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Welcome home to this charming 3-bedroom, 2-bath brick home offering comfort, convenience, and important updates already taken care of! Step inside to find beautiful new LVP flooring and original hardwood floors that bring warmth and character throughout the home. Major updates include a NEW METAL ROOF and NEW HVAC SYSTEM, giving you the peace of mind of knowing two of the biggest home expenses have already been addressed. The comfortable layout offers plenty of space for everyday living, while the fully fenced backyard provides the perfect space for pets, children, entertaining, or simply enjoying your own outdoor space. Located just minutes from downtown Cheraw, you’ll have convenient access to shopping, dining, schools, and everyday necessities while still enjoying the comfort of a residential neighborhood. If you’ve been looking for an affordable brick home with a new roof, new HVAC, beautiful flooring, and a fenced yard, this one is worth seeing in person! VIRTUALLY STAGED PHOTOS: Some interior photos have been virtually staged for illustrative purposes to help buyers envision the potential of the space. Furniture and/or décor shown in virtually staged images are digitally added and are not included with the property. Actual property condition, features, finishes, and dimensions may differ from the virtually staged images. Buyers and agents are encouraged to view the property in person.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1961
  • 0.31 Acre Lot
  • 137 days on Market

  • Bedrooms
    3
  • Bathrooms
    2
  • Year Built
    1961
  • Architectural Style
    Ranch
  • Construction Materials
    Brick Veneer
  • Living Area
    1364.0
  • Appliances
    Microwave, Range
  • Flooring
    Hardwood, Vinyl, Wood
  • Patio And Porch
    Porch
  • Cooling
    Central Air
  • Heating
    Central
  • Basement
    Crawl Space

  • Acres
    0.31
  • Water
    Public

  • Area
    CHERAW
  • County
    Chesterfield
  • City
    Cheraw
  • Neighborhood
    COUNTY
  • Zip Code
    29520
  • High School
    CHERAW HIGH
  • Middle School
    LONG MIDDLE
  • Elementary School
    CHERAW PRIMARY

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Frequently Asked Questions

How do I schedule a tour of 44 Windsor Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 44 Windsor Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 44 Windsor Dr?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 2 bath, listed for $159,900. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Cheraw, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 44 Windsor Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 44 Windsor Dr at around $910. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 44 Windsor Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Chesterfield County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 44 Windsor Dr?

In most cases, yes. Whether 44 Windsor Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Cheraw's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 44 Windsor Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Cheraw and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $159,900 with 1,364 sqft of space—that comes out to approximately $117 per square foot.

How long has this property been on the market?

44 Windsor Dr was listed on June 29, 2026, which means it's been on the market for 137 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1961, making it approximately 65 years old.

What is the lot size of this property?

44 Windsor Dr sits on a 0.31-acre lot, which is 13,504 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: CHERAW PRIMARY
  • Middle: LONG MIDDLE
  • High: CHERAW HIGH

Want to see how these schools compare? Check out our Chesterfield County School Guide to see ratings, reviews, and more for the schools in the area.

Is 44 Windsor Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, Pee Dee Realtor Association. All rights reserved.

Last Updated: November 13, 2026 at 01:06PM | Source: Pee Dee Realtor Association | MLS#: 2602676

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