Windermere Homes For Sale & Real Estate - 313 homes

Remarks: Welcome to low maintenance living in the heart of Windermere’s sought after Vineyard Square community. A modern townhome built in 2017 with an OPEN FLOOR PLAN designed for easy everyday living and entertaining. Step inside to a bright and airy oasis with soaring ceilings on the main level, tile flooring throughout the first floor living areas, and generous windows that fill the home with natural light. At the heart of the home, the kitchen features stylish, spacious countertops, ample cabinet storage, and a large functional island that flows seamlessly into the living and dining spaces, perfect for gatherings or a quiet night in. Upstairs, all three bedrooms are thoughtfully arranged to maximize privacy and comfort, with a spacious primary suite, well sized guest bedrooms, and convenient double-vanities in both bathrooms . With 3 beds and 2.5 baths, this townhome offers flexible spaces for a HOME OFFICE, guest room, or media space to fit a variety of lifestyles. Enjoy true Florida indoor/outdoor living with a PRIVATE COURTYARD style outdoor area off the main living space, ideal for grilling, container gardening, or relaxing with morning coffee. Hoa provided LAWN MAINTENANCE means you can spend more time enjoying your home and less time on yard work, creating a truly LOCK AND LEAVE lifestyle. Residents of Vineyard Square enjoy outstanding COMMUNITY AMENITIES including a COMMUNITY POOL, CABANA, TOT LOT PLAYGROUND, and PET PARK areas, giving you resort style recreation just steps from your front door. The tree lined streets and thoughtfully planned common areas create a welcoming neighborhood feel that is perfect for evening walks or bike rides. The location is a major highlight, placing you minutes from world class CENTRAL FLORIDA ATTRACTIONS including WALT DISNEY WORLD, UNIVERSAL ORLANDO RESORT, and ORANGE COUNTY NATIONAL GOLF CENTER AND LODGE, along with nearby shopping and dining. You are also a short drive to WINTER GARDEN VILLAGE with its outdoor events, festivals, and retail, plus access to walking and biking at TIBET BUTLER NATURE PRESERVE, making this an ideal base to enjoy the best of the Orlando area. With it's modern construction, appealing perks, and community feel, this move in ready townhome offers an exceptional blend of comfort, convenience, and lifestyle in the heart of Windermere.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Dustin Bragg (407-970-3279)

Remarks: Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartz countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026). This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Sharon Brandt (407-310-3623)

Remarks: Under contract-accepting backup offers. Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level. At the heart of the home is an expansive gourmet kitchen appointed with premium Thermador appliances and granite countertops, perfectly balancing form and function. The kitchen opens effortlessly to the grand family room, creating an ideal setting for both everyday living and entertaining. Soaring ceilings and clean, contemporary finishes throughout the residence underscore the home’s elevated design. Additional highlights include a dedicated wine room, ideal for showcasing a curated collection, and a private office suite that offers a quiet, productive retreat. Outdoor living is equally impressive, featuring a resort-style pool and spa, an outdoor kitchen, and a fireplace—designed for year-round enjoyment. Set on a generous 2.16-acre cul-de-sac lot, the property offers sweeping views of the ski-able Lake Cypress and includes a private dock capable of accommodating jet skis, delivering a truly exceptional waterfront lifestyle.

Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)

Listing Agent: Monica Lochmandy (407-230-6888)

