Exterior painting and cedar restoration for Cheshire, Connecticut homes since 2003. Honest pricing, premium prep, written workmanship warranty — and you don't pay a dollar until the work is done.
Cheshire's housing stock — upscale colonials, Capes, newer subdivisions — is exactly the kind of premium residential work General Painting Co. has specialized in since 2003. We are licensed, insured, BBB A+ rated, and the only painters most Cheshire homeowners need to call.
Cheshire is a long, linear town — the south end is closer to New Haven housing patterns and the north end is more Hartford-style.
Most Cheshire homes were built in eras that used solid wood siding and trim — meaning the difference between a 6-year repaint and a 12-year repaint comes down almost entirely to substrate prep. That is what we do better than competitors here.
We paint homes across all of Cheshire — including Cheshire Center, Mountain Road — and the surrounding New Haven County communities.
Cheshire homes face two distinct exterior threats: Long Island Sound salt-air on the shoreline side and aggressive freeze-thaw inland. Most Cheshire homes need different paint systems on different elevations of the same building, which is why we estimate every face of the home separately rather than blending one number.
For more on Connecticut weather and paint, see our guide to best paint for Connecticut weather and how that informs the systems we recommend.
Exterior paint doesn't fail because of the paint — it fails because of the prep underneath it. Here's everything we do, in order, before paint touches your home.
Every exterior surface gets cleaned of dirt, pollen, mildew, moss, chalking, and oxidation before any prep tool touches the wood. The single biggest reason cheap paint jobs peel is that they're painted over contamination.
Every bit of loose or failing paint is hand-scraped off, with edges feathered smooth so the new paint lays down flat instead of in visible ridges.
Rotted trim, fascia, and siding sections replaced with like-for-like material. All bare wood and every spot-primed area gets a high-adhesion primer before topcoat.
Every siding-to-trim seam, window frame, door frame, corner board, and gap gets a tight bead of exterior-grade caulk. Keeps water out and makes the lines look crisp.
Premium paint applied with brush and roller for proper film thickness, with back-brushing to work the paint into the grain. Two full coats — never one heavy coat.
We walk the property with you before calling it done. Anything you flag gets touched up the same day.
A small sample of premium homes painted by General Painting Co. across Cheshire and surrounding south central towns.
We price every project line by line. Here's what's typically itemized in a Cheshire estimate:
Benjamin Moore · Sherwin-Williams · Sikkens · Cabot · California Paints. No "contractor grade" jug paint. The paint is the smaller part of the cost — using the wrong one costs you years of finish life.
Full repaint pricing for Cheshire homes typically falls in the $4,500–$14,500 range, depending on home size, stories, trim detail, prep condition, and paint grade.
| Home size | Siding only | Siding + trim | Full repaint (premium prep) |
|---|---|---|---|
| ~1,500 sq-ft Cape | $3,800–$5,500 | $5,200–$7,800 | $6,200–$9,500 |
| ~2,500 sq-ft Colonial | $5,500–$8,500 | $7,800–$11,500 | $9,500–$14,500 |
| ~4,000 sq-ft larger | $8,000–$12,000 | $11,500–$16,500 | $14,500–$20,000 |
| 6,000+ sq-ft estate | by quote | by quote | $22,000+ |
For a town-specific deep-dive, see our Cheshire exterior painting cost guide.
For a typical 2,500 sq-ft colonial in Cheshire a full exterior repaint runs $4,500–$14,500, depending on prep condition, story count, trim detail, and paint grade. Larger estates and full cedar restorations run higher. Every Cheshire estimate we issue is written, itemized, and free.
Properly prepped two-coat exterior systems on Cheshire homes typically hold 10–12 years on north-facing walls and 7–9 on south- and west-facing walls. With premium paints (Benjamin Moore Aura, Sherwin-Williams Emerald) and our 6-step full-prep protocol, you should never see early peel.
Yes. General Painting and Decorating, LLC is fully licensed and insured to work in Cheshire and across Connecticut and New York. Every project comes with a written workmanship warranty that's transferable if you sell the home.
After. We are one of the few CT exterior contractors that asks for nothing up front — you pay when the job is complete and you've walked the property with us. It's how we ensure every customer is fully satisfied before we get paid.
April through October is the proper window. Surface temperature must stay above 50°F and humidity low enough for the paint to cure. We book the summer calendar by May, so booking early is the difference between getting your project done in your preferred season vs. pushing into fall.
Yes — and we do it as part of the project, not as a separate trade. Rotted shake or shingle gets replaced with like-for-like material before any topcoat goes on. Our standard cedar protocol uses Sikkens stains where the natural wood grain should show through and Benjamin Moore Aura where it gets a solid color.
Free on-site estimate within 48 hours. No pressure, no pushy sales — just an honest written quote you can take to other contractors.