Homes for sale in
Windermere, Florida
Chain-of-lakes living minutes from every Orlando exit
234
Homes for sale
$1,089,500
Median list price
$448
Avg price / sqft
48
Median days on market
Windermere sits on the Butler Chain of Lakes west of downtown Orlando, and the town's character is built around that water — quiet streets, oak canopy, and communities like Keenes Pointe and Isleworth that draw buyers who want space without leaving the metro. It's a place where you can keep a boat on the chain and still reach Walt Disney World in about 32 minutes, Universal in roughly the same, and downtown Orlando or Orange County offices in about 33. The waterfront homes and estate lots share the map with more attainable single-family homes in Summerport and Lakeside, so the town covers a wide range of buyers.
Right now there are 272 active listings with a median list price of $1,099,500, though the range runs from the $282,500s up into eight figures. Over the past year 667 homes sold at a median of $812,000, with sellers averaging 96% of asking and a median of 32 days on market — a market that rewards realistic pricing on both sides. If you're value-shopping, it's worth tracking just reduced listings and using browse by price to find the entry points.
Windermere is in Orange County, Florida.
Quick facts
$295,000 – $30M price range
3,267 sqft median home
$3,000/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Windermere
View all 234 homes →
$529,000
4844 FLINT ROAD, WINDERMERE
3 bd · 2 ba · 2,085 sqft
$12,350,000
9312 BLANCHE COVE DR, WINDERMERE
7 bd · 9.5 ba · 11,465 sqft
$669,000
7537 BROFIELD AVENUE, WINDERMERE
4 bd · 3.5 ba · 2,610 sqft
$1,288,999
11524 CLAYMONT CIRCLE, WINDERMERE
5 bd · 4 ba · 3,358 sqft
$1,305,741
14213 CREST PALM AVENUE, WINDERMERE
6 bd · 4.5 ba · 4,564 sqft
$1,318,000
11768 HAMPSTEAD STREET, WINDERMERE
6 bd · 4 ba · 3,900 sqft
$556,256
13321 LUSH LIME ALLEY, WINDERMERE
3 bd · 2.5 ba · 1,649 sqft
$900,000
8278 PROCIDA ISLE LANE, WINDERMERE
6 bd · 4 ba · 4,176 sqft
$27,000,000
5603 MARLEON DRIVE, WINDERMERE
7 bd · 9 ba · 22,108 sqft
$15,500,000
12488 PARK AVENUE, WINDERMERE
10 bd · 14.5 ba · 13,425 sqft
$3,750,000
9960 6TH STREET, WINDERMERE
5 bd · 5.5 ba · 6,182 sqft
$1,500,000
11035 SCHOONER WAY, WINDERMERE
4 bd · 3 ba · 3,517 sqft
234 of 234 active listings shown
Open full map search →Find your fit
Most popular Windermere searches
Popular searches
Property features
The numbers that matter
The Windermere market
Leans seller
4.0 months of inventory
Demand still outpaces supply, but buyers have a little more room.
678
Sold, last 12 months
$808,500
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
35 days
Median time to sell
Windermere vs Orange County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
Homes on the market
▼ 8.0% yr/yr
Homes sold per month
Live Stellar MLS data — listings and closed sales in Windermere, FL. Rolling medians smooth single-month swings in thin markets.
Where to look
Windermere neighborhoods
Lakeside Village
98 homes · $629K median
Keenes Pointe
18 homes · $2.4M median
Isleworth
18 homes · $5.1M median
Summerport
10 homes · $592K median
Butler Bay
6 homes · $1.2M median
Lake Burden South
6 homes · $449K median
Silver Woods
6 homes · $580K median
Lakeside At Lakes Of Windermere
4 homes · $312K median
Casabella
4 homes · $3.6M median
Lake Butler Estates
4 homes · $1.7M median
Eden Isle
4 homes · $710K median
Gardens Of Isleworth
4 homes · $3.8M median
Belmere
4 homes · $735K median
Reserve At Lake Butler Sound
3 homes · $1.6M median
Casa Del Lago
3 homes · $1.6M median
Enclave At Windermere Landing
3 homes · $1.3M median
Willows At Lake Rhea
3 homes · $1.1M median
Windsor Hill
3 homes · $1.4M median
Show all 87 Windermere neighborhoods A–ZHide the full neighborhood list+
Neighborhood boundaries by edgeAI — listings matched to the actual polygon, not agent-entered subdivision names.
For the school run
School zones with homes for sale
Homes matched to official attendance boundaries — always verify zoning with the district.
Beyond the listings
Living in Windermere
Butler Chain waterfront
Fifty active waterfront listings put lakefront and boat-access living within reach across several communities.
Pools are the norm
With 143 of 272 listings offering a pool, private outdoor space is standard rather than a splurge here.
Gated and golf options
76 gated and 38 golf-community listings give buyers real choice in privacy and lifestyle.
A wide price ladder
Listings run from the $282,500s to $30 million, so entry buyers and luxury buyers share the same town.
Central to all of Orlando
Disney, Universal, and downtown Orlando each sit roughly 32-33 minutes away, with MCO about 42.
Population
3,034
Median age
52.7
Median income
$156,042
Median home value
$906,600
What people here are into
Food & Drink
Top 7% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Lifestyles
Top 8% 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.
Emotional
Top 12% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Relationships
Top 14% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Beliefs
Top 14% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Attitudes
Top 16% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
What it really costs
Owning here
Owning the median Windermere home
≈ $6,970/mo
$1,089,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
11%
In a FEMA flood zone
Ask about flood insurance early — it changes the payment
$3,000/mo
Median rent
62 homes for rent right now
Straight answers
Windermere real estate FAQs
Is Windermere a good place to live?+
Windermere pairs a quiet, water-oriented small-town feel with easy access to the whole Orlando metro — Disney, Universal, and downtown are each about 32-33 minutes out. Assigned schools include Windermere High and Windermere Elementary, and communities like Summerport offer neighborhood amenities. It suits buyers who want space and lakes without giving up the city.
Is Windermere expensive?+
It skews upscale: the median list price is $1,099,500 and 142 of the 272 active listings are priced above $1 million. That said, the market starts around $282,500, so there are more attainable options — browse by price to see where they land.
What do homes cost in Windermere?+
Homes sell at a median of $812,000, while active listings carry a higher median of $1,099,500. Pricing averages about $447 per square foot on a median home size of 3,204 square feet, and single-family homes make up the bulk of inventory at 228 of 272 listings.
How is the Windermere housing market right now?+
It's steady and priced-driven: 667 homes sold over the past 12 months, with a median of 32 days on market and sellers netting about 96% of asking. Well-priced homes move, while ambitious asks sit — keeping an eye on just reduced listings can reveal negotiating room.
What about HOA fees and property taxes?+
The median HOA runs about $227 per month, common in the town's planned and gated communities, and median property tax is roughly $9,424 per year. Fees vary widely by community, so it's worth confirming the numbers for any specific neighborhood before you commit.
Keep exploring
Nearby areas
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. Market statistics are computed from listing and sold data and change as the market moves.
Never miss a listing
New Windermere homes, in your inbox
A daily digest of every new listing in Windermere — straight from the MLS, hours after it goes live. Unsubscribe anytime.