- 5 beds
- 5 baths
- 2,283 sqft

Homes for Sale Under $500K in Windsor Island Resort FL
Browse Windsor Island Resort homes asking less than $500,000. Compare layouts, current listings and ownership details within the mapped area.
Homes for Sale Under $500K in Windsor Island Resort FL
25 listingsWhat this search includes
Homes asking below $500,000, ordered from lowest to highest. The price ceiling excludes that boundary value.
This search retains the mapped Windsor Island Resort area from our main guide. It does not expand into nearby Davenport communities or other similarly named Windsor resorts. Matching properties have at least one listed bedroom and can include different property types.
Compare ownership form before floor area
Start below $500K by deciding how you want to own and maintain your home. Compare the interior with parking, storage and access, then review the responsibilities attached to the property or community. Leave room in your plans for work you would want completed before moving in.
Four checks for your Windsor Island Resort 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.
Check what the asking price includes
For a condo or townhome, request information about shared maintenance and recurring charges. For a detached home, assess the exterior and grounds alongside the rooms. The price selection does not establish which arrangement will fit your routine.
Understand Windsor Island Resort ownership responsibilities
Review association services, the home's private upkeep and any district assessment as separate parts of ownership. Request current property statements and documents explaining responsibilities, charges and planned work. Keep permitted personal use, a proposed rental-management arrangement and access to shared facilities as distinct questions for the home you are considering.
Compare the Windsor Island home and its practical setting
Review the actual entrance, parking and route to the places you expect to use during a stay. Compare the home's sleeping-room allocation with dining, gathering and outdoor spaces, without assuming every property has the same layout or facilities. Establish current resort operations and the access arrangements for the particular address.
Windsor Island Resort: wider asking-price context
All prices, property types and bedroom counts in the mapped area. These asking-price figures describe the wider market, not this price selection.
- For sale now
- 102
- Median asking price
- $640,000
Questions about this Windsor Island Resort search
Questions when comparing your shortlist

Gaby Sadler
Property Specialist, Serhant
Compare Windsor Island Resort 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 Windsor Island Resort shortlist.
Explore Windsor Island Resort homes by bedroom count
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More on Windsor Island Resort
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- 8-Bedroom Homes for Sale in Windsor Island Resort FL
- 9-Bedroom Homes for Sale in Windsor Island Resort FL
- Homes for Sale Over $1 Million in Windsor Island Resort FL
- Homes for Sale Under $600K in Windsor Island Resort FL
- Homes for Sale Under $700K in Windsor Island Resort FL
- Homes for Sale Under $800K in Windsor Island Resort FL
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