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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
Of the 1 55+ community in Southold, it is for sale. By size, 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 533 days. The average price of homes for sale in this community is approximately $530,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $530,500.
95 communities near Southold
223 homes near Southold
Relevance
2 beds
|2 baths
|1,078 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
|1,044 sq ft
|Condo
2 beds
|2 baths
|1,767 sq ft
|Condo
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
2 beds
|3 baths
|2,258 sq ft
|Condo
2 beds
|1 baths
|1,050 sq ft
|Condo
2 beds
|2 baths
|1,587 sq ft
|Condo
2 beds
|1 baths
|1,116 sq ft
|Condo
2 beds
|2 baths
|1,112 sq ft
|House
3 beds
|2 baths
|1,792 sq ft
|Manufactured Home
2 beds
|1 baths
|890 sq ft
|Condo
2 beds
|2 baths
|1,134 sq ft
|House
3 beds
|3 baths
|2,620 sq ft
|Condo
3 beds
|3 baths
|2,531 sq ft
|Condo
2 beds
|2 baths
|1,476 sq ft
|Condo
2 beds
|2 baths
|1,070 sq ft
|Condo
2 beds
|3 baths
|1,920 sq ft
|Condo
2 beds
|1 baths
|938 sq ft
|Condo
2 beds
|2 baths
|1,096 sq ft
|Condo
2 beds
|2 baths
|1,321 sq ft
|Condo
2 beds
|3 baths
|1,370 sq ft
|Condo
2 beds
|2 baths
|1,027 sq ft
|Condo
3 beds
|2 baths
|1,368 sq ft
|House
2 beds
|3 baths
|1,700 sq ft
|Condo
2 beds
|3 baths
|1,378 sq ft
|Condo
3 beds
|3 baths
|2,412 sq ft
|Condo
2 beds
|2 baths
|1,420 sq ft
|Condo
2 beds
|2 baths
|1,285 sq ft
|Condo
2 beds
|2 baths
|1,306 sq ft
|Condo
3 beds
|2 baths
|1,716 sq ft
|Condo
2 beds
|2 baths
|1,432 sq ft
|Condo
2 beds
|2 baths
|1,447 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
2 beds
|2 baths
|1,328 sq ft
|Condo
2 beds
|2 baths
|1,390 sq ft
|Condo
Frequently Asked Questions
Of the 1 55+ community in Southold, it is for sale. By size, 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 533 days. The average price of homes for sale in this community is approximately $530,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $530,500.
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REIN updates its listings on a daily basis. Data last updated: Oct 20, 2026.
This application does not include information on all of the properties available for sale at this time.
