8179 Maritime Flag Street Unit 206, Windermere
407-616-9019
Real Estate Company
There are 87 homes for sale in Lakeside, Florida as of 2026-10-04, at a median list price of $560,000 and a median of 72 days on market. Every active Lakeside listing is above, newest first. What follows is what those listings add up to.
| Active listings | 87 |
|---|---|
| Median list price | $560,000 |
| Median price per square foot | $260 |
| Median size | 2,147 square feet |
| Median year built | 2014 |
| Median days on market | 72 |
| On market 60+ days | 53 (60.92%) |
| Priced below original asking | 47 (54.02%) |
Source: Stellar MLS via the Bridge RESO feed, pulled 2026-10-04. Updated weekly.
47 of the 87 Lakeside homes on the market (54%) are asking less than they did on day one, and 53 (61%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 72 days in who has already cut once is a different negotiation than one of the 34 listings still inside its first 60 days.
Across the 47 Lakeside listings that have already come down, the typical reduction is 3.86% off the original asking price. That is the size of a first concession, not a final one.
| Under $250,000 | 0 | 0.0% |
|---|---|---|
| $250,000 to $400,000 | 19 | 21.8% |
| $400,000 to $600,000 | 28 | 32.2% |
| $600,000 and up | 40 | 46.0% |
| Single Family Residence | 53 |
|---|---|
| Townhouse | 27 |
| Condominium | 7 |
Every Lakeside subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. Every one of the 87 Lakeside listings carries a subdivision name.
Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-10-04. * Medians on rows with fewer than 4 listings are indicative only. Open a subdivision for days on market, price per square foot and sales history.
No active listing today. Each page keeps its sales history and refills as inventory changes.
Lakeside is the oldest village in Horizon West. Its comprehensive plan amendment is numbered 97-1-B-1-1, the first of the six, and that head start is why it has the most established housing stock and the widest mix of home types, condominiums included, where the newer villages are almost entirely houses and townhomes.
The village is known as the eastern gateway to Horizon West and was approved for 8,915 homes. Its center is not one development but two adjoining ones, Lakeside Village Center and Westside Shoppes, which together hold the largest range of shops and restaurants in Horizon West.
It is the village closest to Walt Disney World, close enough that many homes see the nightly fireworks. Its larger communities carry Windermere and lake names, among them Lake Sawyer South, Windermere Trails, Lake Burden South and Palms at Windermere, and Lakeside addresses carry a Windermere mailing city rather than Winter Garden.
34786 (87 listings)
There were 87 active residential listings in Lakeside as of 2026-10-04, at a median list price of $560,000. That count comes from the Stellar MLS feed and is refreshed weekly.
The median list price in Lakeside was $560,000 as of 2026-10-04, or about $260 per square foot. The median home on the market is 2,147 square feet and was built in 2014.
Median days on market was 72 as of 2026-10-04. 53 of the 87 listings, 61% of the Lakeside market, have been listed 60 days or longer, and that is where most of the negotiating room sits.
47 Lakeside listings, 54.02% of the market, are now asking less than they did originally, at a median reduction of 3.86%. That is the size of a typical first concession here, and it is usually not the last one.
37 named subdivisions had at least one active listing in Lakeside as of 2026-10-04, and every one is listed above with its active count and median list price. Lake Sawyer South led with 11 active listings at a median of $555,000.
Lakeside listings sat in 1 zip code as of 2026-10-04: 34786 with 87 active listings.
The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Lakeside listing on this page.