Winter Garden, Florida listings for sale

$1,999,000 - Winter Garden, FL

16086 Johns Lake Overlook Drive Winter Garden, FL - Stunning Lakefront Estate with Pool and Dock in Gated Hickory Hammock. This is a rare opportunity to own a luxury residence on Johns Lake, located in vibrant Winter Garden. This beautifully appointed Lewiston floor plan offers five bedrooms, four full bathrooms, two half baths, and a host of refined upgrades throughout—perfectly blending elegance, comfort, and Florida outdoor living. From the moment you enter, you’re welcomed by a dramatic two-story foyer with 20-foot ceilings, a striking grand staircase, and an elegant powder room. Just off the entryway, a flexible space can serve as a formal dining room, living room, or home office to suit your lifestyle. At the center of the home is an impressive chef’s (super) kitchen, designed for both entertaining and everyday living. It features two large, wood-wrapped islands—one with a sink and one with counter seating—quartz countertops, white cabinetry with custom drawer storage, frosted glass accent doors, a stylish backsplash, and a double oven (including convection). The electric cooktop, walk-in pantry, sunlit dinette, and included appliances make this kitchen as functional as it is beautiful. The open-concept family room flows seamlessly to the outdoors through triple sliding glass doors. Step outside into your private retreat featuring a fully fenced backyard, resort-style saltwater pool with lap lane, 10-foot depth, and sun shelf—all surrounded by lush landscaping. Just beyond, follow a grassy path to your private boat dock, complete with electric, water, 7,500-pound lift, Trex walkway, ladder, and seating area. It's the perfect place to relax and enjoy the breathtaking sunsets and nightly Disney fireworks over Johns Lake. The thoughtful layout includes a first-floor in-law suite with a private entrance, full ensuite bath with walk-in shower, walk-in closet, and screened patio—ideal for guests or multigenerational living. Upstairs, the spacious primary suite offers panoramic lake views through a wall of windows, tray ceilings, and French doors that open to a private balcony overlooking the pool, backyard, and waterfront. The luxurious ensuite bathroom includes two vanities, a garden tub, large walk-in shower, and generous closet space. Three additional upstairs bedrooms include one with a private bath and two that share a Jack-and-Jill bathroom. A large laundry room with lower cabinets and sink adds convenience, while the spacious flex room facing the lake is perfect for a game room, media space, or home office. The home features 10-foot ceilings on the first floor, 9-foot ceilings upstairs, engineered hardwood flooring throughout, smart fans, fresh exterior paint completed in 2025, and a split three-car garage offering excellent storage for recreational gear, vehicles, or water toys. Located within one of Winter Garden’s premier gated communities, residents enjoy access to a resort-style pool, fitness center, clubhouse, tennis and volleyball courts, dog park, playground, fishing pier, and scenic walking trails. Zoned for top-rated schools and ideally situated near Winter Garden Village, downtown Winter Garden, major highways, and just 15 miles from Orlando’s world-class attractions, this exceptional lakefront home truly offers it all. Now available and ready for immediate occupancy—this is your opportunity to enjoy the ultimate Florida lifestyle. Contact the listing agent to schedule your private showing today.

$1,995,000 - Winter Garden, FL

260 Deer Isle Drive Winter Garden, FL - This BRAND NEW CONSTRUCTION home directly on John's Lake is one of a kind with over 2 acres behind, high and dry, over 500 feet of direct lake frontage, plus 4700 sqft of living space, 5 spacious bedrooms, 4 full bathrooms, one half bath and a true open concept design. As you walk in the front door, you're greeted by tons of natural light from all the sliding glass doors and oversized windows, along with 12 foot high ceilings, a living room, dining room and kitchen combo, plus luxury hardwood flooring throughout the entire house. The family room is perfect for all gatherings, cozy nights in, and has breathtaking views of the lake. The kitchen has a massive island, luxury countertops with a waterfall feature over the sides, plenty of cabinetry, high end appliances, and perfect for entertaining as it's open to the entire home. If you enjoy having a large formal dining room and living room then this house has designated areas for both! The owner's suite is on the left side of the house and is completely private with tons of amenities. The owner's suite has stunning views from the bedroom, ensuite, closets and even the workout room. The owner's ensuite has his and her vanities, custom lighting, a large walk in shower with high end tile work, a soaking tub that sits in front of a large window overlooking the lake, and is completely private with exterior walls on the side. The owner's retreat also offers two oversized closets, and a third room that could be another closet, a nursery, a second office, or even a home gym. The right side of the home offers 3 spacious bedrooms all with ensuite bathrooms and walk in closets. It also has a half bathroom for guests and a laundry room with built in cabinetry and sink. If you enjoy entertaining then open up your sliding glass doors and step onto your over 500 sqft of covered lanai space with wood ceilings and sunset views. This property has a grandfathered in tree house boat dock that can be one of a kind for this neighborhood. This property has the ability to add an additional mother in law suite, casita, secondary garage or etc. John's lake is approximately 2500 acres that offers sport fishing, skiing, canoeing, kayaking and all other water-sports. This new construction home comes with a builder warranty as well, ask for further details! This home is nestled in the highly sought after Deer Island community, known for its lake frontage on John's lake, community amenities and amazing location right between downtown Winter Garden and Downtown Clermont. It's also located just a short drive from the magic of Disney, the vibrant atmosphere of International Drive, and premier shopping at Millennia Mall, this home offers convenience paired with quality. Montverde Academy, a world-class educational institution known for its commitment to academic excellence, is also less than seven miles away. Discover the perfect blend of sophistication and functionality in this meticulously crafted home, offering both comfort and style. Schedule a private viewing today and make this your retreat in the heart of convenience.

