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Diana and Dan Colcord spent the spring looking for a place to downsize from their large home in Madison, Conn. After a hunt that spanned the Connecticut coastline, from New Haven to Old Lyme, they found the ideal landing place in Old Saybrook, a Middlesex County town at the junction of the Connecticut River and Long Island Sound.
One day after a two-bedroom condominium listed for $489,000 in a small complex close to the town center, the Colcords put in an offer. Competing offers followed, but the couple persisted, finally getting the home for $560,000.
A month later, they are enjoying what Ms. Colcord, 58, calls their new walkable lifestyle: Restaurants are just around the corner, and the Katharine Hepburn Cultural Arts Center (honoring Old Saybrook’s most famous former resident) is two blocks away. An added bonus: Their complex overlooks North Cove, an inlet on the Connecticut River.
“We were sold by the view and being able to walk one block to get to downtown,” Ms. Colcord said while lunching with Mr. Colcord, 68, by the complex’s pool. “We were fortunate to win it.”
Joel Blum, a financial adviser, moved to Old Saybrook from Westbrook, Conn., earlier this year, after spending eight months looking for a new home. An avid boater, Mr. Blum, 41, found the ideal house within walking distance of the Saybrook Point Resort and Marina, where he keeps his boat. (His 6-year-old daughter also enjoys the marina’s swimming pool.)
In January, he closed on a 3,000-square-foot ranch house on half an acre, with views of North and South Cove, paying $1.315 million. “I spend a lot of time in East Hampton and Montauk,” he said, “and it’s convenient to go across the Sound to Long Island.”
What You’ll Find
With its numerous coves and inlets, Old Saybrook is understandably oriented around the water. There are at least five private beach associations that maintain their own beaches for residents, as well as two town beaches. There are also six marinas, two yacht clubs and a public boat launch.
The year-round population of roughly 10,000 skews older, with a median age of 52, compared with the statewide median of 41.
“It’s a place where middle-class people built cottages generations ago and left them to their kids,” said Bart Gullong, 75, who grew up in Old Saybrook, as did his father. “Now, many of those houses have been winterized. And as people retire, they live in them year-round.”
The broad avenue that is Main Street is lined with restaurants, shops and specialty markets. Big-box stores and car dealerships dot Route 1, which cuts east-west through town.
Below Route 1 are Saybrook Point, which has a public park with a waterfront walkway and miniature golf, and the borough of Fenwick, which occupies the peninsula at the mouth of the river. Fenwick began as a summer retreat for Hartford’s elite in the late 19th century, and is home to some of the town’s most expensive properties. Residents pay taxes to the town and the borough, which strictly monitors changes to properties in its historic district and limits the times when construction and yard maintenance may be done.
The privately owned Saybrook Breakwater Lighthouse, a sparkplug-style lighthouse at Fenwick Point, is featured on the state’s “Preserve the Sound” license plates. Opposite that structure, and on shore, is the Lynde Point Lighthouse, which the federal government is currently offering for free to a municipality or nonprofit that will maintain it and open it to the public. (The borough does not currently allow public access to the site.)
The borough of Fenwick has applied to take possession, but some lighthouse fans, including Mr. Gullong, worry that the borough may not make it truly accessible. They are calling for a nonprofit to step in.
“The Connecticut River Gateway Commission is going to partner with another organization and make an application,” said Mr. Gullong, who now lives in Waterford, Conn. “They would renovate it and make sure it’s available to the public.”
What You’ll Pay
As in most places these days, housing inventory is low in Old Saybrook. In late July, there were about 20 active listings for single-family homes, from a one-bedroom, 600-square-foot cottage in a beach association, listed for $469,000, to a four-bedroom, 5,500-square-foot waterfront home on 3.5 acres, listed for $4.8 million.
“The market is a bit slower than last year, due to rising interest rates and low inventory,” said Sharon Linder, an agent with Berkshire Hathaway HomeServices New England Properties. “However, there is still a lot of activity with multiple offers. Many of the transactions are cash.”
The median sale price for a single-family home during the 12 months preceding mid-July was $639,000, she said. The median price for a condominium was $530,000.
“Houses are lingering a little longer on the multiple listing service because we are seeing fewer buyers,” said Rose Ciardiello, an agent with William Raveis Real Estate. “But it’s still a good market for sellers, because the buyers that are out there are strong and ready to go.”
Homes in the beach areas “are really hot, and prices have been shooting up,” said Andrew O’Reilly, an agent with Seaport Real Estate Services. “And there are a lot of people competing for homes in the middle price range — about $425,000 to $899,000.”
Property taxes are lower in Old Saybrook than in many surrounding shoreline towns, an attractive feature for retired buyers, Ms. Ciardiello said. The mill rate — the amount of tax payable per dollar of assessed value — is 20.08 in Old Saybrook, compared with, for example, 23.5 in Old Lyme and 33.25 in Guilford.
The Vibe
Although the population swells during the summer months as part-timers return, Old Saybrook is a fairly quiet place year-round.
Walkers stroll the causeway across South Cove, running from Saybrook Point to Fenwick. Beachgoers comb the white sands of Harvey’s Beach, which has a playground and a bathhouse. Golfers enjoy the water views on the nine-hole public course in Fenwick.
The Saybrook Point Resort is a popular place to meet for dining, indoors and out, Ms. Ciardiello said. Among the more casual local hangouts are Skippers Seafood and the Monkey Farm Cafe, both on Boston Post Road.
Annual community events include a Memorial Day parade and the Torchlight Parade, held in the evening on the second Saturday of December. It features fife-and-drum corps from around New England and floats decorated with lights.
“It’s gone on for more than 50 years,” said Scott Giegerich, a town selectman. “Everyone comes out and goes up and down Main Street.”
The Schools
The Old Saybrook school district is small, serving around 1,000 students in total. About 78 percent identify as white, 14 percent as Hispanic or Latino, 4 percent as Asian, and 3 percent as two or more races, according to state data.
The Kathleen E. Goodwin Elementary School serves students in prekindergarten through fourth grade. Students in fifth through eighth grades attend Old Saybrook Middle School.
Old Saybrook Senior High School has about 350 students. In 2021-22, the average SAT scores were 510 in reading and writing and 499 in math, compared with state averages of 501 and 486.
Saint John School, a private Catholic institution, serves students in prekindergarten through eighth grade. Full tuition for the 2022-23 school year was $5,245.
The Commute
Amtrak trains run from Old Saybrook Station to Penn Station in Manhattan. The trip takes about two and a half hours; a one-way coach fare ranges from $50 to $120, depending on when the ticket is purchased.
Alternatively, commuters can take a Connecticut Shore Line East train to Union Station in New Haven, about a 40-minute ride; the one-way fare is $7.25. From there, the trip to Grand Central on Metro-North’s New Haven Line takes about an hour and 40 minutes; the one-way peak fare is $23.50.
Driving to Midtown can take two and a half to three and a half hours, depending on the time of day and traffic.
The History
Twenty years ago, on June 29, 2003, film star Katharine Hepburn died at age 96 in her family’s beloved summer home in Fenwick. The long, white-brick house fronts Long Island Sound, where Ms. Hepburn swam regularly. It dates to 1939, having been rebuilt after the original circa-1870 structure was destroyed in a 1938 hurricane. In her memoir, “Me: Stories of My Life,” Ms. Hepburn recalled escaping out the dining room window during the storm, then watching from higher ground as the house “just sailed away.” The property last sold for $11.5 million in 2017.
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