Luxury properties in Winter Garden

Pre-Construction. To be built. Location, Location, Medical, profesional, retail with Direct frontage on West Colonial Drive, at Tucker Oaks Blvd, in Winter Garden with an excellent traffic count, highway frontage. 4 condo retail pads available with approximately 23,280 SQF. $4,733,000 Active

15400 Colonial Dr Boulevard Winter Garden, Florida

4.71 Acres

COMMERCIAL property in downtown WINTER GARDEN! Located directly on PLANT STREET in the Historic District Overlay this property offers great exposure. It is currently zoned C-1 and has many permitted uses such as retail establishments, eating and drinking establishments, office & studios, financial institutions, private club, personal service, church and more. Permitted use list available upon request. Total property consist of over 3300 square feet and almost 2700 square feet of interior space. Property is split up unit two units. The first unit is approximately 1050 interior space offering a main retail area measuring 25x22, an office 9x14 and additional room 18x8. There is additional walkway space and two restrooms. The second unit is approximately 2050 interior space offering a 31x14 retail space, and additional spaces measuring 6x14, 8x12,10x17,18x24 and 7x15. There is additional walkway space and one restroom plus rear entrance/exit ability. ENJOY the downtown Winter Garden life. $2,999,000 Active

18 & 20 E Plant Street Winter Garden, Florida

2,699 SqFt 0.07 Acres

Situated just off the lively Plant Street corridor, this renovated professional office building at 557 W. Plant Street offers high visibility and steady daily traffic from both Plant Street and the West Orange Trail, which runs directly behind the property. The location places you within a short walk to Crooked Can, Plant Street Market, City Hall, coffee shops, restaurants, and the weekly downtown market, allowing your business to be part of the everyday rhythm of Winter Garden. The building has been thoughtfully updated with a new roof, new mechanical systems, and new electrical work, providing peace of mind for long-term use. Inside, the layout is warm and functional, offering five private offices, a conference room, a training room, three restrooms, and a kitchen/breakroom, making it well-suited for a variety of professional uses. This is a move-in-ready opportunity to establish your business in one of Winter Garden’s most walkable and desirable locations, surrounded by community activity and local charm. $1,390,033 Active

557 W Plant Street Winter Garden, Florida

0.31 Acres

Under contract-accepting backup offers. Prime 4.86 Acres Zoned A-1 in Winter Garden – Rare Opportunity! Now available—4.86 acres of A-1 zoned land just off Avalon Road in the thriving Winter Garden area. ***This unique property is adjacent to an additional 9.57-acre parcel of vacant land also for sale. For details on the adjoining parcel, see MLS #O6278339 – 3103 Avalon Rd.*** Currently operating as a successful ornamental plant nursery, the site features an impressive 8,115 sqft metal building, which includes approximately 1,500 sqft of air-conditioned office space with four offices and two restrooms. The remaining 6,615 sqft serves as warehouse space, complete with two loading docks and a service ramp—perfect for agricultural, storage, or light industrial use. Additional structures include four greenhouses, a trailer, and a security fence enclosing the property (excluding the boundary shared with the neighboring 9.57-acre parcel). Enjoy excellent access to major roadways including Florida’s Turnpike, SR-408, and SR-429, making transportation and logistics a breeze. The property is also near top destinations such as Disney’s Magic Kingdom, Winter Garden Village, Historic Downtown Winter Garden, Horizon West Town Center, and Downtown Orlando. Situated on the edge of the Lake Avalon Rural Settlement, this property offers the ideal blend of accessibility and agricultural charm. $989,000 Pending

16363 Davenport Road Winter Garden, Florida

1,500 SqFt 4.86 Acres

NEW PRICE..... LOCATION LOCATION LOCATION: Situated in the heart of Winter Garden, this property offers high visibility and convenient access for both businesses and customers. Diverse Tenant Mix: The property is home to a successful car dealership, a trendy hair salon, and a versatile retail unit suitable for a convenience store, sandwich shop, or other retail concepts. Income-Generating Opportunity: Two units are currently occupied, providing an excellent investment opportunity. Ample Parking: The property includes ample parking spaces to accommodate customers for all three businesses. Flexible Zoning: Zoned for a variety of commercial uses, offering future potential for tenant diversification or business growth. High Traffic Area: Located in a bustling area with consistent vehicle and pedestrian traffic, ensuring visibility and footfall for businesses. Turnkey Investment: Well-maintained property with established tenants, ready to provide immediate returns. Strong Community: Winter Garden is a rapidly growing area with a vibrant community and a strong local economy, making this property a strategic location for businesses. Upscale Surroundings: Surrounded by residential neighborhoods and other thriving businesses, the location supports a steady customer base. Growth Potential: With the area's continued development, this property offers potential for rental growth and increased property value over time. Beautiful commercial building on a corner lot steps away from West Colonial Drive with. Less than 5 miles away from two huge Central Florida auto auctions and a mile away from the Florida Turnpike and the SR 429 expressway. This building includes 3 suites that are currently rented by tenants including the auto dealer office and a beauty salon. Use this property as an auto dealership OR convert the building into a convenient store, a huge office, or whatever your heart desires. Plenty of parking – 10 spaces for the auto lot plus more parking for customers along the front of the building. This is prime real estate! Schedule your private showing today. $850,000 Active

595 9th Street Winter Garden, Florida

1,204 SqFt 0.21 Acres

Under contract-accepting backup offers. Pre-Construction. To be built. Prime commercial lot in the heart of Winter Garden. 0.30-acre site with approved architectural, structural, and engineering plans for a 2,250 SF retail/office shell under the 2023 Florida Building Code. Zoned R-NC (Neighborhood Center), ideal for medical, office, or professional use. Permit-ready site with city water and sewer available. Excellent visibility and access from W Story Rd, minutes from Downtown Winter Garden. Save 9–12 months of design and permitting time—ready to build now. $470,000 Pending

244 W Story Road Winter Garden, Florida

2,066 SqFt 0.3 Acres

Opportunity to build the interior as you wish. 48 X 24 feet with high celling. Previously used as a church building. It is well built. Walls are solid thick concrete. The zoning is RNC-2. The permitted uses include residential, duplex, public and private schools, assemblies, non profit, government facilities. Can include whatever the city can approve for you and whatever your imaginations designs. It is right next to Maxey Community Center. You may partner with them to share parking. It has electricity and plumbing connections. Ready for you to make it all new the way you want it. Owner will finance with twenty percent down and a low interest rate.This will take you to the permitted uses in the city of winter garden: https://library.municode.com/fl/winter_garden/codes/code_of_ordinances?nodeId=PTIICOOR_CH118ZO_ARTIVDIRE_DIV7.1RZODI $250,000 Active

844 Klondike Street Winter Garden, Florida

1,300 SqFt 0.1 Acres

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Step into a life of refined Southern charm and modern luxury at 15201 E Oakland Ave, nestled in the coveted Oakland Park community of Winter Garden. This custom Modern Farmhouse sits on a .44-acre fully fenced lot, anchored by two majestic oak trees, offering 4,507 square feet of thoughtfully designed living space that blends timeless elegance with today’s comforts. Enter through the wraparound front porch and feel instantly at home. Inside, the layout is both grand and inviting, featuring a rear-entry garage and a full guest apartment, perfect for extended family or visiting friends. Outdoors, luxury meets leisure: a sparkling open-air pool, spa, and cold plunge await, complemented by a fire pit, turf, and multiple porches—including a side porch and screened back porch. Sit back in your rocking chair and wind down your day, soaking in the serenity of your private oasis. Located in Winter Garden’s golf cart district, you're mere minutes from Plant Street Market, Crooked Can Brewery, award-winning farmers market, and the charming shops and restaurants of downtown Winter Garden. For outdoor enthusiasts, the West Orange Trail is literally in your backyard. Beyond its stunning design and location, this home resides in Oakland Park, an award-winning green-certified community, combining sustainable living with style and comfort. Experience a home where modern farmhouse elegance meets Florida outdoor living—a place where every day feels like a getaway. $3,000,000 Active

15201 E Oakland Avenue Winter Garden, Florida

4 Beds 5 Baths 4,507 SqFt 0.44 Acres

$2,480,000 WITHOUT FURNITURE OPTION AVAILABLE — LIST PRICE OF $2,680,000 INCLUDES ALL FURNITURE. Impressive two-story residence located in Avalon Ridge, Winter Garden. Built in 2024, this home features 6 bedrooms, 5 full baths and 2 half baths, with a floor plan that perfectly balances elegance and functionality. Custom high-end carpentry is present throughout, including built-in cabinets, walk-in closets, vanities, and a kitchen designed to stand out. All original floors were replaced with premium materials, and every closet was redesigned to maximize space and organization. There are two electrical spots to car charge included. The living areas are open and inviting, seamlessly connecting to the gourmet kitchen, creating an ideal setting for everyday living and entertaining. The primary suite on the first floor offers a spacious walk-in closet and a spa-style bathroom with dual sinks. Upstairs, the additional bedrooms include a Jack & Jill bathroom and flexible spaces to fit different lifestyles. A private movie room and laundry rooms on both levels bring comfort and convenience. Large sliding doors lead to the outdoor area with a pool and stunning sunset views. $2,680,000 Active

16077 Barkly Ridge Court Winter Garden, Florida

6 Beds 7 Baths 5,248 SqFt 0.27 Acres

Stunning custom-built lakefront pool home on Lake Hancock offering luxury, comfort, and breathtaking views from nearly every room. Designed for entertaining, this remarkable residence features a chef’s dream kitchen with a wrap-around bar, center island, Bertazzoni 5-burner gas range, double ovens, walk-in pantry, granite countertops, stainless steel appliances, and a stylish tile backsplash. The open living and family rooms flow seamlessly to the spacious lanai through elegant French doors, complete with retractable screens and a built-in gas grill for effortless indoor-outdoor living. The luxurious downstairs primary suite boasts a custom tray ceiling, spa-inspired bath with dual vanities, walk-in shower, large soaking tub, and spacious walk-in closets, with direct access to the lanai and pool. Upstairs, a screened lanai accessible from the bedroom, den/office, and gallery provides stunning lake views. Relax in the heated pool and spa with outdoor shower, or follow the travertine walkway to the private boat dock equipped with electronic lifts for a boat and jet ski. Architectural details include high ceilings, custom crown molding, and elegant curved walls in the breakfast nook and primary bath. Set on 1.64 acres of professionally landscaped and fenced grounds, a portion extending into the lake, this home also enjoys access to the desirable Summerlake community with a resort-style clubhouse, pool, tennis courts, fitness center, park, dog park, and playground — the perfect blend of elegance, comfort, and Florida lakefront living. $2,530,000 Active

7757 Summerlake Pointe Boulevard Winter Garden, Florida

4 Beds 4 Baths 5,178 SqFt 1.64 Acres

Under contract-accepting backup offers. Welcome to 16110 Johns Lake Overlook, a stunning lakefront retreat in highly sought-after Winter Garden. Perfectly positioned on the shores of Johns Lake, this elegant 5-bedroom, 4.5-bath residence offers the best of Florida luxury living—complete with breathtaking water views, a private dock, and resort-style outdoor amenities. Step inside and be greeted by a beautifully upgraded kitchen featuring a large island overlooking the lake, double ovens, walk-in pantry, and a built-in wine refrigerator—ideal for entertaining. The open-concept living areas flow seamlessly to the covered outdoor oasis, where you’ll find a full summer kitchen with Green Egg and a grill, sparkling pool and spa, and a cozy outdoor fireplace—all framed by sweeping lake views. The downstairs guest suite provides comfort and privacy for visitors, while the upstairs primary suite is a true sanctuary with French doors leading to a private screened porch and panoramic views of the water. A spacious loft/game room offers the perfect hangout space, and the impressive studio/craft room—with abundant cabinetry and inspiring lake views—adds exceptional versatility. The upstairs primary suite takes full advantage of the outstanding lake view, and has a huge screened porch where you can soak in the sunsets. There are three additional bedrooms upstairs, so your family or guests will have room to spread out. This home also boasts paid-off solar panels, keeping the monthly electric bill under $100, and includes a brand-new washer and dryer. Every detail has been thoughtfully curated for comfort, efficiency, and elegance. Enjoy waterfront living at its finest—where modern luxury meets natural beauty. $2,420,000 Pending

16110 Johns Lake Overlook Drive Winter Garden, Florida

5 Beds 5 Baths 4,959 SqFt 0.45 Acres

One or more photo(s) has been virtually staged. **WINTER GARDEN WONDER** Lakefront luxury with that true “WOW” factor—this furnished former model by Jones Homes USA sits on Hickory Nut Lake, showcases every builder upgrade imaginable and had a recent refresh for a turnkey, move-in ready experience. Enjoy panoramic water views from both levels, an oversized .36-acre lot with lush landscaping, resort-style pool & spa, and a private dock with power boat lift and seating area. Seamless indoor/outdoor living features retractable screens, a covered outdoor kitchen, and expansive sliders that open to all 4 patio spaces. Inside, discover custom millwork, glass-enclosed wine room, gourmet kitchen with oversized island, a flexible bonus room, spacious loft with wet bar, luxurious primary suite with balcony access, and SO MUCH MORE! Premier location near top-rated schools, Disney, and Winter Garden Village. Home is being sold as-is with all existing furniture and décor included. Schedule your showing today! $2,375,000 Active

