Old Post Road Historic District Home Insurance in Fairfield, CT

By Jon Merwin, Founder and CEO

The Old Post Road runs through the oldest part of Fairfield, past the town green and down toward the beach. Along it stands a remarkable run of eighteenth- and nineteenth-century houses: a handful that came through the 1779 burning of the town, many built in the decades after it, and a run of Greek Revival homes from the 1800s. It was Fairfield’s first local historic district, and the rules that protect it also shape what it takes to repair one of these houses after a fire, a fallen tree or a winter leak.

We are a family-owned independent insurance agency, working since 2005. For an Old Post Road house we compare options from 40+ carriers, then fit flood, valuables, autos and an umbrella around the home policy. We serve Connecticut from our Connecticut office and by phone, email and online. Call us at (603) 431-4020 with questions about your house.

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Burned in 1779, rebuilt along the Post Road

On the morning of July 7, 1779, more than 2,000 British soldiers under General William Tryon came ashore at Fairfield Beach. For two days they raided and burned the town, according to the Fairfield Museum (Fairfield Museum and History Center). The town’s historic district guidelines list the losses: houses, barns, shops, schools, the meeting house and the courthouse (Fairfield historic district design guidelines).

A few houses survived. The museum’s photo archive says the Rowland House at 952 Old Post Road, built by Andrew Rowland in 1760, was spared because of a courtesy Rowland had once shown a British officer (Fairfield Museum photo archive). The Isaac Tucker House of 1766 is another survivor; by tradition a servant hiding upstairs put out the fire, and burn marks remain inside (Historic Buildings of Connecticut). Many of the houses along the road today went up after the war, alongside the collection of Greek Revival houses the town singles out in its description of the district.

The nineteenth century added more layers. The guidelines note that the New York and New Haven Railroad reached Fairfield in 1848, bringing day-trippers from New York and wealthier visitors who built summer houses, and that the Connecticut Turnpike cut through established neighborhoods in 1958. The Old Post Road district kept its older character through both.

Where the district runs and who reviews changes

Fairfield adopted a local historic district ordinance under the state’s enabling law, sections 7-147a through 7-147y of the General Statutes (CGS chapter 97a). The Old Post Road district came first, in 1962, followed by Southport and Greenfield Hill in 1966, and all three were placed on the National Register of Historic Places in 1971. The design guidelines list the district by address: Old Post Road numbers 85 through 1047, Beach Road 205 through 370 plus number 140, Belmont Street 90 through 110, and South Benson Road numbers 110 and 131.

Inside those limits, demolition, new construction and exterior alterations visible from a public way need approval from the Historic District Commission. Starting work before the commission decides whether a project is exempt can bring a stop-work order from the town. Our Greenfield Hill and Southport pages cover Fairfield’s other two districts.

The surrounding neighborhood in Census figures

Census tract 615 takes in the Old Post Road district along with nearby blocks, so its figures describe the wider neighborhood rather than the district alone. The Census Bureau’s 2020–2024 estimates put about 4,800 people and 1,787 homes in the tract (ACS B01003; ACS B25001). Most are single-family houses, but the tract also has about 290 two-family houses and about 160 buildings with three or four units, many of them older homes that were divided over time (ACS B25024).

Half the owner-occupied homes are valued above roughly $888,500, and about 580 are valued at $1 million or more, including some 180 at $2 million-plus (ACS B25077; ACS B25075). The median income is about $209,500 (ACS B19013). Both run above Fairfield as a whole, where the median value is about $780,500 and the median income about $172,400 (ACS B25077, Fairfield town; ACS B19013, Fairfield town). Around 420 homes in the tract predate 1940 (ACS B25034).

Repairs after a loss: Repair Orders and Certificates of Appropriateness

The commission’s guidelines set out two routes for exterior work, and which one a repair takes affects how fast you can get the house back together.

The quicker route: a Repair Order

Routine, minor work that does not change how the house looks can be approved through a Repair Order instead of a hearing. The guidelines give examples:

• Identical replacement of existing windows and doors.
• Repair of existing windows and doors, and storm windows or doors that match the existing design.
• Maintenance and repair of existing roofing with no change in design, scale or appearance.
• Structural repairs that do not alter the exterior.
• Replacement of clapboards, shingles or other siding with identical material.

