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251 N Plant Street, Winter Garden
$699,000
4 Beds ⋅ 4 Baths ⋅ J L Dillard Sub SubDv. ⋅ 34787 Zip Code
Prime Winter Garden Duplex in the Golf Cart District | Updated | Income-Producing!! Discover a rare opportunity to own a duplex in the heart of Winter Garden, ideally positioned within the coveted Golf Cart District and directly off the West Orange Trail. Both units are currently leased, offering immediate rental income and an attractive investment opportunity in one of Central Florida’s most sought-after communities. ROOF 2022 & whole duplex REPIPE in 2024. The location is truly the standout feature—enjoy easy access to the West Orange Trail for biking, walking, and outdoor recreation, while the golf-cart-friendly setting makes it convenient to cruise to nearby shopping, dining, entertainment, and the charming downtown Winter Garden area. Located in the heart of the vibrant Winter Garden community, residents can enjoy local restaurants, boutique shopping, weekend events, farmers markets, and the area's popular downtown atmosphere, all while being surrounded by established neighborhoods and recreational amenities. With convenient access to major roadways, the property also provides an easy commute to Orlando and the surrounding attractions. Whether you're looking to expand your investment portfolio or secure a well-positioned income-producing property in Winter Garden, this duplex offers an exceptional combination of location, lifestyle, and rental potential. Both sides are currently tenant occupied—an excellent opportunity to own a turnkey duplex in a highly desirable area. Please do not disturb tenants.

251 N Plant Street, Winter Garden
402 E Maple Street, Winter Garden
$825,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Rare dual-income opportunity with no HOA, located minutes from historic Downtown Winter Garden. Built in 2021 on an oversized corner lot, this high return opportunity, turn-key property offers two complete, self-contained residences designed for optimal rental income, multi-generational living, or an effortless house hack where the neighboring tenant covers your mortgage. Each residence features its own street frontage, private entrance, separate driveway, and dedicated two-car attached garage for complete tenant privacy and independence—four garage bays total. Across both mirrored units, the home encompasses 2,876 heated square feet, totaling six bedrooms, four full bathrooms, and two powder baths, offering three bedrooms and two and a half bathrooms on each side. The main levels highlight spacious open-concept living and dining areas, well-appointed kitchens, and convenient half baths for guests. Upstairs, each unit features a private primary suite with a walk-in closet and en suite bath, alongside two generous guest bedrooms, a second full bathroom, and dedicated laundry space. Durable hard-surface flooring throughout ensures low turnover costs and easy maintenance. Tenants and owners alike will love being within walking and golf cart distance of Plant Street dining, boutique shopping, local breweries, the West Orange Trail, and the Saturday Farmers Market, while enjoying quick commuter access to SR-429, SR-50, and the Florida Turnpike. Modern, high-cash-flow multi-door assets in this prime Winter Garden corridor are exceptionally rare. Schedule your private showing today.

402 E Maple Street, Winter Garden
208 3rd Street, Winter Garden
$435,000
Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
Most Winter Garden listings sell on charm. This one sells on the rent roll. Eight rooms currently rented — seven at $175 weekly and one at $200 — generating $1,425 per week / $74,100 annualized gross income at current rents. In place, occupied, and income producing. The land adds another layer to the opportunity. Situated on approximately 0.22 acres / 9,500+ SF with a 75' x 125' lot, the fully fenced property offers R-2 zoning, no HOA, city water and city sewer, along with ample yard space and future flexibility. Hold the existing income while exploring the property's longer-term expansion or redevelopment potential, subject to applicable zoning requirements and City approvals. The location carries its own value. Just a few blocks from Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shops, restaurants and the farmers market, with SR-429, Florida's Turnpike and Lake Apopka nearby. The surrounding area continues to evolve with renovated properties and new construction. 0.22 Acres. 9,500+ SF Lot. R-2. Eight Rented Rooms. $1,425/Week Gross. Income in place. Land underneath. Future upside ahead. A rare opportunity to own all three near Downtown Winter Garden—schedule your private showing today.

208 3rd Street, Winter Garden
15992 W Colonial Drive, Oakland
$3,200,000
41 Beds ⋅ 75 Baths ⋅ Lake Johns Motel Apts. & Tr. Pk SubDv. ⋅ 34787 Zip Code
15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily Opportunity Exceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland. Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style residences, mobile home/RV units, and additional rental pads, creating multiple income streams and long-term upside. Currently generating $34,860 per month in gross rental income the property delivers immediate cash flow while offering significant future value-add and redevelopment potential. Located just minutes from the Florida Turnpike interchange, Downtown Winter Garden, Clermont, and the greater Orlando employment hubs, this site sits directly in the path of West Orange’s continued expansion. The C-1 zoning and strategic frontage on SR-50 make this an especially compelling opportunity for investors seeking stable income today with the flexibility for future repositioning. Whetherd workforce housing and RV income asset, repositioned into a boutique rental community, or held for future redevelopment, opportunities with this combination of location, scale, frontage, and in-place revenue are increasingly rare. (Seller is selling 112 units in total varying in diffrent locations this is 32 of those 112)

15992 W Colonial Drive, Oakland
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