9080 Morgana Court Winter Garden, Florida

5 Beds 5 Baths 5,390 SqFt 0.36 Acres

Perfectly positioned within Twinwaters, one of Winter Garden’s most sought-after communities, this remarkable 7-bedroom, 6.5-bath residence captures the essence of refined Florida living. Built in 2016 and extensively upgraded, it now combines modern sophistication with timeless design — offering over 5,200 square feet of thoughtfully curated space designed for both relaxation and entertaining. The home enjoys access to private, motorized Johns Lake, offering opportunities for boating, paddleboarding, and lakefront leisure, with ample room for a future dock and a resort-style pool to complete the lakeside lifestyle. Step inside a transformed space. Newly installed luxury vinyl plank flooring extends throughout the home, while new tempered-glass stair railings and upgraded LED lighting add a bright, contemporary edge. Every bathroom has been reimagined with custom cabinetry, quartz surfaces, frameless glass showers, and elegant fixtures. The primary suite, located on the main level, has been completely redefined into a private retreat featuring a custom-built headboard wall, floating side tables with integrated lighting, and a spa-like bath with slate tile, a freestanding tub, quartz counters, and a modern smart bidet toilet. A second ensuite bedroom on the lower level offers flexibility for multi-generational living or guest accommodations. The heart of the home centers around a grand living area, anchored by a custom-designed feature wall with an 85-inch built-in television, Samsung sound bar, and a Touchstone 84-inch recessed electric fireplace — blending architectural statement with warmth and comfort. The living area opens to an elegant dining space and a well-appointed kitchen featuring under-cabinet lighting, upgraded fixtures, and repainted cabinetry for a fresh, polished aesthetic. Smart-home features such as Schlage Encode smart locks, Ecowater purification system, Ring doorbell, and remotely controlled thermostats enhance everyday convenience. Upstairs, the entertainment experience continues with a dedicated home theater — a professionally designed space with a 120-inch built-in screen, projector, and surround sound system — See full description $2,249,000 Active

16689 Broadwater Avenue Winter Garden, Florida

7 Beds 7 Baths 5,283 SqFt 0.36 Acres

LUXURY ISLAND HOME IN POPULAR GATED COMMUNITY. Experience modern lakefront luxury in Emerald Point, an exclusive gated island of only 28 homes within the desirable Hickory Hammock community, offering a rare blend of luxury, privacy and premium lakefront living. Perfectly positioned on Johns Lake, this contemporary two-story home showcases clean architectural lines, sophisticated finishes, and breathtaking water views, offering the ultimate in Florida living. Privacy and serenity are exceptional with wide lake views from nearly every room and a charming, landscaped park with towering oaks directly across the street. From the moment you enter, a dramatic two-story foyer with upgraded crystal light fixtures and a striking clear view of the lake sets the tone for this modern masterpiece. The formal dining area flows seamlessly into the expansive great room, where an open concept design, stacked stone accent wall, and a rear wall of stackable sliding glass doors creating a true indoor-outdoor living experience. The oversized gourmet kitchen is a chef’s dream, featuring dual islands, pot filler, built-in side-by-side stainless steel refrigerator and freezer, double ovens with convection, built-in microwave, and a dedicated wine and beverage cooler. White shaker cabinetry with illuminated glass inserts, crown molding, quartz countertops, glass tile backsplash, and an oversized walk-in pantry elevate the space. The breakfast nook is perfectly positioned to capture tranquil lake views with every meal. The main level offers a thoughtfully placed half bath for guests, along with a private guest suite featuring sliding doors to the covered lanai and an ensuite bath, ideal for extended stays or multigenerational living. Upstairs, modern glass and stainless-steel railing lead to a spacious bonus room with a full wet bar and additional wine and beverage cooler. This impressive entertaining space opens to a generous balcony with sweeping, unobstructed views of Johns Lake. A convenient laundry room with LG washer and dryer and a second half bath add to the home’s functionality. The primary suite is a serene lakefront retreat, boasting dual walk-in closets, private balcony overlooking Johns Lake, and a spa-inspired ensuite with oversized walk-in shower with rain shower head, garden tub, and dual quartz vanities. Three additional upstairs bedrooms include generous closets, ceiling fans, and either ensuite or Jack-and-Jill baths with tile flooring, quartz counters, and tub/shower combinations; perfect for family or guests. Modern conveniences abound, including a Nest home system, motorized rolling shades, whole-house water filtration with reverse osmosis, and an oversized 3-car garage. The east-facing rear yard offers approximately 102 feet of lake frontage, thoughtfully oriented to avoid the harsh afternoon sun while maximizing shimmering water views throughout the day. Residents of Hickory Hammock enjoy resort-style amenities including a zero-entry pool, clubhouse, fitness center, tennis and volleyball courts, fishing pier, playgrounds, walking trails, and a dog park. Located just minutes from historic Downtown Winter Garden, Winter Garden Village, area attractions, Disney, and Orlando International Airport, this residence perfectly blends contemporary design, lakefront luxury, and everyday convenience. Schedule your private showing today and experience lakefront sophistication at Emerald Point at Hickory Hammock. $2,150,000 Active

