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Best Roof Repairs in Chesapeake, VA (2026)

18 verified businesses · Sorted by rating & reviews

Last updated: March 17, 2026 18 listings in Chesapeake, VA

Looking for a reliable roof repair in Chesapeake, VA? We've ranked the 18 best local businesses based on Google ratings and verified review counts. Each listing includes contact info, address, and a quality score so you can make a confident choice.

1

WT Anderson Roofing & Siding

Google ★★★★½ 4.9 628 reviews
→ Stable · 3 mo: 5.0★ (5) · 6 mo: 4.6★ (17) · 12 mo: 4.8★ (45)
4627 Cape Henry Ave, Norfolk, VA 23513
+1757-816-9203
Roofing contractor
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WT Anderson Roofing & Siding photo 1 WT Anderson Roofing & Siding photo 2 WT Anderson Roofing & Siding photo 3 WT Anderson Roofing & Siding photo 4 WT Anderson Roofing & Siding photo 5 WT Anderson Roofing & Siding photo 6 WT Anderson Roofing & Siding photo 7 WT Anderson Roofing & Siding photo 8 WT Anderson Roofing & Siding photo 9
2

Atlantic Craftsman LLC

Google ★★★★½ 4.8 547 reviews
↑ Improving · 3 mo: 5.0★ (7) · 6 mo: 4.4★ (37) · 12 mo: 4.6★ (54)
Staff: +Mike (2)
908 Business Park Dr Suite B, Chesapeake, VA 23320
+1757-780-5488
Roofing contractor
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3

Wholesale Roofers

Google ★★★★½ 4.8 412 reviews
↑ Improving · 3 mo: 5.0★ (3) · 6 mo: 4.3★ (13) · 12 mo: 4.5★ (22)
Staff: +tony (2)
1 Columbus Ctr #600, Virginia Beach, VA 23462
+1757-424-5981
Roofing contractor
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Wholesale Roofers photo 1 Wholesale Roofers photo 2 Wholesale Roofers photo 3 Wholesale Roofers photo 4
4

Jayhawk Exteriors

Google ★★★★½ 4.9 318 reviews
→ Stable · 3 mo: 5.0★ (7) · 6 mo: 5.0★ (20) · 12 mo: 5.0★ (50)
Staff: +Nick (2) +JayHawk (2)
1824 Engle Ave, Chesapeake, VA 23320
+1757-963-6559
Roofing contractor
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5

Pyramid Roofing (Southside)

Google ★★★★½ 4.9 290 reviews
→ Stable · 3 mo: 4.9★ (15) · 6 mo: 5.0★ (47) · 12 mo: 4.9★ (96)
4580 Village Ave suite A, Norfolk, VA 23502
+1757-574-9995
Roofing contractor
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6

Quality Built Roofing & Siding

Google ★★★★½ 4.5 439 reviews
↑ Improving · 3 mo: 5.0★ (3) · 6 mo: 4.6★ (8) · 12 mo: 4.5★ (14)
Staff: +steve (2)
929 Ventures Way # 109, Chesapeake, VA 23320
+1757-530-5131
Roofing contractor
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Quality Built Roofing & Siding photo 1 Quality Built Roofing & Siding photo 2 Quality Built Roofing & Siding photo 3 Quality Built Roofing & Siding photo 4 Quality Built Roofing & Siding photo 5 Quality Built Roofing & Siding photo 6 Quality Built Roofing & Siding photo 7 Quality Built Roofing & Siding photo 8 Quality Built Roofing & Siding photo 9 Quality Built Roofing & Siding photo 10 Quality Built Roofing & Siding photo 11 Quality Built Roofing & Siding photo 12 Quality Built Roofing & Siding photo 13 Quality Built Roofing & Siding photo 14 Quality Built Roofing & Siding photo 15 Quality Built Roofing & Siding photo 16 Quality Built Roofing & Siding photo 17
7

Exterior Source of Tidewater, VA

Google ★★★★½ 4.8 285 reviews
↑ Improving · 3 mo: 5.0★ (7) · 6 mo: 5.0★ (11) · 12 mo: 4.9★ (22)
Staff: +Nick (2)
1429 Crossways Blvd Ste B, Chesapeake, VA 23320
+1757-464-2060
Roofing contractor
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Exterior Source of Tidewater, VA photo 1 Exterior Source of Tidewater, VA photo 2
8

Best Choice Roofing

Google ★★★★½ 4.7 280 reviews
→ Stable · 3 mo: 4.8★ (5) · 6 mo: 4.9★ (11) · 12 mo: 5.0★ (33)
Staff: +ben (2)
2010 Old Greenbrier Rd Suite N, Chesapeake, VA 23320
+1757-913-5029
Roofing contractor
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Best Choice Roofing photo 1
9

Stublen Roofing

Google ★★★★½ 4.9 205 reviews
→ Stable · 3 mo: 5.0★ (24) · 6 mo: 4.9★ (43) · 12 mo: 4.9★ (63)
4011 Seaboard Ct, Portsmouth, VA 23701
+1757-488-8190
Roofing contractor
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Stublen Roofing photo 1 Stublen Roofing photo 2 Stublen Roofing photo 3 Stublen Roofing photo 4 Stublen Roofing photo 5 Stublen Roofing photo 6 Stublen Roofing photo 7 Stublen Roofing photo 8 Stublen Roofing photo 9 Stublen Roofing photo 10 Stublen Roofing photo 11 Stublen Roofing photo 12 Stublen Roofing photo 13 Stublen Roofing photo 14
10

