MLS data updated Aug 20, 2026
Lakeside at the Lakes of Windermere
Gated Windermere condo community minutes from Disney and Lake Burden
Windermere, FL
Lakeside at the Lakes of Windermere is a gated condominium and townhome community in south Windermere off Winter Garden Vineland Road, built in the mid-2000s with resort-style amenities including a pool, fitness center, and clubhouse, plus shared access to Lake Burden minutes from Walt Disney World.
Median sold: $310K · Median days on market: 37 · Sold-to-list: 96.8% · Source: Stellar MLS
About 1.5 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Lakeside at the Lakes of Windermere
Lakeside at the Lakes of Windermere draws a specific kind of buyer: someone who genuinely wants to live in Windermere but has no interest in maintaining a yard, an exterior, or a pool of their own. The community's gated condo format — with exterior maintenance, water, and pest control all rolled into the HOA — appeals to professionals who would rather spend their weekends on the water than on home upkeep.
The employment anchor here is unmistakable. Walt Disney World is roughly six miles from the community's entrance, making Lakeside one of the closest gated residential options for resort professionals, park executives, and Imagineering staff who want a Windermere zip code without a 45-minute commute. The 408 Expressway puts downtown Orlando's medical and legal corridors within 25 minutes, giving the community genuine cross-sector appeal.
What makes the housing stock distinctive is its scale. Units in the 1,100-to-1,600-square-foot range with lake views and access to a shared dock on Lake Burden offer a lifestyle that punches well above the square footage. The pool, fitness center, tennis courts, and dog park round out a resort-style amenity set rarely found at this maintenance level. Buyers who cross-shop Lakeside typically look at The Preserve at the Lakes of Windermere next door for a single-family alternative, or at similar SR-535 corridor condos — but few match the combination of a true Windermere address, gated access, and lakefront proximity that Lakeside delivers.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
1 home pending in Lakeside at the Lakes of Windermere · Avg. $320K
Lakeside at the Lakes of Windermere · 3rd Quarter 2026
16 sales · Stellar MLS · last 12 mo
$310K
Median Sale Price
37 days
Median Days on Market
96.8%
Sold-to-List
$222
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Lakeside at the Lakes of Windermere · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 5,721 | — | 12/1/25 | — | $4,400,000 | $769 | — |
| — | — | 7,222 | — | 12/1/25 | — | $3,150,000 | $436 | — |
| — | — | 5,916 | — | 12/1/25 | — | $2,460,000 | $416 | — |
| — | — | 6,829 | — | 12/1/25 | — | $2,250,000 | $329 | — |
| — | — | 4,044 | — | 12/1/25 | — | $1,875,000 | $464 | — |
| — | — | 4,848 | — | 12/1/25 | — | $1,465,000 | $302 | — |
| — | — | 3,264 | — | 12/1/25 | — | $1,450,000 | $444 | — |
| — | — | 5,120 | — | 12/1/25 | — | $1,420,000 | $277 | — |
| — | — | 3,813 | — | 12/1/25 | — | $1,375,000 | $361 | — |
| — | — | 4,226 | — | 12/1/25 | — | $1,300,000 | $308 | — |
| — | — | 3,014 | — | 12/1/25 | — | $1,230,000 | $408 | — |
| — | — | 4,175 | — | 12/1/25 | — | $1,160,000 | $278 | — |
| — | — | 4,089 | — | 12/1/25 | — | $935,000 | $229 | — |
| — | — | 3,938 | — | 12/1/25 | — | $925,000 | $235 | — |
| — | — | 3,662 | — | 12/1/25 | — | $900,000 | $246 | — |
| — | — | 3,072 | — | 12/1/25 | — | $665,000 | $216 | — |
| — | — | 2,072 | — | 12/1/25 | — | $619,000 | $299 | — |
| — | — | 2,981 | — | 12/1/25 | — | $600,000 | $201 | — |
| — | — | 1,925 | — | 12/1/25 | — | $570,000 | $296 | — |
| — | — | 1,947 | — | 12/1/25 | — | $520,000 | $267 | — |
| — | — | 1,819 | — | 12/1/25 | — | $510,000 | $280 | — |
| — | — | 2,154 | — | 12/1/25 | — | $507,500 | $236 | — |
| — | — | 1,745 | — | 12/1/25 | — | $500,000 | $287 | — |
| — | — | 2,604 | — | 12/1/25 | — | $498,000 | $191 | — |
| — | — | 1,749 | — | 12/1/25 | — | $485,000 | $277 | — |
| — | — | 1,696 | — | 12/1/25 | — | $480,000 | $283 | — |
| — | — | 2,009 | — | 12/1/25 | — | $475,000 | $236 | — |
| — | — | 2,139 | — | 12/1/25 | — | $460,000 | $215 | — |
| — | — | 2,001 | — | 12/1/25 | — | $435,000 | $217 | — |
| — | — | 1,748 | — | 12/1/25 | — | $405,000 | $232 | — |
| — | — | 1,540 | — | 12/1/25 | — | $402,000 | $261 | — |
| — | — | 1,670 | — | 12/1/25 | — | $370,000 | $222 | — |