You file the form, sometimes with photos, drawings or product data. If the job needs a building permit, the signed Repair Order comes before the permit. The guidelines suggest calling the commission chair or a designee before starting, to confirm the work qualifies.

The longer route: a Certificate of Appropriateness

Anything else visible from a public way, such as a change in materials, a new design or a rebuilt porch that differs from the old one, needs a Certificate of Appropriateness. That means an application, a public hearing with published notice, and a decision by the commission before the building department issues a permit. Certificates are generally good for twelve months and can be extended for six. A hardship variance is available only in exceptional cases.

Materials the commission expects

The guidelines put repair first, then replacement with like materials when repair is not feasible. Vinyl, fiber cement and other synthetic products are, for the most part, not acceptable in a local district, and deferred maintenance is not accepted as a reason to use them. Even chimney work has rules: historic brick is softer than modern brick, and the guidelines warn that a mortar mixed with Portland cement can crack it.

What that means for your policy

• Estimate the rebuild in traditional materials. An estimate built on vinyl siding and stock windows will come up short. Base the dwelling limit on wood clapboards, true divided-light windows, period trim and the right roofing.
• Extended replacement cost. Specialist trades are in demand after a regional storm. Extra coverage above the limit helps when the bids come in high.
• Ordinance or law. Code-required upgrades to wiring, structure and egress can be triggered by a covered repair; this coverage helps pay for them.
• Additional living expense. A hearing, a permit and scarce materials add months. Make sure the policy can house the family for the whole job.
• Document the details. Photograph cornices, doorways, windows and interior millwork now. Pictures help an adjuster agree on what has to be replaced and how.

Our historic home insurance post covers older houses in general.

Flood rules and historic houses near the shore

The district runs from the town green toward the water along Beach Road, and Fairfield’s beach neighborhoods took heavy flooding in recent storms. A 2016 Army Corps of Engineers report found that Fairfield had the largest number of damaged homes in Fairfield County from Hurricane Sandy, much of it from wave attack on the beachfront and surge flooding in the neighborhoods between Pine Creek and Ash Creek (U.S. Army Corps of Engineers coastal report, 2016). Check your address on the FEMA flood map before assuming the district is out of reach.

Historic houses get some room under federal floodplain rules. When repairs or improvements cost at least half of a building’s market value, the building usually has to be brought up to current flood standards, often by raising it. The federal definition of substantial improvement leaves out alterations to a designated historic structure, as long as the work does not cost the building that designation (44 CFR 59.1). How that applies to a particular house is decided locally by the town’s building and floodplain officials.

None of that replaces flood insurance. Homeowners policies exclude flood. New NFIP flood policies go through Selective, and on the private side we compare CatCoverage, Flow Flood, The Flood Insurance Agency, Neptune Flood, Aon Edge and Beyond Floods. Our Fairfield flood insurance page maps where the town floods.

Two-family houses and rentals in the district

Plenty of older Fairfield houses have been divided into two or more units, and the Census counts several hundred of them in the surrounding tract. If you live in one unit and rent the other, the homeowners policy has to be written for an owner-occupied multi-family house. If you own a house in the district and rent all of it, it belongs on a landlord or dwelling policy; we place those with Vermont Mutual, Andover, Liberty Mutual, Hanover, Providence Mutual and Foremost. Our Fairfield landlord insurance page covers leases, tenants and liability.

Choosing carriers for an Old Post Road house

Higher-value houses in the district usually start with Cincinnati and Chubb. They are similar high-value carriers, and both write homes at any dwelling limit. Their underwriters look closely at older construction, at updates to wiring and heating, and at protective devices, and a side-by-side quote shows which one suits your house.

Older homes that fit standard markets go to a wider list. Liberty Mutual, Providence Mutual, Openly, Andover, Stillwater, Hanover, National General, Foremost, Vermont Mutual and Cincinnati all write Connecticut homes through us. Read our Fairfield homeowners insurance page for the town as a whole.

