66/100CR Score
Ranked #1 because of its Google rating and review volume: 5.0★ from 936 Google reviews, the most in Winter Park.
- 5.0★ from 936 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 1983 Spring Ave, Oviedo, FL 32765
Best Gutter Installers in Winter Park, FL (2026)
270 gutter installers ranked by CR ScoreUpdated 0 paid placements in this rankingHow we rank →
The short answer
- 1
Best overall in Winter Park: Prestige Cleaning, CR Score 66/100; 5.0★ from 936 Google reviews; open 24/7.
- 2
Best for emergencies (open 24/7): Gutter Masters of Central Florida, posts 24/7 hours; ranked #2 of 270.
- 21
Most-reviewed: Gutters KLS & Screen Services, 756 Google reviews at 5.0★, the most of 270 ranked after Prestige Cleaning; ranked #21.
Rankings can't be bought. Contractors can't pay to change their rank or score. How we rank
270 Winter Park gutter installers are ranked here by CR Score, from ten published factors. 60 are open 24/7, 185 open Saturdays and 109 open Sundays, based on posted hours. The median Google rating is 5.0★ across 270 rated businesses.
Top 10 gutter installers in Winter Park at a glance
| Rank | Business | CR Score | Google rating | Based in | Hours | Best for |
|---|---|---|---|---|---|---|
| 1 | Prestige Cleaning | 66 | 5.0★ (936) | Oviedo, 9 mi away | 24/7 | Overall |
| 2 | Gutter Masters of Central Florida | 65 | 4.8★ (431) | Orlando, 6 mi away | 24/7 | Emergencies |
| 3 | Proklean Pressure Washing LLC | 64 | 5.0★ (123) | Orlando, 2 mi away | 24/7 | — |
| 4 | Firsthand Lawn and Landscape, LLC | 64 | 5.0★ (136) | Orlando, 5 mi away | 24/7 | — |
| 5 | SplashKingz Exterior Clean | 64 | 5.0★ (99) | Altamonte Springs, 3 mi away | 24/7 | — |
| 6 | Ragin Cajun Soft Wash | 64 | 5.0★ (356) | Longwood, 6 mi away | Sat · Sun · Evenings | — |
| 7 | Edy Pressure and Soft-Wash | 64 | 5.0★ (246) | Belle Isle, 10 mi away | 24/7 | — |
| 8 | Powerhouse Window Cleaning & Pressure Washing | 64 | 5.0★ (373) | Orlando, 7 mi away | Sat · Sun · Evenings | — |
| 9 | Aqua Bins Exterior Cleaning Services | 63 | 5.0★ (654) | Belle Isle, 13 mi away | 24/7 | — |
| 10 | Eddie's Pressure Washing LLC | 63 | 5.0★ (315) | DeBary, 8 mi away | 24/7 | — |
The 270 best gutter installers in Winter Park, ranked
Ordered by CR Score, a 0–100 score from ten published factors. Paid placement never changes the order.
Scores below: based on 8 of 10 factors; credentials and recency not yet collected. Hatched segments mark factors we don't have yet.
Based in Orlando, 6 mi away
65/100CR ScoreRanked #2 because of its Google rating and trade focus: 4.8★ from 431 Google reviews, listed on Google as “Gutter cleaning service”.
