How Windermere Quietly Became What It Is today
Blog Author: Jeffrey Funk | Co-Founder, The Funk Collection, Brokered by eXP Realty | ICON Agent
It’s a little like driving past the house where childhood memories were made. The street feels familiar, but things look different. Bigger. Fuller. More layered.
Looking back at Windermere’s early days brings that same feeling and raises a simple question worth asking:
What did real estate here actually look like in the beginning?
A Town Before the Town
In the late 1800s, Windermere was barely a village. Fewer than 100 people lived here, and the railroad had only just arrived. There were no subdivisions, no tidy blocks of homes, and no clear sense yet of what the town might become.
Land ownership existed, but records were limited. Deeds mark when land changed hands, while much of what we know about early residents comes from directories, newspapers, and old meeting minutes. Together, they show a community taking shape slowly, guided more by practicality than planning.
A Small Community, Clearly Defined
Records from the late 1880s list residents by name and occupation. A conductor. A sawyer. An engineer. A postmaster. Windermere wasn’t a destination or a resort town. It was a working community, closely tied to the railroad and the surrounding land.
Streets we recognize today, including West Second Avenue, were already taking shape, though on a much smaller scale. A handful of homes. Open land. A pace of life that moved far slower than it does now.
When Value Began To Change In Windermere
For a long time, Windermere real estate stayed modest, even along the lakes.
By 1975, lakefront property here was priced around $27,000 and was often hard to sell. Within just a few years, that number climbed to $80,000, then $125,000. By the early 1990s, lakefront pricing had reached $300,000.
By the late 1990s and early 2000s, the shift was unmistakable. Homes along Lake Butler and South Main Street sold for $800,000 to $900,000, often purchased for the value of the property rather than the structure itself. Some older homes were torn down and replaced, signaling a clear change in how Windermere real estate was viewed.
Today, lakefront living in Windermere is valued for its setting and access to the water. In 2025, waterfront homes sold at prices from around $1.5M to more than $10M, numbers that would have been hard to imagine in the town’s earliest days.
The windermere Sprawl
Over time, the real estate landscape around Windermere changed too.
What had once been open land gradually filled in with planned neighborhoods, new street patterns, and communities built for a growing population. Communities like Keene’s Pointe, Glenmuir, Belmere Village, and Tilden’s Grove began taking shape in the late 1990s and early 2000s, reflecting a more organized approach to growth.
That shift didn’t happen by accident. It marked a move toward more intentional planning, with defined neighborhoods, shared amenities, and a different rhythm of daily life.
Growth, without losing its identity
Driving along Main Street in downtown Windermere today, there are so many glimpses of a time gone by. The dirt side roads, the towering Oak trees, and the preservation of historic structures like the Town Hall and the Cal Palmer Memorial building has retained much of that classic, small-town feel. The contrast of old and new with original homes and modern builds show us that growth and nostalgia can co-exist.
Curious how Windermere homes look today?
Browse available Windermere homes and see how the story continues.
Historical details referenced from Windermere Among the Lakes: The Story of a Small Town by Carl Patterson.
Posted by Jeffrey G. Funk P.A. on
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