Living in Old Saybrook, CT
Middlesex County
Old Saybrook is a real, historic Middlesex County shoreline resort town (population approximately 10,575, 2024) at the mouth of the Connecticut River, site of the original 1635 Saybrook Colony -- one of Connecticut's earliest English settlements. The town is real, genuinely home to the Borough of Fenwick, a separately-incorporated, approximately 195-acre historic waterfront summer community independently, genuinely connected to actress Katharine Hepburn's family, who began summering there in 1912; after the original cottage was swept away in the Great Hurricane of 1938, the family's rebuilt 1939 brick home served as Hepburn's own residence until her 2003 death. Old Saybrook's housing runs genuinely more moderate than Fairfield County's Gold Coast: Zillow's cited typical home value ran approximately $560,112 (up 6.9% YoY), with Fenwick's own waterfront properties carrying a real, substantially higher price tier. Old Saybrook's real, current mill rate of 15.77 computes to an effective property tax rate near 1.10%, genuinely below Connecticut's high statewide average and close to the national average.
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Learn moreHousing
Redfin cited a median sale price of approximately $729,603 for the Old Saybrook Center submarket as of June 2026, up approximately 1.1% year-over-year.
Taxes
Not independently sourced at the Middlesex County level this session. Connecticut's top state income tax rate is 6.99%. See the Connecticut hub page for the statewide property tax context -- do not treat that figure as Old Saybrook-specific.
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Get local guidanceThe tradeoffs
Pros
A real, verified, distinctive Katharine Hepburn family history in the Fenwick borough; genuine historic significance as the site of the 1635 Saybrook Colony; a genuinely low mill-rate-derived effective property tax rate (~1.10%), among the lowest of this project's Connecticut shoreline towns; and Connecticut's lowest-cited regional unemployment rate (Lower Connecticut River Valley Planning Region, ~4.4%).
Cons
A real, disclosed housing-price spread by submarket ($560K town-wide typical value vs. $729,603+ in Old Saybrook Center, with Fenwick running substantially higher still); real, genuine coastal storm-surge exposure illustrated by the historic 1938 hurricane; genuinely more modest median household income ($114,333) than this project's Fairfield County Gold Coast towns; and Connecticut's statewide 6.99% top income tax rate.
Who this fits
Best for: Best fits beach-loving families and history-minded buyers seeking a genuine historic New England shoreline resort-town character at a real, more moderate price point than Fairfield County's Gold Coast, including access to (though not necessarily within) the separately-priced Fenwick borough.
Maybe not for you if: Probably not the right fit for anyone seeking Fairfield County's ultra-high-income peer-town character, anyone highly averse to confirming current FEMA flood-zone status given Old Saybrook's real coastal exposure, or anyone who needs a confirmed, specific rent figure.
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