Winter Garden Homes with Courtyard Exterior Features

Winter Garden Homes with Courtyard Exterior Features

Welcome to Winter Garden, Florida – a picturesque gem nestled in the heart of Orange County. Known for its charming downtown area, rich history, and vibrant community, Winter Garden is more than just a place to live; it’s a lifestyle. With its tree-lined streets, boutique shops, and delightful eateries, this city offers a perfect blend of suburban tranquility and urban convenience. Residents enjoy easy access to the stunning West Orange Trail, which winds through lush landscapes and provides endless opportunities for outdoor activities.

When it comes to finding your dream home in Winter Garden, look no further than the enchanting properties featuring courtyard exterior designs. These homes boast a unique charm that sets them apart, offering private outdoor spaces perfect for relaxation or entertaining. Imagine stepping through your front door into a serene courtyard, where you can enjoy your morning coffee or host evening gatherings under the stars. The courtyard designs not only enhance the aesthetic appeal of the home but also provide a sense of privacy and tranquility that is hard to find elsewhere.

With a variety of architectural styles and sizes, Winter Garden’s courtyard homes cater to families, retirees, and everyone in between. The community is known for its friendly atmosphere, top-rated schools, and proximity to major attractions like Walt Disney World, making it an ideal place to call home. Explore the inviting neighborhoods of Winter Garden and discover the perfect courtyard home that suits your lifestyle and aspirations. Embrace the charm of Winter Garden – where community, comfort, and style come together beautifully!

Newest Winter Garden Homes with Courtyard Exterior Features

$399,000
3 Beds ⋅ 3 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Welcome home to this gorgeous end unit townhome in the heart of Hamlin! With capabilities of fencing in the side yard, this townhome offers potential unlike any other. Step inside and admire the fresh color palette this home boasts. With light wood-plank tile flooring, light countertops, light cabinetry, and lots of windows, this open concept downstairs feels incredibly warm and inviting. Updated lighting and window drapes elevate the space even more. Functionality and convenience were also taken into consideration in this downstairs with a cabinet and counter-lined drop zone upon entry into the home from the garage and patio, a closet pantry, and hallway leading to the half bathroom. Head upstairs where you will find a split bedroom floor plan with the primary suite on one side and the secondary bedrooms and Jack-and-Jill styled bathroom on the other, the space separated even further by the upstairs laundry room. Step out back to the private fenced-in brick-paved patio that separates the house from the two-car garage. The community is situated right in the middle of Hamlin’s shopping, dining, and entertainment offerings, super close to Disney, and right off of Highway 429 to bring you to all of your favorite Central Florida destinations. Inquire today on how to make this gem your own!

15579 Honeybell Drive, Winter Garden
$465,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private PVC fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2 car garage. Resort style amenities include clubhouse, gym, pool, soccer field, walking trails, tennis court, basketball court, playground, zip line & fishing dock. Walking distance to the Orange County National Golf Center, minutes to Disney, Downtown Winter Garden, endless dining & shopping. A MUST SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden
$453,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Experience refined Florida living in this beautifully appointed 2024-built residence, ideally situated within the gated community of Del Webb Oasis. Thoughtfully designed with 2 bedrooms plus a versatile bonus room—perfect as a 3rd bedroom, private home office, den, or sitting room—the home offers a desirable split-bedroom floor plan that provides both privacy and comfort. upgrades are showcased throughout, including luxury vinyl flooring, recessed lighting, and contemporary finishes. At the heart of the home, the stylish kitchen features Tier 3 upgraded finishes complemented by Whirlpool appliances, creating an inviting space that seamlessly blends modern design with everyday functionality. Step outside to the screened-in lanai, an ideal setting for peaceful morning coffee, outdoor dining, or relaxing Florida evenings. The 2-car garage is equally well appointed with sleek epoxy flooring and an EV charger for added convenience. Beyond the home, Del Webb Oasis offers a gated, amenity-rich lifestyle designed for recreation, relaxation, and connection. Association fees include cable and internet, while the community provides an exceptional setting to stay active, socialize, and enjoy the best of Florida living. Adding to its appeal, the property is approximately 20 minutes from the Walt Disney World Resort area, depending on traffic—placing world-class dining, shopping, entertainment, and recreation within easy reach. Built in 2024 and beautifully upgraded throughout, this exceptional residence delivers the perfect combination of modern luxury, low-maintenance living, and resort-style convenience.

