Windermere Trails Homes 

Windermere Trails, nestled in the charming town of Windermere, FL, is a captivating real estate gem that offers an idyllic blend of modern living and natural beauty. This thoughtfully designed community is renowned for its exquisite homes, attracting those seeking both comfort and elegance. The centerpiece of Windermere Trails' allure lies in its waterfront properties, where residents can relish stunning lake views and tranquil surroundings.

The neighborhood's real estate portfolio boasts an array of homes that cater to diverse preferences, ranging from spacious single-family residences to cozy townhouses. The community's unique appeal lies in its seamless integration with nature, fostering an outdoor-centric lifestyle. Windermere Trails holds the distinction of being a waterfront community, affording residents the luxury of picturesque vistas and water-based activities right at their doorstep. Moreover, the neighborhood's strategic location places it in proximity to various amenities, including schools, shopping centers, and entertainment hubs, ensuring convenience without compromising on serene living.

Windermere Trails stands as a premier real estate destination in Windermere, FL, offering an exceptional waterfront living experience. With its meticulously designed homes, breathtaking lake views, and convenient access to nearby facilities, this community encapsulates the essence of modern comfort within a captivating natural setting.

Available Windermere Trails Homes For Sale

$795,000
5 Beds ⋅ 5 Baths ⋅ O6438208 MLS
Set against a natural preserve, this Windermere home combines a flexible floor plan, thoughtful upgrades, and a backyard setting that feels removed from the everyday. Natural light fills the main living spaces, while distinctive ceiling beams in the dining room add warmth and character. A full bedroom and bathroom on the first floor provide flexible space for guests, extended stays, a private office, or everyday living. Upstairs, the spacious primary suite features two custom walk-in closets designed for exceptional storage and organization. Paid-off solar panels provide added energy efficiency without an additional solar payment, while fresh front landscaping enhances the home’s curb appeal. Step outside to a backyard framed by preserve views, local wildlife, and an added sense of privacy. The home’s mid-street position also creates a more tucked-away setting from the neighborhood entrances. Conveniently located in the Windermere and Horizon West area, the home offers easy access to shopping, dining, major roadways, and Walt Disney World. It brings together comfortable living, useful spaces, energy-conscious features, and a natural backdrop that is increasingly difficult to find.

9155 Outlook Rock Trail, Windermere

Courtesy of SERHANT

$870,000
4 Beds ⋅ 3 Baths ⋅ O6436017 MLS
Windermere Custom Interior Pool Home, 4 bedroom, 2 Primary Suites, 3 full Bathrooms New Exterior and Interior paint 2026, New Hardwood Bamboo Floors 2025, Crown Molding, Coffered Ceilings. New Heated Salt Water Pool, New Air Conditioner 2025, New Hot Water Heater 2025, Gourmet Kitchen with Hand Cut European Backsplash, Butler Pantry and Walk In Pantry, New Dishwasher 2024. Remodeled Master Shower 2023. Custom Stair Railing, New Paver Front porch and Driveway. Double Pain Windows and Extra Insulated exterior Walls. Watch Disney Fireworks from your front porch. Community Pool with Cabana, walking trials, tot lot, outdoor physical fitness areas, 3 parks, dog park with washing station. Windermere High School voted top school in USA today. Elementary school in Neighborhood, Windermere Prep 3 miles, Close to Publix, Restaurants, and Theme Parks. Butler Chain Public Boat Ramp at Keene Point Park 5 minutes.

9043 Horizon Pointe Trail, Windermere

Courtesy of CENTURY 21 CARIOTI

$999,000
6 Beds ⋅ 5 Baths ⋅ O6433721 MLS
Flexible living takes center stage in this 4,563-square-foot Windermere Trails home, where six bedrooms, four-and-a-half baths, multiple gathering spaces, and a substantial screened outdoor area create room for everyday life to unfold comfortably. The kitchen anchors the main living area with white cabinetry, a tiled backsplash, stainless-finish appliances, double wall ovens, and a large island with seating, keeping meal preparation connected to the surrounding living and dining spaces. A separate dining room and additional front room add even more flexibility downstairs, while upstairs, the expansive loft functions as a true second living area with plenty of room for recreation, hobbies, a workspace, or additional lounging space. The primary suite includes an en suite bath with dual sinks, a separate tub, and a glass-enclosed shower, while five additional bedrooms and multiple baths provide a layout with plenty of options throughout the home. One of the property’s most memorable spaces is the large screened and covered lanai stretching across the rear of the home, creating a shaded extension of the interior living areas and opening to the fenced backyard beyond. Set on a 10,400-square-foot lot in Windermere Trails, the home also offers access to visible neighborhood amenities including a community pool, playground, and covered pavilion. With generous interior square footage, adaptable living spaces, and a strong indoor-outdoor connection, this home offers a layout designed to accommodate a wide range of everyday needs.

