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Exterior Remodeling · Winter Park, FL

Exterior Remodeling in Winter Park, FL

Exterior remodeling in Winter Park — siding, stucco, painting, windows and gutters that boost curb appeal and stand up to Florida weather.

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

Free Exterior Remodeling Estimate

We typically reply the same business day.

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

Exterior remodeling in Winter Park, FL: Right Image Inc (Right Image Builders) is a licensed and insured Florida general contractor (CGC1539321) based in Oviedo, handling siding, stucco repair, fascia and soffit, exterior painting, windows and gutters across Winter Park and Orange County — the cause fixed before the finish goes on, under one contract.

Exterior Remodeling in Winter Park, FL — planning ranges (updated October 2026): Exterior painting $4,000 – $12,000 · Stucco repair & refinish $5,000 – $20,000 · Window replacement $500 – $1,200 / window. Permits run through City of Winter Park Building Division. Ranges are planning figures, not a quote — every project is priced after a site visit.

Key facts

Exterior Remodeling in Winter Park at a glance

Planning range
Exterior painting $4,000 – $12,000; Stucco repair & refinish $5,000 – $20,000; Window replacement $500 – $1,200 / window (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 Park Building Division. Winter Park issues its own permits; some areas carry historic-district 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.

Curb appeal that also protects the house

The exterior is your home's weather barrier as much as its first impression. Cracked stucco, tired paint, and failing seals let Florida humidity in — so exterior work is about protection, not just looks.

We handle siding, stucco repair and refinishing, exterior painting, window replacement, and gutters for Winter Park homes, coordinated as one project so the finishes and the envelope work together.

Exterior Remodeling · Winter Park

What we handle on an exterior remodel in Winter Park

01

Siding & stucco

Repair or replace siding and stucco, seal cracks, and refinish so the surface sheds water instead of trapping it.

Stucco repair & refinishing: planning range, permits and the cities we cover →

Siding replacement and repair: fiber-cement, vinyl and wood, fascia and soffit →

02

Exterior painting

Proper prep, patching and premium coatings that hold up to Central Florida sun and rain.

03

Windows & doors

Replace aging or leaking windows and exterior doors for better sealing, efficiency and storm performance.

04

Gutters & trim

Gutters, fascia and soffit that move water away from the foundation and finish the roofline cleanly.

Winter Park, Orange County

What an exterior remodel in Winter Park involves

We work throughout Winter Park — from Windsong and Winter Park Pines to Orwin Manor, Olde Winter Park, Kenilworth Shores. Winter Park is an affluent, tree-lined Orange County city known for brick streets and lakefront homes, and it sits in Orange County, part of the Greater Orlando area we cover from our base in Oviedo.

Permitting for a Winter Park exterior remodel goes through City of Winter Park Building Division. Parts of Winter Park 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 Park, we regularly take on work in nearby communities including Maitland, Baldwin Park, Altamonte Springs and Orlando.

Every Winter Park exterior remodel 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 Windsong or Winter Park Pines through final inspection with City of Winter Park Building Division.

Winter Park housing

What we see in Winter Park homes

Winter Park is known for brick streets, lakefront lots and 1920s–1950s homes around Park Avenue, Rollins and Olde Winter Park, many under historic or neighborhood design review, alongside 1960s Winter Park Pines and newer Windsong. The city’s permitting and tree rules are stricter than most of its neighbors’. For exterior work, it means dealing with stucco cracks, wood rot at fascia and trim, and failed sealants before paint goes on.

Winter Park

Home exterior contractor in Winter Park: siding, fascia, stucco and paint

Winter Park's 1920s–50s homes around Park Avenue, Rollins and Olde Winter Park are wood-sided with wood fascia, soffit and trim under old tree canopy, so rot repair, re-siding and repainting are the common projects, with historic or neighborhood design review for street-facing changes; 1960s Winter Park Pines and newer Windsong are block-and-stucco homes where the work is stucco repair, fascia replacement and repainting. The city's permitting and tree rules are stricter than most of its neighbors'.

Window replacement, full re-siding and structural repairs are permitted through the City of Winter Park Building Division; painting and cosmetic patching usually are not.

Siding replacement & repair →

Timeline

How an exterior project runs in Winter Park

We do not publish a standard duration for exterior work — the size of the house, the amount of repair under the finish and the weather set it — so the written schedule you get with the estimate carries the dates. The stages are the same everywhere.

