25 Best Window Replacement Companies in Sidney, OH (Feb 2023)
Window Companies Near Me

Are you thinking about replacing your windows? Our list of the top window installation companies can help you choose the right one for you.

We analyzed all the top window installers in Sidney and selected the top 25 based on:

  • Customer reviews
  • Window replacement expertise
  • Popularity with home-owners like you
EcoWatch Local Advisors

By EcoWatch Local Advisors

Updated January 12, 2023

Why you can trust EcoWatch

Our panel of energy experts work tirelessly to create unbiased reviews and informative content to help homeowners make educated decisions. No other windows site has covered energy efficiency and sustainability as long as EcoWatch, which means we're going to help you find windows replacements that will save on your energy bill and put more money back in your wallet.

Whether you're updating for style or have damaged windows, windows play a important role in conserving your home's energy. Drafty windows can make your home uncomfortable in the summer or winter.

Installing new, efficient windows on your property can help you save money each month on your electric bills — and you can help the environment as well.

So if you're building a new home, renovating or replacing your windows in Sidney, you've found the best place to get started.

Best Affordability

Window World

★★★★★
4.5

  • Great industry reputation
  • Lifetime warranty
  • Low prices relative to competitors
  • Quality of service will depend on your area

Best Overall

Renewal by Andersen

★★★★★
4.5

  • Manufactures products in-house
  • Award-winning company
  • Great industry reputation
  • More expensive than competition

Best for Residential Windows

Window Nation

★★★★★
4

  • Wide variety of products and services
  • Custom designs
  • Award-winning company
  • Installation not covered by warranty

Best Window Replacement Companies in Sidney

The EcoWatch team evaluated dozens of installers across the country to find the top window companies for our readers. We assessed the companies on their energy-efficient offerings, customer service, coverage area, price, local experience and more.

Window World logo
FAST QUOTE
as little as 30 seconds
Best Affordability

Window World

★★★★★
BBB Rating: A+
Locations: Nationwide
Founded: 1995
Pros:
  • Pros icon Great industry reputation
  • Pros icon Lifetime warranty
  • Pros icon Low prices relative to competitors
Cons:
  • Pros icon Quality of service will depend on your area

Window World is the largest window replacement company in the country, known for its vinyl windows and affordability. This provider has 27 years of experience in the window installation business, and it has proved to be one of the most reputable companies in Sidney.

It is certified by the Environmental Protection Agency (EPA) and Energy Star and supports charities like St. Jude Children’s Research Hospital.

Energy Efficiency of Window World Windows

There are a wide variety of window types that Window World offers, some of which are Energy Star products. Its high-performance Low-E (low-emissivity) coatings and argon gas insulation offer exceptional efficiency and performance for any home.

How much does Window World cost in Sidney?

Even though prices are not readily available on Window World's website, it's known for offering some of the most affordable window installations around. You can ask for a free quote on its website for more information about the cost.

Renewal by Andersen logo
FAST QUOTE
as little as 30 seconds
Best Overall

Renewal by Andersen

★★★★★
BBB Rating: A
Locations: Nationwide
Founded: 1995
Pros:
  • Pros icon Manufactures products in-house
  • Pros icon Award-winning company
  • Pros icon Great industry reputation
Cons:
  • Pros icon More expensive than competition

Renewal by Andersen is a subsidiary of the Andersen Corporation, a major manufacturer of windows and doors. Andersen has about 27 years of experience in the industry, and it currently serves nearly every state except Mississippi and West Virginia. Its reputation is backed by many positive reviews on customer review websites.

If you're looking for a company that uses in-home estimates and advanced digital tools to help you plan and visualize your project before getting started, Andersen may be the right company for you.

Energy Efficiency of Renewal by Andersen Windows

There are a wide variety of window types that Renewal by Andersen offers, some of which are Energy Star products. A handful of windows manufactured by the Andersen corporation were awarded Energy Star’s “Most Efficient” in 2021, and Andersen was named Energy Star’s Partner of the Year in 2019.

How much does Renewal by Andersen cost in Sidney?

Although prices are not readily available on Andersen's website, based on customer feedback, you can expect to pay anywhere between $750 to $1,250 per window for an installation with Andersen. Requesting a free quote on its website is the best way to get more accurate pricing information.

Window Nation logo
FAST QUOTE
as little as 30 seconds
Best for Residential Windows

Window Nation

★★★★★
BBB Rating: A
Locations: Regional
Founded: 2006
Pros:
  • Pros icon Wide variety of products and services
  • Pros icon Custom designs
  • Pros icon Award-winning company
Cons:
  • Pros icon Installation not covered by warranty

Window Nation provides the best residential windows in Sidney. Window Nation has around 16 years of experience in the window installation industry. Its reputation is backed by a considerable amount of positive reviews from customers online.

It gives customers the opportunity to view products and to speak to a representative in person in its showrooms.

Energy Efficiency of Window Nation Windows

Window Nation carries some Energy Star windows, but note that not all its windows are energy-efficient, so be sure to mention that you want Energy Star windows when inquiring. Each product has windowpanes coated with a Low-E (low emissivity) glaze that prevents damaging UV rays from heating your home. Plus, the spaces between double- and triple-pane windows are filled with argon gas that’s been proven to improve home insulation.

How much does Window Nation cost in Sidney?

Window Nation doesn't have any cost information available on its website, but based on customer feedback, you can expect to pay between $300 and $525 per window installed, making it a more affordable option compared to competitors. Getting a free quote on its website is the best way to know for sure.

Universal Windows Direct logo
FAST QUOTE
as little as 30 seconds
Best Warranty

Universal Windows Direct

★★★★★
BBB Rating: A
Locations: Nationwide
Founded: 2002
Pros:
  • Pros icon Makes charitable contributions
  • Pros icon Manufactures products in-house
  • Pros icon Wide variety of products and services
  • Pros icon Lifetime warranty
Cons:
  • Pros icon Limited service area
  • Pros icon Some installations carried out by third-party contractors
  • Pros icon Quality of service will depend on your area

Universal Windows Direct is a company that has grown immensely since its inception in 2002, and now has several franchise dealers nationwide. Universal has over 20 years of experience in the industry, and it currently serves 27 states nationwide. The provider has hundreds of glowing reviews from customers on online review websites.

If you're looking for a company that has an industry-leading warranty covering products, parts and workmanship for life, Universal may be the right company for you.

Energy Efficiency of Universal Windows Direct Windows

The company offers energy-efficient UniShield brand windows. According to its website, UniShield window packages have higher gas fill rates and longer gas retention than most other brands on the market, and they are Energy Star products. Not all of Universal's windows are Energy Star certified, so make sure you mention that you want Energy Star windows when inquiring.

How much does Universal Windows Direct cost in Sidney?

Universal does not mention prices on its website, but installations typically range from $225 to $425 per window based on customer feedback. That makes Universal Windows Direct more of a budget-friendly option for window repair and replacements. You can request a free quote on its website for more information about the cost.

We aim to remain unbiased and transparent by including pros and cons for every installer. Additionally, any partnerships do not influence our rankings.

More Window Replacement Companies in Sidney

ImproveIt Home Remodeling

Dayton, OH
4.1
★★★★★
  • Pros icon Consistent Workmanship
  • Pros icon Arrives on Time
  • Pros icon Price Transparency
  • Pros icon Educational Website

Services Offered

  • Service icon Glass Showers
  • Service icon Residential Windows
  • Service icon Architectural Glass
  • Service icon Custom Windows
  • Service icon Double-Hung

Website: https://www.improveitusa.com/locations/dayton/
Address: 7200 Poe Ave Suite 102, Dayton, OH 45414
Phone: (937) 204-1551

Pella Windows & Doors

Lima, OH
4.1
★★★★★
  • Pros icon Free Quotes
  • Pros icon Award-Winning
  • Pros icon No-Hassle Pricing
  • Pros icon Helps Educate Customers

Services Offered

  • Service icon Residential Windows
  • Service icon Architectural Glass
  • Service icon Fast Delivery
  • Service icon Custom Windows
  • Service icon Business Windows
  • Service icon Double-Hung
  • Service icon Sliding Glass
  • Service icon Bay Windows

Website: http://www.pella.com/
Address: 2550 W Breese Rd, Lima, OH 45806
Phone: (419) 222-1911

Thrush & Son: Complete Home Improvement Company

Brookville, OH
4.0
★★★★★
  • Pros icon Locally Recognized for Quality
  • Pros icon Good Customer Service
  • Pros icon Reliable Service
  • Pros icon No-fee Quotes

