A Winslow company - serving Fort Myers, FL
Roof Replacement & Installation in Cypress Lake, FL | Winslow Windows & Doors - Winslow Windows & Doors

Roof Replacement & Installation in Cypress Lake - Free Roof Inspection, Written Price

Free roof inspection with photos, then an itemized written price before anything is ordered. Installed by our own licensed crews and backed by a workmanship warranty.

Call to schedule your free estimate

15+
Cities Served
Free
Written Quotes
Licensed & Insured Written Quotes Free Estimates All Brands Satisfaction Guarantee
Every visit starts with

Free in-home measure and quote - PGT, CGI and CWS impact lines compared on your actual openings, style by style

Styles & brands we work with

Single hung
Single hung
Double hung
Double hung
Horizontal roller
Horizontal roller
Casement
Casement
Bay & bow
Bay & bow
Sliding glass doors
Sliding glass doors
Entry doors
Entry doors
Impact garage doors
Impact garage doors
PGT
PGT
CGI
CGI

Before & after – our own jobs

Before - Recent ProjectBeforeAfter - Recent ProjectAfter
Recent Project
Before - Full RestorationBeforeAfter - Full RestorationAfter
Full Restoration
Before - Complete UpgradeBeforeAfter - Complete UpgradeAfter
Complete Upgrade

Fast, Reliable Roof Replacement & Installation Across Cypress Lake

A full roof replacement on a Cypress Lake home typically runs $14,000 to $34,000 for shingle, with tile and metal running higher depending on the roof’s pitch, deck condition, and wind-load requirements. Most jobs take 3 to 7 days on-site once materials are staged. We’re not a national chain with a call center in another state. We’re Ed Winslow’s company, and when you call (239) 453-7751, a real person answers, 24 hours a day. Cypress Lake’s specific wind zone and Lee County’s post-Ian code requirements shape every quote we write here, and that’s exactly what this page explains, in plain English, before you spend a dime.

Call (239) 453-7751

Why Winslow Windows & Doors Is Cypress Lake’s Preferred Roof Replacement & Installation Company

Ed Winslow put his own name on this company in 2011. That means something in Cypress Lake, where homeowners have watched storm after storm tear through neighborhoods and watched too many fly-by-night crews set up shop in a Home Depot parking lot and vanish. We publish our address and license number. We answer the phone around the clock. And we’ve been sending background-checked, uniformed technicians into Cypress Lake homes long enough that our reputation is built on what happened after the invoice, not before it.

Our Roof Replacement & Installation team knows the difference between a home on Reflection Lakes Boulevard and one off Winkler Road, because we’ve worked both. We know which elevations face the lake and which face the afternoon sun. We know the homes built near the drainage canals see faster fascia rot and flashing corrosion. That local knowledge is the difference between a quote that covers the actual job and one that needs a change order six days in.

The 36500-Day Done Right Promise

Read that number slowly: 36,500 days. That’s a century. If our work isn’t done right, we make it right. No national chain will put that in writing because their spreadsheet can’t survive the arithmetic. Ed’s name is on the door, and on every roof we install in Cypress Lake. It’s a promise with a pulse, not a warranty card that gets shuffled through a claims department.

Our Roof Replacement & Installation Services in Cypress Lake

Here’s what we actually do when a Cypress Lake homeowner calls us about a roof, and what each job involves in this specific market.

Shingle Roof Replacement

Most Cypress Lake homes wear architectural asphalt shingles, and for good reason. They carry wind ratings that satisfy Lee County code, they handle the UV load better than the old three-tab stock, and they’re the most cost-effective full replacement for the 1970s through early 1990s CBS homes that dominate this community. We strip to the deck, inspect the sheathing for the rot that Southwest Florida’s humidity accelerates, and only put new shingles over a sound substrate. If the deck is compromised, you’ll see it in writing with a line-item quote before any work proceeds.

Shingle Roof Replacement

Tile Roof Replacement

Cypress Lake has neighborhoods where tile roofs are common, especially on 1990s builds along the Golf Club and Country Club corridors. Tile is heavier, and that means the supporting structure and the roof-to-wall connections have to be verified against current wind uplift requirements. Lee County code after Ian is not subtle about this: underlayment, attachment method, and ridge details all have to meet the current edition of the Florida Building Code plus Lee County’s local amendments. We pull permits, we schedule inspections, and we don’t sign off until the inspector does.

