62 gutter installers ranked by CR ScoreUpdated 0 paid placements in this rankingHow we rank →
Best overall in Winchester: Cherry’s Outdoor Services, CR Score 60/100; 5.0★ from 103 Google reviews; open 24/7.
Best for emergencies (open 24/7): MidWest Gutter, posts 24/7 hours; ranked #4 of 62.
Most-reviewed: AIC Roofing & Construction Inc, 655 Google reviews at 4.9★, the most of 62 ranked; ranked #26.
Rankings can't be bought. Contractors can't pay to change their rank or score. How we rank
62 Winchester gutter installers are ranked here by CR Score, from ten published factors. 15 are open 24/7, 38 open Saturdays and 22 open Sundays, based on posted hours. The median Google rating is 5.0★ across 62 rated businesses.
| Rank | Business | CR Score | Google rating | Based in | Hours | Best for |
|---|---|---|---|---|---|---|
| 1 | Cherry’s Outdoor Services | 60 | 5.0★ (103) | Lexington, 19 mi away | 24/7 | Overall |
| 2 | Simply Clean Pressure Washing & Window Cleaning | 60 | 5.0★ (237) | Richmond, 20 mi away | Sat · Sun · Evenings | — |
| 3 | Troy's Exterior Cleaning | 59 | 5.0★ (140) | Lexington-Fayette, 19 mi away | Sat · Sun · Evenings | — |
| 4 | MidWest Gutter | 58 | 4.7★ (24) | Lexington-Fayette, 13 mi away | 24/7 | Emergencies |
| 5 | Begich Gutter Company | 58 | 5.0★ (97) | Lexington, 15 mi away | Sat | — |
| 6 | Men In Kilts Lexington | 57 | 5.0★ (189) | Lexington-Fayette, 16 mi away | — | — |
| 7 | McDowells gutters | 57 | 4.5★ (26) | Lexington-Fayette, 16 mi away | 24/7 | — |
| 8 | Bone Dry Roofing | 57 | 4.7★ (602) | Lexington, 15 mi away | 24/7 | — |
| 9 | Barrier Roofs | 57 | 4.9★ (435) | Lexington, 18 mi away | 24/7 | — |
| 10 | The Brothers That Just Do Gutters | 57 | 5.0★ (57) | Lexington, 17 mi away | Sat · Evenings | — |
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.
Ranked #1 because of its Google rating and trade focus: 5.0★ from 103 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Richmond, 20 mi away
Ranked #2 because of its Google rating and trade focus: 5.0★ from 237 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington-Fayette, 19 mi away
Ranked #3 because of its Google rating and trade focus: 5.0★ from 140 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington-Fayette, 13 mi away
Ranked #4 because of its Google rating and trade focus: 4.7★ from 24 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington, 15 mi away
Ranked #5 because of its Google rating and trade focus: 5.0★ from 97 Google reviews, listed on Google as “Gutter service”.
Based in Lexington-Fayette, 16 mi away
Ranked #6 because of its Google rating and trade focus: 5.0★ from 189 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington-Fayette, 16 mi away
Ranked #7 because of its Google rating and trade focus: 4.5★ from 26 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington, 15 mi away
Ranked #8 because of its Google rating and review volume: 4.7★ from 602 Google reviews.
Based in Lexington, 18 mi away
Ranked #9 because of its Google rating and review volume: 4.9★ from 435 Google reviews.
Based in Lexington, 17 mi away
Ranked #10 because of its Google rating and trade focus: 5.0★ from 57 Google reviews, listed on Google as “Gutter service”.
Based in Richmond, 17 mi away
Ranked #11 because of its Google rating and trade focus: 4.8★ from 89 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington, 18 mi away
Ranked #12 because of its Google rating and review volume: 4.8★ from 387 Google reviews.
Based in Richmond, 16 mi away
Ranked #13 because of its Google rating and trade focus: 5.0★ from 14 Google reviews, listed on Google as “Gutter service”.
Based in Lexington, 15 mi away
Ranked #14 because of its Google rating and review volume: 4.9★ from 94 Google reviews.
Based in Winchester
Ranked #15 because of its Google rating and review volume: 5.0★ from 25 Google reviews.
Based in Lexington-Fayette, 16 mi away
Ranked #16 because of its Google rating and trade focus: 5.0★ from 7 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington, 19 mi away
Ranked #17 because of its Google rating and trade focus: 4.6★ from 40 Google reviews, listed on Google as “Gutter service”.
Based in Lexington, 17 mi away
Ranked #18 because of its Google rating and trade focus: 5.0★ from 46 Google reviews, listed on Google as “Gutter service”.
Based in Lexington, 19 mi away
Ranked #19 because of its Google rating and trade focus: 4.4★ from 39 Google reviews, listed on Google as “Gutter cleaning service”.
Based in Lexington-Fayette, 16 mi away
Ranked #20 because of its Google rating and trade focus: 4.9★ from 91 Google reviews, listed on Google as “Roofing contractor”.
Based in Lexington, 15 mi away
Ranked #21 because of its Google rating and review volume: 5.0★ from 41 Google reviews.
Based in Lexington, 13 mi away
Ranked #22 because of its Google rating and review volume: 4.6★ from 149 Google reviews.
Based in Richmond, 20 mi away
Ranked #23 because of its Google rating and review volume: 5.0★ from 62 Google reviews.
Based in Lexington-Fayette, 20 mi away
Ranked #24 because of its Google rating and review volume: 5.0★ from 133 Google reviews.
Based in Richmond, 17 mi away
Ranked #25 because of its Google rating and review volume: 5.0★ from 205 Google reviews.
#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 62 ranked gutter installers here; the rest are on their profiles.
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 |
|---|---|---|
| Big Blue Power Pressure Soft Washing | 5.0★ (7) | In Winchester |
| Eagle's Eye Handyman - General Handyman Services, Handyman Gutter Repair, General Handyman, Handyman Service, Handyman | In Winchester | |
| EVERFLOW GUTTER SOLUTIONS LLC | 5.0★ (2) | 20 mi |
| Express Roofing | 4.5★ (40) | In Winchester |
| Fast Gutter Pros | 1.0★ (1) | 20 mi |
| Franklin Roofing LLC | 4.8★ (39) | In Winchester |
| Full Throttle Spray Foam & Seamless Gutters LLC | 5.0★ (1) | 22 mi |
| Gutter Cleaning Lexington | 5.0★ (1) | 24 mi |
| Howard Roofing Llc | In Winchester | |
| Leaf Free Gutters | 1.0★ (1) | 20 mi |
| LikeNew Lexington Gutters | 5.0★ (1) | 16 mi |
| Mansea Metal | 4.7★ (69) | In Winchester |
| Osborne Roofing | 5.0★ (7) | In Winchester |
| Precision Services | 5.0★ (22) | In Winchester |
| Professional Gutter Services of Lexington | 1.0★ (1) | 18 mi |
| R 5 Roofing and Construction | 5.0★ (2) | 20 mi |
| R&R Gutter | 5.0★ (2) | 3 mi |
| Trace O' Sunshine Gutter Biz | 5.0★ (1) | 18 mi |
| Unlimited Roofing | 4.6★ (9) | In Winchester |
| Weatherguard Roofing & Restoration - Lexington | 5.0★ (2) | 20 mi |
National price ranges in USD, not adjusted for Winchester. 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 |
Fall, after leaves drop, is the busiest season for gutter cleaning and repairs. Booking in late summer usually means shorter waits.
We scored 62 Winchester 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 Winchester 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 |