Windermere Homes with Gated Amenities

Windermere Homes with Gated Amenities

Located in Orange County, Florida, the charming town of Windermere offers residents a peaceful and luxurious lifestyle. With its pristine lakes, lush landscapes, and close proximity to Orlando, Windermere is a highly sought-after region for real estate.

One of the key features that make Windermere so appealing is its homes with gated amenities. True to its reputation as an exclusive community, many properties in Windermere come with gated entrances, providing residents with an added sense of security and privacy. These gated amenities not only enhance the overall appeal of the homes but also contribute to the overall value of the properties.

Living in a home with gated amenities in Windermere means residents can enjoy a tranquil and safe environment. The gated entrances restrict access to only authorized individuals, ensuring that homeowners can relax and enjoy their surroundings without unnecessary disturbances. Whether it's taking a leisurely stroll around the neighborhood or letting the kids play outside, residents can have peace of mind knowing that their community is secure.

In addition to the gated entrances, homes with gated amenities in Windermere often offer additional perks such as community pools, fitness centers, clubhouses, and beautifully landscaped common areas. These amenities provide residents with opportunities for socializing, recreation, and relaxation, making it a truly desirable place to live.

If you're looking for a home that offers both security and luxury, Windermere's homes with gated amenities are an excellent choice. With its picturesque surroundings and convenient location, this region truly offers the best of both worlds for those seeking a refined lifestyle in Florida.

Newest Windermere Homes with Gated Amenities

8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
5944 Caymus Loop, Windermere
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an oversized paved patio and custom pergola seating. Privacy is included with the 6 ft vinyl fence. New Roof ('20), AC units(’18/’19), Hot Water Heater (’21/Natural Gas), Exterior Paint(’20) Shallow well for irrigation, termite bond, 5 Camera Ring System (8/21) including Flood lights and doorbell, expanded paver driveway (2025) for additional parking, blinds and plantation shutters, central vacuum system, and new septic pump('22) are just a few of the great features of this home. Located close to dining, shopping, expressways, tourist attractions, and top-rated public and private schools, this home and community has it all!

5944 Caymus Loop, Windermere
7231 Sangalla Drive, Windermere
$1,348,000
5 Beds ⋅ 5 Baths ⋅ Casa Del Lago-Replat SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of interior space with a private pool and a location remarkably connected to the destinations that define Southwest Orlando. Recently refreshed, the residence features newly painted interiors and new light white oak luxury vinyl flooring throughout the home, excluding the bathrooms. The result is a lighter, more contemporary palette that carries naturally from room to room and gives the home an entirely new point of view. At the center of the main level, the kitchen combines granite countertops, an oversized island, stainless steel appliances, gas cooking and generous cabinetry and pantry storage. It opens to the living and breakfast areas, creating one continuous space for daily living and entertaining. A formal dining room and dedicated office add definition to the floor plan without interrupting its openness. The first-floor primary suite offers a spacious retreat with a walk-in closet, dual vanities and oversized walk-in shower. Additional bedrooms provide flexibility for guests, work or creative space, while the approximately 448-square-foot upstairs bonus room adds another layer of versatility for a media lounge, game room, fitness space or secondary living area. Outside, the architecture gives way to a distinctly Florida setting. A screened swimming pool, covered lanai and expansive paver deck extend the living space outdoors, complemented by low-maintenance turf and additional backyard space. A three-car garage completes the residence. Casa Del Lago is positioned within Windermere’s Lake Burden area, placing the home near Lakeside Village, Hamlin, Downtown Windermere, Golden Oak, Four Seasons Resort Orlando, Walt Disney World Resort and the Sand Lake Road dining district known as Restaurant Row. The location offers convenient access to shopping, dining, entertainment and major roadways while maintaining the privacy of a gated residential setting. A refreshed interior, private outdoor living and a Windermere address positioned at the center of it all.

7231 Sangalla Drive, Windermere
6544 Cartmel Lane, Windermere
$2,390,000
5 Beds ⋅ 5 Baths ⋅ Reserve At Lake Butler Sound Unit 2 SubDv. ⋅ 34786 Zip Code
Welcome to Villa Cartmel, where privacy lives beautifully. Set behind the gates of Lake Butler Sound, this exceptional Windermere residence offers a rare combination of privacy, tranquility, and effortless Florida living. With 4.185 sqf (check remarks), 5 bedrooms, 4.5 bathrooms, and a 3-car garage, the home has been thoughtfully designed for everyday comfort, elegant entertaining, and the relaxed lifestyle that makes Central Florida so desirable. From the moment you enter, beautifully appointed living spaces flow naturally from one to the next, creating an atmosphere that feels luxury yet welcoming. Expansive windows bring abundant natural light into the interiors while framing the lush greenery beyond and creating a seamless visual connection with the outdoors. At the heart of the home, the beautifully designed kitchen combines style and functionality with Viking appliances, generous workspace, ample cabinetry, and an inviting layout that connects effortlessly with the surrounding living and entertaining areas. Whether hosting an intimate dinner or gathering with family and friends, the home is designed to bring everyone together. The primary suite is a retreat of its own, offering a peaceful escape from the main living areas. Its spa-inspired bath creates a serene environment for relaxation, transforming everyday routines into a more indulgent experience and giving the suite the feeling of a private sanctuary within the home. Step outside and Villa Cartmel reveals one of its most compelling features. Surrounded by lush landscaping and protected conservation views, the backyard offers exceptional privacy and a beautiful natural backdrop. The pool becomes the centerpiece of a true outdoor living experience, complemented by generous areas for lounging, dining, and entertaining. Enjoy the luxury of your own private 3-hole golf course, where leisure, elegance, and the beauty of outdoor living come together at Villa Cartmel. A screened outdoor kitchen extends the living space beyond the interiors and makes year-round Florida entertaining effortless. Enjoy quiet mornings overlooking the greenery, relaxed afternoons by the pool, al fresco dinners, or evenings spent with family and friends. With its mature landscaping and conservation setting, the outdoor space feels less like a traditional backyard and more like a private resort at home. Additional bedrooms and living spaces provide flexibility for family and guests while preserving the sense of comfort and privacy found throughout the residence. Located within the private gates of Lake Butler Sound, Villa Cartmel offers a remarkable balance of seclusion and connection—the tranquility of its natural surroundings paired with the convenience and lifestyle of one of Windermere’s most desirable communities. Elegant without being formal and private without feeling secluded, this is a home created for entertaining, unwinding, and enjoying life both indoors and out. Villa Cartmel transcends the ordinary definition of luxury living and design. A distinguished private estate where timeless elegance, refined sophistication, and an extraordinary lifestyle converge.

6544 Cartmel Lane, 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
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
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
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
11727 Delwick Drive, Windermere
$860,000
4 Beds ⋅ 3 Baths ⋅ Reserve/Belmere Ph 04 SubDv. ⋅ 34786 Zip Code
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
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
6126 Payne Stewart Drive, Windermere
$3,250,000
3 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inviting for outdoor dining and relaxing in the Florida Sunshine.

6126 Payne Stewart 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
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