- 5 beds
- 5 baths
- 2,494 sqft

5-Bedroom Homes for Sale in Windsor Hills Resort FL
Find 5-bedroom homes for sale in Windsor Hills Resort. Compare current listings, layouts and ownership details within the mapped area.
Browse 5-bedroom homes in Windsor Hills Resort
7 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 Hills Resort bedroom search
This search uses the mapped Windsor Hills Resort area from our main guide. It does not extend across the wider Kissimmee market or into other Windsor communities.
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 Hills home and its setting
Use the home's position within Windsor Hills to compare the entrance, parking and routes you expect to use. Review private outdoor space separately from shared recreation, and establish the access arrangements for the particular property. A condo, townhome and detached house can suit different routines even when they report the same bedroom count.
Understand the property's ownership responsibilities
Windsor Hills has a master association and different property associations. Identify those applying to the address and review current assessments, insurance, planned work and maintenance allocations. Keep interior upkeep, exterior or building responsibilities and shared facilities distinct. Confirm proposed personal or rental use and any management terms for the actual home.
Windsor Hills 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
- 55
- Median asking price
- $395,000
Nearby completed sales: past 12 months
103 properties sold within half a mile in the last 12 months · median $435,000
7677 Fitzclarence Street3 bed · 3 bath · 1,440 sqft
$393,000
Sold Nov 6, 2026
7772 Basnett Circle6 bed · 4 bath · 2,812 sqft
$680,000
Sold Nov 4, 2026
2774 Almaton Loop Unit 1043 bed · 2 bath · 1,390 sqft
$240,000
Sold Oct 28, 2026
7759 Tosteth Street6 bed · 4 bath · 2,812 sqft
$601,000
Sold Oct 26, 2026
Questions about 5-bedroom homes in Windsor Hills Resort
Questions when comparing a shortlist

Gaby Sadler
Property Specialist, Serhant
Compare Windsor Hills 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 Hills 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 Hills Resort homes by bedroom count
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More on Windsor Hills Resort
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- 3-Bedroom Homes for Sale in Windsor Hills Resort FL
- 4-Bedroom Homes for Sale in Windsor Hills Resort FL
- 6-Bedroom Homes for Sale in Windsor Hills Resort FL
- Homes for Sale Under $300K in Windsor Hills Resort FL
- Homes for Sale Under $400K in Windsor Hills Resort FL
- Homes for Sale Under $500K in Windsor Hills Resort FL
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