Roofing Contractors in Milton, MA
Roofing Contractors in Milton, MA understand that your home’s roof is more than just protection — it’s a key part of how your property looks, performs, and holds its value over time. Milton’s tree-lined streets and mix of home styles call for roofing that’s both tough and tasteful.
Certified Expertise
Eco-Friendly Solutions
Storm-Ready Roofing
Professionals in the area know how to match design with durability. They choose materials that resist moss, mold, and weather damage while fitting the look of your home. From complete roof replacements to detailed repair work, quality contractors bring lasting results and clean finishes every time.
When your roof needs attention, don’t settle. Go with a team that sees the big picture and gets every detail right.
US Veteran-Owned Quality Roofing
50-Year Roofing Guarantee
Up to $3,000 Off on Eligible Projects!
Delivering Unmatched Quality and Service
Experience the difference across Boston and Greater Boston. Our commitment to excellence sets us apart.
Expert Craftsmanship
Our team's skills ensure top-notch quality in every project.
Sustainable Materials
We use eco-friendly materials for a greener future.
Customized Solutions
Tailored services to meet your specific needs.
Competitive Pricing
Quality services at affordable rates.
Veteran-Owned
A company with a commitment to integrity and excellence.
Local Expertise
Decades of experience specific to Boston's New England climate.
Hear from Our Satisfied Clients
Discover why homeowners trust us for their exterior remodeling needs. Your satisfaction is our success.
Project – CertainTeed Landmark PRO Roof Replacement in Yarmouth, MA
Project Year:
2026
Object Size:
2,600–2,800 sq. ft.
Project Cost:
$17,000–19,000
Location:
Yarmouth, MA
Project – Asphalt Roof Replacement in Harwich, MA
Roof Material:
Asphalt Shingle
Project Year:
2026
Location:
Harwich, MA
Services:
Roofing
Project – Composite Deck & Walkway Installation in West Yarmouth, MA
Deck Material:
Composite Decking
Project Year:
2026
Location:
West Yarmouth, MA
Services:
Decks
Project – Composite Deck Installation in Chatham, MA
Deck Material:
Composite Decking
Project Year:
2026
Location:
Chatham, MA
Services:
Decks
Project – CertainTeed Monogram Vinyl Siding Installation in North Andover, MA
Project Year:
2026
Object Size:
2,800–3,200 sq. ft.
Project Cost:
$44,000–46,000
Location:
North Andover, MA
Project – White Cedar Shingle Siding Installation in Dennis, MA
Siding Material:
White Cedar Shingles
Project Year:
2026
Location:
Dennis, MA
Services:
Siding
Project – White Cedar Shingle Siding Installation in Orleans, MA
Siding Material:
White Cedar Shingles
Project Year:
2026
Location:
Orleans, MA
Services:
Siding
Project – Standing Seam Metal Roof Installation in Plymouth, MA
Roof Material:
Standing Seam Metal Roofing
Underlayment:
Elevate Clad-Gard SA
Project Year:
2026
Location:
Plymouth, MA
Project – CertainTeed Landmark PRO Roof Replacement in Harwich, MA
Project Year:
2026
Object Size:
4,900–5,300 sq. ft.
Project Cost:
$32,000–35,000
Location:
Harwich, MA
Project – Cedar Siding, CertainTeed Roof & Andersen Windows in Falmouth, MA
Project Year:
2025
Object Size:
1,100-1,200 sq ft
Project Cost:
$80,000 – 85,000
Location:
Falmouth MA, MA
Project – White Cedar Shingle Siding Installation in Bourne, MA
Project Year:
2025
Object Size:
1,100-1,200 sq ft
Project Cost:
$15,000 – 17,000
Location:
Bourne, MA
Project – James Hardie Shingle Panel Siding in Sagamore Beach, MA
Project Year:
2025
Object Size:
1,900-2,000 sq ft
Project Cost:
36,000 – 40,000
Location:
Sagamore Beach, MA
Project – CertainTeed Landmark PRO Roof Replacement in Bourne, MA
Project Year:
2025
Object Size:
41,000 sq ft
Project Cost:
24,000 – 29,000
Location:
Bourne, MA
Project – GAF Timberline HDZ Roof Replacement in East Falmouth, MA
Project Year:
2025
Object Size:
3,000 sq ft
Project Cost:
19,000 – 21,000
Location:
East Falmouth, MA
Project – CertainTeed Landmark Roof Replacement in Sandwich, MA
Project Year:
2025
Object Size:
3,200 sq ft
Project Cost:
18,000 – 22,000
Location:
Sandwich, MA
Project – James Hardie Lap Siding Installation in Boston, MA
Project Year:
2025
Object Size:
4,500 sq ft
Project Cost:
67,000 – 75,000
Location:
Boston, MA
Project – Cedar Impression Vinyl Siding Installation in Dennis Port, MA
Project Year:
2025
Object Size:
1,600 sq ft
Project Cost:
23,000 – 27,000
Location:
Dennis Port, MA
Project – White Cedar Shingle Siding Installation in Orleans, MA
Project Year:
2025
Object Size:
2,000 sq ft
Project Cost:
