Windermere Homes with Community Pool type

Windermere Homes with Community Pool type

Welcome to Windermere, Florida—a charming and picturesque town nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and vibrant community, Windermere offers a serene escape from the hustle and bustle of nearby Orlando, while still providing easy access to its attractions. With its small-town feel and friendly atmosphere, residents enjoy a tight-knit community where neighbors become friends and outdoor adventures abound.

Windermere is famous for its beautiful waterfront properties and scenic views, making it a highly sought-after destination for homebuyers. Among the many appealing features of this delightful town are the homes with community pools, perfect for those who love to relax and socialize under the Florida sun. Imagine stepping out of your backyard and into a beautifully maintained pool area, where you can unwind after a long day or host gatherings with family and friends. These community pools serve as the heart of many neighborhoods, fostering connections and creating lasting memories.

The homes in Windermere are designed with comfort and style in mind, often featuring modern amenities, spacious layouts, and beautiful outdoor spaces. Whether you’re looking for a cozy family home or a luxurious retreat, Windermere has something to offer everyone.

With its beautiful homes, friendly community, and access to recreational activities, Windermere is not just a place to live—it's a place to thrive. Come discover why so many are choosing to call this enchanting town home!

Newest Windermere Homes with Community Pool type

$295,000
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to easy Florida living in the desirable Lakeside community of Windermere! This beautifully maintained 2-bedroom, 2-bathroom condo offers a comfortable open-concept layout with plenty of natural light and a warm, inviting feel throughout. The spacious living and dining areas create an ideal setting for both everyday living and entertaining, while the well-appointed kitchen offers modern appliances, generous counter space, and plenty of room. The primary suite features a private en-suite bath and ample closet space, while the second bedroom offers flexibility for guests, a home office, or additional living needs. Step outside to your private balcony and enjoy your morning coffee or unwind at the end of the day while taking in the peaceful community surroundings. Residents of Lakeside enjoy a variety of amenities designed for an active and relaxed lifestyle, including a community pool, fitness center, and walking trails. Conveniently located near shopping, dining, entertainment, and highly sought-after Windermere-area schools, this home offers the perfect combination of comfort, convenience, and community. Whether you're looking for a low-maintenance primary residence, a place to settle into the Windermere lifestyle, or a smart addition to your real estate portfolio, this condo is ready to welcome you home.

11446 Jasper Kay Terrace Unit 202, 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
$586,542
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. This Cawood floor plan features interior finishes from the AW Collection Coastal, blending clean lines and neutral tones and textures. 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. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

13317 Lush Lime Alley, 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
$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
$489,900
3 Beds ⋅ 2 Baths ⋅ Lakes/Windermere-Peachtree SubDv. ⋅ 34786 Zip Code
Welcome to 13535 Bramham Lane, a spacious and airy 3-bedroom, 2-bath, single-story home offering plenty of room to spread out and make it your own. Freshly painted throughout, the home features tile flooring in the main living areas with carpeting in the bedrooms. The versatile floor plan includes living and dining areas along with a spacious great room, providing multiple spaces for entertaining, relaxing, and everyday living. The kitchen features granite countertops and stainless steel appliances and opens to the great room, creating a comfortable gathering space at the heart of the home. Outside, nicely landscaped grounds create a welcoming first impression, while the charming front porch is perfect for morning coffee or enjoying the Florida weather. A back patio provides additional outdoor living space for grilling, entertaining, or simply relaxing. Complete with a two-car garage, this home offers a wonderful combination of space, comfort, and flexibility. Located within a gated community featuring sidewalks throughout, residents can enjoy a neighborhood setting designed for walking and outdoor living, along with a community pool. It's so close to Disney that you can hear the train whistle!

13535 Bramham Lane, Windermere
$19,500,000
6 Beds ⋅ 10 Baths ⋅ Isleworth Amd 03 SubDv. ⋅ 34786 Zip Code
Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

5192 Vardon Drive, Windermere
$379,900
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
$689,900
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
$500,000
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
$449,000
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
$327,000
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
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