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$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

93 Windtree Lane Unit 102, Winter Garden
$900,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Rare opportunity to own a unique corner-lot property featuring two attached residences, each with its own street frontage, private entrance, covered front porch, two-car garage, no HOA, and identical floor plan. Unlike a traditional side-by-side duplex, each residence faces a different street, creating the appearance and feel of two individual homes while offering the convenience of a connected design. Designed for both comfort and flexibility, each home features a spacious living and dining area, a bright kitchen with French doors leading to the backyard, and a convenient first-floor guest powder bath. Upstairs, all bedrooms are thoughtfully positioned for added privacy. The primary suite includes a private ensuite bath, while the secondary bedrooms are generously sized and complemented by abundant storage throughout each residence. The Wilson Street residence has been thoughtfully upgraded with luxury vinyl flooring, an enhanced kitchen with stone counters and gas cooking, beautifully updated bathrooms, and an attractive staircase that adds character and style. The Maple Street residence has been a consistently popular rental and has been exceptionally maintained, offering a spotless interior that reflects pride of ownership. The location offers exceptional convenience with nearby access to Downtown Winter Garden, one of Central Florida’s most sought-after destinations. Enjoy a vibrant mix of locally owned restaurants, cafés, boutiques, specialty shops, the award-winning Winter Garden Farmers Market, seasonal festivals, live entertainment, and the renowned West Orange Trail. The property also provides convenient access to the Florida State Road 429, Florida State Road 408, and Florida’s Turnpike, making travel throughout Central Florida simple. Popular destinations, including Winter Garden Village, Walt Disney World Resort, major employment centers, shopping, dining, entertainment, parks, and everyday conveniences, are all nearby. Whether you’re seeking a property that offers exceptional flexibility for evolving lifestyle needs, the opportunity to generate rental income, or the convenience of two complete residences under one roof, this distinctive property delivers a rare combination of privacy, functionality, and long-term versatility. Opportunities like this are seldom available, especially with a layout that allows each residence to maintain its own identity while remaining connected.

402 E Maple Street, Winter Garden
$289,000
2 Beds ⋅ 2 Baths ⋅ Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.

1701 E Bay Street, Winter Garden
$410,000
3 Beds ⋅ 2 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

420 E Cypress Street, Winter Garden
$339,000
2 Beds ⋅ 2 Baths ⋅ East Garden Manor Add 03 SubDv. ⋅ 34787 Zip Code
Seller its offering $6,000 for buyers closing costs. Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roof, new plumbing, close to major roads, schools, minutes to Winter Garden dawn town.

483 Pennsylvania Avenue, Winter Garden
$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 03 SubDv. ⋅ 34787 Zip Code
Large Price Improvement. Downstair location, peace and ease with this updated 2/2 FIRST FLOOR condo in Winter Garden. You will love this condo placement in the rear of the community near the pond with fountain, community pool, rentable clubhouse, basketball courts and NO STAIRS. Enjoy the private setting while sitting on your screened porch with your favorite book or beverage and the frequent visits from the neighborhood ducks. The condo has been updated to include the cabinets, counters, updated bathrooms and tile floors throughout. Move in ready so just grab your things and come on. What's Nearby? ANYTHING you could need or want. Only 1.5 miles from downtown Winter Garden, 2.5 miles to Winter Garden Village, 15 miles to Walt Disney World® and other theme parks, 24 miles to MCO Orlando's International Airport/Brightline highspeed passenger train and just over an hour to dip your toes in salty water and sand on Florida's World Famous Beach in Daytona. Downstair units with perfect location do not come around often so book your private tour today and ask your REALTOR for the video walk through link.

87 Windtree Lane Unit K, Winter Garden
$218,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 03 SubDv. ⋅ 34787 Zip Code
Don’t miss this great investment opportunity in the heart of Winter Garden. This 2-bedroom, 2-bath condo offers laminated floors and is already rented, generating income from day one. Home features updated plumbing with a complete repipe. Located just minutes from Downtown Winter Garden, with easy access to restaurants, shops, parks, and major highways. Not a gated community, offering easy access and low-maintenance living. Perfect for investors seeking a stable, income-producing property.

92 Windtree Lane Unit 201, Winter Garden