Winter Garden Homes with Boatable Water Water Frontage

Winter Garden Homes with Boatable Water Water Frontage

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County, where the beauty of nature meets the vibrancy of community living. Known for its picturesque landscapes and rich history, Winter Garden offers a unique blend of small-town charm and modern amenities, making it an ideal place to call home.

One of the standout features of Winter Garden is its stunning waterfront properties. Imagine waking up to the serene views of glistening waters right from your backyard. Homes with boatable water frontage are a true treasure in this area, providing residents with direct access to a variety of water activities. Whether you’re an avid boater, fisherman, or simply enjoy the tranquility of waterfront living, these homes offer the perfect lifestyle.

The city's extensive network of lakes and canals not only enhances the beauty of the landscape but also creates a vibrant community of water enthusiasts. Spend your weekends cruising the waterways, hosting family gatherings by the water, or simply enjoying the breathtaking sunsets that paint the sky in hues of orange and pink.

In addition to its waterfront allure, Winter Garden boasts a lively downtown area filled with quaint shops, delightful eateries, and cultural events. The West Orange Trail, a favorite among locals, winds through the city, offering miles of scenic paths for biking, walking, and jogging.

With its inviting atmosphere and exceptional quality of life, Winter Garden is more than just a place to live; it’s a community where memories are made. Explore the possibilities of waterfront living in this enchanting Florida city and discover your dream home today!

Newest Winter Garden Homes with Boatable Water Water Frontage

14501 Grove Resort Avenue Unit 3636, Winter Garden
$175,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to effortless resort living and an incredible SHORT-TERM RENTAL OPPORTUNITY at The Grove Resort & Water Park! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2-bath condo-hotel is TURNKEY READY and already part of the resort’s rental pool with onsite management, making ownership especially convenient. Owners are permitted PERSONAL USE for up to 179 days per year, offering the flexibility to enjoy the property yourself while also taking advantage of its VACATION-RENTAL POTENTIAL. Set within the GATED RESORT COMMUNITY, this condo is located in a high-rise building with ELEVATOR ACCESS and puts an incredible array of amenities right outside your door. Step inside to find a bright, inviting interior with LUXURY VINYL PLANK FLOORING throughout the main living areas. The open Kitchen features QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES and a convenient breakfast bar, all overlooking the spacious Living Room with plenty of room for a Dining Area. Sliding glass doors extend the living space outdoors to a SCREENED, COVERED BALCONY, creating a relaxing spot to enjoy your morning coffee or unwind after a day at the parks. The AC WAS UPDATED in 2017, adding to the home's appeal as a well-maintained vacation property.The SPLIT-BEDROOM FLOOR PLAN provides privacy for owners and guests alike. The generous PRIMARY SUITE features a walk-in closet, an en suite Bath, and a COMFORTABLE SITTING AREA with its own PRIVATE ACCESS to the balcony. The en suite Bath offers dual sinks with QUARTZ COUNTERTOPS, a garden tub, step-in shower and private water closet. On the opposite side of the condo, the spacious SECOND BEDROOM offers a walk-in closet and its own EN SUITE BATH. A dedicated Laundry Room with washer and dryer adds everyday convenience.The Grove Resort & Water Park is a 106-acre destination with an IMPRESSIVE COLLECTION OF AMENITIES, including SURFARI WATER PARK, featuring a 695-foot lazy river, dual water slides, a FlowRider surf simulator, kids' activity pool and ZERO-ENTRY POOL. The resort also offers MULTIPLE POOLS including the lakefront Springs Pools with three full-size pools, hot tub and children's splash area, along with a 24-hour FITNESS CENTER, restaurants, family activities, LAKE AUSTIN ACCESS and more. CABLE AND INTERNET are also included, while resort transportation provides SHUTTLE SERVICE to Walt Disney World, Universal Orlando and SeaWorld. Lake Austin provides another way to enjoy the outdoors, with a LAKESIDE PIER offering beautiful nature views, catch-and-release fishing and resort watersports. When it is time to venture out, the resort is just SIX MILES FROM WALT DISNEY WORLD, putting Orlando's WORLD-FAMOUS ATTRACTIONS within easy reach. Beyond the resort, enjoy the growing Horizon West area with FLAMINGO CROSSINGS TOWN CENTER, Historic Downtown Winter Garden, the West Orange Trail and Plant Street offering opportunities for dining, shopping, entertainment and enjoying the FLORIDA LIFESTYLE. Families will appreciate the access to A-RATED SCHOOLS, including WATER SPRING ELEMENTARY, WATER SPRING MIDDLE and HORIZON HIGH SCHOOL.Whether you're looking for a vacation home, a personal getaway or a TURNKEY SHORT-TERM RENTAL INVESTMENT, this furnished Grove Resort condo provides an EXCEPTIONAL OPPORTUNITY to own a piece of the Orlando vacation lifestyle—with onsite management, RESORT AMENITIES, and the flexibility to enjoy it yourself. Come discover the possibilities at The Grove!

