Windermere, West Ashley
Windermere and The Crescent Homes for Sale and Neighborhood Guide
By Blake Heron, Realtor, Heron Homes CHS with eXp Realty.
Windermere, South Windermere and The Crescent sit inside 526 in West Ashley, along the Ashley River and Wappoo Creek, about 10 minutes from downtown Charleston. Tree lined streets of mid century homes sit next to some of the largest homes in West Ashley, close to the Windermere and South Windermere shopping centers.
Blake's read on the market. This is the top of the West Ashley market, and it moves fast. Half the homes sold within 14 days, at a median 98.3% of list price. Most homes in Windermere and South Windermere sold between $800K and $3.2M, while The Crescent is its own tier, with 6 sales at a median of $5M and a top sale of $8.45M on Sayle Road. For comparison, the median single family home inside 526 sold for $620K.
What different homes sell for
Median sale price over the past 12 months.
Homes sold by price, past 12 months
Every closed sale, all residential, Charleston MLS, October 2025 through September 2026.
Streets buyers ask me about
Sales are for the past 12 months, all residential, Charleston MLS.
Sayle Road and Broughton Road
The Crescent’s largest homes. 7 Sayle Road sold for $8.45M, and two homes on Broughton Road sold for $7.75M and $7.25M.
Confederate Circle
Five sales at a median of $2.8M, topped by 337 Confederate Circle at $3.2M.
Chadwick Drive and Rebellion Road
Chadwick Drive was the most active street of the year with seven sales at a median of $1.02M, and Rebellion Road had four at a median of $1.31M.
Beverly Road
Six sales at a median of $1.46M in Windermere.
What buyers look for here
Features as marked by listing agents in the Charleston MLS, past 12 months. Some homes with these features are not marked.
Primary bedroom down
28 of the 34 single family homes that sold had the primary bedroom on the main level.
Marsh front
8 sales were marked marsh front, at a median of $2.06M.
Private pool
6 homes with an in ground pool sold, at a median of $2.29M.
No HOA
19 of the 36 sales were marked with no HOA fee.
What to know before you buy in Windermere
Older homes
The typical home here was built in the 1950s or 1960s, and condition varies a lot from original to fully rebuilt. I help you sort out renovation scope and cost before you make an offer.
Flood and insurance
Some West Ashley streets near creeks and marsh sit in a flood zone and some do not, and two homes a block apart can have very different insurance costs. I pull the flood zone and an insurance quote for every home before you make an offer.
Schools
West Ashley is served by the Charleston County School District. Assignments follow exact addresses and can change, so I verify the schools for every home with the district before you buy.
Living in Windermere
Day to day
The Windermere and South Windermere shopping centers have groceries, coffee and restaurants close by, and Avondale Point is a short drive up Savannah Highway.
Getting around
Downtown Charleston and MUSC are about 10 minutes away over the Ashley River bridges, and Folly Beach and James Island are close.
Buying or selling in Windermere
From an older home on Chadwick Drive to an estate in The Crescent, every home here prices differently. I will walk you through the recent sales that matter for your exact home or search. Call or text Blake Heron at 843-718-6338. Heron Homes CHS, eXp Realty.
Explore nearby areas
Prices from the Charleston MLS, all residential, West Ashley, MLS area 11, subdivisions Windermere, South Windermere and The Crescent, closed sales October 2025 through September 2026. Pulled October 2026. Rules and school assignments can change, and I confirm them for each property.
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