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 rich history, vibrant community, and stunning natural beauty, this area has become a sought-after destination for families and individuals alike. With its charming downtown area filled with quaint shops, delightful eateries, and a lively farmers market, Winter Garden offers a perfect blend of small-town charm and modern convenience.

One of the standout features of homes in this picturesque region is their captivating courtyard exterior designs. These thoughtfully crafted homes often boast private courtyards that create a serene oasis for relaxation and entertainment. Imagine stepping out of your living room into a beautifully landscaped courtyard, where you can enjoy morning coffee surrounded by lush greenery or host evening gatherings under the stars. The courtyard not only enhances the aesthetic appeal of the home but also fosters a sense of community and connection with neighbors.

In addition to the stunning architecture, Winter Garden and Oakland are surrounded by scenic parks and recreational opportunities. With easy access to hiking trails, lakes, and golf courses, outdoor enthusiasts will find plenty to explore. The area is also conveniently located near major highways, providing quick access to the vibrant city of Orlando and its world-renowned attractions.

Whether you’re seeking a cozy family home or a luxurious retreat, Winter Garden and Oakland offer a unique living experience that combines the tranquility of suburban life with the excitement of urban amenities. Discover your dream home with a charming courtyard today, and embrace the idyllic lifestyle that awaits you in this beautiful corner of Florida!

Newest Winter Garden/Oakland Homes with Courtyard Exterior Features

$519,995
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
$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
$319,000
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
$429,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Virtually Staged. OBTAINABLE 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
$499,000
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
$316,000
2 Beds ⋅ 3 Baths ⋅ Daniels Landing SubDv. ⋅ 34787 Zip Code
Discover the charm of Daniel’s Landing, a highly desired gated Winter Garden community where convenience meets comfort. Inside, this beautifully upgraded townhome offers two generous primary bedrooms, each with its own bathroom and walk-in closet, ideal for privacy and comfort. The open main floor layout along with a convenient half bath creates a welcoming space for gathering, while the modern kitchen shines with granite counters and stainless-steel appliances. Step outside to your fenced private patio, perfect for relaxing or entertaining. The home also includes a garage with a private driveway. Smart home features like a Ring doorbell and Nest thermostat adds convenience. The HOA covers cable and internet! Spend your days enjoying the incredible amenities such as clubhouse, park, fitness center, peaceful walking trail, and refreshing pool. You’ll also be just moments from the Winter Garden Village and the vibrant downtown area filled with local shops, restaurants, and the beloved farmer's market. Commuting is easy with quick access to 429, the Florida Turnpike, and major attractions including Disney and Universal. ***Licensee Disclosure: Seller is a real estate licensee.*** Buyer or buyer's agent to verify all room dimensions and HOA information.

13349 Harbor Shore Lane, Winter Garden
$400,000
3 Beds ⋅ 3 Baths ⋅ Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Discover this **stunning and meticulously maintained** 3-bedroom, 2.5-bath home, presented in **excellent condition**. The interior has been **freshly painted**, featuring **granite countertops** in both the kitchen and bathrooms. The kitchen is equipped with **stainless steel appliances**, a **spacious island**, a large breakfast bar, and an inviting eat-in area. Enjoy **new flooring throughout the downstairs** in this lovely home. The **generous primary bedroom** is located upstairs and includes an ensuite bath with dual sinks, a roomy shower, and a walk-in closet. The secondary bedrooms are thoughtfully arranged in a **split plan**, ensuring privacy from the primary suite. Convenience continues with a downstairs laundry room featuring hookups. Step outside to a **private, expansive paved lanai**, perfect for entertaining, barbecuing, or relaxing. A large **green space** is just off the front porch. Located just 10 minutes from Disney property, this home is close to all parks, restaurants, shopping, and entertainment. Hamlin Town Center is only a few miles away, and **Orange County National**, the largest golf course in Florida, is nearby. The community offers **resort-style amenities** just steps away, including a pool, two parks, a dog park, pickleball courts, green spaces, and tennis facilities. Enjoy low-maintenance living with the HOA covering exterior upkeep, including roof care, yard maintenance, exterior painting, and lawn care. This home is situated in a **top-rated school district** and boasts a **superb location** with ample parking. Townhomes in this **highly sought-after community** rarely become available. This property is **move-in ready** for its new owners! All info should be verified.

8019 Jeremy Joseph Alley, Winter Garden
$2,190,000
5 Beds ⋅ 5 Baths ⋅ Boyd-Lutz Sub SubDv. ⋅ 34787 Zip Code
Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Custom built pool renderings and pricing available. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. Craftsmanship, luxury, and location—now at an even more compelling price.

20 W Crest Avenue, Winter Garden
$325,000
2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained unfurnished 2-story townhouse located in the gated community of Daniels Landing. Surrounded by attractive landscaping, this charming 2-bedroom, 3-bath home offers a spacious and functional layout designed for comfortable living. Step inside to find a freshly repainted interior, high ceilings, laminate flooring, and an open-concept floor plan that seamlessly connects the combined living and dining areas, creating an inviting space for both relaxing and entertaining. The kitchen is equipped with stainless steel appliances and offers ample cabinet and counter space for everyday convenience. Upstairs, the spacious primary suite features a private ensuite bath, providing a peaceful retreat at the end of the day. Additional highlights include a 2-car garage and a private enclosed courtyard with vinyl fencing—perfect for outdoor dining, entertaining, or enjoying your own quiet outdoor space. Located in the desirable gated community of Daniels Landing, this home combines comfort, style, and convenience in one exceptional property.

13232 Daniels Landing Circle, Winter Garden
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