Winter Garden/Oakland Homes with Private Yard Exterior Features

Winter Garden/Oakland Homes with Private Yard Exterior Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This picturesque area is renowned for its charming small-town atmosphere, vibrant community spirit, and stunning natural landscapes. With its rich history and modern amenities, Winter Garden offers a perfect blend of old-world charm and contemporary living.

As you stroll through the historic downtown, you’ll discover an array of delightful shops, cozy cafes, and local farmers' markets, making it a hub of activity for residents and visitors alike. The scenic West Orange Trail winds through the area, providing ample opportunities for walking, biking, and enjoying the beautiful Florida weather. With lush parks and serene lakes, outdoor enthusiasts will find plenty to explore in this idyllic setting.

When it comes to homes in Winter Garden and Oakland, you’ll find an impressive selection of properties featuring private yards, perfect for families and those who appreciate their outdoor space. These homes often boast beautifully landscaped gardens, spacious patios, and room for recreational activities, making them ideal for entertaining or simply unwinding after a long day. Imagine hosting summer barbecues, playing catch with the kids, or enjoying quiet evenings under the stars in your own private oasis.

Whether you're looking to buy your first home, upgrade your living situation, or invest in a rental property, Winter Garden and Oakland offer a wonderful array of options. With a warm community and a wealth of amenities, it’s no wonder that this charming region is a sought-after destination for homebuyers in Florida. Come and discover your dream home in this delightful corner of Orange County!

Newest Winter Garden/Oakland Homes with Private Yard Exterior Features

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, three full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior cool. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!

16130 Wind View Lane, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to 9225 Holliston Creek Place, an exceptional pool home nestled on a premium corner lot in one of Winter Garden's most sought-after communities. From the moment you arrive, the lush landscaping, side-entry garage, and beautifully maintained exterior set the tone for everything this home has to offer. Step inside and you are immediately greeted by soaring ceilings, an abundance of natural light, and a thoughtfully designed open floor plan that flows seamlessly from the formal living and dining areas into the heart of the home. The spacious kitchen is a true entertainer's dream, featuring generous counter space, ample cabinetry, and a layout that opens directly to the main living area — perfect for gatherings of any size. The dedicated home office is one of the standout features of this property — large, well-appointed, and completely separate from the living spaces, giving you the ideal work-from-home setup or the flexibility to use as a fifth bedroom, playroom, or media room. The primary suite is a private retreat, offering a generous layout, spa-like en suite bathroom with dual vanities, soaking tub, and walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned for privacy. Step outside and discover your own backyard oasis. The screened pool and lanai area is designed for true Florida living — whether you are taking a morning swim, hosting a weekend cookout, or simply unwinding at the end of the day. The summer kitchen is fully equipped and perfectly positioned to make outdoor entertaining effortless, with everything you need just steps from the pool deck. Being on a corner lot provides additional yard space, extra privacy, and enhanced curb appeal that interior lots simply cannot match. Located in a vibrant, well-established Winter Garden community with easy access to top-rated schools, SR-429, the 408, shopping, dining, and all of Central Florida's best attractions — this one truly checks every box.

9225 Holliston Creek Place, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code

WELCOME TO LAKEVIEW POINTE AT HORIZON WEST! This 5-bedroom, 4-full-bath Pulte Creekview floorplan offers a flexible two-story layout with a downstairs primary suite, upstairs loft, flex room, 3-car garage, and a fully fenced corner-lot backyard. Hardwood flooring extends throughout the first floor, complemented by tray ceilings in the foyer and primary suite, plantation shutters, neutral interior paint, and updated lighting in the flex space and breakfast nook. The open kitchen, café, and family room create a central gathering space, featuring 42-inch maple cabinetry with crown molding and hardware, granite countertops, an oversized island with breakfast bar seating, built-in wall oven and microwave, corner walk-in pantry, and extended cabinetry along the breakfast nook for additional storage. Glass sliders with a remote-controlled window treatment open to the covered, extended screened brick-paver patio overlooking the private fenced yard. The downstairs primary suite includes a tray ceiling, oversized walk-in closet, dual-sink granite vanity, glass-enclosed tiled walk-in shower, and private water closet. Three additional bedrooms are located downstairs, including one adjacent to a full bath with dual-sink granite vanity, while two bedrooms share another full bath. Upstairs, a loft, storage room, fifth bedroom with extensive closet space, and a fourth full bath provide versatile space for guests, work, hobbies, or media use. Recent improvements include interior and exterior paint, two new AC systems installed in 2025, ceiling fans, bathroom mirrors, front door hardware, epoxy-finished garage floor, and overhead garage storage racks. Kitchen appliances, washer, and dryer convey. A transferable Choice Home Warranty is included through May 2027, subject to warranty terms. Lakeview Pointe HOA includes lawn care, irrigation, community pool, fitness center, playground, and additional community amenities. Convenient Horizon West location near Hamlin shopping and dining, SR-429, Winter Garden Village, Walt Disney World Resort, and major Central Florida attractions.

