Windermere Homes with Golf Community Features

Windermere Homes with Golf Community Features

Welcome to Windermere, Florida, a picturesque gem nestled in Orange County that perfectly blends serene living with vibrant community spirit. Known for its charming small-town atmosphere and stunning natural beauty, Windermere is surrounded by sparkling lakes and lush landscapes, making it a haven for outdoor enthusiasts and families alike.

One of the standout features of this delightful region is its exceptional golf community. Windermere boasts several premier golf courses that cater to both seasoned players and beginners. Imagine waking up to the gentle sounds of nature, stepping out of your beautifully designed home, and finding yourself just a short stroll away from pristine greens and fairways. Whether you’re looking to improve your swing or simply enjoy a leisurely day on the course, the golf community in Windermere offers an unparalleled lifestyle.

The homes in Windermere are as diverse as they are stunning, featuring exquisite architectural designs that reflect the area's charm. From luxurious estates with sprawling yards to cozy family homes nestled in friendly neighborhoods, there’s something for everyone. Many properties come with exclusive access to golf courses, clubhouses, and recreational facilities, allowing residents to indulge in a lifestyle of leisure and elegance.

With its top-rated schools, vibrant local shops, and a welcoming community atmosphere, Windermere is not just a place to live—it's a place to thrive. Experience the perfect blend of relaxation and recreation in this enchanting Florida town, where your dream home awaits in the heart of a flourishing golf community.

Newest Windermere Homes with Golf Community Features

11209 Macaw Court, Windermere
$2,695,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
An extraordinary expression of craftsmanship and architectural distinction, this custom Unnerstall residence was originally conceived as the builder's personal home, where exceptional attention to detail and thoughtful design are evident throughout. Beautifully positioned along the 4th hole of the Golden Bear Club's Jack Nicklaus Signature Golf Course, the estate captures sweeping fairway and tranquil water views within the guard-gated community of Keene's Pointe. Spanning 6,105 square feet of air-conditioned living space, the thoughtfully designed floor plan offers 5 bedrooms, 6 full bathrooms, 1 half bath, and an impressive collection of spaces tailored to today's luxury lifestyle. Soaring ceilings, elegant travertine flooring, exquisite Venetian plaster finishes, and distinctive architectural details create an atmosphere of timeless sophistication, while expansive windows invite natural light and showcase the picturesque surroundings. At the heart of the home, a beautifully appointed gourmet kitchen features rich custom cabinetry, stone countertops, professional-style appliances, and an expansive center island. Opening to a dramatic two-story family room, this inviting space creates a seamless flow for everything from intimate gatherings to grand-scale entertaining. Two dedicated offices, including a richly appointed executive study with custom built-ins and a fireplace, has exceptional flexibility, while a private fitness room and sun-filled bonus/game room provide additional spaces for recreation and relaxation. The expansive main-level primary suite is a sanctuary of comfort and elegance, featuring generous dual walk-in closets and a remarkable spa-inspired bathroom with a soaring two-story ceiling, architectural detailing, dual vanities, and a luxurious soaking tub. A second main-floor bedroom suite offers an ideal retreat for extended-stay guests, while three additional en-suite bedrooms provide beautifully appointed accommodations and privacy throughout the upper level. Beyond the interiors, the home's outdoor living spaces rival those of a private resort. An expansive covered lanai with automated retractable screens transitions effortlessly to a sparkling pool and spa, surrounded by lush, mature landscaping that creates a sense of seclusion while preserving the stunning golf course views. A distinctive copper-roofed gazebo, complete with a summer kitchen and bar, provides an unforgettable setting for alfresco dining, entertaining, and enjoying Florida's beautiful year-round climate. Additional appointments include an expansive paver driveway, a three-car garage with a dedicated golf cart entrance, and an array of custom finishes that reflect the home's exceptional quality and craftsmanship. Set amid the natural beauty of Keene's Pointe, with its winding streets, mature trees, and picturesque golf and water views, this remarkable residence offers an exceptional combination of architectural character, versatile living spaces, and the effortless elegance of the Windermere lifestyle.

11209 Macaw Court, Windermere

8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
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

5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
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

