Location: Davis Shores, Windermere
Do Not Show Listings
20 OAKDALE ST, WINDERMERE, FL 34786
$1,499,00016 Days on yellowkey MLS ID: O6421265
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2188 Built: 2004 Tax: $21,535 (2025)Community: Davis ShoresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$21,535
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining, shopping, golf, and attractions * Incredible backyard * Summer Kitchen with Pizza Oven * Firepit with Stone Seating * Boathouse * Viking 6 Burner Gas Cooktop * Viking Fridge * Built in 2004 * 2 Suites on 1st Floor * Step inside to discover spacious living areas filled with natural light, soaring ceilings, and thoughtfully designed spaces perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting gathering spaces, while the generous bedrooms provide comfort and privacy for family and guests. * Outside, enjoy your own private retreat with beautifully landscaped grounds, ample outdoor living space, and the opportunity to experience everything that makes Windermere one of Central Florida's most desirable communities. Whether relaxing by the pool, hosting friends, or taking advantage of nearby lakes and recreation, this home offers the lifestyle you've been searching for. * Located within close proximity to top-rated schools, renowned golf courses, the Butler Chain of Lakes, and just a short drive to downtown Orlando and major theme parks, this is a rare opportunity to own a premier property in one of Florida's most coveted addresses.
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
81 OAKDALE ST, WINDERMERE, FL 34786
$2,300,000242 Days on yellowkey MLS ID: S5138567
11 Days Off yellowkey (back on 6/28/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4284 Built: 2001 Tax: $24,940 (2025)Community: Davis ShoresSingle Family
Taxes:$24,940
Remarks: Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step inside to an open, grand gathering space framed with natural wood beams, a gas fireplace, and a seamless flow into a chef-inspired kitchen. Featuring state-of-the-art GE Monogram appliances, a Taj Mahal quartzite island, restaurant-quality crushed ice, a 100+ bottle wine cooler, a full bar and coffee lounge, and a spacious walk-in kitchen pantry—this home invites effortless entertaining. Throughout, new wide-plank laminate wood floors set a refined, cohesive tone. Additional highlights include professional designer wallpaper in the dining room and powder bath, smart bidet in the primary bath, and a fully integrated smart-home lighting, shade, and security system. The primary suite is a private sanctuary, complete with a fully reimagined spa bath wrapped in marble and porcelain, a freestanding soaking tub, and two custom-designed closets. There are three more en suite bedrooms offering privacy and convenience. This corner-lot haven is framed by mature oak trees and newly installed landscaping and irrigation. A beautiful outdoor deck and built-in fire pit creates a cozy retreat for gatherings. Follow the canal behind the home to access the world-renowned Butler Chain of Lakes. The boathouse features an electric lift, dual Sea-Doo floating docks, and instant access to some of Florida’s most coveted waterways.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: David Warzycha (863-860-3365)
33 MAIN ST, WINDERMERE, FL 34786
$1,575,00067 Days on yellowkey MLS ID: O6406887
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2130 Built: 1961 Tax: $9,485 (2025)Community: Davis ShoresSpa: NoSingle Family
Taxes:$9,485
Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Bruce Higgins (407-883-2728)
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