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 stunning lakes, lush landscapes, and a vibrant community spirit. Just a stone’s throw away from the bustling city of Orlando, Windermere offers a serene escape from the fast-paced urban life while still providing easy access to world-class attractions, dining, and shopping.

Windermere is characterized by its charming neighborhoods, many of which are adorned with beautiful homes featuring private pools. Imagine relaxing in your own backyard oasis, soaking up the Florida sun, or hosting unforgettable gatherings with friends and family around the sparkling water. The homes in Windermere are designed with comfort and luxury in mind, often boasting spacious floor plans, modern amenities, and breathtaking views of the surrounding nature.

Community features in Windermere are second to none. Residents enjoy a plethora of recreational activities, from water sports on the pristine lakes to hiking and biking trails that wind through the lush greenery. The town’s commitment to maintaining its natural beauty is evident in the well-kept parks and community spaces, perfect for family outings or quiet afternoons.

Windermere also prides itself on its strong sense of community, with local events and festivals that bring neighbors together, fostering friendships and connections. Whether you’re a first-time homebuyer or looking to upgrade to a luxurious retreat, Windermere’s homes with pool community features offer the ideal blend of peaceful living and vibrant community life. Come discover the charm of Windermere and find your dream home today!

Newest Windermere Homes with Pool Community Features

13578 Gorgona Isle Drive, Windermere
$799,999
5 Beds ⋅ 4 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
It's here~ this rare floor plan that was a former model and beautifully appointed 5-bedroom, 3.5-bath home in sought-after Windermere Isle offers a unique blend of stylish living and useful upgrades with views of the night time fireworks. Designed with an open floor plan and enhanced decorative features, like upscale wall coverings, a coffered ceiling in the dining room (which is currently being used as an at-home office/den) and a custom built-in entertainment feature that adds useful storage, while being visually appealing. The kitchen is finished with granite countertops, tile backsplash, stainless steel double oven, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A large downstairs bedroom equipped with a full bath provides wonderful flexibility for guests or multi-generational living. Upstairs you will find a spacious loft, providing another inviting gathering space. A cute reading nook is positioned just outside the the private primary suite. Inside the primary bedroom you'll find a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a soaking tub, and glass-enclosed shower. The outdoor setting has a large screened lanai with artificial turf for easy maintenance. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways.

13578 Gorgona Isle Drive, Windermere
9061 Legado Drive, Windermere
$389,900
3 Beds ⋅ 3 Baths ⋅ Legado SubDv. ⋅ 34786 Zip Code
Professional Photos Coming Soon! 9061 Legado Drive, Windermere FL. STUNNING FORMER MODEL HOME! Water views and Disney firework views. Completely refreshed, move-in ready townhome with a brand new Calcutta quartz countertop, brand new carpet, and fresh interior paint. The back patio faces the water and the Disney fireworks.

9061 Legado Drive, Windermere
7906 Brofield Avenue, Windermere
$560,000
3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South SubDv. ⋅ 34786 Zip Code
*Video Tour Available* Welcome to Brofield Avenue that’s tucked away in Lake Sawyer South. This quiet loop has no through traffic and this home sits on a conservation lot across from community greenspace. There aren’t any neighbors in the front or back of this property! The front porch with it’s ceiling fan invites you in. You’ll find the formal living and dining space at the front of the home and the open family and kitchen towards the back. The eat-in kitchen has granite countertops, solid wood cabinetry, stainless-steel appliances and a spacious pantry. The large family room has triple slider doors that allow the living space to open to the outdoors. Enjoy the screened patio that overlooks the fenced-in backyard and conservation land. Back inside, you’ll find the primary bedroom with a large walk-in closet, en-suite bathroom with double sinks, garden tub, shower and linen closet. The secondary bedrooms share a hall bathroom with a bathtub and shower. This home is turnkey, used as a vacation home and has been well cared for by the original owners and can be sold furnished. Addition upgrades include a new roof (2025), newer motor in the AC handler (2024), newer light fixtures, and ceiling fans. The HOA includes access to the community pool and playground. Lake Sawyer South is minutes from Disney, restaurants, shopping and great schools.