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: Casa del Lago gated community in Windermere, Florida. Exquisite 4 bedroom/4.5 bath luxury residence showcasing exceptional craftsmanship and high-end finishes throughout. As you arrive you are welcomed by a circular driveway and quaint courtyard entrance. The first floor boasts a formal dining room,and a spacious gathering room anchored by a stunning stone two-sided fireplace. A dedicated 1,275-bottle wine cellar with tasting and corking areas elevates the home’s entertainment appeal. The gourmet kitchen features Thermador appliances, a generous island, a walk-in pantry, and a Butler’s area—perfect for hosting on any scale. A private primary suite offers direct access to the patio and pool, along with a spa-inspired en-suite bath. This retreat features stone wall accents, a luxurious indoor shower plus an outdoor shower with dual rain heads, and an expansive, custom-designed closet with three separate areas and built-in shelving.Also on the main level are two additional en-suite bedrooms, one with a private entrance from the front courtyard—ideal for guests or multi-generational living. A large laundry room with built-in refrigerator and freezer and additional storage room adds convenience and functionality. The gathering room with built-in entertainment center and 16ft sliding glass doors opens seamlessly to the private outdoor patio with summer kitchen, gas fireplace, and screened resort-style swim-spa, as well as sitting area with fire pit, creating an effortless indoor-outdoor flow.Upstairs, a spacious club room awaits—complete with built-in entertainment center and abundant storage—perfect for gaming, media, or relaxed lounging. The upper level also includes a fourth en-suite bedroom with walk-in closet and a large closet for holiday storage. This home also has a 3-car split garage, hardwood flooring, wood paneled and beamed ceilings, plantation shutters, and custom details throughout. A rare blend of elegance, comfort, and thoughtful design—crafted for luxurious everyday living and exceptional entertaining. Located close to shopping, dining, top-rated public and private schools, expressways and tourist attractions, this home has everything you are looking for. Call for your private viewing today.

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Teresa Stewart (407-493-3057)

Remarks: AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME! Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting, and custom window blinds throughout. The gourmet kitchen is equipped with stainless steel KitchenAid appliances, granite countertops, and a stylish backsplash. Laminate floors and LED-lit cabinetry enhance the home’s modern elegance. Outside, enjoy a fully renovated fence, a paved terrace, and stone walkways, creating the perfect outdoor living space. Located just minutes from Disney parks, restaurants, and major shopping centers, this home is a prime opportunity for savvy investors or first-time buyers ready to make this their dream home. Don’t miss out on the chance to combine financial stability with the unmatched appeal of Disney-area living!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Mariana Rondon (407-607-3558)

Remarks: Luxury Pond-View Home in Keene’s Pointe – Windermere Located in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom residence offers an exceptional combination of space, comfort, and scenic surroundings. The home features a thoughtfully designed floor plan with a private den/office, formal living and dining rooms, and expansive living areas perfect for both everyday living and entertaining. Large windows and sliding doors allow natural light to flow throughout the home while showcasing the peaceful pond views. The spacious kitchen opens to the family room and overlooks the outdoor living area, creating the perfect setting for gatherings and family time. Step outside to enjoy your private screened pool and spa, ideal for relaxing while enjoying the tranquil waterfront setting. Additional highlights include: 5 spacious bedrooms 4 full bathrooms Private den / home office Formal living and dining rooms 3-car garage Beautiful pond views Private pool and spa Brand new roof (2024) Situated in the prestigious Keenes Pointe community, residents enjoy 24-hour guard-gated security, tree-lined streets, and proximity to world-class golf, shopping, dining, and top-rated schools. This is a rare opportunity to own a spacious home with water views in one of Windermere’s most desirable communities.

Listing is courtesy of: AMERICAN HORIZONS REALTY (407-466-0256)

Listing Agent: Martonio Pinto (407-466-0256)

Remarks: Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and recreation. With its flexible layout, multiple living spaces, and resort-style amenities, it offers the perfect setup for multigenerational living without compromise. From the moment you arrive, you’ll sense the pride and care that has gone into crafting this one-of-a-kind residence. Meticulously expanded and improved over decades, the home features five generously sized bedroom suites, including a luxurious owner’s retreat with fine finishes and boutique-style custom closets. Whether accommodating extended family, live-in help, or guests, everyone enjoys their own private space. For culinary enthusiasts and entertainers alike, two full gourmet kitchens—one upstairs and one downstairs—provide unmatched convenience and versatility. Host formal holiday gatherings, casual poolside brunches, or multiple family dinners with ease. Both kitchens are thoughtfully appointed with high-end appliances and stylish finishes that reflect the home’s refined character. The garage is a masterpiece in itself, built to accommodate your most ambitious lifestyle. Store your 45-foot Prevost RV with full hookups—sewer, water, cable, and power—or tuck away your 50-foot center console, classic cars, or workshop equipment in the four additional bays. Whether you’re an adventurer, collector, or weekend explorer, this space is a rare find in residential real estate. Outdoor living takes center stage. A private beach invites sunbathing and quiet reflection by day, while the oversized gas fire pit becomes a natural gathering point at night for family, friends, and unforgettable moments. The resort-style pool area includes a gas fireplace and summer kitchen, perfect for year-round entertaining. Speakers are integrated throughout both indoor and outdoor spaces, creating a seamless atmosphere of leisure and luxury. Inside, modern comforts abound: three zoned A/C units with Nest thermostats, two tankless gas water heaters, and a finished storage area above the garage offer functionality and peace of mind. Located in the highly coveted Town of Windermere, residents here enjoy more than just natural beauty—they cherish a community rooted in tradition, charm, and quality of life. Walk to the Farmer’s Market, explore local parks, or attend beloved events like food truck nights, craft festivals, and holiday parades. The town library, family-owned shops, and quaint cafes further enhance the walkable lifestyle. Minutes away, you’ll find world-class golf, upscale shopping, fine dining, and easy access to highways leading to Orlando’s top attractions, excellent schools, and international airport. As an added value, completed architectural plans by Dirk Arace of Arace Designs are available, offering an exciting opportunity to customize or expand the estate with one of Central Florida’s most respected designers. Whether you’re seeking a private lakeside sanctuary, a home for generations, or a place to live your dream by the water, this Windermere gem is truly extraordinary. Listing agent is owner of the property.

