Winter Garden Homes with Craftsman Architectural style

Winter Garden Homes with Craftsman Architectural style

Welcome to Winter Garden, Florida – a charming city that perfectly blends the warmth of small-town living with the vibrancy of modern amenities. Nestled just a short drive from the bustling attractions of Orlando, Winter Garden boasts a rich history, picturesque landscapes, and a tight-knit community that invites you to call it home. With its quaint downtown district, complete with delightful boutiques, farm-to-table restaurants, and scenic parks, Winter Garden offers a lifestyle that feels both inviting and invigorating.

One of the standout features of this enchanting city is its stunning collection of homes, particularly those designed in the Craftsman architectural style. Known for their distinctive charm, Craftsman homes are characterized by low-pitched roofs, wide eaves, exposed rafters, and beautiful woodwork. These residences exude an artisanal quality that reflects a commitment to craftsmanship and detail, making them a perfect fit for the artistic spirit of Winter Garden.

Living in a Craftsman home in Winter Garden means enjoying spacious, open floor plans that seamlessly blend indoor and outdoor living. Many of these homes feature inviting porches, perfect for sipping coffee while soaking in the serene surroundings. The rich wood finishes and built-in features create a warm atmosphere that makes every space feel like home.

Whether you’re exploring the local farmers market, taking a stroll along the West Orange Trail, or enjoying a sunset at Lake Apopka, Winter Garden offers a lifestyle that celebrates community, nature, and the beauty of well-crafted homes. Discover your dream Craftsman home in this idyllic city and embrace a life filled with warmth and charm.

Newest Winter Garden Homes with Craftsman Architectural style

$1,100,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom built in closets, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! 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, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. 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 provides!

10043 Little Alcove Loop, Winter Garden
$482,000
3 Beds ⋅ 2 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought-after Waterside at Johns Lake community in Winter Garden! This spacious, light-filled home features a desirable open-concept floor plan designed for both everyday living and entertaining. The gourmet kitchen offers abundant cabinetry, generous counter space, and **double ovens**, flowing seamlessly into the dining and living areas. The spacious primary suite is a true retreat, complete with a spa-like ensuite bath and a **custom walk-in closet with built-in organization**. Generously sized secondary bedrooms provide flexibility for family, guests, or a home office. Enjoy Florida living year-round from the **screened-in lanai**, overlooking the private backyard—perfect for relaxing or hosting gatherings. Additional upgrades include **gutters**, **decorative exterior shutters**, and thoughtful finishes throughout. Waterside at Johns Lake offers exceptional resort-style amenities including a community pool, clubhouse, fitness center, playground, and scenic walking trails. Ideally located just minutes from Historic Downtown Winter Garden, Hamlin Town Center, SR 429, the Florida Turnpike, shopping, dining, entertainment, and top-rated schools. This move-in-ready home combines modern comfort, quality upgrades, and an unbeatable location. Schedule your private showing today!

16954 Tradewind Point, Winter Garden
$833,771
5 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Corner Lot | Game Room | Dedicated Study. New Construction - December Completion! Welcome to the Cumberland at 15993 Honey Harvest Street in Harvest at Ovation! Discover a thoughtfully designed home where style and functionality come together. The welcoming foyer leads into an open-concept living space featuring a spacious great room, dining area, and gourmet kitchen, creating the perfect setting for everyday living and entertaining. Pocket sliding glass doors in the great room open to an expansive covered lanai, blending indoor and outdoor living. Privately situated just off the dining area and kitchen, the primary suite offers a spacious bathroom with dual sink vanities, an oversized shower, and a walk-in closet. At the front of the home, you'll find a secondary bedroom, a full bathroom, and a convenient half bathroom. Upstairs, three additional bedrooms, two full bathrooms, and a versatile game room provide plenty of space for relaxation and recreation. 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: study, tray ceiling package, a shower in bathroom 3, pocket sliding glass door, 8' interior doors, laundry room sink, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6431045