7906 Brofield Avenue, Windermere
13755 Bravante Alley, Windermere
$460,000
3 Beds ⋅ 3 Baths ⋅ Vineyards/Horizons West Ph 2b SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to Windermere! This beautiful 3-bedroom, 2.5-bath end-unit townhome offers a spacious, thoughtfully designed floor plan with comfortable living spaces both indoors and out. The open-concept great room flows seamlessly into the kitchen, featuring a large island with breakfast bar seating, solid surface countertops, stainless steel appliances, and plenty of room for gathering and entertaining. Upstairs, the primary suite is joined by two additional bedrooms and a spacious loft, offering flexible space for a media room, home office, game room, or second living area. Ceiling fans in the bedrooms add everyday comfort, and the washer and dryer are included. Step outside to the screened-in lanai, complete with a ceiling fan, and enjoy the adjoining paver patio, perfect for relaxing or outdoor entertaining. A *rare fenced and gated side yard provides additional outdoor space, an exceptional feature for townhome living. The 2-car rear-facing garage adds convenience while maintaining the home's attractive streetscape. Shopping, dining, and entertainment are just minutes away at Summerport, Windermere Village, Winter Garden Village, and Horizon West. Plus, enjoy convenient access to Central Florida's world-famous theme parks and attractions. With its end-unit location, versatile floor plan, inviting outdoor spaces, and convenient Windermere setting, this townhome offers a wonderful combination of comfort and convenience!

13755 Bravante Alley, Windermere
6808 Duncaster Street, Windermere
$481,500
3 Beds ⋅ 2 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
"Close by December 31 to take full advantage of Amendment 3 Homestead Exemptions." Welcome to the quiet, tree-lined community of Lakes of Windermere! This amazing home has 2094 heated SF with 3 Bd/2 BA & 2 car garage. As you enter the home the Living room / Dining room is on the right with beautiful Wood Floors. A very open kitchen with center island, 42 inch Cabinetry, Storage Galore including a Large Pantry and a large wraparound bar to the Family Room. The Family room has a gas fireplace and direct access to the covered Porch. The Primary bedroom has a trey ceiling and a large walk in closet. The Primary bathroom has dual vanities, walk in shower & separate garden tub. Interior laundry room with washer & dryer will remain. New roof, New Interior Paint & New Carpet Nov 2026 Located in a wonderful community of Lakes of Windermere, boasting a basketball court, tennis court, volleyball court, two playgrounds, a soccer field, Community pool, fishing and community dock, plus sidewalks perfect for scooters and skateboards. All this comes with a low HOA of just $245/quarter. You’re just minutes from major highways, family services, numerous shopping options and world-class attractions: 15 minutes to Magic Kingdom, 25 minutes to Universal, and 20 minutes to SeaWorld—making this home ideal for both everyday living and enjoying all that Central Florida has to offer.

6808 Duncaster Street, Windermere
14551 Yellow Butterfly Road, Windermere
$784,900
5 Beds ⋅ 4 Baths ⋅ Stillwater Xings Prcl Sc-13 1 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained and thoughtfully updated home, ideally situated along a quiet bend of Yellow Butterfly Road in the desirable Summerport community. Backing to a peaceful natural setting with trees, a scenic walking path, and pond views, this property combines privacy, comfort, and convenience. Step outside and enjoy the fenced backyard, attractive landscaping, young orange and mango trees, and an expansive brick-paver patio—an inviting setting for relaxing, entertaining, or simply enjoying Florida's beautiful weather. Inside, the home features spacious living areas, including a versatile first-floor den that can serve as a home office, study, or flex space. Imagine coming home for the holidays, gathering with loved ones, and enjoying the warm glow of the fireplace at the flick of a switch—a cozy touch that makes this home especially inviting. The attached three-car tandem garage offers generous parking capacity and additional flexibility for storage. Upstairs, five generously sized bedrooms are thoughtfully arranged for comfort and privacy. The expansive primary suite features two walk-in closets, while two additional bedrooms share a Jack-and-Jill bathroom with separate vanities. Another bedroom features its own en-suite bathroom, and the oversized fifth bedroom, overlooking the trees and pond, provides endless possibilities as a playroom, game room, or additional living space. Conveniently located near SR 535, Hamlin's shopping and dining destinations, scenic walking trails, and Summerport's community amenities, this home provides easy access to the area's finest shopping, dining, recreation, and everyday conveniences. Keene's Crossing Elementary School is within easy reach via the walking path behind the home. Bridgewater Middle School, Windermere High School, Windermere Preparatory School, Foundation Academy, and other educational options are also nearby. Lovingly cared for by its owners, this home is being presented for sale due to a family relocation out of state. A wonderful opportunity to make this exceptional Summerport property your own! Seller is open to considering flexible buyer credits toward closing costs or a mortgage rate buydown for purchase proposals at or near the asking price.

