Winter Garden Homes with Garden Exterior Features

Winter Garden Homes with Garden Exterior Features

Welcome to Winter Garden, Florida—a picturesque city that beautifully blends small-town charm with modern conveniences. Nestled just a stone's throw from Orlando, Winter Garden boasts a rich history that dates back to the late 1800s, evident in its vibrant downtown area filled with quaint shops, delightful eateries, and cultural attractions. The stunning West Orange Trail meanders through the heart of the city, offering residents an idyllic setting for biking, walking, and enjoying the lush Florida landscape.

One of the standout features of homes in Winter Garden is their enchanting garden exterior designs. Many properties showcase meticulously landscaped yards that invite you to unwind and connect with nature right in your own backyard. From vibrant flower beds to serene water features, these gardens create a peaceful oasis for relaxation and entertainment. Imagine hosting summer barbecues or enjoying quiet evenings under the stars, surrounded by the beauty of your garden.

In Winter Garden, homes with garden exterior features often include spacious patios, pergolas, and outdoor kitchens, seamlessly blending indoor and outdoor living. Whether you’re a gardening enthusiast or simply appreciate the aesthetic appeal, these homes offer a unique opportunity to enjoy Florida’s year-round sunshine while enhancing your lifestyle.

With a strong sense of community, excellent schools, and an array of recreational activities, Winter Garden is not just a place to live—it's a place to thrive. Discover your dream home here, where the beauty of garden living meets the warmth of Southern hospitality. Welcome to Winter Garden, where your perfect home awaits!

Newest Winter Garden Homes with Garden Exterior Features

921 Westcliffe Drive, Winter Garden
$570,000
4 Beds ⋅ 3 Baths ⋅ Fullers Lndg B SubDv. ⋅ 34787 Zip Code
Discover the luxury of space in this beautifully maintained former Maronda Homes model, nestled on a cul de sac in Winter Garden. Set on a generous half acre lot with mature trees and custom landscaping, this home offers over 2,354 square feet of living space with four bedrooms, two and a half bathrooms, a dedicated office, and an upstairs bonus loft. A striking two story foyer welcomes you with natural light, while a separate dining room and an office with French doors add elegance and versatility. The spacious living room features custom built in details and flows seamlessly into a kitchen with warm wood cabinetry, stainless steel appliances, a center island, and a water filtration system. Upstairs, the primary suite provides a relaxing retreat with dual sinks, a soaking tub, and a separate shower. Sliding glass doors lead to a backyard patio and an expansive lawn enclosed with vinyl fencing, offering a beautiful setting for outdoor dining, entertaining, and quiet afternoons beneath mature shade trees. Thoughtful improvements include a roof replaced in July 2022, HVAC systems installed in 2022, and a new water heater in 2026. The garage features an 18 SEER air conditioning system installed in 2020 and an epoxy floor completed in 2023. Exterior painting approximately two years ago adds to the home’s cared for appeal. Approximately ten minutes from Plant Street’s charming shops and dining, with convenient access to Walt Disney World and Universal Orlando, this inviting home combines spacious living with the best of the Winter Garden lifestyle.

921 Westcliffe Drive, 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
1349 Castleport Road, Winter Garden
$749,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

1349 Castleport Road, Winter Garden
1539 Hawkesbury Court, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code
Welcome to 1539 Hawkesbury Court, located in the desirable Winter Garden area of Central Florida! This single-family home offers an excellent opportunity to enjoy the convenience, amenities, and lifestyle that make Winter Garden a sought-after place to call home. Conveniently located near shopping centers, restaurants, grocery stores, parks, and everyday essentials, residents can enjoy easy access to a variety of local conveniences. Explore the charm of historic Downtown Winter Garden, known for its unique shops, local restaurants, cafés, and welcoming atmosphere. The popular West Orange Trail is nearby, offering miles of scenic paths for walking, jogging, and cycling. Winter Garden Village provides an array of retail stores, dining options, and entertainment for added convenience. The property's location also offers access to major roadways, including Florida's Turnpike and State Road 429, making travel throughout the greater Orlando area convenient. Enjoy proximity to recreational opportunities, golf courses, and outdoor activities, while remaining within reach of Orlando's employment centers, attractions, and entertainment destinations. Whether you're looking for a place to call home or exploring real estate opportunities in the growing Central Florida market, this property presents an opportunity to enjoy the many benefits of the Winter Garden lifestyle.