Services Offered

  • Service icon Fast Delivery
  • Service icon Tempered Glass
  • Service icon Custom Windows
  • Service icon Business Windows
  • Service icon Double-Hung
  • Service icon Sliding Glass

Website: https://www.thrushandson.com/
Address: 115 Jefferson St, Brookville, OH 45309
Phone: (888) 349-8889

Home Services at The Home Depot

Springfield, OH
3.4
★★★★★
  • Pros icon Educational Website
  • Pros icon Consistent Workmanship
  • Pros icon No-fee Quotes
  • Pros icon No-Hassle Pricing

Services Offered

  • Service icon Residential Windows
  • Service icon Fast Delivery
  • Service icon Custom Window Designs
  • Service icon Double-Hung
  • Service icon Sliding Glass

Website: https://www.homedepot.com/l/Springfield-OH/OH/Springfield/45504/3867/services
Address: 1880 N Bechtle Ave, Springfield, OH 45504
Phone: (937) 265-8815

All Service Glass

Lima, OH
3.4
★★★★★
  • Pros icon Free Quotes
  • Pros icon Excellent Customer Service
  • Pros icon Educational Website
  • Pros icon No-Hassle Pricing

Services Offered

  • Service icon Glass Showers
  • Service icon Residential Windows
  • Service icon Custom Window Designs
  • Service icon Business Windows
  • Service icon Double-Hung

Website: http://www.allservglass.com/
Address: 4511 Elida Rd, Lima, OH 45807
Phone: (419) 227-0027

Window Depot USA of Dayton, OH

Dayton, OH
3.3
★★★★★
  • Pros icon Price Transparency
  • Pros icon Locally Recognized for Quality
  • Pros icon Free Quotes
  • Pros icon Helps Educate Customers

Services Offered

  • Service icon Custom Window Designs
  • Service icon Sliding Glass
  • Service icon Double-Hung

Website: https://windowreplacementdayton.com/
Address: 3562 Intercity Dr, Dayton, OH 45424
Phone: (937) 240-1900

Window Depot

Dayton, OH
3.1
★★★★★
  • Pros icon Educational Website
  • Pros icon Good Customer Service
  • Pros icon Free Quotes
  • Pros icon Price Transparency

Services Offered

  • Service icon Energy-Efficient Options
  • Service icon Custom Windows
  • Service icon Double-Hung
  • Service icon Sliding Glass
  • Service icon Bay & Bow Windows

Website: http://daytonwindows.com/
Address: 700 Brandt St, Dayton, OH 45404
Phone: (937) 278-6600

Schaefer and Company

Troy, OH
3.1
★★★★★
  • Pros icon Price Transparency
  • Pros icon Free Quotes
  • Pros icon Consistent Workmanship
  • Pros icon Excellent Customer Service

Services Offered

  • Service icon Aluminum Window Frames
  • Service icon Energy-Efficient Options
  • Service icon Full-Service Installations
  • Service icon Custom Windows

Website: http://www.schaeferandcompany.com/
Address: 3205 S Co Rd 25A, Troy, OH 45373
Phone: (937) 339-2638

Simply Windows & Doors

Dayton, OH
3.1
★★★★★
  • Pros icon Good Customer Service
  • Pros icon Price Transparency
  • Pros icon Educational Website
  • Pros icon Free Quotes

Services Offered

  • Service icon Residential Windows
  • Service icon Architectural Glass
  • Service icon Custom Windows
  • Service icon Double-Hung
  • Service icon Sliding Glass

Website: https://www.simplywindowsdayton.com/
Address: 3321 N Dixie Dr, Dayton, OH 45414
Phone: (937) 253-6000

Moeller Door & Window

St Henry, OH
3.1
★★★★★
  • Pros icon No-fee Quotes
  • Pros icon Excellent Customer Service
  • Pros icon No-Hassle Pricing
  • Pros icon Helps Educate Customers

Services Offered

  • Service icon Residential Windows
  • Service icon Custom Window Designs
  • Service icon Aluminum Window Frames
  • Service icon Commercial Windows
  • Service icon Sliding Glass

Website: http://www.moellerdoorandwindow.com/
Address: 5970 OH-119, St Henry, OH 45883
Phone: (419) 925-4748

Moeller Door and Window -Sidney Oh

St Henry, OH
3.1
★★★★★
  • Pros icon Educational Website
  • Pros icon Price Transparency
  • Pros icon Good Customer Service
  • Pros icon Free Quotes

