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The highest-performing listings in Stonington.
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Generally Investor friendly
STRs are explicitly allowed with no municipal permits, fees, or caps required, creating an open operating environment. However, the lack of formal regulations creates uncertainty for investors, and the 15% state room occupancy tax applies. The defeated 2023 ordinance proposal indicates potential future restrictions, making this more challenging than a completely unregulated environment.
Local STR Agent
STR specialist · Stonington, CT
Stonington is a coastal town in New London County, Connecticut, home to approximately 18,500 residents. Tucked into the far southeastern corner of the state along Fishers Island Sound and the Rhode Island border, it carries the character of a classic New England seafaring community, with a historic village core, working harbors, and a strong maritime identity. The town is best known for its colonial-era Borough, its proximity to the popular destinations of Mystic and Watch Hill, and its appeal as a quieter alternative to busier coastal getaways. Stonington sits roughly 130 miles northeast of New York City, a drive of about two and a half hours, and about 100 miles southwest of Boston, placing it within easy weekend reach of two major metropolitan areas.
The heart of the community is the Stonington Borough, a small peninsula jutting into the Sound that is lined with preserved 18th- and 19th-century homes, narrow streets, and a working waterfront. Visitors come for the walkable village atmosphere, locally owned shops, seafood restaurants, and views of fishing boats and pleasure craft. The Borough is also home to the Old Stonington Lighthouse, one of the oldest lighthouses on Long Island Sound, and sits just a few minutes from the rest of town.
Just to the north, the village of Mystic offers two of the region's marquee draws. The Mystic Seaport Museum is the largest maritime museum in the United States, featuring a recreated 19th-century seafaring village, historic tall ships, and exhibits on New England's whaling and trading past. About a ten-minute drive from the Borough, it draws visitors year-round. A short distance farther, the Mystic Aquarium is another major stop, with a focus on beluga whales, sea lions, and other marine life, making it especially appealing for families traveling with children.
For a beach day and a more traditional New England resort feel, the village of Watch Hill in Westerly, Rhode Island, is roughly a 20- to 25-minute drive east. Known for its sweeping oceanfront, the historic Flying Horse Carousel, and views toward Block Island, it offers a different pace and shoreline than Stonington's own rocky harbors. Together with nearby state parks, the shoreline of Rhode Island, and the entertainment and gaming options of Foxwoods and Mohegan Sun within about a 30- to 45-minute drive, the area gives visitors plenty of reasons to extend a stay.
For short-term-rental owners, Stonington offers a compelling mix of historic character, coastal scenery, and proximity to some of southern New England's most visited attractions. The town's quieter, more residential atmosphere appeals to travelers seeking a genuine New England town rather than a crowded resort, while its central position makes day trips to Mystic, Watch Hill, and the Rhode Island coast effortless. The combination of year-round appeal, walkable villages, and easy access to both Providence and New York City helps sustain steady demand for well-located rental properties.