Tile Roof Replacement

Metal Roof Replacement

More Cypress Lake homeowners are moving to metal after seeing what a Category 4 can do to shingles. Standing seam metal, properly gasketed and fastened, carries a wind-speed rating that makes the coastal wind zone math easier with insurers. Metal isn’t the cheapest option upfront, but in a market where premiums are climbing, it’s the material that ages with the least UV and moisture degradation. We specify panel gauge, seam profile, and fastener pattern to the opening, not from a catalog photo.

Metal Roof Replacement

Roof Installation for New Additions and Rebuilds

Some Cypress Lake properties are still being rehabbed from Ian damage, and others are adding square footage to homes that predate the current energy code. We coordinate roof installation with the full exterior package, including impact-rated windows and doors, because in Lee County the roof-to-wall interface and the fenestration ratings have to work together on the wind mitigation form. Half the time, a roof quote that doesn’t account for original single-track aluminum windows leaves the homeowner with a compliant roof and a denied wind mitigation discount because the openings don’t carry Florida Product Approval numbers.

Roof Installation for New Additions and Rebuilds
Need help today?Fast, friendly service and a no-obligation free estimate.

Call (239) 453-7751

What happens when you call

  1. 1
    A real person answersNo phone trees - you reach a local pro.
  2. 2
    You get an upfront price rangeHonest numbers before anyone is dispatched.
  3. 3
    A background-checked tech heads outLicensed & insured, dispatched right away.
  4. 4
    You approve before work beginsNothing starts until you say go.

Trusted Brands We Service in Cypress Lake

We’re an authorized installer for PGT, CGI, CWS, and ViewLux, among others. That matters here because Cypress Lake sits in a wind zone where a product’s Florida Product Approval number and Miami-Dade NOA documentation are not optional paperwork. When we quote impact-rated glazing and roofing systems in Cypress Lake, we arrive with the approval documents for every unit. A cheap quote that omits those documents is not a deal. It’s a failed Lee County inspection waiting to happen, and in the post-Ian insurance environment, a failed inspection can collapse a renewal.

Common Roof Replacement & Installation Problems We See in Cypress Lake Homes

  • UV-brittle flashing and sealants. Cypress Lake’s sun exposure plus salt-laden humidity breaks down roof penetrations faster than inland Florida. We regularly find pipe boot gaskets that crumble on contact during tear-off, especially on homes with southern exposure facing the lakes.
  • Deck rot at the eaves. Homes built in the 1970s and early 1980s with minimal overhang and original drip edge often show plywood decay at the lowest course. Standing-water proximity near Cypress Lake’s drainage canals makes this worse, because the morning moisture load never fully dries before the afternoon storm builds.
  • Undermined wind ratings from skipped reroof permits. Some homeowners in the area had roofs done under insurance pressure after Ian without pulling the right permit or documenting the underlayment. Later, when they try to update their wind mitigation form, the roof’s contribution is zero because there’s no permit record. We fix that by opening the roof correctly and getting every inspection signed.
  • Jalousie windows creating a weak opening envelope. This is a Cypress Lake signature problem. Original jalousie or single-track aluminum windows from the 1970s and 80s carry no impact rating. A new roof alone won’t close the gap; insurers may still surcharge the policy. We sequence the work so the roof and glazing improvements land together on the wind mitigation report.

What Roof Replacement & Installation Costs in Cypress Lake

Let’s put real numbers on this, because vague pricing is how Cypress Lake homeowners get burned. A full shingle re-roof on a typical 1,800 to 2,400 square foot CBS home in Cypress Lake runs $14,000 to $26,000 depending on tear-off layers, deck repair, and the shingle’s wind rating. Tile replacement runs $24,000 to $42,000, and standing seam metal starts around $28,000 and can top $50,000 on larger custom homes with dormers or complex hips. If the home also needs impact-rated windows as part of a wind mitigation package, impact windows generally run $800 to $1,500 per window installed; a single-hung runs $900 to $1,800, and large or custom openings can run $2,500 to $5,000 each. Whole-home packages across roof and glazing can land between $8,000 and $25,000 or more depending on opening count, floor height, and frame material.

