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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

$624,900
4 Beds 3 Baths Hamlin Reserve SubDv. 34787 Zip Code
Discover the allure of modern living in this pristine, like-new (2019 built) single-story home in the coveted Hamlin area of Horizon West, spanning 2,205 square feet of all-concrete construction that beautifully marries sleek design with functional living. From the moment you step into the inviting courtyard, you're welcomed into a space where sophistication meets practicality. The interior features ample closet space with custom shelving, ingeniously balancing maximum storage and style. The heart of the home is a culinary haven, equipped with a gas range and plentiful cabinetry, ensuring delightful cooking adventures. An expansive laundry and mudroom provide a seamless transition from the 2-car, rear-facing garage, showcasing the home's thoughtfully considered layout. Every room is fitted with ceiling fans to maintain a comfortable environment, further enhanced by state-of-the-art fiber optic cable wiring for a fully connected life. The outdoor area includes a screened-in lanai and a sizeable-fenced backyard, perfect for relaxation or social gatherings, with the enchanting Disney fireworks view adding a magical backdrop to evenings. The commitment to a high-quality lifestyle is underscored by minimal HOA fees and access to exclusive amenities like an elegant clubhouse and pool. Its excellent location not only offers swift access to the 429 Highway but is also zoned for Horizon High School, close to Orlando Health Horizon West Hospital, and the upcoming Orlando College of Osteopathic Medicine, ensuring wellness and education needs are easily met. Nestled in a golf-cart-friendly community, it's just a brief ride to the Orange County National Golf Center and Lodge, with leisure, shopping, and scenic walking trails readily accessible. 15777 Tangelo Twist Aly stands as a testament to refined yet practical living, promising an enriching lifestyle in Horizon West for those who value quality and convenience in perfect harmony.

15777 Tangelo Twist Alley, Winter Garden

$2,400,004
5 Beds 4.5 Baths Hickory Hammock SubDv. 34787 Zip Code
BETTER ACT FAST ON THIS ONE-OF-A-KIND, LAKEVIEW HOME IN A POPULAR GATED COMMUNITY! Enjoy nightly sunsets with an incomparable view of the pristine Johns Lake with this luxury two-story home. With a wide range of upgrades and enhancements throughout almost 5,000 square feet of living space, this gorgeous home provides space for everyone in the family including a conversation room with custom woodwork, large dining room and and a spacious family room, all with attractive, dark wood framing and ceiling beams. The open floor plan looks out to the custom, infinity pool and spa with spectacular fire bowls, custom lighting and a phenomenal lake view. Your backyard oasis is perfect for relaxing or entertaining friends with its shellock pavered (heat resistant) lanai, stonework pillars, outdoor fireplace with seating area and high-end outdoor kitchen featuring custom cabinetry, an inviting island bar, flat top and gas grill, dual tap kegerator, refrigerator and ice machine. The backyard retreat also boasts professionally designed landscaping, an outdoor lighting package and your own boat dock equipped with electric, water and two floating jet ski spaces. The gourmet kitchen includes stainless steel appliances, granite countertops, 42-inch cabinets, a custom range hood, subway tile backsplash, walk-in pantry and an oversized waterfall quartz island and plenty of storage. The first floor also features a guest suite complete with full bath. Upstairs you’ll find a large bonus room with wet bar, media room with projector and screen, home office and three additional bedrooms with walk-in closets. The owners suite features a tray ceiling, two walk-in closets and primary bathroom with separate vanities, granite countertops, garden tub and separate shower plus a balcony that stretches along the entire back of the home with an incredible view of the pool and lake. Additional upgrades include luxury vinyl flooring throughout first floor and second floor common areas, pavered driveway and sidewalk, crown moulding throughout, wood paneled ceilings on front and back porch, water softener, three-car tandem garage and recent exterior paint. Hickory Hammock is a gated neighborhood the best of Florida living, a resort-style pool with a multi-function clubhouse, volleyball courts, tennis courts, workout facility, community dock, playground, dog park and a walking trail. Low HOA dues and A schools make this home better than all the rest. Conveniently located to downtown Winter Garden, Fowler's Grove shopping and major highways. This home has it all, better act fast on this truly special home!

