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Windermere Homes for Sale | Charleston

Windermere in Charleston, SC, is a desirable neighborhood known for its picturesque surroundings and convenient location. This community features a mix of classic and modern homes, often situated on spacious lots with beautiful landscaping. Residents appreciate the proximity to top-rated schools, shopping centers, and recreational amenities, including parks and walking trails. Windermere offers a welcoming atmosphere and a strong sense of community, making it an ideal choice for families and individuals seeking a vibrant suburban lifestyle.

 

 

Windermere Listings

14 Belvue Road, Charleston image
14 Belvue Road, Charleston $1,275,000

Welcome to this beautifully renovated brick home in the highly sought-after Windermere neighborhood. Blending timeless charm with modern updates, this inviting residence ...

  • 3 Beds
  • 2 Baths
  • 26019803 MLS
  • Windermere SubDv.
  • Active Contingent Status
23 Stocker Drive, Charleston image
23 Stocker Drive, Charleston $1,295,000

23 Stocker Drive is the sort of tasteful gem you might find in the pages of Architectural Digest. Set on high ground along one of Old Windermere's prettiest oak-lined str...

  • 2 Beds
  • 2 Baths
  • 26019279 MLS
  • Windermere SubDv.
  • Active Contingent Status
18 Stocker Drive, Charleston image
18 Stocker Drive, Charleston $1,450,000 ▼

Charming brick home on a quiet family street that is located close to Downtown Charleston, soon to be walkable or bikeable to the Peninsula via a new pedestrian bridge. W...

  • 4 Beds
  • 2.5 Baths
  • 26017914 MLS
  • Windermere SubDv.
  • Active Status
1 Beverly Road, Charleston image
1 Beverly Road, Charleston $1,399,000 ▼

Minutes from Downtown Charleston in highly sought-after Old Windermere, this beautifully restored 1940 brick cottage combines original Charleston character with thoughtfu...

  • 5 Beds
  • 3 Baths
  • 26014984 MLS
  • Windermere SubDv.
  • Active Status
630 Windermere Boulevard Unit #Unit 3b, Charleston image
630 Windermere Boulevard Unit #Unit 3b, Charleston $615,000

Beautifully updated 3BR/3BA townhome offering stylish and functional living space in one of West Ashley's most sought-after neighborhoods! This move-in ready home feature...

  • 3 Beds
  • 3 Baths
  • 26014635 MLS
  • Windermere SubDv.
  • Closed Status
45 Fenwick Drive, Charleston image
45 Fenwick Drive, Charleston $1,010,000

Charming Lowcountry living tucked beneath a canopy of live oaks just minutes from the heart of downtown Charleston, this beautifully maintained home offers the perfect bl...

  • 4 Beds
  • 2.5 Baths
  • 26013875 MLS
  • Windermere SubDv.
  • Closed Status
6 Beverly Road, Charleston image
6 Beverly Road, Charleston $1,685,000

Situated on a tree-lined street in the desirable Windermere neighborhood of West Ashley, this well-appointed home offers strong curb appeal with copper gas lanterns and a...

  • 3 Beds
  • 3.5 Baths
  • 26013520 MLS
  • Windermere SubDv.
  • Closed Status
29 Beverly Road, Charleston image
29 Beverly Road, Charleston $1,535,000

**Showing for back-up offers** A rare in-town two-residence property located in old Windermere. Fully renovated in 2019, this charming brick bungalow offers modern conven...

  • 5 Beds
  • 4 Baths
  • 26011034 MLS
  • Windermere SubDv.
  • Closed Status
35 Beverly Road, Charleston image
35 Beverly Road, Charleston $1,388,000

Set on a tree-lined lot that backs directly to the West Ashley Greenway, 35 Beverly Rd is a newly renovated, move-in-ready home reimagined from the studs out. The main ho...

  • 4 Beds
  • 4.5 Baths
  • 26005604 MLS
  • Windermere SubDv.
  • Closed Status
35 Stocker Drive, Charleston image
35 Stocker Drive, Charleston $1,450,000

ARCHIVAL ONLY

  • 4 Beds
  • 2.5 Baths
  • 25031569 MLS
  • Windermere SubDv.
  • Closed Status
21 Beverly Road Unit #A & B, Charleston image
21 Beverly Road Unit #A & B, Charleston $1,090,000

Welcome to 21 Beverly Road, a fabulous duplex situated in the desirable Windermere subdivision of West Ashley, less than five minutes from downtown Charleston. This prope...

