Homes for Sale Near Gotha Middle in Windermere - 27 homes

Remarks: Under contract-accepting backup offers. Short Sale. Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the 3rd Bay * Over 1 Acre * Fenced Back Yard * Mature Oaks give the Old Florida Feel * Plenty of Guest Parking and Circular Driveway * Home Theatre * Game Room * Outdoor Summer Kitchen * Large Pool * Privacy and Space between Neighbors * Golfcart Friendly * Windermere is a charming community offering plenty of walking and biking trails, Friday Famer’s Market, Monthly Food Trucks and the soon to open Marketplace on 6th & Main Street with a Wine Club & Italian Restaurant – Must see this Incredible Home to truly appreciate the Character and Quality

Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)

Listing Agent: Darrell Nunnelley (407-467-8069)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Under 20 minutes to Disney. Pool home on nearly half an acre. Space and privacy, without giving up convenience. Quick access to 429 and the Turnpike. Minutes to The Grove, Dr. Phillips Restaurant Row, golf, and daily essentials. Zoned for top rated Orange County Public Schools, including Thornebrooke Elementary. Located in Windsor Hill on the west side of Windermere, this home sits on a 0.49 acre lot, giving you real separation from neighbors and usable outdoor space that actually adds to how you live day to day. The exterior is clean and intentional with a semi circle brick paver driveway and a side facing two car garage, not the typical front facing setup. The backyard is where this property stands out. Private pool with a new cage (2024), plus additional yard space beyond the pool for pets, entertaining, and more. Inside, the home has been freshly painted with a layout that is functional and easy to live in. A fireplace anchors the main living space and adds character without overcomplicating the design. Major items are already handled with a newer roof (2021), AC/HVAC (2024), and a fully paid off solar system that offsets nearly the entire electric bill. Windsor Hill is a monitored community with a full time officer, contributing to a quieter, well kept neighborhood. For buyers looking for land, a pool, and proximity to Disney, Windermere and Dr. Phillips, this is a combination that checks all the boxes.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Under contract-accepting backup offers. Your Private Windermere Oasis Awaits * Step into a lifestyle of space, serenity, and sophisticated upgrades with this stunning 4-bedroom family estate nestled on over an acre of pristine land. Perfectly positioned to blend modern comfort with the beauty of nature, this property is a rare find for those who refuse to compromise on size or scenery. Highlights of the Estate: Breathtaking Vistas: Wake up to calming lake views from the comfort of your home, or step into the backyard for an even more expansive panorama of the water. Ultimate Move-In Readiness: Enjoy peace of mind with a brand-new roof and extensive high-end upgrades throughout, meticulously curated by the current owner. The Ultimate Entertaining Terrace: Discover an outdoor patio so grand it was originally designed to host a wedding. This space virtually doubles your living area, featuring a built-in outdoor kitchen and built-in propane firepit and a cozy integrated seating area for unforgettable evenings under the stars. A Haven for Pets: Your four-legged family members will be in heaven with a dedicated dog run and a custom dog door integrated into the screen enclosure, ensuring they enjoy the patio as much as you do. Endless Potential: With over an acre of usable land, the possibilities are limited only by your imagination. There is ample room to add an in-law suite, a professional-grade shop building, or even a private soccer field. Special Opportunity To make this dream home even more accessible

Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)

Listing Agent: Scott Howard (305-934-7727)

Remarks: Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024), windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new re-development complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Kari Fleck (407-925-5283)

Remarks: Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple structures create an unrivaled lakefront compound. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provides a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Georgian grandeur, lakefront serenity, and equestrian potential—crafted for those who demand the extraordinary.

Listing is courtesy of: DOUGLAS ELLIMAN (305-695-6070)

Listing Agent: Christine Gelman (561-723-4545)

Remarks: Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid-back lake living and walkability to town. The Town of Windermere has much to offer. Walk to the local park and tennis courts just a few blocks from your home. It’s an easy stroll or bike ride to Main Street—home to local spots like Dixie Cream, Paloma Coffee, Windermere Brewing Company, the Friday farmer’s market, and the newly updated 500 block with shops and dining. Inside, the home is both comfortable and thoughtfully updated, with travertine flooring in the main living areas and new luxury vinyl plank in bedrooms two and three—no carpet. The kitchen features a gas cooktop with vented exhaust and a brand-new all-in-one convection oven, microwave, and air fryer. The large dining room provides a pleasurable dining experience with lake views. The theater room can be a flexible space used for movies, a guest bedroom, or a game room. It can also work as an office, playroom, or just a place to sit and relax. The bright open Florida room, equipped with three full glass French doors with side panels, a wet bar and views of your outdoor lakefront oasis, opens up to the pool and overlooks the water, creating an easy space to relax or entertain. A great opportunity to enjoy the convenience of the Butler Chain lifestyle in the heart of Windermere—no HOA.

Listing is courtesy of: REVEL REALTY LLC (407-876-6448)

Listing Agent: Rebekkah Boskovich (321-438-3307)

Remarks: Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!

Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)

Listing Agent: Bo Julian (407-694-5843)