Premier Roofing & Siding Contractors

Google ★★★★½ 4.6 195 reviews
→ Stable · 3 mo: 4.7★ (11) · 6 mo: 4.8★ (20) · 12 mo: 4.9★ (39)
1215 Bainbridge Blvd, Chesapeake, VA 23324
+1757-335-6950
Roofing contractor
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Premier Roofing & Siding Contractors photo 1 Premier Roofing & Siding Contractors photo 2 Premier Roofing & Siding Contractors photo 3 Premier Roofing & Siding Contractors photo 4 Premier Roofing & Siding Contractors photo 5 Premier Roofing & Siding Contractors photo 6 Premier Roofing & Siding Contractors photo 7 Premier Roofing & Siding Contractors photo 8 Premier Roofing & Siding Contractors photo 9 Premier Roofing & Siding Contractors photo 10 Premier Roofing & Siding Contractors photo 11 Premier Roofing & Siding Contractors photo 12 Premier Roofing & Siding Contractors photo 13 Premier Roofing & Siding Contractors photo 14
11

Gray Line Roofing

Google ★★★★½ 4.9 135 reviews
→ Stable · 3 mo: 4.8★ (17) · 6 mo: 5.0★ (70) · 12 mo: 4.9★ (96)
713 Fenway Ave Suite 3, Chesapeake, VA 23323
+1757-263-0232
Roofing contractor
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12

Roofing Systems of Hampton Roads

Google ★★★★½ 4.9 127 reviews
↓ Declining · 3 mo: 3.7★ (3) · 6 mo: 4.0★ (4) · 12 mo: 4.6★ (9)
Staff: +Victor (2)
+1800-757-6701
Roofing contractor
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Roofing Systems of Hampton Roads photo 1 Roofing Systems of Hampton Roads photo 2 Roofing Systems of Hampton Roads photo 3 Roofing Systems of Hampton Roads photo 4 Roofing Systems of Hampton Roads photo 5 Roofing Systems of Hampton Roads photo 6 Roofing Systems of Hampton Roads photo 7 Roofing Systems of Hampton Roads photo 8 Roofing Systems of Hampton Roads photo 9 Roofing Systems of Hampton Roads photo 10
13

Clark Roofing & Siding Inc

Google ★★★★½ 4.8 141 reviews
Staff: +Chuck (2)
1755 W Rd, Chesapeake, VA 23323
+1757-485-1000
Roofing contractor
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Clark Roofing & Siding Inc photo 1 Clark Roofing & Siding Inc photo 2 Clark Roofing & Siding Inc photo 3 Clark Roofing & Siding Inc photo 4 Clark Roofing & Siding Inc photo 5 Clark Roofing & Siding Inc photo 6 Clark Roofing & Siding Inc photo 7 Clark Roofing & Siding Inc photo 8 Clark Roofing & Siding Inc photo 9
14

Roof Artistry

Google ★★★★★ 5.0 59 reviews
→ Stable · 3 mo: 5.0★ (3) · 6 mo: 5.0★ (4) · 12 mo: 5.0★ (9)
1226 Executive Blvd Ste 101, Chesapeake, VA 23320
+1757-992-9311
Roofing contractor
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Roof Artistry photo 1 Roof Artistry photo 2 Roof Artistry photo 3 Roof Artistry photo 4 Roof Artistry photo 5 Roof Artistry photo 6 Roof Artistry photo 7 Roof Artistry photo 8 Roof Artistry photo 9 Roof Artistry photo 10 Roof Artistry photo 11 Roof Artistry photo 12 Roof Artistry photo 13 Roof Artistry photo 14
15

Roof Pros of Virginia

Google ★★★★½ 4.8 70 reviews
↑ Improving · 3 mo: 5.0★ (4) · 6 mo: 5.0★ (9) · 12 mo: 5.0★ (26)
Staff: +Chris (2)
445 Battlefield Blvd N E, Chesapeake, VA 23320
+1757-277-9100
Roofing contractor
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Roof Pros of Virginia photo 1 Roof Pros of Virginia photo 2 Roof Pros of Virginia photo 3
16

SlopePro Roofing

Google ★★★★★ 5.0 38 reviews
→ Stable · 3 mo: 5.0★ (6) · 6 mo: 5.0★ (7) · 12 mo: 5.0★ (19)
3712 Profit Way Ste A, Chesapeake, VA 23323
+1757-657-8059
Roofing contractor
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SlopePro Roofing photo 1 SlopePro Roofing photo 2 SlopePro Roofing photo 3 SlopePro Roofing photo 4 SlopePro Roofing photo 5 SlopePro Roofing photo 6
17

Wholesale Roofers Chesapeake

Google ★★★★★ 5.0 36 reviews
→ Stable · 3 mo: 5.0★ (2) · 6 mo: 5.0★ (4) · 12 mo: 5.0★ (14)
2211 S Military Hwy Ste B, Chesapeake, VA 23320
+1757-266-5981
Roofing contractor
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Wholesale Roofers Chesapeake photo 1 Wholesale Roofers Chesapeake photo 2 Wholesale Roofers Chesapeake photo 3 Wholesale Roofers Chesapeake photo 4
18

GTO Home Repair

Google ★★★★½ 4.8 18 reviews
+1757-944-8826
Roofing contractor
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