Windermere Homes with Playground Community Features

Windermere Homes with Playground Community Features

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County, where charm meets modern living. Known for its stunning lakes, lush landscapes, and a tight-knit community, Windermere offers a serene escape from the hustle and bustle of city life while still being conveniently close to Orlando's vibrant attractions.

The heart of Windermere is its enchanting small-town atmosphere, where tree-lined streets and quaint shops invite residents to explore. Enjoy leisurely strolls around the scenic Lake Butler or indulge in a delightful meal at one of the charming local eateries. Windermere is also home to several beautiful parks and recreational areas, making it an ideal location for families and outdoor enthusiasts alike.

For those seeking a family-friendly environment, Windermere’s homes with playground community features are a standout choice. These neighborhoods prioritize family living, offering safe and engaging spaces for children to play and grow. Imagine your little ones laughing and making friends at the playground, while you connect with fellow parents in a welcoming atmosphere. Community events and gatherings foster a sense of belonging, making it easy to forge lifelong friendships.

The real estate options in Windermere are as diverse as its residents, ranging from modern single-family homes to luxurious estates. Each property is designed with comfort and style in mind, ensuring that you find the perfect place to call home. With its blend of natural beauty, community spirit, and family-oriented amenities, Windermere is not just a place to live—it's a place to thrive. Come discover the magic of Windermere today!

Newest Windermere Homes with Playground Community Features

5 Beds ⋅ 7 Baths ⋅ O6439995 MLS

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida’s sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

4243 Isabella Circle, Windermere

5 Beds ⋅ 7 Baths ⋅ O6439814 MLS

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

8142 Tibet Butler Drive, Windermere

5 Beds ⋅ 6 Baths ⋅ O6439156 MLS

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere

4 Beds ⋅ 3 Baths ⋅ S5157040 MLS

WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere

4 Beds ⋅ 6 Baths ⋅ O6439554 MLS

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living.

515 W 2nd Avenue, Windermere

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

4 Beds ⋅ 3 Baths ⋅ O6439354 MLS ⋅ N/A BLDG.

Virtually Staged. Welcome home to Lensdale Lane! This 4-bedroom updated townhome and move-in ready peace of mind: fresh interior paint and trim (2025), new windows and sliding glass door (2022), a newer roof (2021), new exterior paint and siding (2021), and an updated A/C (2019). Step inside to a light and bright open-concept layout where the living, dining, and kitchen flow together effortlessly. The kitchen features sleek quartz countertops, ample storage, and a breakfast bar, perfect for everyday meals or casual entertaining. The main-floor primary suite offers privacy and convenience, while three spacious secondary bedrooms and a second full bath complete the upstairs. Ceramic tile and wood laminate flooring flow throughout; no carpet anywhere! A half bath and laundry round out the main floor. Outside, enjoy your morning coffee on the privacy-fenced courtyard patio, while the covered front porch adds instant curb appeal. The 2-car rear-facing garage keeps the streetscape clean and charming. This home pairs low-maintenance living with an impressive amenity package. The HOA covers exterior maintenance and includes access to a community POOL, clubhouse, FITNESS center, sports courts and walking trails. Zoned for TOP-RATED schools: Windermere High ,Keene's Crossing Elementary, and Bridgewater Middle and just minutes from Winter Garden Vineland Rd, the 429, shopping, dining, and Central Florida's theme parks.Southbridge, part of the sought-after Summerport/Horizon West community, offers an unbeatable sense of community and lifestyle.

13730 Lensdale Lane, Windermere

4 Beds ⋅ 5 Baths ⋅ O6438618 MLS

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ O6439213 MLS

Welcome to your immaculate and charming home in the heart of Downtown Windermere, where timeless traditional style meets modern convenience. Nestled beneath beautiful mature oak trees, this inviting property offers a spacious yard and a welcoming front porch perfect for relaxing in a pair of rocking chairs and enjoying the peaceful surroundings. Step through the front door into a light-filled interior featuring freshly painted walls and warm wood-look tile throughout the first floor. Your remodeled kitchen is both stylish and functional, featuring stainless steel appliances, a gas range, and granite countertops, perfect for everyday living and entertaining. Upstairs, the home showcases its original hardwood floors throughout, adding warmth and character. The spacious primary suite features a beautifully updated bathroom with custom cabinetry, walk in closets, granite countertops, and quality finishes. Two additional bedrooms and a full bathroom complete the second floor, providing plenty of space for family, guests, or a home office. The expansive, fully fenced backyard offers endless possibilities. There is ample room for a pool, playset, fire pit, outdoor games, and entertaining creating a wonderful private space to enjoy Florida’s beautiful weather. Ideally located within walking distance of the Windermere Farmers Market, local shops, restaurants, and more, with beautiful Lake Butler just blocks away, this home offers the best of the Old Windermere lifestyle. Additional highlights include a new roof installed in 2025, water softner, and newer AC unit. Don’t miss the opportunity to make this special home your own. Schedule your private showing today!

706 Oakdale Street, Windermere

3 Beds ⋅ 3 Baths ⋅ O6437694 MLS ⋅ 14077 BLDG.

Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere

3 Beds ⋅ 3 Baths ⋅ O6437967 MLS ⋅ 13048 BLDG.

Beautiful Two-Story Townhome in Windermere Sound!! Welcome to this charming two-story townhome located in the desirable Windermere Sound community. This spacious residence offers 3 bedrooms, 2.5 bathrooms, a 2-car garage, and 1,742 square feet of comfortable living space. All bedrooms are upstairs. The home features a well-appointed kitchen with stainless steel appliances, granite countertops, ample cabinet space, and a convenient layout that opens to the living and dining areas. The thoughtfully designed floor plan provides plenty of space for everyday living, entertaining, and relaxation. Windermere Sound offers a variety of amenities designed for an enjoyable community lifestyle, including a community pool, tennis and basketball courts, playgrounds, and scenic ponds. Lawn care is included, adding to the convenience of living in this well-maintained neighborhood. Ideally located near Disney World, shopping, restaurants, major roadways, and excellent schools, including Windermere High School, this townhome offers the perfect combination of space, convenience, and a desirable Windermere location. A wonderful opportunity to enjoy the comfort and convenience of living in one of the Orlando area’s most sought-after communities.

13048 Garridan Avenue, Windermere

4 Beds ⋅ 3 Baths ⋅ O6401590 MLS

Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond view, providing the ideal atmosphere for everyday living and entertaining guests. Four comfortable bedrooms in tandem with multiple living areas and two covered patios offer ample space for any occasion, while granite countertops, extensive cabinetry, and custom accents throughout add an elegant touch to the interior. Summerport offers residents a list of amenities, including a clubhouse, community pool, sports courts, and multiple trails, parks, playgrounds, and dog parks for endless fun without leaving the neighborhood. Beyond these exceptional amenities, the location provides easy access to daily necessities, medical services, recreation activities, and major highways. The Summerport Village, Winter Garden Village, Shoppes at Lake Butler, and Shoppes at Windward Cay are moments away, placing numerous dining and retail needs right at your fingertips. Nearby Braddock Park and Tibet-Butler Nature Preserve provide natural beauty and outdoor activities close by, while just moments from Disney and Universal, making it ideal for those seeking both tranquil residential living and entertainment accessibility. This combination of a practical design, peaceful pond view, quality amenities, and strategic positioning creates the ideal living experience. Don't let this exceptional opportunity slip away – schedule your private showing today!

13844 Amelia Pond Drive, Windermere

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