14551 Yellow Butterfly Road, Windermere
8133 Enchantment Drive Unit 1307, Windermere
$399,000
4 Beds ⋅ 3 Baths ⋅ Oasis Cove I/Lakeside Village Ph 01 SubDv. ⋅ 34786 Zip Code
Welcome to this BEAUTIFULLY UPDATED 4-Bedroom, 2.5-Bath Condo in the GATED Oasis Cove at Lakeside Village community in Windermere! Offering the spacious layout and FEEL OF A TOWNHOME, this two-story residence combines modern updates including NEWER AC (2023), flexible living spaces and the convenience of LOW-MAINTENANCE condo living. A paver driveway leads to the TWO-CAR GARAGE, featuring an attractive CARRIAGE-STYLE GARAGE DOOR, while the welcoming exterior sets the stage for all that's waiting inside. Step through the front door and you'll immediately appreciate the FRESH, CONTEMPORARY LOOK, highlighted by NEWER WOOD-LOOK LAMINATE FLOORING throughout the main living areas. The SPACIOUS OPEN LAYOUT allows the Kitchen, Dining Area and Living Room to flow together beautifully, creating an inviting space for everyday living or entertaining. The Living Room is filled with NATURAL LIGHT and features sliding glass doors that open to a COVERED REAR PATIO and fenced backyard—a lovely spot to enjoy your morning coffee or relax outdoors with a little green space of your own.The UPDATED KITCHEN is both stylish and functional, featuring STONE COUNTERTOPS, an abundance of cabinetry, STAINLESS STEEL APPLIANCES and a classic subway tile backsplash. A BREAKFAST BAR offers additional seating and creates a natural gathering spot for casual meals or conversation. The spacious FIRST-FLOOR PRIMARY SUITE provides a comfortable retreat, complete with an EN SUITE BATH featuring dual sinks and a step-in shower, and includes a LARGE WALK-IN CLOSET. A CONVENIENT HALF BATH on the first floor is perfect for guests and everyday living.Upstairs, a GENEROUS LOFT adds wonderful flexibility and makes an ideal family room, media space, game room or home office. ARCHITECTURAL ARCHWAYS and distinctive cutouts add character, while NEWER LAMINATE FLOORING and a sleek, modern ceiling fan give the space a fresh contemporary feel. Two additional Bedrooms, each with NEWER CARPETING, provide comfortable accommodations for family or guests, and both offer WALK-IN CLOSETS. A full Bath nearby, serves the upstairs Bedrooms, while an additional FLEX SPACE can be used as a FOURTH BEDROOM, office, hobby room or whatever best suits your needs. Enjoy the ease of LOW-MAINTENANCE LIVING in this GATED COMMUNITY, where amenities include a clubhouse, COMMUNITY POOL and playground, as well as exterior and grounds maintenance, cable, internet, trash and water, giving you more time to enjoy your home and the surrounding area. Oasis Cove is conveniently situated near LAKESIDE VILLAGE CENTER, where you'll find Publix, restaurants and everyday services, and for even more shopping and dining, WINTER GARDEN VILLAGE offers a wide variety of popular retailers and eateries. Outdoor enthusiasts can explore the trails and natural beauty of TIBET-BUTLER PRESERVE, enjoy lakeside recreation at R.D. KEENE PARK or spend an afternoon at WEST BEACH PARK. And with WALT DISNEY WORLD, Disney Springs and the many attractions of Central Florida nearby, there's always something fun to enjoy.The home is also zoned for A-Rated schools—BAY LAKE ELEMENTARY, HORIZON WEST MIDDLE and WINDERMERE HIGH SCHOOL. With its MODERN UPDATES, spacious loft, flexible living spaces and GREAT LOCATION, this Oasis Cove condo offers a WONDERFUL OPPORTUNITY to enjoy the best of Windermere living. Welcome Home!

