Windermere Homes with Playground Community Features

Windermere Homes with Playground Community Features

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County that beautifully blends serene living with vibrant community life. Known for its stunning lakes, lush landscapes, and charming small-town feel, Windermere offers a unique lifestyle that attracts families, professionals, and retirees alike. With its proximity to Orlando, residents enjoy easy access to world-class entertainment, shopping, and dining, while still relishing the tranquility of suburban life.

One of the standout features of Windermere is its family-friendly atmosphere, particularly in neighborhoods that boast playground community features. Imagine waking up to the sound of birds chirping, where children can laugh and play just steps away from your front door. These communities are designed with families in mind, offering safe, well-maintained playgrounds that provide a perfect environment for children to explore, socialize, and grow.

In addition to playgrounds, many homes in Windermere come with spacious yards, perfect for outdoor activities, barbecues, and family gatherings. The community spirit is palpable here, with local events and activities that bring neighbors together, fostering lasting friendships and a sense of belonging.

Whether you’re looking to enjoy peaceful evenings by the lake, explore the local parks, or take advantage of the vibrant community life, Windermere is the perfect place to call home. Experience the charm and warmth of this delightful Florida town, where every day feels like a retreat, and family bonds flourish in a safe and welcoming environment. Come discover your dream home in Windermere today!

Newest Windermere Homes with Playground Community Features

12785 Westside Village Loop, Windermere
$799,000
4 Beds ⋅ 4 Baths ⋅ O6442356 MLS
MOVE-IN READY WINDERMERE HOME WITH CONSERVATION POND AREA! Located in desirable Westside Village, this 4-bedroom, 3.5-bath home offers an open floor plan, tiled roof, landscaped yard, spacious front porch, and a peaceful conservation-view backyard. The bright kitchen overlooks the living room and breakfast nook and features granite countertops, stainless steel appliances, and a large center island with seating and storage. French doors open to the patio, creating an easy connection between indoor and outdoor living. Enjoy resort-style amenities including a community pool, clubhouse, playground, paved walking trails, and beautiful water features. Ideally located near top-rated schools, shopping, restaurants, major highways, and Walt Disney World just minutes away. Experience the best of Windermere living in a highly sought-after community. Schedule your showing today—this move-in-ready home won't last!

12785 Westside Village Loop, Windermere
11963 Vermillion Avenue, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ O6447919 MLS ⋅ Windermere Trails BLDG.
Virtually Staged. LOCATION, LOCATION, LOCATION! Welcome to Windermere Trails, one of Windermere’s most desirable communities. This beautiful 3-bedroom, 2.5-bath townhome offers 1,676 sq. ft. of living space, a 2-car garage, and an unbeatable location just steps from Bay Lake Elementary School. Enjoy the convenience of having shopping, dining, and everyday essentials nearby, including Publix at Lakeside Village, while being just minutes from Walt Disney World and major roadways. The home features an open and functional floor plan, stainless steel appliances, ceramic tile throughout the first floor, and spacious living areas designed for comfortable everyday living. Windermere Trails offers resort-style community amenities including a pool, splash pad, playground, dog park, open-air pavilion, walking areas, and beautiful green spaces. Exceptional Windermere location, convenient access to highly regarded area schools, shopping, dining, entertainment, and everything the Horizon West area has to offer. Schedule your showing today!

11963 Vermillion Avenue, Windermere
8634 Danforth Drive, Windermere
$365,000
2 Beds ⋅ 3 Baths ⋅ O6447780 MLS ⋅ Na BLDG.
Some pictures have been virtually staged. End-Unit Townhome, No Carpet Anywhere This is one the most affordable end-unit townhome in Windermere. As an end unit, it shares a wall on only one side and gets extra windows and natural light all day. The kitchen, dining, and living areas flow together into one bright, open space, and there's no carpet anywhere in the home. All kitchen and laundry appliances stay, so it's ready to move in. The layout has 2 bedrooms and 2.5 baths, and each bedroom has its own bath. The primary suite has a walk-in closet and an ensuite bath with dual vanities. Out back, a private fenced courtyard leads to an oversized rear-entry two-car garage with a pedestrian door. The HOA covers exterior maintenance, roof maintenance, landscaping, and pest control, and it includes the resort-style community pool and clubhouse. You're in the heart of Windermere, minutes from Lakeside Village, Horizon West, Winter Garden Village, and the Disney area, with quick access to major roads. Zoned for A-rated schools: [Elementary School], [Middle School], and [High School]. Easy, low-maintenance living, ready for its next owner. The thoughtfully designed floor plan provides each bedroom with convenient access to a bathroom. The generous primary suite features dual vanities, a walk-in closet, and a spacious ensuite bath designed for comfort and functionality. Step outside to enjoy the private fenced courtyard leading to the oversized rear-entry two-car garage with a pedestrian door, offering both convenience and privacy. Enjoy low-maintenance living with an HOA that covers exterior maintenance, landscaping, roof maintenance, pest control, and access to the beautiful resort-style community pool and clubhouse. Located in the heart of Windermere, this home offers an unbeatable location with top-rated A schools and easy access to Disney, Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, and major roadways. This is a rare opportunity to own one of the finest townhomes to come on the market in quite some time. Don't miss your chance to make this exceptional home yours!

