Why prep matters most outside
Paint fails when water gets behind it. On the Sound Shore, damp air off Long Island Sound, freeze and thaw cycles in winter and strong summer sun all work on the outside of a house. Peeling usually starts at the bottom edges of clapboards, on window sills, at the tops of porch columns and anywhere gutters overflow. A lasting exterior job starts with fixing those spots.
Good exterior prep usually covers a gentle wash to remove dirt and mildew, scraping all loose paint, sanding the edges smooth, replacing or repairing soft wood, setting nails, caulking open joints and spot priming bare wood. Only then does the finish paint go on.
- Wood clapboard, cedar shingle and fiber cement siding
- Trim, fascia, soffits and window casings
- Porches, railings, columns and steps
- Front doors, garage doors and shutters
- Stucco and masonry where the coating allows it

Rotted wood and repairs
Older homes often have some soft trim, sills or porch parts. Painting over rot traps moisture and the paint fails quickly. Many painters handle small carpentry repairs as part of the job, while larger repairs may go to a carpenter. Ask how repairs will be priced, whether by the piece, by the hour or as an allowance, so there are no surprises.
Lead-safe practices on older houses
If your home was built before 1978, the old paint may contain lead. Federal rules require any contractor paid to disturb that paint to be an EPA Lead-Safe Certified firm and to use lead-safe practices, such as ground covers to catch paint chips, limiting dust and careful daily cleanup. This matters more outside than many people realize, because scraped chips can end up in garden beds and play areas.
The painting season
Exterior painting in southern Westchester usually runs from late spring to early fall. Paint should go on dry surfaces, out of rain and above the minimum temperature on the label. Painters often follow the sun around the house so that walls are not painted in direct midday heat. Book in late winter or early spring if you want a summer slot.
Typical exterior painting costs
Published national ranges for exterior house painting.
| Job | Typical range |
|---|---|
| National typical exterior job (Angi) | $1,819 to $4,551 |
| Per square foot of home (This Old House) | $2.20 to $4.40 |
| 2,000 sq ft one-story (This Old House) | $4,400 to $8,800 |
| 2,000 sq ft two-story (This Old House) | $6,900 to $12,700 |
| 2,000 sq ft three-story (This Old House) | $8,300 to $15,200 |
| Wood siding, per square foot (This Old House) | $1.70 to $3.60 |
Ranges are national averages from the sources below, not quotes. Your price depends on height, siding type, condition, scraping and wood repair, lead-safe requirements and paint choice.
Sources: This Old House, exterior painting cost; Angi, cost to paint a house exterior
Questions homeowners ask
Why is my exterior paint peeling after a few years?
Peeling is usually a moisture problem or a prep problem. Water getting behind the paint from leaks, gutters or unsealed joints pushes it off, and paint over dirt, chalk or loose old coats will not hold. A painter should find the cause before repainting.
Can exterior painting be done in the fall?
Often yes, in early fall, as long as the days are dry and temperatures stay above the paint's minimum while it cures. Late fall gets risky because of cold nights and morning dew.
Should I power wash before painting?
The house needs to be clean, but high pressure can force water into wood and damage old siding. Many painters use a soft wash or low pressure and let the wood dry fully before painting. On pre-1978 homes, washing must follow lead-safe rules.
Other services

House painting
Full interior or exterior repaints for houses of every age.

Interior painting
Walls, ceilings, trim and doors, one room or the whole house.

Cabinet painting and refinishing
A new look for kitchen and bath cabinets without replacing them.

Deck and fence staining
Cleaning, sealing and staining for wood decks and fences.

Power washing and surface prep
Cleaning and prep for siding, decks and walks before paint or stain.

Commercial painting
Storefronts, offices and multi-family buildings.