20 E DIVISION STREET
Winter Garden, FL 34787
$995,000
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!!!
Listing Courtesy of: CHARLES RUTENBERG REALTY ORLANDO
407-622-2122
| Listing Id: | O6413659 |
|---|---|
| List Price: | $995,000 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Active |
| Bedrooms Total: | 4 |
| Bathrooms Full: | 3 |
| Living Area: | 2,729 |
| Tax Annual Amount: | $7,197 |
| Lot Size Square Feet: | 12,982 |
| Lot Size Acres: | 0.3 |
| Waterfront?: | No |
| City: | Winter Garden |
| County Or Parish: | Orange |
| Subdivision Name: | Winter Garden Shores First Add |
| Postal Code: | 34787 |
| Year Built: | 1959 |
| Appliances: | Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 3 |
| Building Area Source: | Public Records |
| Building Area Total: | 3435 |
| Building Area Units: | Square Feet |
| Direction Faces: | North |
| Foundation Details: | Slab |
| Construction Materials: | Concrete |
| Cooling: | Central Air |
| Fireplace Features: | Family Room |
| Directions: | Dillard street turn left onto E Division street, home is on your left. |
| Exterior Features: | Garden, Private Yard, Rain Gutters, Sauna |
| Flooring: | Luxury Vinyl, Marble, Tile |
| Furnished: | Unfurnished |
| Garage Spaces: | 1 |
| Garage?: | Yes |
| Heating: | Central |
| Interior Features: | Eat-in Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Walk-In Closet(s) |
| Laundry Features: | Laundry Room |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Appraiser |
| Living Area Units: | Square Feet |
| Lot Size Acres: | 0.3 |
| Postal Code Plus4: | 2312 |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| Original List Price: | $1,149,000 |
| Other Equipment: | Private Yard |
| Parcel Number: | 14-22-27-9388-01-010 |
| Pool Features: | In Ground |
| Township: | 22 |
| Road Surface Type: | Asphalt |
| Roof: | Shingle |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | Cable Available, Electricity Available |
| Water Source: | Public |
| Property Condition: | Completed |
| Public Survey Range: | 27 |
| Public Survey Section: | 14 |
| Zoning: | R-1 |
| Window Features: | Shutters |
| Additional Lease Restrictions: | Buyer agent to verify with county records |
| Alternate Key Folio Num: | 14-22-27-9388-01-010 |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 319.12 |
| Calculated List Price By Calcula: | 364.60 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6413659?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6413659?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2021-09-24 |
| Flood Zone Panel: | 12095C0205H |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | No |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 253.53 |
| Lot Size Square Meters: | 1206 |
| Minimum Lease: | No Minimum |
| Property Description: | Corner Unit |
| Room Count: | 3 |
| Sdeo yn: | No |
| Total Acreage: | 1/4 to less than 1/2 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-622-2122 |
| Originating System Name : | Stellar MLS |
| Dock Yn: | No |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-06-03 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
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Property Last Updated: October 21, 2026 12:15 AM - ET