8701 Iron Mountain Trail, Windermere

Courtesy of KELLER WILLIAMS CLASSIC

$529,000
3 Beds ⋅ 3 Baths ⋅ C7529514 MLS ⋅ 2014 BLDG.
This beautifully renovated 3-bedroom, 2.5-bath luxury home in a prime Windermere location offers the perfect blend of modern elegance, comfort, and peaceful Florida living. The bright open-concept layout creates a seamless flow between the living, dining, and kitchen areas, ideal for both everyday living and entertaining. Recent renovations include new stairs with sleek glass railings, beautifully updated bathrooms, a smart bidet toilet, and new appliances, giving the home a fresh feel, while the downstairs showcases beautiful high-gloss tile flooring that adds to the bright, upscale atmosphere. Upstairs, an additional flex/living area offers the perfect space for a home office, yoga studio, reading retreat, or lounge. One of the home’s standout features is the expansive upstairs balcony, accessible from two bedrooms and overlooking the lake, where you can enjoy your morning coffee or unwind surrounded by mature trees, birds, and nature in a wonderfully quiet setting. The home also features a two-car garage and is conveniently located near the best schools, shopping, dining, entertainment, major roadways, and everyday amenities. With its lake views, open-concept design, extensive updates, flexible living spaces, peaceful natural surroundings, and sought-after Windermere location, this move-in-ready home offers an exceptional combination of luxury, tranquility, and convenience.

8630 Powder Ridge Trail, Windermere

Courtesy of SUNCOAST CHOICE REALTY

$519,900
4 Beds ⋅ 3 Baths ⋅ O6430196 MLS
Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome to this beautifully refreshed 4-bedroom, 2.5-bath home located in the sought-after Windermere Trails community. Built in 2014, this two-story residence includes approximately 2,074 square feet of living space with an open-concept layout, abundant natural light, and tasteful updates throughout. The kitchen features granite countertops, stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. The spacious primary suite includes a walk-in closet and an ensuite bath with dual vanities, a soaking tub, and a separate shower. Additional highlights include updated flooring, fresh interior finishes, a covered lanai, and a fenced backyard. Conveniently located near shopping, dining, major highways, Disney, and top-rated schools.

11938 Silverlake Park Drive, Windermere

Courtesy of BEYCOME OF FLORIDA LLC

$475,000
3 Beds ⋅ 3 Baths ⋅ S5154426 MLS ⋅ Na BLDG.
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

Courtesy of MY REALTY GROUP, LLC.

$740,000
5 Beds ⋅ 4 Baths ⋅ O6427614 MLS
PRICE REDUCTION! 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

Courtesy of SPECIALIZED PROPERTY MANAGEMENT

$1,075,000
5 Beds ⋅ 4 Baths ⋅ S5152477 MLS
Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The gourmet kitchen showcases stainless steel appliances, a 36-inch cooktop, 42-inch cabinetry with crown molding, quartz countertops, upgraded backsplash, and a spacious walk-in pantry. The primary suite includes a large walk-in closet and a luxurious bathroom with dual vanities and a private water closet. An upgraded home theater with fiber-optic illuminated ceiling and wall panels creates a unique entertainment experience. Step outside to enjoy a beautifully landscaped, fully fenced backyard with dual gate access, a tranquil water feature, and an extended covered lanai perfect for relaxing or entertaining. Residents enjoy access to community amenities including walking trails, a resort-style pool, playground, dog park, pavilions, and fitness areas. The property is being offered partially furnished, with many of the furnishings and features shown in the photos included in the sale.

