Winter Garden/Oakland Homes with Craftsman Architectural style

Winter Garden/Oakland Homes with Craftsman Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a hidden gem nestled just a stone's throw away from the vibrant city of Orlando. Known for its picturesque landscapes and charming downtown, this area blends small-town warmth with modern conveniences, making it an ideal place to call home.

Winter Garden, with its rich history and thriving community, boasts a delightful array of shops, restaurants, and parks. The historic downtown area is a focal point, featuring a beautifully restored theater and a bustling farmer's market that draws locals and visitors alike. Just a short drive away, Oakland offers a serene escape with its scenic trails and lush greenery, perfect for nature enthusiasts and families seeking outdoor adventures.

One of the standout features of homes in this region is their stunning Craftsman architectural style. Characterized by their attention to detail, these homes often showcase exposed beams, wide front porches, and intricate woodwork that exudes warmth and character. The Craftsman style is not just about aesthetics; it embodies a philosophy of craftsmanship and simplicity, creating inviting spaces that feel like home. Many of these residences are nestled in tree-lined neighborhoods, allowing for a tranquil lifestyle while still being close to the vibrant amenities of Winter Garden and Oakland.

Whether you're drawn to the historic charm of Winter Garden or the serene beauty of Oakland, the Craftsman homes in this region offer a unique opportunity to experience Florida living at its finest. Discover your dream home in this captivating area, where comfort meets community in perfect harmony.

Newest Winter Garden/Oakland Homes with Craftsman Architectural style

$560,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenity | Flat Lot | Dedicated Home Office | Low HOA Dues. New Construction - November Completion! Welcome to the Ashwood at 14751 Field Daisy Drive in Harvest at Ovation! This thoughtfully designed three-story home offers flexible living with a private study near the entry, an open-concept great room, and a spacious kitchen with a large island that keeps everyone connected. Upstairs, the inviting primary suite provides a peaceful retreat, while two secondary bedrooms and a convenient laundry room add everyday comfort. The third-floor game room with a full bath creates the perfect space for entertaining, hobbies, or overnight guests. A covered lanai and charming front porch extend your living space outdoors, and the two-car garage provides plenty of room for storage and convenience. 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: French doors at study and quartz countertops at kitchen. Photos are for representative purposes only. MLS#O6436927

14751 Field Daisy Drive, Winter Garden
$530,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Flat Lot | 3 Full Baths | Bonus Room. New Construction – November Completion! Welcome to the Ashwood at 16050 Honey Harvest Street in Harvest at Ovation! This warm and inviting two-story home blends comfort, flexibility, and effortless everyday living. A charming front porch opens to a bright foyer with a private study, while the heart of the home features a spacious great room that flows into the beautifully designed kitchen with a large island, walk-in pantry, and inviting lanai for indoor-outdoor gatherings. Upstairs, the serene primary suite offers a relaxing retreat with a spa-inspired bath and generous walk-in closet, while two secondary bedrooms share a full bath. The top-floor game room with its own bath provides the perfect space for entertaining, hobbies, or cozy evenings at home. Thoughtfully designed and filled with natural flow, this home is made for connection and comfort. 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: Wet bar at game room, game room with full bath above garage, covered extended lanai, pre-plumb for future laundry tub, and whole house blinds. Photos are for representative purposes only. MLS#O6436917

16050 Honey Harvest Street, Winter Garden
$834,000
5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Luxury new home 3501 SFT with oversized yard near Walt Disney World theme parks. Frost plan by RockWell Homes, a luxurious new home designed to meet all your needs. This stunning home features 5 bedrooms, 4.5 bathrooms, and a spacious layout that includes both a primary suite and a guest bedroom on the first floor, making it ideal for multi-generational living or hosting visitors. The Frost plan also boasts an oversized covered front patio, 12-foot sliding glass back door, 8-foot front door, and a covered backyard lani for seamless indoor-outdoor living. Step into the heart of the home, where the chef-inspired kitchen features a large eat-in island, stainless steel appliances, including a cooktop, oven, microwave, and dishwasher, and an undermount sink with a Delta faucet. The kitchen is further enhanced with a ceramic tile backsplash, upgraded 42-inch cabinets, abundant solid surface countertop space, and a huge walk-in pantry, offering both style and practicality for meal preparation and storage. The upgraded flooring and lighting package throughout the home complete the modern, elegant aesthetic. The luxurious primary suite is located on the first floor for ultimate convenience and privacy. It includes a dual-sink vanity with solid surface countertops and Delta faucets, a ceramic tile shower with a glass enclosure, ceramic tile flooring, and a lighting package. A spacious walk-in closet and towel bars add to the functionality and style of this retreat. Also located on the first floor, the secondary suite offers a full bath with ceramic tile flooring, a ceramic tile tub/shower surround, Delta faucets, a lighting package, and towel bars, ensuring comfort and convenience for guests or family members. Upstairs, you’ll find three additional secondary bedrooms, each with generous closet space and access to two additional bathrooms, which feature ceramic tile flooring, Delta faucets, lighting packages, and towel bars. The Frost plan also includes a gameroom, perfect for family entertainment or as a versatile space for play, work, or relaxation. The home is designed with energy-efficient block construction and dual-pane energy-efficient windows, keeping your energy costs down while ensuring comfort throughout the year. Additional features of this new home include a full landscaping package, a full sprinkler system, full gutters, a garage door opener, covered back yard lanai, upgraded flooring throughout, and a 10-year structural new home warranty for added peace of mind. With its spacious layout, luxurious finishes, and modern amenities, the Frost plan by RockWell Homes is the perfect choice for those seeking both elegance and functionality in their next home.

17428 Honeybell Tangelo Court, Winter Garden
$758,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this stunning 3-bedroom, 3-full-bathroom residence boasting 2,976 square feet of beautifully designed living space, plus a dedicated office, spacious loft, and versatile bonus room. Perfectly positioned on a premium lakeview homesite, this exceptional property offers tranquil water views and the spectacular bonus of enjoying Disney fireworks from your own backyard. Step outside into your private backyard oasis, where a sparkling pool creates the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. The fully fenced backyard provides both privacy and space, while the premium lot offers a picturesque backdrop that truly sets this home apart. Inside, the home is thoughtfully appointed with upscale details throughout. The gourmet-inspired kitchen features 42-inch cabinetry, complemented by upgraded light fixtures and designer-style ceiling fans throughout the home. The spacious bonus room, enclosed by elegant frosted-glass doors, offers a flexible space ideal for a media room, home office, entertaining, or additional living space. The dedicated office and generous loft provide even more versatility for today’s lifestyle. Additional highlights include a 2024 A/C, 2025 water heater, and an impressive 25-foot extended garage offering exceptional storage and flexibility for vehicles, recreational equipment, or hobbies. Adding to the ease of Florida living, the HOA includes landscaping and hedge trimming, allowing you to spend more time enjoying your home and less time maintaining it. From the premium lakefront setting and private pool oasis to the thoughtful upgrades, expansive floor plan, and unforgettable Disney fireworks views, this is a home that delivers an exceptional blend of luxury, comfort, and lifestyle.

14735 Snowy Egret Street, Winter Garden
$965,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home! BUYER INCENTIVE! Seller is offering $10,000 toward the buyer’s closing costs! Take advantage of this incredible opportunity to reduce your out-of-pocket expenses and make owning this beautiful Winter Garden home even more attainable.

9566 Bolero Road, 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
$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 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
Your private Florida retreat awaits in the highly sought-after Waterleigh community of Winter Garden! This beautifully upgraded and move-in-ready D.R. Horton Cresswell offers the perfect combination of style, comfortable living and exceptional outdoor entertaining. From the moment you arrive, thoughtful upgrades and elevated finishes set this home apart. Inside, laminate flooring flows throughout the main living areas, creating a seamless and modern feel. A dramatic geometric accent wall adds designer character to the loft and staircase, while the spacious primary suite has been transformed into a luxurious retreat featuring a fully customized walk-in closet and beautifully renovated en-suite bathroom. The guest bathroom has also been tastefully updated with contemporary finishes. Then step outside—and discover where this home truly shines. Your private backyard oasis is designed for Florida living and effortless entertaining, featuring a sparkling pool and spa, fully equipped outdoor kitchen and built-in Bluetooth speakers. Whether you're hosting friends, enjoying a weekend pool day or unwinding after a long day, this outdoor space feels like your own private resort. Privacy landscaping and low-maintenance artificial turf create a secluded setting, while permanent exterior lighting adds beautiful ambiance and curb appeal day and night. Additional features include owned solar panels, offering the potential for improved energy efficiency and reduced utility costs, along with thoughtful upgrades throughout that make this home truly move-in ready. Located in one of Winter Garden's most desirable communities, you'll enjoy the Waterleigh lifestyle with resort-style amenities, recreational opportunities and convenient access to shopping, dining, entertainment and major roadways. Beautifully upgraded. Designed for entertaining. Built for Florida living. 9572 Waterway Passage isn't just a house—it's the lifestyle you've been waiting for. Schedule your private showing today!

9572 Waterway Passage Drive, Winter Garden
$548,000
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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