  • 4 Beds
  • 3.5 Baths
  • 25024355 MLS
  • Windermere SubDv.
  • Closed Status
39 Stocker Drive, Charleston image
39 Stocker Drive, Charleston $1,300,000

Fully Renovated Gem in the Heart of Windermere!Welcome to this beautifully restored and meticulously updated home in the highly desirable Old Windermere neighborhood--jus...

  • 4 Beds
  • 3 Baths
  • 25018954 MLS
  • Windermere SubDv.
  • Closed Status
9 Wesley Drive, Charleston image
9 Wesley Drive, Charleston $700,000

Charming Windermere bungalow with high visibility and excellent commercial potential in the Savannah Highway Zoning Overlay. Centrally located on Wesley Drive and bordere...

  • 2 Beds
  • 1.5 Baths
  • 25013502 MLS
  • Windermere SubDv.
  • Closed Status
7 Chadwick Drive Unit #A, Charleston image
7 Chadwick Drive Unit #A, Charleston $525,000

Don't miss your chance to own this beautifully maintained home in one of Charleston's most desirable neighborhoods. This well-cared-for unit features an updated kitchen w...

  • 2 Beds
  • 1.5 Baths
  • 25011679 MLS
  • Windermere SubDv.
  • Closed Status
626 Windermere Boulevard Unit #4d, Charleston image
626 Windermere Boulevard Unit #4d, Charleston $565,000

Beautifully maintained and ideally located, this spacious townhouse on Windermere Blvd offers both comfort and convenience. Just minutes from South Windermere and the Ear...

  • 3 Beds
  • 3 Baths
  • 25011563 MLS
  • Windermere SubDv.
  • Closed Status
41 Berkeley Road, Charleston image
41 Berkeley Road, Charleston $1,200,000

Charming home nestled on a .4-acre lot among the oaks in a highly desirable Windermere neighborhood. The property boasts great bones including three beautiful fireplaces,...

  • 2 Beds
  • 2 Baths
  • 25010771 MLS
  • Windermere SubDv.
  • Closed Status
27 Stocker Drive, Charleston image
27 Stocker Drive, Charleston $1,115,000

This updated 1940s brick Tudor is on a beautiful tree lined street in the sought after neighborhood of Old Windermere. The house has kept all of its original charm with h...

  • 4 Beds
  • 2.5 Baths
  • 25010094 MLS
  • Windermere SubDv.
  • Closed Status
4 Chadwick Drive, Charleston image
4 Chadwick Drive, Charleston $1,042,500

Welcome to 4 Chadwick Drive, a charming, meticulously maintained 1929 brick residence nestled in the sought-after Old Windermere neighborhood of Charleston. This 1,862-s...

  • 3 Beds
  • 1.5 Baths
  • 25008267 MLS
  • Windermere SubDv.
  • Closed Status
26 Beverly Road, Charleston image
26 Beverly Road, Charleston $1,252,517

Gorgeous Colonial style house in need of special updating to make it the show piece it deserves to be. Located in a beautiful neighborhood just off the peninsula and clos...

  • 5 Beds
  • 3 Baths
  • 25005632 MLS
  • Windermere SubDv.
  • Closed Status
69 Folly Road Boulevard, Charleston image
69 Folly Road Boulevard, Charleston $650,000

Charming Home in an Ideal Location - This home is perfectly situated for anyone looking to experience the best of Charleston - whether you're commuting, relaxing at the b...

  • 3 Beds
  • 2 Baths
  • 25003639 MLS
  • Windermere SubDv.
  • Closed Status
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1124 Sam Rittenberg Blvd., Ste 5
Charleston, SC 29407
(843) 266-9111


©2026 CENTURY 21 Expert Advisors.  CENTURY 21® and the CENTURY 21 Logo are registered service marks owned by Century 21 Real Estate LLC.  Equal Housing Opportunity.  Each office is independently owned and operated.

 

 

 

 

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