Windermere Homes with Pool Community Features

Windermere Homes with Pool Community Features

Welcome to Windermere, Florida – a picturesque town nestled in the heart of Orange County, where charm meets luxury in a stunning lakeside setting. Known for its serene landscapes and friendly community, Windermere boasts a rich history and a vibrant atmosphere that attracts residents from all walks of life. With its close proximity to the bustling city of Orlando, this quaint town offers the perfect blend of tranquility and convenience.

Windermere is renowned for its beautiful homes, many of which feature inviting pools that create an oasis for relaxation and recreation. Imagine stepping out into your backyard, where the sun glistens on the water, inviting you to unwind in your private retreat. Whether you’re hosting a summer barbecue, enjoying a quiet evening swim, or simply soaking up the Florida sun, a home with a pool in Windermere adds an unparalleled level of enjoyment to your lifestyle.

The community is also characterized by its lush landscapes, scenic parks, and a variety of recreational activities. Residents can explore the nearby Butler Chain of Lakes, perfect for boating, fishing, and kayaking, or take leisurely strolls along the charming streets lined with oak trees. With top-rated schools, boutique shopping, and delicious dining options, Windermere is not just a place to live; it’s a place to thrive.

Discover your dream home in Windermere, where every day feels like a vacation, and the community spirit makes you feel right at home. Embrace the Florida lifestyle and make Windermere your sanctuary today!

Newest Windermere Homes with Pool 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

6858 Merrick Landing Boulevard, Windermere
$615,000
3 Beds ⋅ 2 Baths ⋅ Vineyards/Horizons West Ph 1a SubDv. ⋅ 34786 Zip Code
YOUR OWN PRIVATE SPA, A WINDERMERE ADDRESS, AND LANDSCAPING YOU DON’T HAVE TO WORRY ABOUT—6858 Merrick Landing Blvd makes Florida living easy. Located in the desirable community of THE VINEYARDS IN WINDERMERE, FL, this spacious 3-BEDROOM, 2-BATH HOME + BONUS ROOM offers 2,115 SQ FT of thoughtfully designed single-story living with a split floor plan that creates both connection and privacy. Step inside to an open and inviting interior with vaulted ceilings, crown molding, and a kitchen positioned at the heart of the home featuring an OVERSIZED CENTER ISLAND, GRANITE COUNTERTOPS, 42-INCH CABINETRY, STAINLESS STEEL APPLIANCES, and a walk-in pantry overlooking the main living and dining spaces. The BONUS ROOM gives you valuable flexibility without sacrificing a bedroom—perfect for a home office, media room, playroom, fitness space, or second lounge. Privately positioned away from the secondary bedrooms, the OVERSIZED PRIMARY SUITE offers plenty of room for a sitting area, along with a generous walk-in closet and en-suite bath featuring dual vanities and a large walk-in shower with bench. Outside, unwind in your own PRIVATE IN-GROUND SPA, creating a relaxing retreat for quiet mornings or Florida evenings at home. Life in THE VINEYARDS makes ownership even easier, with the HOA including LANDSCAPING/GROUND MAINTENANCE AND PEST CONTROL, plus access to a community pool, parks, playgrounds, sidewalks, and green spaces. The location is another major advantage—currently zoned for INDEPENDENCE ELEMENTARY, BRIDGEWATER MIDDLE, AND WINDERMERE HIGH SCHOOL, with Windermere High located directly nearby, while HORIZON WEST, HAMLIN, WINTER GARDEN VILLAGE, DISNEY SPRINGS, WALT DISNEY WORLD, shopping, dining, and major roadways are all within convenient reach. At 6858 Merrick Landing Blvd, the location is desirable, the floor plan is flexible, and the lifestyle is refreshingly easy. Schedule your private showing today.

