Start your Winter Garden Home Search

Winter Garden is a bustling urban town with over 38,000 residents. It is almost the home of several schools, like Lake Whitney Elementary School, Bridgewater Middle School, and West Orange High School. Only 30 minutes out of Orlando, the town is the perfect distance from the city for commuters.

Community and Events

Winter Garden bolsters its sense of community with a plethora of events, especially around the holidays. For example, in December, they proudly present a number of activities for families to attend: light shows, hayrides, movie nights, a parade, musical performances, and some Santa Clause sightings of course! Some year-round events include live performances every Friday at the Plaza in Downtown Winter Garden and their weekly Farmers Market. If you're looking for things to do inside, Winter Garden provides several options. Their Heritage Museum delves into the town's past with over 5,000 artifacts to look through. The Central Florida Railroad Museum explores the role of the railroad in Florida's past -- a fun history lesson for people of all ages. The Winter Garden's Art Association's community center offers a neat gallery with exhibits and workshops for all. When you need to check out a book, make sure to visit the Winter Garden Branch of the Orange County Library System. Go to the Garden Theatre for a wonderful performance for a night out.

See more Winter Garden Events on their website!

Brand Winter Garden Listings

$465,000
3 Beds 2.5 Baths Storey Grove Ph 2 SubDv. 34787 Zip Code
Discover this beautifully upgraded 3-bedroom, 2.5-bath townhome, partially furnished and ideally situated right in front of the clubhouse. Perfectly located near Disney, dining, shopping, and just minutes away from brand-new A-rated elementary schools, feeding into top-rated districts. Step inside the open-concept living and dining areas that seamlessly flow into a fully equipped kitchen, featuring 42-inch cabinets with elegant crown molding, brand-new stainless steel appliances, a built-in microwave, extractor hood, quartz countertops, subway tile backsplash, and a large island with breakfast bar and extra storage. Additional upgrades include ceiling fans, laundry cabinets, and more. Outside, you’ll love the oversized, fully-paved courtyard, complete with enclosed vinyl fencing, artificial grass, a charming gazebo, and outdoor furniture – perfect for entertaining family and friends. Just beyond the courtyard is the detached two-car garage, equipped with epoxy flooring, extra refrigerator, freezer, office furniture, and storage shelves. Upstairs, enjoy the comfort of two spacious bedrooms and a full bath, along with the master suite, which boasts a double vanity with quartz countertops, a walk-in shower, and plenty of closet space. The home also features new laminate flooring throughout, a laundry room with a brand-new washer and dryer, blinds installed throughout, a Honeywell WiFi thermostat, and a Ring doorbell for added convenience and security. Storey Grove offers a fantastic array of amenities, including a resort-style pool, fitness center, playground, basketball court, and a neighborhood clubhouse. Plus, you’re just moments from the new Publix Shopping Plaza. This home is currently rented at $2,850 per month until August 31, 2025, providing a great investment opportunity. Don’t miss your chance to own this remarkable townhome in one of Winter Garden’s most desirable communities!

14029 Title Way, Winter Garden

$1,375,000
4 Beds 3.5 Baths Independence SubDv. 34787 Zip Code
LAKEFRONT residence in Winter Garden - Natural Lake- **Build your own BOAT DOCK** Located at the coveted Signature Lakes Subdivision of Independence. Do not miss Disney's FIREWORK every night. This stunning home boasts 4 bedrooms, 3 1/2 bathrooms, a BONUS room, and a versatile FLEX ROOM/OFFICE. The open kitchen showcases quartz countertops, stainless steel appliances, a 5-burner gas cooktop, ample cabinets, and an oversized island. NO CARPET– ceramic tile graces the bathrooms and kitchen, while ENGINEERED WOOD FLOORING extends throughout the rest of the home. The spacious DOWNSTAIRS master bedroom features a large custom walk-in closet. Enjoy the convenience of a water softener system and pest control system. 3-car garage. Step onto the pavered and enclosed deck overlooking LAKE SPEER for delightful outdoor dining with tremendous LAKE and SUNSET views. Experience the luxury of watching Disney fireworks from your backyard. Bring your boat, skis, fishing rod, jet skis, and kayaks to utilize the PRIVATE COMMUNITY BOAT RAMP. The low monthly HOA fee covers cable and internet services. The community offers a wealth of amenities, including park areas, green space, wooded conservation, walking/biking paths, 2 pools, 2 clubhouses, fitness facilities, billiards room, arcade, play areas, a large community park, dog parks, tennis and basketball courts. Exceptional school district. A short drive to the new Hamlin, and easy access to SR 429. Close to restaurants, shopping centers and stores. Make this dream home a must-see. Call to schedule your private showing.

