Published May 12, 2026 · Last updated October 21, 2026
Leak Repair Roofing in Chesapeake, Virginia: 19 Top Pros (2027)
Quick answer
The top-ranked Roofing provider in Chesapeake is Jayhawk Exteriors (Chesapeake), with a 4.9★ rating across 318 Google reviews and a ServiceAgent Score of 8.5/10. Also strongly rated: Atlantic Craftsman LLC and Gray Line Roofing. See the full ranked list and how each provider scores below.
TL;DR
Ranked: 1. Jayhawk Exteriors · 2. Atlantic Craftsman LLC · 3. Gray Line Roofing · 4. Roof Artistry · 5. Best Choice Roofing
- 19 leak repair roofing providers match in Chesapeake, Virginia.
- Top pick: Jayhawk Exteriors (ServiceAgent Score 8.5/10).
- Median ServiceAgent Score: 8.0/10.
- 0 owner-verified listings.
- Filtered for Leak Repair: targeted leak diagnosis + sealing.
Computed from the providers ranked on this page. Figures update with each data refresh.
At-a-glance: top 11 roofing pros in Chesapeake
Compare the top picks side-by-side. Full reviews of each below.
SA Score = ServiceAgent composite (0–10). Tap a row number to jump to the full review.
How the top roofing pros compare
The same ServiceAgent Score components that drive the ranking, scored side by side — so you can see at a glance where each provider is strongest.
The criteria we scored against
- 1. Trust (data & verification). Owner-verification, completeness of contact info, and review-volume credibility.
- 2. Recommendation (rating). The Google star rating, Bayesian-shrunk toward the category mean so a few 5-star reviews can't dominate.
- 3. Review depth. How many public reviews back the rating — more reviews, more reliable the signal.
- 4. Score confidence. How much data stands behind the composite score for this provider.
| Provider | Trust (data & verification) | Recommendation (rating) | Review depth | Score confidence |
|---|---|---|---|---|
| Jayhawk Exteriors | Strong | Strong | Strong | Strong |
| Atlantic Craftsman LLC | Strong | Strong | Strong | Strong |
| Gray Line Roofing | Moderate | Strong | Moderate | Strong |
| Roof Artistry | Moderate | Strong | Moderate | Strong |
| Best Choice Roofing | Strong | Strong | Strong | Strong |
| Clark Roofing & Siding Inc | Moderate | Strong | Moderate | Strong |
| Roof Pros of Virginia | Moderate | Strong | Moderate | Strong |
| SlopePro Roofing | Moderate | Strong | Limited | Limited |
How we chose these
Same scoring engine as the main Chesapeake roofing ranking, with an additional filter step: we look for Leak Repair signals in each provider's business categories, service tags, and recent review text.
When the Leak Repair filter would surface fewer than five providers, we fall back to showing top-rated roofing pros generally - they are far more likely to handle leak repair work than an unrated provider would be.
Full formula on the methodology page.
19 Best Roofing Companies Ranked
Ranked by composite ServiceAgent Score. 19 verified businesses match.
Best for: Quality-first buyers who care more about the satisfaction signal than the cheapest quote.
| Location | Chesapeake, VA · 1824 Engle Ave, Chesapeake, VA 23320 |
|---|---|
| Established | Established (high review volume) |
| Specialization | Roofing |
| Rating | 4.9★ across 318 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Jayhawk Exteriors maintains a strong 4.9-star reputation across 318 reviews in Chesapeake, suggesting consistent execution rather than a one-off lucky streak.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.9-star average across 318 reviews is in the top 5% of providers in Chesapeake - unusually high satisfaction signal at this volume.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Our top pick in Chesapeake. The 8.5/10 composite comes from a rare combination of review depth (318 reviews), a 4.9-star rating, and complete profile data.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 963-6559 |
| Website | www.jhawkext.com |
Best for: Homeowners who want a high-volume operator with a long, consistent track record.
| Location | Chesapeake, VA · 908 Business Park Dr Suite B, Chesapeake, VA 23320 |
|---|---|
| Established | Established (very high review volume) |
| Specialization | Roofing |
| Rating | 4.8★ across 549 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Atlantic Craftsman LLC has built a high-volume operation in Chesapeake, with 549 Google reviews averaging 4.8 stars. That kind of review velocity in a single market typically means a fleet-style operation with multiple crews and a predictable response window.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.8-star average across 549 reviews points to consistent on-time delivery and clear communication.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
A top-3 pick in this market on the composite score. Worth a quote alongside #1 to compare response time and pricing on your specific job.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 780-5488 |
| Website | www.atlanticcraftsman.com |
Best for: Customers prioritizing top-end satisfaction scores in Chesapeake.
