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$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
$699,000
7 Beds ⋅ 3 Baths ⋅ Burchshire SubDv. ⋅ 34787 Zip Code
ATTENTION INVESTORS! Rare opportunity to own a fully occupied triplex in the heart of Winter Garden. Located within minutes to the popular Plant Street district with its vibrant shops, restaurants, and entertainment. This true triplex sits on an oversized lot and features three renovated units with reliable tenants. Each unit is individually metered for electricity, and the property is connected to city water and city sewer. Tenants pay their own utilities and are responsible for yard maintenance. The oversized lot provides additional flexibility and potential for future expansion such as a garage apartment or in-law suite (buyer to verify zoning and building requirements). Roof replaced approximately 10 years ago. Excellent location with strong long-term appreciation potential.

721 Foster Avenue, Winter Garden
$1,200,000
J S Loveless Add SubDv. ⋅ 34787 Zip Code
Don’t wait to see this income producing property close to downtown Winter Garden! The property is currently zoned commercial. This one story building consists of 8 apartments & each unit is a 2 bed 1 bath 700 ft.² 7 were completely updated two years ago including electrical panels.. New ROOF 2022 plus all new AC units with individual utility bills. 7 of the 8 units are tenant occupied paying $1000- $1200 a month each and are at the end of their lease. Use your imagination and the opportunities are endless.

150 North Street, Winter Garden
$949,000
Un-Incorporated SubDv. ⋅ 34787 Zip Code
Indulge in the epitome of luxury living with this extraordinary Winter Garden Florida estate, a hidden gem sprawling over 1.5 acres. This distinguished property features not just one, but two homes, offering unparalleled privacy and grandeur. The main home is a masterpiece of design and functionality, boasting an oversized pool, perfect for refreshing swims under the sun. Step into the grandeur of the main residence and discover a wealth of amenities, including a giant sunroom, an outdoor patio off the kitchen for al fresco dining, and a grand dining room for entertaining guests in style. The vast walk-in pantry ensures that storage is never a concern, and there's storage space aplenty throughout the estate. The main home's architecture exudes a stately Plantation/Manor style, with French doors throughout creating an elegant and timeless atmosphere. The primary bedroom is truly a retreat, featuring two dressing rooms, walk-in closets the size of bedrooms, and an ensuite bath that exudes luxury. A library provides a quiet space for reading and contemplation. Entertain in style in the party room, complete with a jacuzzi, pool table, skylights, and a built-in bar. Multiple dining and eating areas provide flexibility for various occasions. The estate also features a massive front porch and a large deck attached to the home, both perfect for enjoying the picturesque surroundings. The second home, a two-story guest home, offers additional space and potential. While it requires an interior cosmetic facelift, it presents an opportunity for an income-producing property or an elegant family guest home. The estate's outdoor amenities are equally impressive, with vast land ensuring immense privacy, ample parking, walking trails, and paved paths leading down to the serene lake. The property faces an undeveloped, quiet lake, creating a tranquil backdrop for daily living. For those with a green thumb, the estate features rare and exotic mature vegetation, fruit trees, palms, and a variety of plants that make it a true winter garden jewel. Multiple chicken coops and sheds are scattered throughout, adding to the charm and functionality of this remarkable property. If you've ever dreamed of a large private estate with a pool overlooking a lake, without being too far off the grid, this is an unparalleled find. With its potential for hosting events, weddings, or simply enjoying the tranquility of your own winter garden oasis, this estate is a rare and exceptional opportunity. Don't miss your chance to call this slice of paradise home!

15668 W Colonial Drive, Winter Garden
$165,000
Mary Jean Sub SubDv. ⋅ 34787 Zip Code
Investment Duplex Property.

194 Mary Street, Winter Garden
$783,506
6 Beds ⋅ 4 Baths ⋅ Jewel Heights SubDv. ⋅ 34787 Zip Code
RARE!!! Two duplex property located .5 miles south of Plant Street in Downtown Winter Garden. The duplexes have been well maintained by the current owner and both have been renovated within the past three years. The first duplex consists of two 1/1 units and were renovated in 2023. Both units in this duplex have wall A/C units. The second duplex was renovated in 2020 and consists of 2/1 units. Both units have newer mini split A/C systems. The smaller of the two duplexes is vacant. The larger duplex is currently occupied by longer term tenants and the leases are set to expire on December 31. The rents for the larger duplex are $850 and $950 which are considered to be low for the neighborhood. We estimate that the market rent for the 2/1 units would be around $1,800 and the 1/1 units to be about $1,200. DO NOT CONTACT THE TENANTS OR THE OWNER. THE OWNER REQUESTS THAT ALL COMMUNICATION BE DONE THROUGH THE LISTING AGENTS.

50 W Story Road, Winter Garden