14906 Speer Lake Drive, Winter Garden

$575,000
4 Beds 3.5 Baths Waterside/Johns Lake Ph 2c SubDv. 34787 Zip Code
BRING YOUR OFFERS! Listed under appraised value! This amazing home sits on the BEST CORNER LOT in the exclusive Waterside at Johns Lake community. The back of this property faces a beautiful view of a conservation area, so NO REAR NEIGHBORS! It consists of 4 bedrooms, 3.5 baths on an open floor plan. Find yourself just 20 minutes away from Disney, Universal and other main attractions! Also, it is conveniently close to the historic downtown district, great dining, shops, A+ schools: Hamlin Elementary and Hamlin Middle. It was built 2 years ago, so it's ALMOST NEW! The home features a spacious master bedroom on the first floor with en-suite master bath, a walk-in closet and a double vanity with quartz countertops. Prepare dinner in a gourmet kitchen with an island/breakfast bar that overlooks the great room perfect for entertaining guests. It includes wood cabinets, stainless steel appliances and quartz countertops. There is a half-bath downstairs for the convenience of guests. Upstairs, you will find a generous loft which could be used as a play area or additional living space, as well as 3 bedrooms and 2 full bathrooms providing privacy to all the family members. Enjoy daily sunrises and sunsets while sitting in the screened lanai next to the fenced in patio. There is a 2-car garage and a nice, paved driveway with space for 2 additional autos. The right side has an open patio which could also be fenced. Enjoy a short walk to John's Lake with a fishing dock and playground plus amenities as a resort style pool, clubhouse and state of the art fitness center for a low HOA of $196 monthly. No CDD. This very well-maintained home is ready to move in!

1455 Viscaya Cove Boulevard, Winter Garden

$925,000
5 Beds 4.5 Baths Winding Bay Ph 1b SubDv. 34787 Zip Code
Experience Luxurious Living in Winter Garden's Premier Community! Welcome to your dream home in one of Winter Garden’s most desirable neighborhoods. This exquisite Tompkins II model showcases a perfect blend of modern elegance and functional design, offering 3,267 square feet of beautifully curated living space. With its impressive 10-foot ceilings and open-concept layout, this home is designed for both comfortable everyday living and entertaining. The gourmet kitchen, equipped with 42" cabinets and pristine quartz countertops, is sure to delight any home chef. Natural light floods the living areas through expansive 9-foot sliding glass doors, leading to a spacious lanai—perfect for outdoor dining, relaxation, or hosting gatherings. Upstairs, the versatile loft area, additional bedroom, and full bath create a private retreat for guests or family. The home’s sleek Delorean gray tile flooring throughout the house combines modern aesthetics with low-maintenance living. House is equipped with solar panels and a water purifier. Located in a top-rated school district and just 15 minutes from the bustling Hamlin area, which boasts premier shopping, dining, and entertainment, this home offers unparalleled convenience. The community itself is equipped with resort-style amenities, including a sparkling pool, oversized cabana, multi-purpose sports fields, a playground, and a dog park—everything you need for an active and fulfilling lifestyle. Don’t miss the chance to call this exceptional property your own.

