Windermere Homes with Pool Community Features

Windermere Homes with Pool Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its enchanting lakes and lush landscapes, Windermere offers a serene escape from the hustle and bustle of city life while providing easy access to the vibrant energy of nearby Orlando. This charming town is renowned for its stunning waterfront views, friendly community atmosphere, and a variety of recreational options, making it a perfect place to call home.

One of the highlights of living in Windermere is the abundance of homes with pool community features. Imagine enjoying sunny Florida days lounging by your private pool, hosting barbecues with friends, or taking a refreshing dip after a long day. Many of these homes are situated in well-planned communities that offer additional amenities such as clubhouses, fitness centers, and beautifully landscaped parks. Families will appreciate the top-rated schools and community events that foster a close-knit, welcoming environment.

Windermere’s neighborhoods are designed with both comfort and luxury in mind, featuring a range of architectural styles from modern masterpieces to traditional designs. Whether you're looking for a cozy single-family home or a sprawling estate, you'll find properties that cater to every lifestyle and budget.

With its stunning natural beauty, vibrant community spirit, and a plethora of amenities, Windermere is more than just a place to live; it's a lifestyle. Come explore the enchanting homes with pool community features that make Windermere the perfect choice for your next chapter. Your dream home awaits!

Newest Windermere Homes with Pool Community Features

$3,500,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere
$610,000
4 Beds ⋅ 5 Baths ⋅ Wickham Park SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained 4-bedroom, 4.5-bath residence situated on a premium 9,055-square-foot corner lot in the highly desirable Wickham Park community of Windermere. Offering 2,192 square feet of thoughtfully designed living space, this two-story home features an open floor plan filled with natural light, spacious living and dining areas, and a private primary suite with a walk-in closet. One of the home's standout features is its expansive backyard, providing exceptional outdoor space rarely found in similar properties. The backyard already includes an above-ground pool, offering the perfect place to relax and enjoy Florida's outdoor lifestyle. There is still plenty of room to create your dream outdoor retreat, whether you envision a summer kitchen, an entertainment area, lush landscaping, or future enhancements tailored to your lifestyle. Perfectly positioned directly across from Horizon West Middle School, this home offers outstanding convenience for families with school-age. The desirable corner-lot location also provides additional street parking along the side of the property, making it easy to accommodate family and guests during gatherings and special occasions. Residents enjoy outstanding community amenities, including a clubhouse, resort-style community pool, and playground, while being just minutes from shopping, dining, major highways, Walt Disney World, and everything that makes Windermere and Horizon West among Central Florida's most sought-after communities. Don't miss this exceptional opportunity to own a beautiful home that combines comfort, functionality, outdoor living, and an unbeatable location in one of Windermere's premier neighborhoods.

12749 Garridan Avenue, Windermere
$425,000
3 Beds ⋅ 3 Baths ⋅ Whickham Park SubDv. ⋅ 34786 Zip Code
This beautiful 3 bedroom, 2.5 bath townhome is in the heart of Windermere. The home features a spacious, open kitchen complete with stainless steel appliances. Step outside to access a private courtyard that connects directly to a two car garage, providing both convenience and privacy. Upstairs you’ll find three comfortable bedrooms and two full bathrooms. With its low maintenance exterior, the HOA takes care of lawn and shrub maintenance, ensuring hassle free living. The Wickham Park community also offers fantastic amenities, including a pool, clubhouse, and scenic walking trails. Just minutes away from Disney, Winter Garden Village, and top rated schools. This home offers an unbeatable location for easy access to everything.

