Experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom-built, this one-owner Transitional Craftsman residence blends timeless architecture with exceptional livability, just steps from downtown's quaint lifestyle, multiple parks, weekly farmers market, tennis courts, playgrounds, and resident-only access to the Butler Chain of Lakes. From the moment you arrive, handcrafted timber details, natural stone accents, and inviting front porch creates a sense of warmth rarely found in newer construction. Inside, soaring wood ceilings, exposed pecky cypress beams, custom built-ins, and a dramatic floor-to-ceiling stone fireplace make this house both elegant and welcoming. Designed for everyday living as much as entertaining, the chef's kitchen features premium JennAir appliances, a striking stone cooking alcove, ceiling-height cabinetry, expansive island, generous walk-in pantry, and seamless connection to the dining and family rooms. The flexible floor plan offers six bedrooms and six baths, including two private owner's suites on the main level, making the home ideal for multi-generational living, long-term guests or one of many private spaces. Upstairs, 4 spacious secondary bedrooms and a large over-garage flex room provide endless possibilities as a home fitness studio, media room, hobby space, or home office. Outdoor living is equally impressive with a large covered porch, a wood-burning fireplace, outdoor kitchen, cabana bath, Tiki hut, circular fire pit, designed for year-round enjoyment. The backyard offers ample room to design the custom pool, allowing the next owner to create a backyard tailored to their lifestyle rather than inheriting someone else's design. Additional highlights include a newer roof (2024), commercial grade fire suppression, an oversized three-car garage with exceptional storage and workspace, and the opportunity to add a front gate for enhanced privacy off Main St. Storm hardy with underground electrical utility lines and public water. This is a home has been meticulously maintained and for buyers who appreciate exceptional craftsmanship, enduring quality, and the unique lifestyle that only Historic Windermere offers. Take a short stroll to the Downtown Redevelopment Project and shop at Victoria Jewelers, Ace Hardware, Solvino Wine Bar and Fresco's, one of Dr. Phillips' favorite Italian restaurants, adding even more charm and convenience to this incredible location.
- Built in 2013
- 3 garage spaces
- $431.33/sqft
- Lot size: 16,117 sqft
- 229 days on market
- Directions: From the intersection of Apopka Vineland Rd and Conroy Windermere Rd, head west on Conroy Windermere Rd toward Downtown Windermere. Continue approximately 3.5 miles. Turn right onto Main Street and proceed into the traffic circle to the 3rd exit. Continue on Main Street to the house located on your left.
- County: Orange
- Geo subdivision: WINDERMERE
Nearby Schools
Windermere Elem
Gotha Middle
Olympia High
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Let's get in touch!
Let's get in touch!

Laila Veronez
Corretora na Flórida 🇧🇷 🇺🇸 🇪🇸
- Source: Stellar MLS
- MLS #: O6368185
Listing updated: August 2, 2026 at 6:05PM
Listing provided by: Kari Fleck, THE REAL ESTATE COLLECTION LLC
Last checked 1 day ago
Listing provided by: Kari Fleck, THE REAL ESTATE COLLECTION LLC
Last checked 1 day ago
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