Winter Garden/Oakland Homes with Courtyard Exterior Features

Winter Garden/Oakland Homes with Courtyard Exterior Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and vibrant community spirit, this area seamlessly blends the charm of small-town living with the conveniences of urban life. Just a stone's throw away from the bustling city of Orlando, Winter Garden boasts a rich history that is beautifully reflected in its quaint downtown, featuring historic buildings, delightful boutiques, and a variety of restaurants that cater to all tastes.

One of the standout features of homes in this region is their stunning courtyard exterior designs. These homes are not just dwellings; they are inviting sanctuaries that encourage outdoor living and foster a sense of community. Imagine stepping through your front door and being greeted by a beautifully landscaped courtyard, perfect for morning coffee or evening gatherings with family and friends. The open-air spaces are designed to maximize Florida’s sunny climate, providing a serene backdrop for relaxation and entertainment.

In Winter Garden and Oakland, you’ll find a diverse array of homes with courtyard features that cater to various lifestyles. Whether you’re seeking a cozy bungalow or a spacious family home, these properties offer a unique blend of comfort and style, making them ideal for both first-time buyers and seasoned homeowners. With a strong sense of community, top-rated schools, and an abundance of recreational activities, Winter Garden and Oakland are truly exceptional places to call home. Embrace the charm of this region and discover the perfect courtyard home that suits your lifestyle!

Newest Winter Garden/Oakland Homes with Courtyard Exterior Features

$2,495,000
6 Beds 7 Baths Oakland Parka SubDv. 34787 Zip Code
Virtually Staged. In sought-after Oakland Park, 907 Celadon offers a rare combination: an expansive main residence, a private 907-square-foot carriage house apartment for multigenerational living, and generous indoor-outdoor spaces made for work, family time, entertaining and extended family, overlooking a broad conservation landscape and Lake Apopka. The main residence spans 5,247 heated square feet, with 7,142 total square feet across the property. Just inside the foyer, two substantial rooms face one another behind double French doors, one with its own en suite bath, giving a busy household the flexibility for two private offices at home, a private guest room, or, when live-in childcare is part of the picture, an ideal space for an au pair. Across the rear of the home, the kitchen, dining and living areas unfold as one expansive social space, with sweeping views across the conservation landscape to Lake Apopka. The kitchen is large enough for more than one cook to work side by side, with extensive cabinetry throughout—including an entire wall of cabinetry—plus storage beneath the oversized island and seating for six. KitchenAid ovens, a dedicated ice machine, under-counter microwave and double-door refrigerator support everything from busy weekday dinners to a house full of guests. A long wall of sliders opens to the nearly 40-foot screened porch and new summer kitchen, allowing time together to move easily from indoors to out. Beyond the porch, the fully landscaped backyard offers generous green space with room to envision a future pool and pool house. Set apart from the energy of the main living spaces, the first-floor primary suite spans its own wing along the rear right side of the home. A door from the kitchen closes the wing from the rest of the first floor, while the bedroom opens directly to the screened porch. An expansive dressing room—with extensive built-ins, a center island and chandelier—and a spacious primary bath complete the suite. Upstairs, three bedrooms and an oversized loft give younger family members a dedicated level of their own. The loft is currently arranged for movies, Xbox, play and a homework station, giving them a place of their own while the first floor remains where everyone comes together. Busy mornings and after-school arrivals are easier here. Bright blue built-in lockers off the mudroom keep backpacks and shoes organized, while the large laundry room includes a dedicated dog wash station—so even the family dog has a space of its own. For multigenerational living, the 907-square-foot carriage house apartment makes it possible for extended family to stay close without giving up the comfort and independence of a home of their own. Longer visits feel easier and more natural. Connected to the main residence by a covered breezeway, it includes a separate entrance, kitchenette, full bath and closet. Currently used as a private executive office, it can serve as guest quarters today or evolve into an in-law suite as family needs change. Oakland Park’s golf-cart lifestyle is one of its signature advantages, and 907 Celadon has a dedicated garage for it. Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—is an easy cart ride from home. Direct access to the West Orange Trail offers 22 miles for walking, jogging and biking, plus community pools and green spaces.