16094 Johns Lake Overlook Drive, Winter Garden

$865,000
6 Beds 4 Baths Johns Lake Pointe SubDv. 34787 Zip Code
INCREDIBLE 6-BEDROOM HOME WITH POND VIEW IN A POPULAR WINTER GARDEN COMMUNITY! Imagine relaxing on your Large, Screened Lanai in front of a cozy fire pit, looking out onto a Natural Pond with your community amenities just across the way. That is just the start of what this John Lake Pointe home has to offer. After passing through a manicured exterior, pavered driveway and inviting Front Porch, you are greeted by a 20-foot Vaulted Ceiling that creates an amazing sense of arrival! The popular Kerrville Floor Plan has almost 4,300 square feet of living space, so there’s plenty of room for everyone in your family. And with 6 Large Bedrooms, you’ll have flexibility for a second office, an exercise or craft room - whatever fits your needs. A spacious kitchen features 42-inch cabinets with undercounter lighting, quartz countertops, a stylish backsplash, stainless steel appliances, a large island with seating, pantry and an adjacent dinette area. The First Floor also features a Private Home Office, Guest Bedroom, Full Bathroom, Separate Living and Dining Room and an Open Family Room. Sliding glass doors lead out to your Outdoor Retreat with your Peaceful Pond View - great for relaxing with the family or entertaining friends. Head up the Wooden staircase to the second floor that boasts an Oversized Bonus Room. The Primary Bedroom and Remodeled Bathroom offers plenty of privacy with a garden tub, double vanity, separate shower and an Oversized Custom Closet. The second floor also has a laundry room with Cabinets and Sink as well as 4 secondary bedrooms - all with Walk-In Closets. Additional features include a 3 Car Tandem Garage with Metal Hanging Racks, Lots of Closets throughout home, New Vinyl Flooring, Carpet and Interior Paint. Also, you can SAVE MONEY with Solar Panels that are PAID OFF, giving the homeowners ~$35 electric bills. Johns Lake Pointe community features a Resort-Style Pool and Clubhouse, Workout Facility, Playground, Walking Trails, Tennis Courts and Low HOA Fees. You can enjoy the nature that surrounds this neighborhood with Johns Lake Conservation on one side, Tucker Ranch on the other side and Johns Lake in the back. Located on the North side of Winter Garden conveniently located near popular downtown Winter Garden, West Orange Trail, Winter Garden Village, local schools (Elementary and Middle are walking distance) and within minutes of major highways including 429, 408 and the Florida Turnpike. 30 minutes from Disney, Universal, Sea World and Orlando International Airport. It's Time to Make the Move!

15104 Heron Hideaway Circle, Winter Garden

$2,200,000
4 Beds 3.5 Baths 30 N Park SubDv. 34787 Zip Code
The PARK AVE address says it all!! A RARE OPPORTUNITY to own 1 of only 9 EXCLUSIVE townhomes located in the heart of downtown Winter Garden's bustling shopping district. Unit 76 in the esteemed 30 N Park townhome community offers an exceptional living experience. This CORNER unit boasts almost 3,800 square feet of living space. Its outstanding features include a captivating rooftop terrace designed for entertainment, complete with a pergola, large hot tub, outdoor kitchen, and ample seating. Inside, the home is appointed with 11-foot ceilings on main floor, high end finishes, custom mill work, an elevator, and smart home technology. The kitchen is a standout, with oversized windows providing lots of natural light, a 12-foot island, high-end appliances, wonderful counter space and lots of cabinets for storage. The open floor plan seamlessly connects the kitchen to the dining and living areas. For those needing a private workspace, the home includes an executive office with oversized glass barn doors. Highlights encompass two large balconies to enjoy the Disney fireworks and scenic views of West Orange Trail. The practical amenities include two tankless water heaters, a whole house generator, and an oversized two-car garage. The master retreat offers ample space with lots of natural light, walk-in closet featuring custom built-ins. The resort style bath offers a soaking tub, dual sinks, and an oversized walk-in shower with floor-to-ceiling tile work. Other notable features of this property include large secondary bedrooms, an en-suite bedroom on the first floor conveniently accessible to the elevator. The exceptional designed floor plan elevates this residence, offering luxurious living in a prime downtown location, making it a compelling choice for those seeking a sophisticated LOCK AND LEAVE urban lifestyle in Downtown Winter Garden. There is video surveillance on the property.