Services Offered

  • Service icon Residential Windows
  • Service icon Custom Windows
  • Service icon Aluminum Window Frames
  • Service icon Business Windows
  • Service icon Sliding Glass

Website: http://www.moellerdoorandwindow.com/
Address: 5970 St Rt 119, St Henry, OH 45883
Phone: (937) 497-0600

Modern Builders Supply, Inc. Lima Branch

Lima, OH
3.1
★★★★★
  • Pros icon Dependable Service
  • Pros icon No-Hassle Pricing
  • Pros icon Helps Educate Customers
  • Pros icon Excellent Customer Service

Services Offered

  • Service icon Residential Windows
  • Service icon Fast Delivery
  • Service icon Custom Window Designs
  • Service icon Aluminum Window Frames
  • Service icon Commercial Windows

Website: http://modernbuilderssupply.com/branches/oh/lima.html
Address: 1245 Neubrecht Rd, Lima, OH 45801
Phone: (419) 224-4627

Belle Exteriors

Fairborn, OH
3.1
★★★★★
  • Pros icon Free Quotes
  • Pros icon Price Transparency
  • Pros icon Consistent Workmanship
  • Pros icon Good Customer Service

Services Offered

  • Service icon Custom Windows
  • Service icon Residential Windows

Website: http://www.belle-exteriors.com/
Address: 415 W Dayton Dr, Fairborn, OH 45324
Phone: (937) 999-9596

Thrush & Son of Troy: Complete Home Improvement Company

Troy, OH
3.1
★★★★★
  • Pros icon No-Hassle Pricing
  • Pros icon Dependable Service
  • Pros icon No-fee Quotes
  • Pros icon Excellent Customer Service

Services Offered

  • Service icon Custom Window Designs
  • Service icon Commercial Windows

Website: http://www.thrushandsonoftroy.com/
Address: 10 N Market St, Troy, OH 45373
Phone: (937) 339-5136

Champion Replacement Windows of Dayton

Huber Heights, OH
3.0
★★★★★
  • Pros icon Excellent Customer Service
  • Pros icon Award-Winning
  • Pros icon Price Transparency
  • Pros icon Reliable Service

Services Offered

  • Service icon Custom Window Designs
  • Service icon Sliding Glass
  • Service icon Double-Hung

Website: https://www.championwindow.com/Dayton/
Address: 6258 Executive Blvd #400, Huber Heights, OH 45424
Phone: (937) 458-3758

Affordable Glass & Mirror

Dayton, OH
3.0
★★★★★
  • Pros icon Helps Educate Customers
  • Pros icon Reliable Service
  • Pros icon No-Hassle Pricing
  • Pros icon Excellent Customer Service

Services Offered

  • Service icon Custom Windows
  • Service icon Sliding Glass
  • Service icon Double-Hung

Website: https://www.affordableglassdayton.com/
Address: 7210 Chambersburg Rd, Dayton, OH 45424
Phone: (937) 236-1481

Elevated Roofing & Siding

Troy, OH
3.0
★★★★★
  • Pros icon Helps Educate Customers
  • Pros icon Excellent Customer Service
  • Pros icon Reliable Service
  • Pros icon Price Transparency

Services Offered

  • Service icon Custom Window Designs
  • Service icon Residential Windows
  • Service icon Commercial Windows

Website: http://elevated-roofing.com/
Address: 405 Public Square Suite 241, Troy, OH 45373
Phone: (937) 248-1362

McIntyre Glass

Vandalia, OH
2.8
★★★★★
  • Pros icon No-Hassle Pricing
  • Pros icon Educational Website
  • Pros icon Good Customer Service

Services Offered

  • Service icon Glass Showers
  • Service icon Residential Windows
  • Service icon Custom Window Designs
  • Service icon Aluminum Window Frames
  • Service icon Business Windows

Website: http://www.mcintyreglass.com/
Address: 3700 Lightner Rd, Vandalia, OH 45377
Phone: (937) 771-6004

Ginter Siding and Windows

Englewood, OH
2.8
★★★★★
  • Pros icon Price Transparency
  • Pros icon Free Quotes
  • Pros icon Award-Winning

Services Offered

  • Service icon Double-Hung
  • Service icon Full-Service Installations
  • Service icon Custom Windows
  • Service icon Aluminum Window Frames
  • Service icon Energy-Efficient Options

