Windermere Homes with Sidewalks Community Features

Windermere Homes with Sidewalks Community Features

Welcome to Windermere, a charming town located in Orange County, Florida. Known for its picturesque landscapes and serene atmosphere, Windermere offers a perfect blend of small-town charm and modern amenities.

One of the standout features of Windermere is its Homes with Sidewalks Community. True to its name, this community is designed to promote a healthy and active lifestyle, with well-maintained sidewalks perfect for walking, jogging, or biking. Residents can enjoy leisurely strolls or connect with neighbors while taking in the beauty of the surroundings.

Living in Windermere means enjoying a close-knit community where neighbors become friends, and every street tells a story. With top-rated schools, beautiful parks, and a thriving local economy, Windermere offers an exceptional quality of life for residents of all ages.

Whether you're looking for a cozy cottage, a spacious family home, or a luxurious estate, Windermere has a diverse range of real estate options to suit every taste and budget. From historic properties with character to modern homes with all the latest amenities, Windermere has something for everyone.

Come and discover the magic of Windermere, where small-town charm meets modern living. Find your dream home in this vibrant community and experience the best that Florida has to offer.

Newest Windermere Homes with Sidewalks Community Features

$1,100,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Discover luxury living in the heart of Keene's Pointe, Windermere. Home to the renowned Golden Bear Golf Club. This meticulously designed 4-bedroom, 3-bathroom , 3-car garage residence offers over 3,000 square feet of open living space, perfect for both relaxed living and grand entertaining. The moment you step inside, you’ll be welcomed by elegant formal spaces, including a dining room, formal living areas and versatile additions that can be used as a flex spaces for additional seating, home office, playrooms and much more. The heart of the home is a beautifully appointed open gourmet kitchen, complete with granite countertops, stainless steel appliances, a natural gas range, a large center island, and a breakfast bar. A built-in desk provides the perfect nook for planning meals or organizing your day. Adjacent to the kitchen, the expansive Great Room offers plenty of space for hosting family and friends in comfort. The luxurious primary suite is a tranquil retreat with direct access to the pool, featuring two spacious walk-in closets, a spa-like en-suite bathroom with a garden tub, dual vanities, a private water closet, and a walk-in shower. The additional guest bedrooms share a Jack and Jill bathroom, ideal for family or guests, while a third bathroom is conveniently located near the pool, providing easy access for outdoor gatherings. Outside, the large screened-in pool area is surrounded by lush tropical landscaping, creating a serene oasis for relaxation and outdoor entertaining. In addition to the stunning home, the Keene’s Pointe community offers an unparalleled lifestyle with access to the private member Golden Bear Golf Club, an 18-hole Jack Nicklaus Signature-designed course. Residents can also enjoy a range of private amenities with club membership, including a fitness center, tennis courts, a resort-style pool, and a clubhouse with dining options. Nestled along the Butler Chain of Lakes, the community offers breathtaking views, natural beauty, and plenty of outdoor recreation. This home provides not only a luxurious living experience but also the opportunity to be part of one of the most exclusive communities in Windermere.

11721 Camden Park Drive, Windermere
$1,249,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe - 24 hour gated/attended community in Windermere, Florida. Situated on the 1st fairway of The Golden Bear Club, this quaint villa-style home offers 4 bedrooms, 3 baths, formal dining and an open kitchen/great room floor plan. As you enter, you are greeted by the spacious dining room and split bedroom plan. The primary suite is oversized and offers French doors accessing the lanai, bathroom with jacuzzi tub, shower and dual vanities and 3 spacious custom built closets. In the center of the home is the kitchen and great room with French doors across the back. The kitchen offers stainless appliances, breakfast nook and breakfast bar overlooking the great room with gas fireplace and built-ins. Off the great room is the 4th bedroom or office/den that also offers access to the lanai. There are two additional bathrooms and two bedrooms. Enjoy relaxing or dining in the screened lanai with summer kitchen overlooking the pool/spa and beautiful golf course views. There is also a 2-car garage with additional golf cart bay. Within walking of The Golden Bear Club, a private members-only club featuring golf, tennis, swimming, dining and fitness. Located near shopping, dining, tourist attractions, and major expressways, this home is perfect for full time residency or a second/vacation home. Call today for your private viewing.