15432 Gilligan Court, Winter Garden

$625,000
4 Beds 3.5 Baths Waterleigh Ph 3b 3c & 3d SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to your perfect slice of paradise in the heart of Florida! This stunning, fully furnished 4-bedroom, 3.5-bathroom home complete with a 2-car garage is an exceptional find, ideal for first-time homebuyers, savvy investors, or anyone looking for a move-in ready gem! As you enter, you’ll find a guest bedroom with its own bathroom, along with a convenient half bath for visitors. The spacious, open-concept kitchen is a chef’s dream, complete with stainless steel appliances, a walk-in pantry, and plenty of counter space. The adjacent living room is ideal for entertaining or relaxing, and the dining area, featuring a beautiful oversized table that seats 8-10, is perfect for hosting memorable gatherings with family and friends! Upstairs, the primary master suite is a true retreat, boasting a generous walk-in closet, a luxurious bathroom with double sinks, and extra linen storage, two bedrooms, and second full bathroom. In addition, you’ll find a versatile loft space that can be transformed into a play area, movie room, or even a home office. This home is packed with high-quality upgrades, including gutters, a fenced yard for added privacy, a stylish front glass door, upgraded kitchen faucet, modern bright lighting throughout, and a state-of-the-art security camera system. Plus, the carpets have been freshly cleaned, making this home move-in ready. With the option to purchase the home fully furnished, all you need to do is bring your suitcase! This community offers a vibrant, golf cart-friendly community with resort-style amenities! You’ll have access to multiple pools, a gym, tennis courts, volleyball, playgrounds, and more. Convenience is key, with a Publix supermarket right at the entrance of the community, perfect for quick grocery runs. You’ll also be just minutes away from Orlando’s world-renowned theme parks, making this location ideal for both everyday living and weekend fun! The surrounding area is a shopper’s paradise, with plenty of retail options and fantastic dining spots for foodies. Plus, you’re only a short drive from downtown Winter Garden, where you can explore even more entertainment, historical sites, and culinary delights! Don’t miss this incredible opportunity to own a beautiful, fully furnished home in a prime Florida location. Contact us today to schedule your private showing and start living the dream! Your Perfectly Furnished Florida Home Awaits YOU!

16892 Oakboro Street, Winter Garden

$1,489,741
5 Beds 3.5 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the North Haven. This two-story Emerald Series home contains elevated designs, elegant exteriors and high-end features. The spacious all concrete block construction home features 5 bedrooms, 3.5 baths, flex space and a game room. A beautiful porch welcomes you, as you enter the foyer, you’ll find a flex room perfect for work or play and a powder room. The well-appointed kitchen overlooks the living area, a second dining room, and outdoor lanai. This gourmet kitchen features a Quartz countertops stainless steel appliances, spacious pantry and crown molding cabinetry. Off the kitchen, you’ll find the laundry room with optional drop area entering from the garage. Bedroom one is located at the back of the home for privacy. The bedroom one-bathroom impresses with separated vanities, toilet room with privacy door and spacious walk in closet. Customize bathroom one to meet your dream home goals. As we head up to the second floor, we are greeted with a game area and four bedrooms. Two bedrooms share a second upstairs bathroom and linen closet for extra storage. The additional two bedrooms share an ensuite bathroom and separate vanities for each room. Like all homes in Waterleigh, the North Haven includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

10093 Atwater Bay Drive, Winter Garden

$1,701,786
4 Beds 3.5 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Westbrook. This two-story Emerald Series home contains elevated designs, elegant exteriors and high-end features. The spacious all concrete block construction home features 4 bedrooms, 4 baths, a study, a game room, and a media room. A beautiful entry way welcomes you, as you enter the foyer, you’ll find a formal dining room. As you continue, you are greeted by an open floorplan living area. The well-appointed kitchen overlooks the living room, a second casual dining area, and an oversized outdoor lanai. This gourmet kitchen features Quartz countertops, stainless steel appliances, a spacious pantry, and crown molding cabinetry. Off the kitchen, you’ll find the drop room entering from the 2-car garage as well as a bathroom. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with a double vanity, toilet room with privacy door, separate shower and tub space, and two spacious walk-in closets. As you head towards the stairs, there is a storage room and laundry room for easy access as well as a study room off the 1-car garage. As we head up to the second floor, we are greeted with a game room. Off the game room, is a spacious media room connected to a large, covered patio. Down the hallway, you are greeted with a linen closet, bedroom, and bathroom. Two additional bedrooms share a second upstairs bathroom with separate vanities and a walk-in closet. Like all homes in Waterleigh, the Westbrook includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