7752 Rigby Street, Windermere
$579,857
3 Beds ⋅ 3 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living.

5577 Lemon Orchard Bend, Windermere
$420,000
3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twnh SubDv. ⋅ 34786 Zip Code
Located in one of Windermere’s most desirable communities, this beautifully updated 3-bedroom, 2.5-bath townhouse offers the perfect blend of style, comfort, and convenience. Just minutes from Disney, Horizon West, premier shopping, dining, and major highways Step inside to discover a bright, open-concept floor plan filled with natural light and designed for both everyday living and effortless entertaining. The modern kitchen features elegant quartz countertops, stainless steel appliances, ample cabinetry, and overlooks the spacious living and dining areas, creating the perfect gathering space for family and friends. One of the home’s standout features is the private fenced courtyard—an inviting outdoor retreat ideal for relaxing, grilling, entertaining, or simply enjoying Florida’s beautiful weather. The detached two-car garage provides added convenience and extra storage. Upstairs, the spacious primary suite offers a walk-in closet and private en-suite bathroom, while two additional bedrooms and a full bath provide flexibility for family, guests, or a home office. Residents enjoy a low HOA along with outstanding community amenities, including a resort-style swimming pool, playground, sidewalks, and scenic surroundings that make this neighborhood one of Windermere’s most sought-after communities. Zoned for highly desirable schools and located in the heart of the thriving Windermere/Horizon West area, this exceptional home combines modern updates, an unbeatable location, and outstanding value. Don’t miss this incredible opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12744 Langstaff Drive, Windermere
$382,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
Welcome to Berkshire Park, a highly sought-after community where timeless style, everyday comfort, and low-maintenance living come together in the heart of Windermere. This impeccably maintained 3-bedroom, 2.5-bath townhome offers 1,644 square feet of beautifully designed living space, combining tasteful finishes with exceptional functionality. The beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area provides the perfect setting for everything from casual breakfasts to holiday gatherings, while a walk-in pantry with ample storage keeps the space organized and functional. French doors lead from the kitchen to a private, fenced patio, creating an inviting outdoor retreat for dining al fresco, entertaining guests, or simply relaxing in the Florida sunshine. Backing to conservation land with picturesque views of mature trees, the backyard offers a peaceful and private setting rarely found in townhome living. Seamlessly connected to the kitchen, the spacious living room offers a warm and welcoming atmosphere, highlighted by an electric fireplace, which is included with the sale of the home. A detached two-car garage completes the property, providing additional storage and everyday convenience. Upstairs, the spacious primary suite serves as a private retreat, complete with a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a full bathroom, offering comfortable accommodations for family, guests, or a dedicated home office. Residents of Berkshire Park enjoy an exceptional lifestyle with amenities designed for both recreation and relaxation, including a community pool, tennis courts, basketball courts, and scenic walking trails winding around tranquil ponds beneath a canopy of mature trees. The HOA further enhances the ease of homeownership by providing landscaping, structural exterior maintenance, and pest control, allowing you to spend more time enjoying everything this beautiful community has to offer. Ideally located just minutes from Walt Disney World, Winter Garden Village, Hamlin Town Center, premier shopping and dining, major roadways, and top-rated schools, this move-in-ready residence offers the perfect balance of location, lifestyle, and convenience. Whether you're searching for your primary residence, a seasonal retreat, or an investment opportunity, 12914 Vennetta Way presents an exceptional opportunity to own a beautifully maintained home in a highly sought-after Windermere community.

12914 Vennetta Way, Windermere
$2,300,000
5 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of the most peaceful cul-de-sacs in the Keene's Pointe community. Perfectly positioned on a stunning water-view homesite with an expansive backyard and exceptional privacy, this home offers an incredibly flexible floor plan rarely found in today's market. The thoughtfully designed layout places the main living areas, private office, and spacious primary suite all on the first floor, creating the perfect setup for everyday living. Upstairs, three generously sized bedrooms and a large bonus room are tucked away, providing an ideal retreat for family or guests. Adding even more versatility, a completely separate detached in-law suite features a spacious bedroom and full bath, making it perfect for extended family, guests, a private home office, or live-in accommodations. Major updates provide peace of mind for years to come, including a brand-new roof, new glass sliders and windows, new septic system and drain field, A/C in 2024, and 2021 water heater. Keene's Pointe is one of Central Florida's premier 24-hour guard-gated communities, set along the pristine Butler Chain of Lakes. Residents enjoy beautifully maintained parks, playgrounds, walking trails, private boat launch access to Lake Burden, fishing piers, and a vibrant community atmosphere. Optional membership to the renowned Golden Bear Club provides access to a Jack Nicklaus Signature golf course, tennis and pickleball courts, a resort-style swimming pool, fitness center, and more. Families will also appreciate the community's proximity to top-rated schools, upscale shopping, fine dining, world-famous attractions, and Orlando International Airport.