6858 Merrick Landing Boulevard, Windermere

7030 Mapperton Drive, Windermere
$649,000
4 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your own private pool retreat in this immaculate, move-in-ready home in the desirable Lakes of Windermere community. Featuring four bedrooms, three bathrooms, and 2,455 square feet of thoughtfully arranged living space, this inviting single-story residence features an expansive open floor plan. A roof replaced in 2023, air-conditioning system replaced in 2021, new water heater, and newly replaced pool cage screens add meaningful value to a home that is beautifully prepared for its next chapter. A welcoming covered front porch overlooks the treed community park across the street, creating a peaceful setting for morning coffee or an unhurried evening outdoors. Inside, generous living spaces and an airy, flowing layout provide room to gather, entertain, and settle comfortably into everyday life. The spacious formal living and dining areas offer flexibility for both intimate occasions and larger celebrations, while the heart of the home unfolds into an expansive kitchen and adjoining family room. A preparation island, breakfast bar, abundant cabinetry, generous counter space, dual dining room options and stainless steel appliances make the kitchen as practical as it is inviting. Its open connection to the family room keeps conversation flowing and brings the main living spaces together with views toward the pool. Privately positioned within the floor plan, the spacious primary suite offers a relaxing escape, complemented by two walk-in closets and an en-suite bathroom with separate vanities, a soaking tub, and a separate shower. Three additional bedrooms provide comfortable accommodations and flexibility for guests, a home office, or creative pursuits, while a conveniently located half bathroom serves the main living area. Outdoors, the screened private pool becomes a natural extension of the home, offering space to unwind in the sunshine or enjoy a refreshing swim. The covered lanai provides a shaded setting for outdoor dining and entertaining, with a built-in exhaust hood for your BBQ setup and mature landscaping that enhances the inviting surroundings while providing a completely private pool area. An attached two-car garage accessed from the rear preserves the welcoming character of the front elevation while adding everyday convenience. Beyond the home, Lakes of Windermere offers a large community pool and sun deck, tennis, basketball, and volleyball facilities, three playgrounds, and a fishing pier on Lake Sawyer. Pine Loop Park adds a shaded gathering gazebo and an approximately 0.9-mile sidewalk loop for leisurely walks or an afternoon jog. Ideally located close to A-List schools, all four Walt Disney World theme parks and resorts, with shopping, dining, and daily conveniences nearby, this beautifully maintained residence brings together spacious interiors, inviting outdoor living, valuable updates, and a prime Windermere setting. Call me to schedule your private showing now.

7030 Mapperton 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

8524 Vivaro Isle Way, Windermere
$950,000
4 Beds ⋅ 3 Baths ⋅ Windermere Isle-Ph 2 SubDv. ⋅ 34786 Zip Code
Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer's interest rate buy-down. Welcome to 8524 Vivaro Isle Way, a beautifully appointed home in the sought-after Windermere Isle community. Designed for both everyday comfort and entertaining, this home features a private custom pool, upgraded 42" kitchen cabinetry with crown molding, granite countertops, upgraded cabinet hardware, a single-basin undermount sink, and a stylish kitchen backsplash. Upgraded tile flooring extends through the foyer, dining room, family room, office, gallery, kitchen/breakfast area, laundry room, and bathrooms, while the remaining living areas feature carpet. The primary suite offers a raised-height vanity, upgraded undermount sink, semi-frameless shower enclosure, tiled shower, and ceiling-mounted rain shower. Additional upgrades include 8' interior doors, blinds throughout operable windows, a 9' sliding glass door, upgraded bathroom vanities, and upgraded interior finishes. All rooms are upgraded with ceiling fans and light fixtures. Step outside to enjoy your own private pool and create the ideal Florida lifestyle with plenty of space to relax, entertain, and enjoy the sunshine. Located in Windermere Isle, this home offers convenient access to shopping, dining, parks, and recreation, with Winter Garden Village, Lakeside Village, Hamlin, and Walt Disney World-area attractions all within the surrounding area. With its combination of thoughtful upgrades, private outdoor living, and a convenient location near the Windermere and Winter Garden areas, this home offers an ideal place to enjoy Central Florida living.

8524 Vivaro Isle Way, 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

14350 Bridgewater Crossings Boulevard, Windermere
$405,000
4 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code
Come be wow'd by this 4/2.5 bedroom water view townhome that faces Bluebird Pond and garden area from front porch with primary bedroom on main level. Primary bedroom has views of and access to an additional private back porch. Primary bath offers stand alone shower, generous walk in closet and granite counters. Three secondary bedrooms upstairs with views of Bluebird Pond also have access to separate loft space as additional living room, playroom, game room, study, den or library. Any chef would enjoy cooking in this kitchen with views of and access to private back porch, generous granite counter space, large pantry, stainless steel appliances with new microwave and tall cabinets. Half bath downstairs has been remodeled and is just off the living room and kitchen area. Laminate wood floors throughout downstairs and crown molding in the living and dining areas. Entire interior, including ceilings, has been freshly painted. Brand new carpet in upstairs rooms. Roof is 2022, A/C is 2026, Hot water heater is 2026 as well. Two car garage with covered access to home and amble driveway space plus additional guest parking in front of home. From the photos you will see you are walking distance (less than .3 miles) to Foxtail Coffee, Marcos Pizza, Kelly's Ice Cream, the dog park, children's playground, and Keene's Crossing Elementary School. The community offers (also within walking distance) community pool, tennis and pickleball courts, fitness centers, clubhouse, and many miles of walking trails. You simply can't beat this location, zoned A rated schools, and 15 min to Disney theme parks, easy access to major thoroughfares, international airport, fine dining, entertainment, etc.