15783 Tangerine Dream Court Winter Garden, Florida

5 Beds 6 Baths 4,478 SqFt 0.42 Acres

Discover Winter Garden’s best-kept secret in Avalon Estates, a peaceful, horse-friendly enclave where timeless country charm meets modern luxury. This custom-built residence offers an impressive 6,400 sq. ft. under air and nearly 10,000 sq. ft. under roof, set on 4.6 picturesque acres surrounded by nature and serenity. From the moment you arrive, the inviting curb appeal and sprawling front porch set the tone for what awaits inside. Step through the double entry doors into a grand living space filled with soaring ceilings, abundant natural light, and an airy, open feel that defines Florida living at its finest. The modern farmhouse kitchen is a dream for entertaining, featuring two expansive islands, generous counter space, and seamless flow into the family room, where a wood-burning fireplace adds warmth and charm. French doors open to the pool area, complete with two oversized covered lanais, creating an ideal setting for relaxing or hosting guests. The downstairs primary suite is both spacious and inviting, featuring a private fireplace, large walk-in closet, and a magazine-worthy en suite bath. A private office sits just off the primary suite, offering a quiet retreat for work or study. Upstairs, you’ll find a large bonus room with kitchenette, three additional bedrooms, and two full bathrooms—perfect for family or guests. Don’t miss the panoramic views through the large windows—on clear nights, you can watch Disney fireworks sparkle in the distance and even catch NASA rocket launches from the east coast. Built with poured concrete tilt-wall construction, this home is as strong and resilient as it is beautiful. The laundry room doubles as a safe room, featuring metal doors, bullet-resistant glass, and reinforced concrete walls and ceiling. Additional highlights include a new roof (2025), an attached three-car garage, plus a detached 2.5-car garage with studio and full bath—ideal for guest quarters, an office, or hobby space. Located just minutes from shopping, dining, and major highways (Florida Turnpike, 429, and 408), this estate is 11 miles from Disney World, 12 miles from Universal Studios, and 23 miles from Orlando International Airport. With its combination of space, craftsmanship, and location, this property also offers excellent potential as a luxury short-term rental. Experience the tranquility and grandeur of Avalon Estates—schedule your private tour today and start creating lifelong memories in your new home. $2,079,000 Active

17261 Heartwood Loop Winter Garden, Florida

5 Beds 7 Baths 6,400 SqFt 4.6 Acres

Completely Remodeled Waterfront Luxury Home – Boater’s Paradise on Lake Apopka Experience the ultimate in lakefront living with this stunning, turnkey home on Lake Apopka in Winter Garden. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm, offering breathtaking sunrise and sunset views every day. Every inch of this home has been meticulously upgraded with nearly $450,000 invested in recent renovations, creating a move-in-ready oasis with high ceilings, spacious open-concept living, and designer finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, upgraded windows. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, and a modern backsplash. Entertain effortlessly in the expansive dining room and living room framing incredible lake views. The master suite is a serene retreat with two walk-in closets, an oversized Jacuzzi bathroom, and stunning water vistas. Each bedroom boasts lake views, while a second-floor guest bedroom offers privacy, a separate bathroom, and noise-reducing flooring—perfect for a home theater or office. A dedicated office/den at the entrance is ideal for remote work or study. Outdoor living is exceptional with two enclosed and screened patios on the first and second floors, providing panoramic lake views. Boaters will love the expansive deep-water dock with lift and the fun Margaritaville-themed bar. The backyard features a newly resurfaced saltwater pool with a new pump, fully fenced secure yard for kids and pets, fruit trees and mature, landscaped greenery creating a private oasis. Additional highlights include new windows, new HVAC, new solar panels, smart thermostat, upgraded irrigation, and a two-car garage with built-ins. Located in a quiet, family-friendly gated community with golf-cart-friendly streets and direct access to the scenic West Orange Trail. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the famous weekend farmers market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways without the traffic. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun! Price can be reduced by $40,000 if the buyer is willing to assume a low-rated solar panels loan! $1,890,000 Active

261 Zachary Wade Street Winter Garden, Florida

4 Beds 4 Baths 3,728 SqFt 0.27 Acres

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