- 4.8★ from 431 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 4455 Dardanelle Dr Suite D, Orlando, FL 32808
Based in Orlando, 2 mi away
64/100CR ScoreRanked #3 because of its Google rating and trade focus: 5.0★ from 123 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 123 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 5580 Century 21 Blvd apt 120, Orlando, FL 32807
Based in Orlando, 5 mi away
64/100CR ScoreRanked #4 because of its Google rating and trade focus: 5.0★ from 136 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 136 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 3720 N Orange Blossom Trl, Orlando, FL 32804
Based in Altamonte Springs, 3 mi away
64/100CR ScoreRanked #5 because of its Google rating and trade focus: 5.0★ from 99 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 99 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Longwood, 6 mi away
64/100CR ScoreRanked #6 because of its Google rating and trade focus: 5.0★ from 356 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 356 Google reviews
- Hours
- Mon–Sun 7 AM–7 PM
- Address
- 530 S Ronald Reagan Blvd #156, Longwood, FL 32750
Based in Belle Isle, 10 mi away
64/100CR ScoreRanked #7 because of its Google rating and trade focus: 5.0★ from 246 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 246 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Orlando, 7 mi away
64/100CR ScoreRanked #8 because of its Google rating and trade focus: 5.0★ from 373 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 373 Google reviews
- Hours
- Mon–Sat 8 AM–7 PM · Sun 9 AM–5 PM
- Address
- 47 Drennen Rd, Orlando, FL 32806
Based in Belle Isle, 13 mi away
63/100CR ScoreRanked #9 because of its Google rating and trade focus: 5.0★ from 654 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 654 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in DeBary, 8 mi away
63/100CR ScoreRanked #10 because of its Google rating and trade focus: 5.0★ from 315 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 315 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Horizon West, 17 mi away
63/100CR ScoreRanked #11 because of its Google rating and trade focus: 5.0★ from 419 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 419 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 13050 Sunkiss Loop, Windermere, FL 34786
Based in Ocoee, 9 mi away
63/100CR ScoreRanked #12 because of its Google rating and trade focus: 5.0★ from 118 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 118 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Oak Ridge, 13 mi away
62/100CR ScoreRanked #13 because of its Google rating and trade focus: 5.0★ from 409 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 409 Google reviews
- Hours
- Mon–Sun 6 AM–11 PM
Based in Winter Park
62/100CR ScoreRanked #14 because of its Google rating and trade focus: 5.0★ from 75 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 75 Google reviews
- Hours
- Mon–Wed 7 AM–7 PM · Thu 7 AM–7:30 PM · Fri–Sun 7 AM–7 PM
- Address
- 2814 Bongart Rd, Winter Park, FL 32792
Based in Azalea Park, 13 mi away
62/100CR ScoreRanked #15 because of its Google rating and trade focus: 5.0★ from 365 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 365 Google reviews
- Hours
- Mon–Sat 8 AM–7 PM · Sun 10 AM–6 PM
Based in Casselberry, 3 mi away
62/100CR ScoreRanked #16 because of its Google rating and trade focus: 5.0★ from 35 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 35 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 1357 Wilshire Blvd, Casselberry, FL 32707
Based in Apopka, 5 mi away
62/100CR ScoreRanked #17 because of its Google rating and trade focus: 4.9★ from 49 Google reviews, listed on Google as “Gutter cleaning service”.
- 4.9★ from 49 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Saint Cloud, 11 mi away
61/100CR ScoreRanked #18 because of its Google rating and trade focus: 5.0★ from 82 Google reviews, listed on Google as “Gutter service”.
- 5.0★ from 82 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Orlando, 6 mi away
61/100CR ScoreRanked #19 because of its Google rating and trade focus: 5.0★ from 41 Google reviews, listed on Google as “Gutter service”.
- 5.0★ from 41 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
- Address
- 750 S Orange Blossom Trl #235, Orlando, FL 32805
Based in Apopka, 10 mi away
61/100CR ScoreRanked #20 because of its Google rating and trade focus: 5.0★ from 40 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 40 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Kissimmee, 19 mi away
60/100CR ScoreRanked #21 because of its Google rating and trade focus: 5.0★ from 756 Google reviews, listed on Google as “Gutter service”.
- 5.0★ from 756 Google reviews
- Hours
- Mon–Fri 8 AM–5:30 PM · Sat 9 AM–3 PM · Sun closed
- Address
- 1300 Garden St, Kissimmee, FL 34744
Based in Fairview Shores, 9 mi away
60/100CR ScoreRanked #22 because of its Google rating and trade focus: 5.0★ from 36 Google reviews, listed on Google as “Gutter cleaning service”.
- 5.0★ from 36 Google reviews
- Open 24/7
- Hours
- Open 24 hours, 7 days
Based in Apopka, 8 mi away
60/100CR ScoreRanked #23 because of its Google rating and trade focus: 4.8★ from 270 Google reviews, listed on Google as “Gutter service”.
