$1,120,000
20 Division Street
Winter Garden, FL 34787
Listing updated: June 26, 2026 at 8:18 AM ET
Listing courtesy of Charles Rutenberg Realty Orlando · Liz Boyce · MLS #O6413659 · Active · 407-622-2122Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage space
Flood zone
About this home
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!!!
Local Insight
At $410/sqft for a 1959 home in a rapidly growing area (population expected to jump from 58K to 73K in just a few years), you're paying market-rate for the location and potential rather than the vintage of the house itself—the pool and no HOA are selling points, but that price assumes the bones hold up under inspection. Winter Garden Shores First Add is an older, established neighborhood in unincorporated Orange County with stable appeal, though you should verify whether future development or infrastructure changes in this booming CDP could affect your quiet street. The lack of flood risk (Zone X) and relatively modest lot size (0.3 acres) are typical for the area, so focus your due diligence on the actual condition of that 1959 structure and whether the pool and fireplace justify the premium over comparable newer homes nearby.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history21 days on market
- Status: ActiveJun 5, 2026
- Listed$1,149,000Jun 5, 2026
- Price reduced$1,120,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 21
- Subdivision
- Winter Garden Shores First Add
- County
- Orange
- Year built
- 1959
- Living area
- 2,729 sq ft
- Price/sq ft
- $410
- Building area
- 3,435 sq ft (Public Records)
- Lot size
- 12,982 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0205H)
- Garage
- 1 spaces
- Pool
- Private pool
- Annual taxes
- $7,197 (2025)
- Parcel #
- 14-22-27-9388-01-010
- Zoning
- R-1
- MLS #
- O6413659
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Luxury Vinyl, Marble, Tile
- Appliances
- Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Eat-in Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Walk-In Closet(s)
- Laundry
- Laundry Room
- Stories / Levels
- One
- Direction faces
- North
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 1
- Attached garage
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer agent to verify with county records
Exterior & Construction
- Exterior features
- Garden, Private Yard, Rain Gutters, Sauna
- Construction materials
- Concrete
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Available
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 42.5x13.2 |
| Kitchen | First | 17x12.9 |
| Primary Bedroom | First | 17x12.9 |
Listing Details
- Listing date
- 2026-06-03
- On market date
- 2026-06-05
- Original list price
- $1,149,000
- Occupant type
- Vacant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-05
- Tax legal description
- WINTER GARDEN SHORES FIRST ADDITION T/86LOT 1 BLK A
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
Dillard street turn left onto E Division street, home is on your left.
Property sale history
Public records20 E DIVISION ST, Winter Garden 34787
- Jul 2024$750,000
2,729 sq ft · Built 1959 · 0.2980 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
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Based on information submitted to the MLS GRID as of June 26, 2026 at 8:18 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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