1539 Hawkesbury Court, Winter Garden
776 Orange Belt Loop, Winter Garden
$710,000
3 Beds ⋅ 2 Baths ⋅ Heritage/Plant Street SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location is everything in this highly sought-after Golf Cart District of Downtown Winter Garden, where location and lifestyle come together! Situated right off the scenic West Orange Trail, this home places you just moments from the charm, restaurants, shopping, and entertainment of historic Downtown Winter Garden. Best of all, this is a golf-cart-approved area, making it easy to enjoy everything this vibrant community has to offer without getting in the car. From the moment you arrive, you'll appreciate the lush landscaping, paver driveway, and charming front porch. Step inside to a welcoming foyer, with two spacious secondary bedrooms and a full bathroom conveniently located at the front of the home. Continue into the heart of the home, where the open-concept family room, dining area, and stunning gourmet kitchen create the perfect space for everyday living and entertaining. The kitchen features gas cooking, a wall oven, oversized island with sink, abundant upgraded cabinetry extending to the tall ceilings, a spacious walk-in pantry, and a convenient built-in drop zone. The home also offers a separate laundry room complete with washer and dryer and a laundry tub for added convenience. Privately tucked away at the rear of the home, the spacious primary suite provides a peaceful retreat. The spa-inspired primary bathroom features a large glass-enclosed shower, dual-sink vanity, separate water closet, and generous walk-in closet. Step outside to the screened-in lanai, complete with an electric retractable screen wall, creating an ideal setting for relaxing, entertaining, or enjoying Florida's beautiful weather. Additional features include a whole-home water filtration system, adding another level of comfort and convenience. And the location truly sets this home apart. Enjoy easy access to the 35-mile West Orange Trail, while being just minutes from Downtown Winter Garden's award-winning restaurants, charming local shops, Crooked Can Brewery, and the renowned Winter Garden Farmers Market. You'll love the genuine hometown atmosphere and the convenience of being able to experience so much of it by golf cart. With HOA dues that include lawn maintenance, this home offers a low-maintenance lifestyle in one of Winter Garden's most desirable areas. Homes in the Golf Cart District rarely come available and are highly sought after. Don't miss the opportunity to make this exceptional Downtown Winter Garden home your own!

776 Orange Belt Loop, Winter Garden
15601 Dahoon Holly Lane, Winter Garden
$669,990
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c-2e SubDv. ⋅ 34787 Zip Code
CORNER LOT | SUMMERLAKE | PRIMARY SUITE ON FIRST FLOOR | OPEN-CONCEPT FLOOR PLAN | LOFT | DISNEY FIREWORKS VIEW Welcome to this beautiful two-story home located on a desirable corner lot in the highly sought-after Summerlake community in Winter Garden's Horizon West area. Featuring 4 bedrooms, 2.5 bathrooms, a spacious loft, and an open-concept floor plan, this home offers the perfect combination of comfort, functionality, and location. The main floor features a spacious living area with an elegant tray ceiling, seamlessly connected to the kitchen and dining area, creating a bright and welcoming space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a center island, ample cabinetry, and stone countertops. A dedicated and equipped laundry room provides additional convenience. The primary suite is conveniently located on the first floor, offering privacy and easy accessibility. Upstairs, you will find three additional bedrooms, a full bathroom, and a versatile loft, perfect for a second living area, home office, media room, or playroom. Additional features include a two-car garage with rear access and a covered lanai, ideal for relaxing and enjoying Florida's beautiful weather. Thanks to its location, the home also offers the unique opportunity to enjoy Disney fireworks from the property. Residents of Summerlake enjoy an array of resort-style amenities, including a clubhouse, resort-style swimming pool, fitness center, basketball and tennis courts, playgrounds, recreational areas, walking trails, and more. The location is truly exceptional, with convenient access to Hamlin Town Center, where you will find restaurants, shopping, Publix, entertainment, and everyday conveniences. The home also offers easy access to SR-429 and is just minutes from Walt Disney World and Central Florida's world-famous attractions. Don't miss the opportunity to own a corner-lot home with a first-floor primary suite, spacious loft, resort-style community amenities, and an unbeatable Horizon West location. Enjoy the convenience of being close to shopping, dining, entertainment, major highways, and Disney—while having the added bonus of watching Disney fireworks from home. PLEASE NOTE: The home is currently occupied by a tenant, with the current lease through October 31st. For this reason, professional photography was not possible at this time. However, the home is even more beautiful in person than reflected in the current photos. The property was professionally designed and decorated by an interior designer and features numerous upgrades throughout, including carefully selected furnishings, designer finishes, and decorative details that enhance the home's style, comfort, and overall appeal.

