James Donovan, Team Donovan
At Team Donovan, we specialize in helping clients navigate this unique market, whether you are looking for a vacation retreat, an investment property, or your forever home.
The Windermere Market Pulse: Stability in Luxury
While the broader national market has seen its share of fluctuations, Windermere marches to the beat of its own drum. Current market trends indicate a “balanced to seller’s” market, particularly in the luxury sector. With a median sold price hovering around $1 million to $1.3 million, Windermere is distinct from its neighbors. Inventory remains tight, with active listings often sitting around the 200-mark, meaning that when a pristine property hits the market—especially one on the famed Butler Chain of Lakes—it commands attention.
But Windermere isn’t just for the ultra-wealthy. The market is surprisingly diverse if you know where to look. Below, I’ve curated a selection of listings that highlight what your money can buy at three distinct price points in Windermere right now.
(Note: The market moves fast. Click the link at the bottom to see live availability.)
1. The Entry-Level Opportunity ($300k – $600k)
Perfect for: First-time buyers, investors, or those seeking a low-maintenance lifestyle.
Many people assume you can’t buy in Windermere for under a million dollars, but that is a myth. The entry-level market here is vibrant, dominated by upscale townhomes and cozy single-family homes in communities like Windermere Trails or Lakes of Windermere.
- What to expect: In this range, you can find modern 2-3 bedroom townhomes or condos. For example, properties like those on Ancilla Blvd or Amidship Ln often appear in the $350k – $450k range. These homes typically offer access to excellent community amenities (pools, parks) and the same A-rated schools as the multi-million dollar estates, making them a brilliant entry point into the zip code.
2. The Executive Family Home ($900k – $1.5M)
Perfect for: Growing families and professionals seeking space and amenities.
This is the “core” of the Windermere market. In this price bracket, you are looking at substantial single-family homes, often with 4 or 5 bedrooms, private pools, and 3,000+ square feet of living space.
- What to expect: Gated communities are the standard here. You’ll find beautifully appointed homes in neighborhoods like Providence or Summerport. These properties often feature three-car garages, gourmet kitchens, and mature landscaping. It’s the sweet spot for buyers who want the “estate” feel without the 8-figure price tag.
3. The Luxury Estate ($1.6M – $5M+)
Perfect for: The discerning buyer who demands privacy, exclusivity, and world-class views.
This is where Windermere truly shines. We are currently highlighting a spectacular example of this tier: 7417 Lake Albert Dr.
- Featured Listing: Priced at $1,690,000, this 6-bedroom, 7-bathroom masterpiece spans over 5,000 square feet. It represents the pinnacle of Windermere living—expansive spaces, custom finishes, and the privacy that comes with an elite address.
- Ultra-Luxury Context: For those looking even higher, the market extends into the stratosphere with estates in Isleworth and Lake Butler Sound ranging from $5 million to over $15 million, offering direct lake frontage on the Butler Chain and amenities that rival 5-star resorts.
Why Windermere?
Beyond the homes, buying here buys you into a community. It’s the Friday Farmer’s Market on Main Street, the boat days on the Butler Chain, and the golf cart parades. It is a town that feels miles away from the tourist corridor, yet is just minutes from the magic of Disney and the dining of Restaurant Row.
Find Your Place in the Sun
Whether you are looking for that smart entry-level investment or a legacy estate on the water, the inventory in Windermere changes daily.
Click here to browse our full selection of Windermere listings, filtered for every budget.
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