly among Long Island’s most exclusive communities.
17. The Manors at Old Westbury
The village of Old Westbury is synonymous with old-world wealth and grand estates, and The Manors at Old Westbury is a modern interpretation of this legacy. This gated community features a collection of stately custom-built homes on multi-acre lots, each with its own unique architectural design. The community is known for its rolling hills, mature trees, and a sense of bucolic privacy.
The exclusivity of The Manors is derived from its large lot sizes, the high quality of its homes, and the prestigious Old Westbury address. Residents enjoy a tranquil and secluded environment while being in close proximity to world-class golf courses and equestrian facilities. It represents a more traditional form of luxury living, focused on space, privacy, and architectural grandeur.
16. Gracewood at North Hills
Gracewood is a distinctive gated community built on the former estate of Herbert L. Pratt, a notable figure in the early 20th century. The community features a mix of luxurious single-family homes and townhouses, all centered around the historic Pratt mansion, which now serves as the community’s magnificent clubhouse. Residents enjoy access to an indoor swimming pool, tennis courts, and beautifully landscaped grounds.
The historical significance of the Pratt Estate, combined with the high-end homes and extensive amenities, lends Gracewood a unique and exclusive character. The community’s commitment to preserving its historic charm while offering modern luxuries creates a truly special living experience. It is a place where residents can enjoy a sense of history and community in a secure and opulent setting.
15. The Oaks at East Norwich
A luxurious and relatively newer addition to Long Island’s gated communities, The Oaks at East Norwich offers a collection of high-end single-family homes. Developed by a renowned luxury home builder, this community features homes with exceptional craftsmanship, expansive floor plans, and the latest in modern amenities. The community is designed to provide a high degree of privacy for its residents.
The exclusivity of The Oaks lies in its modern luxury, the quality of its construction, and its prime location in the desirable hamlet of East Norwich. Surrounded by nature preserves and in close proximity to the Gold Coast’s elite country clubs, it offers a sophisticated and contemporary take on luxury living. The substantial homes on generously sized lots attract a discerning clientele seeking both comfort and prestige.
14. Stone Hill at Muttontown
Stone Hill at Muttontown is an exclusive gated community that offers a collection of magnificent estate homes on multi-acre properties. The community is known for its grand residences, many of which feature custom architecture, sprawling lawns, and luxurious amenities such as private pools and tennis courts. The rolling hills and mature woodlands of Muttontown provide a stunning backdrop for these impressive homes.
The sense of seclusion and the sheer scale of the properties are key to Stone Hill’s exclusivity. Residents value the privacy and the tranquil, country-like setting while still being within easy reach of Manhattan. The community appeals to those who desire a grand estate lifestyle within a secure and prestigious gated environment, making it one of the premier addresses on the North Shore.
13. Georgica Estates in East Hampton
Entering the elite territory of the Hamptons, Georgica Estates is a private and exclusive enclave in one of the most prestigious areas of East Hampton. This gated community features a limited number of substantial homes, many with their own private tennis courts and swimming pools. The proximity to the famed Georgica Pond and the Atlantic Ocean adds to its allure.
The exclusivity of Georgica Estates is a function of its prime Hamptons location, the privacy it affords, and the high price of entry. The homes are often architectural showpieces, and the community is a haven for those seeking a discreet and luxurious summer retreat or year-round residence. While not as vast as some of the North Shore communities, its location and the prestige of the “Georgica” name place it high on this list.
12. The Village of Matinecock
While not a single gated community in the traditional sense, the village of Matinecock functions as a highly exclusive and private area with many gated estates. Known for its rolling hills, winding country roads, and large, secluded properties, Matinecock has long been a favored location for the ultra-wealthy seeking privacy and a bucolic setting.
Many of the individual estates within Matinecock are gated and feature extensive private amenities, from equestrian facilities to private golf holes. The low population density and the multi-acre zoning contribute to its exclusive atmosphere. It is a place where privacy is paramount, and the residents, often from prominent families, value the understated and secluded nature of their community.
