How are the homes ordered?

Homes are shown from lowest to highest asking price within this page's price range.

Which Windermere addresses does this page cover?

The listings use the broader saved Windermere area from our main guide, covering the town and surrounding locations. It is not restricted to the incorporated Town of Windermere. Check the jurisdiction and mapped position of any property you are considering.

Does the search include only detached houses?

No. It includes matching property types with at least one listed bedroom. Condos and townhomes can appear alongside detached homes. Review each listing's property type and ownership arrangements.

Are these all detached homes in the Town of Windermere?

No. Matching condos, townhomes and detached homes can appear. The saved Windermere area includes the town and surrounding locations, so check the property type and jurisdiction of each address.

What should you compare beyond the purchase price?

Request information about recurring association charges, property upkeep and work you would want to complete. Build a property-specific comparison so a lower asking price does not obscure a different set of ongoing commitments.

What happens if there are no matching homes?

The page keeps its stated area and filters. It does not expand the search automatically. You can choose another budget or explore the wider Windermere guide.

Illustrative Windermere lakefront setting with mature oak trees, landscaped lawns and homes beside calm water in warm morning light.

Homes for Sale Under $500K in Windermere FL

Browse Windermere homes asking less than $500,000. Compare current listings, layouts and ownership details within the broader saved area.

Homes for Sale Under $500K in Windermere FL

10 listings

43 days on market
$290,000Price reduced by $5,000 on Oct 19, 2026
11446 Jasper Kay Terrace Unit 202Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
36 days on market
$294,997Price reduced by $3,000 on Nov 2, 2026
8168 Boat Hook Loop Unit 302Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
133 days on market
$295,000
8180 Boat Hook Loop Unit 102Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
171 days on market
$299,500
8180 Boat Hook Loop Unit 109Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
26 days on market
$319,900Price reduced by $5,000 on Nov 6, 2026
8276 Maritime Flag St Unit 1204Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,455 sqft
72 days on market
$320,000
8168 Boat Hook Loop Unit 303Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,442 sqft
31 days on market
$350,000
8179 Maritime Flag Street Unit 206Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,332 sqft
94 days on market
$410,000Price reduced by $10,000 on Oct 1, 2026
11425 Brownstone StreetWindermere, FL, 34786
- 3 beds
- 3 baths
- 1,881 sqft
127 days on market
$429,000Price reduced by $10,000 on Oct 14, 2026
11429 Brownstone StreetWindermere, FL, 34786
- 4 beds
- 3 baths
- 1,910 sqft
19 days on market
$435,000
11267 Grander DriveWindermere, FL, 34786
- 3 beds
- 3 baths
- 1,743 sqft
Browse all listings10 listings

View all matching homes

What this search includes

Current asking prices below $500,000, ordered from lowest to highest.

The listings use our broader saved Windermere area, covering the town and surrounding locations. This is not a town-limits-only search. Matching homes have at least one listed bedroom and can include condos, townhomes and detached houses.

Explore all Windermere homes for sale. The hero image is illustrative; listing cards show individual properties.

Compare the ownership arrangement first

For a Windermere search under $500K, start with the form of ownership you would be comfortable taking on. Compare the space inside the home with parking, storage and maintenance responsibilities. This price search includes matching property types in the broader saved area; it does not select only detached houses within the town.

Four checks for your Windermere shortlist

Usable rooms and storage
Check room dimensions, bedroom placement and storage against the way you plan to live.
Parking and daily routes
Check parking arrangements and test journeys from the exact address to your regular destinations.
Condition and upkeep
Review the property's condition and distinguish essential work from changes you would simply prefer.
Ownership commitments
Request the association information and compare recurring charges and maintenance responsibilities.

Look beyond the initial asking price

Ask what any recurring community or building charges cover and which items you would maintain yourself. Compare the home's condition with work you would need before moving in. A purchase ceiling is most useful when it sits alongside a clear view of the commitments for each address.

Check the property and its wider arrangements

Check the property's jurisdiction and the arrangements that apply to the home or community. Review recurring charges and maintenance responsibilities, and establish any separate costs for facilities you would use. A Windermere address does not by itself establish town residency or amenity eligibility.

Explore our Windermere neighborhood guide and living guide for further questions to bring to your shortlist.

Windermere area asking-price context

All prices, property types and bedroom counts in the saved Windermere area. Asking-price context for the wider selection, not this price category.

For sale now: —
Median asking price: —

Questions about this Windermere search

Questions when comparing your shortlist

Gaby Sadler

Property Specialist, Serhant

Compare Windermere homes with Gaby

Tell me your priorities and your budget under $500K. I can arrange viewings and help you compare layouts, locations and ownership details across your Windermere shortlist.

+1 (407) 490-0475 realty@thetopvillas.com