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$1,275,000
5 Beds ⋅ 3 Baths ⋅ Sandy Shores SubDv. ⋅ 34786 Zip Code
Virtually Staged. **SANDY SHORES SANCTUARY** A rare 1934 Windermere Landmark on the Butler Chain of Lakes. Rich in history and timeless charm, this one-of-a-kind canal-front home offers a rare opportunity to own a piece of Old Windermere. Privately nestled beneath a canopy of oak trees in the exclusive Sandy Shores enclave, one of Windermere's most private waterfront communities, this 5-bedroom, 3-bath residence offers direct canal access to Lake Butler. Blending historic charm with modern comfort, the home has been thoughtfully updated with a remodeled kitchen and bathrooms, 2024 HVAC systems, a 2017 roof, 2021 & 2017 water heaters, a 2020 septic drain field, and a 2026 well tank. Relax on the screened-in porch or waterfront deck while enjoying peaceful canal views, all with no HOA and just minutes from downtown Windermere, Windermere Preparatory School, championship golf, upscale dining, and Orlando's premier attractions. This is an extraordinary opportunity where history, privacy, and lakefront living converge.

12085 Sandy Shores Drive, Windermere
$1,499,000
3 Beds ⋅ 3 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
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.

20 Oakdale Street, Windermere
$749,900
4 Beds ⋅ 3 Baths ⋅ Eden Isle Boat Ramp SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked away on a quiet cul-de-sac in the highly desirable Eden Isle community of Windermere. Offering 2,665 square feet of thoughtfully designed living space on an oversized .32-acre lot, this home combines comfort, functionality, and an unbeatable location. Step inside to discover a light and inviting floor plan featuring high ceilings, crown molding, tray ceilings, spacious living and family rooms, and a seamless flow that's perfect for both everyday living and entertaining. The kitchen is the heart of the home, complete with solid wood cabinetry, ample prep space, and an open layout overlooking the family room. The spacious primary suite offers a peaceful retreat with a walk-in closet and an oversized en-suite bath, while three additional bedrooms and two full bathrooms provide plenty of room for family, guests, or a home office. Major updates provide peace of mind, including a new HVAC system, new water heater, and fresh interior paint, making this home truly move-in ready. Outside, enjoy the privacy of a large lot with plenty of room to relax, play, or create your dream outdoor oasis. Residents of Eden Isle enjoy access to a private boat ramp on beautiful Lake Speer, offering boating, fishing, and waterfront recreation just moments from home. Located in one of Windermere's most sought-after areas, you'll love being close to top-rated schools, shopping, dining, theme parks, major roadways, and everything that makes the Windermere lifestyle so desirable. Don't miss this opportunity to own a move-in-ready home in a fantastic location with private lake access and timeless appeal.

6363 Sedona Leaf Court, Windermere
$800,000
Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
RARE VACANT WINDERMERE RESIDENTIAL LOT! Build your dream home in one of Windermere’s most desirable lake-access communities, NO HOA. This rare oversized corner homesite offers a unique opportunity to create a custom residence with canal access to beautiful Lake Sawyer. Surrounded by natural beauty and serenity, the property provides an ideal setting for luxurious Florida living while remaining just minutes from top-rated schools, shopping, dining, golf, major roadways, and world-class attractions. A variance approval is already in place, providing added flexibility and value for future development. Buyers may use the seller’s existing home plan or submit their own custom design to suit their vision. With very limited vacant land remaining in Windermere, opportunities like this are increasingly scarce. Enjoy the perfect balance of privacy, elegance, and convenience in a sought-after location where custom lake-access homes continue to be in high demand. Don’t miss the chance to secure one of the few remaining vacant lots in the area and bring your dream home to life.

6606 Sawyer Shores Lane, Windermere
$1,575,000
4 Beds ⋅ 2 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
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.

33 Main Street, Windermere
$2,500,000
5 Beds ⋅ 4 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees or restrictions, you have the freedom to design and build your dream home exactly as you envision it or use the plans already available and variances approved — saving you time and expense. Offering approximately 5,516 SF of impeccably appointed living space and over 8,316 SF under roof, every detail has been curated to the highest standard of elegance and sophistication. Dramatic sightlines from the grand entry sweep through sun-drenched principal rooms to the resort-caliber outdoor living spaces beyond. The showstopping gourmet kitchen dazzles with extra-thick natural quartzite countertops, an oversized center island, pot filler, a fully integrated refrigerator and dishwasher with bespoke wood-panel cabinetry, and an oversized walk-in pantry — a culinary stage worthy of the most discerning chef. A soaring great room with designer tray ceilings and an elegant formal dining room set the scene for unforgettable entertaining, complemented by a private study and home office. The first-floor primary suite is a true sanctuary — a sumptuous walk-in closet, sculptural freestanding soaking tub, and a spa-inspired shower enclosure deliver five-star hotel indulgence at home. Upstairs, a second master suite, a spectacular lake-view recreation room with oversized balcony, three additional bedrooms, a chic loft with front balcony, and a second laundry suite elevate every aspect of daily life. Outside, a breathtaking covered lanai unfolds into a private lakeside paradise — summer kitchen, outdoor fireplace, alfresco dining, and a heated pool and spa framed by elegant paver decking and the glittering expanse of Lake Sawyer. A 4-car garage with EV charging, dual laundry rooms, impact-rated windows and doors, and bespoke designer finishes complete this extraordinary offering. Minutes from Windermere Prep School, shopping, dining and within minutes of Walt Disney World. *Images have been taken from a similar model home*

6606 Sawyer Shores Lane, Windermere