Heating & Cooling Services in Winter Park, FL

Do you service Winter Park, FL?

Yes. Chilly Billy Heating & Cooling serves Winter Park, FL (ZIP codes 32789, 32792) in Orange County from our shop at 807 Sawdust Trail in Kissimmee. Same-day service is available when scheduling and parts allow.

Heating and cooling services in Winter Park

• AC repair in Winter Park — warm air, short cycling, water leaks, breakdowns
• AC installation and replacement in Winter Park — free estimate with Manual J sizing
• AC maintenance in Winter Park — tune-ups and the Family Comfort Plan
• Ductless mini-splits in Winter Park — garages, lanais, and additions
• Heating repair in Winter Park — heat pumps, heat strips, and furnaces
• Heating installation and replacement in Winter Park
• Heating maintenance in Winter Park — fall tune-ups before cold snaps
• Duct cleaning in Winter Park — musty smells and dust
• Duct repair in Winter Park — leaking or disconnected ductwork
• Duct installation in Winter Park — Manual D design for rooms that never cool
• Attic insulation in Winter Park — cut afternoon heat gain

Common AC and heating problems we fix in Winter Park

• AC blowing warm air or not cooling — low refrigerant, a failing compressor, or a dirty condenser coil in Winter Park's heat.
• Short cycling or a system that won't start — a thermostat, capacitor, or control-board fault we diagnose before quoting.
• Musty smells, uneven rooms, or dust with the AC running — usually leaking or dirty ductwork, an undersized return, or thin attic insulation.
• A system past its life or failing every season — a free replacement estimate with a Manual J load calculation, plus a free second opinion on another company's quote.
• No heat on a cold Central Florida night — heat-pump and furnace repair for the handful of nights a year it matters.

What to expect when you book service in Winter Park

A repair visit starts with an $89 diagnostic ($0 for Family Comfort Plan members). We find the actual cause, explain it in plain language, and give you a written price before any work begins — options without pressure. Same-day service is available when scheduling and parts allow.

For a replacement we measure the load with a Manual J calculation instead of matching the old nameplate, and every Orange County install is permitted and inspected. You get the closed permit for your records, and the work is backed by our written warranty.

Serving Winter Park from our Kissimmee shop

Winter Park is in Orange County, directly north of Osceola County and our Kissimmee shop. Replacement work is permitted and inspected like any other install; we pull the permit and schedule the inspection.

Pricing, warranties, and plans for Winter Park homeowners

• Repair visits start with an $89 diagnostic, $0 for Family Comfort Plan members. You approve a written price before any work.
• Complete-system replacement estimates are free and include a Manual J load calculation. A second opinion on another company's quote is free.
• Repairs are warrantied for one year on parts and one year on labor for systems ten years old or newer, and one year on parts with six months on labor for older systems. Installs carry a one-year base labor warranty, with extended options up to fifteen years.
• The Family Comfort Plan is $199 a year or $16.59 a month: two tune-ups a year, 10% off repairs, 5% off installs, and priority scheduling, with no auto-renew.
• We install Rheem, Goodman, and Trane and service every brand, working under Florida license CAC1821877. Financing is available through GoodLeap.

Nearby communities we serve from Winter Park

Homeowners in Eatonville, Goldenrod, Maitland are scheduled through our Winter Park route. Call and we will confirm the day's availability.

Other Orange County communities we serve

Meadow Woods, Lake Nona, Hunters Creek, Orlando, Dr. Phillips, MetroWest, College Park, Conway, Baldwin Park, Windermere, Horizons West, Winter Garden.