6233 Foxfield Ct, Windermere
$2,895,999
5 Beds ⋅ 5.5 Baths ⋅ Casabella Ph 2 SubDv. ⋅ 34786 Zip Code
This beautiful home, built by Toll Brothers in 2019, is located within CASABELLA, one of the more sought-after communities in Central Florida Located in Windermere, this community offers privacy, expansive homes on spacious lots, and luxurious lifestyle. Upon entering this GATED community, you immediately recognize the privacy and beautifully manicured landscapes throughout. This home instantaneously greets you with an expansive driveway and over 5400 square feet of indoor living. Comfort is felt immediately upon entry with APCO Fresh Air UV filtration systems installed on each of the THREE A/C units. Upon entry, you are greeted by a formal great room with marble floors, 25ft ceilings, and floor-to-ceiling windows that create a picture-esc scene overlooking the large swimming pool and spa flooded with an abundance of natural light! Directly adjacent, you will find a beautiful wet bar with wine cellar wall, perfect for gatherings or entertainment! Your first-floor primary bedroom is one of TWO owner’s suites, and boasts large windows with views of the backyard and swimming pool, two large walk-in closets, and flex space that can be used as a gym or private retreat! A stylish bath spa is separate from the shower, as well as THREE vanities! This floorplan offers an additional bedroom with en-suite bath, a spacious laundry room, and an office/craft room on the first level! You will be excited to find a GOURMET KITCHEN, fully equipped with JENNAIR appliances and large island. Enjoy dining here, in a spacious dining nook, or in a strikingly attractive formal dining room! The second level offers the second of the two owner’s suites, and three additional bedrooms that offer private bathrooms. For your outdoor living pleasure, you will find an outdoor kitchen, complete with a never used hibachi-style flattop, expansive gas grill and rotisserie spit rod and two refrigerators! Enjoy seating at the outdoor bar, equipped with surround sound, or create your own design with an abundant amount of hardscape. This beautiful home is minutes away from world-class shopping and dining, close to theme parks, and can be easily accessible to major highways. Schedule your tour today!

4011 Isabella Circle, Windermere
$325,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
A beautiful 3 bedroom first floor condo located conveniently close to the clubhouse which has all the luxury amenities you could ask for. Inside you'll be impressed by the size of the living space which includes a good size living room with separate dining area, and a spacious kitchen with a breakfast bar and stone countertops. All of the bedrooms are great sizes, the master bedroom having its own bathroom and walk-in closet, and a second bathroom for the other bedrooms to share. There is also an enclosed outdoor space which is a great space for sitting out and relaxing. The clubhouse itself is as good as you'll find, with large open spaces for sitting and enjoying the fireplace, kitchen facilities for parties, gym, library and large swimming pool, in addition a volleyball court and playground. Located just 10 mins from Disney's Magic Kingdom this could be the ideal home away from home or investment property.

11434 Jasper Kay Terrace Unit 202, Windermere
$917,500
4 Beds ⋅ 3.5 Baths ⋅ Glenmuir Ut 02 51 42 SubDv. ⋅ 34786 Zip Code
Located in the desirable, gated community of Glenmuir in Windermere, this well-maintained residence offers a blend of comfort and elegance. Featuring four spacious bedrooms, three full bathrooms, and a convenient half bath, this home provides a peaceful retreat within a charming neighborhood. Situated on a sought-after corner lot, this property offers generous space and privacy, with stunning pond views complemented by a serene natural conservation area. Upon entry, you’re greeted by a grand foyer leading to an open, airy layout with high ceilings. To the right of the entrance, you'll find a versatile office space or den, while the spacious living areas include a formal dining room. The gourmet kitchen is a highlight, featuring a large island, custom cabinetry, and seamless integration with the casual dining nook and expansive family room. Seamlessly blending indoor and outdoor living, this home offers the ultimate in Florida lifestyle, with expansive open patio spaces perfect for alfresco enjoyment. The master suite is a tranquil sanctuary, showcasing breathtaking pond views and a spacious, spa-like en-suite bathroom. This luxurious retreat features a generous walk-in closet, a separate shower and soaking tub, dual vanity sinks, and a convenient towel/linen closet. The impressive triple-car garage, along with extra driveway space, offers generous parking accommodations for both residents and guests. Glenmuir is renowned for its top-rated public and private schools, making it Central Florida’s premier educational destination. This exceptional home is just minutes from Disney World, fine dining, upscale shopping, and major attractions like Universal Studios. Enjoy a perfect blend of luxury and convenience in a community featuring a playground, picnic gazebo, basketball court, and scenic ponds. Experience unmatched comfort and access to Central Florida’s finest amenities. Schedule your viewing today and seize this extraordinary opportunity!

