Winter Garden Homes with Sidewalk Exterior Features

Winter Garden Homes with Sidewalk Exterior Features

Welcome to Winter Garden, Florida – a vibrant city nestled in the heart of Orange County, where charming neighborhoods and a rich history blend seamlessly with modern conveniences. Known for its picturesque downtown area, Winter Garden boasts a delightful mix of unique shops, exquisite dining options, and a thriving arts scene. With its lush parks, scenic lakes, and well-maintained walking trails, this city is perfect for those who appreciate the beauty of nature while enjoying the comforts of suburban living.

One of the standout features of homes in Winter Garden is their inviting sidewalk exterior. These beautifully designed homes not only enhance the community’s aesthetic appeal but also promote a friendly, walkable environment. Picture yourself strolling down tree-lined streets, greeting neighbors, and taking in the delightful sights and sounds of this charming city. Sidewalks create a sense of connection, encouraging families and friends to gather, exercise, and explore everything Winter Garden has to offer.

In addition to its stunning homes with sidewalk features, Winter Garden is known for its strong sense of community. Residents enjoy year-round events, from farmers' markets to seasonal festivals, ensuring there’s always something fun happening. With top-rated schools, excellent recreational facilities, and easy access to major highways, Winter Garden is not just a place to live but a place to thrive.

Discover your dream home in Winter Garden, where community spirit meets modern living, and every day feels like a celebration of life. Come experience the charm and warmth of this remarkable city!

Newest Winter Garden Homes with Sidewalk Exterior Features

13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden

3275 Buoy Circle, Winter Garden
$740,000
5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. SPACIOUS LUXURY LIVING + 5 BEDROOMS + 4.5 BATHROOMS + 2 FLEX SPACES + GATED COMMUNITY! Welcome to this stunning YORKSHIRE MODEL in the highly desirable LAKEVIEW PRESERVE community of Winter Garden! Designed with space, comfort, and versatility in mind, this beautifully appointed home offers an exceptional floor plan ideal for MULTIGENERATIONAL LIVING, WORKING FROM HOME, AND ENTERTAINING. Featuring 5 generously sized bedrooms, 4 full bathrooms, a half bath, TWO FLEX SPACES—ONE ON EACH LEVEL, and an oversized lot with an open green backyard, there's room for everyone to spread out and enjoy! From the moment you enter, you'll appreciate the thoughtfully designed layout, 8-foot interior doors, abundant natural light, and stylish designer finishes. The OPEN-CONCEPT FLOOR PLAN flows seamlessly from the spacious gathering room into the dining area and GOURMET KITCHEN, featuring QUARTZ COUNTERTOPS, 42-INCH SOFT-CLOSE CABINETRY, BUILT-IN APPLIANCES, a decorative wood canopy hood, designer tile backsplash, oversized center island, and walk-in pantry. Expansive POCKET SLIDING GLASS DOORS open to the impressive 22-FOOT COVERED LANAI, NOW SCREENED IN BY THE CURRENT OWNERS, creating the perfect setting for indoor-outdoor entertaining while overlooking the spacious backyard. One of this home's greatest advantages is its FLEXIBLE, MULTIGENERATIONAL-FRIENDLY FLOOR PLAN. The FIRST-FLOOR GUEST SUITE WITH PRIVATE EN-SUITE BATHROOM AND WALK-IN CLOSET provides an ideal retreat for extended family, overnight guests, or anyone seeking additional privacy. A versatile FIRST-FLOOR FLEX SPACE offers the perfect opportunity for a home office, playroom, or additional living area. Upstairs, a SECOND SPACIOUS FLEX SPACE provides even more possibilities for a media room, game room, study area, or separate gathering area, allowing everyone to enjoy their own space. The upstairs PRIMARY SUITE is a relaxing private retreat featuring a large walk-in closet and a beautifully appointed en-suite bathroom with DUAL QUARTZ-TOPPED VANITIES, AN OVERSIZED WALK-IN SHOWER, and a private water closet. Three additional upstairs bedrooms, including one with its own EN-SUITE BATHROOM, offer comfortable accommodations and generous closet space. The upgraded laundry room adds convenience with cabinetry, quartz countertops, and a utility sink. Additional highlights include PORCELAIN TILE FLOORING throughout the main first-floor living areas, designer bathroom finishes, ample storage throughout, outdoor kitchen pre-plumbing, and a 2-CAR GARAGE WITH NEWLY ADDED EPOXY FLOORING for a clean, finished look. Located within the sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE, residents enjoy RESORT-STYLE AMENITIES, including a sparkling pool with splash pad, clubhouse, fitness center, playground, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE. Even better, the community has NO CDD FEE! Just approximately 5 miles from charming DOWNTOWN WINTER GARDEN and minutes from SR 429, you'll enjoy convenient access to shopping, dining, entertainment, and major Central Florida roadways. Experience the space, flexibility, and lifestyle this exceptional Winter Garden home has to offer. Schedule your private showing today!

3275 Buoy Circle, Winter Garden

2199 White Feather Loop, Oakland
$489,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland

15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden

1444 Kenny Court, Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ Kenny Court SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-Bedroom, 2-Bath single-story home in a DESIRABLE LOCATION near Winter Garden, offering a spacious CORNER LOT, NO HOA and plenty of room to make the most of Florida living! Set on NEARLY A QUARTER ACRE, the property features MATURE SHADE TREES, a large driveway with ample parking and a welcoming setting. Inside, BEAUTIFUL LVP FLOORING and NEW LEVELOR BLINDS throughout, create a fresh, cohesive look, while NEW AC (2026) and a ROOF REPLACED IN 2022 add peace of mind. The OPEN FLOOR PLAN allows the Living Room, Dining Room and Kitchen to flow together seamlessly, creating a comfortable setting, while NATURAL LIGHT fills the space, enhancing the bright and airy feel. The Kitchen offers plenty of SOLID WOOD WHITE CABINETRY, solid-surface countertops and a center island with breakfast bar seating. A RECENTLY UPDATED TILE BACKSPLASH adds a stylish finishing touch, while STAINLESS STEEL APPLIANCES—including a GAS STOVE—make meal preparation a pleasure. A window above the sink brings in NATURAL LIGHT and provides a view of the backyard, and a CONVENIENT LAUNDRY ROOM is located just off the Kitchen. Down the hallway, you’ll find THREE BEDROOMS, each featuring a STYLISH CEILING FAN and WALK-IN CLOSET for comfortable living and convenient storage. The Primary Suite presents a private retreat with its own en suite Bath, complete with a MODERN VANITY AND TILED WALK-IN SHOWER. A SECOND FULL BATH with a modern vanity and tub/shower combination, is conveniently located near the additional Bedrooms.The Kitchen provides access to the backyard, where there's an OPPORTUNITY to create an outdoor space that reflects your own style, whether you envision a GARDEN, entertaining area or a place to relax under the Florida sunshine. With its GENEROUS CORNER LOT, mature shade trees and NO HOA, there’s room to make this property your own. Enjoy a GREAT LOCATION, just 2 miles from the charm and character of HISTORIC DOWNTOWN WINTER GARDEN, where you can explore local shops and restaurants, browse the popular PLANT STREET MARKET, visit the SATURDAY FARMERS MARKET or catch a show at the GARDEN THEATRE. Outdoor enthusiasts will appreciate the nearby WEST ORANGE TRAIL, ideal for biking, jogging and leisurely strolls, and with CONVENIENT ACCESS to Florida's Turnpike and SR-429, you can easily reach Orlando’s WORLD-FAMOUS THEME PARKS. Families will appreciate the nearby GREAT SCHOOLS including, A-RATED William Maxey Elementary and West Orange High School, adding to the appeal. With its thoughtful updates, GENEROUS LOT and convenient access to everything WINTER GARDEN has to offer, this home is FULL OF POTENTIAL and ready for its next chapter. Call and schedule your private tour today!

1444 Kenny Court, Winter Garden

622 Sigler Drive, Winter Garden
$604,580
3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Gardenia floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, Calacatta countertops, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

622 Sigler Drive, Winter Garden

15613 Boggy Oak Circle Unit 110A, Winter Garden
$299,900
2 Beds ⋅ 2 Baths ⋅ Tucker Oaks Condo SubDv. ⋅ 34787 Zip Code
MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!

15613 Boggy Oak Circle Unit 110A, Winter Garden

900 Allendale Lane, Oakland
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code
Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland

17600 Lake Star Road, Winter Garden
$1,350,000
5 Beds ⋅ 4 Baths ⋅ Northlake/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
Discover exceptional lakefront living in Northlake at Ovation, where this extensively upgraded Ashton Woods residence showcases more than $320,000 in builder design selections and owner-added enhancements. Thoughtfully curated interiors, distinctive architectural details, and inviting outdoor spaces create a home equally suited to elegant entertaining and everyday comfort. A soaring foyer, statement chandelier, and beautifully detailed staircase establish an impressive arrival. Natural light fills the living spaces, highlighting plantation shutters, upgraded tile and hardwood flooring, custom wall treatments, and designer lighting throughout. The separate dining room provides an elegant setting for gatherings, while the kitchen, breakfast area, and family room flow seamlessly together. At the heart of the home, the beautifully appointed kitchen pairs an expansive contrasting island with designer quartz countertops, stacked cabinetry, and illuminated display accents. A custom backsplash and mural extending to the ceiling create a striking focal point, complemented by stainless steel appliances, pendant lighting, and a custom-organized pantry. The primary suite creates a peaceful retreat with hardwood flooring, generous windows, and a custom walk-in closet. Its spa-inspired bathroom features a soaking tub, separate vanities, upgraded fixtures, and an expansive frameless glass shower framed by striking tilework. Additional bedrooms and bathrooms carry the home’s thoughtful design throughout, including custom closet systems in the downstairs bedroom and designer accent walls in the downstairs bathroom. A dedicated office and spacious upstairs loft provide versatile settings for work, leisure, and recreation. Outdoor living unfolds beneath a covered paver lanai with roll-up screens and a custom summer kitchen featuring a built-in grill, beverage chiller, sink, upgraded countertops, and integrated storage. Generous dining and lounging areas overlook the fenced backyard, mature greenery, and tranquil lakefront setting—an inviting backdrop for morning coffee or evening gatherings. Beyond its beautiful finishes, the home incorporates carefully considered functionality: a custom laundry room with cabinetry and a sink, a drop zone, custom storage, whole-house gutters, backyard French drains, and pre-plumbing for a water softener. A hardwired security system and cameras, along with hardwired internet and Ethernet connections at TVs, provide added convenience. The garage includes epoxy flooring, overhead smart storage racks, cabinetry, and a utility sink. Redesigned landscaping and architectural uplighting enhance the home’s presence after sunset. Northlake at Ovation amenities include a community pool, clubhouse, playground, and dog park. Nearby Hamlin Town Center and Winter Garden Village provide shopping, dining, and entertainment, while Historic Downtown Winter Garden invites exploration of its boutiques, restaurants, celebrated farmers market, and West Orange Trail. Walt Disney World and Central Florida’s renowned attractions are within reach, with SR 429 connecting you to the greater Orlando area. Experience beautifully appointed interiors, extensive upgrades, and inviting lakefront living in this exceptional Winter Garden residence. Schedule your private showing.

17600 Lake Star Road, Winter Garden

1210 Brandy Lake View Circle, Winter Garden
$450,000
3 Beds ⋅ 2 Baths ⋅ Brandy Creek SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable gated community of Brandy Creek in Winter Garden! Step inside to discover an inviting, open layout where the living area flows seamlessly into the kitchen and dining space, creating a comfortable setting for everyday living and entertaining. The kitchen features granite countertops and ample cabinetry for storage. French doors open to an extended screened-in lanai, providing the perfect space to relax, entertain, or simply enjoy the Florida lifestyle. The fenced backyard offers additional room for outdoor activities, pets, or gatherings with family and friends. The primary suite features a walk-in closet and an en-suite bathroom with dual sinks, a garden tub, and a separate shower. The additional bedrooms provide comfortable, flexible spaces for family, guests, or a home office. With generous living spaces and the opportunity to add your own personal touches, this home offers wonderful potential to make it truly your own. Beyond the home, Brandy Creek offers a peaceful setting with tranquil ponds, a scenic lake, and a community fishing pier. Just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to the popular West Orange Trail, Saturday Farmers Market, live music, boutique shopping, and an incredible variety of local restaurants. Convenient access to the Florida Turnpike and SR-429 makes commuting and exploring Central Florida a breeze. Whether you're enjoying a quiet evening on your screened lanai or exploring the charm of downtown Winter Garden, this home offers a wonderful combination of space, location, and lifestyle. Don't miss the opportunity to make it your own!

1210 Brandy Lake View Circle, Winter Garden

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