About 20 E Division Street
Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!
Features of 20 E Division Street
| MLS® # | O6413659 |
|---|---|
| Price | $1,080,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 3 |
| Square Footage | 2,729 |
| Acres | 0.30 |
| Year Built | 1959 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 20 E Division Street |
|---|---|
| Area | Winter Garden/Oakland |
| Subdivision | WINTER GARDEN SHORES FIRST ADD |
| City | WINTER GARDEN |
| County | Orange |
| State | FL |
| Zip Code | 34787-2312 |
Amenities
| # of Garages | 1 |
|---|---|
| Is Waterfront | No |
| Has Pool | Yes |
Interior
| Interior Features | Eating Space In Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Walk-In Closet(s) |
|---|---|
| Appliances | Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator |
| Heating | Central |
| Cooling | Central Air |
| Fireplace | Yes |
| Fireplaces | Family Room |
Exterior
| Exterior Features | Garden, Private Yard, Rain Gutters, Sauna |
|---|---|
| Roof | Shingle |
| Foundation | Slab |
Additional Information
| Date Listed | June 5th, 2026 |
|---|---|
| Days on Market | 87 |
| Zoning | R-1 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | CHARLES RUTENBERG REALTY ORLANDO |
|---|