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 small-town charm with vibrant community spirit. Nestled just west of Orlando, Winter Garden is renowned for its picturesque downtown, lush parks, and an array of recreational opportunities. With its rich history dating back to the late 1800s, the city has transformed into a thriving hub that offers a delightful mix of modern amenities and historical allure.

One of the standout features of Winter Garden is its commitment to preserving the natural beauty of the area. The West Orange Trail, a scenic pathway perfect for walking, cycling, and jogging, winds through the heart of the city, providing residents with access to stunning landscapes and outdoor activities. The downtown area is alive with boutique shops, delightful eateries, and a vibrant farmers market, creating a warm community atmosphere that welcomes everyone.

When it comes to homes, Winter Garden boasts an impressive selection of Craftsman-style architecture. Characterized by their attention to detail, these homes feature wide front porches, exposed rafters, and intricate woodwork, all of which exude a sense of warmth and craftsmanship. The Craftsman style is not only aesthetically pleasing but also promotes a sense of community, with inviting spaces that encourage gatherings and connection.

In Winter Garden, you can find your dream Craftsman home that perfectly complements the enchanting lifestyle of this beautiful city. Whether you’re seeking a cozy retreat or a spacious family residence, Winter Garden offers a variety of options that cater to every taste and preference. Come experience the magic of Winter Garden, where charming homes and a vibrant community await you!

Newest Winter Garden Homes with Craftsman Architectural style

16167 Barkly Ridge Court, Winter Garden
$1,099,999
4 Beds ⋅ 3 Baths ⋅ Avalon Ridge SubDv. ⋅ 34787 Zip Code
Welcome to Avalon Ridge, one of Winter Garden’s newest and most desirable communities. This thoughtfully designed single-story home sits at the end of a private cul-de-sac on an elevated lot with beautiful lake views, offering space, functionality, and modern finishes. A welcoming foyer leads to the bright, open-concept living area, with a dedicated home office conveniently located nearby. The spacious gathering room flows into a well-appointed kitchen featuring high-end cabinetry, sleek countertops, and a large island—perfect for everyday living and entertaining. The primary suite includes an en-suite bath with dual vanities, a walk-in shower, and an oversized closet. Three additional bedrooms provide flexibility for family and guests, along with a dedicated home office. Additional features include a 3-car garage with a 240V EV charger, offering ample space for vehicles, storage, or a workspace. Enjoy exceptional privacy and stunning lake views from this elevated cul-de-sac lot. Conveniently located near major highways, theme parks, shopping, dining, and top-rated schools.

16167 Barkly Ridge Court, Winter Garden
5705 New Independence Parkway, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code
WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden
6262 Argent Wood Drive, Winter Garden
$925,000
5 Beds ⋅ 4 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code
Virtually Staged. THIS IS IT! Skip the builder and SAVE TIME and MONEY buy this practically NEW "Scarlett" floorplan by Pulte. Seller picked a premium lot (NO REAR NEIGHBOR), selected a ton of upgrades in the design center AND then after they moved in... added a gorgeous outdoor kitchen, travertine paver deck, motorized screen and LED soffit lighting and then had to relocate so their loss is your gain. This incredible floorplan features dual primary suites (one upstairs and one downstairs) plus 3 additional bedrooms and a huge loft/den. The kitchen is features upgraded level 4 quartz, built-in stainless steel oven, microwave and cooktop, soft close cabinets and a huge walk in pantry. Tons of natural light and upgrades in every room. Close to Publix, Walmart, tons of restaurants and walking distance to Hamlin Elementary AND Hamlin Middle school. Check out the virtual 360 Walkthrough link.

6262 Argent Wood Drive, Winter Garden
12934 Harvest Rain Avenue, Winter Garden
$750,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | 3 Full Baths. New Construction - February Completion! Welcome to the Ozark at 12934 Harvest Rain Avenue in Harvest at Ovation! This thoughtfully designed one-story home offers three bedrooms, three and a half bathrooms, and a private study off the foyer. The open-concept layout centers around a spacious gathering room that flows seamlessly into the dining area and gourmet kitchen with a walk-in pantry, creating the perfect space for everyday living and entertaining. The private primary suite features a spacious bathroom and large walk-in closet, while the secondary bedrooms provide comfort and flexibility for guests or hobbies. Enjoy outdoor living on the covered extended lanai and the convenience of a two-car garage with tandem storage space. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: pocket sliding glass door at great room, tray ceiling package, whole house 8' interior doors, quartz countertops, whole house blinds, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6450081

12934 Harvest Rain Avenue, Winter Garden
11079 Sound Shore Drive, Winter Garden
$825,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Welcome to your dream home that checks ALL the boxes! This 2023 built block on block construction popular Torrey floor plan has everything you will need with 5 bedrooms, 4 and a half baths, SOLAR panels included in sale price, a formal dining room, DOWNSTAIRS guest room with attached full bathroom, large lanai, bonus room to create a second living area or playroom, gourmet kitchen, and fenced in yard with no direct rear neighbor. This home is perfect for entertaining, having an open concept layout with a kitchen/living open space, while also boasting classic charm with a formal dining room off the kitchen. The stunning kitchen features a built in wall oven and microwave, cooktop with matching stainless steel hood, and large butler’s pantry. The formal dining room could be used for it’s intended purpose or it can easily be closed in with French doors to create a home office, playroom, formal sitting room, or exercise room! Upstairs you will find the remaining 4 bedrooms, 3 full bathrooms, and huge bonus room. The master retreat is true luxury with a soaking tub and fireworks view from the master bedroom! Currently, the downstairs guest room is being used as a dual purpose room with a desk to be used as an office but also has a custom, built in murphy bed that can be used when you have guests in town. This home features a huge 28x10 covered lanai perfect for dining a la fresca and enjoying the peaceful dry retention pond that this home backs up to that is fleeting with wildlife including many different bird species, hawks, and sand cranes. The spacious, fenced in yard is perfect for your furry friends or children. Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, fishing pier on the lake, biking trails, walking trails, tennis courts, pickleball, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. The clubhouse has a robust calendar of events for all ages such as Mahjong classes, exercise classes, kids dance lessons, beer tasting events, and many more! Living in the gorgeous Waterleigh community surrounded by ponds and lakes is all about nature and outdoor living! Love the outdoors but don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh has to offer! Lastly, this well loved house has all the upgrades including: solar panels (sellers will pay off the remaining loan balance at closing), telsa EV charger, motorized blinds in all 4 bedrooms upstairs, (2) alarm security systems, 3 ring cameras, 2 garage ceiling storage racks, and built in attachments in the garage for a kids ninja warrior style obstacle course. Green aspects: solar panels and reclaimed water for watering the grass.

11079 Sound Shore Drive, Winter Garden
9936 Pallida Hickory Way, Winter Garden
$468,000
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location, location, location! With a paid off solar system! Beautifully maintained home in the highly sought-after Watermark community, offering exceptional amenities and a prime location backing onto a highly rated high school, with NO rear residential neighbors. Enjoy Carpet-Free living with brand-new flooring installed in 2026, plus a lovely balcony perfect for relaxing. Your new home awaits—schedule your showing today!

9936 Pallida Hickory Way, Winter Garden
8649 Flagship Alley, Winter Garden
$495,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful one-story home located in the highly desirable Waterleigh community of Winter Garden! This charming 3-bedroom, 2-bath home offers a thoughtfully designed, open and inviting floor plan. The spacious kitchen features stone countertops, solid wood cabinetry, stainless steel appliances, a walk-in pantry, and a large center island overlooking the family room—perfect for everyday living and entertaining. The split-bedroom layout provides added privacy, while the primary suite features a walk-in closet and comfortable ensuite bath. Enjoy Florida living from the covered lanai and the added privacy of a corner lot. A two-car attached garage provides plenty of parking and storage. Waterleigh offers an exceptional resort-style lifestyle with community pools, clubhouses, fitness centers, tennis courts, playgrounds, parks, and more. Conveniently located in the sought-after Horizon West area of Winter Garden, near shopping, dining, entertainment, and Central Florida attractions. Don’t miss the opportunity to make this wonderful home yours!

8649 Flagship Alley, Winter Garden
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
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
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
Start Your Search

How much is your home worth?

Get instant property value now!