Winter Garden Homes with Craftsman Architectural style

Winter Garden Homes with Craftsman Architectural style

Welcome to Winter Garden, Florida—a charming city that beautifully blends the warmth of small-town living with the vibrancy of modern amenities. Nestled just a stone's throw from the bustling heart of Orlando, Winter Garden boasts a rich history, picturesque landscapes, and a welcoming community atmosphere. The downtown area is a delightful mix of quaint shops, delicious eateries, and local farmers' markets, all set against a backdrop of stunning historic architecture. With its lush parks, scenic lakes, and an array of outdoor recreational opportunities, Winter Garden is a haven for nature lovers and families alike.

One of the most appealing aspects of Winter Garden's real estate market is the prevalence of Craftsman-style homes. Characterized by their distinctive architectural features, these homes exude charm and character. With their low-pitched gable roofs, exposed rafters, and wide front porches, Craftsman homes invite you to relax and enjoy the beauty of your surroundings. Inside, you'll find spacious layouts filled with natural light, built-in shelving, and handcrafted woodwork, all of which reflect the artistry and attention to detail that define this architectural style.

Whether you’re looking for a cozy family home or a tranquil retreat, Winter Garden’s Craftsman homes provide the perfect blend of comfort and style. Experience the warmth of this enchanting city and discover why Winter Garden is not just a place to live, but a place to call home. Embrace the charm and character of Craftsman architecture, and let Winter Garden welcome you with open arms.

Newest Winter Garden Homes with Craftsman Architectural style

17602 Japonica Bloom Drive, Winter Garden
$785,000
5 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Luxury new construction home near Walt Disney World theme parks! The spacious 5 bedroom, 4 bathroom design offers the perfect combination of style, functionality, and comfort. The home features a 3-car tandem garage, a covered front porch and a covered backyard lanai, ideal for outdoor relaxation or entertaining. The heart of the home is the chef-inspired gourmet kitchen, which includes solid surface countertops, an island, and high-end stainless steel appliances, such as a cooktop, range hood, built-in oven and microwave, and dishwasher. The spacious living area is designed with upgraded flooring and enhanced with natural light flowing in through dual-pane energy-efficient windows. Sliding glass doors allow access to the covered backyard patio, seamlessly blending indoor and outdoor living spaces. The private primary suite is a true retreat, featuring an extended sitting room off of the bedroom. The primary bathroom features a dual sink vanity with Delta faucets, ceramic tile flooring, a luxurious shower with a glass enclosure and a freestanding bathtub. Additional features include an upgraded lighting package, towel bars, and a huge walk-in closet, offering plenty of storage and comfort. The secondary bedrooms are generously sized, with each second floor bedroom surrounding a spacious loft. Additional features of this exceptional new home include a full sprinkler system, a complete landscaping package, energy-efficient construction, garage door openers, and a utility area with ceramic tile flooring. The home also boasts all 8' doors on the first floor, pre-plumb for a laundry sink, fully upgraded design finishes, including Revwood flooring, and a new home warranty for peace of mind. Call today to schedule a tour!

17602 Japonica Bloom Drive, Winter Garden
1021 Huntspoint Street, Winter Garden
$865,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to exceptional living in OAKLAND PARK, a Parade of Homes-winning community, where thoughtful design, extensive upgrades (~145K), & modern conveniences come together in this beautifully enhanced home. This FENCED home features 4 bedrooms, 3 en-suite baths, a remodeled half bath, dining space, loft, a screened-in balcony, TILE flooring, & a newer AC (2024), offering an ideal layout for everyday living & entertaining. The downstairs room is especially impressive, enhanced with stunning doors that beautifully frame the space, a Murphy bed with built-in storage, & its own private patio—perfect for guests, multigenerational living, or home office. The thoughtfully designed kitchen is both stylish & highly functional, with all kitchen appliances updated within the last few years with the exception of the cooktop & hood. Kitchen features a Bosch dishwasher, LG ThinQ refrigerator, built-in oven & microwave, QUARTZ counters, tile backsplash, a water filtration system, and an enhanced island customized with wood trim. Adjacent to the kitchen, you'll find two pantries, a built-in desk, & additional storage beneath the staircase. An electric FIREPLACE accented by custom shiplap creates a warm & inviting focal point in the living area. Custom walls add character & sophistication, including a striking board & batten design in the primary bedroom, a shiplap wall in the spare bedroom, & a custom wall along the staircase. PLANTATION SHUTTERS & updated lighting add both style & functionality. Custom closet systems are featured in all three bedrooms, along with two linen closets, the pantry, & the closet opposite the pantry. Additional cabinetry has been added to the laundry room, complete with a convenient drying rack. The upstairs bedrooms each feature their own en-suite bath, providing privacy & convenience, while one bedroom enjoys access to a screened-in balcony. The garage is a standout feature of its own, offering a dedicated mini-split AC, EV charger, epoxy flooring, abundant storage, & overhead storage that lowers for easy access. The house & garage are connected by a covered walkway, a rarity to the neighborhood. A truly exceptional bonus is the premium SOLAR & whole-home battery backup system (installed 2024), representing an 86K investment that will be PAID OFF at CLOSING. The 12.64 kW system includes 32 Mission Solar panels & four Enphase IQ Battery 5P units, providing approximately 20 kWh of battery storage. The system is designed to provide substantial backup power during outages & can keep virtually the entire home powered under normal household use. Enjoy a low monthly energy bill of ~$35! Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart friendly WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the area's most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

1021 Huntspoint Street, Winter Garden
206 N Highland Avenue, Winter Garden
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.