8316 Lookout Pointe Drive, Windermere

Courtesy of LA ROSA REALTY KISSIMMEE

$470,000
3 Beds ⋅ 3 Baths ⋅ O6410344 MLS
Under contract-accepting backup offers. PRICE IMPROVEMENT – EXCEPTIONAL SINGLE-FAMILY HOME VALUE IN WINDERMERE! If you've been searching for the perfect combination of location, condition, lifestyle, and value, this Windermere home deserves your attention. Situated on a desirable corner lot, this move-in-ready home offers additional outdoor space, great curb appeal, and a spacious, functional floor plan. The property has been extensively refreshed inside and out, allowing the next owner to move in and enjoy. PROPERTY HIGHLIGHTS: • Desirable corner lot with additional outdoor space • Freshly painted interior, exterior, and garage • Water softener system already installed • Freshly pressure-washed driveway and sidewalks • Spacious floor plan with convenient half bath downstairs • Versatile upstairs loft — ideal for an office, playroom, media space, or additional living area • Attractive curb appeal and move-in-ready condition The community adds even more to the lifestyle, offering walking trails, green spaces, playgrounds, a clubhouse, and community pool, with plenty of opportunities for walking, biking, exercising, and enjoying the outdoors. Conveniently located near Disney, major highways, shopping, dining, fitness centers, entertainment, and everyday conveniences, this home offers an excellent combination of accessibility and neighborhood living. Whether you're purchasing your first home, relocating to Central Florida, downsizing, or searching for an investment property, this home offers an attractive opportunity in the Windermere market. NEW PRICE. CORNER LOT. MOVE-IN READY. GREAT WINDERMERE LOCATION. Schedule your private showing today and come see everything this home has to offer. Mahmoud Mango, Realtor® The Mango Group

8266 Bryce Canyon Avenue, Windermere

Courtesy of DALTON WADE INC

$1,150,000
5 Beds ⋅ 4 Baths ⋅ O6413196 MLS
FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll immediately notice the attention to detail. Inside, exquisite marble floors, crown moulding, upgraded lighting, and a dramatic staircase create a timeless first impression. The recently renovated kitchen is truly the heart of the home. Crisp white cabinetry adorned with traditional millwork, glass display cabinets, brushed gold pendant lighting, and an oversized island blend beauty and function effortlessly. Quartzite, granite, and other fine stone finishes have been thoughtfully incorporated throughout, creating a refined yet comfortable atmosphere. Designed for both entertaining and everyday living, the home features a formal dining room, spacious eat-in kitchen, and multiple gathering spaces overlooking the pool and Lake Reams beyond. Two sets of French doors open to the covered lanai, seamlessly connecting indoor and outdoor living. With five bedrooms, four bathrooms, and a dedicated office on the main level, there is flexibility for growing families, remote work, guests, or multigenerational living. Wake up to water views and enjoy evening sunsets from your private backyard retreat featuring a sparkling pool and covered lanai. The upstairs loft also offers the same beautiful view! Residents of Windermere Trails enjoy miles of walking trails, a community pool, playground, picnic pavilion, and some of the area's most desirable schools. Located just minutes from shopping, dining, and approximately 10 minutes from Disney, this location offers convenience without sacrificing the charm and character that make Windermere so special.