Website: http://ginter-siding-and-windows.us/
Address: 1 S Main St, Englewood, OH 45322
Phone: (937) 475-4565

Wissman Window & Door Plus More

Greenville, OH
2.8
★★★★★
  • Pros icon No-Hassle Pricing
  • Pros icon Excellent Customer Service
  • Pros icon No-fee Quotes

Services Offered

  • Service icon Residential Windows
  • Service icon Custom Windows
  • Service icon Aluminum Window Frames
  • Service icon Commercial Windows
  • Service icon Sliding Glass

Website: http://www.wissmanwindowdoor.com/
Address: 326 S Broadway St, Greenville, OH 45331
Phone: (937) 547-3365

Sunlight Windows LLC

Bellefontaine, OH
2.8
★★★★★
  • Pros icon Good Customer Service
  • Pros icon Price Transparency
  • Pros icon Dependable Service
  • Pros icon Timely Service

Services Offered

  • Service icon Custom Window Designs
  • Service icon Residential Windows

Website: http://www.sunlightwindows.us/
Address: 8164 US-68 North, Bellefontaine, OH 43311
Phone: (937) 582-1414

Andrews Services, LLC

Huber Heights, OH
2.8
★★★★★
  • Pros icon Excellent Customer Service
  • Pros icon Price Transparency
  • Pros icon Reliable Service
  • Pros icon No-fee Quotes

Services Offered

  • Service icon Custom Windows
  • Service icon Residential Windows

Website: http://andrewsservices.net/
Address: 7125 Old Troy Pike, Huber Heights, OH 45424
Phone: (937) 422-1260

IDW Window & Roof Cleaning

Elida, OH
2.7
★★★★★
  • Pros icon Helps Educate Customers
  • Pros icon Free Quotes
  • Pros icon Excellent Customer Service
  • Pros icon Price Transparency

Services Offered

  • Service icon Custom Window Designs
  • Service icon Residential Windows
  • Service icon Commercial Windows

Website: http://idowindowsllc.com/
Address: 220 S Greenlawn Ave, Elida, OH 45807
Phone: (419) 339-3999

Buckeye Door Sales

Dayton, OH
2.6
★★★★★
  • Pros icon Educational Website
  • Pros icon Price Transparency
  • Pros icon Gives to charity
  • Pros icon Good Customer Service

Services Offered

  • Service icon Custom Window Designs

Website: https://www.buckeyedoorsales.com/
Address: 8640 N Main St, Dayton, OH 45415
Phone: (937) 529-6107

All-Seal Home Improvement, LLC

Dayton, OH
2.6
★★★★★
  • Pros icon Price Transparency
  • Pros icon Free Quotes
  • Pros icon Good Customer Service

Services Offered

  • Service icon Custom Windows
  • Service icon Energy-Efficient Options
  • Service icon Business Windows
  • Service icon Sliding Glass

Website: http://www.allseal.com/
Address: 6104 Poe Ave, Dayton, OH 45414
Phone: (937) 890-9484

How Installing Energy-Efficient Windows in Sidney Saves You Money

When you upgrade to energy-efficient windows, you may see several perks, such as:

  • Decrease your carbon footprint: You can reduce your indirect greenhouse gas emissions by about 12% after you install Energy Star certified windows. In Sidney, that's about 525 pounds per year on average.
  • Protect your valuables: The low-emissivity coatings on many energy-efficient windows help prevent the fading of your floors, carpets and furniture by filtering out UV rays.
  • Save on electricity bills: Once you upgrade to energy-efficient windows, you can see a reduction in your bills by about 12% because you'll require less energy to heat or cool your home.
  • Protect your investment: The older your home is, the more likely it is that switching to energy-efficient windows will benefit you. Older homes usually have windows that are outdated, leaky or potentially even damaged in some way. Updating your windows could help increase the value of your home if you decide to sell.

Estimated Cost of Window Replacement in Sidney

Each window replacement company offers various services and has different costs based on a few factors.

How Much Do New Windows Cost?

Generally, Sidney homeowners can expect their window replacements to range from $250 to $1,200. The most common installations sit at approximately $600. This is due to the fact that the cost of window installations are based on a variety of factors specific to your home, like the size, material and number of windows you need to replace, as well as where your property is located.

It's also worth keeping in mind that energy-efficient windows will usually cost more initially, but Energy Star estimates that switching out the windows on your Sidney home can mean an average energy savings of $236 to $319 a year for single-pane window replacement, or between $87 to $126 a year for double-pane windows. How much you'll save by switching to energy-efficient windows depends on your local climate, energy rates and other factors unique to your home.

We advise requesting free quotes from multiple window installation companies to find the one that works best for you.

What Services do Window Installers Offer?

There are generally two kinds of window installation services: full-frame and pocket installations.

Full-frame installations require replacing the whole window — the sill, frame, trim and all. These are typically done when you want to change the style of your window or when it has significant rot or deterioration. Full-frame installations involve more time and labor and will increase overall costs. A pocket installation entails installing a new window without replacing the frame. This means instead of removing the whole unit and rebuilding it, the installer will just slide the replacement window (also called a retrofit or insert window) into the frame.

Your window replacement company will be able to help you figure out what's best for your needs. In Sidney, the decision will mostly depend on how old your windows are and if there's any damage. Wood can decay if not properly maintained over the years, so it's good to have a professional assess your frames and window sills.

Best Affordability

Window World

★★★★★
4.5

  • Great industry reputation
  • Lifetime warranty
  • Low prices relative to competitors
  • Quality of service will depend on your area

Best Overall

Renewal by Andersen

★★★★★
4.5

  • Manufactures products in-house
  • Award-winning company
  • Great industry reputation
  • More expensive than competition

Best for Residential Windows

Window Nation

★★★★★
4

  • Wide variety of products and services
  • Custom designs
  • Award-winning company
  • Installation not covered by warranty

How We Choose the Best Window Installers in Sidney

EcoWatch reviews are different from other reviews, as we're examining these companies through a sustainability lens. We have reviewed the best window replacement companies in Sidney mostly based on energy efficiency, as the most sustainable option also benefits homeowners in many ways. Energy-efficient windows can cut your energy bills by hundreds of dollars. Along with energy efficiency, our rating methodology takes the following factors into consideration:

Service Area

Since this is a guide for Sidney, we gave more points to companies that provide services to the city. There are certainly reputable providers that didn't make the cut because they wouldn't be able to serve homeowners in Sidney.

Work Quality

We're certain that you're not looking for a company to do a shoddy job installing windows. We've vetted each installer included in our guide to make sure its technicians are well-qualified and that the company has received a lot of positive customer feedback to vouch for its service.

Customer Reviews

Another self-explanatory yet very important review factor is customer feedback. If the majority of customers don't have good feedback about their service from a certain installer, it won't be featured on EcoWatch.

Cost

Cheaper windows don't necessarily mean better windows, but we know many of our readers want to keep costs low when possible. When analyzing providers' prices, we gave higher points to companies with reasonable prices and accessible financing rather than "cheaper" services.

Warranty

Protecting your investment in new windows is important to many homeowners. For that reason, window installation companies that offer lengthy warranties for products, parts and labor rank higher with EcoWatch.

Years of Experience

Last but not least, we like to see companies that have a proven track record in the industry. Window installation companies that have more experience will earn higher rankings by our standards. We like to see at least ten years of experience.

Sidney, OH Window Replacement FAQs

What is the average cost to replace windows in a home?

The average cost of installing a window can range from $450 to $650. There are many factors that affect the cost, such as local labor costs, the number of windows, your property's location, how energy-efficient the windows are, the materials used in designing the windows and styles and sizes of windows.

What are the most common types of replacement windows?

The most common types of windows for homes include: picture windows, transom windows, casement windows, awning windows, double-hung and single-hung windows, bay windows and slider windows.

What do window installation companies do?

Window installers travel to your home to remove your old windows and replace them with new ones. Some providers install products sold by other companies, whereas others are both manufacturers and installation companies combined. The installer will also clean up after the installation is complete.

What time of year is the best time to replace my windows?

Replacement windows can be installed any time of the year, but warmer weather is typically better. No matter when you install them, the contractors will take steps to ensure that too much hot or cold air doesn't get into the home, so the temperature outside isn't necessarily a big factor. What's most important is that the weather should be dry.

Should I replace all my windows at once?

If you're upgrading your windows because of energy-efficiency, replacing all of the windows at the same time is the only way to see a noticeable difference. However, if you have just a few windows that are damaged or leaky, you can replace just those.

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