13418 Princess Street, Winter Garden
$2,495,000
6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Virtually Staged. Lake Apopka view. Protected Conservation. Detached Guest apartment. Apartment over garage. In-Law suite. Multi-generational living describes 907 Celadon. Homesite is approximately 160 feet deep. A broad rear boundary of designated open space. No residential lot behind the home. The main home highlights include a massive open floor plan, oversized Chef's kitchen, a first-floor primary en suite, outdoor summer kitchen, two rooms directly off the foyer offering flexibility for two home offices, or one room as the downstairs en suite for guests or aging family members. The nearly 41-foot screened porch, with built in summer kitchen. The Detached Guest House is 907 Sq Ft, over the 3 car garage. Provides flexibility as the in-law suite, mother-in-law suite. Chef's Kitchen, offers generous workspace for more than one cook. Kitchen-Aid ovens and built-in ice maker by Manitowoc. Expansive sliding glass doors open the great room to the green conservation and Lake Apopka views. A long back yard overlooking a deep conservation vista. Room for a pool. The first-floor primary occupies its own wing at the rear and 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 lanai. Bathroom features frameless shower, free standing soak tub, and dual sinks across from each other. A custom walk-in closet dressing room —with extensive built-ins, a center island and chandelier—and primary en suite bath complete the wing. Upstairs, three bedrooms and an oversized loft provide the flexibility for a home theater, gaming and homework stations. Daily routines are easier here. Bright blue built-in lockers off the mudroom keep backpacks, sports equipment, shoes and bags organized, while the large laundry room includes a specialty built-in dog wash station. Connected to the main residence by a covered breezeway, the 907 Sq ft detached guesthouse/ADU sits above a 3-car garage and includes a kitchenette, full bath and closet. The garage also includes a golf-cart bay, and EV charging station. The guest house is currently used as a private executive office. Oakland Park and Winter Garden's golf-cart approved community zones is one of the signature advantages, offering easy access to Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—just a golf 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
$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
$595,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Short Sale. ~ LIKE-NEW LIVING in one of Winter Garden’s most sought-after communities! Just four years old, this beautiful DAVID WEEKLEY SUMMERTON MODEL is located in McKinnon Square within award-winning Oakland Park! High ceilings, abundant natural light and an OPEN CONCEPT design create a bright, welcoming interior made for everyday living and entertaining. At the heart of the home, the GOURMET CHEF’S KITCHEN flows seamlessly into the main living and dining spaces, while the inviting FRONT PORCH adds to the neighborhood feel Oakland Park is known for. All of the bedrooms are upstairs along with a versatile BONUS/LOFT offering endless possibilities as a home office, playroom, media space or second living area. Life here extends well beyond the front door – Oakland Park is a GOLF CART-FRIENDLY COMMUNITY offering a clubhouse, COMMUNITY POOLS, parks, playgrounds, a dog park and recreational amenities, plus easy access to the WEST ORANGE TRAIL and LAKE APOPKA. Cruise by golf cart to HISTORIC DOWNTOWN WINTER GARDEN for award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals and the popular Winter Garden Farmers Market. Everyday convenience is equally impressive, with the elementary school approximately .5 miles away, middle school 1.1 miles, high school 3 miles and Orlando Health Hospital approximately 1.8 miles away. Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike are easily accessible, with shopping, dining, Disney and Central Florida attractions within reach. MOVE-IN READY, nearly new and complete with a golf cart, this Oakland Park home delivers the lifestyle that makes Winter Garden such a desirable place to call HOME!