8634 Danforth Drive, Windermere
8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ O6447628 MLS
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere
6858 Merrick Landing Boulevard, Windermere
$615,000
3 Beds ⋅ 2 Baths ⋅ O6447605 MLS
YOUR OWN PRIVATE SPA, A WINDERMERE ADDRESS, AND LANDSCAPING YOU DON’T HAVE TO WORRY ABOUT—6858 Merrick Landing Blvd makes Florida living easy. Located in the desirable community of THE VINEYARDS IN WINDERMERE, FL, this spacious 3-BEDROOM, 2-BATH HOME + BONUS ROOM offers 2,115 SQ FT of thoughtfully designed single-story living with a split floor plan that creates both connection and privacy. Step inside to an open and inviting interior with vaulted ceilings, crown molding, and a kitchen positioned at the heart of the home featuring an OVERSIZED CENTER ISLAND, GRANITE COUNTERTOPS, 42-INCH CABINETRY, STAINLESS STEEL APPLIANCES, and a walk-in pantry overlooking the main living and dining spaces. The BONUS ROOM gives you valuable flexibility without sacrificing a bedroom—perfect for a home office, media room, playroom, fitness space, or second lounge. Privately positioned away from the secondary bedrooms, the OVERSIZED PRIMARY SUITE offers plenty of room for a sitting area, along with a generous walk-in closet and en-suite bath featuring dual vanities and a large walk-in shower with bench. Outside, unwind in your own PRIVATE IN-GROUND SPA, creating a relaxing retreat for quiet mornings or Florida evenings at home. Life in THE VINEYARDS makes ownership even easier, with the HOA including LANDSCAPING/GROUND MAINTENANCE AND PEST CONTROL, plus access to a community pool, parks, playgrounds, sidewalks, and green spaces. The location is another major advantage—currently zoned for INDEPENDENCE ELEMENTARY, BRIDGEWATER MIDDLE, AND WINDERMERE HIGH SCHOOL, with Windermere High located directly nearby, while HORIZON WEST, HAMLIN, WINTER GARDEN VILLAGE, DISNEY SPRINGS, WALT DISNEY WORLD, shopping, dining, and major roadways are all within convenient reach. At 6858 Merrick Landing Blvd, the location is desirable, the floor plan is flexible, and the lifestyle is refreshingly easy. Schedule your private showing today.

6858 Merrick Landing Boulevard, Windermere
7030 Mapperton Drive, Windermere
$649,000
4 Beds ⋅ 3 Baths ⋅ O6447067 MLS
Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your own private pool retreat in this immaculate, move-in-ready home in the desirable Lakes of Windermere community. Featuring four bedrooms, three bathrooms, and 2,455 square feet of thoughtfully arranged living space, this inviting single-story residence features an expansive open floor plan. A roof replaced in 2023, air-conditioning system replaced in 2021, new water heater, and newly replaced pool cage screens add meaningful value to a home that is beautifully prepared for its next chapter. A welcoming covered front porch overlooks the treed community park across the street, creating a peaceful setting for morning coffee or an unhurried evening outdoors. Inside, generous living spaces and an airy, flowing layout provide room to gather, entertain, and settle comfortably into everyday life. The spacious formal living and dining areas offer flexibility for both intimate occasions and larger celebrations, while the heart of the home unfolds into an expansive kitchen and adjoining family room. A preparation island, breakfast bar, abundant cabinetry, generous counter space, dual dining room options and stainless steel appliances make the kitchen as practical as it is inviting. Its open connection to the family room keeps conversation flowing and brings the main living spaces together with views toward the pool. Privately positioned within the floor plan, the spacious primary suite offers a relaxing escape, complemented by two walk-in closets and an en-suite bathroom with separate vanities, a soaking tub, and a separate shower. Three additional bedrooms provide comfortable accommodations and flexibility for guests, a home office, or creative pursuits, while a conveniently located half bathroom serves the main living area. Outdoors, the screened private pool becomes a natural extension of the home, offering space to unwind in the sunshine or enjoy a refreshing swim. The covered lanai provides a shaded setting for outdoor dining and entertaining, with a built-in exhaust hood for your BBQ setup and mature landscaping that enhances the inviting surroundings while providing a completely private pool area. An attached two-car garage accessed from the rear preserves the welcoming character of the front elevation while adding everyday convenience. Beyond the home, Lakes of Windermere offers a large community pool and sun deck, tennis, basketball, and volleyball facilities, three playgrounds, and a fishing pier on Lake Sawyer. Pine Loop Park adds a shaded gathering gazebo and an approximately 0.9-mile sidewalk loop for leisurely walks or an afternoon jog. Ideally located close to A-List schools, all four Walt Disney World theme parks and resorts, with shopping, dining, and daily conveniences nearby, this beautifully maintained residence brings together spacious interiors, inviting outdoor living, valuable updates, and a prime Windermere setting. Call me to schedule your private showing now.

