Windermere Homes with Sidewalk Exterior Features

Windermere Homes with Sidewalk Exterior Features

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

Nestled in the heart of Central Florida, Windermere is a highly sought-after community for homebuyers looking for a peaceful retreat. With its close proximity to Orlando, residents can enjoy easy access to world-class theme parks, shopping centers, and entertainment options, while still being able to come home to a serene and tight-knit community.

One of the standout features of homes in Windermere is their stunning sidewalk exterior features. True to their commitment to creating a safe and pedestrian-friendly environment, many homes in this area boast sidewalks that meander through the neighborhoods, inviting residents to take leisurely strolls and enjoy the beautiful surroundings.

These sidewalks not only enhance the aesthetic appeal of the homes but also promote a healthy and active lifestyle. Whether you want to go for a morning jog, take a leisurely walk with your family, or simply enjoy the fresh air, the sidewalks in Windermere make it convenient and enjoyable to do so.

With a variety of architectural styles and sizes to choose from, Windermere offers a range of homes to suit different preferences and budgets. From cozy bungalows to luxurious estates, there is something for everyone in this charming town.

If you're looking for a place that combines natural beauty, a close-knit community, and homes with sidewalk exterior features, Windermere is the perfect destination for you. Come and discover the magic of this enchanting town and find your dream home in Windermere, Florida.

Newest Windermere Homes with Sidewalk Exterior Features

4936 Wise Bird Drive, Windermere
$535,000
4 Beds ⋅ 3 Baths ⋅ Summerport Creeks Run SubDv. ⋅ 34786 Zip Code
Welcome home to your immaculate and move in ready single story home in desirable Summerport with A-rated schools and the Keene's Crossing Elementary School conveniently located a bike ride away within the community and Windermere High School across the street. School commute convenience at its best!!! This light & bright functional floor plan has been recently painted inside and out with a brand new roof in 2025 and new HVAC in 2020, and is the ideal first home for a growing family, a vacation home to get away from those cold winters, or even a retirement home or investment property. From the minute you enter through the covered front porch you are greeted by upgraded Luxury Vinyl Plank flooring through all the living areas and bedrooms with ceramic tile floors in the kitchen and wet areas. The formal living and dining rooms are located across from one another and can serve as the desired flex space that you need making them ideal as a home office, media or game room, home theatre or play room. The kitchen is conveniently located adjacent to the formal living room and features upgraded Quartz counter tops with new appliances in 2021 with a natural gas stove and a brand new dishwasher in 2026. You will literally be cooking with gas in this home...The inviting family room opens up to the kitchen making this the ideal floor plan to entertain your guests and serve your favorite culinary creations on the breakfast bar. The breakfast nook offers serene views of your private wooded backyard. Your master retreat is privately tucked away in the back of the home and features serene wooded views of your private back yard, a spacious walk-in closet and an en suite bath with dual vanities, a garden tub, separate shower and bathrooms stalls. The adjacent bedroom with full bath is ideal for a close by nursery or home office. Bedrooms 2 and 3 are located on the opposite side of the home with a shared bath; ideal as guest bedrooms or the private space that your teenagers need. Long hot showers are as economical as it gets thanks to the natural gas water heater from 2020. Summerport community offers a clubhouse with a hall featuring a cozy fireplace and fully equipped kitchen, a well equipped gym, community swimming pool, tennis and basketball courts, lake front beach volleyball court, playgrounds and BBQ areas. All this in a excellent location conveniently located to grocery stores, shopping, hospitals and a short trip to the area attractions and the airport.

4936 Wise Bird Drive, Windermere
8867 Herencia Alley, Windermere
$405,000
3 Beds ⋅ 3 Baths ⋅ Legado SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful townhome in the desirable Legato community in Windermere! This spacious 3-bedroom, 2.5-bathroom home features an open floor plan and a 2-car garage, offering comfort, functionality, and convenience. Enjoy the community swimming pool and a prime location near Walt Disney World, shopping centers, restaurants, and everyday amenities. The property is currently vacant and ready for its next owner. With HOA allowing long-term rentals, this home presents an excellent opportunity for both owner-occupants and investors seeking a rental property in a desirable location. Don’t miss this opportunity!

8867 Herencia Alley, Windermere
8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
5944 Caymus Loop, Windermere
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an oversized paved patio and custom pergola seating. Privacy is included with the 6 ft vinyl fence. New Roof ('20), AC units(’18/’19), Hot Water Heater (’21/Natural Gas), Exterior Paint(’20) Shallow well for irrigation, termite bond, 5 Camera Ring System (8/21) including Flood lights and doorbell, expanded paver driveway (2025) for additional parking, blinds and plantation shutters, central vacuum system, and new septic pump('22) are just a few of the great features of this home. Located close to dining, shopping, expressways, tourist attractions, and top-rated public and private schools, this home and community has it all!

