Winter Garden Homes with Private Yard Exterior Features

Winter Garden Homes with Private Yard Exterior Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community spirit, Winter Garden beautifully blends the warmth of small-town living with the conveniences of modern life. With its historic downtown area brimming with boutique shops, delightful eateries, and lively farmers' markets, residents enjoy a unique blend of culture and community.

Winter Garden is not just about its quaint streets and friendly faces; it’s also a haven for outdoor enthusiasts. With an abundance of parks, scenic trails, and proximity to the stunning West Orange Trail, adventure awaits right outside your doorstep. Whether you're biking, walking, or simply enjoying a leisurely afternoon, the natural beauty of this area will captivate you.

For those seeking a home that offers privacy and outdoor enjoyment, Winter Garden’s real estate market features a variety of properties with private yard exterior features. Imagine stepping into your own serene oasis, where you can host summer barbecues, cultivate a garden, or simply unwind under the Florida sun. These homes are designed to enhance your lifestyle, providing ample space for outdoor activities while ensuring a peaceful retreat from the hustle and bustle of daily life.

With its friendly community, beautiful scenery, and homes that embrace the outdoors, Winter Garden is not just a place to live; it’s a place to thrive. Explore the charm of this delightful city and discover your dream home with a private yard today!

Newest Winter Garden Homes with Private Yard Exterior Features

8877 Lakeshore Pointe Drive, Winter Garden
$650,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, completely remodeled home in beautiful Winter Garden! Offering 4 spacious bedrooms, 3.5 luxurious bathrooms, and a separate guest house. This exceptional property combines elegance, comfort, and versatility. The home features a gorgeous interior courtyard, creating a beautiful private setting perfect for relaxing or entertaining. Inside, you’ll find soaring ceilings throughout, an elegant and inviting living space, and a chef-inspired kitchen equipped with state-of-the-art appliances and exquisite finishes. The spacious bedrooms include comfort and privacy, while the luxurious primary suite features a spa-inspired bathroom with a beautiful soaking tub, an elegant walk-in shower, and generous closet space. Every detail has been thoughtfully designed to create an elegant yet welcoming atmosphere. With its complete renovation, stunning architectural features, private courtyard, and separate guest residence, this extraordinary Winter Garden home offers a truly special living experience.

8877 Lakeshore Pointe Drive, Winter Garden
8900 Sonoma Coast Drive, Winter Garden
$745,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Enjoy resort-style living in Waterleigh, a master-planned community in Horizon West, Winter Garden. This single-story home offers 3 bedrooms, 2 full bathrooms, a half bathroom, and a separate office, complemented by distinctive interior finishes and expansive outdoor living spaces. An inviting foyer features decorative wood slat accents, integrated lighting, and a floating bench. The open-concept living area showcases a tray ceiling, wood-look tile flooring, and a custom TV feature wall with a floating media console. The kitchen features cabinetry, stone countertops, a tile backsplash, pendant lighting, and a stainless steel appliance package, including a refrigerator, built-in oven, microwave, cooktop, and dishwasher. A separate dining area provides additional gathering space. The office features glass French doors, built-in cabinetry, shelving, and work surfaces. The primary suite includes custom closet organizers and an en-suite bathroom with dual sinks, illuminated mirrors, a separate shower, a soaking tub, and a private water closet. The laundry room includes a washer and dryer, while the garage offers extensive storage cabinetry and a coated floor. Step outside to a covered, screened lanai overlooking an expansive paver patio with a fire pit, fenced backyard, and wooded backdrop—an inviting setting for relaxing or entertaining. Waterleigh offers community pools, clubhouses, fitness facilities, playgrounds, and recreational amenities in a scenic setting of lakes and ponds. Enjoy convenient access to shopping and dining at nearby Hamlin, Publix within the community, historic Downtown Winter Garden, and SR-429. Nearby schools include Atwater Bay Elementary, Water Spring Middle, and Horizon High School; buyers should verify current school assignments with Orange County Public Schools. Kitchen appliances, washer, and dryer are included in the sale. Furnishings shown in the photographs are actual furnishings. Select photographs have been digitally enhanced for lighting, and flames have been digitally added to the outdoor fire pit.

8900 Sonoma Coast Drive, Winter Garden
5567 Cypress Hill Road, Winter Garden
$519,995
3 Beds ⋅ 2 Baths ⋅ Orchard Hills Ph 2 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention lawn service is included in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home has for you.

