28 Church St, Winchester, MA 01890
Painting in Winchester, Massachusetts
Compare contractors serving Winchester, Middlesex County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Winchester — including 1 based in town.
Contractors serving Winchester
Claimed listings within 5 miles come first, then the rest by rating, then distance. Google ratings as of October 2026. How we list and rank contractors
- Obie and Sons Contracting LLCBased in Winchester★★★★★5.0 Google rating
- Fitzgerald Painting ServicesServes Winchester · 1.8 mi★★★★★5.0 Google rating
10 Draper St STE 18, Woburn, MA 01801
- Orige General PaintingServes Winchester · 2.0 mi★★★★★5.0 Google rating
476 Main St, Woburn, MA 01801
- GPA ContractingServes Winchester · 2.4 mi★★★★★5.0 Google rating
96 Summer St, Arlington, MA 02474
- Boston Best Painter LLCServes Winchester · 2.9 mi★★★★★5.0 Google rating
10 High St #15, Medford, MA 02155
- HKF Construction, Inc.Serves Winchester · 2.9 mi★★★★★5.0 Google rating
284 Boston Ave, Medford, MA 02155
- HB HOME IMPROVEMENTServes Winchester · 3.1 mi★★★★★5.0 Google rating
740 Main St unit a, Woburn, MA 01801
- SYM Painting LLCServes Winchester · 3.2 mi★★★★★5.0 Google rating
2 Summer St, Medford, MA 02155
- SouzapaintingcoServes Winchester · 3.2 mi★★★★★5.0 Google rating
17 Almont St, Medford, MA 02155
- Gilbert Carey PaintingServes Winchester · 3.4 mi★★★★★5.0 Google rating
3 Cheswick Rd, Arlington, MA 02474
- Alpha Construction and Design Inc.Serves Winchester · 3.5 mi★★★★★5.0 Google rating
41 Browning Rd, Arlington, MA 02476
- Star PaintingServes Winchester · 3.6 mi★★★★★5.0 Google rating
50 Cushing St, Medford, MA 02155
- Medford House PaintingServes Winchester · 3.7 mi★★★★★5.0 Google rating
102 Golden Ave, Medford, MA 02155
- Roma Home LLCServes Winchester · 4.1 mi★★★★★5.0 Google rating
245 Pearl St, Malden, MA 02148
- Colleary ConstructionServes Winchester · 4.2 mi★★★★★5.0 Google rating
50 Leonard St Suite 202, Belmont, MA 02478
- Slims Painting LLCServes Winchester · 4.3 mi★★★★★5.0 Google rating
51 Pleasant St #1157, Malden, MA 02148
- Blue Ocean PaintingServes Winchester · 4.3 mi★★★★★5.0 Google rating
3 Perham Ave, Melrose, MA 02176
- Pontes Painting IncServes Winchester · 2.1 mi★★★★★4.9 Google rating
76 Winn St Suit 2C, Woburn, MA 01801
- Lou's Painting CompanyServes Winchester · 3.1 mi★★★★★4.9 Google rating
14 Pleasant St, Stoneham, MA 02180
- Oliveira Painting IncServes Winchester · 3.7 mi★★★★★4.9 Google rating
2564 Massachusetts Ave, Cambridge, MA 02140
- S.C.H. PaintingServes Winchester · 4.3 mi★★★★★4.9 Google rating
51 Pleasant St, Malden, MA 02148
- Alberto's Pro. Painting&Reno Inc.Serves Winchester · 3.2 mi★★★★★4.7 Google rating
21 Cummings Park Dr, Woburn, MA 01801
- RB Painting Company, LLCServes Winchester · 4.3 mi★★★★★4.7 Google rating
225R Cedar St, Somerville, MA 02145
- MONTEIRO’S PRECISE PAINTING LLCServes Winchester · 1.9 mi★★★★★4.6 Google rating
2 Glenwood Ave, Woburn, MA 01801
- Restoration ServicesServes Winchester · 2.6 mi★★★★★4.5 Google rating
9 Mystic St, Arlington, MA 02474
- Morse ConstructionsServes Winchester · 3.0 mi★★★★☆4.4 Google rating
3 Arrow Dr, Woburn, MA 01801
- Homer ContractingServes Winchester · 2.8 mi★★★★☆4.2 Google rating
195 Broadway, Arlington, MA 02474
- S+H ConstructionServes Winchester · 4.0 mi★★★★☆4.1 Google rating
45 Brighton St, Belmont, MA 02478
- Cardarelli ContractingServes Winchester · 2.5 mi★★★★☆4.0 Google rating
10 Wheeler Rd, Lexington, MA 02420
- United RER Corp.Serves Winchester · 3.3 mi★★★☆☆3.1 Google rating
53 Washington St, Medford, MA 02155
Painting in Winchester — what to know
Rebates & incentives
Painting is not an energy measure, so there is no Mass Save rebate for it, and Eversource territory does not change that. The dominant rule is lead. Under the federal EPA RRP rule, any contractor disturbing paint in a pre-1978 home must be a certified Lead-Safe Renovator and follow containment and cleanup steps. With Winchester's median home age around 73 years, almost every house predates 1978, so lead-safe work is the default on nearly every job.