76 N Park Avenue, Winter Garden

$3,100,000
7 Beds 6.5 Baths Lakeshore Preserve Ph 4 SubDv. 34787 Zip Code
Discover your dream of luxury living in this unparalleled 6,400-square-foot lakefront masterpiece, boasting dual opulent master suites for unrivaled comfort and elegance. This residence is not just a home; it's a lifestyle retreat in the heart of convenience. Imagine living where every convenience is just a stroll away - top-rated schools, exquisite dining, comprehensive grocery shopping, trendy salons, and world-class shopping. And, with Disney Parks just minutes away, along with effortless access to 429 and Florida's Turnpike, the best of Florida living is at your doorstep. As you step through the grand entrance, prepare to be captivated by the breathtaking 15-foot coffered ceilings and the majestic grand staircase, setting the tone for an abode where every detail is crafted for awe and inspiration. The kitchen emerges as a chef's paradise, with its sprawling quartz island, apron front sink, state-of-the-art double ovens, and a six-burner Kitchen-Aid gas stove complete with a convenient pot filler. This is where culinary dreams come to life. Outside, the enchantment continues with multiple areas designed for the ultimate entertainment experience. Revel in the magic of Disney's fireworks every evening from your private outdoor oasis. Whether it's from the comfort of the 8-person built-in spa, beside the cozy fireplace in the poolside outdoor living room, or amidst the tranquil sounds and sights of the Grotto's waterfall, every moment here promises to be unforgettable. This home, nestled in the prestigious Lakeshore Preserve by Toll Brothers, is a testament to luxury with over $250,000 in bespoke upgrades. From the central vacuum system, the Sonos amplified sound zones, to the theater room with stadium seating and immersive sound, no detail has been overlooked. Enhanced security with an HD camera system and built-in media outlets ensure peace of mind, while extra spray foam insulation in the attic ensures efficiency and comfort. Permanent holiday lights set the scene for celebrations throughout the year, both at the front of the home and in the lanai, adding a touch of magic to every occasion. Included in you HOA fees is full lawn maintenance and 1 Gig of high-speed internet. The Lakeshore Preserve's Clubhouse is an extension of your home, with a state-of-the-art fitness center, sand volleyball court, zero-entry pool, firepit, and party room for hosting memorable events. The vibrant Social Committee keeps the community spirit alive with breakfasts, sunset socials, movie nights, holiday parties, and more. Plus, with canoes and stand-up paddle boards ready for lake adventures, every day is an opportunity for new discoveries. Embrace a life where luxury meets nature, where every day is an adventure, and where your dreams of the perfect home become reality. Welcome to Lakeshore Preserve, where you don't just find a home; you find where you belong.

15522 Shorebird Lane, Winter Garden

$1,000,000
5 Beds 4 Baths Lake Cove Pointe Ph 02 SubDv. 34787 Zip Code
Prepare to be enchanted by this charming family abode nestled in the heart of Downtown Winter Garden! Don't let this chance slip by to reside in a welcoming, golf cart-friendly community. Situated on a serene cul-de-sac within the historic Winter Garden city limits, this exquisite home is situated in the downtown area's sole gated community with two entrances. Upon entering, you'll be captivated by the expansive vaulted ceilings, setting a grand tone for the home. The first floor boasts modern engineered wood flooring flowing seamlessly through the living spaces. The chef's kitchen, upgraded with granite countertops, 42” white shaker cabinets, and stainless steel appliances, exudes sophistication, complemented by a sleek white vent hood and flat cooktop, adding a contemporary flair. Ascending upstairs, a versatile loft area awaits, perfect for a playroom or family media hub. The luxurious master bedroom features custom wainscoting and refined paint finishes, creating an ambiance of elegance and comfort. An additional laundry room and three sizable guest bedrooms round out the second floor. Outside, a spacious screened patio provides an ideal spot for relaxation, while the custom splash pad offers entertainment for family and friends. With ample storage, the three-car garage fulfills all your organizational needs. Seize this golden opportunity to own a piece of one of Central Florida's most coveted and rapidly expanding locales. Conveniently located near major highways, including 408, 429, and the Turnpike, and short distance to the West Orange trail, farmers market, and an array of dining and shopping options, this turnkey family home is sure to attract attention. Don't delay – schedule your private showing today before this gem is gone!

420 Lone Heron Way, Winter Garden

$325,000
2 Beds 2.5 Baths Daniels Landing SubDv. 34787 Zip Code
Welcome to 236 Deepcove Road, a charming 2-bedroom, 2.5-bathroom home nestled in the heart of Winter Garden, FL. This delightful residence offers 1236 square feet of comfortable living space, situated on a 2022-square-foot lot. Step inside to discover a freshly updated interior, featuring brand new paint and carpet throughout. The primary bedroom offers a private en-suite bathroom, while the second bedroom is spacious and bright. Enjoy the convenience of a brand new air conditioning system, complete with a 10-year warranty for the new owners, ensuring comfort and peace of mind for years to come. With a garage for your vehicle and additional storage, this home combines practicality with comfort. Conveniently located just a stone's throw away from Winter Garden Village, Downtown Winter Garden, and I-4 on ramps, this home offers easy access to a plethora of amenities and entertainment options. Whether you're seeking a relaxing day at the village or a quick commute, this location has you covered. Pet-friendly and move-in ready, this home is ideal for those seeking a cozy and low-maintenance lifestyle. The HOA also provides internet, and HBO. This gated community offers everything you're looking for, so don't miss out on the opportunity to make this delightful residence your own. Schedule a showing today and experience the best of Winter Garden living at 236 Deepcove Road.

236 Deepcove Road, Winter Garden

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