Windermere Homes with Tennis Court(s) Amenities

Windermere Homes with Tennis Court(s) Amenities

Welcome to Windermere, a charming town located in Orange County, Florida. Known for its picturesque landscapes and serene atmosphere, Windermere offers a unique blend of natural beauty and modern conveniences. Nestled in the heart of the Sunshine State, this region is a haven for those seeking a tranquil and luxurious lifestyle.

If you're an avid tennis enthusiast, you'll be delighted to know that Windermere is home to numerous properties with tennis court amenities. Whether you're a seasoned player or just starting out, having a tennis court right in your backyard provides endless opportunities for recreation and staying active.

Imagine waking up to the sound of birds chirping and stepping outside to enjoy a friendly match on your private tennis court. With the convenience of having this amenity at your disposal, you can indulge in a game at any time that suits your schedule. It's not only a great way to stay fit but also an excellent opportunity to socialize with friends and neighbors who share your passion for the sport.

In addition to the homes with tennis court amenities, Windermere offers a wide range of real estate options to suit various tastes and preferences. From luxurious waterfront estates to cozy family homes, there's something for everyone in this charming town.

If you're looking for a place that combines natural beauty, a close-knit community, and the convenience of having a tennis court at your fingertips, Windermere is the perfect destination for you. Come and discover the enchanting lifestyle that awaits you in this idyllic region of Florida.

Newest Windermere Homes with Tennis Court(s) Amenities

$3,500,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere
$382,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
Welcome to Berkshire Park, a highly sought-after community where timeless style, everyday comfort, and low-maintenance living come together in the heart of Windermere. This impeccably maintained 3-bedroom, 2.5-bath townhome offers 1,644 square feet of beautifully designed living space, combining tasteful finishes with exceptional functionality. The beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area provides the perfect setting for everything from casual breakfasts to holiday gatherings, while a walk-in pantry with ample storage keeps the space organized and functional. French doors lead from the kitchen to a private, fenced patio, creating an inviting outdoor retreat for dining al fresco, entertaining guests, or simply relaxing in the Florida sunshine. Backing to conservation land with picturesque views of mature trees, the backyard offers a peaceful and private setting rarely found in townhome living. Seamlessly connected to the kitchen, the spacious living room offers a warm and welcoming atmosphere, highlighted by an electric fireplace, which is included with the sale of the home. A detached two-car garage completes the property, providing additional storage and everyday convenience. Upstairs, the spacious primary suite serves as a private retreat, complete with a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a full bathroom, offering comfortable accommodations for family, guests, or a dedicated home office. Residents of Berkshire Park enjoy an exceptional lifestyle with amenities designed for both recreation and relaxation, including a community pool, tennis courts, basketball courts, and scenic walking trails winding around tranquil ponds beneath a canopy of mature trees. The HOA further enhances the ease of homeownership by providing landscaping, structural exterior maintenance, and pest control, allowing you to spend more time enjoying everything this beautiful community has to offer. Ideally located just minutes from Walt Disney World, Winter Garden Village, Hamlin Town Center, premier shopping and dining, major roadways, and top-rated schools, this move-in-ready residence offers the perfect balance of location, lifestyle, and convenience. Whether you're searching for your primary residence, a seasonal retreat, or an investment opportunity, 12914 Vennetta Way presents an exceptional opportunity to own a beautifully maintained home in a highly sought-after Windermere community.

12914 Vennetta Way, Windermere
$675,000
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
$599,900
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
$799,500
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
$644,900
4 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere Ph 2a SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2,683-square-foot home located in the highly desirable Lakes of Windermere community! Offering the perfect blend of comfort, functionality, and Florida living, this spacious residence features an open-concept floor plan designed for both everyday living and entertaining. Thoughtfully updated for peace of mind, the home features a roof installed approximately five years ago, a new pool motor and filter, and a new water heater installed just two years ago. Inside, you'll find laminate flooring and ceramic tile throughout, along with beautifully upgraded secondary bathrooms that add style and modern appeal. Step outside to your own private backyard oasis, complete with a sparkling pool and peaceful scenic views, creating the perfect setting to relax or entertain family and friends. Residents of Lakes of Windermere enjoy low HOA fees and an exceptional array of amenities, including a clubhouse just steps from the home, tennis, basketball, volleyball, and soccer courts, three playgrounds, a lake dock with fishing access, and scenic walking trails perfect for your daily stroll. Ideally located near top-rated schools, shopping, dining, and everyday conveniences, this home is just minutes from Walt Disney World, Horizon West, Winter Garden Village, and major highways, providing easy access to everything Central Florida has to offer. Whether you're searching for your forever home or an excellent investment opportunity, this move-in-ready property offers exceptional value in one of Windermere's most sought-after communities. Schedule your private showing today and experience all that this beautiful home has to offer!

