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$889,000
3 Beds ⋅ 4 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
Fully furnished, turnkey Urban retreat in Downtown Winter Garden — perfect for snowbirds, recent life-chapters, or anyone craving an active, walkable Florida lifestyle. This immaculate three-story townhome at Park Place offers 2,030 sq ft of stylish, move-in ready living with 3 beds, 3.5 baths and a custom elevator for easy access to every level. Why you’ll love it? Move-in ready: thoughtfully curated furnishings and decor — unpack, relax, entertain. Ideal for flexible living: private first-floor guest suite with full en-suite bath — perfect for in-laws, guests, or a live-work setup. Entertainer’s kitchen: chef-inspired with oversized island, breakfast bar, stainless appliances and gas range. Private primary level: spa bath with dual vanities, soaking tub and large walk-in shower. Comfortable modern features: natural gas, ceramic floors, plantation shutters, tankless water heater and rear-entry 2-car garage. Accessibility: custom elevator makes all three levels effortless. Location: You can live steps away from Winter Garden’s Plant Street scene — Plant Street Market, Crooked Can Brewing, Award winning Restaurants, Boutique shops, and the 22 mile long West Orange Trail. Enjoy year round festivals, dining, weekly farmers’ markets and nightlife within easy walking distance, plus quick access to major highways and all Orlando’s Theme Parks and attractions. Perfect fit for: Northern snowbirds seeking low-maintenance seasonal living, those starting fresh after a divorce who want an elegant, turnkey sanctuary, or anyone who values design-forward, walkable downtown life. Schedule a tour and see how effortlessly this home fits your next chapter.

129 S Park Avenue Unit 8E, Winter Garden
$225,000
3 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to one of the cutest townhomes in the heart of Downtown Winter Garden! This charming 3 Bedroom, 2 bath home offers the perfect blend of comfort, covenience and one of Central Florida's most sought-after lifestyles. Whether you're a first-time homebuyer, looking to downsize or searching for a fantastic investment opportunity, this home checks all the boxes. Inside, you'll find a functional floor plan with comfortable living spaces, spacious bedrooms and low-maintenance living so you can spend more time enjoying everything the area has to offer. Location is everything, and this one is hard to beat! Just minutes from the award-winning Historic Downtown Winter Garden, you'll love spending weekends exploring the nationally recognized Winter Garden Farmers Market, browsing unique boutiques, enjoying locally owned restaurants, coffee shops, breweries and year-round community events. Living here means embracing the famous Golf Cart District lifestyle. Hop in your golf cart and head downtown for dinner, live music, festivals or an evening stroll along Plant Street. Outdoor enthusiasts will appreciate easy access to the scenic West Orange Trail, offering miles of paved paths for walking, running and biking. Winter Garden continues to be one of Central Florida's most desirable communities thanks to its small-town charm, top-rated amenities, vibrant downtown, and convenient access to major highways, Orlando, world-famous attractions, shopping, dining and entertainment. Whether you're looking for a place to call home or an income-producing property in a highly desirable location, this adorable townhome offers incredible value and endless potential. Don't miss your opportunity to own a piece of the Downtown Winter Garden lifestyle! Schedule your private showing today and discover why so many people are proud to call Winter Garden home.

397 Eron Way Unit 42, Winter Garden
$1,095,000
4 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.

64 N Park Avenue, Winter Garden
$2,999,000
Fries Winter Garden SubDv. ⋅ 34787 Zip Code
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.

18 & 20 E Plant Street, Winter Garden
$1,800,000
Overstreet Crate SubDv. ⋅ 34787 Zip Code
CITY OF WINTER GARDEN HAS APPROVED A NEW OVER LAY ALLOWING 10 UNITS PER GROSS ACRE HIGH DENSITY ZONING~THIS PART OF A BEAUTIFCATION OF EAST WINTER GARDEN AREA MAY ALLOW FOR ADDITTIONAL FINANCIAL INCENTIVES FOR THE DEVELOPER~THE PROPERTY IS 1.8 ACRES, ZONED FOR 10 UNITS PER ACRE, AND IS LOCATED ACROSS FROM THE AUTO AUCTION, ADJACENT TO THE CROWN, CORK AND SEAL, VERY CLOSE TO HIGH TECH INDUSTRIAL PARK, AND NEW APARTMENT COMPLEX OFF OF PLANT STREET. QUICK ACCESS TO THE 429 AND HWY 50, WITHIN 2 MILES FROM DOWNTOWN HISTORIC WINTER GARDEN. PROPERTY IS BEING SOLD "AS IS" SEE ATTACHMENTS FOR MORE INFORMATION~CITY OF WINTER GARDEN WILL LOOK AT DRAWINGS OF DEVELOPMENT PROPOSAL TO APPROVE ANY ZONING CHANGES~HIGHLY DESIRABLE HISTORIC WINTER GARDEN LOCATION~WINTER GARDEN EAST SIDE DEVELOPMENT OVERLAY IN PLACE.

1211 E Maple Street, Winter Garden