Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community, Winter Garden offers a delightful blend of small-town charm and modern amenities. With its rich history and abundant recreational opportunities, it’s no wonder that families and individuals are flocking to this beautiful area.

As you explore Winter Garden, you'll discover a variety of homes that cater to diverse lifestyles, particularly those located within the inviting Homes with Sidewalks community. These neighborhoods are designed to foster a sense of connection among residents, featuring well-maintained sidewalks that encourage leisurely strolls and friendly neighborly interactions. Imagine enjoying a morning jog or an evening walk with your loved ones, all while soaking in the warm Florida sunshine.

Winter Garden is also home to a thriving downtown area, where you can find an array of shops, restaurants, and cultural attractions. The historic district, with its charming brick streets and vibrant local businesses, invites you to experience the rich tapestry of community life. Additionally, the city boasts numerous parks and outdoor spaces, perfect for family picnics, weekend sports, or simply unwinding in nature.

With its excellent schools, convenient access to major highways, and a strong sense of community, Winter Garden is an ideal place to call home. Whether you’re looking for a cozy bungalow or a spacious family residence, the Homes with Sidewalks community offers an inviting atmosphere that makes it easy to settle in and make lasting memories. Come discover your dream home in Winter Garden, where community and comfort meet!

Newest Winter Garden Homes with Sidewalks Community Features

3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code

Located in the desirable Winding Bay community in Horizon West, this impeccably maintained home offers 3 spacious bedrooms, 2.5 bathrooms and a versatile flex room that can easily serve as a home office, playroom or potential 4th bedroom. Luxury tile flooring, upgraded in 2025, flows throughout the entire home for a clean and consistent look that is stylish, durable and easy to maintain. The kitchen serves as the centerpiece of the main living space, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, hard-wired under-cabinet lighting and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes bring an elevated feel and distinctive detail to the interior. The spacious owner’s suite features plantation shutters and a beautiful en-suite bathroom, fully upgraded in 2026 with floor-to-ceiling tile, modern finishes and a large walk-in closet. The two secondary bedrooms share a convenient Jack-and-Jill bathroom. Double sliding doors lead to the screened lanai with sun shades, overlooking the fully fenced backyard with iron fencing. In the evening, relax outdoors and enjoy views of the Disney fireworks in the distance, adding a special touch to the Florida lifestyle. Additional features include an extended driveway with pavers, gutters, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen and a dedicated garage outlet for an additional refrigerator or freezer. Solar panels provide an added energy-efficiency benefit, with electric bills averaging approximately $34 during the hot summer months. With no carpet, extensive upgraded tile flooring, flexible living space, a renovated owner’s bathroom, solar panels, and numerous thoughtful upgrades, this Horizon West home is truly move-in ready. This home offers convenient access to shopping, dining, schools, major roadways, and the many amenities throughout Winter Garden and West Orange County. Schedule your showing today!

10750 Petrillo Way, Winter Garden

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

5 Beds ⋅ 4 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this impressive 5-bedroom, 4-bath home with a 3-car garage in the highly desirable Hawksmoor community of Horizon West. Built in 2021, this beautifully designed two-story home offers an exceptionally flexible floor plan, generous indoor and outdoor living spaces, peaceful water and natural views, plus an outstanding energy feature a Tesla whole-home backup power system with solar.One of the home's most valuable upgrades is its Tesla backup battery and solar system designed to provide whole-home backup power. The sellers currently enjoy an electric bill of approximately $34 per month, and the entire solar and battery system will transfer to the new buyer at no additional cost, providing an exceptional combination of energy efficiency, backup power and long-term value.From the moment you arrive, the home makes a great first impression with attractive architectural details, mature landscaping, a paver driveway and three-car garage. Step inside to a welcoming foyer and a dedicated private office, providing an ideal space for working or studying from home.The heart of the home is the expansive open-concept living area, where the kitchen, dining and family rooms flow seamlessly together. The spacious kitchen features an oversized center island with abundant seating, extensive cabinetry and counter space, gas cooktop, built-in oven and microwave, stainless steel appliances and a separate walk-in pantry. Large sliding glass doors fill the living area with natural light and create a wonderful connection to the outdoor living space.The first floor also features a bedroom and full bath, offering excellent flexibility for overnight guests, extended family or multigenerational living.Upstairs, the oversized primary suite provides a relaxing retreat with a tray ceiling, multiple windows and beautiful views. The spacious primary bath features dual vanities, a soaking tub and separate walk-in shower. Additional bedrooms and baths provide plenty of room, while the conveniently located upstairs laundry room makes everyday living easier.An expansive upstairs loft/family room provides an entirely separate living area with endless possibilities as a media room, game room, playroom, fitness area or second family room.Outdoor living is another standout feature. Large sliding doors open to an extended covered lanai overlooking the spacious fenced backyard, water and natural green space beyond. Whether enjoying your morning coffee, entertaining friends or relaxing at the end of the day, this peaceful setting provides an inviting extension of the home with plenty of usable yard space.Beyond the property, Hawksmoor offers an amenity-rich lifestyle with a resort-style community pool, clubhouse, fitness center, playground and outdoor recreation. Located in Horizon West, the community provides convenient access to shopping, dining and entertainment at Hamlin, area parks and trails, SR-429, Walt Disney World and the many attractions of Central Florida. Historic Downtown Winter Garden, with its restaurants, shops, farmers market and West Orange Trail, is also within easy reach.

16773 Wingspread Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code

This stylish townhome in one of Winter Garden’s most desirable resort-style communities, offers a blend of comfort, convenience, and everyday luxury. The home sits in a beautifully planned neighborhood known for its amenities,GainesvillecinfgainesLoo surroundings, and welcoming atmosphere—an ideal setting for anyone seeking a relaxed yet connected lifestyle. Its location is a major highlight. Winter Garden is home to some of Central Florida’s top-rated schools, making this property especially appealing for families who value strong educational options. You’re also just minutes from premier shopping and dining at places like Hamlin Town Center and Winter Garden Village, giving you easy access to everything from groceries to entertainment. And of course, the magic of Disney theme parks is right around the corner, making weekend outings effortless and adding a touch of excitement to everyday life. This townhome places you in a thriving, fast-growing area where convenience meets resort-style living. With beautiful community amenities, excellent schools, nearby shopping, and world-famous attractions close enough to enjoy anytime, it’s a standout opportunity in one of Winter Garden’s most sought-after.

10119 Salt Point Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code

WALK ON IN AND CALL IT HOME! Welcome to this beautiful, almost-new K. Hovnanian home, where thoughtful design, spacious living, and stylish upgrades come together beautifully. As you enter, you’re greeted by a welcoming foyer. To the right are two generously sized bedrooms and a full bathroom. Continue down the hall and discover a functional nook that’s perfect for a home office, study area, or homework station. With its own charming barn door, this space can easily be closed off for added privacy. Just to the right, French barn doors open to a versatile flex space that can be used as an office, formal dining room, or even a fourth bedroom—whatever best suits your lifestyle. Step into the spacious great room and prepare to be impressed! Gorgeous exposed beams create a warm and inviting atmosphere, while the chef-inspired kitchen is the true centerpiece. Featuring ample counter space, a beautiful white farmhouse sink, built-in oven, freestanding oven, stylish range hood, and stunning backsplash, this kitchen is both functional and beautifully appointed. The oversized primary suite offers a peaceful retreat, with a spacious bedroom and a luxurious ensuite bathroom designed with comfort in mind. Enjoy a large walk-in shower, freestanding soaking tub, dual vanities, and an enormous walk-in closet. This thoughtfully designed home also features a generously sized laundry room and mudroom, an oversized garage, and a beautiful lot with a fully fenced backyard—perfect for entertaining, relaxing, or enjoying time outdoors. And the location is just as impressive! Zoned for highly desirable schools and conveniently located near the 429, Turnpike, and 408, with easy access to Disney, shopping, dining, and so much more. With its spacious layout, beautiful finishes, and fantastic location, this home is sure to impress. Schedule your private showing today before this one is SOLD!

13184 Dendy Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome home to a place where life feels just a little easier. Tucked inside the peaceful Westbrook community of Winter Garden, this beautifully maintained, move in ready townhome offers the perfect blend of comfort, style, and convenience. Step inside to discover an inviting open living and dining space that naturally brings everyone together. The heart of the home is the kitchen, thoughtfully designed with gleaming granite countertops, stainless steel appliances, a contemporary tile backsplash, and plenty of space to prepare everything from quick weekday breakfasts to weekend gatherings with friends. Stylish upgraded lighting throughout adds a fresh, modern touch to every room. Upstairs, all three bedrooms create a private retreat away from the main living areas. The spacious primary suite is designed for relaxation and features dual walk in closets, giving everyone room to stay organized. With two additional bedrooms and two and a half bathrooms, there's plenty of flexibility for family, guests, or a dedicated home office. Behind the scenes, a newer high efficiency HVAC system with a UV germicidal light provides year round comfort and added peace of mind. Outside your front door, you'll love being just minutes from Winter Garden Village, the award winning shops and restaurants of Historic Downtown Winter Garden, and the excitement of Disney Springs. Easy access to SR 429 puts Orlando, Tampa, and Central Florida's top attractions within easy reach, making both your daily commute and weekend adventures effortless. Beautiful, meticulously cared for, and ideally located, this is more than a townhome. It's the beginning of your next chapter. Schedule your private showing today.

1017 Priory Circle, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code

FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden

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