| Location | Chesapeake, VA · 713 Fenway Ave Suite 3, Chesapeake, VA 23323 |
|---|---|
| Established | Operating multiple years (moderate review history) |
| Specialization | Roofing |
| Rating | 4.9★ across 139 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Gray Line Roofing maintains a strong 4.9-star reputation across 139 reviews in Chesapeake, suggesting consistent execution rather than a one-off lucky streak.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.9-star average across 139 reviews is in the top 5% of providers in Chesapeake - unusually high satisfaction signal at this volume.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
A top-3 pick in this market on the composite score. Worth a quote alongside #1 to compare response time and pricing on your specific job.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 263-0232 |
| Website | graylineroofingva.com/?utm_source=google&utm_medium=organic&utm_campaign=gmb |
Best for: Customers prioritizing top-end satisfaction scores in Chesapeake.
| Location | Chesapeake, VA · 1226 Executive Blvd Ste 101, Chesapeake, VA 23320 |
|---|---|
| Established | Operating multiple years (moderate review history) |
| Specialization | Roofing |
| Rating | 5.0★ across 60 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Roof Artistry operates in Chesapeake with 60 Google reviews at 5.0 stars - a steady mid-tier signal in our composite scoring.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
5.0-star average across 60 reviews points to consistent on-time delivery and clear communication.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Mid-tier ranking in this market. Quality looks reasonable but isn't a standout vs. the top 3 - use them if you can't get a quote from a higher-ranked provider in time.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 992-9311 |
| Website | roofartistry.com/?utm_source=google&utm_medium=organic&utm_campaign=gbp |
Best for: Mid-tier roofing jobs where price and quality both matter.
| Location | Chesapeake, VA · 2010 Old Greenbrier Rd Suite N, Chesapeake, VA 23320 |
|---|---|
| Established | Established (high review volume) |
| Specialization | Roofing |
| Rating | 4.7★ across 282 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Best Choice Roofing operates in Chesapeake with 282 Google reviews at 4.7 stars - a steady mid-tier signal in our composite scoring.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.7-star average across 282 reviews puts them in the upper tier for roofing providers in Chesapeake.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Ranked here because of high review depth at a strong rating - the kind of provider you can hire without doing 90 minutes of due diligence.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 913-5029 |
| Website | bestchoiceroofing.com/chesapeake/?utm_source=gmb&utm_medium=organic&utm_campaign=chesapeake |
Best for: Mid-tier roofing jobs where price and quality both matter.
| Location | Chesapeake, VA · 1755 W Rd, Chesapeake, VA 23323 |
|---|---|
| Established | Operating multiple years (moderate review history) |
| Specialization | Roofing |
| Rating | 4.8★ across 141 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Clark Roofing & Siding Inc maintains a strong 4.8-star reputation across 141 reviews in Chesapeake, suggesting consistent execution rather than a one-off lucky streak.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.8-star average across 141 reviews points to consistent on-time delivery and clear communication.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Mid-tier ranking in this market. Quality looks reasonable but isn't a standout vs. the top 3 - use them if you can't get a quote from a higher-ranked provider in time.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 485-1000 |
| Website | clarkroofingandsiding.com/?utm_source=gbp&utm_medium=organic |
Best for: Mid-tier roofing jobs where price and quality both matter.
| Location | Chesapeake, VA · 445 Battlefield Blvd N E, Chesapeake, VA 23320 |
|---|---|
| Established | Operating multiple years (moderate review history) |
| Specialization | Roofing |
| Rating | 4.8★ across 70 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Roof Pros of Virginia operates in Chesapeake with 70 Google reviews at 4.8 stars - a steady mid-tier signal in our composite scoring.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
4.8-star average across 70 reviews points to consistent on-time delivery and clear communication.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Mid-tier ranking in this market. Quality looks reasonable but isn't a standout vs. the top 3 - use them if you can't get a quote from a higher-ranked provider in time.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 277-9100 |
| Website | roofprosofvirginia.com |
Best for: Customers prioritizing top-end satisfaction scores in Chesapeake.
| Location | Chesapeake, VA · 3712 Profit Way Ste A, Chesapeake, VA 23323 |
|---|---|
| Established | Some operating history (limited review volume) |
| Specialization | Roofing |
| Rating | 5.0★ across 38 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
SlopePro Roofing operates in Chesapeake with 38 Google reviews at 5.0 stars - a steady mid-tier signal in our composite scoring.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
5.0-star average across 38 reviews puts them in the upper tier for roofing providers in Chesapeake.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Ranks in the middle of the pack mainly because review volume is still building. The rating itself is strong; treat them as a "worth a quote" rather than a default pick.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 657-8059 |
| Website | www.slopeproroofing.com/service-areas/chesapeake |
Best for: Customers prioritizing top-end satisfaction scores in Chesapeake.
| Location | Chesapeake, VA · 2211 S Military Hwy Ste B, Chesapeake, VA 23320 |
|---|---|
| Established | Some operating history (limited review volume) |
| Specialization | Roofing |
| Rating | 5.0★ across 36 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Wholesale Roofers Chesapeake operates in Chesapeake with 36 Google reviews at 5.0 stars - a steady mid-tier signal in our composite scoring.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
5.0-star average across 36 reviews puts them in the upper tier for roofing providers in Chesapeake.
