Another homeowner here with a positive experience: we used Karoly Windows & Doors to replace 10 windows in our 1955 home in Pinellas Park. I was impressed at how detail-oriented they were – we have a mid-century style front window with a horizontal divided-light design, and they sourced a new window that replicated that pattern exactly so our home's character didn't change. Their team was on schedule every day (even finished a day early) and very courteous. They took care to protect our hardwood floors and cleaned up each afternoon.
Also, they handled the permit process seamlessly; the inspector told us it was nice to see a thorough job with all the proper documents in order. We felt well taken care of, and the new windows are fantastic. Just wanted to drop that recommendation since finding a good contractor can be daunting.
I love how my house feels after window replacements, but one unexpected thing: our old windows had these wood-framed screens that we rarely used (they were warped and stored in the shed). The new windows (we got vinyl double-hungs for our 1930 bungalow in Old Seminole Heights) came with nice, tight-fitting screens, so now we can actually open up the house on cooler days. The cross-breeze is amazing, and no bugs!
It's funny because we Floridians use A/C so much, but having operable windows that actually work and have screens has let us enjoy the cool mornings in winter. Just remember to ask about screens if it's important to you – some window models or installers treat them as add-ons. Ours were included, but a friend of mine had to pay extra for screens on her new windows, which she didn't realize until later.
I'll be the one to say not all window replacement stories are perfect. My experience with a contractor in 2020 for my 1964 house in Town 'n' Country (Tampa) was pretty frustrating. The sales process was smooth but once I signed, the communication went downhill. The windows themselves are good quality, but the install crew was overbooked and rushed. They ended up cracking some of the interior plaster around one window and didn't tell me; I found the damage later. They also left a huge mess of old nails and broken glass in my flower beds outside 😠.
I had to chase them to come back and fix the plaster. After that, I learned to read reviews more carefully and not just go with the lowest bid. The project eventually got done and the windows are fine now, but I wish I'd chosen a company known for better care and professionalism. So definitely vet your contractors – ask neighbors or look for ones that specialize in older homes. Some crews treat an old house like new construction and that's where things can go wrong.
When replacing windows in an older home, don't forget about the small design choices. I have a 1920s Colonial Revival-style house in Dunedin, and when I ordered new windows, I had the option for external grids (grilles) vs internal grids. To mimic the old look, I went with external grids that sit on the glass surface to give that true divided-light appearance (even though the panes are actually one piece of glass). It cost a bit more, but it really makes a difference aesthetically.
A neighbor with the same model house opted for no grids at all in his replacements. While his windows perform just as well, the house lost a bit of its historic charm with plain glass. So my tip: if your original windows had a pattern (like six-over-six or four-over-one, etc.), see if your replacement windows can incorporate that. Many companies offer colonial-style grids or prairie grids that can closely match the era. It keeps that classic feel alive.
Materials matter too. Our 1950 house in Temple Terrace had its original wood windows until we replaced them. We debated wood vs vinyl vs aluminum replacements. Wood (or wood-clad) looks amazing and can satisfy any historic requirements, but the cost was nearly double and there's maintenance (painting) to consider. Vinyl is low maintenance and a good insulator, but cheap vinyl can warp in Florida heat (make sure to get high-quality if you choose vinyl). Aluminum frames are super sturdy and have thinner profiles (which can look closer to old steel windows), and they hold up to storms well, but they conduct heat, so they can let more heat in unless they have a thermal break.
We ended up with high-quality vinyl windows that have aluminum reinforcement inside for strength. They look great and have held up so far (5 years now) with no warping. So, weigh your priorities: if you absolutely need the wood look and have the budget, go wood. If not, a good vinyl or aluminum window designed for Florida weather can work well.
I'd also suggest getting a few quotes. For my 1967 home in Largo, I got three different quotes and they were all over the place in price and approach. One company (a big national brand) quoted me almost $25k for 12 windows using their own high-end product. Another local contractor quoted $15k for a similar number of windows with a standard product line. And a third (which ended up being Pro Tech Windows & Doors, mentioned earlier by @ericrebel396) came in around $16k and included some structural sill repairs and permitting in that price.
We went with Pro Tech because they weren't the cheapest or the most expensive, but they clearly knew what was needed for an older house. No regrets there. Moral of the story: prices can vary a lot. Make sure each quote is apples-to-apples (same number of windows, type of glass, etc.) and consider the company's knowledge and reputation, not just the bottom line price.
After our window replacement, we decided to dress them up a bit to suit our old house. Our 1930 bungalow in Hyde Park had decorative exterior trim around the windows (those classic Craftsman frames). Some of that got damaged when the old windows came out, but the installers replaced it with new trim that we then painted to match the house. We even added back little wooden sills and apron pieces inside to replicate the old look.
If you value those vintage touches, discuss it with your contractor. Some will just finish off with flat stock trim, which is fine but might look a bit plain on a historic home. In our case we pointed it out beforehand, and they were happy to oblige with nicer trim details for a small extra cost. Now our new windows have that vintage vibe with chunky trim and sills, but all the modern functionality.
One thing I noticed after replacing the windows in my 1946 house in Gulfport: reduced condensation. Our old single panes would get foggy with condensation every winter morning due to the temperature difference (and that can lead to mold or wood damage over time). With the new double-pane insulated glass, I hardly see any condensation at all on the interior. It's great for the health of the house.
Also, the musty humidity smell that used to be near the old windows on rainy days is gone – the new seals keep moisture out. If you have any mold or mildew around your old window frames, address that during replacement. We had a bit of black mold starting on one sill, and the installer properly cleaned and treated it when putting in the new window. I'm breathing easier (literally) now.
Our old home in Plant City (built 1930) has a brick facade, and I was really worried about how window replacement would work without harming the brick. The key is a skilled installer. The crew that did ours managed to remove the old windows carefully and they used new-construction style windows with nailing fins. They had to cut back a little of the interior plaster to fit them, then patched it up. From the outside, they used matching brick-mold trim and caulked it nicely. You can't see any damage to the original brickwork.
If you have masonry (brick or stucco) around your windows, make sure your contractor has experience with that. I've heard horror stories of bricks getting cracked or stucco all busted up. We specifically chose a team that had done a historic brick house down the street (we went and looked at their work beforehand). So maybe ask to see a similar project from whoever you hire.
Jumping in to second what @kathyr27 and @anime800 said about Karoly Windows & Doors. They did my windows in my 1963 home in Apollo Beach and were fantastic. It's a bit of a drive for them to come down to south Hillsborough, but they were still on time each day! Also, they didn't blink at the quirks of my older house (like the not-so-square openings and some hidden water damage in one wall). They just fixed everything up as they went.
The quote was very reasonable given the level of detail – not the cheapest, but far from the most expensive of the bids I got. After seeing their work, two of my neighbors have since used them too with similarly great results. It's nice to have contractors you can confidently recommend.