10087 Atwater Bay Drive, Winter Garden

$980,000
5 Beds 4 Baths Winding Bay Ph 3 SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. BACK ON THE MARKET!!!!!!! Welcome home to the Frost model in Winding Bay. A spacious and elegant design, this home includes 5 bedrooms, 4 full bathrooms, a study, 2-car garage with a bonus room, and office on the second floor. As you enter the home, you will stand right in the foyer, a guest bedroom and full bathroom on the right. Then you are greeted by a large open concept space. There is a den on the right that can be used as a formal dining room, or an office. The kitchen is a chef’s paradise, there is ample countertops and cabinet storage with a full walk-in pantry. Stainless steel appliances in the gourmet kitchen set off an informal dining space with a large island, and clear sight line into the great room. There is maximum space for entertaining and family gatherings, the great room is backed by a huge sliding glass doors that lead to a covered lanai and pool. The master suite is fit for any king bed. The master bathroom offers dual sinks, an enclosed walk-in shower space, a separate toilet area, and a massive optional extended walk-in closet. Walking up the stairs to the second floor, you will step right into a spacious loft area perfect for a bonus area that is perfect for a growing family to relax, this space also has a built-in pocket office with 2 desk spaces and upper/lower cabinets. There is also 3 bedrooms with walk in closets. There is a full bathroom with dual sinks. One of the bedrooms has his own on full bathroom. The design selections for this stunning floor plan include luxury vinyl plank flooring throughout. Wellborn cabinetry with soft close upper and lower cabinets throughout, as well as Quartz countertops throughout to add elegance! Enjoy serene views of the pool from the covered, screened-in lanai—your private retreat for relaxation and entertainment. Featuring easy-maintenance landscaping with an included irrigation system, a 2-car garage with an Epoxy floor. The home is prewired for a security, and entertainment systems. The home is also equipped with a ring doorbell camera, and keyless door lock. The salt pool and spa are fully automated, with a self-cleaning system, and gas heater. This system is controlled using your smartphone whether you are home or away. ? In addition, this home is conveniently located near Disney world, and Orlando Do not miss this incredible opportunity—this home will not last long on the market! Schedule you are showing today!

14955 Lebeau Loop, Winter Garden

$1,200,000
4 Beds 3 Baths Oakland Park SubDv. 34787 Zip Code
Experience the perfect blend of comfort and elegance in this stunning 4-bedroom, 3-bath, two-story home nestled in the sought-after Oakland Park community! With an inviting open floor plan, this home greets you with a spacious front porch, perfect for enjoying the outdoors. The gourmet kitchen boasts a generous island, ideal for hosting and entertaining. The dining room seamlessly flows into a screened-in side porch, providing peaceful views of the adjacent park. The main-floor primary bedroom features a luxurious ensuite bath with a walk-in shower, garden tub, and a large walk-in closet. A second bedroom with an ensuite bath is also on the first floor. Upstairs, two bedrooms are connected by a convenient Jack and Jill bathroom, offering both privacy and functionality. Additional highlights include a cozy den, elegant crown molding, and tray ceilings. The 3-car garage, with its finished floor, full stand-up attic with electric lift, rear alley access, and adjoining mud room, adds even more convenience. Mature fruit-bearing trees in the yard. The West Orange Trail runs through Oakland Park and is just minutes from downtown Winter Garden by Golf Cart. you'll enjoy easy access to shops, restaurants, a weekly farmer's market, and year-round community events. Enjoy all the amenities this exceptional home offers, including a community pool, multiple parks, and a charming neighborhood ambiance!

931 Landrum Drive, Winter Garden

$1,100,000
5 Beds 4.5 Baths Highlands/Summerlake Grvs Ph 1 SubDv. 34787 Zip Code
Welcome to your dream home in the highly sought-after Summerlake community! This exquisite 5-bedroom, 4.5-bathroom residence boasts an open floor plan that seamlessly blends modern luxury with family-friendly functionality. Step inside to discover an inviting, spacious living area featuring stunning updated flooring throughout. The heart of the home is the chef’s dream kitchen, elegantly appointed with sleek countertops, state-of-the-art appliances, and ample cabinetry. Whether you’re preparing a quick breakfast or hosting a grand dinner party, this kitchen is sure to impress. The primary suite, located upstairs, is a true retreat. Enjoy your private balcony with sweeping views of the picturesque surroundings and nightly Disney fireworks—an enchanting display that adds a magical touch to your evenings. The luxurious en-suite bathroom offers a spa-like experience with its modern fixtures and finishes. Each additional bedroom is thoughtfully designed to provide comfort and privacy, with ample closet space and stylish updates. The four and a half bathrooms are equally impressive, featuring contemporary designs and high-quality materials. Outside, the property is equally spectacular. The expansive pool area is perfect for relaxing or entertaining, offering the perfect vantage point to enjoy the dazzling nightly fireworks. The lush landscaping and outdoor living space make it ideal for hosting summer barbecues or unwinding after a long day. Located in the vibrant Summerlake community, this home offers easy access to local amenities, top-rated schools, and major roadways, all while providing a tranquil retreat from the hustle and bustle. Don’t miss the opportunity to own this exceptional home where luxury, comfort, and magic come together. Schedule your private tour today and experience the enchantment for yourself!

15485 Sweet Orange Avenue, Winter Garden

Start Your Search