⚠ Watch out for
After-hours and emergency response isn't signaled on the public profile - confirm availability directly if your job is time-sensitive.
Our take
Ranks in the middle of the pack mainly because review volume is still building. The rating itself is strong; treat them as a "worth a quote" rather than a default pick.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 266-5981 |
| Website | www.wholesaleroofersva.com/chesapeake |
Best for: Buyers willing to try a newer entrant with strong early reviews.
| Location | Chesapeake, VA · 2633 Cornet St, Chesapeake, VA 23321 |
|---|---|
| Established | Some operating history (limited review volume) |
| Specialization | Roofing |
| Rating | 5.0★ across 15 Google reviews |
| Status | Unclaimed listing (Google data) |
| Source | Public Google Business Profile · data as of May 12, 2026 |
The approach
Flat Roofs by Pegram is a smaller or newer entrant in Chesapeake with 15 public reviews so far. The smaller sample makes the 5.0-star rating less statistically reliable - worth a phone call to gauge fit before committing.
- Maintains an active website with service detail.
- Direct phone published - no lead form gatekeeping.
- Active on Google with up-to-date contact info.
✓ Strong review signal
5.0-star average across 15 reviews puts them in the upper tier for roofing providers in Chesapeake.
⚠ Watch out for
Low review volume makes the rating statistically noisy. Get references from 2-3 recent jobs before signing.
Our take
Ranks in the middle of the pack mainly because review volume is still building. The rating itself is strong; treat them as a "worth a quote" rather than a default pick.
| 24/7 emergency | Not advertised |
|---|---|
| Free estimate | Not advertised |
| Licensed + insured | Not advertised - verify before hiring |
| Phone | (757) 537-1945 |
| Website | flatroofsbypegram.com |
Showing 10 of 19.
How to choose a roofing pro
The ranking does the research; these five checks help you turn the shortlist into the right hire.
- 1
Start with the top of the ranking, not an ad
The providers ranked highest in Chesapeake earned it on review depth, rating, and data completeness — not on ad spend. Shortlist two or three from the top before you start calling.
- 2
Get two or three quotes in writing
Pricing for roofing work varies by scope and local market. Written quotes from a few shortlisted pros let you compare apples to apples and spot an outlier before you commit.
- 3
Read the most recent reviews, not just the average
A strong average can hide a recent slide in quality. Sort reviews by newest and look for how the business handles problems — a thoughtful reply to a bad review often tells you more than the star count.
- 4
Confirm licensing, insurance, and scope before work starts
Ask for the license number and proof of insurance, and get the full scope of work plus any parts/labor warranty in writing before any roofing job begins. Verify the license on your state board if the work is significant.
- 5
Match the provider to your actual job
A high-volume operator is great for a routine job; a smaller specialist may be a better fit for an unusual one. Use the scorecard above to pick for your situation, not just the overall rank.
Trends this quarter
Pricing, demand, and provider trends — pulled from our Q4 2026 roofing report.
- 19 roofing providers tracked in Chesapeake this quarter, with an average ServiceAgent Score of 8.0/10.
- 1 elite-tier providers (Score ≥ 8.5/10), and an average Google rating of 4.74★.
- Total review volume changed by -8.6% quarter-over-quarter — a leading indicator of local roofing demand.
- Median quote price moved -3.2% vs. the previous quarter for typical roofing jobs.
- 0% of providers are owner-verified (+1.9% QoQ).
Source: ServiceAgent Roofing trends in Chesapeake, Q4 2026. Quarterly methodology and full commentary available in the full report.
When demand peaks in Chesapeake for roofing
12-month demand index (100 = annual average). Peaks in September, troughs in January. Book in the trough months to lock lower rates.
Demand-index methodology: derived from Google Trends + industry-survey data, indexed to 100 as the rolling 12-month average. Local market may vary 10-25%.
Pricing: what roofing costs
Quick budget estimates by job type. Use these as a planning sanity-check, not as a firm quote.
| Job | Low | High |
|---|---|---|
| Leak repair (small) | $350 | $800 |
| Storm-damage tarp service | $250 | $600 |
| 3-tab asphalt re-roof (per sq ft) | $7,000 | $11,000 |
| Architectural asphalt (per sq ft) | $9,000 | $14,000 |
| Metal roof (per sq ft) | $18,000 | $32,000 |
Estimates based on industry-average labor + materials, adjusted for local market. Get at least two written quotes from providers above before signing.
What to know about hiring Roofing
Roofing is a high-stakes, weather-dependent job where material choice and install quality matter more than the headline quote.
