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Additions & ADUs · Winter Park, FL

Home Additions in Winter Park, FL

Room additions, second stories, in-law suites and ADUs in Winter Park — engineered, permitted and built from foundation to finish by one licensed team.

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

Free Additions & ADUs Estimate

We typically reply the same business day.

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

Home additions in Winter Park, FL: Right Image Inc (Right Image Builders) is a licensed and insured Florida general contractor (CGC1539321) based in Oviedo, building room additions, second stories, in-law suites, garage conversions and ADUs across Winter Park and Orange County — structural engineering, permitting and construction under one contract.

Additions & ADUs in Winter Park, FL — planning ranges (updated October 2026): Room addition $40,000 – $120,000 · Second-story addition $150,000 – $300,000+ · ADU / garage conversion $50,000 – $180,000. Typical time: about 3–5 months from permit to finish for a room addition; second stories and ADUs take longer. 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

Additions & ADUs in Winter Park at a glance

Planning range
Room addition $40,000 – $120,000; Second-story addition $150,000 – $300,000+; ADU / garage conversion $50,000 – $180,000 (updated October 2026; not a quote)
Typical time
about 3–5 months from permit to finish for a room addition; second stories and ADUs take longer
Permits
City of Winter Park Building Division. Winter Park issues its own permits; some areas carry historic-district review.
ADUs
Guesthouse only — not a rentable ADU — City of Winter Park ADU rules
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.

More space, matched to your home and your local code

Adding on is the most structural work a home can undergo — foundation, framing, roofline, and tie-ins all have to be engineered and permitted correctly. We manage the whole process, from feasibility and design through permits and final finishes.

Additions and accessory dwelling units (ADUs) are handled differently by each jurisdiction — the rules change between each city and the unincorporated parts of Seminole, Orange and Osceola counties. We build to what actually applies to your Winter Park lot.

Additions & ADUs · Winter Park

What we handle on a home addition in Winter Park

01

Room & primary-suite additions

Add a bedroom, primary suite, or great-room bump-out with a foundation and roofline that match the existing home.

Mother-in-law suites: attached suites for multigenerational living →

02

Second-story additions

Build up when you can't build out — engineered for the existing structure and Florida wind loads.

Second-story additions: engineering, timeline and planning range →

03

ADUs & in-law suites

Detached or attached accessory units and garage conversions for multigenerational living or a home office, built to local code.

ADU builder: rules by city, planning range and permits →

Garage conversions: permits, parking and what it takes to make a garage livable →

04

Engineering & permits

We coordinate the structural engineering, permitting, and any HOA/ARB review so the addition is legal and lasting.

Winter Park, Orange County

What a home addition 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 home addition 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 home addition 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 additions and ADUs, it means confirming the zoning, setbacks and any HOA or architectural review for your specific lot before design starts.

Winter Park

Can you build an ADU in Winter Park?

Winter Park doesn't allow a rentable ADU. Guesthouses and garage apartments of up to 1,000 sq ft are permitted only to house guests, domestic staff or family members of the main house, with no kitchen or cooking facilities, no separate utility meters and no rental of any kind, and they can't be occupied before the main house is finished.

Source: Winter Park Code Sec. 58-71(h)(10), as renumbered by Ord. 3295-24 (2024), City of Winter Park (checked October 2026). Rules change, and HOA covenants can be stricter than the code; we confirm both for your parcel before design.

ADU rules by city (2026) →

Timeline

How long a home addition takes in Winter Park, stage by stage

Typical time: about 3–5 months from permit to finish for a room addition; second stories and ADUs take longer. The stages are the same for every addition we build across Greater Orlando; what changes is the size of the job and the review time at your building department.