6113 Grosvenor Shore Drive, Windermere
$6,950,000
7 Beds ⋅ 8 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Set behind the guarded gates of Keene's Pointe, lies this masterfully crafted 7-bedroom, 8-bath lakefront estate by Stonebridge Custom Homes presenting an extraordinary opportunity for those seeking uncompromising elegance and everyday indulgence. Expertly designed to invite abundant natural light throughout its over 8700 sqft magnificent interiors while still offering complete privacy and astounding wooded and lake views over its 4+ acre grounds. A stately brick-paver drive, twin motor courts with garage parking for 4 cars and a golf cart, set the tone for the refined lifestyle that awaits within. Through 10-foot solid double doors, the foyer opens to a two-story travertine-tiled formal living area with dramatic stone fireplace and towering windows that frame views of the pool and lake. The kitchen is a culinary masterpiece, featuring a hidden walk-in pantry, Thermador commercial grade appliance suite, including full-size refrigerator and separate freezer, Bosch Dishwasher, Scotsman Ice maker, Busby cabinets, granite countertops, and a double island setup designed for effortless entertaining. A beverage bar connects the kitchen to the formal dining room and iron-gated wine room with 45 bottle Brisa wine refrigerator. The open-concept layout offers casual dining off the kitchen and a family room that flows seamlessly into theatre-style lounge. The first-floor primary suite is a study in calm sophistication, featuring sitting area, poolside terrace access, coffee bar, 2 custom walk-in closets, and a spa-inspired ensuite with dual granite topped vanities, soaking tub, and multi-head steam shower. An executive study, bonus storage, mudroom and laundry, 2 powder rooms, and a private ensuite for visiting guests, complete the first floor. Upstairs, a bonus room for exercise or crafting, an open area for study or reading, add’l laundry, and 5 spacious bedrooms complemented by 4 full baths, ensure every guest enjoys comfort and privacy. From hidden storage and bonus rooms to thoughtfully curated finishes, every detail has been considered with intention and care. Impeccably maintained and thoughtfully updated where it matters, delivering peace of mind as well as prestige (See feature sheet for a full list of updates). Five sets of wall-to-wall sliders open the beautifully appointed interiors to the private outdoor retreat where guests will want to linger. A summer kitchen and outdoor bar overlook the pool with rock waterfall and spa, while an outdoor gas fireplace anchors evenings that stretch long past sunset. The covered lanai areas are enhanced by electronically controlled invisible screens and a mosquito misting system. The beautifully landscaped grounds and fenced backyard extend to a private dock with covered boathouse and electronic lift, providing effortless access to the pristine waters of Lake Tibet and the interconnected Butler Chain of Lakes. Residents of Keene’s Pointe enjoy a country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, pickleball, dining, and a vibrant social calendar. Positioned minutes (3.5 mi.) from historic Windermere with easy access to Orlando's attractions. Furnishings and Regal LS4 Power Boat are negotiable for a truly turnkey move.

6113 Grosvenor Shore Drive, Windermere

9310 Isleworth Gardens Drive, Windermere
$3,595,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere

6120 Greatwater Drive, Windermere
$3,999,000
5 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.

6120 Greatwater Drive, Windermere

5186 Vardon Drive, Windermere
$4,395,000
6 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Primary living spaces include formal living and dining rooms, a kitchen with casual dining, and a home office. The six-bedroom residence offers two bedrooms on the main level, one on the lower level and three on the upper level. The expansive primary suite is includes a large bath finished with oversized floor-to-ceiling stone tile, a freestanding soaking tub, walk-in shower and dual-sink vanity. Designed for year-round enjoyment, the outdoor living experience begins in the enclosed Florida room and unfolds onto a sprawling pool deck overlooking the golf course. A large pool is complemented by an intimate oasis dining area surrounded by a pool moat, a separate sundeck and a covered outdoor grilling area, creating multiple spaces for entertaining, dining and relaxing. With its exceptional arrival, thoughtfully renovated interiors and expansive indoor-outdoor living, this distinctive estate offers a refined setting within one of Isleworth’s most sought-after golf-course locations.

5186 Vardon Drive, Windermere

9343 Tibet Pointe Circle, Windermere
$7,450,000
7 Beds ⋅ 10 Baths ⋅ Keenes Pointe Unit 03 46/104 SubDv. ⋅ 34786 Zip Code
Located directly on Lake Tibet within the guard-gated community of Keene’s Pointe, this extensively updated Stonebridge custom residence blends Mediterranean-inspired architecture with transitional interiors. A long brick-paver driveway leads to a circular motor court, porte cochère, tile roof, stone accents, and arched windows. Oversized glass entry doors frame immediate lake views and open to two-story formal living spaces featuring newly installed wood flooring, detailed ceilings, clerestory windows, and abundant natural light. The kitchen includes an oversized island, quartz countertops, glazed custom cabinetry, double ovens, premium appliances, and a walk-in pantry. Open gathering areas and expansive windows provide continuous views of Lake Tibet. Additional interior features include a game room, dedicated home theater, and a private primary suite with an oversized walk-in closet and updated bathroom. Each secondary bedroom includes an ensuite bathroom. The bathrooms have been updated, the interior has been freshly painted, and the carpeting has been replaced. A detached guest house offers additional flexible living space. Added in 2019, the covered outdoor kitchen and dining pavilion features a wood-paneled ceiling, large dining and preparation island, built-in grill, pizza oven, wine cooler, and oversized refrigerator. The outdoor area also includes a resort-style pool, heated spa, expansive lawn, sand volleyball court, and soccer area overlooking the lake. A private dock with boat lift provides direct access to Lake Tibet and the Butler Chain of Lakes.

9343 Tibet Pointe Circle, Windermere

5192 Vardon Drive, Windermere
$19,500,000
6 Beds ⋅ 10 Baths ⋅ Isleworth Amd 03 SubDv. ⋅ 34786 Zip Code
Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

5192 Vardon Drive, Windermere

8142 Tibet Butler Drive, Windermere
$2,685,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
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

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