From its lighthouses to its sandy beaches, Long Island has always had a reputation for exclusivity, beautiful scenery, and high-end homes and shops. It was settled by English and Dutch explorers in the nineteenth century, and soon attracted wealthy Europeans and Americans, who built estates here. These have been repurposed into subdivisions, museums, parks, golf courses, and active adult neighborhoods.
Long Island's northern shores meet Long Island Sound, which separates it from Connecticut and Rhode Island. To the south, you'll find Jamaica Bay, Great South Bay, South Oyster Bay, and barrier islands that separate the strip of land from the Atlantic Ocean. Long Island has four counties: Brooklyn, Queens, Nassau, and Suffolk, but the latter two are what most people consider to be Long Island. They are among the most expensive areas to live in the country.
Despite this, 55+ homebuyers can find gated East Long Island communities with homes for sale in all price ranges. Talk about checking all the boxes; a home in prestigious Suffolk County, the security of a gated entrance, and the right price for your lifestyle. We’ve picked seven to highlight here.
Below $100k - Mid $100s
Greenwood Village is an affordable, established 55+ community with 512 resale attached and single-family homes about five miles from Long Island’s southern shores. Most of its homes are cozy single-families, sized from 900 to 1,300 square feet with one to three bedrooms, one to two bathrooms, and attached one-car garages. Some also have basements and Florida rooms.
The attached models are around 1,100 square feet with two bedrooms, one bathroom, and attached one-car garages. This is a land-lease community, meaning that residents own their homes but pay monthly fees for their land.
Residents enjoy a full complement of amenities, like a community bus, walking trails, scenic ponds, tennis, bocce, and an outdoor pool. Greenwood’s clubhouse offers an exercise room, a game room, a great room, and a woodworking shop. There's also a vibrant Seniors Club that sponsors organized events.
Learn more information about Greenwood Village here.
Low $200s - High $200s
Our second gated active adult neighborhood is to the north near two golf courses. Country Village Estates offers 195 attached resale homes with five floor plans. They range from 1,200 to 1,400 square feet with one or two bedrooms, two bathrooms, and attached one-car garages. Some also feature patios, formal dining rooms, and basements.
Homeowners here also have the use of a community bus as well as bocce ball courts, walking trails, and an outdoor pool and patio. The clubhouse has a ballroom, a lounge, and an exercise room.
Country Villages Estates is minutes from the intersection of Routes 25 and 83, where you can find grocery shops, pet stores, clothing stores, and medical offices. There are also many nearby options for medical care, including Stony Brook University Hospital and Long Island Community Hospital.
Learn more information about Country Village Estates here.
High $200s - High $300s
Talk about location: Fairfield at St. James is practically within walking distance of a Trader Joe’s, a movie theater, Whole Foods, restaurants, and the Smith Haven Mall. It’s also just minutes from northern shore beaches, waterways, and parks like Nissequogue River State Park.
This large, established community offers 653 resale attached and condo homes, with the majority being condos. These feature one or two bedrooms and bathrooms, patios or balconies, and one-car garages or driveways. The select number of attached homes offer three bedrooms, two-and-a-half bathrooms, and garages or driveways.
The busy homeowners here enjoy spending time at fundraiser luncheons, holiday parties, and the Twin Ponds Senior Club. Community amenities include two outdoor pools, an indoor pool, a community bus, and a clubhouse with a fitness center and meeting rooms.
Learn more information about Fairfield at St. James here.
Low $300s - High $400s
It’s a golfer’s dream: Sunken Pond Estates is close to four courses, including The Woods at Cherry Creek and Sandy Pond. This active adult neighborhood was completed in 2005, and it has 194 resale attached homes offered in three floor plans. These range from 1,344 to 1,656 square feet with two bedrooms, two or two-and-a-half baths, and one-car garages. Some have options like new kitchen appliances and sunny alcoves.
The modern clubhouse has an exercise room with an aerobics studio, a lounge area and bar, a catering kitchen, and a media room. Outside, there's a refreshing pool, plus a putting green, shuffleboard, and bocce ball courts. Drive a mile south of this lovely property, and you'll find the Peconic Bay Medical Center, and a shopping center with restaurants, a Target, Staples, TJ Maxx, and a pharmacy.
Learn more information about Sunken Pond Estates here.
Mid $300s - High $400s
Also in Riverhead and similar in size to Sunken Pond Estates, Saddle Lakes was completed in 2002 with 196 resale attached homes. It's quite close to Indian Island County Park, which has camping, fishing, hiking, and a playground for the grandchildren.
The four floor plans in this community are sized from 1,247 to 1,837 square feet with two to three bedrooms, two to three bathrooms, and attached one-car garages. Some also have full basements, porcelain floors, stone patios, and central vacuum systems.
Indoor and outdoor amenities include swimming pools, a spa, a movie theater, and an exercise room at the clubhouse. Friends and neighbors gather here for card games and movie nights, and since Saddle Lakes is just 30 minutes from the Long Island MacArthur Airport, travel is quite convenient.
Learn more information about Saddle Lakes here.
High $400s - Mid $500s
Less than two miles from the charming waterfront town of Port Jefferson, Setauket Meadows is so close to Long Island’s north shores that you’ll feel like you’re on a year-round vacation. It was completed in 2007 with 150 resale attached homes which come in three floor plans. They range from 1,773 to 1,878 square feet with two bedrooms, two-and-a-half bathrooms, and attached one-car garages. Designer touches like nine-foot ceilings and granite countertops make these exclusive homes comfortable and contemporary.
The amenities here are designed for active lifestyles, offering residents a beautiful clubhouse with its own indoor pool and spa. There's also a meeting room with a fireplace, a business center, game and activity rooms, and a sauna. Outdoor perks include a second pool, a putting green, tennis and bocce courts, and walking and biking trails.
Learn more information about Setauket Meadows here.
Low $500s - Low $700s
Moving southeast towards the Hamptons, we find Encore Atlantic Shores, an upscale 55+ community with 240 resale attached homes in an idyllic location close to the island’s easternmost points. Encore is close to where the island splits into its north and south forks, placing it near the Great Peconic Bay and Hubbard County Park.
The six well-designed floor plans range from 1,424 to 2,709 square feet with two or three bedrooms, two or two-and-a-half bathrooms, and attached garages. Upgrades may include expansive master suites, lofts, gourmet kitchens, and large dining rooms.
The property has its own putting green, tennis courts, outdoor pool and patio, and bocce and tennis courts. The elegant clubhouse has an indoor pool with a spa, saunas, and steam rooms; a fitness center with lockers; a ballroom; and several activity rooms. Well-attended events like movie nights, Sunday brunches, Tai Chi class, and holiday parties keep everyone happy and connected.
Learn more information about Encore Atlantic Shores here.