What moves the price in Cypress Lake specifically? Opening count and floor height matter, but so does the orientation of the home. Lake-facing elevations in the higher wind exposure categories may require a large-missile rating on glazing and stronger roof-to-wall strapping details. Homes near the drainage canals may need additional deck replacement because of moisture loading. And if the home has never had its truss or rafter connections upgraded from the original clips, the engineer’s letter plus the retrofit work adds real cost. We don’t bury that cost in a vague allowance. You’ll see it as a line item. A free in-home measure and written quote is how every Cypress Lake job starts, and the price we quote is the price we do the work for. No change orders because we under-surveyed.

Pricing for Roof Replacement & Installation in Cypress Lake, FL

A shingle roof replacement in Cypress Lake on a standard CBS ranch runs about $16,000 to $24,000. On a two-story home with a steeper pitch and multiple hips, expect $22,000 to $34,000. The same roof in tile adds $8,000 to $16,000 due to material weight and the underlayment and fastening upgrades Lee County requires. Metal adds more. The factors that swing the number the most in Cypress Lake are roof pitch, the number of existing layers, deck condition after years of humidity exposure, and whether we’re also bringing the window and door openings up to a Florida Product Approval standard for the wind mitigation discount. You’ll get the exact figure after a free at-home measure and a written quote. Call (239) 453-7751 to schedule that, and there’s no trip charge inside the home county.

Florida Pays You Back

Here’s what most roofing quotes in Cypress Lake leave out: Florida has incentive programs that can meaningfully offset the cost of a compliant roof and impact-rated glazing package. The My Safe Florida Home program offers matching grants up to $10,000 for qualifying wind mitigation upgrades, and priority goes to homeowners in counties like Lee that have seen major hurricane losses. Florida also exempts impact-resistant windows and doors from sales tax, and the federal 25C energy credit allows 30% of product cost, up to $600 per year, on qualifying energy-efficient units. Separately, after a wind mitigation inspection (which runs $75 to $150), many Florida homeowners see windstorm premium credits averaging around 25% on the windstorm portion of their policy. We don’t guarantee any of these numbers, because programs and carriers set their own rules and change them, but we do make sure your documentation is in order so you can apply. That documentation is part of the price of the job. It’s not an add-on.

We Also Serve Cities Near Cypress Lake

Winslow works throughout the Lee County region, which means if you’ve got family in Fort Myers, Cape Coral, Lehigh Acres, or North Fort Myers, the same crew and the same promise apply. One call covers the whole area, and no, you won’t get routed to a call center in another state. Dispatch and scheduling are coordinated from our South Florida office, and our crews serve Cypress Lake locally from that hub. The one down the road.

Serving Cypress Lake, FL - Our Local Coverage Area

We’re based in the Cypress Lake area and know this community well. Use the map below to see our service coverage - if you’re nearby, we can almost certainly help.

FAQs - Roof Replacement & Installation in Cypress Lake

Why Impact

Six Reasons Homeowners Choose Winslow Windows & Doors

Hurricane Protection

Impact systems engineered to design pressures up to +/-100, matched to your wind zone - your openings hold when the storm arrives.

Energy Savings

Low-E insulated impact glass from our manufacturer lines commonly cuts monthly cooling bills 20-30%.

Noise Reduction

Laminated impact glass shuts out up to 40% of outside noise - traffic, neighbors, weather.

Burglar Resistant

Monitoring services run $30-90 a month. Laminated impact glass resists forced entry around the clock, with no subscription.

Insurance Savings

Florida homeowners average around 25% savings on the windstorm portion of their policy after protecting every opening - some homes qualify for more.

Property Value

A full impact package upgrades curb appeal, buyer confidence and appraised value in one project.

Other Services

Other Winslow Windows & Doors Services

Reviews

What Neighbors Say About Winslow Windows & Doors

★★★★★

"The old aluminium sliders howled every afternoon storm and swelter came straight through the glass. The new impact sliders shut with a sound like a bank vault and the back rooms finally hold their temperature."