9904 Brentford Court, Windermere
$675,000
3 Beds ⋅ 2 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained one-story home in the highly desirable Summerport community of Windermere! Offering 3 bedrooms, 2 bathrooms, and a versatile office/den, this home reflects true pride of ownership and is ready for its next owners. From the moment you arrive, you'll appreciate the excellent curb appeal and inviting exterior. Inside, the spacious open floor plan features elegant tray ceilings, crown molding, luxury vinyl flooring, upgraded ceiling fans throughout, a formal dining room, and a stylish modern kitchen complete with stainless steel appliances, a gas range, a large center island, and an oversized breakfast bar that's perfect for everyday living and entertaining. All appliances, including the washer and dryer, are included for your convenience. The private primary suite offers a beautiful barn door, California Closets, dual vanities, and a relaxing retreat at the end of the day. Throughout the home you'll find plantation shutters, adding both charm and functionality. Step outside to your own backyard oasis featuring a screened lanai overlooking a beautifully landscaped backyard and sparkling pool, only 2.5 years old, with the required safety door locks already in place. The home also includes a water softener, an epoxy-coated garage floor, a gas water heater, and energy-efficient double-pane windows installed in 2026. Additional updates include a new A/C installed in 2024 and the interior and exterior professionally painted in 2025. A two-car garage plus an extended driveway provide plenty of parking. Ideally located just minutes from Winter Garden Village, you'll enjoy easy access to shopping, restaurants, entertainment, major roadways, and the Florida Turnpike. Summerport is known for its outstanding amenities, scenic walking trails, parks, playgrounds, community pool, fitness center, tennis and basketball courts, and picturesque lakes. This exceptional home combines comfort, style, thoughtful upgrades, and an unbeatable location—don't miss the opportunity to make it yours!

13160 Sunkiss Loop, Windermere
$4,495,000
4 Beds ⋅ 7 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code
Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious guard-gated community of Keene’s Pointe in Windermere. Completely reimagined with exceptional attention to detail, this residence seamlessly blends timeless architecture with sophisticated contemporary design. From the moment you enter, soaring ceilings accented by exposed wood beams, expansive porcelain flooring, designer lighting, custom millwork, and walls of glass create an atmosphere of understated elegance and warmth. Designed for both everyday living and grand-scale entertaining, the impressive great room is anchored by a striking floor-to-ceiling porcelain fireplace with custom illuminated built-ins. The gourmet kitchen is beautifully appointed with premium Viking appliances, custom European-style cabinetry, quartz countertops, an oversized center island, and a separate catering kitchen that makes hosting effortless. The luxurious primary suite offers a peaceful private retreat featuring custom-designed walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, a walk-in shower, and exceptional designer finishes throughout. Spacious guest suites provide comfort and privacy for family and visitors alike. One of the home’s most remarkable features is the expansive climate-controlled lanai, thoughtfully designed as a true extension of the interior living space. Complete with a fully equipped summer kitchen, multiple gathering areas, and panoramic golf course views, it offers the perfect setting for year-round indoor-outdoor living and unforgettable entertaining. One of the very few homes on Valhalla Drive to feature a four-car garage, this residence provides exceptional space for automobiles, golf carts, and additional storage. The pool and spa overlook the beautifully manicured fairways, creating a tranquil backdrop that captures the beauty and serenity of one of Central Florida’s premier private golf communities. Located in one of Windermere’s most sought-after addresses, Keene’s Pointe offers 24-hour guarded security, picturesque tree-lined streets, and an exceptional lifestyle centered around the renowned Golden Bear Club. Residents enjoy convenient access to top-rated schools, upscale shopping, fine dining, world-class attractions, and Orlando International Airport. This is more than a luxury home. It is an exceptional opportunity to own a beautifully renovated residence in one of Windermere’s most distinguished private golf communities.

