Winter Garden Homes with Outdoor Kitchen Exterior Features

Winter Garden Homes with Outdoor Kitchen Exterior Features

Welcome to Winter Garden, Florida—a charming city that perfectly blends small-town warmth with modern conveniences. Nestled just west of Orlando, Winter Garden boasts a rich history, vibrant community, and an array of outdoor activities that make it a sought-after destination for families and individuals alike. With its picturesque historic downtown, lined with unique shops, delightful eateries, and a lively farmers market, residents enjoy a vibrant social scene amidst beautiful surroundings.

One of the standout features of homes in Winter Garden is the allure of outdoor living. Many properties come equipped with stunning outdoor kitchens, transforming backyards into personal oases perfect for entertaining or enjoying quiet evenings under the stars. Imagine hosting summer barbecues with friends and family, whipping up culinary delights while surrounded by lush landscaping and the gentle Florida breeze. These outdoor kitchens often feature state-of-the-art grills, ample counter space, and cozy seating areas, making them the heart of your home’s outdoor experience.

In addition to the outdoor amenities, Winter Garden offers a wealth of recreational opportunities. With numerous parks, lakes, and trails, residents can indulge in activities like hiking, biking, and fishing. The nearby West Orange Trail is a favorite for those who enjoy cycling or leisurely walks amidst nature.

Whether you’re seeking a vibrant community, a home with an inviting outdoor kitchen, or a lifestyle filled with outdoor adventures, Winter Garden, Florida, is the perfect place to call home. Come explore the charm and warmth of this delightful city, where your dream home awaits!

Newest Winter Garden Homes with Outdoor Kitchen Exterior Features

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

234 N Lakeview Avenue, Winter Garden
$2,199,900
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden

8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Turnkey, Toll Brothers model home in Winter Garden. This property occupies one of Lakeshore Preserve’s most open and airy homesites next to expansive open green space inside Lakeshore Preserve. Expansive open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open green space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer upon entering. Key design and home features: Smart home technology, shiplap wall detailing, rich wood-beam ceilings. Plantation shutters throughout. The kitchen features a massive center island, farmhouse sink, abundant cabinetry to include deep drawers. Triple sliding glass doors connect the great room to an expansive screened lanai with a fully equipped outdoor summer kitchen. Outdoor dining and lounge spaces. Motorized retractable screens. Backyard features: outdoor putting green and a built-in stone fireplace with modern glass-rock insert. This home is the ideal Florida seasonal residence or second home. With a resort-style community pool and all grounds maintained by the HOA, this turnkey home is ready for easy seasonal living. First floor primary suite is positioned at the rear of the home. Includes a new walk-in closet, a striking primary bath with opposing vanities, a private water closet and a dramatic walk-in shower. Custom tile extends from the floor up the shower walls, with opposing shower systems, multiple shower heads and built-in bench seating. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes an ensuite bath and full closet, while the other two share a hall bath. When not occupied by guests, the second living room serves as a private lounge, media room, or office space. Turnkey includes: all living area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Utility features to this home: Tankless water heater, in-wall pest system. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds, sand volleyball court. Cable, one-gig internet and ground maintenance are included in the HOA fee. This executive collection home sits on one of the most unique homesites within Lakeshore Preserve. Privacy and sun-drenched light, Toll Brothers coveted upgrades, and this transitional design style fully finished by an interior designer for this model home.

8836 Lakeshore Pointe Drive, Winter Garden

144 Tildenville School Road, Winter Garden
$899,900
3 Beds ⋅ 1 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
The real story of 144 Tildenville School Road is the land. Opportunities to own over an acre this close to Historic Downtown Winter Garden are becoming increasingly hard to find. Beneath a canopy of beautiful mature trees, this property offers something that cannot easily be recreated: space, privacy, character, and a location within Winter Garden’s golf cart district. The existing 3 bedroom home offers nearly 1,500 square feet of living space, but step into the backyard and you quickly understand what makes this property special. This is land meant to be enjoyed. Picture evenings beneath the trees with string lights glowing overhead, friends gathered around the custom built pizza oven, dinner being prepared in the summer kitchen, music playing, and plenty of room for everyone to spread out. For the next owner, the possibilities are just as compelling as the lifestyle already here. Enjoy the property as it is, create your own private retreat, expand upon the existing outdoor spaces, or simply appreciate the increasingly rare luxury of having over an acre of land near the heart of Winter Garden. And despite the privacy, you are still connected to the lifestyle that makes this area so desirable. Being within Winter Garden’s golf cart district means trips toward Historic Downtown Winter Garden can become part of the routine. Spend Saturday mornings at the Farmers Market, enjoy dinner along Plant Street, explore local shops and restaurants, or spend an afternoon on the West Orange Trail before heading home to your own piece of Winter Garden. Homes can be renovated. Kitchens can be changed. Finishes can be replaced. But you cannot manufacture another acre of mature, established land in a location like this. That is what makes 144 Tildenville School Road different. It is not simply a home for sale. It is an opportunity to own a substantial piece of Winter Garden, with the space to enjoy today and the possibilities to make it something entirely your own tomorrow.

144 Tildenville School Road, Winter Garden

2107 Bay Line Road, Oakland
$615,000
3 Beds ⋅ 2 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code
Welcome home to Hull Island, where thoughtful upgrades, a private preserve setting, and resort-style amenities come together. Extended driveway upgraded with builder. This beautifully maintained 3-bedroom, 2-bath home backs to protected conservation land with no rear neighbors. High ceilings, electronic shades, and abundant natural light give the home an open, airy feel. The chef’s kitchen features an oversized granite island, a gas stove, pot filler, 42-inch cabinets, and additional upper cabinetry for storage. Tile backsplash, built in conventional oven and microwave. From the kitchen, you can look out over the pool while preparing meals. The spacious primary bedroom has been updated to the larger size upgrade with the builder. Master bathroom features a double vanity and a very large walk in shower with dual showerheads and a built-in bench, providing both comfort and convenience. Built in 2024, this custom fully automated SALT WATER 7FT screened-in pool area and overhead waterfall is made for relaxing and entertaining. You can control everything for the pool and waterfall , the color, the raindrops you can make it heavy or light all from the fingertips of your phone. It includes a summer kitchen with a sink and a gas fire pit that you can control with your phone. The home also offers a washer and dryer, an electric tankless water heater, and a recently installed Generac natural-gas whole-house generator designed to turn on automatically during a power outage. This home also has an irrigation system heling you keep the landscaping looking its best year- round! This home also has a water softener! The HOA is $165 per month, with no CDD. Community amenities include a resort-style pool, playground, dog park, and a boardwalk leading to a dock and fishing pier on Lake Apopka. Residents also have a private entrance to the 120-acre Oakland Nature Preserve. Downtown Winter Garden, the West Orange Trail, farmers markets, shopping, dining, golf, and pickleball are all close by. Home built in 2021 builder: M/I Homes Of Orlando LLC With its preserve views, inviting outdoor space, and convenient location, and privacy this move-in-ready home is a rare find. The photos are not virtually staged—this home truly is breathtaking! Seller has an assumable mortgage at a low interest rate of 2.375%!!!

2107 Bay Line Road, Oakland

1032 Galston Alley, Winter Garden
$1,650,000
6 Beds ⋅ 5 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Built by RCB Custom Homes as the builder’s personal residence, this exceptional 5-bedroom, 5-bath residence offers 3,506 square feet of thoughtfully designed luxury in the highly desirable Oakland Park neighborhood. Completely remodeled within the past two years, no detail was overlooked in creating a home that is as refined as it is comfortable. Beautiful new hardwood flooring, custom wood beams, designer wallpaper, upscale tile selections, custom cabinetry, premium appliances, and an antique barn wood fireplace treatment create distinctive character throughout. Custom automated blinds and a complete repaint add the finishing touches to this beautifully curated home. Designed for both everyday living and entertaining, the home features inviting screened front and side porches, with an outdoor kitchen. The premium lot faces a long green park with views of Lake Apopka, adjacent to the community clubhouse & amenities . Beyond the beautiful finishes are the exceptional behind-the-scenes upgrades that truly set this home apart, including a whole-home generator, spray foam insulation for impressive energy efficiency, an expansive climate-controlled attic offering valuable conditioned storage, and wiring in place for a future water treatment system. Enjoy all that Oakland Park has to offer, including two community pools and a prime location within the golf cart district. A complete list of upgrades and improvements is available upon request. This is a rare opportunity to own a meticulously remodeled custom residence where luxury, craftsmanship, comfort, and thoughtful design come together.