8394 Lookout Pointe Drive, Windermere

Courtesy of LAKEFIELD REALTY GROUP LLC

$1,055,000
5 Beds ⋅ 5 Baths ⋅ O6413948 MLS
Experience ELEVATED LUXURY LIVING in this exceptional WINDERMERE TRAILS ESTATE, where timeless elegance, and RESORT-STYLE AMENITIES combine to create an unforgettable place to call home. Offering 5 bedrooms, 3 full bathrooms, 2 half bathrooms, a private office, expansive loft, *DEDICATED MOVIE THEATER*, sparkling POOL, and an OVERSIZED 3-car garage, this remarkable residence spans nearly *5,000 SQUARE FEET* of thoughtfully designed living space. From the moment you arrive, the beautiful TILE ROOF and impressive curb appeal set the tone for the sophistication found throughout. Evening views are made even more *MAGICAL with DISNEY FIREWORKS* visible nightly from the front of the home. Inside, you will find SOARING CEILINGS and exquisite coffered ceiling details that guide you through the elegant dining area and into the heart of the home. Designed for both entertaining and everyday living, the expansive open-concept floorplan seamlessly connects the living room, breakfast nook, and gourmet kitchen. The chef-inspired kitchen is a true showpiece, featuring stainless steel appliances, granite countertops, 42-inch wood cabinetry, an oversized center island, breakfast bar seating, and an abundance of cabinet and counter space. The kitchen has also been enhanced with newer appliances, including the refrigerator and dishwasher, offering both style and convenience. The FIRST-FLOOR PRIMARY SUITE is a luxurious retreat, complete with tray ceilings and a SPA-LIKE EN-SUITE bath featuring dual vanities, a soaking tub, walk-in shower, and generous closet space, and HIGH-END newer bidets that add an extra touch of comfort and luxury. A PRIVATE OFFICE and spacious laundry room complete the main level. Upstairs, an EXPANSIVE LOFT provides the perfect space for a GAME ROOM, LOUNGE, or SECONDARY LIVING AREA. The second level is thoughtfully designed to accommodate family and guests alike, featuring four additional spacious bedrooms, including two connected by a CONVENIENT JACK-AND-JILL BATHROOM. The crown jewel awaits behind closed doors: YOUR VERY OWN PRIVATE MOVIE THEATER, delivering a true cinematic experience without ever leaving home. Outside, discover your personal backyard oasis, where a LARGE SCREENED LANAI overlooks the STUNNING RESORT- STYLE POOL with elegant water features, creating the perfect setting for sunset gatherings, weekend entertaining, or peaceful relaxation. The pool has been *UPGRATED SALTWATER CONVERSION SYSTEM*, enhancing the swimming experience while simplifying maintenance. Beyond its luxurious finishes, the home has also been thoughtfully *UPDATED with NEW HVAC UNITS* and a *WHOLE-HOUSE WATER SOFTENER SYSTEM*, providing added efficiency, comfort, and peace of mind for years to come. Perfectly positioned in THE HEART OF WINDERMERE, this extraordinary residence is surrounded by picturesque lakes, premier dining, upscale shopping, renowned public and private schools, and offers CONVENIENT ACCESS TO DISNEY, DOWNTOWN ORLANDO, AND ORLANDO INTERNATIONAL AIRPORT. Combining *LUXURY, CONFORT, AND EXECEPTIONAL LOCATION*, this is a rare opportunity to own one of Windermere Trails' most impressive residences.

9117 Outlook Rock Trail, Windermere

Courtesy of REDFIN CORPORATION

$475,000
3 Beds ⋅ 3 Baths ⋅ O6410430 MLS ⋅ Na BLDG.
TOP RATED SCHOOLS. NO CARPET throughout the home!! Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community! This spacious two-story home features an open-concept layout with a modern kitchen offering stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas — perfect for entertaining. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bathroom. Enjoy the convenience of a rear-entry 2-car garage and low-maintenance living in one of Windermere’s most desirable locations. Community amenities include a resort-style pool, playgrounds, walking trails, dog park, and scenic green spaces. Ideally located near top-rated schools, shopping, dining, major highways, and Disney attractions. Don’t miss this incredible opportunity!

11861 Vermillion Avenue, Windermere

Courtesy of KARDOSH REALTY

$915,000
4 Beds ⋅ 3 Baths ⋅ S5145642 MLS
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.

9150 Outlook Rock Trail, Windermere

Courtesy of MOSAIC PARTNERS GROUP

$475,000
3 Beds ⋅ 3 Baths ⋅ O6389547 MLS
Under contract-accepting backup offers. 3BR/2.5BA bungalow-style home in the Windermere Trails community. This well maintained residence offers an open floor plan with high ceilings, and premium tile flooring throughout the main level. The home includes a gourmet kitchen, upgraded cabinetry in the laundry room. Upstairs, a versatile loft provides the perfect space for an office or media room, alongside a spacious master suite and two additional bedrooms. Perfectly located near Publix, dining, and banking, and zoned for A-rated schools with Bay Lake Elementary situated right at the community entrance.

8272 Bryce Canyon Avenue, Windermere

Courtesy of ON ME REALTY

$560,000
4 Beds ⋅ 3 Baths ⋅ O6371960 MLS
Beautiful 4-Bedroom Home in Windermere, FL – Prime Location and Comfort for the Whole Family! Discover this amazing home located in one of Florida’s most desirable neighborhoods – Windermere! Featuring 4 spacious bedrooms, 2 full bathrooms and a half bath, this property offers the ideal space and layout for families seeking comfort and quality of life. The home is vacant and move-in ready, perfect for those looking to relocate quickly and easily! Located in a gated community with excellent recreational amenities, you'll enjoy access to a pool, playground, sports courts, and more – all in a warm, family-friendly environment. Close to major supermarkets, local shops, hospitals, and shopping centers Easy access to main roads and highways Situated in an area with A-rated schools, ideal for families who value top-quality education If you're looking for a complete home in a highly sought-after area with everything nearby, this is the perfect opportunity. Schedule your visit today and come see this charming home in Windermere for yourself

8225 Bryce Canyon Avenue, Windermere

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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