12830 Cragside Lane, Windermere
$7,500,000
6 Beds ⋅ 8 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere
$649,500
5 Beds ⋅ 4 Baths ⋅ Belmere Village G-5 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas (one living room is carpeted), beneath vaulted and 9'4"+ ceilings on the first floor. The spacious primary suite is a true retreat, featuring a garden tub, separate shower, dual vanities, private toilet closet, walk-in closet, and an adjoining sitting room with its own exterior entrance to the backyard. Four additional bedrooms deliver flexible space for family, guests, or a home office. The kitchen features stainless steel appliances. Seller offering up to $10,000 in concessions toward closing costs, rate buydown, and/or home upgrades. Major systems are well maintained: both HVAC units have been replaced (2023 and 2026), and the tile roof was resurfaced in 2023 with no major repairs since. A 2-car garage completes the home. Belmere's $130/month HOA includes a gated entrance, community pool, clubhouse, tennis courts, basketball court, sand volleyball court, playground, and fitness center — all within Windermere's top-rated school zone and minutes from the Butler Chain of Lakes and Winter Garden's Plant Street district.

11773 Bella Milano Court, Windermere
$1,049,000
3 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Timeless Charm in the Heart of Downtown Windermere. Nestled beneath a canopy of majestic oak trees on one of Windermere’s most picturesque streets, this beautifully maintained three bedroom, two and half bath residence offers the perfect blend of classic Florida charm and modern comfort. Situated on a spacious 0.38 acre fenced homesite, this exceptional property features 2,795 square feet of living space and 4,163 total square feet, providing plenty of room to live, work, and entertain. From the moment you arrive, you will appreciate the peaceful setting and inviting curb appeal that make Oakdale Street one of the town’s most desirable locations. Inside, thoughtful craftsmanship is evident throughout with custom trim work, rich stone and wood flooring, double pane windows and doors, and a warm family room centered around a natural gas fireplace. The well appointed kitchen features a natural gas range, while the expansive air conditioned Florida room offers the perfect place to relax year round as you overlook the private backyard. Car enthusiasts, hobbyists, and those needing extra space will love the 4 car garage along with the detached air conditioned building, ideal as a home office, fitness studio, art studio, workshop, guest retreat, or whatever your heart desires. Recent improvements provide peace of mind, including: Roof replaced in 2019, newer HVAC system and water heater (4 years old) and a newer well pump (9 months old). Living in the Town of Windermere is more than owning a home, it’s embracing a lifestyle. Enjoy the beloved weekly farmers market, monthly food truck nights, festive holiday celebrations, and a charming downtown just a short walk away featuring a new Italian restaurant, breakfast café, coffee shop, wine bar, tennis courts, and more. Residents also enjoy exclusive access to community boat ramps on both Lake Butler and Lake Bessie, making it easy to experience the renowned Butler Chain of Lakes. If you have been searching for a home that offers character, generous space, exceptional flexibility, and one of Central Florida’s most treasured small town lifestyles, this is an opportunity you won’t want to miss. Be sure to click on the virtual tour links.

725 Oakdale Street, Windermere
$360,000
2 Beds ⋅ 2 Baths ⋅ Summerport Phase4 SubDv. ⋅ 34786 Zip Code
Location, Location, Location! Welcome to this charming one-story end-unit townhome in the highly desirable Summerport community of Windermere! Ideally situated to Keene's Crossing Elementary School and the community's exceptional amenities. The open-concept floor plan creates a bright, spacious atmosphere, seamlessly connecting the living room, dining area, and kitchen—perfect for everyday living and entertaining. The generously sized eat-in kitchen features a breakfast bar, LG appliances, 42-inch cabinetry, granite countertops, tile flooring, an attractive art niche, and French doors that open to a covered, screened porch. The primary suite boasts a double tray ceiling, walk-in closet, dual vanities, a relaxing soaking tub, and a linen closet. The secondary bedroom is conveniently located adjacent to the guest bathroom. Additional highlights include an inside laundry room with Maytag washer and dryer included, a spacious rear-entry two-car garage, and all ceiling fans, light fixtures, and window treatments conveying with the sale. Summerport residents enjoy an impressive array of amenities, including a clubhouse, resort-style pool, fitness center, tennis courts, basketball and volleyball courts, scenic walking trails, fishing docks, playgrounds, and more. Conveniently located near SR 429, Hamlin Town Center shopping, dining, world-famous theme parks, and countless Central Florida attractions, this home truly offers the perfect combination of location, lifestyle, and value!

