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Roofing · Winter Garden, FL

Roofing in Winter Garden, FL

Roof repairs and full replacements in Winter Garden — shingle, tile and metal — built for Florida sun, storms and insurance requirements.

Licensed & insured · Lic. #CGC1539321
By Vladimir Svirsky, President · Updated
Local permits & inspections handled
Written estimate, no obligation
Serving Winter Garden from Oviedo

Free Roofing Estimate

We typically reply the same business day.

✔ Lic. #CGC1539321
✔ Permits & inspections handled
✔ 433+ projects completed
★ 5.0★ on Google (7 reviews)
✔ Licensed & Insured

Right Image Inc (Right Image Builders) is a licensed and insured Florida general contractor (CGC1539321) in Oviedo, handling roof repair and replacement across Winter Garden and Orange County. Shingle, tile and metal — plus leak repair, storm damage, and the interior restoration most roofers won't touch.

Roofing in Winter Garden, FL — planning ranges (updated October 2026): Roof repair $500 – $3,500 · Shingle replacement $9,000 – $20,000 · Tile or metal replacement $20,000 – $45,000+. Permits run through City of Winter Garden Building Division. Ranges are planning figures, not a quote — every project is priced after a site visit.

Key facts

Roofing in Winter Garden at a glance

Planning range
Roof repair $500 – $3,500; Shingle replacement $9,000 – $20,000; Tile or metal replacement $20,000 – $45,000+ (updated October 2026; not a quote)
Typical time
Set in your written schedule: it depends on the scope, the materials and the permit review.
Permits
City of Winter Garden Building Division. Winter Garden issues its own permits; the historic downtown has added review.
Wind and flood
Outside the High-Velocity Hurricane Zone (Broward and Miami-Dade only); wind design is set per address. Check the flood zone on the FEMA flood map. More in the codes and flood FAQ.
Licence and reviews
Florida certified general contractor CGC1539321 (DBPR: current, active, expires 08/31/2028) · 5.0★ on Google (7 reviews, Oct 2026)
Next step
Free written estimate: call (407) 993-6889 or use the form on this page. Planning help: guides and FAQ.

A roof built for Florida — and the team that fixes what a leak damages

Central Florida roofs take sun, heat, and heavy summer storms. Whether you need a targeted repair or a full replacement, we install for the climate and document the work for your insurer.

Because we're a full general contractor, we don't stop at the shingles: when a leak has damaged drywall, insulation, or trim inside your Winter Garden home, we can restore the interior under the same contract.

Roofing · Winter Garden

What we handle on a roof in Winter Garden

01

Full roof replacement

Complete tear-off and re-roof in shingle, tile or metal, with code-compliant underlayment and proper flashing.

02

Repairs & leaks

Leak tracing, shingle and tile repair, flashing, and fascia/soffit fixes before water reaches the interior.

03

Storm & insurance

Storm-damage assessment and documentation to support your insurance claim, done straight and by the book.

04

Roof + interior restoration

Repair the roof and restore the water-damaged drywall, insulation and paint inside — under one contract.

Winter Garden, Orange County

What a roof in Winter Garden involves

We work throughout Winter Garden — from Historic Downtown Winter Garden and Stoneybrook West to Orchard Hills, Independence, Hamlin. Winter Garden is a west Orange County city with a revitalized brick downtown and Horizon West growth, and it sits in Orange County, part of the Greater Orlando area we cover from our base in Oviedo.

Permitting for a Winter Garden roof goes through City of Winter Garden Building Division. Parts of Winter Garden carry historic-district review, so anything that changes the look of the house from the street can need an extra approval before a permit is issued. We build that step into the schedule rather than discovering it late.

Alongside Winter Garden, we regularly take on work in nearby communities including Ocoee, Windermere, Apopka and Orlando.

Every Winter Garden roof we take on is run by the same licensed general contractor (CGC1539321) that pulls the permit — so there is one point of accountability from the first walkthrough in Historic Downtown Winter Garden or Stoneybrook West through final inspection with City of Winter Garden Building Division.

Winter Garden housing

What we see in Winter Garden homes

Winter Garden pairs a revitalized brick downtown of 1920s–50s homes (with historic-district review) with 2000s communities like Stoneybrook West and Orchard Hills and the fast-growing Horizon West area — Hamlin, Independence — where many addresses are unincorporated Orange County rather than city. For roofs, it means knowing the roof’s age, the deck and the local wind-mitigation details before we quote a repair or a replacement.

At a Glance

Roofing in Winter Garden — the local details

City
Winter Garden, FL
County
Orange County
Permit authority
City of Winter Garden Building Division
Jurisdiction note
Winter Garden issues its own permits; the historic downtown has added review.
Neighborhoods served
Historic Downtown Winter Garden, Stoneybrook West, Orchard Hills, Independence, Hamlin
Contractor license
CGC1539321 — licensed & insured Florida general contractor
Local Knowledge

Roofing in Winter Garden

Winter Garden is a west Orange County city with a revitalized brick downtown and Horizon West growth. We cover all of Winter Garden — Historic Downtown Winter Garden, Stoneybrook West, Orchard Hills, Independence, Hamlin — and the surrounding Orange County area, with plans filed through City of Winter Garden Building Division.