6719 Valhalla Way, Windermere
$599,900
3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 01 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atmosphere, this home combines timeless charm with everyday convenience. Enjoy relaxing on the covered front porch, perfect for morning coffee, visiting with the neighbors or unwinding after a long day. Inside, the thoughtfully designed floor plan offers comfortable living spaces that are ideal for both everyday life and entertaining. The home features a galley style kitchen positioned between a cozy breakfast nook and the dining room, allowing for both casual and traditional dining options. The split-bedrooms provide added privacy. The on-suite primary bathroom features a soaking tub, dual vanities and a separate stand alone shower. The shower glass and tile were replaced in the fall of 2025. The home features real bamboo hardwood flooring in all interior areas except the kitchen, nook, bathrooms and laundry room. From the living room, open the sliders and step into your oversized patio. This patio has a generous covered area and a screened portion, allowing you to comfortably enjoy outdoor living while being protected from the Florida sun, weather and insects. The fully vinyl fenced backyard has two access gates and is ideal for pets, play or outdoor gatherings. New gutters and water heater were added in 2026, offering added peace of mind. Residents of this community enjoy access to a resort-style pool, basketball court, tennis/pickleball courts and a walking path, offering endless opportunities for recreation, relaxation and an active lifestyle. Whether you are searching for your first home, looking to downsize, or simply wanting to enjoy the charm and lifestyle that Windermere is known for, this property offers an exceptional opportunity in a highly sought-after location. Conveniently located near excellent schools, shopping, dining, theme parks and major roadways, this home offers easy access to everything Central Florida has to share. Don’t miss this opportunity - schedule your showing today.

13231 Roxboro Road, Windermere
$799,500
5 Beds ⋅ 5 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code
Welcome to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulously maintained 5-bedroom, 4.5-bathroom residence offers 3,036 square feet of elegant living space designed for comfort, functionality, and entertaining. A long private driveway and charming front courtyard create a grand first impression. Inside, you'll discover spacious living and entertaining areas filled with natural light, soaring ceilings, and an inviting floor plan that flows effortlessly from room to room. Whether hosting holiday gatherings or enjoying quiet evenings at home, every space has been thoughtfully designed for comfortable living. The gourmet kitchen serves as the heart of the home and features abundant cabinetry, generous counter space, and premium appliances. Included with the sale are the kitchen refrigerator, stove/range, built-in wine refrigerator, built-in espresso machine, washer, and dryer, allowing the next owner to move in with ease. One of this home's most distinctive features is its private detached suite, located separately from the main residence with its own private entrance and full bathroom. This versatile space is ideal as an in-law suite, private guest quarters, executive home office, fitness studio, creative workspace, or media room, offering endless possibilities while maintaining privacy from the main living areas. The second story offers generously sized bedrooms and comfortable accommodations for family and guests. The staircase and upstairs bedroom carpeting were replaced approximately 1.5 years ago, while one upstairs bedroom showcases beautiful hardwood flooring, adding warmth and character. Step outside into your own private backyard retreat. The fully fenced backyard provides both privacy and security while creating the perfect setting for outdoor entertaining, pets, or simply relaxing in your own personal oasis. The sparkling swimming pool offers exceptional flexibility, as it can be operated as either a traditional chlorine pool or converted to saltwater, depending on the owner's preference. Recent upgrades include a new pool motor and complete pool filter assembly installed in 2025, and all existing pool equipment is included with the sale. The existing wicker patio furniture also conveys, allowing the next owner to begin enjoying the outdoor living space immediately. The property has been meticulously maintained, with all HVAC units receiving regular service, one HVAC unit replaced, and the tile roof professionally maintained annually, including semiannual soft washing, tile replacement, and recementing as needed to preserve both appearance and longevity. The garage features epoxy flooring, an insulated garage door, its own air-conditioning unit, built-in shelving, and a workbench, while a backyard storage shed provides additional storage. Conveniently located just minutes from top-rated schools, championship golf courses, world-class dining, upscale shopping, Disney, and the Butler Chain of Lakes, this exceptional home offers the perfect blend of luxury, flexibility, and everyday convenience. Whether you're looking for multigenerational living, a private home office, or simply an impeccably maintained luxury residence, this Windermere gem is truly move-in ready.

11434 Rapallo Lane, Windermere
$745,000
5 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 4b SubDv. ⋅ 34786 Zip Code
Investor opportunity in the sought after Windermere Trails community! This tenant-occupied home offers immediate rental income in a high-demand location just minutes from Disney World (Magic Kingdom, Hollywood Studios, Animal Kingdom, Epcot Center and Disney Springs), Winter Garden Historic District, Doctor Philips Restaurant hub, Hamlin Town Center, Horizon West, top-rated schools, shopping, dining, and major highways. Recent updates include new interior and exterior paint, new luxury vinyl plank flooring throughout the second floor, new stair carpet, and a new refrigerator; roof is approximately 9 years old. A turnkey addition to any investment portfolio with excellent long-term appreciation potential. (Updated 2nd floor photos will be added soon to show new flooring)

8931 Lookout Pointe Drive, Windermere
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