Windermere Homes with Gated Community - Guard Community Features

Windermere Homes with Gated Community - Guard Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County, renowned for its tranquil lakes, lush landscapes, and charming small-town atmosphere. Just a stone's throw from the bustling city of Orlando, Windermere offers the perfect blend of serene living and convenient access to urban amenities. With its stunning waterfront views and a vibrant community spirit, it’s no wonder that Windermere has become a sought-after destination for families, retirees, and everyone in between.

One of the standout features of Windermere is its exclusive gated communities, which provide an added layer of security and privacy for residents. These guard-gated neighborhoods are designed to offer a peaceful sanctuary, where you can enjoy the comforts of home in a safe environment. Imagine waking up each day in a beautifully designed home, surrounded by meticulously landscaped gardens and tranquil lakes. Many of these communities boast luxurious amenities, including private clubhouses, swimming pools, and recreational facilities that cater to an active lifestyle.

Living in a gated community in Windermere means more than just security; it fosters a sense of belonging and camaraderie among neighbors. With organized events and activities, residents can easily connect and build lasting friendships. Whether you’re enjoying a leisurely stroll along the scenic pathways or hosting a barbecue in your backyard, the charm of Windermere’s gated communities makes every day feel like a vacation.

Discover the allure of Windermere and explore the exceptional homes available in its prestigious gated communities. Your dream home awaits in this idyllic Florida paradise!

Newest Windermere Homes with Gated Community - Guard Community Features

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

2009 Westover Reserve Boulevard, Windermere
$1,095,000
4 Beds ⋅ 4 Baths ⋅ Westover Reserve Ph 02 SubDv. ⋅ 34786 Zip Code
ELEGANCE, PRIVACY & EXCEPTIONAL OUTDOOR LIVING IN GATED WESTOVER RESERVE. Beautifully maintained custom residence set on approximately half an acre in one of Windermere’s desirable gated communities. From the moment you arrive, the property makes an impression. The expansive front yard is framed by mature landscaping and established greenery, creating a welcoming sense of privacy and a beautiful approach to the home. The generous lot provides a rare feeling of space and separation that is increasingly difficult to find in Windermere. The front and rear grounds are equally impressive, with generous lawn areas, established landscaping and mature vegetation creating a sense of scale, privacy and tranquility. The backyard is an extraordinary private retreat, with expansive green space and peaceful conservation views providing a beautiful natural backdrop. The screened outdoor living area surrounds a private pool, offering an ideal setting for relaxing, entertaining and enjoying the Florida lifestyle with no neighbors in the back. The combination of the oversized yard, conservation setting, mature landscaping and pool area creates an outdoor environment that feels exceptionally private and resort-like. Inside, the approximately 3,678-square-foot residence offers an inviting combination of refined architectural details, thoughtful updates and comfortable Florida living. Soaring ceilings, abundant natural light and thoughtfully designed living spaces create an impressive yet warm atmosphere. The formal living and dining areas provide elegant spaces for entertaining, while the spacious family room, complete with a gas fireplace, serves as a comfortable gathering area. The beautifully redone kitchen blends style, functionality and modern technology, featuring updated cabinetry, stone countertops, a breakfast bar, pantry and brand-new appliances. The adjoining dining area provides an inviting setting for everyday meals and entertaining. The split-bedroom floor plan offers privacy, with the primary suite positioned as a relaxing retreat and additional bedrooms located on the opposite side of the home. The primary suite features high ceilings, a spacious walk-in closet, dual vanities, garden-style tub and separate shower, along with French doors providing direct access to the screened lanai. A dedicated office/den adds flexibility for work, study or additional living space, while the upstairs oversized bonus room provides another versatile area that can adapt to a variety of needs. Additional recent improvements enhance the home’s comfort, functionality and appeal, including a redone laundry room with state-of-the-art washer and dryer, new light fixtures throughout the home, a new water heater, new garage doors and a new irrigation system serving both the front and rear grounds. Additional highlights include a three-car garage, screened lanai, private pool and spa, roof replaced in 2017, and pool improvements including resurfacing and updated equipment. Located within gated Westover Reserve, this residence combines a substantial homesite, beautiful interior spaces, thoughtful modern updates and remarkable outdoor living in a highly desirable Windermere setting. A truly special property where space, privacy, elegance and exceptional Florida outdoor living come together.

