Windermere Homes with Sidewalks Community Features

Windermere Homes with Sidewalks Community Features

Welcome to the enchanting town of Windermere, Florida, nestled in the heart of Orange County. Known for its picturesque landscapes and charming atmosphere, Windermere offers a unique blend of small-town warmth and modern conveniences. With its stunning lakes, lush greenery, and vibrant community, this idyllic locale is perfect for families, professionals, and retirees alike.

Windermere is celebrated for its beautiful homes, many of which are situated in communities designed with sidewalks that encourage an active lifestyle and foster neighborly connections. Imagine evening strolls along tree-lined paths, where you can wave to friendly faces and enjoy the serene surroundings. The sidewalks not only enhance the walkability of the neighborhoods but also provide a safe and inviting space for children to play and explore.

The town boasts a variety of amenities, including top-rated schools, boutique shops, and delightful dining options, all just a stone's throw away. Residents can take advantage of the nearby recreational opportunities, including boating and fishing on the stunning Butler Chain of Lakes or enjoying the scenic parks and trails that Windermere has to offer.

Windermere’s commitment to community and quality of life makes it a desirable place to call home. Whether you're seeking a charming single-family residence or a luxurious estate, the homes in Windermere with sidewalks create a welcoming environment where you can truly feel at home. Come discover the charm of Windermere, where every day feels like a retreat in this beautiful lakeside community!

Newest Windermere Homes with Sidewalks 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

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

9100 Palm Tree Drive, Windermere
$579,000
3 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 01 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this inviting 3-bedroom, 2-bathroom pool home, situated on a corner lot with a circular driveway in the established community of Silver Woods. A spacious foyer opens into the living room, flowing seamlessly into the adjoining dining area for easy everyday living and entertaining. The conveniently located kitchen connects to the family room, where wood-look tile and vaulted ceilings create a warm, open gathering space. The split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and attached bathroom. Two additional bedrooms and a full bathroom are located on the opposite side of the home, providing flexibility for guests, a home office, or everyday needs. French doors from the family room open to the patio and in-ground pool, creating a welcoming setting for outdoor dining, weekend gatherings, or simply relaxing in the Florida sunshine. A fenced backyard completes the outdoor space. Recent updates - New Porcelain Tile floor throughout, New Hurricane strength garage door, New cabinetry in garage and laundry room, Custom closets in Primary, Roof 2021, Windows 2020, HVAC 2019. Silver Woods offers low HOA fees and community tennis courts, along with a convenient Windermere location near shopping, dining, and Dr. Phillips’ Restaurant Row. Enjoy access to major roadways and popular Central Florida destinations, including Universal Orlando Resort and Walt Disney World. This home brings together comfortable living, outdoor enjoyment, and everyday convenience!