- 4.8★ from 270 Google reviews
- Hours
- Mon–Sat 8 AM–10 PM · Sun closed
- Address
- 2578 Clark St Suite 1, Apopka, FL 32703
#24 C & J Gutters
Based in Sanford, 13 mi away
60/100CR ScoreRanked #24 because of its Google rating and trade focus: 5.0★ from 131 Google reviews, listed on Google as “Gutter service”.
- 5.0★ from 131 Google reviews
- Hours
- Mon–Thu 8 AM–5 PM · Fri 8 AM–3 PM · Sat–Sun 9 AM–5 PM
- Address
- 228 Vinewood Dr, Sanford, FL 32773
Based in Orlando, 14 mi away
60/100CR ScoreRanked #25 because of its Google rating and trade focus: 4.9★ from 459 Google reviews, listed on Google as “Gutter cleaning service”.
- 4.9★ from 459 Google reviews
- Hours
- Mon–Fri 7 AM–5 PM · Sat 8 AM–2 PM · Sun closed
- Address
- 11334 Boggy Creek Rd ste 121, Orlando, FL 32824
Gutter installers ranked #26 to #50
#1 to #25 are shown in full above. Here are #26 to #50, in CR Score order; each links to its profile. We publish the top 50 of 270 ranked gutter installers here; the rest are on their profiles.
Also serving Winter Park
20 more gutter installers within 25 mi that we can't rank yet: too few reviews, or a trade we couldn't confirm. Listed A to Z.
| Business | Google rating | Distance |
|---|---|---|
| 3 Lotus Construction Group | 5.0★ (15) | In Winter Park |
| Absolute Quality Pro Wash | 5.0★ (2) | 12 mi |
| CHINEA'S DEVELOPERS & ROOFING CORP | 4.9★ (36) | In Winter Park |
| Clear Skies Roofing | 4.6★ (10) | In Winter Park |
| ED Aluminum Construction | 4.7★ (217) | In Winter Park |
| Ed Seamless Gutters | In Winter Park | |
| Edge 2 Edge Roofing | 5.0★ (19) | In Winter Park |
| Good Better Best Handymen | 5.0★ (2) | 10 mi |
| HC Roofing and Construction | 4.7★ (18) | In Winter Park |
| Michael Cranston Washing Service - Pressure Cleaning, Professional Pressure Washing in Apopka, FL | 5.0★ (2) | 14 mi |
| More Power 2 You Solar Cleaning | 5.0★ (2) | 23 mi |
| Orlando Central Cleaning | 5.0★ (1) | 4 mi |
| Professional Gutter Services of Orlando | 5.0★ (2) | 5 mi |
| Sheegog Contracting | 4.9★ (484) | In Winter Park |
| Stephens & Company | 5.0★ (15) | In Winter Park |
| The Roofing Doctor | 5.0★ (18) | In Winter Park |
| The Toolbox Store | 5.0★ (2) | 14 mi |
| Titan-Up Property Care LLC. | 5.0★ (2) | 25 mi |
| Versalis Group INC | 4.2★ (5) | In Winter Park |
| WDJ PAINTING LLC | 5.0★ (4) | In Winter Park |
How much do gutter installers cost in Winter Park?
National price ranges in USD, not adjusted for Winter Park. Each row names its basis and the month we checked it.
| Job | Low | Typical | High | Basis | Checked |
|---|---|---|---|---|---|
| Gutter installation | $600 | $3,200 | $5,800 | Per house: a typical 2,000 sq ft home (about 200 linear feet of gutter). US national range | October 2026 |
When to hire a gutter installer in Florida
Fall leaf drop is the busiest season for gutter cleaning. In Florida, it is worth checking gutters before the Atlantic hurricane season starts on June 1.
How we ranked Winter Park gutter installers
We scored 270 Winter Park gutter installers on ten factors, weighted as shown. A business is ranked when its trade is confirmed and it has 3 or more Google reviews or a claimed profile. A business with no Google reviews scores zero on rating, review volume and recency. Other unknown factors are left out, not counted as zero. Scores last refreshed October 22, 2026.
