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. Known for its stunning lakes, lush landscapes, and charming neighborhoods, Windermere offers a serene escape from the hustle and bustle of nearby Orlando while still providing easy access to its vibrant attractions. With a rich history dating back to the late 1800s, this quaint town is adorned with beautiful tree-lined streets, boutique shops, and delightful dining options, making it a perfect place to call home.

One of Windermere's most appealing features is its array of homes with pool community amenities. Imagine stepping out into your backyard oasis, where you can bask in the Florida sunshine, host lively pool parties, or simply unwind with a good book by the water. Many of the homes here are designed with outdoor living in mind, offering spacious lanai areas, summer kitchens, and beautifully landscaped surroundings that enhance the overall ambiance.

The community spirit in Windermere is palpable, with friendly neighbors and a variety of local events that foster a sense of belonging. Residents enjoy access to top-rated schools, recreational parks, and scenic walking trails, all while being just a stone's throw away from the enchanting beauty of the Butler Chain of Lakes. Whether you’re seeking a family-friendly atmosphere or a tranquil retreat, Windermere’s homes with pool community features provide the perfect backdrop for creating lasting memories. Discover your dream home in this idyllic town, where relaxation and community come together in perfect harmony.

Newest Windermere Homes with Pool Community Features

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

4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code

Located in desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate 4 bedroom 3 1/2 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 w/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. Step 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 4 bedroom 3 1/2 bath layout provides flexibility for 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 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 2 car (with epoxy floor in 2023 and 1 car garage epoxy 2026) provide 3 total spaces for vehicles, storage or hobbies. Just inside one of the garages, a convenient 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 brings together inviting interior spaces, a private pool retreat, valuable recent improvements and a location that places the best of Central Florida at your doorstep.

9010 Reflection Pointe Drive, Windermere

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

3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Lake Reams Twnh SubDv. ⋅ 34786 Zip Code

LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic of Walt Disney World and located in a highly rated school zone! This beautiful 3-bedroom, 2.5-bath townhouse offers the perfect combination of location, comfort, and lifestyle, featuring a spacious and functional layout plus a private fenced backyard, ideal for relaxing, entertaining, and enjoying the Florida lifestyle. Experience a beautiful community surrounded by nature and exceptional amenities, including a community pool, playground, walking trails, scenic lakes, and lush green spaces. Conveniently located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions. Whether you’re looking for your next home or an investment opportunity in one of the Orlando area’s most sought-after locations, this is an opportunity you don’t want to miss!. LIVE IT. INVEST IN IT. LOVE WINDERMERE !!!

8608 Brookvale Drive, Windermere

5 Beds ⋅ 3 Baths ⋅ Vineyards Of Horizons West Phase 1b SubDv. ⋅ 34786 Zip Code

The best family living location! Welcome home to this fabulous 5 bedrooms, 3 full baths, 2 car garage located in the peaceful community of Vineyards in Windermere Florida. Gorgeous subdivision convenient to major roadways, A+ Rated Schools, Shopping, entertainment and so much more. Just minutes away from Walt Disney World. Spacious Master ensuite with walk-in closet. Modern Kitchen with stainless steel appliances with a gas range, granite counter tops and dark wood cabinets! Screened patio with beautiful spacious view of the large yard and conservation. Community comes with a Park/playground and community pool. Do not miss this awesome opportunity!!!

6614 Bridgewater Village Rd, Windermere

4 Beds ⋅ 2 Baths ⋅ Lakes/Windermere-Peachtree SubDv. ⋅ 34786 Zip Code

Virtually Staged. Space, flexibility, and a fantastic Windermere location! Set on a prime CUL-DE-SAC LOT in the GATED Lakes of Windermere-Peachtree community, this spacious 3-bedroom + BONUS, 2-bath, 2-car garage home offers a versatile floor plan with the convenience of MAIN-LEVEL LIVING plus an oversized BONUS ROOM upstairs. A NEWER A/C (2022) adds to the appeal. Inside, you will find a welcoming foyer that opens to combined formal living and dining spaces before making your way into the kitchen that connects seamlessly with a casual dining area and spacious family room, creating an easy layout for everyday living and entertaining. Sliding glass doors extend the living space outdoors to a COVERED LANAI. Privately positioned at the back of the home, your PRIMARY SUITE features a WALK-IN CLOSET and private EN-SUITE BATH. Bedrooms two and three share a second full bath, keeping the primary living spaces, bedrooms and baths conveniently together on one level. Upstairs, the bonus room delivers valuable flexibility and can easily serve as a MEDIA ROOM, second living area, HOME OFFICE, guest space or 4TH BEDROOM. Lakes of Windermere-Peachtree offers a beautiful natural setting surrounded by trees and conservation, along with a COMMUNITY POOL and PLAYGROUND. The home is ZONED FOR “A” RATED SCHOOLS, including WINDERMERE HIGH SCHOOL, and is ideally located just off Reams Road with easy access to SR-429. Walt Disney World, Orange County National Golf Center, Four Seasons Golf & Sports Club, ESPN Wide World of Sports, shopping, dining and everyday conveniences are all just minutes away. LOCATION, LAYOUT & VERSATILITY – this Windermere home delivers all three. Call today to schedule a tour and let us say WELCOME HOME!