7030 Mapperton Drive, Windermere
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ O6445290 MLS ⋅ 8168 BLDG.
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
1221 Oakdale Street, Windermere
$1,250,000
O6446547 MLS
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!

1221 Oakdale Street, Windermere
5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ O6446272 MLS
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere
8524 Vivaro Isle Way, Windermere
$950,000
4 Beds ⋅ 3 Baths ⋅ G5118124 MLS
Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer's interest rate buy-down. As an additional incentive, the seller is offering a home warranty that can be transferred to the new homeowner, providing added peace of mind. Welcome to 8524 Vivaro Isle Way, a beautifully appointed home in the sought-after Windermere Isle community. Designed for both everyday comfort and entertaining, this home features a private custom pool, upgraded 42" kitchen cabinetry with crown molding, granite countertops, upgraded cabinet hardware, a single-basin undermount sink, and a stylish kitchen backsplash. Upgraded tile flooring extends through the foyer, dining room, family room, office, gallery, kitchen/breakfast area, laundry room, and bathrooms, while the remaining living areas feature carpet. The primary suite offers a raised-height vanity, upgraded undermount sink, semi-frameless shower enclosure, tiled shower, and ceiling-mounted rain shower. Additional upgrades include 8' interior doors, blinds throughout operable windows, a 9' sliding glass door, upgraded bathroom vanities, and upgraded interior finishes. All rooms are upgraded with ceiling fans and light fixtures. Step outside to enjoy your own private pool and create the ideal Florida lifestyle with plenty of space to relax, entertain, and enjoy the sunshine. Located in Windermere Isle, this home offers convenient access to shopping, dining, parks, and recreation, with Winter Garden Village, Lakeside Village, Hamlin, and Walt Disney World-area attractions all within the surrounding area. With its combination of thoughtful upgrades, private outdoor living, buyer incentives, and a convenient location near the Windermere and Winter Garden areas, this home offers an ideal place to enjoy Central Florida living.

8524 Vivaro Isle Way, Windermere
11727 Delwick Drive, Windermere
$875,000
4 Beds ⋅ 3 Baths ⋅ O6445423 MLS
This beautifully maintained 4 Bedroom, 3-Bath Pool home is located in a desirable 24-hour guard-gated Windermere community. Offering a spacious and versatile floor plan, this home features 3 bedrooms on the main level, a dedicated flex/office space, formal living and dining rooms, and an inviting family room ideal for everyday living and entertaining. Upstairs, the private 4th Bedroom provides wonderful flexibility and can easily serve as a guest suite, bonus room, media room, or additional home office. Outside, enjoy the Florida lifestyle from the expansive screened in patio and sparkling salt water pool with a beautiful conservation view! A gas line is already piped to the exterior, providing the opporunity to create a future summer kitchen. Additional highlights include a 3 Car Garage, 2022 Tile Roof, Fresh Exterior Paint, Irrigation System, Security System, and an Orkin Termite Bond for added peace of mind. Ideally located in Windermere with convenient access to major shopping, dining, entertainment, and area amenities, this home combines space, flexibilty, privacy, and a resort-style outdoor living in one exceptional property.

11727 Delwick Drive, Windermere
4906 Aviva Garden Court, Windermere
$3,850,000
4 Beds ⋅ 6 Baths ⋅ O6446042 MLS
Welcome to an exceptional estate built in 2016 by Wyatt, nestled within the prestigious guarded gates of Isleworth. Ideally situated in the intimate Gardens of Isleworth, this beautifully appointed two-story residence offers approximately 6,600 square feet of refined living space, complemented by serene water views, lush landscaping, and a private walking trail. Elegant interiors showcase inlaid wood and travertine flooring, custom ceiling details, a beautiful fireplace, and expansive sliding glass pocket doors that effortlessly connect the interior living spaces to the spectacular outdoor retreat. The chef’s kitchen is designed for both everyday living and sophisticated entertaining, featuring Viking appliances, a striking copper hood, oversized center island, wet bar, butler’s pantry, breakfast nook, and hidden walk-in pantry. The luxurious primary suite offers a private lounge, dual-sided fireplace, cozy sitting area, dual walk-in closets, dressing area, and spa-inspired bath with dual vanities, soaking tub, and an impressive indoor-outdoor shower. Additional highlights include a private theater, balcony, bonus space, elevator, whole-house generator, and a smart-home system. Outdoor living is exceptional, featuring a sparkling pool and spa, fire pit, summer kitchen, outdoor shower, and expansive covered lanai with retractable screens, creating a comfortable year-round setting for relaxing and entertaining while overlooking the tranquil water. An extraordinary six-car garage setup includes four individual single-car garages, with two equipped with vehicle lifts. This exceptional residence seamlessly combines sophisticated design, modern technology, resort-style outdoor living, and privacy within one of Windermere’s most coveted guard-gated communities. Grounds maintenance is included through the HOA. Be sure to explore the virtual tour links for an immersive look at this remarkable Isleworth estate.

4906 Aviva Garden Court, Windermere
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