Regency at Prospect

Regency at Prospect is an award-winning, gated 55+ community developed by Toll Brothers on a 177-acre wooded retreat in the small town of Prospect, Connecticut, tucked into the rolling countryside of New Haven County between Waterbury, Cheshire, Bethany, and Naugatuck. Built between 2006 and 2020 and now fully sold out, the community consists of low-maintenance luxury townhomes — every floor plan featuring a first-floor master suite — arranged along lighted streets with meticulously manicured common areas. It was voted Best 55+ Attached Community in Connecticut by the Home Builders Association of Connecticut, and its centerpiece 7,000-square-foot clubhouse was named Best Community Clubhouse by the same association in 2010. The clubhouse anchors social life and houses a fitness center, an elegant ballroom, a library, a catering kitchen, a card room, and a billiards room. Outdoors, residents enjoy a resort-style pool, a putting green, tennis and bocce courts, and walking and biking trails winding through the community's wooded acreage. A full-time activities director keeps a calendar of events running, supporting active clubs and interest groups that include billiards, bocce, a book club, cards, swimming, and tennis. Pets are welcome, and the gated entrance plus well-lit streets give residents a strong sense of security. Location is one of Regency's quiet advantages. I-84 sits about three minutes from the gate, putting residents within easy reach of Waterbury (about 10 minutes), New Haven (roughly 30 minutes), and Hartford (about 40 minutes). Golf is everywhere — 36 courses fall within a 15-mile radius — and state parks including Southford Falls, West Rock Ridge, and Sleeping Giant are all about 20 minutes away. Shopping ranges from daily-needs stops at Waterbury's Brass Mill Center to the specialty boutiques of Cheshire and the broader New Haven retail corridor. Cultural options include Waterbury's Palace Theater and downtown New Haven's dining, museums, galleries, and Yale-anchored performing arts scene. Bradley International Airport in Windsor Locks is about a 50-minute drive, and the Connecticut shoreline is under an hour south. Saint Mary's Hospital is roughly three miles away for day-to-day medical needs. Because the community is sold out, life here revolves around the resale market — typical pricing lands in the $400s to high $500s for the Tamarac and similar townhome designs, with a median around $525K. HOA fees vary by unit type and run from about $105 to $379 per month, covering lawn care, snow removal, gutter cleaning, and common-area upkeep so homeowners can actually enjoy their retirement rather than maintain it.