10903 Ledgement Lane, Windermere
$1,325,000
5 Beds ⋅ 4 Baths ⋅ Enclave SubDv. ⋅ 34786 Zip Code
Seller may consider buyer concessions if made in an offer ~ There has never been a more perfect blend of modern luxury and the comforts of home! Welcome to the Enclave, a premier Windermere community and this gorgeous 5-bedroom, 4-full bath POOL HOME with versatile bonus space for room to grow plus TOP-RATED SCHOOLS and a WATER VIEW! Immaculately maintained the lush landscaping paired with the TILE ROOF, stacked stone accents and window shutters give you unparalleled curb appeal and the SPLIT GARAGES provide ample parking. The light and bright OPEN CONCEPT main floor delivers not only formal living and dining spaces making gathering with family and entertaining friends a breeze, and a comfortable family room open to a chef’s dream kitchen, but a MAIN FLOOR BEDROOM next to a FULL BATH and MUDROOM complete with built-in shoe storage. Perfectly situated in the heart of the home, the kitchen gives off modem farmhouse vibes while still maintaining a quiet elegance delivering LUXURY VINYL PLANK WOOD FLOORS, shaker style cabinetry that goes all the way to the ceiling, stainless steel appliances, recessed and pendant lighting, stylish backsplash, large island with breakfast bar seating, a casual dining nook overlooking the pool/pond, and a butler’s pantry where you will find a massive WALK-IN PANTRY for endless storage! The second floor of this home is just as impressive with a BONUS/LOFT, three guest bedrooms all featuring walk-in closets and two with en-suite baths, a THEATER ROOM, convenient laundry and the cherry on top is the expansive OWNER’S SUITE. There are five windows for fantastic natural light, a private en-suite bath that rivals a spa and a 16x10 WALK-IN CLOSET with a BUILT-IN CUSTOM STORAGE SYSTEM. This home enjoys no neighbors to the right where you will find the community park/playground and the pond behind is the perfect backdrop to the SCREENED POOL and COVERED LANAI! The Enclave is conveniently located just off Chase Road and SR 535 for easy access to Downtown Windermere, local shopping, restaurants, golf courses, lakes and Hwy 429 if you commute. Zoned for A-RATED SCHOOLS and only minutes from Windermere Prep, this community is also known for its proximity to the Butler Chain of Lakes if you’re seeking the lake life and Disney Parks if you’re an annual pass holder. Filled with upgraded finishes and tons of flexible space, this thoughtfully designed light filled floor plan is ready to welcome you HOME!

17550 Black Rail Street, Windermere
$499,000
3 Beds ⋅ 2.5 Baths ⋅ Windermere Trls Ph 1c SubDv. ⋅ 34786 Zip Code
Experience the enchantment of watching Disney's "Happily Ever After" fireworks from your own home just three miles from Cinderella's Castle. Nestled in the highly desirable Windermere Trails community, this stunning 3-bedroom, 2.5-bath home boasts an open layout that seamlessly connects the kitchen to the living spaces, perfect for entertaining or family gatherings. The second floor features a spacious game room for private entertainment or a cozy hideaway. The primary bath includes a standalone shower and a large walk-in closet. This home also features a brand new privacy fence and a state-of-the-art security system with cameras in the front and back. A brand new washer and dryer convey with the home. Windermere Trails has low HOA fees, and the community amenities are just a few blocks from the home, including a resort-style pool with views of Lake Reams, a splash pad, BBQ area, firework viewing park, playground, dog park, and running and biking trails. Enjoy the convenience of the newer Lakeside Village with dining and shopping, walking distance to the elementary school, A-rated schools, and proximity to Walt Disney World and other Orlando attractions. Schedule your showing today!

