Windermere Homes with Windermere High School High school

Windermere Homes with Windermere High School High school

Welcome to Windermere, Florida—a picturesque town nestled in Orange County that perfectly blends small-town charm with modern conveniences. Known for its stunning lakes and lush landscapes, Windermere offers a serene lifestyle that is hard to resist. With its close-knit community, residents enjoy a tranquil atmosphere while still being just a short drive away from the bustling city of Orlando.

Windermere is renowned for its beautiful homes, many of which boast breathtaking views of the surrounding lakes and nature. The architectural styles range from Mediterranean-inspired villas to contemporary designs, ensuring that there is something for everyone. Families will find Windermere particularly appealing due to its excellent educational opportunities, including the highly-rated Windermere High School. Known for its commitment to academic excellence and a wide array of extracurricular activities, this school is a cornerstone of the community, making it an ideal choice for families looking to settle down.

Beyond the exceptional schools, Windermere offers a plethora of recreational activities. Residents can enjoy outdoor adventures at the nearby parks, take leisurely strolls along scenic walking trails, or partake in water activities on the lakes. The town also hosts various community events throughout the year, fostering a strong sense of belonging among its residents.

If you’re considering a move to Windermere, you’ll find a welcoming community, beautiful homes, and a vibrant lifestyle waiting for you. Discover the charm of Windermere, where your dream home and a fulfilling life await!

Newest Windermere Homes with Windermere High School High school

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

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

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

3 Beds ⋅ 2 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code

Welcome to 7222 Still Pond Lane, a beautifully maintained 3-bedroom, 2-bath home offering 2,066 square feet of thoughtfully designed living space in the highly desirable Ashlin Park community. Built in 2016, this home combines modern finishes, excellent condition, and an outstanding location in one of Windermere's most sought-after neighborhoods, where homes are rarely available. Inside, the home has been exceptionally well cared for and is truly move-in ready, allowing its next owner to settle in with confidence. A a functional split floor plan layout designed for both everyday living and entertaining, complemented by granite countertops and engineered hardwood floors bring warmth and character to the main living areas. Step outside to a fully fenced backyard that provides privacy and space to relax, play, or entertain. Ashlin Park residents enjoy a variety of community amenities, including a resort-style pool, clubhouse, and playground, all contributing to the neighborhood's welcoming atmosphere. The location is hard to beat, with convenient access to shopping, dining, major roadways, and the growing Horizon West area. Zoned for Windermere High School and Horizon West Middle School, this home offers an exceptional combination of quality, convenience, and community. If you've been waiting for an opportunity to own in Ashlin Park, this is one you won't want to miss.

7222 Still Pond Lane, Windermere

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

6 Beds ⋅ 8 Baths ⋅ Bellaria SubDv. ⋅ 34786 Zip Code

Exceptional custom estate in the exclusive guard-gated community of Bellaria featuring 6 bedrooms, 7 full bathrooms, 1 half bath, and a floor plan designed for both everyday living and entertaining. Positioned with pond views and no front neighbors, this residence has been recently painted inside and out and offers quality craftsmanship throughout. The main living areas showcase travertine flooring, while the gourmet kitchen is appointed with custom Bosby cabinetry, stone countertops, a paneled built-in refrigerator that blends seamlessly with the cabinetry and an oversized walk-in pantry with direct access to the interior laundry room. The custom Bosby cabinetry continues into the family room, creating a cohesive, high-end design. The thoughtfully designed layout provides exceptional privacy, with no bedrooms sharing a common wall. The spacious primary suite is located on the first floor fqacing the pool/backyard with a spaccious walk-in closet, upstairs you'll find 2 bedrooms and a dedicated movie theater, with the theater seating conveying with the sale. The outdoor living space is designed for year-round enjoyment, featuring a resort-style pool, covered lanai, summer kitchen, and a bedroom overlooking the pool, ideal for guests or multigenerational living. Mature privacy hedges surround the backyard, creating a secluded outdoor setting. Located just minutes from Winter Garden Village, major highways, top-rated schools, restaurants, shopping, and Orlando's world-class attractions, this exceptional home offers luxury, privacy, and convenience in one of Windermere's most desirable communities.

13250 Bellaria Circle, Windermere

4 Beds ⋅ 4 Baths ⋅ Casa Del Lago-Replat SubDv. ⋅ 34786 Zip Code

Welcome to this impeccably designed, all-on-one-floor luxury custom home located in one of the most sought-after gated communities of Windermere, Casa Del Lago, where timeless Mediterranean architecture meets refined Florida living. This exceptional home offers four bedrooms and four full bathrooms and is thoughtfully designed with custom details, designer features, modern décor, graceful indoor-outdoor flow, and resort-style outdoor living. From the moment you arrive, the home makes a lasting impression with its classic barrel tile roof, stone-accented exterior, brick-paved driveway, lush landscaping, and charming private courtyard entry. Inside, you are greeted with style and elegance, welcomed by soaring ceilings, elegant archways, rich crown molding, designer lighting, beautiful travertine flooring throughout the main living areas, and hardwood flooring in the bedrooms. The bright and inviting formal living and piano room features tray ceiling details and expansive sliding glass doors that open to the covered lanai and pool area, creating a seamless connection between indoor comfort and outdoor relaxation. The open layout flows beautifully into the family room, making it ideal for everyday living and entertaining. The family room showcases a beautiful onyx wall with an electric fireplace and built-in surround sound system, creating a warm and elegant focal point for the home. The gourmet kitchen offers granite countertops, custom cabinetry, premium appliances, a built-in oven, microwave, refrigerator, dishwasher, disposal, gas cooking, kitchen exhaust hood, and a water filtration system. It connects to the butler’s area, which leads to the formal dining room. The private owner’s suite is thoughtfully separated from the secondary bedrooms, offering a sense of personal sanctuary and a peaceful retreat with generous space and a luxurious bathroom featuring dual vanities, a garden tub, and a frameless glass shower. Additional bedrooms provide comfort and flexibility for family, guests, or a home office. The home also features custom built-in closet shelving, providing excellent storage and organization. The outdoor living area is truly special, featuring a screened covered lanai with rich wood ceiling detail, built-in surround sound system, gas grill, outdoor vent hood, dining area, and lounge space overlooking the sparkling heated pool and jacuzzi/spa. Surrounded by tropical landscaping, palm trees, privacy walls, fencing, water features, and multiple seating areas, the backyard creates a private resort-style setting perfect for relaxing, entertaining, and enjoying beautiful Florida evenings — with the added charm of being close enough to enjoy Disney-area fireworks. Additional upgrades include a Tesla charger connection and thoughtful custom features throughout the home. This home offers convenient access to Disney theme parks, world-class entertainment, shopping, restaurants, major highways, and some of the area’s top public and private schools, including nearby Windermere Preparatory School. A rare opportunity to own a custom luxury home with timeless design, elegant finishes, privacy, and exceptional indoor-outdoor living in one of Central Florida’s most desirable locations. This home is truly a dream come true.

12417 Montalcino Circle, Windermere

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