8133 Enchantment Drive Unit 1307, Windermere
7129 Thicket Branch Alley, Windermere
$450,000
3 Beds ⋅ 3 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code
A kitchen that makes you stop scrolling. A Windermere address that makes you want to stay. This beautifully upgraded 3-bedroom, 2.5-bath townhome in Ashlin Park offers 1,588 square feet of inviting living space, fresh paint, and distinctive contemporary finishes. The centerpiece is the kitchen: brand-new countertops with a dramatic waterfall edge, decorative wood-slat accents, two-tone cabinetry, stainless steel appliances, and sleek architectural lighting. An open layout connects the kitchen, dining, and living areas—perfect for hosting friends or enjoying a quiet evening at home. Wood-look flooring and stylish bathroom finishes carry the contemporary feel beyond the kitchen. Upstairs, the primary bedroom offers a comfortable retreat, with two additional bedrooms providing room for guests or a home office. A welcoming front porch and two-car garage complete the home. Enjoy Ashlin Park’s community pool, playground, and sidewalks, with shopping, dining, and Disney nearby. Schedule your showing and see what makes this home stand out.

7129 Thicket Branch Alley, Windermere
13555 Gorgona Isle Drive, Windermere
$899,000
6 Beds ⋅ 4 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to Windermere Isle, where spacious living, thoughtful design, and an exceptional location come together in this impressive 6-bedroom, 4-bathroom home offering 4,199 square feet of living space, plus a spacious upstairs loft! Designed with both everyday comfort and entertaining in mind, this beautiful two-story residence features an open and versatile floor plan with two bedrooms conveniently located on the first floor. Beautiful wood flooring leads to the second floor, while wood-look tile flooring flows throughout the main living areas, creating a warm and cohesive feel. An abundance of windows fills the home with natural light. The spacious family room opens seamlessly to the beautifully appointed kitchen, featuring quartz countertops, rich dark cabinetry, stainless steel appliances, a gas cooktop, built-in double ovens, a stylish tile backsplash, and an oversized center island with seating, perfect for casual meals and gathering with friends and family. A generous dining area provides additional space for everyday meals, while a separate formal dining room offers an inviting setting for special occasions. Additional highlights include an expansive walk-in pantry and a conveniently located built-in workspace with abundant cabinetry and countertop space. The first floor also offers two bedrooms, providing flexibility for guests, a home office, or multigenerational living. Upstairs, the spacious loft creates an impressive second living area, ideal for a media room, game room, or comfortable gathering space. Four additional bedrooms provide plenty of room for everyone, and quartz countertops in all bathrooms add a cohesive finishing touch. Step outside through the sliding glass doors to a generously sized covered patio overlooking the fenced backyard, offering a wonderful setting for outdoor dining, entertaining, or simply enjoying the Florida weather. As an added bonus, enjoy views of Disney fireworks from your own backyard! Additional features include a two-car garage with overhead storage racks, two air-conditioning systems, and solar panels that will be paid off by the seller at closing, providing an appealing energy-efficient benefit. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

