Winter Garden Homes with Courtyard Exterior Features

Winter Garden Homes with Courtyard Exterior Features

Winter Garden, located in Orange County, Florida, is a charming city that offers a perfect blend of small-town charm and modern amenities. With its picturesque streets, friendly community, and a wide array of recreational activities, Winter Garden is a sought-after destination for homebuyers.

One of the standout features of homes in Winter Garden is the courtyard exterior design. With a true emphasis on outdoor living, these homes offer a unique and inviting space that seamlessly blends indoor and outdoor living. The courtyard serves as a private oasis, perfect for relaxation and entertainment.

Whether you're looking for a cozy bungalow or a spacious family home, Winter Garden has a variety of options to suit your needs. Many of these homes boast beautiful landscaping, well-manicured lawns, and stunning architectural details that add to their curb appeal.

Living in Winter Garden means enjoying a vibrant community with a rich history. The city's historic downtown district is a popular gathering spot, offering a wide range of dining, shopping, and entertainment options. Residents can explore the local farmers market, attend community events, or simply take a leisurely stroll along the charming streets.

In addition to its small-town charm, Winter Garden also boasts excellent schools, parks, and recreational facilities. The city is known for its numerous parks and trails, making it a haven for outdoor enthusiasts. From boating and fishing on Lake Apopka to hiking and biking on the West Orange Trail, there's no shortage of activities for nature lovers.

With its desirable location, stunning homes with courtyard exterior features, and a thriving community, Winter Garden is a city that offers an exceptional quality of life. Whether you're looking to raise a family or enjoy your retirement years, Winter Garden has something to offer everyone.

Newest Winter Garden Homes with Courtyard Exterior Features

$479,000
3 Beds ⋅ 3 Baths ⋅ Latham Park North SubDv. ⋅ 34787 Zip Code
WINTER GARDEN LIVING AT ITS BEST! | ORIGINAL OWNERS | FULLY PAID-OFF SOLAR | TESLA EV CHARGER | UPDATED FIRST-FLOOR LAMINATE FLOORING | ABUNDANT NATURAL LIGHT | OVERSIZED PRIMARY RETREAT | FENCED BACKYARD + PAVERS | LATHAM PARK NORTH | Welcome to 8931 Doddington Way, a beautifully maintained, original-owner home located in the highly sought-after Latham Park North community in the heart of Horizon West. Purchased directly from Ashton Woods in 2016, this premium home features elevated builder finishes, including upgraded flat-textured walls for a more refined look than typically found throughout the neighborhood and surrounding area. Downstairs, an abundance of windows fills the home with natural light, creating a bright and welcoming atmosphere throughout the main living spaces. Updated laminate flooring spans the first floor, giving the home a clean, cohesive look while connecting the kitchen, dining, and living areas. Custom built-ins, including an entertainment center and mudroom, add both character and functionality. An additional flex space offers even more versatility and is perfectly suited for a small home office, butler’s pantry, pet room, or additional storage. Upstairs, the home transitions into its private living spaces, highlighted by an impressively spacious primary room. The oversized primary bedroom offers plenty of room to create a true retreat and is complemented by a large walk-in closet and expansive ensuite bathroom featuring a generously sized walk-in shower. Additional bedrooms complete the upper level, along with a full guest bathroom featuring a shower/tub combination and a conveniently located upstairs laundry room with gas dryer. Outside, the fully fenced backyard has been enhanced with added pavers for additional outdoor living and entertaining space, along with French drains and whole-home gutters for added functionality. The home also offers several high-value modern features, including a FULLY PAID-OFF solar system with no solar loan or lease to assume, a Tesla Wall Connector for at-home EV charging, a whole-home water system, and whole-home surge protection. Additional improvements include exterior paint in 2023, a new refrigerator in 2025 (which makes four styles of ice), and a new garage door opener and keypad in 2025. Located within Latham Park North, residents enjoy community amenities including a pool, playground, sidewalks, and green spaces, all just minutes from Hamlin’s shopping, dining, entertainment, and everyday conveniences. Easy access to SR-429 keeps Downtown Winter Garden, Orlando, and Central Florida attractions within easy reach. 8931 Doddington Way is a home you won’t want to miss. Schedule your private showing today!

8931 Doddington Way, 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
$450,000
3 Beds ⋅ 3 Baths ⋅ Orchard Hills Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome to 5887 Cypress Hill Rd, a beautifully maintained 3-bedroom, 2.5-bath home located in the highly desirable Orchard Hills community of Winter Garden. Built in 2017, this spacious 1,810-square-foot home offers an inviting open floor plan with high ceilings, modern finishes, and plenty of natural light. The kitchen features granite countertops and opens seamlessly to the main living and dining areas, making it ideal for both everyday living and entertaining. The primary suite offers a comfortable retreat with a walk-in closet, while the additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy the convenience of a 2-car garage, low-maintenance living, and a location just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways including the 429. Orchard Hills residents enjoy fantastic amenities including a community pool, clubhouse, fitness center, playground, dog park, sidewalks, and lawn maintenance included with the HOA. With its combination of comfort, convenience, and an exceptional Winter Garden location, this home is a must-see!

5887 Cypress Hill Road, 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
$229,000
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
$455,000
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
$390,000
3 Beds ⋅ 3 Baths ⋅ Hamilton Gardens SubDv. ⋅ 34787 Zip Code
You found it! Amazing LOCATION and priced to sell! You will love the open floorplan and PRIVATE COURTYARD that is perfect for outdoor gatherings. REAR-ENTRY TWO-CAR GARAGE in the highly desirable Hamilton Gardens community! The bright kitchen features granite countertops, a spacious pantry, and overlooks the dining area and great room, creating a seamless layout. Enjoy peaceful views of mature trees with NO REAR NEIGHBORS. Hamilton Gardens offers RESORT-STYLE POOL, cabana, dog park, and playground. Residents even enjoy NIGHTLY DISNEY FIREWORK VIEWS right from the community! Located in the HEART OF HAMLIN in sought-after HORIZON WEST just minutes from Hamlin Town Center with dining, cafés, entertainment, and a weekly farmers market. Convenient to SR 429, TOP-RATED SCHOOLS, major medical facilities, Winter Garden Village, Historic Downtown Winter Garden, Windermere, and ALL DISNEY ATTRACTIONS. Don't miss this one!

6208 Aralia Ivy Lane, Winter Garden
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