11. The Village of Mill Neck
Similar to Matinecock, Mill Neck is a village characterized by its grand, gated estates and a profound sense of privacy. This affluent enclave on the North Shore is known for its waterfront properties, sprawling woodlands, and a tranquil, rural atmosphere. The estates here are often hidden from view, accessible only through private drives and imposing gates.
The exclusivity of Mill Neck is deeply ingrained in its history as a haven for the wealthy. The large land parcels, many with water views or access, command staggering prices. Residents enjoy a level of seclusion that is hard to find elsewhere on Long Island, with easy access to private yacht clubs and nature preserves. The combination of natural beauty, privacy, and the sheer scale of the properties makes it one of the most exclusive areas on the Gold Coast.
10. The Village of Sands Point
Sands Point, a peninsula on the North Shore, has a storied history of affluence and is home to numerous gated estates and private communities. The village is known for its stunning waterfront properties with views of the Long Island Sound and the Manhattan skyline. The Sands Point Preserve, a 216-acre park with historic mansions, adds to the area’s majestic character.
The exclusivity of Sands Point is a result of its prime waterfront real estate, its large estates, and its reputation as a haven for a mix of old money and new wealth. Many of the homes are situated within private, gated communities that offer their own beaches and security. The combination of breathtaking views, a rich history, and a commitment to privacy places Sands Point high on the list of Long Island’s most desirable addresses.
9. Old Westbury
The entirety of Old Westbury can be considered an exclusive enclave, with a significant number of its grand estates being individually gated. This historic village has long been a symbol of Gold Coast luxury, with its sprawling mansions, polo fields, and elite country clubs. The minimum two-acre zoning ensures a level of space and privacy that is rare so close to New York City.
The exclusivity of Old Westbury is a blend of its history, its vast estates, and the prominent families who have called it home for generations. The village is home to several gated communities, but even outside of these, the culture of privacy and security is pervasive. The sheer concentration of wealth and the majestic scale of the properties make it a perennial fixture on lists of the nation’s most expensive zip codes.
8. The Village of Brookville
Brookville is another North Shore village that is essentially a collection of magnificent, often-gated estates. Known for its sylvan setting, winding roads, and a commitment to preserving its natural beauty, Brookville offers a level of privacy and tranquility that is highly sought after by the ultra-wealthy. The village’s strict zoning laws ensure that the large-lot, estate-like character is maintained.
The exclusivity of Brookville is defined by its understated elegance and the privacy it affords its residents, which include many high-profile business leaders and financiers. The estates are typically set back from the road, concealed by mature trees and elegant gates. The focus is on a quiet, country lifestyle, with easy access to exclusive golf and country clubs, making it one of the most desirable and expensive places to live on Long Island.
7. The Village of Muttontown
Muttontown, known for its “Horse Country” feel and sprawling estates, is a haven for those who value space, privacy, and an equestrian lifestyle. Many of the properties in this affluent village are individually gated, and there are also exclusive gated communities within its borders. The landscape is characterized by rolling hills, open fields, and miles of riding trails.
The exclusivity of Muttontown is rooted in its unique equestrian culture and the sheer size of its properties. It is a place where residents can enjoy a secluded, country estate lifestyle while still being in close proximity to New York City. The combination of its natural beauty, its passion for horses, and the immense wealth of its residents solidifies its position as one of Long Island’s most exclusive enclaves.
6. The Village of Lattingtown
Lattingtown, situated on the North Shore’s Gold Coast, is a village that epitomizes waterfront luxury and exclusivity. Home to some of the most spectacular and private estates on Long Island, many of which are gated and have their own private beaches on the Long Island Sound. The village is also home to several of the most exclusive private clubs in the country.
The exclusivity of Lattingtown is derived from its prime waterfront location, the grandeur of its historic and modern estates, and its association with some of the most prestigious social and recreational clubs. The privacy afforded by the large, often-gated properties is a major draw for its affluent residents. The combination of stunning natural beauty, unparalleled privacy, and access to an elite social scene makes Lattingtown a truly exclusive enclave.
5. Fordune in Southampton
Entering the rarefied air of the Hamptons’ most exclusive communities, Fordune is a private, gated enclave in Southampton that was once part of the Henry Ford II estate. This prestigious community offers a limited number of magnificent oceanfront and near-oceanfront properties, each with substantial acreage and unparalleled privacy.