28,000 – 32,000
Location:
Orleans, MA
Project – Brava Composite Spanish Barrel Tile Roof Replacement in Boston, MA
Project Year:
2025
Object Size:
150 sq ft
Project Cost:
12,000 – 15,000
Location:
Falmouth, MA
Project – Brava Composite Spanish Barrel Tile Roof Replacement in Marion, MA
Project Year:
2025
Object Size:
4,600 sq ft
Project Cost:
110,000 – 140,000
Location:
Marion, MA
Project – Brava Composite Spanish Barrel Tile Roof Replacement in Boston, MA
Project Year:
2024
Object Size:
2,500 sq ft
Project Cost:
58,000 – 65,000
Location:
Boston, MA
Project – CertainTeed Landmark PRO Roof Replacement in Newton, MA
Project Year:
2025
Object Size:
4,500 sq ft
Project Cost:
30,000 – 35,000
Location:
Newton, MA
Project – CertainTeed Landmark PRO Roof Replacement in Brewster, MA
Project Year:
2025
Object Size:
4,500 sq ft
Project Cost:
25,000 – 30,000
Location:
Brewster, MA
Project – CertainTeed Highland Slate Roof Replacement in Topsfield, MA
Project Year:
2025
Object Size:
4,000 sq ft
Project Cost:
62,000 – 65,000
Location:
Topsfield, MA
Project – Backyard Landscape Design & Hardscaping in Orleans, MA
Project year:
2024
Object size:
2,800 sq ft
Project cost:
$12,000 – $18,000
Location:
Orleans, MA
Project – Attic Insulation & Ventilation in Yarmouth, MA
Project year:
2024
Object size:
2,200 sq ft
Project cost:
$5,500 – $7,500
Location:
Yarmouth, MA
Project – Storm-Damaged Roof Restoration in Bourne, MA
Project Year:
2024
Object Size:
2,400 sq ft
Project Cost:
$14,000 – $18,000
Location:
Bourne, MA
Project – Commercial Flat Roof Retrofit in Barnstable, MA
Project Year:
2024
Object Size:
7,200 sq ft
Project Cost:
$32,000 – $45,000
Location:
Barnstable, MA
Project – Siding & Window Upgrade in Centerville, MA
Project Year:
2024
Object Size:
2,700 sq ft
Project Cost:
$25,000 – $30,000
Location:
Centerville, MA
Project – Full Roof & Deck Replacement in Truro, MA
Project Year:
2024
Object Size:
3,200 sq ft
Project Cost:
$35,000 – $42,000
Location:
Truro, MA
Project – Gutter & Fascia Replacement in Harwich, MA
Project Year:
2024
Object Size:
2,200 sq ft
Project Cost:
$5,000 – $7,000
Location:
Harwich, MA
Project – Composite Siding Installation in Orleans, MA
Project Year:
2023
Object Size:
2,600 sq ft
Project Cost:
$17,000 – $21,000
Location:
Orleans, MA
Project – Shingle Roof & Siding Refresh in Mashpee, MA
Project Year:
2024
Object Size:
2,900 sq ft
Project Cost:
$16,000 – $22,000
Location:
Mashpee, MA
Project – Cedar Roof Restoration in Wellfleet, MA
Project Year:
2023
Object Size:
2,900 sq ft
Project Cost:
$22,000 – $28,000
Location:
Wellfleet, MA
Project – Full Exterior Renovation in Provincetown, MA
Project Year:
2024
Object Size:
3,200 sq ft
Project Cost:
$40,000 – $50,000
Location:
Provincetown, MA
Project – Synthetic Tile Roofing in Chatham, MA
Project Year:
2023
Object Size:
3,600 sq ft
Project Cost:
$30,000 – $38,000
Location:
Chatham, MA
Project – Gutter System Upgrade in Brewster, MA
Project Year:
2024
Object Size:
2,300 sq ft
Project Cost:
$4,000 – $6,000
Location:
Brewster, MA
Project – Deck & Siding Renovation in Dennis, MA
Project Year:
2024
Object Size:
2,700 sq ft
Project Cost:
$20,000 – $27,000
Location:
Dennis, MA
Project – Commercial Rubber Roof Installation in Hyannis, MA
Project Year:
2023
Object Size:
6,500 sq ft
Project Cost:
$28,000 – $36,000
Location:
Hyannis, MA
Project – Vinyl Siding Installation in Sandwich, MA
Project Year:
2024
Object Size:
2,500 sq ft
Project Cost:
$14,000 – $18,000
Location:
Sandwich, MA
Project – Cedar Shake Roof & Gutter Replacement in Falmouth, MA
Project year:
2023
Object size:
3,100 sq ft
Project cost:
$18,000 – $25,000
Location:
Falmouth, MA
Project – Asphalt Roof & Gutter Upgrade in Sandwich, MA
Project year:
2024
Object size:
2,800 sq ft
Project cost:
$9,000 – $13,000
Location:
Sandwich, MA
Project – Cedar Roofing & Gutters in Barnstable, MA
Project year:
2024
Object size:
2,800 sq ft
Project cost:
$12,000 – $16,000
Location:
Barnstable, MA
Project – Shingle roof and gutters replacement in Darien, IL
Project year:
2023
Object size:
3,400 sq
Project cost:
$10,000 - $15,000
Location:
Darien, IL
Take a look at our recent projects
See how we’ve transformed homes of all sizes and styles, and you’ll get an idea of the quality and craftsmanship that you can expect from Roofing & Siding of Cape Cod.
Before & After
Real projects. Real results. See how we transform homes — one job at a time.
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Contact us for a free estimate and start your journey towards a beautiful, durable home exterior.