5944 Caymus Loop, Windermere
7231 Sangalla Drive, Windermere
$1,348,000
5 Beds ⋅ 5 Baths ⋅ Casa Del Lago-Replat SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of interior space with a private pool and a location remarkably connected to the destinations that define Southwest Orlando. Recently refreshed, the residence features newly painted interiors and new light white oak luxury vinyl flooring throughout the home, excluding the bathrooms. The result is a lighter, more contemporary palette that carries naturally from room to room and gives the home an entirely new point of view. At the center of the main level, the kitchen combines granite countertops, an oversized island, stainless steel appliances, gas cooking and generous cabinetry and pantry storage. It opens to the living and breakfast areas, creating one continuous space for daily living and entertaining. A formal dining room and dedicated office add definition to the floor plan without interrupting its openness. The first-floor primary suite offers a spacious retreat with a walk-in closet, dual vanities and oversized walk-in shower. Additional bedrooms provide flexibility for guests, work or creative space, while the approximately 448-square-foot upstairs bonus room adds another layer of versatility for a media lounge, game room, fitness space or secondary living area. Outside, the architecture gives way to a distinctly Florida setting. A screened swimming pool, covered lanai and expansive paver deck extend the living space outdoors, complemented by low-maintenance turf and additional backyard space. A three-car garage completes the residence. Casa Del Lago is positioned within Windermere’s Lake Burden area, placing the home near Lakeside Village, Hamlin, Downtown Windermere, Golden Oak, Four Seasons Resort Orlando, Walt Disney World Resort and the Sand Lake Road dining district known as Restaurant Row. The location offers convenient access to shopping, dining, entertainment and major roadways while maintaining the privacy of a gated residential setting. A refreshed interior, private outdoor living and a Windermere address positioned at the center of it all.

7231 Sangalla Drive, Windermere
12785 Westside Village Loop, Windermere
$799,000
4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code
MOVE-IN READY WINDERMERE HOME WITH CONSERVATION POND AREA! Located in desirable Westside Village, this 4-bedroom, 3.5-bath home offers an open floor plan, tiled roof, landscaped yard, spacious front porch, and a peaceful conservation-view backyard. The bright kitchen overlooks the living room and breakfast nook and features granite countertops, stainless steel appliances, and a large center island with seating and storage. French doors open to the patio, creating an easy connection between indoor and outdoor living. Enjoy resort-style amenities including a community pool, clubhouse, playground, paved walking trails, and beautiful water features. Ideally located near top-rated schools, shopping, restaurants, major highways, and Walt Disney World just minutes away. Experience the best of Windermere living in a highly sought-after community. Schedule your showing today—this move-in-ready home won't last!

12785 Westside Village Loop, Windermere
11963 Vermillion Avenue, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION! Welcome to Windermere Trails, one of Windermere’s most desirable communities. This beautiful 3-bedroom, 2.5-bath townhome offers 1,676 sq. ft. of living space, a 2-car garage, and an unbeatable location just steps from Bay Lake Elementary School. Enjoy the convenience of having shopping, dining, and everyday essentials nearby, including Publix at Lakeside Village, while being just minutes from Walt Disney World and major roadways. The home features an open and functional floor plan, stainless steel appliances, ceramic tile throughout the first floor, and spacious living areas designed for comfortable everyday living. Windermere Trails offers resort-style community amenities including a pool, splash pad, playground, dog park, open-air pavilion, walking areas, and beautiful green spaces. Exceptional Windermere location, convenient access to highly regarded area schools, shopping, dining, entertainment, and everything the Horizon West area has to offer. Schedule your showing today!

11963 Vermillion Avenue, Windermere
8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere
6858 Merrick Landing Boulevard, Windermere
$595,000
3 Beds ⋅ 2 Baths ⋅ Vineyards/Horizons West Ph 1a SubDv. ⋅ 34786 Zip Code
YOUR OWN PRIVATE SPA, A WINDERMERE ADDRESS, AND LANDSCAPING YOU DON’T HAVE TO WORRY ABOUT—6858 Merrick Landing Blvd makes Florida living easy. Located in the desirable community of THE VINEYARDS IN WINDERMERE, FL, this spacious 3-BEDROOM, 2-BATH HOME + BONUS ROOM offers 2,115 SQ FT of thoughtfully designed single-story living with a split floor plan that creates both connection and privacy. Step inside to an open and inviting interior with vaulted ceilings, crown molding, and a kitchen positioned at the heart of the home featuring an OVERSIZED CENTER ISLAND, GRANITE COUNTERTOPS, 42-INCH CABINETRY, STAINLESS STEEL APPLIANCES, and a walk-in pantry overlooking the main living and dining spaces. The BONUS ROOM gives you valuable flexibility without sacrificing a bedroom—perfect for a home office, media room, playroom, fitness space, or second lounge. Privately positioned away from the secondary bedrooms, the OVERSIZED PRIMARY SUITE offers plenty of room for a sitting area, along with a generous walk-in closet and en-suite bath featuring dual vanities and a large walk-in shower with bench. Outside, unwind in your own PRIVATE IN-GROUND SPA, creating a relaxing retreat for quiet mornings or Florida evenings at home. Life in THE VINEYARDS makes ownership even easier, with the HOA including LANDSCAPING/GROUND MAINTENANCE AND PEST CONTROL, plus access to a community pool, parks, playgrounds, sidewalks, and green spaces. The location is another major advantage—currently zoned for INDEPENDENCE ELEMENTARY, BRIDGEWATER MIDDLE, AND WINDERMERE HIGH SCHOOL, with Windermere High located directly nearby, while HORIZON WEST, HAMLIN, WINTER GARDEN VILLAGE, DISNEY SPRINGS, WALT DISNEY WORLD, shopping, dining, and major roadways are all within convenient reach. At 6858 Merrick Landing Blvd, the location is desirable, the floor plan is flexible, and the lifestyle is refreshingly easy. Schedule your private showing today.