Collections are common in old houses: antiques, art, silver and jewelry often need their own schedule. Liability should be set high, with a personal umbrella over the home and cars.

An Old Post Road coverage checklist

• Confirm your address against the district’s street-number list.
• Base the dwelling limit on traditional materials and period details.
• Review extended replacement cost, ordinance or law and additional living expense.
• Photograph exterior and interior details and keep the files off site.
• Keep records of updates to the roof, wiring, plumbing and heating.
• Check the flood map and compare NFIP and private flood if you are near a zone.
• Decide how divided or rented units are written.
• Schedule antiques, art, silver and jewelry, and set umbrella limits.

Related pages

See Fairfield insurance, Fairfield condo insurance, Fairfield car insurance, the Fairfield County hub, the Connecticut hub and Connecticut high-value home insurance.

Request a quote for your Old Post Road house

Tell us how the house is built and what it holds, and we will compare 40+ carriers for you. Request a quote. There’s no obligation to buy. We don’t charge any fees. Start with the form below, our quotes page or a call to (603) 431-4020. Our client feedback page shows the 1,000+ Google reviews and over 2,000 testimonials behind our name.

Frequently asked questions

How do I know whether my house is in the Old Post Road Historic District?

The town lists the district by street number. Its design guidelines include Old Post Road from 85 to 1047, Beach Road from 205 to 370 plus number 140, Belmont Street from 90 to 110, and 110 and 131 South Benson Road. If your address is on that list, exterior work visible from a public way goes through the Historic District Commission.

After a storm, can I replace damaged clapboards or windows without a public hearing?

Often, yes, if the replacement is identical. The commission’s guidelines let routine, like-for-like repairs that do not change the appearance go through a Repair Order instead of a full Certificate of Appropriateness. You file the form, and if a building permit is needed, the signed Repair Order has to come first.

Will the commission let me use vinyl or fiber cement siding after a loss?

Generally not. The guidelines favor repairing historic material, then replacing it with like materials, and say alternative materials are, for the most part, not acceptable in a local district, with limited case-by-case exceptions. That is why your dwelling limit should be based on wood and other traditional materials.

Does historic status change the flood elevation rules after a big loss?

It can. Federal rules leave alterations to a designated historic structure out of the substantial improvement definition, as long as the work does not cost the building its historic designation. Whether that applies to your house is up to the town’s floodplain officials, and it does not replace flood insurance, which homeowners policies exclude.

How long can a historic repair take, and is the extra time covered?

A project that needs a Certificate of Appropriateness goes to a public hearing, and certificates are generally good for twelve months. Specialized trades and materials can stretch the job further. Additional living expense pays reasonable costs to live elsewhere during a covered repair, so set it high enough for a long project.

Which carriers do you use for homes in the district?

For higher-value houses we compare Cincinnati and Chubb, two similar high-value carriers that write homes at any dwelling limit. Other Connecticut homeowners carriers get a look when they suit an older house better.

What should I gather before requesting a quote?

Year built, square footage, siding, roof and window materials, dates of wiring, plumbing and heating updates, any elevation certificate, photos of the exterior details, and your current declarations pages. Call (603) 431-4020 or fill in the form on this page. Request a quote. There’s no obligation to buy.

Sources

• Town of Fairfield, Design Guidelines for Historic Districts and Historic Properties
• Fairfield Museum and History Center: the 1779 burning of Fairfield
• Fairfield Museum photo archive: Rowland House, 952 Old Post Road
• Historic Buildings of Connecticut: the Isaac Tucker House (1766)
• Connecticut General Statutes, chapter 97a (historic districts)
• Census Bureau ACS 2020–2024, Tract 615 units in structure (B25024)
• Tract 615 median home value (B25077)
• Tract 615 owner-occupied home values (B25075)
• Tract 615 median income (B19013)
• Tract 615 year structure built (B25034)
• Fairfield town median home value (B25077)
• U.S. Army Corps of Engineers, coastal engineering report, Fairfield Beach (2016)
• 44 CFR 59.1, NFIP definitions
• FEMA Flood Map Service Center