- 4 beds
- 3 baths
- 1,892 sqft

Windermere, Florida
Windermere Trails Homes for Sale
Compare layouts, settings and ownership costs to focus your shortlist. Review Windermere Trails homes for sale.
Homes for Sale in Windermere Trails
11 listingsBrowse Windermere Trails properties by price
Search price ranges within this area while keeping the property criteria for this page.
Recent sales near Windermere Trails
59 properties sold within half a mile in the last 12 months · median $465,000
11942 Sheltering Pine Drive5 bed · 4 bath · 3,851 sqft
$850,000
Sold Oct 23, 2026
11926 Verrazano Drive4 bed · 3 bath · 2,885 sqft
$582,000
Sold Oct 23, 2026
11446 Jasper Kay Terrace Unit 1033 bed · 2 bath · 1,442 sqft
$315,000
Sold Oct 23, 2026
8168 Boat Hook Loop Unit 7243 bed · 2 bath · 1,455 sqft
$308,000
Sold Oct 22, 2026
Windermere Trails Market Snapshot
Review public for-sale inventory and median asking price as a starting point for comparing individual homes.
- For sale now
- 11
- Median asking price
- $560,000
Buying a Home in Windermere Trails
Windermere Trails homes for sale include detached houses and townhomes, giving you different balances of private space and upkeep. We help you compare actual room arrangements, lot settings and condition alongside the maintenance obligations for each property, rather than assuming one package throughout the community.
Community Recreation and Everyday Essentials
Look beyond the floor plan to the places you will use regularly, from shared recreation to grocery shopping and routes around the neighborhood.
Community Swimming Pool
The community swimming pool offers a place for personal recreation. Consider how shared swimming facilities fit your routine when comparing homes.
Groceries and Pharmacy
Lakeside Village Center, at 7880 Winter Garden Vineland Road, provides grocery and pharmacy services for everyday errands.
A Residential Setting Along Reams Road
Local road connections include Winter Garden Vineland Road, Mizzon Drive and Silverlake Park Drive. Explore your regular routes when viewing homes.
Windermere Trails Community Map
Explore the community's location as you compare homes and plan visits to properties on your shortlist.
Schools and Your Property Search
If schools are part of your home search, Bay Lake Elementary is a local kindergarten-through-fifth-grade facility at 12005 Silverlake Park Drive, Windermere. Its location provides useful neighborhood context, but proximity alone does not establish a home's school assignment. Orange County Public Schools assigns schools by residential address, so use its official Find My School service with the exact address and relevant school year for each property you are considering. Check every address on your shortlist rather than carrying an assignment from one home to another. We can help you make this an early step in comparing properties, alongside the layout, maintenance needs and everyday routes that shape your decision.
Understand Your Ownership Responsibilities
Association responsibilities deserve attention alongside a home's physical features. The townhome association organized irrigation and landscape refurbishment in 2024, an example of shared work rather than a complete description of today's maintenance coverage. For any property you are considering, review the relevant association documents to understand who handles exterior work and landscaping, how amenity access works, and which current assessments apply. A streetlighting municipal service benefit unit was established for Phase 1 in 2012, making property-specific tax and assessment records another useful part of your review. We can help you identify the questions to raise before comparing ownership costs, without assuming that every phase or housing type has the same arrangements.
Windermere Trails Homes for Sale: Buyer FAQs
Compare more Lakeside Village communities
Explore Newbury Park homes for sale, Preston Square homes for sale, Wickham Park homes for sale, or browse the full Lakeside Village community guide. Each guide provides its own property search and community details to help you compare homes.

Gaby Sadler
Property Specialist, Serhant
Find Windermere Trails homes for sale with Gaby
Tell me your budget and plans for the home. I'll help you compare Windermere Trails homes for sale, weigh layouts, settings and ownership costs, and identify the details to resolve before you choose.
Find Your Home in Windermere Trails
Start with the homes for sale, then focus on the details that matter most to you: housing type, room layout, outdoor space and ownership responsibilities. Whether you are planning an everyday home or a second home for personal use, we can help you narrow your choices and identify questions to ask about each property. Tell us what you need from your next home, and explore the options with those priorities in mind.
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