9100 Palm Tree Drive, Windermere

8205 Stonemason Court, Windermere
$2,650,000
6 Beds ⋅ 6 Baths ⋅ Keenes Pointe Unit 3 SubDv. ⋅ 34786 Zip Code
Distinctive craftsmanship, open-concept interiors and expansive outdoor living distinguish this custom six-bedroom, six-full-bath residence in Keene’s Pointe. Built in 2016 on a nearly ½-acre homesite, the residence unfolds around a spacious great room appointed with custom dining and entertainment cabinetry. The main level encompasses the primary retreat, a guest bedroom with an ensuite bath, a full pool bath, an office, a kitchen, a generous breakfast nook and a walk-in pantry. Upstairs, three bedrooms with ensuite baths accompany a sixth bedroom suited to use as a studio, playroom or flexible living space, along with a spacious loft featuring a hospitality bar. A mini elevator provides a practical way to transport items between floors, simplifying housekeeping. Custom millwork lends continuity throughout the interiors, from integrated bedroom desks and storage drawers to the great-room entertainment center and a full-wall display case in the study/office. Thoughtfully designed dining cabinetry accommodates table linens, dinnerware, silverware and décor, complemented by a substantial custom china cabinet for glassware near the corner wine room. An integrated buffet offers an elegant setting for serving or displaying fresh flowers and collectibles. Solid-wood interior doors and elaborate custom cabinetry in every closet and the oversized walk-in pantry carry this attention to detail throughout the home. Double-pane windows and sliding doors complement a modern, outward-swinging steel double entry door edged in wood. Additional appointments include upgraded Monogram stainless steel kitchen appliances, whole-house water purification and softening, tankless natural gas water heaters, Lutron lighting controls in the main living areas and a dedicated irrigation well. The generous covered outdoor living area extends the entertaining experience with a complete summer kitchen, including a dishwasher, dinnerware storage, a gas grill and a double-burner cooktop integrated into an oversized island. Positioned beside an oversized conversation pit, the island anchors a lounge-like setting for outdoor gatherings. The private backyard brings together a pool, spa and expansive paver deck in an inviting setting for outdoor entertaining. Just steps from the primary retreat, the spa offers a convenient escape, while an illuminated firepit gathering area provides another setting for evenings outdoors. A mini half-court basketball practice area introduces a recreational dimension, balancing spaces for relaxation, gathering and activity. Located in the highly sought after guard gated lakefront and golf course community of Keene’s Pointe and home of the Golden Bear Club, a private golf and tennis club, residents enjoy a host of amenities including a community boat ramp and a range of parks and playgrounds. Come live the Keene’s Pointe lifestyle!

8205 Stonemason Court, Windermere

2925 Butler Bay Drive N, Windermere
$2,200,000
5 Beds ⋅ 5 Baths ⋅ Butler Bay SubDv. ⋅ 34786 Zip Code
Virtually Staged. LUXURY LAKEFRONT ESTATE | 0.64-ACRE LOT | PRIVATE DOCK | PRIVATE POOL | OUTDOOR SUMMER KITCHEN | 3-CAR GARAGE Experience luxury living at its finest in this stunning contemporary lakefront estate, set on an impressive 0.64-acre lot. Featuring two levels of thoughtfully designed living space, this exceptional residence combines elegant architecture, upscale finishes, and breathtaking panoramic lake views. Upon entering through the beautiful solid wood double doors, you are welcomed by an impressive formal living room and a spacious formal dining area. Large panoramic windows frame the spectacular lake views, bringing natural light into the home and creating a seamless connection with the surrounding landscape. A beautifully appointed private office provides the perfect setting for working from home. The gourmet kitchen is truly a chef's dream, featuring high-quality custom cabinetry, quartz countertops, an oversized island, a spacious pantry, and generous workspace. Designed for both everyday living and entertaining, the kitchen flows effortlessly into the inviting family room, complete with custom built-in shelving and a gas fireplace. The luxurious primary suite is a private retreat, featuring elegant wood flooring, separate walk-in closets, and magnificent views of the pool and lake. The spa-inspired primary bathroom offers a large soaking tub and an expansive walk-in shower with dual showerheads. The lower level features three generously sized bedrooms, including one private en-suite bedroom. The remaining two bedrooms share a beautifully designed Jack-and-Jill bathroom, providing comfort and functionality for family members and guests. Additional interior highlights include a fully equipped laundry room with custom cabinetry and a convenient half bathroom with direct access to the pool area. The three-car side-entry garage features built-in storage cabinets, an electric vehicle charging station, and durable epoxy flooring. Step outside and discover your own private paradise! The covered lanai overlooks the beautiful pool and surrounding lake views, creating the perfect setting for relaxation and entertaining. The fully equipped outdoor summer kitchen features a sink, refrigerator, and built-in grill, making outdoor dining and entertaining effortless. Adding to this exceptional property is a private covered dock, offering a unique opportunity to enjoy the waterfront lifestyle. This remarkable lakefront estate brings together space, privacy, luxury, and spectacular views in one extraordinary property. A rare opportunity to own a truly exceptional home where every detail has been thoughtfully designed to elevate everyday living. SCHEDULE YOUR PRIVATE SHOWING TODAY AND EXPERIENCE THIS EXTRAORDINARY LAKEFRONT LIFESTYLE!

2925 Butler Bay Drive N, 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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