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, Florida—where charming small-town vibes meet modern conveniences. Nestled in the heart of Orange County, this picturesque area is renowned for its vibrant downtown, lush landscapes, and a rich tapestry of history that dates back to the 19th century. With its stunning parks, scenic lakes, and a thriving community, Winter Garden and Oakland offer a lifestyle that beautifully balances relaxation and recreation.

One of the standout features of homes in this area is the captivating courtyard exterior design. These homes exude a sense of warmth and welcome, providing a perfect blend of privacy and community. Imagine stepping into your own tranquil oasis, where lush gardens and inviting courtyards create a serene retreat right at your doorstep. Whether you’re hosting a summer barbecue or enjoying a quiet evening under the stars, these outdoor spaces serve as an extension of your living area, perfect for both entertaining and unwinding.

Winter Garden is also home to a variety of amenities, including delightful shops, gourmet restaurants, and the renowned West Orange Trail, ideal for biking and walking enthusiasts. With a strong sense of community and a commitment to preserving its natural beauty, this area offers not just a home but a lifestyle.

If you’re seeking a residence that combines the charm of courtyard living with the convenience of modern amenities, Winter Garden and Oakland are waiting to welcome you home. Explore the possibilities today and discover the perfect blend of comfort and community in this delightful Florida gem!

Newest Winter Garden/Oakland Homes with Courtyard Exterior Features

$239,000
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
$470,782
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, this home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. This low maintenance townhome includes a detached two car garage with private fenced courtyard space. The open kitchen boasts plenty of modern upgrades from the AW Collection Coastal such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings. The main living areas feature wood look luxury vinyl plank flooring and the bedrooms include upgraded carpet for comfort, plus find upgraded 8' doors throughout the home. Enjoy the neighborhood amenities including a community pool, clubhouse, shaded playground, and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17398 Sweet Moro Drive, Winter Garden
$309,000
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
$400,000
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
$569,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Property in a prime area right behind the Disney parks that lets you enjoy the parks' fireworks. In an excellent community to live in, just 1 block from one of the community pools, and inside are A1+ schools, so don't wait to come see your new home!

15929 Moonlight Bay Street, Winter Garden
$405,000
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Virtually Staged. BOLD PRICE REDUCTION for LUXURY IN SUMMERLAKE! This MOVE-IN-READY, Energy Star Certified townhome offers the perfect blend of style, comfort, luxury and convenience with 3 bedrooms, 2.5 baths, a 2-car garage, and 1,738 square feet of thoughtfully designed living space. Recently refreshed with NEW interior PAINT and NEW CARPETING, this home welcomes you from the moment you step onto the covered front porch. Inside, the open-concept floor plan is enhanced by contemporary wood-look tile flooring throughout the first level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen featuring granite countertops, rich 42-inch wood cabinetry, stainless steel appliances, a large center island with sink and breakfast bar, walk-in pantry, and a convenient built-in desk workspace. Whether preparing meals or entertaining guests, the open design keeps everyone connected. Step outside to your private, partially fenced courtyard with brick pavers—an ideal setting for morning coffee, outdoor dining, or relaxing after a busy day. The courtyard leads directly to the detached 2-car garage for added convenience. Upstairs, you'll find all three bedrooms, the laundry area, and new carpeting throughout. The spacious primary suite easily accommodates a king-size bed and features a large walk-in closet and an en-suite bath with dual granite vanities, a garden tub, and separate shower. Two additional bedrooms share a full bath with granite countertops. Located in the highly desirable Summerlake community, residents enjoy outstanding resort-style amenities including a community pool, clubhouse with fitness center and recreation room, pickleball/tennis and basketball courts, playgrounds, zip line, parks, dog park, and scenic walking trails. The home is conveniently located near Summerlake Elementary School and a neighborhood park. Summerlake, Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! As an added entertainment bonus, enjoy spectacular nightly Disney fireworks from designated viewing areas throughout the community. Just minutes from Hamlin Town Center, Cinépolis Luxury Cinemas, Orange County National Golf Center & Lodge, shopping, dining, and major roadways. This luxurious, beautifully updated home offers an exceptional opportunity to enjoy one of Horizon West's most sought-after communities. Experience the perfect combination of modern comfort, recent updates, and an outstanding Florida lifestyle. Lawn maintenance is included. Exterior scheduled to be painted!

8150 Red Stopper Lane, Winter Garden
$495,000
3 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
MOVE-IN READY in the highly sought-after Lakeview Pointe community of Horizon West! This beautifully maintained 3-bedroom, 2.5-bath home offers an open-concept floor plan that's perfect for everyday living and entertaining. Start your day with a cup of coffee on the charming front porch while enjoying peaceful conservation views and local wildlife with no front neighbors, or relax in the evening on the private rear porch overlooking a tranquil green space that creates added privacy between the home and detached garage. Inside, you're welcomed by soaring vaulted ceilings, abundant natural light, and tile flooring throughout the main level. The spacious living room flows seamlessly into the open kitchen, featuring granite countertops, a center island, solid wood cabinetry, stainless steel appliances, and ample workspace for the home chef. The adjacent dining area and convenient half bath complete the first floor. Upstairs, you'll find NEW luxury laminate flooring throughout the staircase and second level, adding a fresh, modern touch. The generous primary suite is filled with natural light and features a spacious ensuite bath with dual vanities, a walk-in closet, and a walk-in shower. Two additional bedrooms, a full guest bath, and an upstairs laundry room provide both comfort and convenience. Residents of Lakeview Pointe enjoy exceptional amenities, including scenic walking trails, a resort-style pool, fitness center, playground, fishing pier on Huckleberry Lake, and a Disney fireworks viewing area where you can enjoy spectacular nightly displays. The location is second to none, just minutes from Hamlin Town Center, Starbucks, Walgreens, shopping, restaurants, Horizon West Regional Park and new library opening soon, plus everyday conveniences. Orange County National Golf Center is nearby, and Walt Disney World is approximately 10 minutes away, with Disney Springs just 12 miles from home. Convenient access to SR 429 and other major roadways makes commuting throughout Central Florida effortless.

14230 Murcott Blossom Boulevard, Winter Garden
$459,000
3 Beds ⋅ 3 Baths ⋅ Harvest/Ovation SubDv. ⋅ 34787 Zip Code
***** PRICE REDUCED ***** Rare Dual Owner's Suite Townhome — Priced to Move, Near Disney This 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months out. What sets this home apart is its dual owner's suite layout, a rare find at this price point, with one suite offering a private balcony retreat overlooking the pond, with peaceful water views and nightly glimpses of Magic Kingdom fireworks. Step outside to your own covered patio, a comfortable outdoor living space perfect for everyday relaxation and entertaining. Upgraded flooring and fixtures run throughout, adding a polished, elevated feel without the premium price tag typically attached to that level of finish. Enjoy a community pool and playground, less than 10 minutes from Walt Disney World in one of Central Florida's fastest-growing corridors. With Winter Garden's shopping and dining nearby, this home offers exceptional value for buyers and investors who know the market. This home also includes a transferable 2-10 Pinnacle home warranty (active through May 2027) with zero service history, giving buyers added peace of mind on top of the builder's coverage. Priced competitively for a fast sale. Schedule your showing today.

14014 Scarlet Aster Alley, Winter Garden
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