15601 Dahoon Holly Lane, Winter Garden
1606 Beulah Road, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ Orange Cove SubDv. ⋅ 34787 Zip Code
LOCATION, LOCATION, LOCATION, Exceptional value is found with this spacious 3 bedroom, 2 bathroom home. You will appreciate the fully remodeled home with new flooring, kitchen cabinets and countertops, hall and master bathrooms, roof, water heater, pluming, and covered porch. This property is located across the street from Winter Garden High School and 5 minutes away from downtown Winter Garden and convenient access to major highways.

1606 Beulah Road, Winter Garden
8091 Bowery Drive, Winter Garden
$585,000
4 Beds ⋅ 3 Baths ⋅ Lake Hancock Preserve SubDv. ⋅ 34787 Zip Code
Discover refined living in this beautifully appointed corner-lot residence in desirable Horizon West. Designed with elegance and everyday comfort in mind, this exceptional home features a spacious open floor plan, split-bedroom design, 4 bedrooms, 3 full baths, and a versatile den. The gourmet kitchen showcases 48-inch cabinetry, a beautiful glass-front display cabinet, and granite countertops, creating a nice space for both everyday living and entertaining. The corner setting provides abundant natural light and enhanced privacy, while the HOA includes lawn maintenance for added convenience. Ideally located near Publix, Walmart, Starbucks, restaurants, cafés, Cinepolis Luxury Cinemas, Urban Air Trampoline Park, and highly rated schools. Convenient access to Hwy 429 and Hwy 535.

8091 Bowery Drive, Winter Garden
14501 Grove Resort Avenue Unit 2608, Winter Garden
$255,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden
1720 Lake Roberts Landing Drive, Winter Garden
$1,399,999
5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code
Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden
13360 Sunny Retreat Lane, Winter Garden
$595,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden
14776 Magnolia Ridge Loop, Winter Garden
$839,900
4 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code
Welcome to your Dream home with a private Pool, located in Orchard Hills Community! This stunning residence perfectly blends elegance, comfort, and functionality in Winter Garden's most sought-after neighborhoods. This home offers 4 bedrooms, 3 full bathrooms, and a 1/2 pool bath bath with a bonus /flex room off of the kitchen and thoughtfully designed living spaces ideal for both everyday living and entertaining. A beautifully appointed gourmet kitchen, complete with a large island, elegant granite countertops, and ample cabinetry. The kitchen seamlessly flows into the expansive open-concept living and dining areas, creating the perfect setting for gatherings with family and friends. A charming front porch welcomes you and provides the perfect place to relax. Step through the sliding glass doors and discover your own private outdoor retreat. The backyard features a spectacular covered gourmet outdoor living area and a beautiful private pool, offering the ideal space for entertaining, relaxing, and enjoying year-round outdoor living. Living in Orchard Hills means enjoying an exceptional lifestyle with resort-style amenities, including a clubhouse, fitness center, resort-style swimming pool, dog park, playgrounds, walking trails, and community events throughout the year. Ideally located, this home is just minutes from Hamlin Town Center, Winter Garden Village, top-rated schools, shopping, dining, grocery stores, and major highways, including SR-429 making this Central Florida residence such a desirable place to live.

14776 Magnolia Ridge Loop, Winter Garden
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