10652 Reams Road, Windermere
$950,000
5 Beds ⋅ 4 Baths ⋅ Windermere Isle Ph 2 SubDv. ⋅ 34786 Zip Code
Welcome to 8243 Procida Isle Lane — where luxury meets comfort in every detail. This expansive residence with 5-bedrooms, 4-bathrooms, a stunning pool, and a three car garage, is a true blend of luxury and sophistication, boasting high-end finishes and an enviable outdoor space perfect for entertaining or relaxation. As you approach the home, you are greeted by a striking façade featuring elegant stone accents and towering cypress trees, setting the stage for the sophisticated design that awaits inside. Step through the inviting arched entryway into a world of refined living. The heart of this home is the chef’s kitchen, a culinary masterpiece adorned with top-of-the-line stainless steel appliances, gleaming granite countertops, and a large central island that provides both functionality and a gathering place for family and friends. The adjacent living area is bathed in natural light, thanks to large windows that perfectly frame views of the meticulously designed outdoor space. Step outside to your private oasis—a resort-style pool surrounded by lush greenery and tall hedges, ensuring your privacy. The pool area features elegant water features and ample deck space, making it the perfect spot for entertaining or unwinding after a long day. The covered lanai, with ceiling fans and room for outdoor dining, extends your living space outdoors, allowing you to enjoy Florida’s beautiful weather year-round. Retreat to the luxurious primary suite, a haven of tranquility with a spacious layout that includes a sitting area, custom walk-in closets, and a spa-inspired en-suite bathroom complete with a soaking tub, separate shower, and dual vanities. The additional bedrooms are equally well-appointed, each offering en-suite bathrooms and generous closet space, making this home ideal for both family and guests. Additional highlights of this property include a three-car garage, high ceilings, coffered ceilings, elegant lighting fixtures, and a well-manicured front yard that adds to the home’s stunning curb appeal. HOA includes lawn care and fertilizer, a community pool, a cabana, a playground, and park benches by the fountain and discounted Spectrum TV and internet services - the complete package! Located in a sought-after Orlando community, this home offers convenient access to top-rated schools, shopping, dining, and the best attractions Central Florida has to offer. This home is the epitome of high-end living in Orlando, offering a perfect blend of luxury, privacy, and convenience. Don’t miss your chance to make this extraordinary property your forever home!

8243 Procida Isle Lane, Windermere
$4,999,000
4 Beds ⋅ 5.5 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code
Keene's Pointe - 24-hour gated/attended community in highly desired Windermere, Florida. This completely renovated home features formal living and dining rooms, great room, spacious and well-equipped kitchen, 4 bedrooms, 5 full and 1 half bath and a second floor bonus suite. No detail was spared in this modern and functional home located on the 17th tee of The Golden Bear Club. As you enter the circular drive into the modern pivoted front door you are encompassed with style and elegance. There are vaulted and wood beamed ceilings, porcelain floors, wood and porcelain wall details, custom lighting, drapes/shades, and much more! The great room, living room and dining room are open and adjoin the over 1,100 square feet of enclosed lanai space overlooking the golf course with air conditioning, kitchen and bath. The primary suite is an oasis with dual vanities, large shower, free-standing tub and large walk-in closet. There are also two offices with built-ins as well as a spacious laundry room and 4-car garage. This home was designed with entertaining in mind. Close to shopping, dining, expressways and tourist attractions, this home has it all!

6719 Valhalla Way, Windermere
$875,000
5 Beds ⋅ 3 Baths ⋅ Manors At Butler Bay SubDv. ⋅ 34786 Zip Code
Incredible opportunity in the established neighborhood of The Manors at Lake Butler. Enjoy a peaceful drive through majestic oaks to your custom home on over half acre lot. Incredible curb appeal, long driveway for parking and massive back yard. Enter to elegant formal living and dining room with soaring ceilings, crown molding and Florida sunshine glistening off the wood floors. A timeless floor plan of predominantly 1 story living with a bonus room and 5th bedroom above the garage will check all your must haves. The heart of the home is the open kitchen with custom cabinetry, fully vented gas cooktop and island overlooking the family room with prefect views of your pool and back yard. The custom built ins and gas fireplace are the focal point of the family room. The owners suite is HUGE with tray ceiling and french doors leading to the covered lanai. The owners retreat covers all your needs... 2 walk in closets, his/her vanities, large jacuzzi jetted tub and large shower. the 3 way split floor plan gives everyone their own space and the 5th bedroom and bonus room above the garage has additional mini split ac unit too. You will truly benefit from the oversized side entry 2 car garage complete with additional 220 amp service, perfect if you have EV vehicles or like love wood working. Incredible back yard with SCREENED SALT WATER pool & spa. Massive back yard is an open canvas to put your personal touches on. Kinetico Filtration System on well is 3 years new (no water bills here !!!) , Roof is 2016, AC is 2015 and all duct work has recently been replaced in the home too. Sought after K-12 school district, Windermere Elementary is directly next door to the community. A huge plus to owning this home is the DEEDED ACCESS to the Town of Windermere Chain of Lakes private boat ramps ... plus the tennis courts next to community. The Manors at Lake Butler is an established neighborhood and very rare to have a home of this quality become available – Close to the 408, 429, Turnpike and a short drive to Winter Garden Village, Restaurant row, international drive, Sea World, Universal Studios and Disney. – 2 major hospitals within 5 miles and endless dining and shopping options in every direction. Golf Cart friendly & miles of sidewalks for getting exercise by walking or riding your bike . Access to Basketball, Tennis & Pickle Ball Courts. Do not forget the Friday morning Farmers market down the road. You will not find a better value in the entire zip code.