14350 Bridgewater Crossings Boulevard, Windermere

12809 Holdenbury Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
The best sought-after Windermere location! This beautiful Lakes of Windermere 4 bedroom 2.5 bath home was just updated this summer with NEW ROOF, NEW APPLIANCES, NEW CARPETS, FRESHLY PAINTED INSIDE AND OUT, plus garage and floor fully painted. ELECTRIC VEHICLE CHARGER IN GARAGE. No rear neighbors: Enjoy a calm, quiet pond view from your covered 15x7 back porch. Or meet the neighbors by relaxing on your covered 17x12 front porch facing the tree-lined street! The kitchen/family room combo is light and bright with soaring 2-story ceiling and windows galore! All matching new SS appliances plus lots of wood cabinets and long breakfast bar in the kitchen that adjoins a dinette area with built in desk. All bedrooms are upstairs with new carpets. The extra large Primary suite includes a window seat, and bathroom with garden tub, separate shower, dual sinks, linen closet and private water closet. Three more comfortable bedrooms and bath are down the hall. The Lakes of Windermere community clubhouse and pool are a short walk away in addition to tennis, basketball, volleyball, and soccer courts, three playgrounds, a lake dock with fishing access, and scenic walking trails through the community including GAZEBO AT THE PINE LOOP PARK (Nobelton Drive and Mapperton Drive) a shaded space for community parties and events. Zoned for A+ rated Windermere High School! Short drive to Disney World, and close to 429 for easy access to Orlando and Horizon West for the best shopping and restaurants. Ready for immediate occupancy. Call to see it today!

12809 Holdenbury Lane, Windermere

12934 Vennetta Way, Windermere
$369,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the added privacy of an end-unit location, a peaceful conservation backdrop, and a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. Freshly painted throughout with brand-new carpet, the home feels bright, clean, and move-in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy everyday life. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual-sink vanity, and upgraded frameless-glass walk-in shower. Step outside to your private courtyard—a versatile outdoor space perfect for morning coffee, weekend gatherings, or unwinding at the end of the day. Beyond the courtyard, the rear of the home overlooks a conservation area, creating a peaceful natural setting with no immediate rear neighbors. It’s a rare combination of privacy and convenience. And there’s more to look forward to—a new roof is coming soon, adding another layer of value and peace of mind for the next owner. Ideally located near A-rated schools, parks, shopping, dining, and everyday conveniences, this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

12934 Vennetta Way, Windermere

9010 Reflection Pointe Drive, Windermere
$945,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Located in the desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate four-bedroom 3.5-bath pool home offers an exceptional combination of style, comfort and Central Florida convenience. Unwind beside your own heated saltwater pool and spa while enjoying views of the Disney fireworks. Inside, tile flooring extends throughout the home, creating a clean and cohesive look that is both attractive and easy to maintain. Fresh interior paint in 2026 enhances the bright, welcoming atmosphere. The formal dining room makes a beautiful first impression with its gorgeous coffered ceiling, providing an elegant setting for holiday dinners, celebrations and evenings with friends. The kitchen is designed for anyone who appreciates generous workspace and exceptional storage. A substantial amount of cabinetry is complemented by expansive granite countertops, a tiled backsplash and an oversized walk-in pantry. Pendant lighting highlights the breakfast bar, creating a natural place for casual meals and conversation. Built-in stainless steel appliances and a Bosch Dacor refrigerator installed in 2022 complete this impressive space. A drinking water filtration system and a whole-house water softener add everyday convenience. The kitchen opens naturally to the spacious family room, where a stacked stone accent wall adds warmth, texture and architectural interest. Views of the pool create a beautiful backdrop and keep the indoor living areas connected to the outdoor setting. Whether hosting a crowd or enjoying a quiet evening at home, the open arrangement allows everyone to remain part of the conversation. Go outside to the heated saltwater pool and spa. With the propane heater, the pool can be enjoyed well beyond the traditional swimming season, while the space offers plenty of room for lounging, dining and entertaining. The pool filtration equipment was replaced in 2024. The thoughtfully planned four-bedroom, 3.5-bath layout provides flexibility for a family, guests or a home office. The washer and dryer (2022) are also included. A complete Bosch HVAC system, including interior and exterior equipment, was installed in spring 2024 and carries a 10-year parts/labor warranty w/required annual maintenance. The water heater is from 2019, and the exterior and tile roof were professionally power washed in 2024. An interior ADT security system and exterior CCTV camera system provide additional peace of mind. A separate two-car (with epoxy floor in 2023 and one-car garage epoxy in 2026) provides three total spaces for vehicles, storage or hobbies. Just inside one of the garages, a drop station features areas for phone charging, along with space for packages, bags and daily essentials. Windermere Trails offers a resort-style community pool, walking trails, playgrounds, pavilions, a dog park and fitness areas. Surrounded by the natural beauty of the Butler Chain of Lakes, the community is close to highly regarded A-rated schools, Lakeside Village, Hamlin Town Center, Winter Garden Village, Horizon West and the renowned dining of Dr. Phillips. Nearby SR 429 provides convenient connections to the Turnpike, SR 408 and I-4, while Walt Disney World, Disney Springs, shopping, golf, boating, restaurants and medical services are all nearby. Beautifully maintained and ready now, this home combines inviting interior spaces, a private pool retreat, recent improvements and a location that places the best of Central Florida at your doorstep.

9010 Reflection Pointe Drive, Windermere

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