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The highest-performing listings in Caldwell.
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Generally Investor friendly
STRs appear allowed in Caldwell under general zoning/housing codes with moderate permitting (annual registration, safety inspections) and insurance but no published city‑specific STR ban or caps. Enforcement is likely to tighten as nearby Essex County municipalities adopt stricter rules, but the current regime remains manageable for investors.
Local STR Agent
STR specialist · Caldwell, NJ
Caldwell is a small, walkable borough in Essex County, in the northern part of New Jersey, with a population of roughly 8,000 residents. The community has a quiet, tree-lined character that mixes older single-family homes, a compact downtown of cafés and small shops, and the leafy campus of Caldwell University, a Catholic liberal arts institution that has long given the borough a college-town feel. Caldwell sits about 25 miles west of New York City, making it a convenient suburban stopover for travelers who want a quieter base than the city itself, and it functions as a comfortable gateway to the wider Essex County area, including the surrounding towns of the Caldwells, Montclair, West Orange, and Livingston.
One of the borough's most distinctive landmarks is the Grover Cleveland Birthplace, a modest 1830s house on Bloomfield Avenue that has been preserved as a National Historic Site. Operated by the National Park Service, the site commemorates the only U.S. president born in New Jersey and offers a small but well-curated look at 19th-century domestic life, with period furnishings and a visitor center. It is within easy walking distance of the downtown and is a natural stop for history-minded visitors staying in the area.
A short drive south brings guests to the Essex County South Mountain Reservation, an expansive county park that spans parts of West Orange, Maplewood, and Millburn. The reservation is known for its wooded hiking and biking trails, scenic overlooks of the New York skyline, and waterfalls, and it borders the popular Turtle Back Zoo, which has grown into one of the larger family-oriented zoos in the state. Together the reservation and zoo make a full-day outing within about 10 minutes of Caldwell.
Just to the east, the township of Montclair offers a lively complement to Caldwell's quieter pace, with a walkable downtown, galleries, the Montclair Art Museum, and a well-known film and music scene centered along Bloomfield Avenue. Slightly farther afield, the Watchung Reservation in Union County adds another option for hiking, horseback riding, and nature programs, while Manhattan is a roughly 45-minute train ride away via NJ Transit.
For short-term rental owners and guests alike, Caldwell's appeal lies in this balance: a peaceful, small-town New Jersey base with a historic landmark in the heart of town, a respected university lending year-round activity, and easy access to some of the most visited parks, cultural venues, and family attractions in the greater Newark–New York corridor.