13424 Hopkinton Court, Windermere

3 Beds ⋅ 3 Baths ⋅ Carrington SubDv. ⋅ 34786 Zip Code

Welcome to 12333 Via Derna Pl, a beautifully updated townhome located in the highly desirable Carrington community of Windermere. Offering 1,919 sq. ft. of living space, this spacious 3-bedroom, 2.5-bath home features a bright open-concept floor plan designed for both comfortable everyday living and entertaining. Recent updates to the family room, kitchen, and shared bathroom give the home a fresh, modern feel, while abundant natural light creates a warm and inviting atmosphere throughout. The property is also EV-ready, with infrastructure already in place for an electric vehicle charger. Ideally located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions, this move-in-ready home offers an excellent combination of location, space, and modern convenience. The Tesla charger and window curtains are not included in the listing price but may be negotiated separately. Schedule your private showing and discover everything this Windermere home has to offer!

12333 Via Derna Place, Windermere

3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Windermere community. Offering a perfect blend of comfort, style, and convenience, this move-in-ready home is an exceptional opportunity in one of Central Florida’s most sought-after areas. Step inside to discover a thoughtfully designed interior featuring no carpet throughout, making everyday living and maintenance a breeze. The well-appointed kitchen showcases stainless steel appliances, stone countertops, a stylish backsplash, and abundant cabinet space. Ceiling fans throughout the home, including on the private balcony, add an extra level of comfort and convenience. A washer and dryer are also included. Residents of Lakeside at Lakes of Windermere enjoy an array of resort-style amenities, including a sparkling community pool, spacious fitness center, and beautifully maintained grounds—creating a welcoming environment to relax, entertain, and enjoy the Florida lifestyle. The location is truly hard to beat! Lakeside Village Center is directly across the street, putting everyday conveniences just steps from your front door. Just minutes from Walt Disney World, major highways, highly regarded schools, shopping, dining, and the charming community of Windermere, this condo offers an incredible combination of lifestyle and location. Whether you're searching for a primary residence, vacation home, or investment property, this exceptional condo checks all the boxes. Come see why this Lakeside at Lakes of Windermere gem deserves to be at the top of your list!

8156 Boat Hook Loop Unit 623, Windermere

4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code

WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere

2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twhm SubDv. ⋅ 34786 Zip Code

Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out front and a tranquil conservation area in the back. The affordable HOA provides added peace of mind by covering exterior and roof maintenance, landscaping, and access to the sparkling community pool. This 2-bedroom, 2.5-bath townhome with a 2-car garage offers a flexible floor plan filled with inviting living spaces. A tiled entry foyer welcomes you into the first floor. Crown molding throughout adds an elegant finishing touch to the home’s inviting interior. The open kitchen features granite countertops, white subway tile backsplash, an undermount sink with a beautiful view, 42" wood-grain cabinetry, closet pantry and stainless steel appliances. The adjoining breakfast nook provides plenty of space for casual dining. Just off the kitchen is a separate dining room with beautiful wood flooring that could easily serve as a home office, den or flex space. The wood flooring continues into the bright and comfortable living room overlooking the private courtyard. Step outside to your fenced courtyard, complete with grass, pavers and a concrete patio area ready to accommodate your outdoor living needs. The courtyard also provides convenient access to the detached 2-car garage. Upstairs the beautiful wood flooring continues. The spacious primary suite is a true retreat. A modern barn door opens to the ensuite bath featuring dual undermount sinks, a walk-in closet, linen closet and an oversized soaking tub and shower combination. The second bedroom also offers a walk-in closet and its own private ensuite bathroom—ideal for guests, family or a roommate arrangement. An upstairs laundry area adds everyday convenience. Enjoy easy access out front to the bike/walking path that leads just over 1 mile to Lakeside Village Center, home to Publix, Starbucks, cafés, banks, recreation areas, and other everyday conveniences. The Lakes of Windermere is highly sought after for its desirable location, convenient access to high rated schools, shopping, dining, and all of the Walt Disney World parks. And with the Magic Kingdom nearby, you can even enjoy the magic of nightly fireworks right from your front door. With its flexible floor plan, private outdoor space, conservation setting, 2-car garage, and exceptional location, this townhome has so much to offer. Now is your opportunity to own a beautiful home in one of Windermere’s most convenient communities!

12417 Cruxbury Drive, Windermere

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Windermere Sound Ph 2 SubDv. ⋅ 34786 Zip Code

Beautiful Two-Story Townhome in Windermere Sound!! Welcome to this charming two-story townhome located in the desirable Windermere Sound community. This spacious residence offers 3 bedrooms, 2.5 bathrooms, a 2-car garage, and 1,742 square feet of comfortable living space. All bedrooms are upstairs. The home features a well-appointed kitchen with stainless steel appliances, granite countertops, ample cabinet space, and a convenient layout that opens to the living and dining areas. The thoughtfully designed floor plan provides plenty of space for everyday living, entertaining, and relaxation. Windermere Sound offers a variety of amenities designed for an enjoyable community lifestyle, including a community pool, tennis and basketball courts, playgrounds, and scenic ponds. Lawn care is included, adding to the convenience of living in this well-maintained neighborhood. Ideally located near Disney World, shopping, restaurants, major roadways, and excellent schools, including Windermere High School, this townhome offers the perfect combination of space, convenience, and a desirable Windermere location. A wonderful opportunity to enjoy the comfort and convenience of living in one of the Orlando area’s most sought-after communities.

13048 Garridan Avenue, Windermere

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