​Following a divorce, and nearing retirement after a 47-year nursing career, Ms. Aponte was ready for a change. So a year and a half ago, she left Westborough, Mass., for the Walnut Beach section of Milford, where her daughter had moved 11 years earlier. She bought a four-bedroom house with a yard big enough to accommodate her nine grandchildren, paying $320,000. The home is a five-minute drive from Walnut Beach, or a 12-minute walk to the three-quarter-mile boardwalk that connects Walnut Beach to Silver Sands State Park.

“It’s a pretty New England town that’s just big enough, but not too big,” said Ms. Aponte, 68, who attends the free summer concerts and weekly farmers market at Walnut Beach, and participates in programs at Milford’s senior center and the local YMCA. She is also happy to be closer to New York City, and makes frequent train trips there, taking advantage of Metro-North Railroad’s senior discount. Now she is hoping to talk her sons into moving to Milford.

“If any of my kids in Massachusetts were willing to move, I’d tell them to only consider Milford,” Ms. Aponte said.

What You’ll Find

Tucked beside the Housatonic River and hugging a long stretch of the Long Island Sound, Milford has a close relationship with the water. The beaches provide much of the city’s social fabric during the summer, as do the boat-filled marinas and busy harbor. Added to that are the many ponds, inlets and salt marshes, and a downtown waterfall that offers a picturesque backdrop for City Hall.

Image 11 SMITHS POINT ROAD | A three-bedroom, two-bathroom house on the water in a gated community, built in 1998 on 0.14 acres, listed for $898,500. 203-623-9844 Credit... Tony Cenicola/The New York Times

Beyond the shoreline, this 23.6-square-mile city extends north, bisected by I-95 and a highly commercial stretch of Boston Post Road, with several distinct neighborhoods and a highly varied housing stock. North of the Post Road are farmlands and two large housing developments built in the past 20 years, while the streets surrounding the downtown are lined with 19th-century homes. Sprinkled throughout the city are the hundreds of Cape Cod-style houses and split-levels built in the 1950s for returning World War II vets, as well as a number of condominium complexes.

Image 222 OLD FIELD LANE | A four-bedroom, two-and-a-half-bathroom renovated Cape Cod-style house, built in 1951 on 0.21 acres, listed for $649,000. 203-590-0115 Credit... Tony Cenicola/The New York Times

“It’s amazing the different types of houses we have here in Milford. You can get something for $190,000 or $2.2 million, so there’s something for everyone,” said Ms. Zink, who grew up in a mobile-home park owned by her family that once sat on the Post Road before moving in 2005 to make way for a Walmart. Now called Ryder Woods and under new ownership, the mobile park is home to about 200 families.