The Massachusetts Lead Law adds deleading obligations for pre-1978 homes with a child under 6, and full deleading must be done by a state-licensed deleader, not a painter. Painting carries no rebate to offset the cost, so budget for the full project.
Permits in Winchester
Painting itself rarely needs a building permit in Winchester, and the lead rule does the main regulating. Any paint-disturbing work on a pre-1978 home requires EPA RRP certification under federal law and the Massachusetts Lead Law. Contractors doing remodel-related repaints must hold Massachusetts Home Improvement Contractor (HIC) registration. Winchester does not run a citywide historic color-review district, so exterior color is generally the homeowner's call, though the scale and detail of the town's larger homes make a careful contractor worth the premium. The Winchester Building Department handles any structural carpentry bundled with a larger exterior job.
Typical project cost
Winchester sits near the top of the inner-suburban band, reflecting affluent demand and the prep that large, detailed older homes require. A whole-house interior repaint typically runs $5,000–$13,000 depending on size and plaster work. An exterior repaint on a single-family lands around $8,000–$16,000, and large Colonials, Tudors, and Victorians with intricate trim push higher. Per-room interiors run roughly $450–$900. Lead-safe RRP containment on pre-1978 homes adds cost, and full deleading by a licensed deleader is a separate, larger expense.
About Winchester homes
Winchester has about 22,809 residents across roughly 8,201 housing units in Middlesex County, and the median home was built around 1953. The town is known for substantial older houses: pre-war Colonials, Tudors, and Victorians near the center and the lakes, plus stately homes along the tree-lined streets off Church Street and the Parkway.
That older, detailed stock drives the work. Interior repaints with significant plaster repair, exterior repaints on large wood-clad homes with intricate trim, and cabinet refinishing are the steady jobs here. With a median home age past 70 years, nearly every property predates 1978, so lead-safe handling is assumed on the great majority of projects.
Common questions — Painting in Winchester
- Does my Winchester painter need to be lead-safe certified?
- Almost certainly. With Winchester's median home age past 70 years, nearly every house predates 1978, so the federal EPA RRP rule requires a certified Lead-Safe Renovator for any paint-disturbing work. Ask to see the RRP certification.
- Why does my large Winchester home cost more to paint?
- Big Colonials, Tudors, and Victorians with intricate trim and significant plaster repair take more labor and careful prep. That extra work, plus lead-safe handling on pre-1978 stock, is what drives Winchester's higher end of the range.
- Is there a rebate for painting in Winchester?
- No. Painting is not an energy measure, so unlike HVAC or insulation it carries no Mass Save or utility rebate, even though Winchester is Eversource territory. Budget for the full project cost.
- Why do my plaster walls need so much prep?
- Winchester's older homes mostly have lath-and-plaster walls that crack and lose surface with age. Skim-coating and plaster repair before paint is common here and separates a cheap quote from a finish that holds up.
- What if my home has lead paint and a child under 6?
- The Massachusetts Lead Law requires deleading of pre-1978 homes where a child under 6 lives, and full deleading must be done by a state-licensed deleader, not a painter. A repaint alone does not satisfy the law.