907 Celadon Street, Winter Garden

$749,999
4 Beds 5 Baths Burchshire SubDv. 34787 Zip Code
Experience luxury and versatility in this exceptional CUSTOM 2025-BUILT RESIDENCE, where thoughtful design, impressive scale, and high-end finishes come together to create a truly one-of-a-kind home. Featuring 4 BEDROOMS AND 5 PRIVATE ENSUITE BATHROOMS, WITH EVERY BEDROOM FEATURING ITS OWN ENSUITE, this home offers an extraordinary level of comfort, privacy, and flexibility rarely found in Winter Garden. Designed with luxury in mind, the home showcases 12-FOOT CEILINGS THROUGHOUT, including the impressive 2-CAR GARAGE, elegant PORCELAIN TILE FLOORING, and CUSTOM MATCHING QUARTZ COUNTERTOPS THROUGHOUT THE KITCHEN AND FURNITURE TOPS. Each ensuite bathroom features its own UNIQUE CUSTOM DESIGN, with spacious layouts, luxurious finishes, and distinctive details that give every bathroom its own character. The expansive open-concept living areas create an incredible atmosphere for both everyday living and entertaining, while the ENCLOSED FRONT LANAI, REAR LANAI, AND PAVED PERGOLA extend the living space outdoors and provide multiple areas to gather, relax, and enjoy the Florida lifestyle. The home's flexible design offers even more potential. Two bedrooms are currently separated by a drywall partition originally incorporated for an Airbnb concept, which can easily be removed to create a more open configuration or customized to suit your needs. Whether you're looking for an impressive primary residence, a multigenerational home, private guest accommodations, or an investment opportunity, this property offers flexibility that is hard to find. Opportunities like this are rare. Located just minutes from Downtown Winter Garden and within the coveted Golf Cart District, residents can enjoy easy access to Plant Street, the weekly farmers market, local dining, boutiques, breweries, parks, community events, and the West Orange Trail. Zoned for “A-RATED” Tildenville Elementary and West Orange High School, this home brings together everything today's buyer is looking for — custom construction, exceptional space, luxury finishes, versatility, and an unbeatable location. This isn't simply a new home — it's a custom-built opportunity designed to stand out.

809 Burch Avenue, Winter Garden

$850,000
4 Beds 4 Baths Oakland Parkb-3 SubDv. 34787 Zip Code
Under Construction. Rare opportunity to finish a custom AR Homes "Carrabelle" build exactly the way you want it - priced to reflect its current stage. 166 Hammock Preserve Loop is roughly three-quarters complete: framing, block construction, roof, windows, and drywall are in, and the home is currently paused at that stage. What's left is the fun part - flooring, cabinetry, fixtures, paint, and finishes - which means the next owner gets to select every surface in a 3,186-square-foot, four-bedroom, four-bath custom home instead of settling for someone else's choices. The Carrabelle plan delivers a two-story, open-concept layout on a 6,914-square-foot corner homesite in Oakland Park: a first-floor guest suite and flex room, a dramatic 21-foot foyer, an open kitchen and great room with decorative beams, a covered lanai and cabana with an open-air courtyard and fireplace, and a second-floor primary suite with a spa-style bath and walk-in closet. A three-car garage and an optional suite above it round out the plan. Full floor plan available on request. Sold AS IS. The original building permit has expired and is disclosed; a buyer will need to re-permit to resume construction. AR Homes has provided an itemized estimate to complete the home - available to serious buyers - along with the original plan set and specifications, so you're not guessing at scope. This is a straightforward, priced-to-reflect-its-stage opportunity for a buyer (or a buyer working with their own GC) who wants a real custom home in Oakland Park without paying new-construction-complete pricing for it. Located in the sought-after Oakland Park community, with tree-lined streets, walking trails, and community events, close to downtown Winter Garden's shops and dining. Cash, conventional, or construction/renovation financing. Buyer and buyer's agent to verify all information including HOA details, permit status, and completion costs. Seller makes no representations or warranties regarding the condition or completeness of existing work.

