$1,100,000
206 Highland Avenue
Winter Garden, FL 34787
Listing updated: September 30, 2026 at 1:17 AM ET
Listing courtesy of Homevest Realty · Erica Diaz · MLS #O6444632 · Active · 407-897-5400Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage space
Flood zone
About this home
Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.
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 history0 days on market
- Status: ActiveSep 29, 2026
- Listed$1,100,000Sep 29, 2026
- Price increased$1,100,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Cooper & Sewell Add
- County
- Orange
- Year built
- 1925
- Living area
- 1,950 sq ft
- Price/sq ft
- $564
- Building area
- 2,326 sq ft (Public Records)
- Lot size
- 10,488 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- x
- Garage
- 1 spaces
- Annual taxes
- $2,054 (2025)
- Parcel #
- 14-22-27-1728-04-020
- Zoning
- R-2
- MLS #
- O6444632
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Ceramic Tile, Wood
- Appliances
- Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator
- Interior features
- Built-in Features, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- West
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 1
- Attached garage
- No
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Please verify with the City of Winter Garden
Exterior & Construction
- Exterior features
- Lighting
- Construction materials
- Wood Siding
- Roof
- Shingle
- Foundation
- Crawlspace
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Connected, Natural Gas Available, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | |
| Dining Room | First | |
| Living Room | First | |
| Office | First | |
| Primary Bedroom | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Bathroom 2 | First | |
| Bathroom 3 | First | |
| Utility Room | First |
Listing Details
- Listing date
- 2026-09-29
- On market date
- 2026-09-29
- Original list price
- $1,100,000
- Occupant type
- Vacant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-09-29
- Tax legal description
- COOPER & SEWELL ADDITION F/39 LOT 2 BLKD
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
From Plant Street, head north on N Highland. Home will be on the left.
Property sale history
Public records206 N HIGHLAND AVE, Winter Garden 34787
- Jul 2025$490,000
- Mar 2025$380,000
1,950 sq ft · Built 1925 · 0.2408 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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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of September 30, 2026 at 1:17 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
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