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. Renowned for its serene lakes and lush landscapes, Windermere offers a perfect blend of small-town charm and modern amenities. With its close-knit community feel and stunning natural surroundings, it’s no wonder that Windermere is a sought-after location for families and individuals alike.

One of the standout features of Windermere is its vibrant residential neighborhoods, many of which boast exquisite homes with private pools. Imagine stepping out into your own backyard oasis, where you can unwind under the Florida sun or host lively gatherings with friends and family. These pool homes not only provide a refreshing escape during the warm summer months but also enhance the overall lifestyle of residents, offering a perfect spot for relaxation and recreation.

The community features in Windermere are equally impressive. With top-rated schools, charming parks, and an array of shopping and dining options, residents enjoy a high quality of life. The town is also conveniently located near major roadways, making it easy to access nearby attractions like Walt Disney World and the vibrant city of Orlando.

Whether you’re looking for a luxurious estate or a cozy family home, Windermere’s real estate market has something for everyone. Embrace the Florida lifestyle in a community that truly feels like home. Discover your dream home with a pool in Windermere, where every day can feel like a vacation!

Newest Windermere Homes with Pool Community Features

$295,000
2 Beds ⋅ 2 Baths ⋅ O6442239 MLS ⋅ 14466 BLDG.
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 ⋅ O6444644 MLS ⋅ 14350 BLDG.
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
$625,000
4 Beds ⋅ 3 Baths ⋅ S5157920 MLS
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
$586,542
3 Beds ⋅ 3 Baths ⋅ TB8551016 MLS ⋅ 3 BLDG.
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 ⋅ O6348704 MLS ⋅ Venetta Way BLDG.
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 ⋅ G5117935 MLS
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 ⋅ S5157827 MLS
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 ⋅ O6441344 MLS
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 ⋅ S5157627 MLS ⋅ 8 BLDG.
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 ⋅ S5157579 MLS
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 ⋅ O6438808 MLS
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 ⋅ O6441184 MLS
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
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