  1. Site visit and feasibility — we measure, check the slab, roof, electrical panel and plumbing, and confirm the zoning setbacks and any HOA or architectural review for your lot.
  2. Design — a floor plan and elevations matched to the house, then a written, itemised estimate.
  3. Structural engineering — sealed drawings for the foundation, the roof tie-in and the wind design for your address, plus energy calculations.
  4. Permit review — the set goes to City of Winter Park Building Division; we answer any review comments, and the written schedule you get with the estimate builds in that turnaround.
  5. Construction — foundation, framing, the roof tie-in and dry-in, then the trades, insulation, drywall and finishes.
  6. Inspections and close-out — every inspection scheduled by us, the permit closed, and a final walkthrough with you.
At a Glance

Additions & ADUs 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

Additions & ADUs 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

Additions & ADUs — finish & layout examples

Finish and layout examples for additions & ADUs. Photos of completed projects are being added.

Detached accessory dwelling unit with stucco and cedar siding, its own entry and a paved walkway — Additions & ADUs example
Garage converted into finished living space with a new entry door and windows — Additions & ADUs 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.

★★★★★
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 review, Oct 2026 · ADU & new roof
★★★★★

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, Oct 2026 · new roof, stucco & bathroom remodel
★★★★★

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

Additions & ADUs in Winter Park: what it typically costs

Typical planning ranges for a Winter Park addition or ADU. Planning ranges only, not a quote — final pricing depends on size, foundation and site.

ProjectTypical rangeNotes
Room addition$40,000 – $120,000Size, foundation, finishes
Second-story addition$150,000 – $300,000+Structural reinforcement, new stair, roof
ADU / garage conversion$50,000 – $180,000Detached vs. conversion, utilities, kitchen/bath

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 a home addition

  • Square footage and layout — the number of rooms, closets and doors.
  • Foundation and site — slab-on-grade or raised floor, soil, drainage and whether the lot is in a mapped flood zone.
  • The roof tie-in — matching tile or shingle, and whether part of the existing roof is redone so the two match.
  • Plumbing — a bathroom or kitchenette adds the most, and septic capacity matters on homes that are not on sewer.
  • Finishes, windows and doors — rated for the design wind pressure at your address, matched to the house or upgraded.

Room addition cost guide (2026) →

Plan it

Addition & ADU guides

Get In Touch

Plan your Winter Park addition or ADU

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

Additions & ADUs FAQ

Common questions

It depends on your city or county's zoning, lot size, and setbacks — the rules differ from one jurisdiction to the next across Seminole, Orange and Osceola counties. We check what applies to your specific lot before you spend money on design.
Most room additions run about 3–5 months from permit to finish; second stories and ADUs take longer. Engineering and permitting happen before we break ground, and we give you a schedule up front. In Winter Park, permit review goes through City of Winter Park Building Division, and we build their turnaround into the schedule we give you.
Yes — additions require structural engineering and permitting, and we coordinate both, plus any HOA or architectural-review approval, as part of the project. In Winter Park, that review goes through City of Winter Park Building Division.
An addition expands your existing home; an ADU is a separate living unit with its own kitchen and bath, whether detached or a garage conversion. They're permitted differently — we'll explain which fits your goal. We do this work across Winter Park and the wider Orange County area from our base in Oviedo.
Additions & ADUs in Winter Park, FL — planning ranges (updated October 2026): Room addition $40,000 – $120,000 · Second-story addition $150,000 – $300,000+ · ADU / garage conversion $50,000 – $180,000. Ranges are planning figures, not a quote — every project is priced after a site visit. Permit and inspection fees charged by City of Winter Park Building Division are separate and itemised in your Winter Park estimate.
Every home addition or ADU 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.
Not as a rentable unit. Winter Park permits guesthouses and garage apartments of up to 1,000 sq ft for guests, domestic staff or family members only — no kitchen, no separate utility meters and no rental. An attached in-law suite permitted as a room addition is the usual way to house family. Source: Winter Park Code Sec. 58-71(h)(10), as renumbered by Ord. 3295-24 (2024), City of Winter Park (checked October 2026). We confirm the rules for your parcel before design.
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

Home additions nearby

Additions & ADUs 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

Talk through your Winter Park addition with us

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