1032 Galston Alley, Winter Garden

14371 Shocklach Drive, Winter Garden
$695,000
3 Beds ⋅ 2 Baths ⋅ Latham Park North SubDv. ⋅ 34787 Zip Code
Every single day, you’ll experience the ultimate Central Florida lifestyle in your own private backyard paradise. Tucked into the coveted Latham Park community of Winter Garden, just two miles from Disney’s Magic Kingdom, this pristine 2018-built home pairs luxurious outdoor living with unbeatable convenience to world-class entertainment, shopping, and dining. Surrounded by updated curb appeal, mature landscaping, and a quiet neighborhood setting, it offers a rare combination of comfort, style, and resort-style amenities right at home. Inside, the light-filled floor plan feels crisp, elevated, and completely turn-key, highlighted by elegant crown molding and durable wood-look tile floors running throughout the main living areas. High tray ceilings accentuate the main open-concept living and dining spaces, leading seamlessly into a dedicated flex space. Showcasing true Florida indoor-outdoor living, the home features both a standard sliding door and a triple sliding glass door that opens directly from the flex space out to the pool area. At the center of it all is a modern chef’s kitchen designed for both quiet mornings and hosting friends. It boasts 42-inch cabinets, sleek quartz countertops, under-cabinet accent lighting, a gas range, and premium stainless steel appliances. Conveniently nearby, an oversized laundry room comes fully equipped with a washer and dryer while providing exceptional extra storage space. For total peace of mind and remarkable efficiency, the home is secured with a SimpliSafe security system, equipped with a tankless water heater, and features fully paid-off solar panels for ultra-low electricity bills. The primary suite serves as your private sanctuary, featuring a custom built-in walk-in closet system and a beautifully appointed primary bathroom complete with a luxurious, walk-in shower. Two additional spacious bedrooms with luxury vinyl flooring provide exceptional flexibility for family, guests, or a dedicated home office setup. Step out back into your personal outdoor oasis—a custom screen-enclosed pool deck featuring a stunning heated saltwater pool and spa, built-in controllable LED lighting overhead and within the enclosure, and a Char-Broil outdoor kitchen perfect for weekend barbecues. The fully fenced backyard ensures a private, safe space for relaxation or outdoor fun. Beyond your doorstep, enjoy Latham Park’s vibrant community events, pool, playground, and spectacular views of the Disney fireworks right from within the neighborhood—plus access to top-tier schools including Panther Lake Elementary, Hamlin Middle, Horizon High, and Windermere Prep. From private poolside relaxation to nightly magic nearby, this is a rare gem in one of Winter Garden’s most sought-after pockets.

14371 Shocklach Drive, Winter Garden

907 Celadon Street, Winter Garden
$2,495,000
6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Lake Apopka view. Protected Conservation. Detached Guest apartment. Apartment over garage. In-Law suite. Multi-generational living. EV charging station. All this perfectly describes the unique differences of 907 Celadon. The homesite is approximately 160 feet deep. A broad rear boundary of designated open space. No residential lot behind the home. The main home highlights include a massive open floor plan, oversized Chef's kitchen, first-floor primary en suite, outdoor summer kitchen, two rooms directly off the foyer offering flexibility for an executive office, or two home offices, or one room as the downstairs en suite for guests or aging family members. The nearly 41-foot screened porch, with built in summer kitchen. The Detached Guest House is 907 Sq Ft, and open studio layout, one bedroom, kitchenette, full bath. Provides flexibility as the in-law suite. Chef's Kitchen offers generous workspace for more than one cook. Kitchen-Aid ovens and built-in ice maker by Manitowoc. Expansive sliding glass doors open the great room to the green conservation and Lake Apopka views. A long back yard overlooking a deep conservation vista. The first-floor primary en suite occupies its own wing at the rear and right side of the home. A door from the kitchen closes the wing from the rest of the first floor, while the bedroom opens directly to the lanai. The bathroom features frameless shower, free standing soak tub, and dual sinks across from each other. A custom walk-in closet dressing room —with extensive built-ins, a center island and chandelier complete the wing. Upstairs, three bedrooms and an oversized loft provide the flexibility for a home theater, gaming and homework stations. Daily routines are easier here. Bright blue ockers off the mudroom keep backpacks, sports equipment, shoes and bags organized, while the large laundry room includes a specialty built-in dog wash station. Connected to the main residence by a covered breezeway, the 907 Sq ft detached guesthouse/ADU sits above a 3-car garage and includes a kitchenette, full bath and closet. The garage also includes a golf-cart bay, and EV charging station. The guest house is currently used as a private executive office. Oakland Park and Winter Garden's golf-cart approved community zones is one of the signature advantages, offering easy access to Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—just a golf cart ride from home. Direct access to the West Orange Trail offers 22 miles for walking, jogging and biking, plus community pools and green spaces.

907 Celadon Street, Winter Garden

1720 Lake Roberts Landing Drive, Winter Garden
$1,399,999
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

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