14250 Sonco, Windermere
$395,000
3 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code
Virtually Staged. This one has it all! Welcome home to this beautifully updated townhome in the highly sought-after Summerport community, where charm, comfort, and picturesque water views come together to create an exceptional living experience. From the moment you arrive, you'll be captivated by the home's inviting curb appeal, featuring a spacious front porch, attractive architectural details, elegant exterior lighting, and landscaping that enhances its timeless character. Inside, you'll discover a bright and welcoming interior highlighted by fresh paint, stylish luxury vinyl plank flooring throughout, and thoughtfully designed living spaces that offer both comfort and functionality. The well-appointed kitchen features crisp white cabinetry, stainless steel appliances, and ample storage, creating the perfect setting for everything from casual meals to entertaining guests. The open-concept layout flows seamlessly into the living and dining areas, while ceiling fans throughout the home provide added comfort and energy efficiency. Large windows invite natural light inside and frame beautiful views of the lake, creating a peaceful backdrop for everyday living. Additional highlights include generous garage parking and a desirable location within one of the area's most established communities. Enjoy easy access to community amenities including parks, clubhouse, community pool, tennis and basketball courts, all while coming home to tranquil water views and a welcoming neighborhood atmosphere. This exceptional Summerport home offers the perfect blend of style, convenience, and scenic beauty—don't miss your opportunity to make it yours.

5579 Somersby Road, Windermere
$15,900,000
7 Beds ⋅ 9 Baths ⋅ Keene's Point SubDv. ⋅ 34786 Zip Code
Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom-built masterpiece by Goehring & Morgan is inspired by Andrea Palladio, one of the most influential architects in history, celebrated for his elegant country houses and villas. The design draws inspiration from the diverse regions of Italy, with the finest imported materials hand-selected to ensure authenticity. Every finish and detail was thoughtfully curated, showcasing refined craftsmanship, exquisite design elements and seamless indoor-outdoor living enhanced by stunning water views. Offering 14,068 square feet of living space with an elevator on more than four acres, this remarkable residence enjoys one of the most breathtaking lake views in the area. Thoughtfully designed with Palladian principles, the rear elevation is every bit as impressive as the front, maximizing the beauty of its exceptional waterfront setting. With six bedrooms and eight-and-a-half baths plus guest house, this home offers every luxury amenity imaginable. The floor plan includes formal living and dining rooms, an open-concept kitchen and family room that flow effortlessly into the outdoor living spaces, a climate-controlled wine room, an office, a library, two bonus rooms, a fitness room and a private attached guest suite. The backyard retreat evokes the feeling of Lake Como, with picturesque sightlines, expansive lake views and covered outdoor living areas featuring fireplaces that surround the resort-style pool. Mature landscaping provides exceptional privacy while enhancing the ambiance of this extraordinary outdoor oasis. Artistry is evident throughout every space, highlighted by exposed wood beams with hand-painted details, frescoed ceilings, Old World tumbled brick floors and ceilings, inlaid marble and wood accents, barrel-vaulted ceilings, Venetian plaster finishes and countless other custom architectural elements. Within the guard-gated community of Keene's Pointe, this estate enjoys access to an exceptional lifestyle. Lake Tibet is one of the largest lakes on the Butler Chain, offering privacy and connectivity through the navigable canal system. The Butler Chain of Lakes, also known as the Windermere Chain of Lakes, consists of 13 interconnected lakes encompassing more than 5,000 acres of spring-fed water. Residents of Keene's Pointe enjoy access to the renowned Golden Bear Club, featuring a 250-acre Jack Nicklaus Signature Golf Course, a resort-style pool, tennis courts, a fitness center, multiple playgrounds and a clubhouse for private events. Combining small-town charm with unparalleled convenience, Windermere is just minutes from downtown Orlando and offers easy access to fine dining, world-class shopping, championship golf courses, top-rated schools, international and private airports, and world-famous theme parks. The Butler Chain of Lakes spans more than 4,900 acres of crystal-clear, spring-fed water and is renowned for its pristine sand bottoms, exceptional water quality and designation as an "Outstanding Florida Water."

6119 Grosvenor Shore Drive, Windermere
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