6858 Merrick Landing Boulevard, Windermere
7030 Mapperton Drive, Windermere
$649,000
4 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your own private pool retreat in this immaculate, move-in-ready home in the desirable Lakes of Windermere community. Featuring four bedrooms, three bathrooms, and 2,455 square feet of thoughtfully arranged living space, this inviting single-story residence features an expansive open floor plan. A roof replaced in 2023, air-conditioning system replaced in 2021, new water heater, and newly replaced pool cage screens add meaningful value to a home that is beautifully prepared for its next chapter. A welcoming covered front porch overlooks the treed community park across the street, creating a peaceful setting for morning coffee or an unhurried evening outdoors. Inside, generous living spaces and an airy, flowing layout provide room to gather, entertain, and settle comfortably into everyday life. The spacious formal living and dining areas offer flexibility for both intimate occasions and larger celebrations, while the heart of the home unfolds into an expansive kitchen and adjoining family room. A preparation island, breakfast bar, abundant cabinetry, generous counter space, dual dining room options and stainless steel appliances make the kitchen as practical as it is inviting. Its open connection to the family room keeps conversation flowing and brings the main living spaces together with views toward the pool. Privately positioned within the floor plan, the spacious primary suite offers a relaxing escape, complemented by two walk-in closets and an en-suite bathroom with separate vanities, a soaking tub, and a separate shower. Three additional bedrooms provide comfortable accommodations and flexibility for guests, a home office, or creative pursuits, while a conveniently located half bathroom serves the main living area. Outdoors, the screened private pool becomes a natural extension of the home, offering space to unwind in the sunshine or enjoy a refreshing swim. The covered lanai provides a shaded setting for outdoor dining and entertaining, with a built-in exhaust hood for your BBQ setup and mature landscaping that enhances the inviting surroundings while providing a completely private pool area. An attached two-car garage accessed from the rear preserves the welcoming character of the front elevation while adding everyday convenience. Beyond the home, Lakes of Windermere offers a large community pool and sun deck, tennis, basketball, and volleyball facilities, three playgrounds, and a fishing pier on Lake Sawyer. Pine Loop Park adds a shaded gathering gazebo and an approximately 0.9-mile sidewalk loop for leisurely walks or an afternoon jog. Ideally located close to A-List schools, all four Walt Disney World theme parks and resorts, with shopping, dining, and daily conveniences nearby, this beautifully maintained residence brings together spacious interiors, inviting outdoor living, valuable updates, and a prime Windermere setting. Call me to schedule your private showing now.

7030 Mapperton Drive, Windermere
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
8524 Vivaro Isle Way, Windermere
$950,000
4 Beds ⋅ 3 Baths ⋅ Windermere Isle-Ph 2 SubDv. ⋅ 34786 Zip Code
Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer's interest rate buy-down. As an additional incentive, the seller is offering a home warranty that can be transferred to the new homeowner, providing added peace of mind. Welcome to 8524 Vivaro Isle Way, a beautifully appointed home in the sought-after Windermere Isle community. Designed for both everyday comfort and entertaining, this home features a private custom pool, upgraded 42" kitchen cabinetry with crown molding, granite countertops, upgraded cabinet hardware, a single-basin undermount sink, and a stylish kitchen backsplash. Upgraded tile flooring extends through the foyer, dining room, family room, office, gallery, kitchen/breakfast area, laundry room, and bathrooms, while the remaining living areas feature carpet. The primary suite offers a raised-height vanity, upgraded undermount sink, semi-frameless shower enclosure, tiled shower, and ceiling-mounted rain shower. Additional upgrades include 8' interior doors, blinds throughout operable windows, a 9' sliding glass door, upgraded bathroom vanities, and upgraded interior finishes. All rooms are upgraded with ceiling fans and light fixtures. Step outside to enjoy your own private pool and create the ideal Florida lifestyle with plenty of space to relax, entertain, and enjoy the sunshine. Located in Windermere Isle, this home offers convenient access to shopping, dining, parks, and recreation, with Winter Garden Village, Lakeside Village, Hamlin, and Walt Disney World-area attractions all within the surrounding area. With its combination of thoughtful upgrades, private outdoor living, buyer incentives, and a convenient location near the Windermere and Winter Garden areas, this home offers an ideal place to enjoy Central Florida living.

8524 Vivaro Isle Way, Windermere
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