Listing is courtesy of: SERENDIPITY REALTY LLC (407-790-1473)

Listing Agent: Sean Oakley (407-790-1473)

Remarks: Under contract-accepting backup offers. Completely renovated and thoughtfully reconfigured in 2023, this stunning 4-bedroom, 3-bath home is located in the highly sought-after, 24-hour gated and guarded community of Keene’s Pointe. Designed for modern living, the home features an open and refreshed layout with new flooring throughout and elegant paneling details that elevate the interior design. The expansive primary suite has been completely reimagined, showcasing a beautifully reconfigured spa-like bathroom and an oversized custom primary closet. The kitchen is equipped with premium appliances including a Thermador panel-ready refrigerator, KitchenAid gas stove, KitchenAid oven/microwave combo, and panel-ready dishwasher — all new in 2023. A new washer and dryer were also added for convenience. Major system upgrades provide peace of mind, including a new roof (2023), new HVAC units (2022 & 2023), and a new hot water heater (2023). The exterior was freshly painted in 2024. An impressive accordion-style glass door seamlessly connects indoor and outdoor living spaces, opening to a spacious, fenced backyard with no rear neighbors — offering both privacy and room to entertain. Keene’s Pointe is home to the Golden Bear Country Club, featuring an 18-hole Jack Nicklaus-designed golf course, restaurant, and tennis facilities, delivering an exceptional lifestyle in one of the area’s premier communities. Conveniently located near shopping, dining, major expressways, and world-renowned tourist attractions, as well as top-rated public and private schools, this turnkey home blends luxury updates, privacy, and prime location — a rare opportunity in Keene’s Pointe.

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Jay Stewart (407-913-2677)

Remarks: Under contract-accepting backup offers. Welcome to the highly sought-after community of Summerport in Windermere! The large, inviting FRONT PORCH leads to the decorative GLASS ENTRY DOOR that welcomes you to this FRESHLY PAINTED 2-bedroom, 2.5-bath townhome featuring WOOD FLOORING throughout the main level. The kitchen offers abundant WOOD cabinetry for storage, GRANITE countertops, and a cozy dinette area that flows seamlessly into the dining and living spaces, creating an atmosphere perfect for both everyday living and entertaining. A CONVENIENT HALF BATH is also located on the first floor. Step through the FRENCH DOORS to enjoy the SCREENED and PARTIALLY COVERED LANAI, complete with brick pavers, full fencing, creating a private outdoor retreat, ideal for relaxing, barbecuing, or entertaining guests. The home also includes a rear-entry two-car garage with private alley access. Upstairs you’ll find two generously sized bedrooms. The primary suite features a WALK-IN closet and an ENSUITE BATH with dual sinks. The second full bathroom is conveniently located adjacent to the second bedroom. NEW ROOF 2022 and NEW AC 2023 SUPERB LOCATION in this amenity-rich community. This home is located STEPS FROM YOUR FRONT DOOR to a tranquil, fish stocked POND, LAKE, DOCK, RESORT-STYLE POOL, AMMENITIES CENTER, TENNIS COURTS and FITNESS CENTER. In addition, your picturesque setting is just steps away from WALKING TRAILS, BEACH AREA, VOLLEYBALL, BASKETBALL and so much more. There are many green spaces and lakes throughout the community. Just a short stroll away, you'll find Foxtail Coffee, Marco’s Pizza, Kelley’s Ice Cream and a Vet. EASY ACCESS to MAJOR ROADWAYS such as the 408, 429, and the Turnpike. Restaurants, Grocery stores and shopping are all nearby. Also, in close proximity to A-RATED SCHOOLS, including Keene’s Crossing Elementary within walking distance, Bridgewater Middle and Windermere High School just a short drive away. In addition, private options such as Windermere Preparatory School and Foundation Academy are also very close by. Minutes from DISNEY and all other theme parks. You are moments away from and all the magic Central Florida has to offer! The HOA takes care of the Exterior maintenance, including future roof replacements every 10 years, allowing for a truly low-maintenance lifestyle. WASHER and DRYER are included. This move-in-ready home offers the perfect blend of peaceful surroundings and everyday convenience**Some photos have been VIRTUALLY STAGED**Don't forget to check out the video!

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Sandy Jones (407-929-7999)

Remarks: Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in the grand foyer that immediately sets the tone for the home’s impressive design. The first floor features a versatile bedroom with a full bath, perfect for guests or multi-generational living, along with a formal dining room that can easily serve as a home office. The beautifully remodeled kitchen is a true showpiece, boasting 42” warm white -colored cabinetry, granite countertops. A walk-in pantry, vented built-in microwave, and two full double ovens provide both convenience and functionality. The spacious island is illuminated with elegant pendant lighting, while a butler’s pantry conveniently located between the kitchen and garage adds extra storage and practicality. The home also features brand-new flooring, adding a fresh and modern touch throughout. The main living areas are finished with neutral tile, while the stairwell and entire second floor—including all bedrooms—showcase new Lifeproof wood-look luxury vinyl flooring. The expansive owner’s suite serves as a private retreat, offering two large walk-in closets, a relaxing soaking tub, separate shower, and dual vanities. Each additional bedroom also includes walk-in closets and TV cable feed-throughs for added convenience. Upstairs you’ll also find a spacious bonus/media room pre-wired for A/V components, perfect for movie nights, gaming, or entertaining. Step outside to your private outdoor oasis, featuring a screened lanai and sparkling saltwater pool with a sun shelf, surrounded by elegant glass mosaic tiles in soothing ocean-blue tones. The property has also been recently enclosed with a newly installed vinyl privacy fence, creating the perfect setting for relaxing afternoons or weekend barbecues. This home is not only beautiful but also energy efficient, featuring R-38 insulation, a 15 SEER HVAC system, and a hybrid water heater, helping keep utility costs low while earning an ENERGY STAR rating. Located in the highly desirable Windermere Trails community, surrounded by scenic green spaces and ponds, and just minutes from shopping, dining, and top attractions. Residents enjoy exceptional amenities including a lakeside pool with splash pad, playgrounds, and a running and biking trail. Don’t miss the opportunity to make this stunning home yours. Schedule your private showing today and experience the lifestyle it offers.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Andrea Munoz (407-989-2021)

Remarks: Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water Softener, Built-Ins, and Newer Roof. Three stylish transom windows located in the Living Room allow lots of Natural Light. Granite counters and solid wood cabinetry in the kitchen. Butler's pantry off the Dining Room. A relaxing spa is located on the screened-in Lanai with custom pavers. This home has paid attention to detail, finish, form, and function. The Lakes of Windermere community is known for promoting a well-maintained, safe, and family-friendly environment with many acres of natural beauty amidst great live oaks, pine trees, and beautiful natural habitats. The oak tree-lined community and combination of outdoor amenities rival the best of Orlando’s communities. Our neighborhood features include: A picturesque pier located on Lake Sawyer is perfect for fishing, relaxing, or nightly star gazing. This community features a large pool and sun deck perfect for those hot summer days. There is also a kitchen available for use by reservation. Tennis. Volleyball. Basketball. Gazebo. 3 Playgrounds. Whatever your favorite activity is, the Lakes of Windermere will have a place for you to enjoy the beautiful sunshine of Central Florida. (Room measurements are approximate, Buyer to verify) Home Warranty to be provided by Seller.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Sean Flatley (609-208-8204)