Neighborhood · Windermere, Florida
Lakeside Village
Family living minutes from Windermere's best lakes
93
Homes for sale
$599,000
Median list price
$265
Avg price / sqft
43
Median days on market
Lakeside Village sits in the heart of Windermere, a slice of Orange County where a suburban rhythm meets easy access to some of Central Florida's most recognizable communities. You're within reach of established names like Isleworth, Keenes Pointe, and Summerport, with Windermere High and Horizon West Middle serving families here. Disney is about 22 minutes out, downtown Orlando roughly 33, and MCO around 41 — close enough for commuting and day trips without living on top of the parks.
For buyers, the picture is active but not frantic. There are 97 homes on the market with a median list price of $639,000, and the 268 sales over the past year closed at a median of $600,000 — sellers are getting about 98% of asking, so realistic offers win here. With a median of 34 days on market, you have time to make a considered decision, and the range runs wide, from the low $300,000s up to $2.5 million, so it's worth exploring Windermere homes for sale across price points.
Lakeside Village is a community in Windermere, Florida.
Quick facts
$330,000 – $1.8M price range
2,221 sqft median home
$190/mo median HOA
$2,950/mo median rent
259 sold in 12 months
Drive times
On the market now
Homes for sale in Lakeside Village
View all 93 →
$649,000
13324 JERVEY STREET, WINDERMERE
4 bd · 3.5 ba · 2,750 sqft
$379,900
8608 BROOKVALE DRIVE, WINDERMERE
3 bd · 2.5 ba · 1,480 sqft
$1,750,000
9443 ROYAL ESTATES BOULEVARD, ORLANDO
5 bd · 5 ba · 4,222 sqft
$780,000
8713 CRESCENDO AVENUE, WINDERMERE
3 bd · 2.5 ba · 2,497 sqft
$710,999
13239 JERVEY STREET, WINDERMERE
4 bd · 3.5 ba · 2,745 sqft
$639,500
12909 CRAGSIDE LANE, WINDERMERE
4 bd · 2.5 ba · 2,460 sqft
$560,000
8225 BRYCE CANYON AVENUE, WINDERMERE
4 bd · 2.5 ba · 1,840 sqft
$558,000
14373 BREDA CENTER LOOP, WINTER GARDEN
3 bd · 2.5 ba · 2,488 sqft
$500,000
13424 HOPKINTON COURT, WINDERMERE
4 bd · 2 ba · 2,190 sqft
$449,000
12333 VIA DERNA PLACE, WINDERMERE
3 bd · 2.5 ba · 1,919 sqft
$409,900
8860 HERENCIA ALLEY, WINDERMERE
3 bd · 2.5 ba · 1,547 sqft
$360,000
12417 CRUXBURY DRIVE, WINDERMERE
2 bd · 2.5 ba · 1,311 sqft
Every active listing inside the Lakeside Village boundary
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Browse Lakeside Village
By feature — on the live map
Where the market lives
The numbers that matter
The Lakeside Village market
259
Sold, last 12 months
$585,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
27 days
Median time to sell
Lakeside Village vs Windermere
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 4.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Lakeside Village boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Lakeside Village is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Lakeside Village home
≈ $4,099/mo
$599,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$190/mo
Median HOA
From current listings inside the boundary
$2,950/mo
Median rent
Homes for rent inside the boundary
Population
19,390
Median age
36
Median income
$123,605
Median home value
$489,452
Beyond the listings
Living in Lakeside Village
Entertainment
Top 5% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Hobbies & Interests
Top 10% in the U.S.Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Food & Drink
Top 20% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Lifestyles
Top 23% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Lifestyles
Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
Straight answers
Lakeside Village FAQs
Is Lakeside Village a good place to live?+
It's a solid fit for families who want Windermere schools and quick access to the parks without paying Isleworth prices. Homes feed into Windermere High and Horizon West Middle, and you're about 22 minutes from Disney and 33 from downtown Orlando. The mix of price points and 23 pool homes currently listed gives buyers real options.
Is Lakeside Village expensive?+
It sits in the mid-to-upper tier for the Windermere area, with a median list price of $639,000 and a median home size of 2,594 sqft at about $272 per square foot. That said, the range is broad — from $330,000 up to $2.5 million — so there's room for both first move-up buyers and those shopping the Keenes Pointe tier above $1M.
What do homes cost in Lakeside Village?+
The median list price is $639,000, while homes that actually sold over the past 12 months closed at a median of $600,000 across 268 sales. Expect roughly $272 per square foot on a typical 2,594-sqft home, with listings ranging from $330,000 to $2,500,000.
How is the market right now?+
Balanced and steady — 97 homes are active, the median days on market is 34, and sellers are averaging about 98% of their asking price. That tells you well-priced homes move at a reasonable pace, and buyers have negotiating room without a bidding-war frenzy. Comparing across Summerport and nearby communities helps you gauge value.
What about HOA fees and property taxes?+
The median HOA runs about $160 per month, and median property taxes come in around $6,687 per year. Five of the active listings are in gated communities, and if you're weighing renting instead, the median rent here is about $2,900 per month.
Keep exploring
More Windermere neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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