15993 Honey Harvest Street, Winter Garden
$812,285
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Corner Lot | Dedicated Study | Oversized Garage | Gourmet Kitchen. New Construction – December Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Clair at 12940 Harvest Rain Avenue in Harvest at Ovation! This spacious single-story home offers a thoughtfully designed open-concept layout centered around an impressive great room that flows seamlessly into the dining area and gourmet kitchen with a large island. The private primary suite features a luxurious bathroom and generous walk-in closet. Three secondary bedrooms, a dedicated study, and multiple full bathrooms provide flexibility for work, guests, or hobbies. Direct access to the laundry area through the convenient drop zone just off the two-car garage provides added convenience. Enjoy indoor-outdoor living with the expansive lanai, perfect for relaxing or entertaining. 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: Tray ceiling package, whole house 8' interior doors, study in place of flex, deluxe primary bathroom, outdoor kitchen rough-in, cushion close doors and drawers kitchen cabinet package, and whole house blinds. Photos are for representative purposes only. MLS#O6430978

12940 Harvest Rain Avenue, Winter Garden
$1,495,000
4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code
Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Crooked Can Brewery, Plant Street Market, The Garden Theater & the West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Refined outdoor living abounds on the back porch with a custom summer kitchen. Just a short golf cart ride to Pickle Ball at Veterans, Splash Pad on Plant, a swim at Farnsworth Pool or exploring nature at Newton Park. Don't miss this one-of-a-kind opportunity!

412 N Boyd Street, Winter Garden
$685,000
4 Beds ⋅ 3 Baths ⋅ Latham Park South SubDv. ⋅ 34787 Zip Code
Every single night, you'll have a front-row seat to the magic. Tucked into the coveted Latham Park community of Winter Garden, your new home will be just two miles from Disney's Magic Kingdom! This pristine 2020-built home pairs peaceful waterfront living with an unbeatable, nightly display of Disney’s fireworks right from your welcoming front porch and front yard. Surrounded by updated curb appeal, fresh front landscaping, and a quiet neighborhood setting, it offers a rare lifestyle that truly captures the best of Central Florida living. Inside, the light-filled 2,214-square-foot floor plan feels crisp, elevated, and completely turn-key with brand-new interior paint, custom window shades, and stylish updated lighting throughout. High tray ceilings elevate the main open-concept living and dining spaces, accentuating the clean lines and durable luxury vinyl flooring. At the center of it all is a modern chef’s kitchen designed for both quiet mornings and hosting friends. It features sleek quartz countertops, upgraded over- and under-cabinet accent lighting, a brand-new dishwasher, and an effortless flow into the living area. Conveniently nearby, a dedicated laundry space comes equipped with a brand-new washer and dryer. The primary suite serves as your private sanctuary, complete with a custom built-in walk-in closet system for ultimate organization and peaceful views. Three additional spacious bedrooms and pristine full bathrooms provide exceptional flexibility for guests, family, or a dedicated home office setup. Even the two-car garage has been thoughtfully upgraded with durable epoxy flooring and a full wall mirror, ready to function as your ideal home gym. Step out back to your fully screened-in patio, the perfect bug-free haven for relaxing with a cool drink while taking in serene views of the pond. The leveled backyard is fully enclosed with a metal fence and framed by dense privacy hedges, giving you a private, safe space for pets or outdoor fun. Beyond your doorstep, enjoy a vibrant community complete with active pool events, playground amenities, and access to top-tier local schools including Panther Lake Elementary, Hamlin Middle, Horizon High, and Windermere Prep right around the corner. From peaceful water views out back to fireworks lighting up the sky out front, this is a rare gem in one of Winter Garden’s most sought-after pockets.

9202 Merlon Drive, Winter Garden
$945,000
4 Beds ⋅ 4 Baths ⋅ Oxford Chase SubDv. ⋅ 34787 Zip Code
Welcome to 14897 Ellingsworth Lane – A Spacious Retreat in Gated Oxford Chase Tucked away on a quiet cul-de-sac in the sought-after gated community of Oxford Chase, this stunning 4-bedroom, 3 1/2-bathroom home with a flex space ideal for a home office offers the perfect balance of elegance, function, and location. Built in 2018, the home features an open-concept layout, soaring ceilings, and a long list of upgrades designed for today’s modern lifestyle. From the moment you arrive, you’ll be drawn in by the lush landscaping, paver driveway, and welcoming covered front porch. Inside, enjoy dramatic two-story ceilings, abundant natural light, and designer fixtures—including crystal and chrome chandeliers in both the formal dining room and the second dining area off the kitchen. At the heart of the home, the spacious kitchen boasts shaker cabinetry, quartz countertops, a large island, walk-in pantry, stylish backsplash, natural gas stove, and stainless-steel appliances—all opening to the generous family room, perfect for entertaining or relaxing. The thoughtfully designed split floor plan features a serene primary suite on one side of the home, complete with a spacious bedroom, his-and-her walk-in closets, and a spa-like en-suite bath with dual vanities, soaking tub, and walk-in shower. A second en-suite bedroom on the opposite wing offers privacy for guests, in-laws or multigenerational living. Two additional downstairs bedrooms provide versatility, and one of them is currently used as a home office. Both larger bedrooms feature walk-in closets, while the stylish powder room adds convenience near the main living areas. Upstairs, a large open loft provides flexible space for a TV room, homework area, or playroom, alongside two more bedrooms—one with new carpet, the other with luxury vinyl plank flooring—and a full bath. Additional features include: Three-car garage (2-car plus separate 1-car currently used as a gym) Tile flooring throughout the main living areas Wide luxury vinyl plank flooring in most bedrooms Ceiling fans throughout Laundry room on the first floor with both gas and electric dryer hook-ups Optional water softening system Security system, window blinds, and natural gas connection Expansive backyard ready for outdoor entertaining Community playground and dog park The location is unbeatable— very close to A-rated Sun Ridge Elementary and Sun Ridge Middle School, so you’ll never sit in car lines again! You’re also just minutes from Tucker Ranch, Winter Garden Village, historic Downtown Winter Garden, and Oakland, with easy access to Avalon Road and major highways. With its prime location, spacious layout, and luxury finishes, this home truly has it all. Don’t miss the opportunity to make 14897 Ellingsworth Lane your next address.

14897 Ellingsworth Lane, Winter Garden
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Lake Apopka Sound Ph 1 SubDv. ⋅ 34787 Zip Code
Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, and calming bird watching right from the backyard. Highlights of this home from outside to inside are wide paver driveway with parking pad, spacious 3 car garage, covered front and rear porches, fully fenced in backyard, extended rear concrete patio, large flex room, mother in law suite with private entrance and kitchenette, and incredible kitchen to love at the center of an open floorplan. Floorplan: Triple split layout puts the primary suite, the secondary bedrooms, and the mother in law suite each in their own private area of the home. The mother in law suite has its own private exterior entrance, kitchenette, bedroom, and full bath. Large flex room for a home gym, office, studio, gaming room, or playroom. Kitchen: Cabinets to the ceiling, stone counters, beveled subway tile, farmhouse sink, island with seating for four, built-in wall oven and microwave, stainless vented hood, pot filler above the cooktop, spacious pantry, open to the living and dining space. Interior: Tray ceilings in the dining room, living room, and primary suite, wood slat accent wall, crown molding, upgraded lighting, ceiling fans, window treatments installed. Primary suite with walk in closet, corner tub, double sinks, and glass shower. Ceramic tile in main living areas, carpet in secondary bedrooms, inside laundry room. Exterior: Wide paver driveway with large paved parking pad, spacious three car garage, covered front porch, covered rear porch, extended full width concrete patio, fully fenced backyard with gates on both sides, sprinkler system throughout, tile roof. Recreation: Killarney Station trailhead five minutes out with bike rentals, repairs, and supplies center. West Orange Trail runs 20 plus miles into historic downtown Winter Garden. Lake Apopka Wildlife Drive and Lake Louisa State Park both an easy drive. Convenience: Downtown Wintergarden 25 minutes, Costco 8 minutes, Disney 25 minutes, Downtown Orlando 30 minutes, MCO Airport 35 minutes.

17854 Hither Hills Circle, Winter Garden
$495,000
3 Beds ⋅ 2 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden
$859,900
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden
$575,000
4 Beds ⋅ 2 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Privacy is a rare find in the highly sought-after Hamlin area of Winter Garden, and this move-in ready 4-bedroom, 2-bath home delivers just that. With no rear neighbors and only one adjacent neighbor, you'll enjoy peaceful sunset views from the fully fenced backyard while being just minutes from Hamlin Town Center, Horizon West, top-rated schools, SR 429, shopping, dining, and Walt Disney World Resort.Inside, luxury vinyl plank flooring flows throughout the home, complemented by custom plantation shutters, recessed lighting, and an elegant tray ceiling in the Owner's Suite that adds warmth and architectural character. The well-appointed kitchen is designed for everyday living and effortless entertaining, featuring quartz countertops, a gas range, stainless steel appliances, a tile backsplash, and a reverse osmosis drinking water system. Additional upgrades include double-pane Low-E windows and sliding glass doors, a tankless water heater, and a programmable smart irrigation system for added comfort, efficiency, and convenience.Designed for year-round Florida living, the inviting front porch, covered lanai, and fully fenced backyard provide the perfect setting to entertain guests, relax with family, or simply unwind while taking in breathtaking Florida sunsets. With no rear neighbors, you'll appreciate the added sense of privacy that's becoming increasingly difficult to find in Horizon West.Ideally located in the heart of Hamlin and Horizon West, you'll be minutes from Hamlin Town Center, Publix, local restaurants, boutique shopping, Cinépolis Luxury Cinemas, Orange County National Golf Center, scenic parks and trails, Winter Garden Village, Historic Downtown Winter Garden, Flamingo Crossings, Walt Disney World Resort, and major commuter routes including SR 429.Offering an exceptional combination of privacy, modern upgrades, energy-efficient features, and one of Central Florida's most desirable locations, this Winter Garden home truly captures the best of Florida living. Schedule your private showing today and experience everything this exceptional property has to offer.

15395 Sugar Citrus Drive, Winter Garden
$559,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3bcd SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the master-planned community of Waterleigh community of Horizon West in Winter Garden. This popular Bellake floor plan offers over 2,200 square feet of beautifully maintained living space. Rare concrete block construction on both the first and second floors, thoughtful updates by the current owner, and a functional open-concept layout make this home stand out from the moment you arrive. As you step inside, you're welcomed by a versatile flex room to the left, perfect for a home office, playroom, or formal sitting area, while the updated half bath with a new vanity and light fixture is conveniently located to the right. Continue into the spacious great room that flows seamlessly into the kitchen, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel Whirlpool appliances, granite countertops, a large center island with additional cabinet storage, ample cabinetry, a dedicated dining area, and overlooks the main living space. Select areas of fresh interior paint, refreshed tile flooring, updated lighting, and a new ceiling fan add to the home's clean, well-cared-for feel. Just beyond the kitchen, a mudroom provides access to the attached two-car garage. Additional storage can be found beneath the staircase. Upstairs you'll find all three bedrooms, two full bathrooms, the laundry room, and an additional storage closet. The spacious primary suite features a beautifully remodeled en-suite bathroom with a walk-in shower finished in timeless subway tile, contrasting dark grout, sleek matte black fixtures, and a custom-designed walk-in closet. The secondary bedrooms share a full bathroom with a dual-sink vanity. Sliding glass doors off the great room open to the covered, screened lanai with paver flooring overlooking the side and backyard. The security system, security cameras, washer, and dryer all convey. Enjoy Waterleigh's resort-style amenities including four pools, four parks, two fitness centers, tennis courts, beach volleyball, putt-putt golf, walking trails, a fishing pier, and a beautiful clubhouse, while the HOA maintains the lawn and shrubs. Minutes from Hamlin Town Center, Publix, SR 429, Disney, and the shores of Hickory Nut Lake, you'll even enjoy Disney fireworks from your driveway. Schedule your private showing today!

15741 Fountain Springs Road, Winter Garden
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