14501 Grove Resort Avenue Unit 3636, Winter Garden

261 Zachary Wade Street, Winter Garden
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Few homes make an entrance like this one: renovated, lakefront and minutes from downtown! Welcome to this exquisitely updated 4-bedroom, 3.5-bath pool home with 90 feet of frontage on Lake Apopka, the fourth-largest lake in Florida, in the gated, golf-cart-friendly community of Lakeview Reserve. Expansive open-water views, streaming natural light and a beautifully reimagined interior create an unforgettable first impression. LOCATION: Just 2 miles to historic Downtown Winter Garden, reachable by golf cart, with Plant Street's restaurants, boutiques, events and the famous Saturday Farmers Market. The West Orange Trail is right outside the community gate, six highly rated golf clubs are within a 5-mile radius, and top-rated elementary and middle schools are less than a mile away. Enjoy easy access to shopping, Florida's Turnpike, downtown Orlando and the theme parks. RENOVATION: An extensive whole-home renovation brings a polished contemporary feel, with large-format porcelain tile, fresh paint and striking new lighting. The living room's panoramic water views anchor an open-concept layout that flows into the oversized dining room and kitchen. The completely renovated kitchen features high-gloss white flat-panel cabinetry, frosted glass accents, quartz countertops, a full-height quartz backsplash, an oversized waterfall island, stainless steel appliances, abundant storage and a built-in bar with wine storage. Every bathroom is beautifully remodeled, and each has a window and exhaust fan. The first floor hosts the primary suite plus two additional bedrooms, all with 11-ft ceilings, and every bedroom in the home enjoys a lake view. The primary suite offers real hardwood floors, two walk-in closets and a private screened porch overlooking the lake. Its spa-inspired bathroom includes dual vessel sinks, a makeup area, jetted soaking tub and glass-enclosed shower with rainfall and body spray fixtures. A first-floor office or den adds a quiet place to work. Upstairs, real hardwood continues to an oversized loft/flex space with full bath, walk-in closet and separate HVAC, ideal for guests or entertainment. Two Florida rooms, one on each floor, each with its own mini-split system, offer year-round panoramic lake views. OUTDOORS: A fenced, private backyard opens to sweeping open-water views. The recently resurfaced saltwater pool (new pump and filter 2026) and freshly repainted pool deck lead to a private covered dock with a 5,000-lb electric boat lift, electricity and water. Spend afternoons swimming, boating or fishing, then watch brilliant Florida sunsets from the dock. An extensive driveway and freshly painted two-car garage with built-in storage add everyday convenience. ENERGY EFFICIENT: This solar-powered home also features all new windows (2024), a new main first-floor AC (2026) and mini-split systems in both Florida rooms. The seller currently pays only an approximately $30 monthly grid fee, compared to a previous $500-$600 monthly electric bill. The seller will pay off the solar loan at closing, OR the purchase price may be reduced if the buyer assumes the existing low-interest solar panel loan. Mornings of sunlight on the lake, afternoons by the pool or on the boat, evenings on the dock beneath a painted Florida sky, with downtown Winter Garden just a golf cart ride away. This is the feeling of being on vacation every day, without ever leaving home.