2544 Carter Grove Circle, Windermere
$830,000
6 Beds ⋅ 3.5 Baths ⋅ Windermere Sound SubDv. ⋅ 34786 Zip Code
Seller may consider buyer concessions if made in an offer ~ Welcome to Windermere Sound, a vibrant community just miles from Magic Kingdom for a view of Disney fireworks every night, and this expansive executive home offering 6-bedrooms, 3-full and 1-half baths, formal, family and flex space and a screened lanai and patio complete with a Summer kitchen! The paver driveway, manicured landscaping and covered front porch exude curb appeal while welcoming you home. Step through the front door and info a light and bright split bedroom floor plan with a formal dining room to your left and a natural flow into the kitchen and great room. Designed with the home chef in mind the kitchen delivers rich cabinetry for ample storage, including a butler’s pantry, STAINLESS STEEL APPLIANCES, crown molding, GRANITE COUNTERS and breakfast bar seating on the large ISLAND. The kitchen is open to a casual dining space and the family room beyond where a wall of windows looks out onto the lanai and lets the natural light pour in. Before heading upstairs tour the MAIN FLOOR PRIMARY SUITE, a true escape for the homeowner with a lovely tray ceiling, WALK-IN CLOSET and private en-suite bath. Start and end your day in the well appointed en-suite boasting DUAL/SPLIT VANITIES, a SOAKING TUB and separate glass enclosed shower. Upstairs you will find a versatile LOFT space perfect for a second living area, media room, game room or anything else you or your family might need. There are also five sizable bedrooms all featuring walk-in closets! Outside the covered lanai has been extended and screened for maximum enjoyment and includes the perfect OUTDOOR KITCHEN making gathering with family and entertaining friends a breeze. The yard is fenced for added privacy when you want to stay home and the community amenities are located just across the street when you want to venture out and meet your neighbors! For those that love the park hop this home is ideally located close to all the attractions Central Florida is known for with the Magic Kingdom in your backyard for a nightly view of fireworks throughout the year! If that weren’t enough Windermere Sound also offers residents a community pool, tennis and basketball courts plus easy access to local shopping, restaurants and so much more. With flexible space and room to grow, there is something for everyone to love about Penkridge Lane. Call today to schedule a showing!

7336 Penkridge Lane, Windermere
$340,000
3 Beds ⋅ 2.5 Baths ⋅ Oasis Cove Ii At Lakeside Village SubDv. ⋅ 34786 Zip Code
Welcome to this charming 3-bedroom, 3-bathroom home located in the sought-after Oasis Cove community, just minutes from the magic of Disney World! This beautifully maintained home offers a bright and open floor plan, perfect for both everyday living and entertaining. The gourmet kitchen features granite countertops, stainless steel appliances, and a large island, making it a chef's dream. The spacious primary suite boasts a walk-in closet and an en-suite bathroom with a separate shower, and dual vanities. Two additional bedrooms provide plenty of space for family or guests, with easy access to the other bathrooms. Step outside to enjoy the lanai and beautifully landscaped backyard—ideal for relaxing after a long day at the nearby theme parks. This home is perfectly situated just a short drive from Disney World, making it a great choice for those looking to be near world-class entertainment, shopping, and dining. Community amenities include a resort-style pool, playground, and walking trails. With top-rated schools and easy access to major highways, this home truly has it all! Don’t miss out on this fantastic opportunity—schedule your private showing today!

14276 Desert Haven Street Unit GE, Windermere
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