The exclusivity of Fordune is legendary, with its private beach access, its historic connection to one of America’s most famous families, and the astronomical price of its real estate. The homes are architectural masterpieces, and the community is a sanctuary for a who’s who of the financial and business worlds. The combination of oceanfront living, extreme privacy, and a storied past makes Fordune one of the most desirable and exclusive communities in the Hamptons.
4. Further Lane in East Hampton
Further Lane is not a formal gated community, but its long, private driveways and the formidable gates of its individual estates create an atmosphere of extreme exclusivity. This legendary lane in East Hampton is home to some of the most spectacular and expensive properties in the Hamptons, with many of them offering direct ocean access and sprawling grounds.
The exclusivity of Further Lane is a result of its prime location, the sheer scale and opulence of its estates, and its roster of high-profile residents, which has included celebrities, artists, and business tycoons. The privacy and seclusion offered by these gated estates are paramount. A Further Lane address is a statement of wealth and status that is recognized around the world.
3. Gin Lane in Southampton
Gin Lane, another iconic Southampton address, is a street of dreams for the ultra-wealthy. While not a formally gated community, the individual estates are almost all gated and offer a level of privacy and luxury that is second to none. This prestigious lane runs along the Atlantic Ocean and is lined with some of the most magnificent and historic homes in the Hamptons.
The exclusivity of Gin Lane is a combination of its prime oceanfront location, the architectural significance of its homes, and its long history as a summer playground for America’s wealthiest families. The properties here are often passed down through generations, and new listings are rare and command breathtaking prices. The prestige of a Gin Lane address is a powerful symbol of old money and enduring social standing.
2. Meadow Lane in Southampton
Often referred to as “Billionaire Lane,” Meadow Lane is a five-mile stretch of prime oceanfront real estate in Southampton that is home to some of the wealthiest and most powerful people in the world. Access to this narrow peninsula is restricted, and the individual estates are all gated, creating a highly secure and private environment. The properties on Meadow Lane offer both ocean and bay frontage, a rarity even in the Hamptons.
The exclusivity of Meadow Lane is absolute. The price of entry is astronomical, and the residents are a veritable who’s who of global finance, media, and industry. The privacy is unparalleled, with many of the estates being completely hidden from public view. A home on Meadow Lane is more than just a luxury residence; it is a statement of immense wealth and influence, placing it at the very pinnacle of exclusive communities.
1. Shinnecock Hills (Private Enclaves)
While Shinnecock Hills is more broadly known for its world-renowned golf club, within this area are some of the most private and exclusive gated enclaves in all of Long Island. These are not large, master-planned communities but rather small, incredibly discreet clusters of magnificent estates, often with their own private security and access to the Peconic Bay or the Atlantic Ocean. The names of these enclaves are often not widely publicized, adding to their mystique.
The ultimate exclusivity of these private enclaves in Shinnecock Hills lies in their extreme privacy, the vastness of the individual estates, and the anonymity they offer to their high-profile residents. These are places where the world’s elite can truly escape, surrounded by natural beauty and protected by layers of security. The combination of stunning landscapes, architectural masterpieces, and an almost impenetrable veil of privacy makes these hidden gems the most exclusive and expensive places to live on Long Island.
Long Island’s exclusive, gated communities highlight the region’s reputation as a hub for luxury living, particularly in the Hamptons and the North Shore’s Gold Coast. Each neighborhood offers its own distinct advantages, whether it be breathtaking ocean views and private beaches, private bay/harbor access (such as along the Great South Bay or Long Island Sound), championship golf (often in the tradition of the region’s top resort courses like those in Southampton or East Hampton), or a strong sense of private, estate-style living. Collectively, they form a landscape where privacy, security, and sophistication are a way of life.
For those considering a move to Long Island, NY, these communities represent not only desirable places to live but also lasting investments in one of the region’s most sought-after markets. Whether nestled among the historic estates near Old Westbury and Roslyn or situated in an exclusive oceanfront community on the South Shore near Quogue, Bridgehampton, or Montauk, these neighborhoods showcase the very best of what Long Island has to offer.