2009 Westover Reserve Boulevard, 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

11532 Waterstone Loop Drive, Windermere
$2,199,000
4 Beds ⋅ 6 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere

12721 Jacob Grace Court, Windermere
$1,488,000
4 Beds ⋅ 4 Baths ⋅ Tildens Grove Ph 01 47/65 SubDv. ⋅ 34786 Zip Code
Welcome to 12721 Jacob Grace Court, an exceptional residence nestled within the highly sought-after gated enclave of Tildens Grove in Windermere. Ideally positioned on a quiet cul-de-sac, this remarkable property sits on over a half-acre homesite with serene conservation and pond views, offering a rare combination of privacy, space, and natural beauty. From the moment you enter, you are greeted by an inviting floor plan filled with abundant natural light and elegant finishes throughout. Just past the two-story foyer, executive home office and formal living room, the expansive main living areas are thoughtfully designed to flow seamlessly, creating the perfect setting for both everyday living and sophisticated entertaining. The heart of the home is the beautifully renovated kitchen, featuring generous cabinetry, quality appliances, and ample counter space, all overlooking the main living and dining areas with stunning private views. The primary suite serves as a tranquil retreat, complete with a spa-inspired bath and spacious walk-in closet. Additional second floor bedrooms provide balcony access and flexibility for family, while a first-floor bedroom and bonus room offer an ideal layout for a private guest sanctuary. Step outside and discover one of the home’s most captivating features—a sprawling backyard with a two-story screen enclosure that is anchored by a resort-style pool, spa and expansive entertaining areas set against conservation and water views. Residents of Tildens Grove enjoy a premier lifestyle with gated access, tree-lined streets, tennis courts, playground and proximity to top-rated schools, boutique shopping, dining, golf, and all the attractions that make Windermere one of Central Florida’s most desirable locations.

12721 Jacob Grace Court, 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

6533 Cartmel Lane, Windermere
$1,598,000
4 Beds ⋅ 4 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code
Set on 0.54 acre at the end of a quiet cul-de-sac in the Reserve at Lake Butler Sound, 6533 Cartmel Lane offers single-story living within one of Windermere’s established guard-gated communities. Mature landscaping, a paver driveway and a substantial architectural entry frame the residence, while the private pool opens to an expansive backyard that gives the property a notable sense of space and privacy. Inside, high ceilings and generous natural light shape a thoughtfully arranged split-bedroom floor plan. The primary suite is positioned apart from the secondary bedrooms, creating a more private retreat within the home. Just beyond the bedroom, a bonus room offers a flexible extension of the suite, suited to a sitting room, study or quiet reading space. The principal living areas are distinct yet connected, allowing the home to feel open without sacrificing definition. Generous windows bring natural light throughout, while the formal dining area and multiple gathering spaces create an easy progression from one room to the next. Outdoor living is centered around the screened lanai and pool, both overlooking the broad rear lawn. The scale of the homesite gives the exterior a sense of openness, while the three-car garage provides additional parking and storage. A tile roof completes the home’s architectural profile. Reserve at Lake Butler Sound was conceived as a gated residential community of luxury homes, shaped by consistent architectural and landscape standards intended to preserve a cohesive and harmonious setting. Controlled access established landscaping and a carefully maintained residential environment contribute to a sense of privacy, permanence and distinction. Approximately six minutes away, downtown Windermere offers a refined small-town setting defined by tree-lined streets, local parks, neighborhood dining and the popular Friday farmers' market. Just beyond the community, a public boat ramp provides access to Lake Butler and the interconnected Butler Chain of Lakes, while several of Central Florida’s notable golf courses are within easy reach. Walt Disney World, Universal Orlando, Sand Lake Road, downtown Orlando and Orlando International Airport are approximately 20 to 30 minutes away. With its single-story design, generous homesite and setting within one of Windermere’s established luxury communities, 6533 Cartmel Lane offers a refined expression of Central Florida living, defined by privacy, space and convenient access to the area’s lakes, golf, entertainment and travel connections.

6533 Cartmel Lane, 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

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