- 5 beds
- 5 baths
- 2,283 sqft

5-Bedroom Homes for Sale in Windsor Island Resort FL
Find 5-bedroom homes for sale in Windsor Island Resort. Compare current listings, layouts and ownership details within the mapped area.
Browse 5-bedroom homes in Windsor Island Resort
45 listingsBrowse 5-bedroom homes by asking price
Each band keeps the same area and bedroom count. Bands use asking prices; availability can change.
A focused Windsor Island Resort bedroom search
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.
These listings report 5 bedrooms; the search does not impose a property type. Review the allocation and ownership form for each home.
Balance private rooms with shared capacity
Five bedrooms make it useful to assess the space outside the sleeping rooms just as carefully. Look at seating, dining, kitchen storage and the routes people would use at busy times. Check how many rooms are on each floor and whether their bathroom access matches the intended arrangement.
Four checks for your 5-bedroom shortlist
Bedroom placement
Review which rooms are together and which are separated across floors or living areas.
Bathrooms and stairs
Trace nighttime and morning routes rather than assessing rooms individually.
Shared capacity
Compare seating, dining and kitchen space with the way the bedrooms would be used.
Storage and parking
Assess garage capacity, laundry and everyday equipment storage in use.
Consider guests without losing everyday function
Review where visitors could stay while keeping your normal rooms usable. A fifth bedroom is most useful when the rest of the layout, storage and parking support the way you expect the home to be occupied.
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.
Understand the property's 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.
Windsor Island Resort: wider asking-price context
All property types, bedroom counts and prices in the mapped area. These asking-price figures describe the wider market, not this bedroom selection.
- For sale now
- 102
- Median asking price
- $640,000
Nearby completed sales: past 12 months
80 properties sold within half a mile in the last 12 months · median $615,000
297 Jetty Way5 bed · 5 bath · 2,283 sqft
$409,000
Sold Nov 5, 2026
1191 Aloha Boulevard6 bed · 5 bath · 3,111 sqft
$640,000
Sold Nov 2, 2026
4318 Lana Avenue5 bed · 5 bath · 2,293 sqft
$407,500
Sold Oct 30, 2026
1846 Caribbean View Terrace9 bed · 7 bath · 4,828 sqft
$730,000
Sold Oct 23, 2026
Questions about 5-bedroom homes in Windsor Island Resort
Questions when comparing a shortlist

Gaby Sadler
Property Specialist, Serhant
Compare Windsor Island Resort homes with Gaby
Tell me how you want to use your 5 bedrooms. I can arrange viewings and help you compare layouts, locations and the ownership details for your Windsor Island Resort shortlist.
Bring your priorities to the viewing
Note the room arrangement, storage and everyday destinations that matter most. Compare each home against that list and request the information needed to understand its condition and ownership responsibilities.
Explore Windsor Island Resort homes by bedroom count
View all Windsor Island Resort homes for sale.
Browse by asking price
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More on Windsor Island Resort
- 7-Bedroom Homes for Sale in Windsor Island Resort FL
- 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 $500K 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
- Homes for Sale Under $900K in Windsor Island Resort FL

























