Under contract-accepting backup offers. **DOWNTOWN WINTER GARDEN UPDATED GEM — GOLF CART OR WALK TO PLANT STREET** **THREE BEDROOMS + LARGE FLEX SPACE** **UPDATED KITCHEN & FLOORING** **LARGE FULLY FENCED LOT – NEARLY 1/4 ACRE** **NO HOA – LIVE WITHOUT RULES & RESTRICTIONS** Located just blocks from Plant Street, this updated home welcomes you with a charming front porch, beautiful mature trees and an oversized lot…nearly 1/4 acre & fully fenced. Fantastic & flexible floor plan with three bedrooms PLUS additional large flex space…office, den, gym, play room…endless options. Spacious foyer entry with storage and large living room with solid wood floors. Lots of natural light throughout. FULLY UPDATED KITCHEN in 2022…including cabinets, countertop & appliances. UPDATED TILE & HARDWOOD throughout. Large primary suite with vaulted ceiling, hardwood flooring & spacious ensuite bath with walk-in shower. Live the FLORIDA lifestyle outdoors in the large & private backyard with multiple patio areas, both covered & uncovered. Large storage shed. Long driveway for ample parking space. Zoned R-2. FULLY FENCED. NO HOA…live without rules & restrictions! Enjoy the lifestyle of Central Florida’s most desirable and growing historic downtown…welcome to the GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer’s market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation…come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. DO NOT MISS your opportunity to own this one-of-a-kind dream home & LOCATION! WELCOME HOME!
Property Details
Price:
$518,000
MLS #:
O6451915
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:
Oct 22, 2026
Finished Sq Ft:
1,782
Total Sq Ft:
1,782
Lot Size:
9,018 sqft / 0.21 acres (approx)
Year Built:
1952
See this Listing
Schools
Elementary School:
Dillard Street Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Tile, Hardwood
Heating
Central
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Traditional
Construction Materials
Block
Direction Faces
East
Exterior Features
Lighting, Private Yard, Storage
Fencing
Vinyl
Lot Features
City Lot
Other Structures
Shed(s)
Parking Features
Converted Garage
Patio And Porch Features
Covered, Front Porch, Patio
Roof
Shingle
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$2,147
Map
Community
- Address524 S HIGHLAND AVENUE WINTER GARDEN FL
- SubdivisionREP PT PLEASANT PARK SUB
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Nov 02, 2026
766
Single Family Listed
122
Avg DOM
277
Avg $ / SqFt
$748,546
Avg List Price
Property Summary
- Located in the REP PT PLEASANT PARK SUB subdivision, 524 S HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $518,000 and features 3 beds, 2 baths, and has approximately 1,782 square feet of living space, and was originally constructed in 1952. The current price per square foot is $291. The average price per square foot for Single Family listings in WINTER GARDEN is $277. The average listing price for Single Family in WINTER GARDEN is $748,546. To schedule a showing of MLS#o6451915 at 524 S HIGHLAND AVENUE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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Courtesy of TARA MOORE REAL ESTATE. 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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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. 524 S HIGHLAND AVENUE
WINTER GARDEN, FL