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Southold, NY 55+ active adult communities & homes for sale
Living in Southold
Southold is one of four towns in Suffolk County, New York, located in the northeast corner of the state. Its prime location and coastal scenery have made it an enticing option…
Southold is one of four towns in Suffolk County, New York, located in the northeast corner of the state. Its prime location and coastal scenery have made it an enticing option for retirees. The town is also home to a quaint, relaxed environment, which is ideal for those in search of a comfortable lifestyle.
Climate & Geography
Located on the North Fork peninsula of Long Island, Southold lies in a transitional zone between a humid subtropical climate and a humid continental climate. Summers in the region are hot and humid while winters can be cold and snowy, although they are milder than the rest of the state because of the town's coastal location. There is regular precipitation throughout the year, with more rainfall than the national average, an average amount of snowfall, and approximately 206 days of sunshine throughout the year.
Recreation, Culture & Entertainment
Residents in search of outdoor recreation such as hiking, camping, hunting, fishing, canoeing, and more, will find plenty of opportunities in the nature areas around Southold. It's home to plenty of wildlife and coastal habitats including: Fisher Island Beaches, Pine Islands and Shallows, and Golfsmith Inlet and Beach. Aside from these, there are also six large vineyards across the town, which offer fine tasting wine and fascinating scenery.
Southold is known for its small-town charm and neighborly feel. Their downtown is defined by local shops and businesses, such as antique stores, art galleries, restaurants, and breweries. Not to mention, its location on Long Island is convenient for residents who want to explore even more amenities, beaches, and attractions. Residents can also reach New York City in two hours by car or three hours on public transit, perfect for a day trip or a weekend getaway.
Cost of Living & Taxes
Much like the majority of New York, the overall cost of living in Southold is significantly higher than national average. This can be attributed to the cost of housing which is well above the U.S median.
Health Care
Southold is in driving distance of Port Jefferson where residents can find two hospitals and medical centers. One of these facilities, John T. Mather Memorial Hospital, is rated high performing by U.S News in 3 adult specialties and 2 other procedures.
Frequently Asked Questions
In Southold, there is 1 small community with less than 500 homes.
The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.
No, there are no gated 55+ communities in Southold.
On average, listings in 55+ community in Southold stay on the market for around 462 days. The average price of homes for sale in this community is approximately $525,806, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $525,806.
95 communities near Southold
207 homes near Southold
Relevance
2 beds
|2 baths
|1,078 sq ft
|Condo
2 beds
|2 baths
|1,130 sq ft
|Condo
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
2 beds
|2 baths
|1,398 sq ft
|Condo
2 beds
|3 baths
|1,700 sq ft
|Condo
4 beds
|4 baths
|2,597 sq ft
|Condo
2 beds
|3 baths
|2,471 sq ft
|Condo
1 beds
|2 baths
|1,375 sq ft
|Condo
2 beds
|2 baths
|1,695 sq ft
|Condo
2 beds
|3 baths
|1,874 sq ft
|Condo
2 beds
|3 baths
|1,998 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
3 beds
|3 baths
|2,620 sq ft
|House
2 beds
|2 baths
|1,733 sq ft
|Condo
2 beds
|2 baths
|1,200 sq ft
|Condo
1 beds
|3 baths
|1,426 sq ft
|Condo
2 beds
|1 baths
|1,085 sq ft
|Condo
2 beds
|1 baths
|1,020 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
2 beds
|2 baths
|1,867 sq ft
|Condo
2 beds
|3 baths
|2,516 sq ft
|Condo
3 beds
|2 baths
|1,500 sq ft
|Condo
1 beds
|1 baths
|1,017 sq ft
|Condo
3 beds
|3 baths
|1,922 sq ft
|Condo
2 beds
|2 baths
|1,308 sq ft
|Condo
2 beds
|3 baths
|1,426 sq ft
|Condo
2 beds
|3 baths
|1,860 sq ft
|Condo
2 beds
|2 baths
|1,555 sq ft
2 beds
|2 baths
|1,666 sq ft
|Condo
2 beds
|2 baths
|1,112 sq ft
|Condo
2 beds
|2 baths
|1,292 sq ft
|Condo
3 beds
|3 baths
|2,008 sq ft
|Condo
2 beds
|2 baths
|1,432 sq ft
|Condo
2 beds
|2 baths
|1,432 sq ft
|Condo
2 beds
|2 baths
|1,434 sq ft
|Condo
2 beds
|2 baths
|1,557 sq ft
|Condo
2 beds
|2 baths
|1,398 sq ft
|Condo
Frequently Asked Questions
In Southold, there is 1 small community with less than 500 homes.
The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.
No, there are no gated 55+ communities in Southold.
On average, listings in 55+ community in Southold stay on the market for around 462 days. The average price of homes for sale in this community is approximately $525,806, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $525,806.
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REIN updates its listings on a daily basis. Data last updated: Sep 20, 2026.
This application does not include information on all of the properties available for sale at this time.