Neighborhoods we serve in Winter Garden

Historic Downtown Winter Garden Stoneybrook West Orchard Hills Independence Hamlin

Serving all of Winter Garden and the surrounding Orange County area.

Permits in Winter Garden

Permit authority: City of Winter Garden Building Division

Winter Garden issues its own permits; the historic downtown has added review. We pull the permits and manage the inspections as part of your project.

County: Orange County

Our Work

Roofing projects

A sample of roofing work by our team.

Completed architectural shingle roof replacement on a single-storey home, shot from the ridge — Roofing by Right Image Builders
New shingle roof with hip and ridge caps finished over a rear addition — Roofing by Right Image Builders
Roof replacement in progress showing fresh underlayment and shingle courses — Roofing by Right Image Builders
Finished residential re-roof with new flashing and vent boots — Roofing by Right Image Builders
Completed white TPO membrane roof on a commercial building — Roofing by Right Image Builders
Google reviews

5.0★ on Google · 7 reviews

Quoted word for word from our Google Business Profile (Oct 2026). Reviewers name the work; we add nothing.

★★★★★
Thank you, Right Image Inc., for our new roof, stucco, and bathroom remodel! Our home looks refreshed, and we’re very happy with the results. Vladimir and his team were helpful throughout the project and took care of the details. We appreciate your hard work and highly recommend your services!
Elcira S. — Google review, Oct 2026 · new roof, stucco & bathroom remodel
★★★★★

Right Image Inc. built my ADU and installed a new roof, and I’m very pleased with how everything turned out. Vladimir and his team were easy to work with, answered my questions, and paid attention to the details. Thank you for helping bring this project to life!

Antonio R. · Google, Oct 2026 · ADU & new roof
★★★★★

Excellent service at a reasonable price! They repaired a roof leak around a pipe vent, and I’m very happy with the work. I appreciate their help and would highly recommend them to anyone needing a roof repair.

Victor · Google, Oct 2026 · roof leak repair
Planning Ranges

Roofing in Winter Garden: what it typically costs

Typical planning ranges for Winter Garden roofing. Planning ranges only, not a quote — final pricing depends on size, pitch and material.

ProjectTypical rangeNotes
Roof repair$500 – $3,500Leaks, flashing, shingle/tile patch
Shingle replacement$9,000 – $20,000Architectural shingle, full tear-off
Tile or metal replacement$20,000 – $45,000+Material and structure dependent

These are typical planning ranges — not a quote. Every project is priced after we see the space. Permit and inspection fees charged by City of Winter Garden Building Division are separate and vary by scope, and we itemise them for your Winter Garden estimate rather than burying them in a lump sum.

Plan it

Plan your project

Get In Touch

Get your Winter Garden roof handled

Call (407) 993-6889 or send your project details — we’ll get right back to you.

Roofing FAQ

Common questions

It depends on the roof's age, the extent of damage, and whether leaks are isolated or widespread. If the roof is near the end of its life or damage is spread out, replacement is usually the better value. We'll give you an honest assessment either way.
Yes. We assess the damage, document it thoroughly, and give you what you need for your claim. We do it straight — we won't fabricate damage or push a claim that isn't there.
Architectural shingle, tile, and metal. Each has trade-offs in cost, lifespan and look for Central Florida homes, and we'll walk you through what fits your house and budget.
Yes. Unlike a roofing-only company, we can repair the roof and restore the drywall, insulation, and paint the leak damaged inside, all under one contract. We do this work across Winter Garden and the wider Orange County area from our base in Oviedo.
Roofing in Winter Garden, FL — planning ranges (updated October 2026): Roof repair $500 – $3,500 · Shingle replacement $9,000 – $20,000 · Tile or metal replacement $20,000 – $45,000+. Ranges are planning figures, not a quote — every project is priced after a site visit. Permit and inspection fees charged by City of Winter Garden Building Division are separate and itemised in your Winter Garden estimate.
We don't publish a standard duration for roof repair or replacement work — it depends on the scope, the materials and, where a permit is needed, the review time at City of Winter Garden Building Division. You get a written schedule with your estimate.
Every roof repair or replacement we take on in Winter Garden is run by Vladimir Svirsky, president of Right Image Inc, under Florida certified general contractor licence CGC1539321 — the same licence that pulls the permit with City of Winter Garden Building Division and schedules the inspections — so there is one point of accountability from the first walkthrough to the final inspection. You can verify licence CGC1539321 on the Florida Department of Business & Professional Regulation (DBPR) licence search.
Yes — Right Image Builders serves all of Winter Garden and Orange County from our base in Oviedo. Call (407) 993-6889 or request a free estimate.
City of Winter Garden Building Division. Winter Garden issues its own permits; the historic downtown has added review. We handle the permitting for your project either way.
All of it — including Historic Downtown Winter Garden, Stoneybrook West, Orchard Hills, Independence, Hamlin — plus the surrounding Orange County area. If you're not sure whether your street is inside the city limits, tell us the address and we'll confirm which building department reviews the work.
More in Winter Garden

Other services we provide in Winter Garden

Get your Winter Garden roof handled

(407) 993-6889
Call (407) 993-6889 — Free Estimate