  1. Site visit — we walk the envelope: fascia, soffit and trim for rot, stucco for cracks and hollow spots, sealant at windows and bands, siding for water behind it, gutters and drainage.
  2. Scope and selections — which boards and walls are repaired or replaced, siding or stucco finish, window and door products with their Florida Product Approval, colours.
  3. HOA or design review — colours, materials and window styles submitted where your community or a historic district reviews them.
  4. Permit — filed with City of Winter Park Building Division for window and door replacement, full re-siding and structural repairs; painting and cosmetic patching usually need none.
  5. Repairs — rot cut out and replaced, flashing at the transitions, stucco causes fixed and the wall patched or re-coated with the texture matched.
  6. Windows, siding and trim — installed, flashed and sealed.
  7. Paint and close-out — prep, patching and coating, gutters and downspouts, any inspection called and the permit closed, then a walkthrough.
At a Glance

Exterior Remodeling in Winter Park — the local details

City
Winter Park, FL
County
Orange County
Permit authority
City of Winter Park Building Division
Jurisdiction note
Winter Park issues its own permits; some areas carry historic-district review.
Neighborhoods served
Windsong, Winter Park Pines, Orwin Manor, Olde Winter Park, Kenilworth Shores
Contractor license
CGC1539321 — licensed & insured Florida general contractor
Local Knowledge

Exterior Remodeling in Winter Park

Winter Park is an affluent, tree-lined Orange County city known for brick streets and lakefront homes. We cover all of Winter Park — Windsong, Winter Park Pines, Orwin Manor, Olde Winter Park, Kenilworth Shores — and the surrounding Orange County area, with plans filed through City of Winter Park Building Division.

Neighborhoods we serve in Winter Park

Windsong Winter Park Pines Orwin Manor Olde Winter Park Kenilworth Shores

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

Permits in Winter Park

Permit authority: City of Winter Park Building Division

Winter Park issues its own permits; some areas carry historic-district review. We pull the permits and manage the inspections as part of your project.

County: Orange County

Examples

Exterior Remodeling — finish & layout examples

Finish and layout examples for exterior remodeling. Photos of completed projects are being added.

Exterior remodel with fresh stucco, updated trim and new windows — Exterior Remodeling example
Refreshed home exterior with new paint, roofline detail and updated entry — Exterior Remodeling example
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

Exterior Remodeling in Winter Park: what it typically costs

Typical planning ranges for Winter Park exterior work. Planning ranges only, not a quote — final pricing depends on size, material and condition.

ProjectTypical rangeNotes
Exterior painting$4,000 – $12,000Prep, patching, premium coating; home size dependent
Stucco repair & refinish$5,000 – $20,000Crack repair, re-coat, texture match
Window replacement$500 – $1,200 / windowImpact vs. standard, size and count

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 Park Building Division are separate and vary by scope, and we itemise them for your Winter Park estimate rather than burying them in a lump sum.

What moves the price of exterior work

  • How much repair sits under the finish — rotten fascia, soffit and sheathing, stucco that must be cut back to the cause.
  • Wall area and height — a two-story house, gables and bands add surface and access.
  • Material — fiber-cement, vinyl or matched wood siding; re-coat versus full re-stucco.
  • Windows and doors — standard or impact-rated units, size and count, each with its product approval.
  • Coating — the number of colours, trim detail and the prep the surface needs.
  • Permits, HOA submittals and inspections — shown separately on the estimate.

Stucco repair & refinishing →

Plan it

Plan your project

Get In Touch

Refresh your Winter Park home's exterior

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

Exterior Remodeling FAQ

Common questions

Roughly every 5–10 years depending on sun exposure, color, and prep. Good surface prep and a quality coating make the difference between a paint job that lasts and one that fades and peels early.
Yes — matching texture and finish is part of doing stucco repair right, so patches blend instead of standing out. We repair the underlying cause of cracking too, not just the surface.
Impact windows improve storm protection, sealing, and often insurance posture, at a higher cost than standard replacements. We'll lay out the trade-offs for your home and budget.
Yes — siding, stucco, paint, windows and gutters can be coordinated together so the envelope and the finishes are done in the right order by one team. We do this work across Winter Park and the wider Orange County area from our base in Oviedo.
Exterior Remodeling in Winter Park, FL — planning ranges (updated October 2026): Exterior painting $4,000 – $12,000 · Stucco repair & refinish $5,000 – $20,000 · Window replacement $500 – $1,200 / window. Ranges are planning figures, not a quote — every project is priced after a site visit. Permit and inspection fees charged by City of Winter Park Building Division are separate and itemised in your Winter Park estimate.
We don't publish a standard duration for exterior remodel work — it depends on the scope, the materials and, where a permit is needed, the review time at City of Winter Park Building Division. You get a written schedule with your estimate.
Every exterior remodel we take on in Winter Park 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 Park 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 Park and Orange County from our base in Oviedo. Call (407) 993-6889 or request a free estimate.
City of Winter Park Building Division. Winter Park issues its own permits; some areas carry historic-district review. We handle the permitting for your project either way.
All of it — including Windsong, Winter Park Pines, Orwin Manor, Olde Winter Park, Kenilworth Shores — 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.
Nearby

Exterior remodeling nearby

Exterior Remodeling pages for the communities around Winter Park, each with the same planning ranges and its own permit office.

More in Winter Park

Other services we provide in Winter Park

Refresh your Winter Park home's exterior

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