Paid placement never changes a rank or score. Featured businesses are paid, labelled, limited to 3 and shown above the ranking, outside it.
| Factor | Weight | Computed from | In Winter Park data |
|---|---|---|---|
| Reputation | 25% | Google star rating, adjusted for how many reviews back it | Measured |
| Credentials | 15% | Active state license, bond and workers’ comp on file | Not yet collected |
| Review volume | 10% | Number of Google reviews, compared with the most-reviewed business on the list | Measured |
| Recency | 5% | Share of reviews from the last 12 months | Not yet collected |
| Availability | 5% | Weekly open hours, Saturday, Sunday, 24/7 or same-day | Measured |
| Trade focus | 10% | How clearly the business does this trade (its Google category and name) | Measured |
| Proximity | 5% | Based in the city scores highest, less the farther away it is | Measured |
| Claimed profile | 10% | The business has claimed its ContractorsRanked profile (free or paid earn the same) | Measured |
| Partnered | 5% | The business links to ContractorsRanked from its own website with our badge, checked periodically | Measured |
| ContractorsRanked reviews | 10% | Verified customer reviews collected by ContractorsRanked: their rating and how many there are | Measured |
Gutter installers in Winter Park: frequently asked questions
Who is the best gutter installer in Winter Park?
By CR Score, the highest-ranked gutter installer in Winter Park, FL is Prestige Cleaning with a CR Score of 66/100. It has 5.0★ from 936 Google reviews. It is open 24/7. Gutter Masters of Central Florida (#2) and Proklean Pressure Washing LLC (#3) follow. We ranked 270 gutter installers on ten factors, last updated October 22, 2026.
How many gutter installers are there in Winter Park?
ContractorsRanked ranks 270 gutter installers serving Winter Park, FL. 1 of them is based in Winter Park; the rest serve it from nearby towns. Another 20 within 25 mi are listed but not ranked yet. Counts are as of October 2026.
Which gutter installers in Winter Park are open 24/7?
60 ranked gutter installers in Winter Park post 24/7 hours. The highest-ranked are Prestige Cleaning (#1), Gutter Masters of Central Florida (#2) and Proklean Pressure Washing LLC (#3). Hours come from each business's Google listing as of October 2026, so call to confirm.
Which gutter installers in Winter Park work on weekends?
185 of 270 ranked gutter installers post Saturday hours and 109 post Sunday hours. The highest-ranked open Saturdays are Prestige Cleaning (#1), Gutter Masters of Central Florida (#2) and Proklean Pressure Washing LLC (#3). Posted hours are office hours; crews may book weekend jobs separately.
How much does gutter installation cost in Winter Park?
Gutter installation typically costs $600 to $5,800, with $3,200 typical (Per house: a typical 2,000 sq ft home (about 200 linear feet of gutter). US national range). This is a national range, not adjusted for Winter Park. Prices were last checked October 2026. Get at least two written quotes before you hire.
What Google rating do Winter Park gutter installers have?
The median Google rating among 270 rated gutter installers in Winter Park is 5.0★, with a median of 35 reviews. Prestige Cleaning has the most, 936 reviews, and ranks #1. We adjust ratings for review count, so a few five-star reviews cannot top the list.
When is the best time to hire a gutter installer in Winter Park?
Fall leaf drop is the busiest season for gutter cleaning. In Florida, it is worth checking gutters before the Atlantic hurricane season starts on June 1.
How does ContractorsRanked rank gutter installers?
Each gutter installer gets a 0–100 CR Score from ten published factors, led by reputation (25%), credentials (15%), review volume (10%) and trade focus (10%). A business with no Google reviews scores zero on rating, review volume and recency; other factors we cannot measure are left out. Only businesses with a confirmed trade and 3 or more reviews, or a claimed profile, are ranked.
Update log for Winter Park
- October 2026: CR Scores recalculated for 270 gutter installers serving Winter Park.
More gutter installers and Winter Park pages
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