$1,990,000 - Winter Garden, FL

214 S Woodland Street Winter Garden, FL - Calling all Investors and Developers or anyone looking for a GREAT location to call home. Located in the heart of Downtown Winter Garden, this property offers a goldmine of opportunity for those looking to develop in the already thriving downtown area. Zoned R-2, this large and spacious corner lot can be developed by building 6 condo units or 3 Single Family Homes. Property is located within one block of Plant St and one block from Dillard St. Street Renovations are in the works to completely redesign approximately one mile of South Dillard St leading out to Plant St which will add roundabouts and Bicycle lanes, thus revitalizing the entire area around the property. If development doesn't interest you, this property offers a Charming 1925 4-Bedroom, 2-Bath Home with a historic appeal. Step back in time with this well crafted and maintained, 1925-built home, blending historic appeal with modern updates. With 4 spacious bedrooms and 2 bathrooms, this home offers ample space for families or those who love to entertain. You'll be greeted by rich hardwood flooring throughout the home, exuding warmth and character along with ceramic marble flooring throughout other parts of the home. The home retains many original architectural details, complemented by modern amenities for today’s lifestyle. Large windows fill the home with natural light, 37 out of 52 windows have recently been replaced by seller and the roof was replaced in 2019. *Stunning Pool with Screened-In Outdoor Oasis – Perfect for Entertaining** Dive into luxury with this beautiful pool surrounded by a spacious screened-in enclosure, designed for ultimate relaxation and entertainment. The centerpiece of this outdoor retreat is a fully equipped outdoor kitchen, complete with a double sink, refrigerator and ample counter space, making hosting a breeze. Adjacent to the outdoor kitchen is a large seating area, perfect for dining, lounging, or gathering with friends and family. Whether you're enjoying a sunny afternoon by the pool or a cozy evening under the stars, this space offers comfort and style year-round. Enjoy the perfect blend of indoor-outdoor living in your private paradise—ideal for hosting unforgettable parties and gatherings or relaxing in serene privacy. Property also offers a 1 bedroom, 1 bath apartment overlooking the pool area which sellers are currently renting out for $1,000.00 monthly. Don't miss out on this golden opportunity! Call today for more information and to set up a showing.

$1,925,000 - Winter Garden, FL

16761 Broadwater Avenue Winter Garden, FL - Welcome to 16761 Broadwater Avenue, a stunning lakefront estate nestled in the beautiful community of Winter Garden, FL. Situated on an expansive 20,282 sq ft lot, this 5-bedroom, 5.5-bathroom residence offers 3,633 square feet of thoughtfully designed luxury. As you arrive, a gated entry welcomes you into a charming open-air courtyard, setting the stage for the elegant experience that awaits inside. Step through the front door and into an open-concept living space designed for both comfort and sophistication. High ceilings and natural light enhance the flow between the living and dining areas, making it ideal for both everyday living and upscale entertaining. The gourmet kitchen features sleek finishes, ample cabinetry, and a spacious layout perfect for gatherings. Just off the kitchen, discover a custom wine fridge area with a built-in wine rack—a stylish touch for the wine enthusiast. Upstairs, a cozy den with a built-in bar adds yet another space for entertainment and relaxation. The primary suite serves as a peaceful retreat, complete with a luxurious ensuite bathroom and generous walk-in closet. Each additional bedroom offers privacy, space, and its own ensuite bath, ensuring comfort for all. Step outside to your screened-in saltwater, heated pool and spa, where serene lake views create the ultimate backdrop for relaxation. The covered patio features a built-in outdoor kitchen, perfect for alfresco dining and entertaining under the stars. Waterside at Johns Lake is a gated community offering a range of resort-style amenities including a fitness center, community pool, and playground. Enjoy the convenience of being just minutes from Orlando, Disney, and Universal, with easy access to 408, the Turnpike, and 429. Explore nearby lakes, scenic trails, and shopping—and you're only about an hour from the beach. This exceptional home masterfully blends smart design with modern luxury. Don’t miss the opportunity to make this elegant lakefront retreat your own—schedule your private showing today!