923 Colie Alley, Winter Garden
$224,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Welcome to low-maintenance living in the heart of Winter Garden! This charming 2-bedroom, 2-bathroom condominium offers approximately 840 sq ft of comfortable living space in the established Townhomes of Winter Garden community. Enjoy an open floor plan with a bright living and dining area, functional kitchen, and two well-appointed bedrooms, including a primary suite with its own bathroom. In-unit laundry (washer and dryer) adds everyday convenience. The community features a sparkling pool, exterior maintenance, and landscaping included in the HOA, making this an easy, lock-and-leave lifestyle. Prime location just minutes from Historic Downtown Winter Garden’s shops, restaurants, farmers market, and the West Orange Trail. Quick access to Highway 50, Winter Garden Village (shopping, dining, and more), and major roadways for easy commuting throughout Central Florida. Ideal for first-time buyers, downsizers, or investors seeking a solid rental property in a desirable Winter Garden location. Pets are typically allowed (buyer to verify HOA rules). Schedule your private showing today!

300 Eron Way Unit 1, Winter Garden
$440,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
Discover an inviting 3-bedroom, 2.5-bath home in Winter Garden, offering a comfortable layout designed for both everyday living and entertaining. The main living areas create an open and welcoming environment, with natural light enhancing the sense of space and connecting the living, dining, and kitchen areas. Upstairs, the bedrooms are thoughtfully separated from the main gathering spaces, providing added privacy and a comfortable retreat at the end of the day. The primary suite offers its own private bath, while the additional bedrooms provide flexibility for family, guests, a home office, or whatever best fits your lifestyle. Beyond the home itself, the location puts you close to everything that makes the Winter Garden area so desirable. Enjoy convenient access to shopping, restaurants, schools, recreation, and major roadways, making it easy to explore Horizon West, greater Orlando, and the many attractions Central Florida has to offer. Whether you're searching for your next home or an investment opportunity in a growing area, this property delivers a combination of location, functionality, and Florida living that is hard to overlook. Schedule your private showing and come see the possibilities for yourself.

15038 Windflower Alley, Winter Garden
$399,999
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation Phase 1 SubDv. ⋅ 34787 Zip Code
BACK ON THE MARKET AND PRICED TO SELL!! Why wait for new construction when this move-in-ready Ashton Woods home in Northlake at Ovation is ready for you now? Tucked away among the beautiful conservation areas of Horizon West, this hidden Winter Garden gem offers modern style, fantastic amenities, and an unbeatable location. The award-winning Kendall II floor plan features 3 bedrooms, 2.5 baths, 1,584 sq. ft., a private brick-paver courtyard, and a full-size 2-car garage. The open-concept first floor showcases wood-look ceramic tile and a stylish kitchen with quartz countertops, stainless steel appliances, designer lighting, and modern finishes, flowing seamlessly into the dining and living areas. Upstairs, the spacious Owner’s Suite offers a walk-in closet and private bath with dual vanities and an oversized shower. Two additional bedrooms, a full bath, and a versatile loft/landing provide plenty of room for guests, a home office, or additional living space. Enjoy the Northlake lifestyle with a community clubhouse, resort-style pool, playground, and dog run. Publix, restaurants, shopping, schools, and bike paths are just minutes away, along with convenient access to Disney, SR-429, and I-4. Newer construction without the wait—and priced to MOVE! Schedule your showing today before this Winter Garden opportunity is gone!

17723 Japonica Bloom Drive, Winter Garden
$410,000
3 Beds ⋅ 3 Baths ⋅ Ravenna Ph 1 SubDv. ⋅ 34787 Zip Code
BEAUTIFUL two-story townhome in the desirable Ravenna community. This spacious 3 bed/2.5 bath offers low-maintenance living in a prime Winter Garden location. The main level is an open-concept with a half bathroom for guests. The kitchen features QUARTZ countertops, stainless steel appliances, a large kitchen island and a breakfast bar...PERFECT for entertaining! All bedrooms are located on the second floor along with the laundry closet. The primary suite includes a WALK-IN closet and an en-suite bathroom with double vanity sinks. Enjoy outdoor living on the private back patio, which leads to the 2-car garage. The community features a POOL and playground. It is conveniently located in Winter Garden near grocery stores, restaurants and top rated schools.

8013 Basilica Lane, Winter Garden
$519,995
3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code
*This home can be purchased with NO MONEY DOWN or NO INCOME VERIFICATION* 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
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