Under contract-accepting backup offers. 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!
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!
Property Details
Price:
$500,000
MLS #:
O6409675
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
REP PT PLEASANT PARK SUB
Neighborhood:
34787wintergardenoakland
Listed Date:
May 25, 2026
Finished Sq Ft:
1,716
Total Sq Ft:
2,037
Lot Size:
9,021 sqft / 0.21 acres (approx)
Year Built:
1955
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Electric
Interior Features
Window Treatments
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Construction Materials
Block
Covered Spaces
1
Direction Faces
East
Exterior Features
French Doors, Irrigation System
Lot Features
City Lot
Other Structures
Shed(s)
Patio And Porch Features
Rear Porch
Roof
Shingle
View
Garden
Window Features
Blinds, Drapes
Financial
Tax Year
2025
Taxes
$709
Map
Community
- Address516 S HIGHLAND AVENUE WINTER GARDEN FL
- SubdivisionREP PT PLEASANT PARK SUB
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 29, 2026
825
Single Family Listed
112
Avg DOM
279
Avg $ / SqFt
$758,420
Avg List Price
Property Summary
- Located in the REP PT PLEASANT PARK SUB subdivision, 516 S HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $500,000 and features 3 beds, 2 baths, and has approximately 1,716 square feet of living space, and was originally constructed in 1955. The current price per square foot is $291. The average price per square foot for Single Family listings in WINTER GARDEN is $279. The average listing price for Single Family in WINTER GARDEN is $758,420. To schedule a showing of MLS#o6409675 at 516 S HIGHLAND AVENUE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of WINDSOR REALTY GROUP INC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 516 S HIGHLAND AVENUE
WINTER GARDEN, FL