166 Hammock Preserve Loop, Oakland

$205,000
3 Beds 3 Baths Grove Resort And Spa Hotel Condominium 22019039615 SubDv. 34787 Zip Code
The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! This 5th-floor corner unit is the largest "Sable" model in the community, offering 1,544 sq ft with an open living/dining/kitchen area, a separate in-unit utility/laundry room, and a screened balcony. The kitchen features stainless steel appliances and granite counters. The primary suite includes an extra sitting area/solarium with direct balcony access, a bath with double sinks, a separate shower and soaking tub, and a large walk-in closet with a safe. Each bedroom includes a flat-screen TV. This condo-hotel offers an in-house hotel rental program that generates income to offset the cost of ownership — an ideal opportunity to own an Orlando/Disney-area vacation home just 6 miles from Walt Disney World. Resort amenities are exceptional. Surfari Water Park features the FlowRider Double Surf Simulator (one of only a few double units in the U.S.), dual water slides, a 695-foot lazy river, a zero-entry pool, and a kids' activities pool. The Springs Pools offer three full-sized pools, an oversized hot tub, a splash area, and private cabanas. Lake Austin provides catch-and-release fishing, watersports, and a lakeside pier overlooking the nature preserve. Additional amenities include a 24-hour fitness center, Flip Flop's Fun Center with a glow-in-the-dark indoor mini golf course and arcade, and a Kids' Activity Center. Dining options abound: The Springs Bar & Grill for relaxed poolside dining, Longboard Bar & Grill overlooking the FlowRider, Alfresco Market for outdoor cafe seating, and DYVE at The Terraces above the upscale pool area. The resort also offers daily transportation to Walt Disney World, Universal Orlando, and SeaWorld, plus complimentary resort-wide Wi-Fi. A rare chance to own a turnkey resort residence in one of the Orlando area's premier destinations.

14501 Grove Resort Avenue Unit 2542, Winter Garden

$1,350,000
6 Beds 5 Baths Waterside/Johns Lk-Ph 1 SubDv. 34787 Zip Code
Virtually Staged. With a whisper of Tuscan charm, Waterside on Johns Lake is a private GATED community featuring this impressive 6 BEDROOM (w/additional 7th room) 4.5 BATHROOM estate. As you pull up you will be welcomed by curb appeal, thoughtful landscaping, entry courtyard, 2 CAR GARAGE, and separate BOAT/TOY GARAGE. Inside the ceilings soar: with lots of NATURAL LIGHT, specialty molding, WOOD BEAMS, iron railings, built-ins, and a balance of both open concept & compartmentalized spaces. Downstairs you will find the 2-story ceiling Living Room, both FORMAL & CASUAL DINING space, Laundry Quarters, Butlers Pantry, Nanny's Workspace, Office, IN-LAW SUITE, and Primary Bedroom with SPA STYLE ENSUITE featuring a massive RAINSHOWER, GARDEN TUB, DOUBLE WALK IN CLOSETS, and separate vanities. And let's take a moment to discuss the CHEF'S KITCHEN that you will no longer have to envy, because as the new owner of this home you can whip up family meals or dinner party delights using your KITCHENAID 5 BURNER RANGE, convenient POT-FILLER set into glass tile backsplash, INDUSTRIAL DOUBLE REFFIGERATOR, oversized kitchen island, coffee bar, desert bar, KITCHENAID DOUBLE WALL OVEN, built-in Convection Oven/Microwave, and walk-in Pantry. Up the stairway lined with ironwork and over the landing, you reach the SUPERSIZED LOFT before leading to the 4 MORE BEDROOMS and 2 bathrooms. Currently one of the bedrooms is being used as an in-home gym and another as a craft room. The other 2 are joined by a JACKNJILL BATHROOM, perfect for kiddos or SECONDARY IN-LAW SUITE/Living space combo. With so much space, this home will suit most any lifestyle needs. For outdoor living you will find a large FENCED YARD off a COVERED LANAI with NO REAR NEIGHBORS and privacy bushes. Space for a future pool and outdoor entertaining customized just how you like it. For existing outdoor recreation, Waterside on Johns Lake offers a clubhouse, fitness center, community pool, trails, playgrounds, and a community dock perfect for watching cotton candy sunsets. Zoned for A rated public schools & nearby private school options. Nearby there is an abundance of restaurants, shopping, convenience, and the sought after Downtown Winter Garden lifestyle. Come see this spacious estate that you will want to call home soon. FLOORPLAN IN ATTACHMENTS

16730 Rusty Anchor Road, Winter Garden

Start Your Search