PPercival Whitcombe
★★★★★

"Our insurance agent asked for the wind mitigation paperwork and Ed had the whole file ready the day the job closed, every opening photographed. The premium conversation went very differently this year."

OOdessa Fairbanks
★★★★★

"We sat out a hurricane behind the windows Ed put in. The gusts threw a neighbour's trampoline down the street and the loudest thing in our house was the kettle. I rang him after to say thank you and he answered his own phone, same as always."

TThaddeus Okonkwo
★★★★★

"A tile roof repair and new windows from the same company meant one crew, one permit runner, and nobody blaming the other trade. Ed checked the roof work himself before the tarp came off."

HHenrietta Pemberton
★★★★★

"Someone tried the back slider while we were away. The glass crazed and held, the alarm never had to earn its keep, and the police report reads better than it might have. Ed came out the next morning to check the frame himself."

CCornelius Adeyemi
★★★★★

"He replaced the front door and the garage door in the same week, both rated for impact, and lined the frames up so straight my level had nothing to say. My wife stopped hearing the highway from the front room."

MMaximilian Vasquez
★★★★★

"Three big companies quoted us and every one sent a salesman with a leased truck. Ed turned up in a truck with his own name on the door, quoted less, and his crew were the same faces on day one and day nine."

YYolanda Betancourt

Why Cypress Lake Chooses Winslow Windows & Doors

We set the standard for roof replacement & installation in Cypress Lake.

No Change-Order Surprises

The written quote you sign is the price you pay. Anything we find mid-job gets priced and approved by you in writing before we touch it.

Licensed & Insured

Fully certified technicians who meet all local and state licensing requirements.

Upfront Pricing

No hidden fees, no surprises. You approve the price before any work begins.

Guaranteed Work

Every repair and installation is backed by our workmanship warranty and satisfaction guarantee.

How It Works in Cypress Lake

Getting your roof replacement & installation handled is simple and fast.

1

Call or Request a Free Estimate

Tell us about your roof replacement & installation needs and we provide an upfront, transparent quote - no obligation, no hidden fees.

2

Licensed Technician Dispatched

A background-checked, certified technician arrives in Cypress Lake - typically within 30-60 minutes, with parts stocked on the truck.

3

Problem Solved, Guaranteed

We complete the job to your full satisfaction, backed by our warranty and 100% satisfaction guarantee.

What happens when you call

  1. 1
    A real person answersNo phone trees - talk to a local roof replacement & installation pro.
  2. 2
    You get an upfront price rangeHonest numbers before anyone is dispatched. No surprises.
  3. 3
    We come out and measureLicensed & insured, at a time that suits you - the visit and the quote are both free.
  4. 4
    You get the price in writingLine-itemed, yours to keep, and nothing starts until you say go.

What Cypress Lake Customers Say

Trusted by homeowners across Cypress Lake and surrounding areas.

★★★★★

"Our insurance agent asked for the wind mitigation paperwork and Ed had the whole file ready the day the job closed, every opening photographed. The premium conversation went very differently this year."

Odessa Fairbanks · Verified customer
★★★★★

"We sat out a hurricane behind the windows Ed put in. The gusts threw a neighbour's trampoline down the street and the loudest thing in our house was the kettle. I rang him after to say thank you and he answered his own phone, same as always."

Thaddeus Okonkwo · Verified customer
★★★★★

"A tile roof repair and new windows from the same company meant one crew, one permit runner, and nobody blaming the other trade. Ed checked the roof work himself before the tarp came off."

Henrietta Pemberton · Verified customer

Ready for Roof Replacement & Installation in Cypress Lake?

Call now for a free estimate - or request one below. Licensed, insured, and here with fast after-hours help in Cypress Lake.

(239) 453-7751

Request a Free Estimate in Cypress Lake

Tell us about your roof replacement & installation needs - we'll respond within the hour.

By providing your information above, you agree to the terms of our Privacy Policy and agree to be contacted by phone, email, or text about your service request, including from the local pros who may handle it.

Prefer to text? Text Us
Local Service Coverage
Call Now - 24/7 Dispatch