| — | — | 1,720 | — | 12/1/25 | — | $370,000 | $215 | — |
| — | — | 1,440 | — | 12/1/25 | — | $350,000 | $243 | — |
| — | — | 1,442 | — | 12/1/25 | — | $325,000 | $225 | — |
| — | — | 1,380 | — | 12/1/25 | — | $302,500 | $219 | — |
| — | — | 13,559 | — | 11/1/25 | — | $11,100,000 | $819 | — |
| — | — | 8,431 | — | 11/1/25 | — | $5,500,000 | $652 | — |
| — | — | 6,367 | — | 11/1/25 | — | $3,800,000 | $597 | — |
| — | — | 4,324 | — | 11/1/25 | — | $3,550,000 | $821 | — |
| — | — | 6,489 | — | 11/1/25 | — | $3,178,500 | $490 | — |
| — | — | 1,366 | — | 11/1/25 | — | $2,750,000 | $2,013 | — |
| — | — | 5,693 | — | 11/1/25 | — | $2,400,000 | $422 | — |
| — | — | 5,590 | — | 11/1/25 | — | $1,980,000 | $354 | — |
| — | — | 4,199 | — | 11/1/25 | — | $1,675,000 | $399 | — |
| — | — | 4,475 | — | 11/1/25 | — | $1,435,000 | $321 | — |
| — | — | 3,586 | — | 11/1/25 | — | $1,370,000 | $382 | — |
| — | — | 3,617 | — | 11/1/25 | — | $1,275,000 | $353 | — |
| — | — | 3,267 | — | 11/1/25 | — | $1,150,000 | $352 | — |
| — | — | 4,202 | — | 11/1/25 | — | $1,150,000 | $274 | — |
| — | — | 3,053 | — | 11/1/25 | — | $1,120,000 | $367 | — |
| — | — | 2,390 | — | 11/1/25 | — | $930,000 | $389 | — |
| — | — | 2,262 | — | 11/1/25 | — | $775,000 | $343 | — |
| — | — | 3,800 | — | 11/1/25 | — | $750,000 | $197 | — |
| — | — | 3,399 | — | 11/1/25 | — | $722,500 | $213 | — |
| — | — | 2,854 | — | 11/1/25 | — | $710,000 | $249 | — |
| — | — | 3,103 | — | 11/1/25 | — | $705,000 | $227 | — |
| — | — | 3,313 | — | 11/1/25 | — | $700,000 | $211 | — |
| — | — | 2,542 | — | 11/1/25 | — | $700,000 | $275 | — |
| — | — | 2,042 | — | 11/1/25 | — | $670,000 | $328 | — |
Currently For Sale
2 active listings in Lakeside at the Lakes of Windermere
$254/sqft
View details
$223/sqft
View details
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|
| 2 | 2 | 1,161 | $295,000 | $254 | 63 |
| 3 | 2 | 1,455 | $325,000 | $223 | 59 |
Lakeside at the Lakes of Windermere Market — Common Questions
Is Lakeside at the Lakes of Windermere a buyer's or seller's market in 2026?+
Lakeside at the Lakes of Windermere is currently a seller's market with about 1.5 months of inventory. About 1.5 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Lakeside at the Lakes of Windermere?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Lakeside at the Lakes of Windermere is approximately $310K, down about 1.9% from a year earlier.
How many homes are for sale in Lakeside at the Lakes of Windermere?+
There are currently 2 active listings in Lakeside at the Lakes of Windermere, with homes selling at roughly 1.3 per month. That works out to about 1.5 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
5.0 ★ · 42 reviews
What clients say
All 42 reviews on Zillow“Ryan was amazing. Extremely knowledgeable and doesn't want to waste time. Process was very smooth and he always answered all of my calls and questions immediately.”
“Ryan was very helpful and quick to answer any questions I had. I was on a deadline to be out of my house and he made it happen — and in the end my family and I have a beautiful house.”
Report generated August 29, 2026 at 7:37 AM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is 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. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Lakeside at the Lakes of Windermereor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of August 20, 2026 at 3:09 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Moving to Lakeside at the Lakes of Windermere
Utilities & Services
Lakeside at the Lakes of Windermere is in Orange County, Florida. Here's who to call to get power, water, and trash service set up in your name before closing.
Electric
Orlando Utilities Commission (OUC) · (407) 423-9018City of Orlando and parts of unincorporated Orange County. OUC also provides water in its territory.
Duke Energy Florida · (800) 700-8744Most of unincorporated Orange County, plus Winter Garden, Apopka, and Ocoee.
Water & Sewer
Orange County Utilities · (407) 836-5515Unincorporated Orange County (water & sewer).
OUC — Water (City of Orlando) · (407) 423-9018City of Orlando — OUC provides both water and electric.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is 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.
Based on information submitted to the MLS GRID as of August 20, 2026 at 3:09 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA