Windermere Real Estate

Windermere Real Estate

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its stunning lakes and lush landscapes, this charming town offers a unique blend of small-town warmth and modern conveniences. With its roots dating back to the late 1800s, Windermere boasts a rich history that beautifully complements its contemporary lifestyle.

One of the town's most alluring features is its breathtaking waterfront views. Windermere is surrounded by the pristine Butler Chain of Lakes, providing residents with endless opportunities for boating, fishing, and enjoying serene sunsets. The scenic beauty is complemented by a variety of parks and recreational areas, perfect for families, outdoor enthusiasts, and anyone seeking a peaceful retreat.

Windermere's vibrant community is characterized by its friendly neighborhoods, excellent schools, and a strong sense of belonging. The town hosts numerous events throughout the year, including the popular Windermere Farmers Market and seasonal festivals that bring residents together to celebrate local culture and camaraderie.

Centrally located, Windermere offers easy access to Orlando's bustling attractions, including world-famous theme parks, shopping districts, and dining hotspots. Whether you're looking for a quiet escape or an active lifestyle, Windermere provides the perfect balance.

With its idyllic charm, rich history, and vibrant community spirit, Windermere, Florida, is more than just a place to live—it's a place to thrive. Discover your dream home in this enchanting town and experience the best that Florida has to offer!

Newest Listings in Windermere

3 Beds ⋅ 2 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully maintained one-story home in the highly desirable Summerport community of Windermere! Offering 3 bedrooms, 2 bathrooms, and a versatile office/den, this home reflects true pride of ownership and is ready for its next owners. From the moment you arrive, you'll appreciate the excellent curb appeal and inviting exterior. Inside, the spacious open floor plan features elegant tray ceilings, crown molding, luxury vinyl flooring, upgraded ceiling fans throughout, a formal dining room, and a stylish modern kitchen complete with stainless steel appliances, a gas range, a large center island, and an oversized breakfast bar that's perfect for everyday living and entertaining. All appliances, including the washer and dryer, are included for your convenience. The private primary suite offers a beautiful barn door, California Closets, dual vanities, and a relaxing retreat at the end of the day. Throughout the home you'll find plantation shutters, adding both charm and functionality. Step outside to your own backyard oasis featuring a screened lanai overlooking a beautifully landscaped backyard and sparkling pool, only 2.5 years old, with the required safety door locks already in place. The home also includes a water softener, an epoxy-coated garage floor, a gas water heater, and energy-efficient double-pane windows installed in 2026. Additional updates include a new A/C installed in 2024 and the interior and exterior professionally painted in 2025. A two-car garage plus an extended driveway provide plenty of parking. Ideally located just minutes from Winter Garden Village, you'll enjoy easy access to shopping, restaurants, entertainment, major roadways, and the Florida Turnpike. Summerport is known for its outstanding amenities, scenic walking trails, parks, playgrounds, community pool, fitness center, tennis and basketball courts, and picturesque lakes. This exceptional home combines comfort, style, thoughtful upgrades, and an unbeatable location—don't miss the opportunity to make it yours!

13160 Sunkiss Loop, Windermere

4 Beds ⋅ 7 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code

Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious guard-gated community of Keene’s Pointe in Windermere. Completely reimagined with exceptional attention to detail, this residence seamlessly blends timeless architecture with sophisticated contemporary design. From the moment you enter, soaring ceilings accented by exposed wood beams, expansive porcelain flooring, designer lighting, custom millwork, and walls of glass create an atmosphere of understated elegance and warmth. Designed for both everyday living and grand-scale entertaining, the impressive great room is anchored by a striking floor-to-ceiling porcelain fireplace with custom illuminated built-ins. The gourmet kitchen is beautifully appointed with premium Viking appliances, custom European-style cabinetry, quartz countertops, an oversized center island, and a separate catering kitchen that makes hosting effortless. The luxurious primary suite offers a peaceful private retreat featuring custom-designed walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, a walk-in shower, and exceptional designer finishes throughout. Spacious guest suites provide comfort and privacy for family and visitors alike. One of the home’s most remarkable features is the expansive climate-controlled lanai, thoughtfully designed as a true extension of the interior living space. Complete with a fully equipped summer kitchen, multiple gathering areas, and panoramic golf course views, it offers the perfect setting for year-round indoor-outdoor living and unforgettable entertaining. One of the very few homes on Valhalla Drive to feature a four-car garage, this residence provides exceptional space for automobiles, golf carts, and additional storage. The pool and spa overlook the beautifully manicured fairways, creating a tranquil backdrop that captures the beauty and serenity of one of Central Florida’s premier private golf communities. Located in one of Windermere’s most sought-after addresses, Keene’s Pointe offers 24-hour guarded security, picturesque tree-lined streets, and an exceptional lifestyle centered around the renowned Golden Bear Club. Residents enjoy convenient access to top-rated schools, upscale shopping, fine dining, world-class attractions, and Orlando International Airport. This is more than a luxury home. It is an exceptional opportunity to own a beautifully renovated residence in one of Windermere’s most distinguished private golf communities.

6719 Valhalla Way, Windermere

3 Beds ⋅ 3 Baths ⋅ Windermere Trls Prcl 3 SubDv. ⋅ 34786 Zip Code

Welcome to this charming two-story townhome in the highly desirable Windermere Trails community! Featuring 3 bedrooms, 2.5 bathrooms, and 1,631 sq. ft. of comfortable living space, this home offers an open-concept main floor seamless for daily living and entertaining. The kitchen is appointed with granite countertops, stainless steel appliances, a breakfast bar, and a spacious pantry. Upstairs, you will find all bedrooms, including a private owner's suite complete with an an-suite bathroom and generous closet space. Enjoy outdoor living with your private enclosed courtyard connecting the home to the detached 2-car garage. Community amenities include a resort-style pool, splash pad, dog park, playground, and scenic walking trails. Superb location with top-rated Orange County schools nearby and easy access to Disney, Horizon West dining, and major expressways. Schedule your private showing today!

8386 Iron Mountain Trail, Windermere

3 Beds ⋅ 3 Baths ⋅ Oasis Cove I/Lakeside Village Ph 01 SubDv. ⋅ 34786 Zip Code

Welcome to Oasis Cove in Windermere, where this beautifully situated 3-bedroom, 2.5-bath residence offers something truly special—an unobstructed pond view and spectacular sunset backdrop that can be enjoyed every day from your own home. The thoughtfully designed floor plan features a downstairs primary suite, offering privacy and convenience without the need to climb stairs. Upstairs, you'll find two additional bedrooms plus a large loft, providing flexible space for a home office, media room, playroom, fitness area, or additional gathering space. One of the home's standout features is the extended rear patio overlooking the pond and walking trail. With no homes directly behind you, the setting feels open and peaceful, with beautiful water views and evening sunsets. The patio also offers the option to be fenced, subject to association approval and requirements, creating even more usable outdoor living space. The home has been well cared for with numerous improvements, including vinyl plank flooring and updated stairs (2022), bathroom/shower flooring (2023), A/C replaced in 2024, refrigerator and washer replaced in 2025, newer blinds, and updated smoke detectors. The dryer was replaced in 2023, and the water heater in 2020. Living in Oasis Cove offers the convenience of a low-maintenance lifestyle with an impressive range of services and amenities included through the association. The current owner reports the HOA includes water and sewer, trash, Spectrum services (cable/internet/streaming), pest control, landscaping, building insurance and exterior maintenance including roofs and painting, on-site management, plus access to the community pool and fitness center. And then there's the location. Oasis Cove puts you close to Walt Disney World while keeping you convenient to Windermere, major shopping, dining, entertainment, and Central Florida's attractions. Whether you're enjoying a morning walk around the pond, relaxing on the patio, or watching the sun set across the water, this home combines convenience with a setting that's difficult to duplicate.

14125 Oasis Cove Boulevard Unit 206, Windermere

3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 01 SubDv. ⋅ 34786 Zip Code

Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atmosphere, this home combines timeless charm with everyday convenience. Enjoy relaxing on the covered front porch, perfect for morning coffee, visiting with the neighbors or unwinding after a long day. Inside, the thoughtfully designed floor plan offers comfortable living spaces that are ideal for both everyday life and entertaining. The home features a galley style kitchen positioned between a cozy breakfast nook and the dining room, allowing for both casual and traditional dining options. The split-bedrooms provide added privacy. The on-suite primary bathroom features a soaking tub, dual vanities and a separate stand alone shower. The shower glass and tile were replaced in the fall of 2025. The home features real bamboo hardwood flooring in all interior areas except the kitchen, nook, bathrooms and laundry room. From the living room, open the sliders and step into your oversized patio. This patio has a generous covered area and a screened portion, allowing you to comfortably enjoy outdoor living while being protected from the Florida sun, weather and insects. The fully vinyl fenced backyard has two access gates and is ideal for pets, play or outdoor gatherings. New gutters and water heater were added in 2026, offering added peace of mind. Residents of this community enjoy access to a resort-style pool, basketball court, tennis/pickleball courts and a walking path, offering endless opportunities for recreation, relaxation and an active lifestyle. Whether you are searching for your first home, looking to downsize, or simply wanting to enjoy the charm and lifestyle that Windermere is known for, this property offers an exceptional opportunity in a highly sought-after location. Conveniently located near excellent schools, shopping, dining, theme parks and major roadways, this home offers easy access to everything Central Florida has to share. Don’t miss this opportunity - schedule your showing today.

13231 Roxboro Road, Windermere

5 Beds ⋅ 5 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code

Welcome to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulously maintained 5-bedroom, 4.5-bathroom residence offers 3,036 square feet of elegant living space designed for comfort, functionality, and entertaining. A long private driveway and charming front courtyard create a grand first impression. Inside, you'll discover spacious living and entertaining areas filled with natural light, soaring ceilings, and an inviting floor plan that flows effortlessly from room to room. Whether hosting holiday gatherings or enjoying quiet evenings at home, every space has been thoughtfully designed for comfortable living. The gourmet kitchen serves as the heart of the home and features abundant cabinetry, generous counter space, and premium appliances. Included with the sale are the kitchen refrigerator, stove/range, built-in wine refrigerator, built-in espresso machine, washer, and dryer, allowing the next owner to move in with ease. One of this home's most distinctive features is its private detached suite, located separately from the main residence with its own private entrance and full bathroom. This versatile space is ideal as an in-law suite, private guest quarters, executive home office, fitness studio, creative workspace, or media room, offering endless possibilities while maintaining privacy from the main living areas. The second story offers generously sized bedrooms and comfortable accommodations for family and guests. The staircase and upstairs bedroom carpeting were replaced approximately 1.5 years ago, while one upstairs bedroom showcases beautiful hardwood flooring, adding warmth and character. Step outside into your own private backyard retreat. The fully fenced backyard provides both privacy and security while creating the perfect setting for outdoor entertaining, pets, or simply relaxing in your own personal oasis. The sparkling swimming pool offers exceptional flexibility, as it can be operated as either a traditional chlorine pool or converted to saltwater, depending on the owner's preference. Recent upgrades include a new pool motor and complete pool filter assembly installed in 2025, and all existing pool equipment is included with the sale. The existing wicker patio furniture also conveys, allowing the next owner to begin enjoying the outdoor living space immediately. The property has been meticulously maintained, with all HVAC units receiving regular service, one HVAC unit replaced, and the tile roof professionally maintained annually, including semiannual soft washing, tile replacement, and recementing as needed to preserve both appearance and longevity. The garage features epoxy flooring, an insulated garage door, its own air-conditioning unit, built-in shelving, and a workbench, while a backyard storage shed provides additional storage. Conveniently located just minutes from top-rated schools, championship golf courses, world-class dining, upscale shopping, Disney, and the Butler Chain of Lakes, this exceptional home offers the perfect blend of luxury, flexibility, and everyday convenience. Whether you're looking for multigenerational living, a private home office, or simply an impeccably maintained luxury residence, this Windermere gem is truly move-in ready.

11434 Rapallo Lane, Windermere

3 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Luxury Pool Home in the Keene’s Pointe Golf Community – Windermere Nestled within the highly sought-after Keene’s Pointe golf community in the charming Town of Windermere, this beautifully maintained luxury pool home offers an exceptional blend of elegance, comfort, and timeless design. Just moments from the renowned Golden Bear Club and convenient to the Butler Chain of Lakes, this residence places you in the heart of one of Central Florida’s premier lifestyle communities, with nearby golf, boating, fine dining, boutique shopping, and the popular Windermere Farmers Market. From the moment you arrive, you’ll appreciate the mature landscaping, newly paved driveway, and outstanding curb appeal. Throughout the neighborhood, beautifully maintained parks, gazebos, playgrounds, walking areas, and manicured common spaces create a welcoming atmosphere that makes Keene’s Pointe one of Windermere’s most desirable addresses. Inside, elevated tray and coffered ceilings, designer lighting, and expansive transom windows fill the home with abundant natural light while creating a spacious, streamline feel. Custom window treatments, built-in features, and premium finishes are showcased throughout. The private office is beautifully appointed with custom built-in cabinetry, custom blinds, tray ceiling, recessed lighting, and an elegant designer fixture, creating the perfect work-from-home environment. Designed for entertaining, the gourmet chef’s kitchen is truly the centerpiece of the home. The magnificent oversized island—one of the largest you’ll find—offers exceptional prep and gathering space and includes a prep sink, recessed microwave, designer lighting, and custom wine bar. High-end custom cabinetry, a spacious pantry, farmhouse sink, stainless steel dishwasher, GE Monogram refrigerator and freezer, double Thermador ovens, and a six-burner Thermador gas range complete this exceptional culinary space. The adjoining family room showcases stunning coffered ceilings, a custom built-in media center, hand-blown designer light fixture, Infinity surround sound speakers, and custom draperies, creating an inviting space for relaxing or entertaining. The luxurious primary suite features tray ceilings, custom designer draperies, surround sound speakers, a spa-inspired bath with dual granite vanities, premium fixtures, an oversized glass-enclosed walk-in shower, private water closet, and an impressive customized walk-in closet. Guests will appreciate the beautifully finished secondary bedrooms and baths featuring granite countertops, quality fixtures, designer finishes, and a convenient pool bath with direct outdoor access. Step outside to your own private tropical retreat. The covered lanai overlooks a stunning lagoon-style swimming pool complete with a recessed fountain, Bose outdoor speakers, ceramic tile flooring, and screened enclosure—perfect for year-round Florida living. The lanai also provides convenient access to both the pool bath and the primary suite. Additional highlights include impact-resistant double-pane windows, expansive sliding glass doors with transom windows overlooking the pool, designer fixtures throughout, built-in office furniture, custom media center, surround sound systems, and exceptional attention to detail. Offering luxury, quality craftsmanship, and an unparalleled lifestyle, this exceptional Windermere pool home is a rare opportunity to own in one of Central Florida’s premier golf course communities.

11462 Claymont Circle, Windermere

5 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 4b SubDv. ⋅ 34786 Zip Code

Investor opportunity in the sought after Windermere Trails community! This tenant-occupied home offers immediate rental income in a high-demand location just minutes from Disney World (Magic Kingdom, Hollywood Studios, Animal Kingdom, Epcot Center and Disney Springs), Winter Garden Historic District, Doctor Philips Restaurant hub, Hamlin Town Center, Horizon West, top-rated schools, shopping, dining, and major highways. Recent updates include new interior and exterior paint, new luxury vinyl plank flooring throughout the second floor, new stair carpet, and a new refrigerator; roof is approximately 9 years old. A turnkey addition to any investment portfolio with excellent long-term appreciation potential. (Updated 2nd floor photos will be added soon to show new flooring)

8931 Lookout Pointe Drive, Windermere

2 Beds ⋅ 2 Baths ⋅ Summerport Ph 03 SubDv. ⋅ 34786 Zip Code

!!! RARE FIND PROPERTY !!! This house is better than you think... Welcome to this well maintained ONE STORY 2-bedroom, 2-bath, 2-car garage townhome located in the sought-after Summerport community. This move-in-ready home offers a spacious, open floor plan with tile flooring throughout, creating a clean and elegant look that is both stylish and easy to maintain. The upgraded kitchen featuring granite countertops, a large center island, and under-cabinet lighting. The plantation shutters and ceiling fans adding charm and functionality. The living room is overlooking at the water view. The fenced-in backyard and screened-in back porch added value to the property. The outdoor space includes mature fruit trees, making it a perfect setting for gardening, entertaining, or simply unwinding. Summerport community residents enjoy access to outstanding amenities, scenic walking trails, parks, community pool, fitness center, tennis, basketball, volleyball courts, and top rated schools. Don't miss this opportunity to own a beautiful townhome with exceptional upgrades.

13006 Sunkiss Loop, Windermere

5 Beds ⋅ 4 Baths ⋅ Providence Ph 02 SubDv. ⋅ 34786 Zip Code

Welcome to this move-in ready 5-bedroom, 4-bath home in the desirable Providence community of Windermere. This spacious home features an open-concept layout with soaring 8-foot doors, arched entryways, crown molding, recessed lighting, tile flooring, and fresh interior paint. The gourmet kitchen offers granite countertops, stainless steel appliances, a large island, abundant cabinetry, and opens seamlessly to the family room and breakfast nook. The primary suite provides a private retreat with a sitting area, walk-in closet, dual vanities, garden tub, and direct access to patio from bedroom. Three additional bedrooms are located on the main floor, while upstairs features a private fifth bedroom with built-in shelving, a full bathroom, and a spacious bonus loft perfect for an office, media room, or guest space. Enjoy Florida living on the extended paved patio overlooking the fully fenced backyard. Recent updates include both HVAC systems replaced in 2022, new roof in 2024, exterior paint in 2025, and fresh interior paint. Providence offers a community pool, playground, sidewalks, and scenic green spaces with a gazebo overlooking the pond. Conveniently located near top-rated Windermere schools, Winter Garden Village, shopping, dining, Disney, SR-429, the Turnpike, and I-4.

6208 Talaria Drive, Windermere

5 Beds ⋅ 5 Baths ⋅ Aladar On Lake Butler SubDv. ⋅ 34786 Zip Code

Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates.

800 W 2nd Avenue, Windermere

3 Beds ⋅ 3 Baths ⋅ Eden Isle SubDv. ⋅ 34786 Zip Code

Stunning Windermere Home in Gated Community with Private Boat Ramp Access! Welcome to this beautifully maintained and spacious home located in one of Windermere's desirable gated communities. Designed for both comfortable everyday living and entertaining, this home features elegant formal living and dining rooms that flow seamlessly into an expansive family room and open-concept kitchen, all overlooking a tranquil pond. Step outside to relax on the screened lanai or open patio while enjoying peaceful water views and added privacy. With no neighbor on one side and a scenic pond on the other, this premium lot offers a serene setting you'll love coming home to. Upstairs, you'll find a versatile bonus room, a study that can also serve as a fourth bedroom, two additional bedrooms, and an impressive primary suite. The spacious owner's retreat features a spa-inspired bathroom with a relaxing garden tub, separate walk-in shower, dual vanities, a large walk-in closet, and plenty of room to unwind. Come enjoy all the benefits of this area! BOAT RAMP ACCESS to Lake Speer plus a dock. Proximity to Winter Garden Village, restaurants, FL-429 toll, Turnpike, schools and theme parks. It is located about 15 minutes to Disney World and 30 minutes to Universal Studios.

6607 Earthgold Drive, Windermere

Start Your Search