5567 Cypress Hill Road, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
730 Magnolia Street, Winter Garden
$850,000
5 Beds ⋅ 3 Baths ⋅ Winter Gdn Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 6- panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

730 Magnolia Street, Winter Garden
740 Magnolia Street, Winter Garden
$850,000
5 Beds ⋅ 3 Baths ⋅ Winter Garden Manor SubDv. ⋅ 34787 Zip Code
Virtually Staged. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 8-panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

740 Magnolia Street, Winter Garden
14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a loft area, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden
17361 Bal Harbour Drive, Winter Garden
$689,900
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lk-Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to this spacious 4-bedroom, 2.5-bath home offering approximately 2,931 square feet in the desirable Waterside at Johns Lake community. The open floor plan features a versatile front room ideal for a home office, formal dining room, or additional living space. The kitchen offers granite countertops, stainless-steel appliances, abundant cabinetry, and an open connection to the family room. An additional flex room provides even more space for entertaining, relaxing, or creating a game room. All four bedrooms are located upstairs, including a generous primary suite with a walk-in closet, dual-sink vanity, and walk-in shower. Additional features include an interior laundry room, attached two-car garage, and a covered paver lanai for enjoying the Florida lifestyle. Community amenities include a pool, clubhouse, fitness center, playground, sidewalks, and access to Johns Lake. Conveniently located near shopping, dining, Downtown Winter Garden, Hamlin, and FL-429. New photos coming soon!!!

17361 Bal Harbour Drive, Winter Garden
721 Foster Avenue, Winter Garden
$699,000
7 Beds ⋅ 3 Baths ⋅ Burchshire SubDv. ⋅ 34787 Zip Code
ATTENTION INVESTORS! RARE INCOME-PRODUCING TRIPLEX IN THE HEART OF WINTER GARDEN! Discover an exceptional investment opportunity at 721 Foster Avenue, ideally located just minutes from Historic Downtown Winter Garden and the highly desirable Plant Street district, known for its charming boutiques, popular restaurants, entertainment, and vibrant community atmosphere. Situated on an oversized lot, this partially occupied triplex features three renovated units, each with its own private laundry room, offering added convenience and appeal for tenants. With established tenants already in place, this property provides an opportunity for immediate rental income. Each unit is separately metered for electricity, and the property is connected to city water and sewer. Tenants are responsible for their own utilities and lawn maintenance, helping minimize operating expenses and simplify property management. The spacious lot offers additional possibilities for future improvements or potential expansion, including a garage apartment or in-law suite, subject to zoning, permitting, and applicable building requirements. Whether you're expanding an established real estate portfolio or seeking a multifamily investment in one of Central Florida's most desirable and growing communities, this property offers an attractive combination of location, existing rental income, tenant-friendly amenities, and long-term investment potential. Don't miss this opportunity to own a rare triplex near the heart of Historic Downtown Winter Garden!

721 Foster Avenue, Winter Garden
15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden
725 Tranquil Trail, Winter Garden
$669,000
5 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 02 SubDv. ⋅ 34787 Zip Code
Enjoy the best of Winter Garden living in this inviting pool home, ideally situated in the desirable gated community. Located in a premier area close to shopping, dining, entertainment, and everyday conveniences, this home combines spacious interiors, welcoming curb appeal, and a backyard made for enjoying the Florida lifestyle. A striking exterior, tropical landscaping, and a covered front entry create a memorable first impression. Inside, abundant natural light, soft interior colors, and attractive flooring lend warmth to the main living spaces. The thoughtfully arranged two-story layout offers room to gather, entertain, and unwind, with a welcoming front living area and an open kitchen, dining, and family room that keep the heart of the home connected. The kitchen is a standout, featuring wood cabinetry, stainless steel appliances, recessed lighting, and a generous contrasting island topped with a light countertop. Ample cabinet storage and expansive work surfaces provide both style and practicality, while the adjoining dining area offers a comfortable setting for everything from casual breakfasts to holiday gatherings. Large windows and sliding glass doors brighten the surrounding living spaces and connect the interior to the backyard. Upstairs, a spacious loft adds valuable flexibility to the floor plan. Create a second lounge, media room, play area, or workspace tailored to your needs. The generously sized primary bedroom provides a relaxing retreat with room for a sitting area, while the additional bedrooms give versatility for guests, hobbies, or working from home. Step outside to discover one of the home’s most appealing features: a private backyard retreat with a swimming pool, raised spa, and an expansive paver deck. Spend sunny afternoons poolside, enjoy outdoor dining, or gather with friends beneath the evening sky. Privacy fencing, surrounding greenery, and lawn space complete this inviting setting, bringing together room for recreation and relaxation. This community enhances the lifestyle with gated entry and community amenities that include a swimming pool, playground, sports courts, and a community boat ramp and dock. Beyond the neighborhood, enjoy convenient access to Winter Garden Village’s shopping and restaurants, historic downtown Winter Garden, and major roadways connecting you to Orlando and Central Florida’s attractions. With its bright living spaces, flexible layout, appealing kitchen, and beautiful poolside setting, this home offers an exceptional combination of comfort and convenience in a sought-after Winter Garden location. Schedule your private showing.

725 Tranquil Trail, Winter Garden
234 N Lakeview Avenue, Winter Garden
$2,199,900
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden
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