Winter Garden Homes with Traditional Architectural style

Winter Garden Homes with Traditional Architectural style

Welcome to Winter Garden, Florida, a charming city that perfectly blends small-town warmth with modern conveniences. Nestled just a stone’s throw from the bustling heart of Orlando, Winter Garden boasts a rich history, vibrant community, and an array of outdoor activities that make it a delightful place to call home.

One of the standout features of Winter Garden is its picturesque downtown area, lined with quaint shops, delightful restaurants, and a lively farmers market. The historic district exudes a welcoming atmosphere, where neighbors gather, and families create lasting memories. Nature lovers will appreciate the stunning parks and scenic trails, including the West Orange Trail, which offers miles of picturesque views perfect for walking, biking, and enjoying the Florida sunshine.

When it comes to real estate, Winter Garden is renowned for its stunning homes that showcase traditional architectural styles. These residences often feature classic elements such as gabled roofs, charming porches, and elegant brickwork, providing a sense of timeless beauty and character. The community embraces this traditional aesthetic, ensuring that the homes not only reflect the rich heritage of the area but also cater to the modern needs of families and individuals alike.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Garden’s real estate market offers a variety of options that embody the charm and warmth of traditional architecture. Discover your dream home in this enchanting city, where community spirit and beautiful surroundings come together to create the perfect place to live.

Newest Winter Garden Homes with Traditional Architectural style

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Oak Park At Winter Garden SubDv. ⋅ 34787 Zip Code

Located in the desirable charming golf cart community of Oak Park within a couple blocks of walking distance (or golf cart) to historical Winter Garden vibrant downtown with dining, boutique shopping and entertainment featuring a theatre and an award-winning farmers market. This well built cement block Maronda home offers a blend of charm and convenience with low HOA dues, and can be easily updated. Step out of this home into a wonderful screened heated pool and covered lanai for year-round enjoyment. The almost third acre lot is fenced on 3 sides and easily fenced and gated on each side for privacy. Within the wooded area in the back of the lot is an attractive storage shed. Veterans Memorial Park borders on the rear of the property featuring several acres of a variety of sports, including ten pickleball courts, picnic areas and playgrounds for families and pets. Hop on the scenic West Orange Trail just minutes from this home for a walk, run or bike ride. Commuting via the 429 and the Florida Turnpike gives easy access to all of Central Florida and its theme parks.

665 Stevelynn Circle, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. Anna Maria with Bonus Room: Welcome to this spacious, thoughtfully designed 5-bedroom, 3.5-bath home, offering the perfect blend of comfort and functionality. The heart of the home is the expansive kitchen, featuring a large center island that's ideal for cooking, entertaining and gathering with friends. The private primary suite is conveniently located on the first floor, providing a peaceful retreat with added privacy. The second floor features a large private bedroom, full bathroom, and an oversized game room, making it an ideal space for guests, older children, or a dedicated entertainment area.

17338 Wild Daisy Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

**Virtual staging in formal living and dining rooms. Video available.** Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

17320 Wild Daisy Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden

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

5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code

Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code

Presenting an affordable investment in the Winter Garden area between the infamous Plant St and Hwy 50! This larger 2 bedroom/2 bath condo provides convenience in the location added to the maintenance free exterior. It is a small quaint community with only 50 condos. The pool is large with depths up to 8 feet. The condo has been well maintained with upgrades. Whether you're a first-time homebuyer, looking for a winter home or searching for a fantastic investment opportunity, this home checks all the boxes. Location is everything…Just minutes from the award-winning Historic Downtown Winter Garden. On Saturday mornings make your way to the Winter Garden Farmers Market for all the fresh foods you can imagine, along with retail and cooked food items. Any day of the week head on over to the Plant St area for browsing boutiques, enjoying locally owned restaurants, coffee shops, breweries and year-round community events. Outdoor enthusiasts will appreciate easy access to the scenic West Orange Trail, offering miles of paved paths for walking, running and biking. Need to shop at the big box retail stores, head South to the popular Winter Garden Village, the ultimate shopping destination. Very close by is a Publix shopping center and an Aldi. Winter Garden continues to be one of Central Florida's most desirable communities thanks to its small-town charm, top-rated amenities, vibrant downtown, and convenient access to major highways, Orlando, world-famous attractions, shopping, dining and entertainment. Access to the Turnpike is a short distance away, along with the 429 Freeway (is the way to Disney) and the 408/I4 Freeway (is the way to Universal Studios). This property qualifies for low down payment programs for primary buyers. New roofs start August 2026!

320 Eron Way Unit 6, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code

Virtually Staged. CUSTOM, Like-New HOME with a large fenced-in yard in the heart of WinterGarden’s highly sought after Hamlin/Horizon West area. This home features the most desired floor plan built by the custom builder - Ashton Woods homes. It features 4 Bedrooms, 3.5 Baths, office, formal dining/flex space, 2 story impressive great room that you must see in person, a wrap-around full lanai with nice private backyard views. On the main level is the office with french doors, flex space/dining room, a Grand Gourmet Kitchen with butlers pantry that has every upgrade imaginable: custom cabinets, Stainless appliances, quartz counters, custom tile backsplash, whole home water filtration, and wood plank floors. The open layout kitchen with dine-in island flows into the expansive 2 story great room which has nice views of the expansive backyard. You can enjoy the perfect space to spend time with family and friends under the expanded, extended screened, wrap around Lanai with plenty of space to enjoy time with friends and family. Upstairs you’ll find the 3 secondary bedrooms and baths. The large primary suite features plenty of windows, dual vanities, a frameless glass shower with designer tile work, and large walk in closets. Other notable features include: large fenced yard, whole home water filtration, and more. Located in a highly desired community with resort style pool and splash pad, plenty of amenities, parks, walking trails, lakes and more. This sought-after Horizon West community is part of one of the fastest growing communities in the country with shopping, restaurants, movie theater, high rated schools, parks and a hospital all a short distance to the home. The community has easy access to FL-429, FL turnpike and Disney is only 15 minutes away! Downtown Orlando is 25 minutes so a quick commute to about anywhere you would want to go.

15372 Sugar Citrus Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 4-bedroom, 3.5-bath home situated on one of the largest corner lots in the highly sought-after Waterleigh community in Winter Garden. Offering nearly 3,000 square feet of thoughtfully designed living space, this home blends timeless style, comfort, and functionality. Step inside to an inviting open-concept floor plan filled with natural light, where the living room, dining area, and kitchen flow seamlessly together—perfect for both everyday living and entertaining. Plantation shutters throughout add elegance and charm. The gourmet kitchen is the heart of the home, featuring 42-inch espresso cabinetry, granite countertops, stainless steel appliances, a spacious island, and abundant storage, all overlooking the family and dining areas. The first floor offers flexibility with a private bedroom and full bath, ideal for guests or multigenerational living, along with a dedicated home office bathed in natural light. Upstairs, you’ll find a spacious loft that can easily serve as a media room, playroom, second living area, or additional office. The luxurious primary suite provides a peaceful retreat with room for a king-sized bedroom set, a large walk-in closet, and a spa-inspired ensuite featuring dual vanities, a walk-in shower, and a soaking tub. Two additional bedrooms share a full bathroom with dual sinks, while the conveniently located second-floor laundry room adds everyday convenience. Outside, enjoy your covered lanai overlooking the oversized backyard—one of the largest lots in the neighborhood—with plenty of room to build your dream pool while still maintaining green space. The three-car tandem garage provides ample parking and storage. Living in Waterleigh means enjoying resort-style amenities, including: three clubhouses, three resort-style pools, two fitness centers, tennis, pickleball, volleyball, and mini golf, walking and biking trails, dog park, fishing pier, playgrounds, and scenic lakes. Lawn maintenance included through the HOA Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, shopping, dining, and top-rated schools, this home truly offers the best of Central Florida living. Don’t miss your opportunity to own this exceptional home—schedule your private showing today!

16304 Wind View Lane, Winter Garden

6 Beds ⋅ 4 Baths ⋅ Johns Cove SubDv. ⋅ 34787 Zip Code

Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and dining rooms, a large family room, soaring vaulted ceilings, and a double staircase. The kitchen offers stainless steel appliances, granite countertops, a large island, abundant cabinetry, and a breakfast area with tranquil pond views. The first-floor primary suite overlooks the pool and includes an en-suite bath with dual vanities, garden tub, separate shower, and walk-in closet. Upstairs offers generously sized bedrooms and a dedicated movie room. Enjoy a screened heated saltwater pool and spa, updated full pool bath, covered lanai, private balcony, and no rear neighbors. Residents enjoy a private boat ramp on Johns Lake, ideal for bass fishing, boating, paddle boarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, dining, shopping, and top-rated schools.

1603 Johns Cove Ln, Oakland

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