Roofing in Simsbury, CT: Repair & Replacement
Ballpark prices for Simsbury roof projects, how to choose between asphalt, cedar and metal, and what the historic district commission looks for on East Weatogue Street.
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In Simsbury, an asphalt shingle replacement typically runs $10,000 to $25,000+, cedar shake $20,000 to $40,000+ and metal $20,000 to $45,000+ as Connecticut ballparks. Smaller repairs commonly cost $350 to $1,500. A Class inspects for free and writes up the exact price before any work.
Most Simsbury roofs date from the postwar boom onward
Simsbury had about 4,800 residents in 1950 and nearly 17,500 by 1970, then grew more slowly to about 24,500 in 2020. Most houses in town date from that 1950s-to-1970s surge or later, with the oldest homes concentrated in Simsbury Center, East Weatogue and Terry’s Plain.
That means a large group of roofs on second or third replacements, often on colonials and capes with simple gables, plus bigger newer homes with complicated roofs. Prices follow those shapes: a plain gable roof costs far less per square foot than one broken up by dormers, valleys and skylights.
Ballpark prices for Simsbury roof projects
Connecticut ranges for 2026, for planning. The firm number for your house comes after a free inspection on site.
| Project | Ballpark | Good fit when |
|---|---|---|
| Asphalt shingle replacement | $10,000–$25,000+ | You want the most roof for the money on a typical house |
| Cedar shake replacement | $20,000–$40,000+ | The house had wood originally or the look matters, and the roof gets enough sun to dry out |
| Metal roof replacement | $20,000–$45,000+ | You plan to stay for many years and want a roof that typically lasts 40 to 70 |
| Minor roof repair | $350–$1,500 | The roof is sound overall and the damage is local |
| Emergency tarping | $300–$1,000 | A limb or wind has opened the roof and rain is on the way |
| Gutter guards | $1,000–$3,000 | Trees drop leaves and needles into the gutters every fall |
Roofing price check
Typical Connecticut ranges for common roofing jobs.
What changes the price on a Simsbury house
Shape before size
Each valley, dormer, skylight and wall joint needs flashing and hand work, so a cut-up roof costs more per square foot than a long plain gable.
What comes off
One layer of asphalt is a routine tear-off. Two layers, or wood shakes hiding under asphalt, add labor and disposal.
The deck underneath
Soft or delaminated sheathing found during tear-off has to be replaced before anything new goes on, and a good estimate prices it per sheet.
Switching materials
Moving to metal or cedar can mean new trim, different flashing details and changes at the ridge and eaves, which a like-for-like reroof avoids.
Height and access
Steep pitches, three-story walls and tight lots under big trees add staging and time.
Asphalt, cedar or metal: how to choose
Architectural asphalt shingles typically last 20 to 30 years and cost the least up front, which is why most Simsbury houses have them. Cedar shakes typically last 20 to 40 years when they can dry between storms, and they suit older houses and wooded settings, but they need more upkeep and fare poorly in deep shade. Metal costs the most, yet it typically lasts 40 to 70 years and sheds snow readily.
Ask yourself how long you expect to stay, how much shade the roof gets, and whether a historic commission or a homeowners association limits your choices. Our guides to the best roofing material for Connecticut and metal roofing go into more detail.
East Weatogue and the historic district commission
Simsbury’s Historic District Commission reviews roof replacements in its district, and East Weatogue Street has seen a steady run of them, from matching asphalt to new wood shakes. The commission’s handbook favors repairing a roof where possible and, when replacement is needed, taking the original shape, features, color and materials into account.
If your house is in the district, talk to the town before choosing a material, and ask how long an approval stays valid, since a certificate can lapse if materials are slow to arrive. Photos of the existing roof and a written description of the proposed shingles, flashing and trim make the application easier to review.
Big trees and the 2011 storm
Simsbury is a town of large trees; it is home to the Pinchot Sycamore, the biggest tree in Connecticut. When the October 2011 snowstorm struck while leaves were still on the branches, public works crews afterward collected some 195,000 cubic yards of brush and debris in Simsbury alone.
If a storm puts a limb through your roof, the first priority is a tarp to keep water out, which runs about $300 to $1,000 as a ballpark. Photograph everything before the cleanup and contact your insurer promptly. Storm damage is often covered while wear is not, but the insurer decides; see roof insurance claims in CT.
Before the next big storm, it is worth having an arborist look at any large tree that leans toward the house or hangs over the roof. Removing one dead limb costs far less than the roof repair it could cause.
How we price and carry out a Simsbury roof
Call us or send a callback request. A roofer then visits at no charge, inspects the shingles, flashing and attic, and photographs the roof from above with a drone and up close on the surface.
With those photos you receive a written price, with the options laid out side by side if you are weighing materials. We start only after you approve, protect the beds and walkways during the work, and leave with the debris, sending photos of the finished roof once it is done.
Chimneys and nearby towns
For chimney sweeping and restoration, see our Simsbury chimney page. We also roof in Avon and across Hartford County; the roofing overview lists every service we offer. To book the free inspection, phone (203) 779-6787.
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- Free roof inspection and written estimate
- Photos of everything we find
- A written price before any work starts
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Roofing help in Simsbury
Free roof inspection, photos of what we find and a written price before any work. Licensed and insured in Connecticut.