$495,000
516 Highland Avenue
Winter Garden, FL 34787
Listing updated: August 31, 2026 at 3:51 PM ET
Listing courtesy of Windsor Realty Group Inc · Lisa Bennett · MLS #O6409675 · Active · 407-877-3463Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
About this home
**Back on the market! Heartbroken Buyer's contingency fell through- New Price to sell **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!
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 history3 days on market
- Status: ActiveAug 31, 2026
- Listed$500,000May 25, 2026
- Price reduced$495,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 3
- Subdivision
- Rep Pt Pleasant Park Sub
- County
- Orange
- Year built
- 1955
- Living area
- 1,716 sq ft
- Price/sq ft
- $288
- Building area
- 2,037 sq ft (Public Records)
- Lot size
- 9,021 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0215H)
- Annual taxes
- $709 (2025)
- Parcel #
- 23-22-27-7156-02-170
- Zoning
- R-2
- MLS #
- O6409675
Ask about this home
Have a question? Ask the broker directly.
Ryan Solberg answers personally — no call center, no spam. Your question goes straight to him.
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Carpet, Ceramic Tile
- Appliances
- Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
- Interior features
- Window Treatments
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- East
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
Parking
- Carport
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer and or Buyer side agent to verify any lease restrictions to their satisfaction with City or County.
Exterior & Construction
- Construction materials
- Block
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Public, Sewer Connected, Water Connected
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 14x13 |
| Family Room | First | 10x15 |
| Kitchen | First | 9x9 |
| Dinette | First | 10x10 |
| Primary Bedroom | First | 12x11 |
| Bedroom 2 | First | 10x10 |
| Bedroom 3 | First | 12x10 |
| Balcony/Porch/Lanai | First | 22x12 |
Listing Details
- Listing date
- 2026-05-25
- On market date
- 2026-05-25
- Original list price
- $500,000
- Occupant type
- Owner
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-08-31
- Tax legal description
- REP PT PLEASANT PARK SUB R/124 LOT 17 BLK B
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
Plant Street Winter Garden to South on S. Highland to #516 on Right.
More homes like this
$549,000
2204 Romanum Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,032 sqft
Alexander Ridge
MLS ID #S5156590, WATSON REALTY CORP..
Listing provided by Stellar MLS
$509,900
1889 Pomegranate Ct
Ocoee, FL 34761
5 bd · 4 ba · 3,856 sqft
Orchard Park 46/76
MLS ID #O6427129, SOUTHERN PRESTIGE REALTY INC.
Listing provided by Stellar MLS
$641,681
13325 Lush Lime Aly
Windermere, FL 34786
3 bd · 3 ba · 1,714 sqft
Lake Cawood Cove
MLS ID #TB8544045, ASHTON WOODS FLORIDA REALTY LLC.
Listing provided by Stellar MLS
$389,000
1708 Creole Ct
Orlando, FL 32818
4 bd · 2 ba · 1,376 sqft
Magnolia Spgs
MLS ID #O6427652, CLOCK TOWER REALTY.
Listing provided by Stellar MLS
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 August 31, 2026 at 3:51 PM 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA