South Windermere

South Windermere is a perfect solution for people looking to be close to downtown without the luxury price tag that usually accompanies Downtown Charleston real estate. Located near the neighborhoods of Windermere, Byrnes Down, Wappoo Heights and The Crescent, South Windermere offers both new and old homes in historic West Ashley SC. You’ll find a number of one-story cottage and two story brick homes with that early to mid-1900’s feel, even if they are new constructions. Many people look to South Windermere because a number of homes offer more square footage and larger yards than other subdivisions nearby.

If you’d like to explore this subdivision, contact me, Marshall Walker. I’ll be happy to show you everything that awaits you in South Windermere.

Modify Search Criteria
Displaying results 1-21 of 231
46 Photos 92 Chadwick Drive Charleston, SC 29407

92 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 25002332 / Active Contingent
3 br, 2 ba, 1 Half Bath, 3700 Sqft

TRUE DEEP WATER just minutes from downtown Charleston! Live in the prestigious South Windermere neighborhood, where this fully renovated mid-centur... 

More Details Compare

$3,850,000
Provided courtesy of The Cassina Group
34 Photos Sold 63 Chadwick Drive Charleston, SC 29407

63 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24030355 / Sold
5 br, 3 ba, 1 Half Bath, 3604 Sqft

Welcome 63 Chadwick Dr, in the highly coveted neighborhood of South Windermere, less than 10 minutes to downtown and just 20 minutes to Folly Beach... 

More Details Compare

Sold Price: $1,800,000
Provided courtesy of The Boulevard Company
75 Photos 48 Chadwick Drive Charleston, SC 29407

48 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24029034 / Active Contingent
5 br, 3 ba, 2625 Sqft

Charming five Bedroom, Mid-Century Modern Home in South Windermere!Nestled on a tranquil marsh front lot with gorgeous oak trees, this beautifully ... 

More Details Compare

$1,180,000
Reduced -$120,000
Provided courtesy of Carolina One Real Estate
24 Photos Sold 8 Charlestowne Road Charleston, SC 29407

8 Charlestowne Road
Charleston, SC 29407
South Windermere
Residential

MLS# 24027692 / Sold
3 br, 2 ba, 1900 Sqft

Welcome to your dream home nestled in the picturesque neighborhood of South Windermere! This delightful ranch-style residence is close proximity to... 

More Details Compare

Sold Price: $970,000
Provided courtesy of The Cassina Group
1 Photos Sold 18 Rebellion Road Charleston, SC 29407

18 Rebellion Road
Charleston, SC 29407
South Windermere
Residential

MLS# 24026563 / Sold
4 br, 3 ba, 1 Half Bath, 3566 Sqft

Discover your dream home minutes from downtown Charleston and Folly Beach! This charming 3,566 sq. ft. residence at 18 Rebellion Road offers 4 bedr... 

More Details Compare

Sold Price: $1,717,500
Provided courtesy of Maison Real Estate
73 Photos Sold 69 Chadwick Drive Charleston, SC 29407

69 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24026525 / Sold
4 br, 3 ba, 2471 Sqft

This stunning four bedroom, two and half bath home in the highly sought after Windermere neighborhood offers the perfect blend of classic charm and... 

More Details Compare

Sold Price: $1,205,000
Provided courtesy of The Exchange Company, LLC
17 Photos 148 Chadwick Drive Charleston, SC 29407

148 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24025460 / Active
3 br, 2 ba, 1437 Sqft

Live in the center of everything. This 3BR/2BA brick ranch is conveniently located in South Windermere. Minutes from downtown. Easy walking distanc... 

More Details Compare

$849,500
Reduced -$25,000
Provided courtesy of Harrison Creek Enterprises Inc
51 Photos Sold 36 Tarleton Drive Charleston, SC 29407

36 Tarleton Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24021594 / Sold
4 br, 2 ba, 1 Half Bath, 2581 Sqft

Located in one of Charleston's most popular neighborhoods, this beautifully appointed 4 bedroom, 2.5 bath home is waiting for you. The open living ... 

More Details Compare

Sold Price: $1,065,000
Provided courtesy of The Boulevard Company
1 Photos Sold 57 Chadwick Drive Charleston, SC 29407

57 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24020605 / Sold
4 br, 3 ba, 2918 Sqft

Welcome to 57 Chadwick Drive in the heart of South Windermere, one of West Ashley's most sought-after neighborhoods. Situated on nearly 1/2 an acre... 

More Details Compare

Sold Price: $1,325,000
Provided courtesy of William Means Real Estate, LLC
65 Photos Sold 37 Rebellion Road Charleston, SC 29407

37 Rebellion Road
Charleston, SC 29407
South Windermere
Residential

MLS# 24016664 / Sold
6 br, 3 ba, 1 Half Bath, 3264 Sqft

Welcome to 37 Rebellion Road, a contemporary marsh front oasis! Nestled in the established and desirable South Windermere neighborhood, this elevat... 

More Details Compare

Sold Price: $1,850,000
Provided courtesy of Carolina One Real Estate
49 Photos Sold 18 Lord Ashley Drive Charleston, SC 29407

18 Lord Ashley Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24016024 / Sold
3 br, 2 ba, 1566 Sqft

Welcome to 18 Lord Ashley Drive, located in the esteemed South Windermere neighborhood, offering the rare advantage of no HOA restrictions. This be... 

More Details Compare

Sold Price: $985,000
Provided courtesy of The Boulevard Company
10 Photos Sold 258 Confederate Circle Charleston, SC 29407

258 Confederate Circle
Charleston, SC 29407
South Windermere
Residential

MLS# 24013422 / Sold
5 br, 4 ba, 1 Half Bath, 3749 Sqft

A Charleston traditional, one family owned home for over 60 years, on most desirable Confederate Circle, in the well established and sought after S... 

More Details Compare

Sold Price: $1,500,000
Provided courtesy of Elaine Brabham and Associates
44 Photos Sold 351 Confederate Circle Charleston, SC 29407

351 Confederate Circle
Charleston, SC 29407
South Windermere
Residential

MLS# 24010783 / Sold
4 br, 3 ba, 1 Half Bath, 3807 Sqft

This Just May Be Your Dream Home... Step inside the double front doors to an expansive living space. On one side is an airy and open living room wi... 

More Details Compare

Sold Price: $1,955,000
Provided courtesy of Handsome Properties, Inc.
59 Photos Sold 11 Jamaica Drive Charleston, SC 29407

11 Jamaica Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24010706 / Sold
3 br, 2 ba, 1800 Sqft

Embrace this incredible opportunity to own in one of Charleston's most coveted neighborhoods of South Windermere. The current owners' love for this... 

More Details Compare

Sold Price: $950,000
Provided courtesy of The Boulevard Company
33 Photos Sold 7 Charlestowne Road Charleston, SC 29407

7 Charlestowne Road
Charleston, SC 29407
South Windermere
Residential

MLS# 24008519 / Sold
3 br, 2 ba, 1973 Sqft

Amazing opportunity to purchase a classic renovated home in the highly sought after South Windermere neighborhood, West of the Ashley. This locatio... 

More Details Compare

Sold Price: $888,000
Provided courtesy of Carolina One Real Estate
27 Photos Sold 134 Chadwick Drive Charleston, SC 29407

134 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 24004656 / Sold
4 br, 2 ba, 2032 Sqft

Charming 4 bedroom 2 bath brick ranch on tidal creek with dock, located in one of Charleston's most beloved neighborhoods and only 2 traffic lights... 

More Details Compare

Sold Price: $965,000
Provided courtesy of A House in the South Realty
32 Photos Sold 69 Chadwick Drive Charleston, SC 29407

69 Chadwick Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 23026416 / Sold
4 br, 3 ba, 2471 Sqft

Located in coveted South Windermere, walking distance to St. Andrews School for Math and Science. This is a 4 bedroom, 3 bathroom house with office... 

More Details Compare

Sold Price: $815,000
Provided courtesy of Baker Realty
45 Photos Sold 324 Confederate Circle Charleston, SC 29407

324 Confederate Circle
Charleston, SC 29407
South Windermere
Residential

MLS# 23022788 / Sold
4 br, 3 ba, 1 Half Bath, 3140 Sqft

Located on one of the best streets in one of Charleston's most beloved neighborhoods. 2 traffic lights to downtown and remodeled! Large home, mostl... 

More Details Compare

Sold Price: $1,485,000
Provided courtesy of Carolina One Real Estate
40 Photos Sold 236 Confederate Circle Charleston, SC 29407

236 Confederate Circle
Charleston, SC 29407
South Windermere
Residential

MLS# 23021110 / Sold
4 br, 3 ba, 3132 Sqft

Step into luxury in this elegant brick beauty nestled in coveted South Windermere. With a living room that radiates warmth from its exquisite firep... 

More Details Compare

Sold Price: $1,330,000
Provided courtesy of Century 21 Properties Plus
28 Photos Sold 4 Tarleton Drive Charleston, SC 29407

4 Tarleton Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 23015700 / Sold
3 br, 1 ba, 1 Half Bath, 1741 Sqft

This Classic South Windermere 3 bedroom, 1.5 bath brick home's entrance is framed perfectly by two stunning Live Oak trees. With only 2 owners si... 

More Details Compare

Sold Price: $869,000
Provided courtesy of Bill Hurtes Realty
29 Photos Sold 1 Lord Ashley Drive Charleston, SC 29407

1 Lord Ashley Drive
Charleston, SC 29407
South Windermere
Residential

MLS# 23009967 / Sold
3 br, 2 ba, 2160 Sqft

Charming brick home on a quarter-acre corner lot in highly desirable South Windermere. This home has tremendous curb appeal with mature landscapin... 

More Details Compare

Sold Price: $810,000
Provided courtesy of Beach Residential
Residential, Land, Other Disclaimer:

Broker Reciprocity The data relating to real estate for sale on this web site comes in part from the Broker ReciprocitySM Program of the Charleston Trident Multiple Listing Service. Real estate listings held by brokerage firms other than Marshall Walker Real Estate are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers. Last updated on 02-09-2025 3:29 PM EST . The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2025 Charleston Trident Multiple Listing Service, Inc. All rights reserved.
Commercial Sale/Lease: Copyright 2025 South Carolina commercial MLS, Inc. All rights reserved. Last updated on 02-09-2025 3:29 PM EST est.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website.


This real estate website and IDX data is hosted by Dynamic IDX, LLC (843.637.2411)

Follow us on