13555 Gorgona Isle Drive, Windermere
11545 Brickyard Pond Lane, Windermere
$2,200,000
8 Beds ⋅ 9 Baths ⋅ Lake Burden South Ph I SubDv. ⋅ 34786 Zip Code
Experience Lakefront Luxury in the Heart of Windermere! Nestled on a peaceful cul-de-sac in the desirable Lake Burden South community, this stunning two-story residence offers an exceptional blend of elegance, privacy, and Florida living. Situated on an expansive 0.75-acre lakefront lot, the home features 8 spacious bedrooms, 8 full bathrooms, 1 half bathroom, and a thoughtfully designed layout filled with natural light and beautiful waterfront views. Step inside to discover soaring ceilings, elegant finishes, and inviting living spaces. The gourmet kitchen features quartz countertops, stainless steel appliances, generous cabinetry, and a spacious center island, perfect for everyday living and entertaining. Two primary suites provide added comfort and flexibility. The true highlight awaits outdoors, where a private pool, fully equipped summer kitchen, and expansive entertaining areas create your own lakefront retreat. Enjoy breathtaking water views and unforgettable Florida sunsets from the upstairs balcony. Additional features include a three-car garage and solar energy system. Residents of Lake Burden South enjoy access to community amenities, including a swimming pool, tennis courts, playgrounds, and scenic walking paths. Ideally located in sought-after Windermere, just minutes from excellent shopping, dining, and Walt Disney World, this remarkable property offers the perfect balance of peaceful lakefront living and everyday convenience.

11545 Brickyard Pond Lane, Windermere
8214 Serenity Spring Drive Unit 2405, Windermere
$350,000
3 Beds ⋅ 3 Baths ⋅ Oasis Cove 2/Lakeside Village Ph X SubDv. ⋅ 34786 Zip Code
Live about as close to the magic as you can get without a Disney address. This home in gated Oasis Cove sits just 3 minutes from Disney property, so park days, dinner reservations, and fireworks nights are a quick drive instead of a trip. The 3 bed, 2.5 bath layout offers 1,512 sq ft and a 1-car garage, with upgraded flooring on the stairs and throughout the upper level. The HOA covers the roof, lawn care, and water, so electricity is your only utility bill, and the HVAC was replaced in 2024. Spend your free time at the resort-style pool and community amenities, or at the parks down the road, instead of maintaining a home. It works equally well for full-time residents and seasonal owners. Zoned for A-rated schools from elementary through high school. Buyer to verify school assignment, HOA coverage.

8214 Serenity Spring Drive Unit 2405, Windermere
5638 Nectarine Drive, Windermere
$1,550,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
Virtually Staged. BEAUTIFUL LAKE CAWOOD VIEWS AND WATER ACCESS SET THE SCENE FOR THIS NEWLY BUILT WINDERMERE HOME! Situated on a PREMIUM LOT in Lake Cawood Cove, this residence welcomes you with a SPACIOUS COVERED FRONT PORCH, thoughtfully selected upgrades, and an elegant, spacious design. This Ashton Woods DUVAL FLOOR PLAN offers approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, with the opportunity to build your own PRIVATE BOAT DOCK. Inside, 10-FOOT FIRST-FLOOR CEILINGS, 9-FOOT SECOND-FLOOR CEILINGS, and 8-FOOT DOORS enhance the spacious feel. LUXURY VINYL PLANK FLOORING extends throughout the living areas, bedrooms, and staircase, while the bathrooms and laundry room feature tile flooring. At the heart of the home, the GOURMET KITCHEN showcases UPGRADED CABINETRY EXTENDING TO THE CEILING, creating a beautifully finished appearance with abundant storage. A SPACIOUS ISLAND with additional cabinetry on the back, an upgraded appliance package, and a customized pantry layout combine style with everyday functionality. The kitchen connects seamlessly to the breakfast area and an impressive GREAT ROOM WITH A SOARING 2-STORY CEILING. Windows welcome natural light and capture views toward the lake, creating an inviting setting for everyday living and entertaining. A separate dining room provides additional space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, offering a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, separate vanities, and a walk-in shower. An additional bedroom suite includes its own full bathroom, while two more bedrooms share another full bathroom. A versatile LOFT offers space for a lounge, study, or recreation area, and the conveniently located upstairs laundry room completes the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and two additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, where beautiful water views and a conservation area toward Lake Cawood create a peaceful, natural backdrop. At the rear of the home, BEAUTIFUL SUNSET VIEWS OVER THE WATER provide a picturesque setting for relaxing evenings and outdoor gatherings. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to personalize your outdoor entertaining space. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and Central Florida’s world-famous theme parks. With its premium setting, distinctive finishes, and generous living spaces, this newly built residence offers an exceptional opportunity to enjoy the Windermere lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5638 Nectarine Drive, Windermere
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