Windermere Landing
Executive-style community with established tree canopy and private school walkway.
Live the MaxLife.
$1.4M
Median Price
$850K – $2.5M
215
Homes
$220–$400
Monthly HOA
1997
Established
Windermere Elementary School
School Zone
Search Homes for Sale in Windermere Landing
Stellar MLS · 2026-04-26 · 4 closed sales
Recent market data
Median sold
$838,750
$710K – $2075K
$/sqft
$444
Median DOM
84
days on market
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Background
A brief history
Windermere Landing was developed by M/I Homes between 1997 and 2001 as an executive-style gated community emphasizing traditional architectural design, mature landscaping, and suburban comfort. Approximately 215 homes were platted across multiple phases, with homes ranging 1,600–4,700 square feet. The developer prioritized tree preservation and planting, such that the community now has exceptional mature oak and palm canopy nearly 30 years after initial development. A significant amenity is the private walkway directly to Windy Ridge Elementary School — an unusual feature that attracted families with school-age children from day one. The community maintains an active HOA and sees steady turnover.
The feel
What it's like to live here
Windermere Landing reads as an established, mature neighborhood where trees are the defining feature. Lot sizes typically 0.4–0.8 acre with homes set back from streets, surrounded by mature landscaping buffers. Traditional architecture predominates — Georgian, transitional, and Florida-influenced styles with pitched roofs and front porches. Homes are predominantly 2–2.5 stories. The streets feel quiet and shaded; residents recognize each other. The private walkway to Windy Ridge Elementary is heavily used by families; kids bike and walk to school daily. Community amenities are modest but well-maintained: a small pool, playground, and gathering areas.
The details
What to expect
Architecture & Lots
Traditional architectural styles — Georgian, transitional, Florida influence. Homes 1,600–4,700 square feet across 2–2.5 story plans. Lots typically 0.4–0.8 acre. Most homes feature pitched roofs, front porches, and traditional elevations. Mature oak and palm canopy throughout — trees are a defining feature after 25+ years of growth.
School Walkway & Family Amenities
Private walkway directly to Windy Ridge Elementary School — residents can walk or bike kids to school without street crossing. This amenity was a primary draw during initial development and remains popular with families. Playground and community gathering spaces support family use.
Neighborhood Character
Established, mature neighborhood where most residents have lived for 5–15 years. Strong community identity and neighborhood association. Tree canopy creates shaded, quiet streets. Residents tend to know each other. Active HOA maintains standards.
HOA Rules & Fees
Monthly HOA $220–$400 depending on section. Architectural review required for exterior changes. Landscape maintenance standards enforced. Short-term rentals restricted; 30-day minimum lease standard. Fencing modifications require approval. Community pool and playground maintenance covered by HOA.
Location & Access
Gated entrance accessible via local roads in central Windermere. Nine minutes to Restaurant Row, 25–30 minutes to downtown Orlando, 15 minutes to Disney, 30–35 minutes to MCO. Convenient to schools and local amenities. Quick access to Route 429.
Community
Amenities
- Private walkway to Windy Ridge Elementary School
- Community pool and splash area
- Playground with age-separated equipment
- Mature oak and palm tree canopy throughout
- Walking trails and neighborhood parks
- Community gathering spaces and pavilion
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $220–$400 depending on section
- Architectural review for exterior changes
- Landscape maintenance standards enforced
- Short-term rentals prohibited or restricted; 30-day minimum lease
- Fencing modifications require approval
- Community pool and playground maintained by HOA
Education
School assignments
- Windermere Elementary School
- Gotha Middle School
- Olympia High School
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Market sits in the $850K–$1.5M band for homes in move-in condition. Homes needing renovation trade from $850K–$1.1M and typically need kitchen/bath updates and fresh exterior paint. Recently renovated or rebuilt homes trade $1.3M–$2.4M depending on square footage and finish level. Days-on-market average 25–40 days. The private school walkway is a strong selling point for families; homes within easy walking distance of the school entrance command slight premiums.
Active MLS Inventory
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Homes available in Windermere Landing
12 homes currently listed in Windermere Landing.
$2,899,000
4303 Isabella Cir
Windermere, FL 34786
7 bd · 6 ba · 5,122 sqft
Casabella
MLS# O6409406
$3,100 /mo
6650 Bridgewater Village Rd
Windermere, FL 34786
3 bd · 3 ba · 2,615 sqft
Vinyards/Horizons West Ph 1b
MLS# O6412833
$1,799,000
2503 Butler Bay Dr N
Windermere, FL 34786
4 bd · 3 ba · 3,297 sqft
Butler Bay
MLS# O6413242
$675,000
12826 Woodmere Close Dr
Windermere, FL 34786
4 bd · 3 ba · 2,214 sqft
Lake Sawyer South Ph 5
MLS# O6412588
$675,000
13226 Zori Ln
Windermere, FL 34786
4 bd · 2 ba · 2,521 sqft
Providence Ph 01 50 03
MLS# O6403132
$1,170,000
4474 Begonia Ct
Windermere, FL 34786
5 bd · 5 ba · 4,380 sqft
Magnolia Park Windermere
MLS# O6402227
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 6, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA