Winter Garden/Oakland Homes with Stucco Exterior Construction

Winter Garden/Oakland Homes with Stucco Exterior Construction

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant local culture, these areas offer a delightful blend of suburban tranquility and urban convenience. With a rich history dating back to the early 1900s, Winter Garden has blossomed into a thriving town, while Oakland boasts a quaint, small-town atmosphere that attracts families and retirees alike.

As you explore the neighborhoods, you'll discover a variety of architectural styles, with homes featuring stunning stucco exteriors. This construction style not only adds a touch of elegance to the streetscape but also provides durability and energy efficiency, making it a popular choice among homeowners. Stucco homes are often characterized by their smooth, textured surfaces that can be painted in a myriad of colors, allowing for personalized curb appeal.

Living in Winter Garden and Oakland means enjoying a lifestyle enriched by outdoor activities, with easy access to beautiful parks, lakes, and nature trails. The area is also known for its vibrant downtown, where you can find charming boutiques, delightful eateries, and a lively farmers' market that showcases local produce and crafts.

Whether you're searching for a cozy family home or a spacious property with modern amenities, the stucco homes in this region are sure to impress. Embrace the warmth and charm of Winter Garden and Oakland, where community spirit thrives, and your dream home awaits!

Newest Winter Garden/Oakland Homes with Stucco Exterior Construction

5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to this newly updated 2 bedroom / 2 bathroom first floor condo in Winter Garden, where low-maintenance living meets comfort and convenience. This beautifully updated first-floor condo features fresh interior paint and new flooring, creating a bright, modern, and move-in-ready space. The open-concept floor plan offers comfortable living and dining areas, making it perfect for everyday living or entertaining. The well-designed layout provides a seamless flow, while large windows bring in an abundance of natural light. This condo hasa detached garage for easy parking near your home. Residents enjoy the outstanding amenities of this sought-after community, including a resort-style swimming pool, fitness center, clubhouse, playground, walking paths, and beautifully maintained green spaces. The HOA also provides low-maintenance living, allowing you more time to enjoy everything Winter Garden has to offer. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, shopping, dining, entertainment, major highways, and Orlando's world-famous attractions, this home offers an unbeatable combination of location and lifestyle. Whether you're a first-time homebuyer, seasonal resident, downsizing, or looking for an investment opportunity, this move-in-ready condo delivers exceptional value in one of Central Florida's most desirable communities.

130 Southern Pecan Circle Unit 103, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality.

7276 Windy Willow Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code

A Rare Opportunity in Encore at Ovation! This beautifully upgraded Jensen model is back on the market! Located just off Disney's Western Way, this exceptional home offers timeless designer finishes, an open-concept floor plan, and an unbeatable location just minutes from Walt Disney World. The stunning kitchen features 42-inch shaker cabinets, quartz countertops, an oversized island, dovetail drawers, and upgraded lighting. Waterproof wood-look flooring flows throughout the main level, while extra-height baseboards add a custom touch. The spacious primary suite includes a tray ceiling and a luxurious bath with a designer-tiled walk-in shower and semi-frameless glass enclosure. Bathrooms feature granite countertops and slate-look porcelain tile, with plush carpeting upstairs. A standout feature is the private backyard exclusive to this floor plan creating the perfect space to relax or entertain. Walt Disney World and Margaritaville Resort Orlando are both nearby, as well as premier shopping, dining, and entertainment. Don't miss this opportunity to own one of Encore at Ovation's most desirable homes. Schedule your private showing today!

13879 Lanyard Way, 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

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

Virtually Staged. Pre-Construction. To be built. Anna Maria with Bonus Room: Welcome to this spacious, thoughtfully designed 6-bedroom, 4.5-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. Upstairs, you'll find two generously sized bedrooms, each with access to it's own bathroom, along with a spacious game room that's perfect for movie nights, a play area, or a second living space.

17314 Wild Daisy Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Black Lake Preserve SubDv. ⋅ 34787 Zip Code

Welcome to 14343 Black Lake Preserve Street in Winter Garden, a beautifully upgraded pool home in the sought-after Black Lake Preserve community. Designed for both everyday living and unforgettable entertaining, this exceptional residence combines luxury finishes, premium technology, and thoughtfully designed living spaces. At the heart of the home is a stunning chef's kitchen featuring an impressive 13-foot center island, a GE Monogram wall oven, Thermador 5-burner cooktop, and a spacious walk-in pantry with custom built-in storage. The kitchen flows seamlessly into the main living areas and is complemented by an elegant formal dining room, providing the perfect setting for holiday gatherings, dinner parties, or everyday meals. Luxury vinyl plank flooring, crown molding, and a cozy fireplace add warmth and sophistication throughout the home. The spacious primary suite offers a private retreat with a custom walk-in closet system, while the dedicated theater room delivers an immersive entertainment experience with a 123-inch screen, 4K projector, and surround sound system. Step outside and enjoy Florida living at its finest. The backyard features a fully equipped outdoor kitchen with grill, griddle, and sink, making it the perfect space for entertaining family and friends. The sparkling pool is equipped with a new heat and cool pump, allowing for year-round enjoyment. Additional upgrades include a Generac whole-home generator, providing security and peace of mind during any season. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and area attractions, this move-in-ready home offers the perfect blend of luxury, comfort, and convenience. This is a rare opportunity to own a highly upgraded home in one of Winter Garden's most desirable communities.

14343 Black Lake Preserve Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Chapin Station A SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained pool home in the desirable Chapin Station community of Winter Garden, where location truly sets it apart. Just outside the neighborhood, you'll enjoy direct access to the West Orange Trail at the Chapin Station Trailhead, making it easy to bike, walk, run, or explore miles of scenic trails connecting Winter Garden, Clermont, Oakland, and beyond. Situated on an oversized homesite, this property offers the perfect blend of indoor comfort and outdoor Florida living with a private screened pool and spacious backyard ideal for entertaining and relaxing. Inside, you'll find a thoughtfully designed floor plan with generous living spaces, abundant natural light, and plenty of room for everyday living and hosting family and friends. Conveniently located just minutes from Historic Downtown Winter Garden, residents can enjoy the award winning Farmers Market, Plant Street, Crooked Can Brewing Company, boutique shopping, restaurants, live entertainment, and community events throughout the year. Downtown Clermont, Winter Garden Village, major highways including SR 429 and the Florida Turnpike, Walt Disney World Resorts, Disney Springs, world class sports training facilities, championship golf, and state of the art hospitals and medical centers are all within easy reach. This exceptional home combines an unbeatable location, outdoor recreation, convenient access to Central Florida's top attractions and amenities, and the vibrant lifestyle buyers are searching for.

1339 Hunterman Lane, Winter Garden

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, Brewery and 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. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden

6 Beds ⋅ 7 Baths ⋅ Avalon Ridge SubDv. ⋅ 34787 Zip Code

Built in 2024 and completely upgraded beyond builder standards, this 6-bedroom, 5-full-bath, 2-half-bath home in Avalon Ridge gives you the feel of a custom home without having to start from scratch. From the moment you walk in, you can see how much thought was put into every space. The home features custom woodwork, built-ins, upgraded flooring, designer lighting, window treatments, and fully customized closets throughout. The main floor is open, bright, and made for both everyday living and entertaining. A custom lounge near the entrance includes built-in cabinets, lighting, beverage refrigerators, extra storage, and a sitting area. The living room, dining area, and kitchen flow together and open to the covered outdoor space through large sliding glass doors. The kitchen features a large island, quartz countertops, stacked cabinets, stainless steel appliances, and plenty of storage. The same custom wood details continue into the surrounding living spaces, giving the entire first floor a finished and connected look. The primary suite is located downstairs and includes a large bathroom with dual sinks and a fully customized walk-in closet with glass doors, built-in shelving, display space, and a center island. Upstairs, there are additional bedrooms, a Jack-and-Jill bathroom, flexible rooms that can be used as guest rooms or offices, and a dedicated movie room with custom built-ins. Every closet in the home has been redone to create more usable storage. The home also includes upgraded vanities, trim, interior finishes, and wiring already in place for an electric vehicle charger. Complete plans for a custom pool are included with the sale, so the next owner can move forward with the project without having to begin the design process from the beginning, subject to approvals. Photos of pool virtually staged. Custom built-ins, installed light fixtures, window treatments, and curtains are included. Furniture and décor are not included in the list price and will be sold separately as a complete furniture package. This is a nearly new home with the upgrades, storage, and finished look that are hard to find in a standard new-construction home.

16077 Barkly Ridge Court, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code

LOCATION, LOCATION, LOCATION! Discover a rare gated lakefront retreat in the heart of Winter Garden, tucked away on a quiet, tree-lined cul-de-sac and conveniently located just minutes from local schools, grocery stores, dining, and Downtown Winter Garden. Enjoy grandfathered boat access on Lake Luntz, breathtaking sunset views, a screened pool with grotto seating and waterfall, a fully equipped Florida Grill/Bar room, and a private boathouse with a covered dock, boat lift, pontoon slip, and jet ski slips. Additional highlights include a guest suite, loft, media room, air-conditioned garage with gym/rec space, and two new AC systems installed in 2025—an exceptional combination of privacy, recreation, and waterfront living.

2450 Dahlgren Way, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code

LISTED AT APPRAISED VALUE! Welcome to this beautifully updated townhome in the highly desirable gated community of Daniels Landing in Winter Garden. Combining modern upgrades with an ideal location, this move-in-ready residence offers the perfect blend of style, comfort, and convenience. Step inside to discover an inviting open-concept main level featuring a spacious living room, a well-appointed kitchen with granite countertops, ample cabinetry, a dining area, and a convenient half bath for guests. Luxury wood plank flooring flows throughout the living room and both bedrooms, creating a warm and cohesive feel. Upstairs, you'll find two generously sized primary suites, each complete with walk-in closets and private en-suite bathrooms. The bathrooms were fully renovated in 2025 with designer tile flooring, new vanities, LED mirrors, beautifully tiled showers, new toilets, and contemporary fixtures, creating spa-inspired spaces you'll love. A conveniently located upstairs laundry area adds to the home's thoughtful layout. Extensive recent improvements provide exceptional peace of mind, including a complete HVAC system replacement (2022), new garage door and garage door opener (2025), professionally cleaned air ducts with a UV air purification system (2025), new ceiling fans throughout (2025), and a full suite of brand-new LG stainless steel appliances including the refrigerator, dishwasher, microwave, washer, and dryer (2025). Enjoy Florida living in your private courtyard, accessible from the rear-entry garage, offering a quiet outdoor retreat for relaxing or entertaining. Residents of Daniels Landing enjoy an array of community amenities, including a resort-style pool, fitness center, clubhouse, playground, and gated entry. Ideally situated just minutes from the award-winning Downtown Winter Garden, the West Orange Trail, shopping, dining, major highways, and approximately 20 minutes from Walt Disney World, this exceptional home offers the perfect combination of low-maintenance living and an unbeatable location.

241 Deepcove Road, Winter Garden

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