$1,800,000 - Winter Garden, FL

557 Lake Cove Pointe Circle Winter Garden, FL - Nestled in the highly coveted lakefront golf cart district of downtown Winter Garden, this stunning property offers a rare opportunity to own a piece of paradise with direct lake access and premium amenities. Welcome to a magnificent home featuring 5 bedrooms, an office, a theatre/loft area, and 4.5 bathrooms, perfectly accommodating multigenerational families or anyone looking for an elegant and spacious living environment.The ground floor hosts one of the two primary suites, offering accessibility and convenience without sacrificing privacy and luxury. This suite features an en-suite bathroom, ample closet space, and serene views of the beautifully landscaped grounds.Ascend to the second floor to discover the secluded second primary suite, a true retreat. It provides a more intimate setting with a private balcony overlooking the lake—ideal for enjoying stunning sunsets in peace. This suite includes a single vanity, a standard bath, and the unique convenience of a private laundry, ensuring comfort and functionality. The custom laundry room is outfitted with double washers and dryers, making even the most daunting laundry tasks a breeze.The home is enhanced by sustainable features including a whole home generator and solar panels, ensuring energy efficiency and peace of mind during any weather.The heart of the home is the expansive living area that flows seamlessly into a gourmet kitchen equipped with top-of-the-line appliances, granite countertops, and custom cabinetry—ideal for those who love to cook and entertain. Adjacent to the kitchen, the dining area opens up to a sprawling outdoor living space featuring a poolside cabana and a private boathouse. Here, entertaining guests becomes an experience, with ample space for dining al fresco, summer barbecues, or tranquil evenings by the water.Outdoor enthusiasts will appreciate the easy access to the chain of lakes, where weekends can be spent boating, fishing, or simply exploring the waters. On land, take your golf cart to vibrant downtown Winter Garden, where you can enjoy dining at fine restaurants, shopping at boutique stores, and mingling at the weekly farmers' market.This home not only offers luxurious living but also a lifestyle of convenience and leisure in one of the most desirable locations in the area. Don’t miss your chance to experience this exceptional offering—a home where every day feels like a vacation.

$1,750,000 - Winter Garden, FL

7031 Billie Court Winter Garden, FL - Stunning LAKEFRONT home on Lake Hancock! You'll love this SINGLE LEVEL home that has had only ONE OWNER. The owners paid attention to every detail on this home, from the EXTRA WIDE for comfort, to the DUAL WATER HEATERS in the home which ensure hot water is at the ready for everyone. You'll enter the home through a gorgeous brick pavered enclosed courtyard. Inside you'll find a formal dining area, a massive living area with high ceilings, and a stunning kitchen. When the owners first moved into this home, I took a brief video of this kitchen and it went viral with OVER 24 MILLION views--that's how gorgeous and loved this kitchen in. From QUARTZ counters to the French door oven and convection/microwave, counter depth fridge, and GAS cooktop, and the HUGE ISLAND, you'll fall in love with it too. The rooms are all spacious, and the primary suite was cleverly designed with closet spaces that also privately connect to the laundry room, another detail adding to the comfort of this home. You'll step outside through a triple slider door, onto your screened porch ready for your summer kitchen installation. Here's there's a retractable screen to keep any bugs out while you're enjoying your LAKE FRONTAGE. Would you like to build your own private boat dock? You can build a 12 1/2 ft wide dock and enjoy the lake life. ALSO, the sellers are including a 6 SEATER GOLF CART with acceptable offer. You can fit it easily, since the home has garages for 3 cars. You'll find a double garage and a separate single garage. Just to add to this, you're in a great community with lots of amenities like community pool and clubhouse, community boat ramp, recreational facilities and more. View it today and enjoy the 3D interactive walkthrough online.