206 N Highland Avenue, Winter Garden
11397 Bourbon Rose Circle, Winter Garden
$840,000
4 Beds ⋅ 4 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Covered Lanai | 3-Car Garage. New Construction - November Completion! Welcome to the Bainbridge at 11397 Bourbon Rose Circle in Esplanade at McKinnon! This thoughtfully designed single-story home offers four bedrooms, three-and-a-half bathrooms, a dedicated study, and a spacious open-concept layout. At the heart of the home, the gourmet kitchen features a large island overlooking the dining area and great room, creating the perfect space for entertaining. The private primary suite is tucked away at the rear of the home and includes a spa-inspired bathroom and expansive walk-in closet. Two secondary bedrooms share a bath near the front of the home, while a private bedroom suite offers added flexibility for guests. Elegant tray ceilings, crown molding, and 8-foot interior doors enhance the home's appeal, while the covered lanai extends the living space outdoors. Additional Highlights Include: powder bath in place of storage. Photos are for representative purposes only. MLS#O6444985 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11397 Bourbon Rose Circle, Winter Garden
14371 Shocklach Drive, Winter Garden
$700,000
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
910 Trowman Aly, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the Executive kitchen features custom cabinetry with updated hardware, quartz countertops, an island, a gas range, vent hood, tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. The upstairs has a lofty feel has a nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
128 N Highland Avenue, Winter Garden
$965,000
4 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

128 N Highland Avenue, Winter Garden
4817 Fair Winds Court, Winter Garden
$1,200,000
5 Beds ⋅ 5 Baths ⋅ Ests/Lakeview Preserve SubDv. ⋅ 34787 Zip Code
This is a rare opportunity to find a popular Roseland floorplan loaded with upgrades, perfectly located on a quiet cul-de-sac on a private lot with no rear neighbors and extra space on this oversized lot! Best of all, you can enjoy picturesque views of Johns Lake right from the front yard! Inside, you are greeted with a beautiful double glass door entry, soaring dramatic ceilings, and elevated light fixtures that create an immediate sense of openness and grandeur. Luxury vinyl plank floors throughout bring warmth to the home. To the right, you have an oversized flex room with French doors, making a perfect home office, play area, or home gym. The formal dining room provides a great space to gather around meals for family nights or holiday hosting. The butler's pantry features a wine fridge and added cabinets, while the walk-in pantry is truly impressive with built-in shelving. The kitchen is truly the heart of the home, featuring stunning quartz countertops, cream cabinets, upgraded lighting, and a beautiful tile backsplash. Transom windows in the backsplash pour natural light into the kitchen. The open breakfast area is perfect for enjoying quick meals with the family and overlooks the great room, which has custom accent walls and an elevated light fixture to enhance the space. Triple windows above brighten the room, & the 12ft slider door overlooks the extended lanai and huge flat yard—with plenty of space to add a pool and outdoor kitchen! Downstairs features a massive guest suite that can serve as a second master bedroom, complete with its own ensuite bath, upgraded shower, and large walk-in closet—perfect for in-laws or guests to have their own retreat! There is also another full-sized bath downstairs with a shower and a door leading out to the lanai for quick access from the future pool area. Heading upstairs, there are 4 additional bedrooms, 3 full baths, and the laundry room. Elegant open railings bring added character across the catwalk over the living room. Directly at the top of the stairs, French doors lead to your primary retreat. You are greeted by a sitting area with a large window and a massive primary suite with a tray ceiling and picturesque windows looking over the yard and trees beyond. To the left is your stunning ensuite bathroom with split vanities, lots of natural light, a soaking tub, a large walk-in shower with a bench, and dual closets (one with built-ins). The other three oversized bedrooms add similar quality, each with direct ensuite access to a bathroom (including two sharing a Jack-and-Jill bath). The laundry room features built-in cabinets and two washer/dryer sets side by side, allowing you to handle two loads at a time—perfect for large or busy families! Over in the garage, vehicle enthusiasts and storage seekers will marvel at the pristine three-car garage, complete with sleek epoxy flooring, heavy-duty overhead storage racks, and a private car wash station for ultimate convenience. The exclusive gated community offers resort-style amenities including a clubhouse, swimming pool, splash pad, and playground—all with a low HOA fee and no CDD. The community is perfectly located on the border of Clermont and Winter Garden, offering access to all both cities have to offer! You are just 15 minutes from Winter Garden Village for shopping, dining, and SR-429 access into Orlando, and within 20 minutes from both downtown Clermont and downtown Winter Garden. Come tour this stunning property today!

4817 Fair Winds Court, Winter Garden
17425 Water Hemlock Road, Winter Garden
$789,990
4 Beds ⋅ 3 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home at Lake Star At Ovation in Winter Garden, FL. Built by M/I Homes, this 2-story home offers 2,753 square feet of thoughtfully designed living space with 4 bedrooms and 3 bathrooms. Step inside to discover an open-concept living space that creates a seamless flow between the main gathering areas, perfect for everyday living and entertaining. The quality of design is evident throughout, with carefully selected finishes and a well-planned floorplan that maximizes both comfort and functionality. The owner's bedroom features a spa-inspired en-suite bathroom and a large walk-in closet, providing a relaxing retreat at the end of each day. 3 additional bedrooms offer generous space for family, guests, or a home office. The spacious loft open to below and makes a great secondary family room or gaming area. A covered lanai extends your living area outdoors, ideal for enjoying Florida's beautiful weather year-round. This home is situated within a well-established neighborhood with convenient proximity to parks and recreational areas, making it an ideal setting for active lifestyles and families. The neighborhood offers a welcoming atmosphere with access to green spaces where residents can enjoy the outdoors.

17425 Water Hemlock Road, Winter Garden
17431 Water Hemlock Road, Winter Garden
$769,990
4 Beds ⋅ 3 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home located at Lake Star At Ovation in Winter Garden, FL. Built by M/I Homes, this 2-story home offers 2,343 square feet of thoughtfully designed living space with 4 bedrooms and 3 bathrooms. Step inside to discover an open-concept living space that creates a seamless flow between the main gathering areas, perfect for everyday living and entertaining. The quality of design is evident throughout, with carefully selected finishes and attention to detail in every room. The owner's bedroom features a spa-inspired en-suite bathroom and two walk-in closets, providing a comfortable retreat at the end of each day. Additional features include a large kitchen island, a massive bonus room upstairs, a private lanai for outdoor enjoyment, a wrap-around front porch, and a 2-car garage. This home delivers a well-crafted layout with quality construction and a functional design that suits a variety of lifestyles. Situated within the desirable Lake Star At Ovation neighborhood, this new home is conveniently nearby parks and outdoor recreation areas

17431 Water Hemlock Road, Winter Garden
17937 Lake Star Road, Winter Garden
$859,990
4 Beds ⋅ 4 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home by M/I Homes, located at Lake Star At Ovation in Winter Garden, Florida. This 2-story home offers 3,032 square feet of thoughtfully designed living space, featuring 4 bedrooms, 3 full bathrooms, and 1 half bathroom. Step inside to discover an open-concept living space that creates a seamless flow throughout the main level, perfect for everyday living and entertaining. The quality of design is evident in every detail, from the well-appointed finishes to the functional layout that maximizes both comfort and style. The owner's bedroom features a private en-suite bathroom and a large walk-in closet, providing a relaxing retreat at the end of the day. The additional 3 bedrooms, as well as the huge upstairs loft, offer generous space for family, guests, or a home office. Enjoy Florida's outdoor lifestyle on the inviting lanai, ideal for relaxing or hosting gatherings in a comfortable setting. This move-in ready home delivers a well-balanced combination of space, design, and comfort in one of Winter Garden's desirable neighborhoods.

17937 Lake Star Road, Winter Garden
13112 Dendy Way, Winter Garden
$825,000
5 Beds ⋅ 4 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code
Welcome to luxury living in the heart of Horizon West! This stunning Santa Fe floorplan by K. Hovnanian Homes perfectly blends rustic charm with modern elegance, offering space, privacy, and an unbeatable location. Step inside to a bright, airy main living space featuring dramatic vaulted ceilings accented by rich wooden beams and seamless, carpet-free flooring—sleek tile flows throughout the main level, while high-end Luxury Vinyl Plank (LVP) spans the second floor. A designer farmhouse aesthetic carries through the gourmet kitchen and bathrooms, blending timeless style with everyday functionality. The main floor features a peaceful primary suite with a spa-like ensuite bath complete with a standalone soaker tub and separate shower, as well as a massive second guest bedroom with a stylish barn door entrance that works perfectly as a private suite or home office. Upstairs, a spacious loft offers a flexible secondary living area alongside three generously sized bedrooms and two full bathrooms. Outside, the covered lanai overlooks a peaceful, open grassy field, delivering ultimate backyard privacy with no rear neighbors. Positioned just down the street from the shopping, dining, and entertainment of Flamingo Crossings, minutes from Walt Disney World, and within walking distance to the brand-new Ovation Elementary School right outside the neighborhood, this home offers the ideal combination of high-end design, privacy, and everyday convenience. Schedule your private tour today!

13112 Dendy Way, Winter Garden
Start Your Search