7052 Enchanted Lake Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code

Welcome to this exceptional model home in the highly sought-after Hamlin Reserve, one of Winter Garden’s premier communities. Perfectly positioned on a desirable corner homesite, this beautifully designed two-story residence offers the ideal combination of luxury, functionality, and lifestyle. One of the home’s most valuable features is the private detached apartment above the two-car garage, complete with its own full bathroom. This versatile space is perfect as an in-law suite, private guest quarters, home office, fitness studio, or an ideal retreat for extended family and visitors—allowing everyone to enjoy their own space while preserving the privacy of the main residence. Inside the main home, you’ll find elegant hardwood flooring throughout the main living areas, custom built-in cabinetry in the family room, and a luxurious primary suite designed for comfort and relaxation. The chef-inspired kitchen showcases 42” painted linen upper cabinetry with espresso maple lower cabinets, an oversized quartz island with pendant lighting, designer tile backsplash, quartz countertops, and premium stainless steel gas appliances, creating the perfect space for everyday living and entertaining. Step outside to your private backyard oasis featuring a covered lanai, fenced yard, and sparkling pool—ideal for enjoying Florida’s year-round outdoor lifestyle. Residents of Hamlin Reserve enjoy outstanding community amenities including a private clubhouse, resort-style pool, walking trails, parks, open green spaces, and a dog park. Located in the heart of Winter Garden, consistently recognized as one of the most desirable places to live in the Orlando area, this home offers access to top-rated schools, exceptional restaurants, shopping, entertainment, and the vibrant Hamlin Town Center. Just minutes from Walt Disney World, major highways, and Orlando’s world-class attractions, this location offers the perfect balance of convenience, recreation, and community living. This is more than a home—it’s a lifestyle opportunity. Schedule your private showing today.

15367 Shonan Gold Drive, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code

Privacy is a rare find in the highly sought-after Hamlin area of Winter Garden, and this move-in ready 4-bedroom, 2-bath home delivers just that. With no rear neighbors and only one adjacent neighbor, you'll enjoy peaceful sunset views from the fully fenced backyard while being just minutes from Hamlin Town Center, Horizon West, top-rated schools, SR 429, shopping, dining, and Walt Disney World Resort.Inside, luxury vinyl plank flooring flows throughout the home, complemented by custom plantation shutters, recessed lighting, and an elegant tray ceiling in the Owner's Suite that adds warmth and architectural character. The well-appointed kitchen is designed for everyday living and effortless entertaining, featuring quartz countertops, a gas range, stainless steel appliances, a tile backsplash, and a reverse osmosis drinking water system. Additional upgrades include double-pane Low-E windows and sliding glass doors, a tankless water heater, and a programmable smart irrigation system for added comfort, efficiency, and convenience.Designed for year-round Florida living, the inviting front porch, covered lanai, and fully fenced backyard provide the perfect setting to entertain guests, relax with family, or simply unwind while taking in breathtaking Florida sunsets. With no rear neighbors, you'll appreciate the added sense of privacy that's becoming increasingly difficult to find in Horizon West.Ideally located in the heart of Hamlin and Horizon West, you'll be minutes from Hamlin Town Center, Publix, local restaurants, boutique shopping, Cinépolis Luxury Cinemas, Orange County National Golf Center, scenic parks and trails, Winter Garden Village, Historic Downtown Winter Garden, Flamingo Crossings, Walt Disney World Resort, and major commuter routes including SR 429.Offering an exceptional combination of privacy, modern upgrades, energy-efficient features, and one of Central Florida's most desirable locations, this Winter Garden home truly captures the best of Florida living. Schedule your private showing today and experience everything this exceptional property has to offer.

15395 Sugar Citrus Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 5-bedroom, 3-bath home with a dedicated office, offering the perfect blend of elegance, comfort, and functionality in the highly desirable Overlook at Hamlin community of Winter Garden. Thoughtfully designed for today's lifestyle, this spacious floor plan features a sought-after first-floor primary suite, providing a private retreat with convenience and flexibility. From the moment you enter, you'll appreciate the pride of ownership evident throughout. Gorgeous wood flooring flows through the main living areas, complemented by brand-new carpet and fresh interior paint for a truly move-in-ready feel. The dedicated office is ideal for working from home, studying, or creating a quiet flex space. The heart of the home is the open-concept living area, where a beautiful gas fireplace creates a warm and inviting focal point. The spacious kitchen overlooks the family room and dining area, making it easy to entertain while staying connected with family and guests. Step outside to one of the home's standout features—an oversized covered lanai and an expansive screened enclosure that extends your living space outdoors. Whether you're enjoying your morning coffee, dining al fresco, or hosting gatherings, this incredible outdoor retreat is designed for year-round Florida living. Upstairs, you'll find generously sized secondary bedrooms that provide plenty of space for family and guests, while the thoughtful layout offers privacy and versatility for every stage of life. Located in the sought-after Hamlin area, residents enjoy exceptional resort-style amenities, including a private community boat ramp with access to Lake Hancock, a lakeside clubhouse, fitness center, community pool, playgrounds, parks, walking trails, and waterfront recreation. Just minutes from Hamlin Town Center, Walt Disney World, shopping, dining, entertainment, top-rated schools, and major highways, this location offers unmatched convenience and an exceptional lifestyle. With fresh interior paint, gorgeous wood floors, new carpet, a first-floor primary suite, dedicated office, gas fireplace, and an incredible screened outdoor living space, this meticulously maintained home is truly move-in ready and offers everything today's buyers are looking for.

7773 Minutemen Loop, Winter Garden

6 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 34787 Zip Code

TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home.

16945 W Phil C Peters Road, Winter Garden

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