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Illustrative covered dining terrace with a large wooden table, cushioned chairs and a landscaped Florida garden.

Windermere homes for sale: 5 bedrooms

Browse Windermere homes for sale with 5 bedrooms as listed. Compare layouts, settings and ownership details within the saved Windermere area.

Homes listed with five bedrooms

41 listings
Explore all exact-five-bedroom homes

Browse five-bedroom homes by price

These asking-price searches keep the same saved Windermere area and matching bedroom count.

Five bedrooms, with room for privacy

When comparing Windermere homes for sale with five bedrooms, look beyond the room count to how you will live together. Five bedrooms do not necessarily mean five private suites. Locate the primary bedroom and potential guest rooms on the floor plan, then consider their separation from the kitchen, gathering spaces and pool access where present. A quieter guest room may matter more than another room beside the main living area. We can help you compare those priorities, while floor plans, measurements and viewings establish whether a particular layout supports everyday privacy and comfortable visits from family.

Does the gathering space match the bedroom count?

Use these viewing checks to assess how comfortably each home handles everyday meals and visiting family.

  • Room around the dining table

    Measure for your table with chairs in use, not tucked away. Check that people can pass behind seated guests without blocking doors or the route to the kitchen.

  • Seating that suits the occasion

    Count island seats and dining seats separately. Consider where you would share a meal when family visits, and whether stools leave room for someone to cook.

  • Space to prepare and serve

    Open the fridge, oven and dishwasher during your viewing. Check door clearance, pantry storage and serving space so meal preparation does not block the room.

  • An easy route to outdoor dining

    Walk from the kitchen to indoor dining and, where present, the outdoor table. Note doors, turns and steps you would cross while carrying food and dishes.

Compare the upkeep of the home you are buying

A useful upkeep comparison starts with the property's actual systems, not a standard allowance for five bedrooms. Request roof and HVAC installation dates and service histories, water-heater details and information about drainage. Read inspection findings alongside those records, particularly where moisture, pests, wiring or plumbing need attention. Where applicable, add pool equipment, irrigation, septic design and maintenance records, or dock condition to your review. Condition and the scope of what you will maintain matter more than bedroom count alone. An inspection helps identify concerns, but it is not a warranty.

Understand the address, not just the Windermere name

A Windermere mailing address does not necessarily place a home within the incorporated town. Our broader saved search area includes town and surrounding unincorporated locations, rather than representing municipal limits or the entire ZIP code. Check the Municipality field in the Orange County Property Appraiser record, then confirm services and any school assignment for the specific address, including relevant rezoning. The Windermere property guide offers a broader starting point, while our guide to living in Windermere adds local context as you decide where to own.

Windermere area market context: all property types

All property types, including land, and all bedroom counts within the broader saved Windermere area. These are not town-only or bedroom-specific figures.

For sale now
141
Median asking price
$2,500,000

Nearby recently sold homes

9 properties sold within half a mile in the last 12 months · median $1,330,000

See all sold

Five-bedroom layout questions

Ownership, lake access and community questions

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find your Windermere home with Gaby

Tell me what you need from your next home. I can arrange viewings and help you compare 5-bedroom layouts, settings and the property-specific ownership details to check before buying.
+1 (407) 490-0475realty@thetopvillas.com

Find the five-bedroom home that fits your life

Start with the five-bedroom listings above and tell us which layouts, private spaces and ownership details matter most to you. If the water is part of your plans, explore our Windermere lakefront guide alongside your shortlist. We can help you compare the details that shape your decision, or you can explore a wider selection through our general property search below.

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