$1,699,999 - Winter Garden, FL

11630 Flynn Court Winter Garden, FL - A Stunning 5-Acre Estate in Winter Garden, FL – A Rare Opportunity! Welcome to your DREAM OASIS! This exceptional 5-acre estate is a perfect blend of country charm and modern convenience, with DUAL RESIDENCES and DETACHED CUSTOM GARAGE. Ideal for families seeking multi-generational living, investment opportunities, or simply a spacious retreat! MAIN RESIDENCE: The primary residence boasts 4 spacious bedrooms and 3 bathrooms, well-designed split floor plan includes a private office, ideal for remote work. Built by a seasoned builder, the home features American Hickory floors, a three-car tandem garage, a screened lanai, and a spacious kitchen with gas range, custom cabinetry, and a beverage bar. Thoughtful details throughout make this home both stylish and functional. SECOND HOME: In addition to the main home, the second home features 2 bedrooms, 2 bathrooms and an office. This versatile space is perfect for family, guests, or even as a rental unit to generate additional income. The home offers privacy and independence while still being part of the estate, making it an ideal solution for multi-generational living. DETACHED CUSTOM GARAGE: The estate also includes a remarkable 1,800 sq. ft. Garage, fully insulated, constructed in 2019. This spacious structure features two bays, providing ample storage for equipment, vehicles, or hobbies. Whether you envision it as a workshop with an office, a place for your agricultural pursuits, the possibilities are endless. Garage contents may be purchased outside of the Contract. Bathroom toilet is not connected. OUTDOOR LIVING: The entire property is fully fenced, ensuring privacy and security for your family and pets. The expansive 5-acre lot offers plenty of room for outdoor activities, gardening, or even the addition of a pool or recreational facilities. Enjoy the serene landscape, complete with mature trees and lush greenery, providing a tranquil backdrop for your everyday life. Avocado, peach, pomegranate, and olive trees plated throughout the property can provide harvests for decades to come. LOCATION: Situated in the highly sought-after Winter Garden area, this estate combines the best of both worlds—peaceful country living with easy access to urban amenities. Enjoy nearby shopping, dining, and entertainment options, as well as excellent schools and recreational facilities. The vibrant community of Winter Garden is known for its charming downtown, picturesque parks, and friendly atmosphere, making it a wonderful place to raise a family or invest in real estate. INVESTMENT POTENTIAL: This property is not just a home; it’s an investment opportunity. With the potential for rental income from the second home and the spacious grounds that could accommodate additional structures or agricultural ventures, the possibilities for generating revenue are substantial. Don’t miss out on this rare opportunity to own a piece of paradise in Winter Garden. Whether you’re looking for a family compound, a multi-generational residence, or a unique investment property, this estate has it all. Contact us today to schedule a private viewing and experience the charm and potential of this incredible property firsthand. Your dream of country living awaits!