What drives the price
Roof size (squares), pitch, material (asphalt vs. metal vs. tile), tear-off of the old roof, and decking repairs found mid-job.
What to check
Manufacturer certifications, a written workmanship warranty, proof of insurance, and that they'll pull the permit.
When to call
After storm season for inspections; get multiple quotes and avoid storm-chasers who knock door-to-door after hail.
Why trust this list
This page narrows the full Chesapeake roofing directory to providers that explicitly serve leak repair requests. We surfaced them by scanning provider categories, service tags, and review text for relevant signals.
If you're looking at this page, you probably need leak repair roofing now - so we've ordered the list by composite ServiceAgent Score and surfaced the response-time indicator on every card. Call the top three; the first to pick up usually wins the job.
Frequently asked questions
8 common questions about hiring a roofing pro in this area.
Who offers leak repair roofing in Chesapeake?
Jayhawk Exteriors and 18 other roofing businesses in Chesapeake offer leak repair service. See the ranked list above; the top picks have the strongest combination of reviews, verification, and leak repair signals.
How fast can a leak repair roofing pro arrive?
Response time varies by provider and current job load. Claimed listings display their average response window directly on the profile - aim for providers showing under-24-hour replies.
What does leak repair roofing cost in Chesapeake?
Cost depends on scope and materials. Get at least two written estimates - most Chesapeake roofing providers offer free quotes for leak repair work.
Are these providers licensed and insured?
Listings tagged with ✓ Licensed & insured have that signal in their provider data. Always verify directly with the provider before any work, and confirm coverage via your state license board.
How is this list different from the main Roofing in Chesapeake page?
This page is filtered to providers offering leak repair service specifically. The main Roofing in Chesapeake page lists every provider regardless of intent.
Who are the highest-rated roofing providers in Chesapeake?
Based on composite ServiceAgent Score, Jayhawk Exteriors in Chesapeake ranks #1 (8.5/10). Atlantic Craftsman LLC and Gray Line Roofing round out the top 3.
How does the ServiceAgent Score work?
It's a 0-10 composite of a Trust Score (40% - data quality, verification and review-volume credibility) and a Recommendation Score (60% - the Google rating Bayesian-shrunk toward the category mean using a 25-review prior). Full formula on the methodology page.
Are these listings verified?
Every listing is pulled from active Google Business Profile data. 0 of these 19 listings are currently ServiceAgent-verified (owners completed our claim flow). Verified listings get a green badge in the ranking.
Reports & insights
Pricing, demand, and provider trends for Chesapeake — refreshed quarterly.
Roofing trends in Chesapeake, Q4 2026
Pricing, demand, and review-volume trends for roofing providers in Chesapeake.
Home-service trends in Chesapeake, Virginia (Q4 2026)
Across every category, here's what's changing in the Chesapeake home-service market this quarter.
State of Roofing in Virginia, Q4 2026
Pricing trends, demand signals, and elite-tier shifts for roofing providers across Virginia.
State of home services in Virginia, Q4 2026
Pricing, demand, and provider trends across every home-service category in Virginia.
State of Plumbing in Virginia, Q4 2026
Pricing trends, demand signals, and elite-tier shifts for plumbing providers across Virginia.
State of Electricians in Virginia, Q4 2026
Pricing trends, demand signals, and elite-tier shifts for electricians providers across Virginia.
Verify any provider's license in Virginia
Always confirm a contractor is in good standing before hiring. Virginia uses the Virginia Department of Professional and Occupational Regulation (DPOR). Search by license number, business name, or address.
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Fill out the verification form right here. We'll match it to your Google Business Profile and confirm by phone within one business day.
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About the author
Written by
Growth & Product Marketing, ServiceAgent
Shaambhav Shankar works in product marketing at SaaS Labs, the company behind ServiceAgent, and describes himself as a marketing generalist with six years of experience in SaaS. He studied at Symbiosis International University and is based in the Greater Delhi Area. He writes the bulk of the ServiceAgent blog, covering call answering, CRM and the operational side of running a home services business, and authors and maintains the ServiceAgent Directory rankings.
Credentials
- Symbiosis International University (2016-2019)
- Digital Marketing, Google India (2020)
- Financial Modelling and Valuation, Ernst & Young (2019)
- Building with the Claude API, Anthropic (2026)
- AI Fluency for Builders, Anthropic (2026)
- Introduction to Model Context Protocol, Anthropic (2026)
Greater Delhi Area, India · 6 years experience
Every ranking on this page is written and maintained by Shaambhav Shankar, who owns the ranking methodology and verifies each provider listing against public data. No pay-to-rank, no sponsored placements. Read our methodology →
Update history
- October 21, 2026 — Latest ranking refresh. Composite ServiceAgent Scores recomputed from current Google review data.
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