261 Zachary Wade Street, Winter Garden

2420 Balforn Tower Way, Winter Garden
$599,900
3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Most evenings, unforgettable sunsets stretch across the pool and lake, casting a breathtaking glow over this premier cul-de-sac homesite. Set on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted vantage points—serene water views paired with sweeping Back 9 sceneries, including uninterrupted sightlines to the 13th green and 14th tee. Welcome home to an immaculate 3-bedroom, 2-bath split-plan retreat that is truly move-in ready. From the moment you step inside, you’ll feel the care, quality, and comfort woven throughout. Thoughtful upgrades include brand-new plantation shutters, a custom built-in kitchen nook with outlet, updated light fixtures and fans, and a new refrigerator. Major systems add peace of mind with a roof, HVAC, hot water heater, and interior paint all less than 3 years old. The open living area impresses with a striking white stone accent wall and durable wood-like tile flooring that flows seamlessly throughout the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Step outside to your private oasis: a covered lanai overlooking a stunning saltwater pool with sun shelf and water features, all less than 5 years old. The backdrop is pure magic—tranquil water, golf course views, and sunsets that feel like a nightly masterpiece. The fully fenced yard includes fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly positioned on a quiet cul-de-sac next to the residents’ gate, this home blends privacy with convenience. Community amenities are exceptional: golf course, playgrounds, pickleball, tennis, basketball, hockey court, resort-style pool, gym, and the Stoneybrook restaurant. Zoned for highly rated schools and just minutes from Winter Garden Village with easy access to the 429, the location is unbeatable. Additional highlights include built-in garage storage and shelving, a fenced yard, and standout curb appeal. This home delivers comfort, style, and a lifestyle that’s hard to match. Call today for a private showing!

2420 Balforn Tower Way, Winter Garden

1112 Hull Island Drive, Oakland
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.

1112 Hull Island Drive, Oakland

7573 Green Mountain Way, Winter Garden
$1,690,000
4 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to an exceptional lakefront estate on the shores of Lake Hancock, one of Central Florida's premier ski lakes. Situated on an expansive 1.26-acre homesite, this beautifully designed residence offers 4 bedrooms, 3 full bathrooms, 1 half bathroom, and nearly 3,400 square feet of thoughtfully crafted living space with breathtaking water views. The open-concept floor plan is perfect for both everyday living and entertaining, featuring formal living and dining rooms, a spacious family room, and a gourmet kitchen complete with quartz countertops, 42-inch cabinetry, stainless steel gas appliances, a pot filler, farmhouse sink, and a convenient butler's pantry. The split-bedroom layout provides privacy, while the bonus room offers endless possibilities as a media room, game room, home office, or home gym. Step outside to your private Florida oasis featuring a screened-in pool and private boat dock with direct access to Lake Hancock. Spend your days boating, skiing, or simply relaxing while enjoying spectacular sunsets and nightly Disney fireworks from your own backyard. Additional highlights include a 3-car garage, high ceilings, elegant architectural details, and access to outstanding community amenities including a resort-style pool, splash pad, clubhouse, fitness center, and scenic walking and biking trails. Ideally located just minutes from Hamlin Town Center, shopping, dining, top-rated schools, SR 429, and Walt Disney World, this remarkable waterfront home offers the perfect combination of luxury, privacy, and convenience.

7573 Green Mountain Way, Winter Garden

7301 Wild Blackberry Trail, Winter Garden
$2,400,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. This statuesque Mediterranean home is perfectly placed along Hancock Lake for maximum lakefront enjoyment. Your private covered dock protects a 20’ +/- boat w/lift as well as the lifts for 2 jet skis. Motor boat or pontoon around the lake, bring your favorite fishing rod or ski on one of the nicest skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a delightful custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and pool ledge. Enjoy the lake views then after sunset, pull down the projector screen for your favorite flick before watching the nightly fireworks show from the Disney park. The home's exterior and interior were freshly painted. Notice the wide baseboards and crown trim throughout. Spectacular front entrance with impressive light fixtures that accentuate the formal living and dining areas and frame your first glimpse of the lake. Impressive, upgraded Double Pane Low E sliding doors showcase the patio and lake then pocket to merge your spaces. The Kitchen is equipped with multiple food prep areas, generous walk-in pantry, and a central island workstation with seating for informal gatherings. A hallway behind the Kitchen shares the cabana bath and another first floor bedroom or den or office with a sliding door to the patio and a sizable walk-in closet. The first level’s primary suite has private patio access too and a lovely bay window styled seating area. (The previous owners used this primary as a media room complete with surround sound that remains intact). The loft also has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. The upper level contains a large ensuite with a private balcony, another ensuite, two bedrooms that share a hall bath and another bedroom with a private balcony overlooking the patio. The security system is located in the upstairs laundry room. Both A/C Systems, all patio doors, exterior balcony railings secured and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy. Plans for the new satellite elementary campus of Windemere Preparatory School are underway that will be located less than 2 miles from this home. ***Photos of fireworks and formal dining area are THE ONLY PHOTOS virtually staged.

7301 Wild Blackberry Trail, Winter Garden

16038 Johns Lake Overlook Drive, Winter Garden
$1,999,999
5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden

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