$1,699,900 - Winter Garden, FL

10303 Atwater Bay Drive Winter Garden, FL - LAKEFRONT DREAM HOME! Bring your BOAT and Enjoy 71’ Feet of LAKEFRONT, a Gorgeous 5 Bedroom, 3 ½ Bath, 3 Car Garage Home with Screened LUXURY POOL AND SPA plus Weather-Resistant BOAT DOCK with TILE ROOF and BOAT LIFT! Spectacular Wide Open LAKE VIEWS and Disney Fireworks Views make this home Special! Go Fishing, Boating, Kayaking or try the WATER SKI COURSE on Private 420 Acre LAKE HICKORY NUT! Outstanding features include PREMIUM LOCATION with Best Water Views and 90 Feet of GREENSPACE next door for PRIVACY! Upgraded 8’ Glass and Wrought Iron Entry Door opens to 2 Story Foyer! GOURMET KITCHEN with 42” Cabinetry, VENT HOOD, CONVECTION OVEN and Microwave, 5 Burner Cooktop, NEW Dishwasher and SS FRENCH DOOR REFRIGERATOR! Beautiful QUARTZ Counters, Large Island, SS Farm Sink, FILTERED WATER DISPENSER, NO-TOUCH High Arc Faucet, Designer PENDANT LIGHTS, Walk-In Pantry and Convenient BUTLER PANTRY! Kitchen Overlooks Family Room with GRASS CLOTH ACCENT WALL and Casual Dining Opens to COVERED PATIO. New TROPICAL LANDSCAPING surrounds your RESORT STYLE Heated POOL with SALT SYSTEM, AUTOMATION SYSTEM, Pebbletech Surface, SUN SHELF, Fountain, DECK JETS and HOT TUB! Convenient FIRST FLOOR PRIMARY SUITE with STUNNING LAKE VIEWS has a Tray Ceiling, NEW CARPET, Walk-In Closet (13x9) and Primary Bath featuring a WALL TO WALL DOUBLE SHOWER, 2 Separate Sinks and Vanities and Linen Closet! Powder Bath and REMODELED Laundry Room with Sink and Cabinetry completes the First Floor. Wrought Iron Railing leads upstairs to SPACTIOUS LOFT! One wing has Bedroom 2 and 3 that Share Bath 2 with Double Sinks. Other Hallway has Bedrooms 4 and 5 with a Jack and Jill Bath. ALL Bedrooms have WALK-IN CLOSETS! This gently used 2nd Home has LOTS OF Great FEATURES and UPGRADES: TILE ROOF - Professionally Cleaned in 2024, Upgraded Fans & Light Fixtures, EXTERIOR PAINTED in 2024, 3 Car TANDEM Garage with EPOXY FLOOR and AIR CONDITIONER UNIT, $15,000 CHAIR LIFT on stairs, NEW Whole House Water Filtration and Softener System & ENERGY SAVING Features! ENJOY LIFE ON THE LAKE in Waterleigh – a Lifestyle Community with 4 Community Pools, 2 Club Houses with Fitness Centers, Tennis, Pickleball, Sand Volleyball, Mini Golf, Parks, Playgrounds, Community Fishing Dock and MORE! HOA Does all Yard Maintenance. Schools Include NEW Atwater Bay Elementary, Water Spring Middle and NEW Horizon High School. Close to Shopping, Dining, NEW Publix, DISNEY and convenient to 429, 1-4 and 417!

$1,699,900 - Winter Garden, FL

16548 Raven Rock Place Winter Garden, FL - Please note that property visits will only be confirmed upon receipt of proof of funds or a pre-qualification letter. All visits will be guided by the listing agent and must be requested at least 24 hours in advance. Kindly be aware that the owners currently reside in the property.

$1,599,000 - Winter Garden, FL

7833 Freestyle Lane Winter Garden, FL - Sellers are motivated and will consider ALL offers! Pool designs available! - A sprawling single story, meticulously maintained home nestled within the highly sought after Isles of Lake Hancock. This gated, waterfront community sits just minutes from Disney, holding a masterful open floor plan that greets all with an colorful artistic atmosphere, modern home tech features, flawless appliances, and upgrades fit for the ideal Florida lifestyle. The home is tailored with an abundant inspiration of imported contemporary Art, Metals, Glass, and upscale lighting design while sitting in a premier Horizon West gated community. Step foot into an opulent main foyer space and feel the interior sophistication in every direction, which extends into the formal dining room, office, kitchen and main living room. Complimenting Luxury Tile, and Engineered Hardwood floors accompany the Dark Custom Cabinetry, Glass Metallic Backsplash, and flawless Stainless Steel Appliances throughout the kitchen. Lofty 14-foot Double tray ceilings surround the entirety of the home, and 10ft ceilings with remote controlled invisible/retractable blade ceiling fans can be found in each secondary bedroom. The Primary bedroom is perfectly separated from all secondary bedrooms is comfortably designed around the Oversized Spa Bath and Walk in Shower, and a moody Custom designer Closet and storage. A spacious extended den area which also provides access to the exterior outdoor deck, acts perfectly as a reading room or lounge space in the morning. Enjoy masterful Interior and Exterior Entertainment choices such as two massive Theatre/Streaming Projectors, Overhead Outdoor Heating Unit, Electric Fireplace, Luxury LED Lighting Fixtures, Designer Home Entertainment Cabinetry, and Electric Screen Door Enclosure. Flawless Smoke Grey Epoxy floors lines the garage, and along with custom ceiling storage overhead cabinetry, and spacious room car lift capability. With direct access into two man-made lakes, this prestigiously known neighborhood acts as one of central Florida’s Premeir Water Skiing destinations, holding world class ski tournaments annually. The artistic, detailed, and meticulously maintained features of this home fill it with warmth and good energy. This statement piece home and its affluent upgrades and details are felt in every space, making this a must see Winter Gardens single story residence!

Winter Garden, Florida listings for sale

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