Date
Details
Price
Change
Source
5/25/2026
Listed
$500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/19
$500,000 Just Listed
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1/19
Property Description
Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to Newton Park to catch breathtaking sunsets over Lake Apopka. Hard to find, timeless charm and well maintained! Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind. Rare opportunity to own a one owner (since the 60's) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!
Full Property Details
Full Property Details for 516 S Highland Ave
General
- Price: $500,000
- Taxes: $709 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6409675
- Updated: 5/25/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 8
- Interior Features: Window Treatments
- Appliances: Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
- Furnishings: Partially
- Flooring: Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Exterior
- Exterior Features: French Doors, Irrigation System
- Deck/Patio: Rear Porch
- Porch/Patio/Deck: Rear Porch
Parking
- Carports: Yes
- Carport: 1
- Carport Spaces: 1
- Covered Spaces: 1
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: REP PT PLEASANT PARK SUB
- Driving Directions: Plant Street Winter Garden to South on S. Highland to #516 on Right.
- Direction Faces: East
Community
- Community Name: 34787 - Winter Garden/Oakland
- Pet Restrictions: Buyer and or Buyer side agent to verify to their satisfaction with City or County.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Public, Sewer Connected, Water Connected
Structural Information
- Exterior Const.: Block
- Roof: Shingle
- Windows: Blinds, Drapes
- Stories/Levels: One
- Square Feet: 1,716
- Sq. Ft. Source: Public Records
- Year Built: 1955
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Property View: Garden
- Lot Size (Acres): 0.21
- Lot Size (Sq. Ft.): 9,021
- Lot Size: 9021
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Financial Considerations
- Tax Amount: $709.35
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: REP PT PLEASANT PARK SUB R/124 LOT 17 BLK B
- Flood Zone Info: X
- APN: 232227715602170
- Property ID: 232227715602170
- Block/Lot/Section: B
Listed by Windsor Realty Group Inc
We Value Your Privacy
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We Value Your Privacy
Listing agent
— 516 S Highland Ave —
Windsor Realty Group Inc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 516 S Highland Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.9 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 516 S Highland Ave
Tax History
Tax History for 516 S Highland Ave
Year
Property Taxes
Change
Tax Assessment
Change
2025
$709
6%
$86,345
6%
2024
$667
6%
$81,706
3%
2023
$627
9%
$79,326
6%
2021
$574
-3%
$74,773
-3%
2022
$593
3%
$77,016
4%
2021
$574
—
$73,741
2%
2019
$574
—
$72,083
2%
2018
$573
2%
$70,739
2%
2017
$564
-1%
$69,284
2%
2016
$568
-2%
$67,859
1%
2015
$582
-1%
$67,387
1%
2014
$589
2%
$66,852
2%
2013
$576
—
$65,864
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 516 S Highland Ave
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516 S Highland Avenue, Winter Garden, FL 34787 (MLS# O6409675) is a Single Family property with 3 bedrooms and 2 full bathrooms. 516 S Highland Avenue is currently listed for $500,000 and was received on May 25, 2026. Want to learn more about 516 S Highland Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.