Under contract

$500,000

516 S HIGHLAND AVENUE, WINTER GARDEN, FL 34787

3beds

1,716sqft

$3,310/mo

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Single Family Residence

Built in 1955

9,021 Square Feet Lot

$-- Zestimate^®

$291/sqft

$-- HOA

What's special

Spacious laundry roomSolidly built mid-century home

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!

71 days

147

2

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Rooms

Room types: Family Room, Utility Room

Primary bedroom

Features: En Suite Bathroom, Walk-In Closet(s)
Level: First
Area: 132 Square Feet
Dimensions: 12x11

Bedroom 2

Features: Built-in Closet
Level: First
Area: 100 Square Feet
Dimensions: 10x10

Bedroom 3

Features: Built-in Closet
Level: First
Area: 120 Square Feet
Dimensions: 12x10

Balcony porch lanai

Features: No Closet
Level: First
Area: 264 Square Feet
Dimensions: 22x12

Dinette

Level: First
Area: 100 Square Feet
Dimensions: 10x10

Family room

Features: No Closet
Level: First
Area: 150 Square Feet
Dimensions: 10x15

Kitchen

Level: First
Area: 81 Square Feet
Dimensions: 9x9

Living room

Features: No Closet
Level: First
Area: 182 Square Feet
Dimensions: 14x13

Heating

Electric

Cooling

Central Air

Appliances

Included: Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
Laundry: Inside, Laundry Room

Features

Flooring: Carpet, Ceramic Tile
Doors: French Doors
Windows: Blinds, Window Treatments
Has fireplace: No

Interior area

Total structure area: 2,037
Total interior livable area: 1,716 sqft

Video & virtual tour

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Property

Parking

Total spaces: 1
Parking features: Carport
Carport spaces: 1

Features

Levels: One
Stories: 1
Patio & porch: Rear Porch
Exterior features: Irrigation System
Has view: Yes
View description: Garden

Lot

Size: 9,021 Square Feet
Features: City Lot
Residential vegetation: Trees/Landscaped

Details

Additional structures: Shed(s)
Parcel number: 232227715602170
Zoning: R-2
Special conditions: None

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence

Materials

Block
Foundation: Slab
Roof: Shingle

Condition

New construction: No
Year built: 1955

Utilities & green energy

Sewer: Public Sewer
Water: Public
Utilities for property: Cable Connected, Electricity Connected, Public, Sewer Connected, Water Connected

Community & HOA

Community

Pet fee: $0 monthly
Subdivision: REP PT PLEASANT PARK SUB

HOA

Has HOA: No

Location

Region: Winter Garden

Financial & listing details

Price per square foot: $291/sqft
Tax assessed value: $244,264
Annual tax amount: $709
Date on market: 5/25/2026
Cumulative days on market: 31 days
Listing terms: Cash,Conventional
Ownership: Fee Simple
Total actual rent: 0
Electric utility on property: Yes
Road surface type: Paved, Asphalt

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
7/8/2026	Contingent	$500,000$291/sqft
Source: Stellar MLS #O6409675 Report a problem
5/29/2026	Pending sale	$500,000$291/sqft
Source: Stellar MLS #O6409675 Report a problem
5/25/2026	Listed for sale	$500,000$291/sqft
Source: Stellar MLS #O6409675 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2024	$667 +6.4%	$81,706 +3%
2023	$627 +5.8%	$79,326 +3%
2022	$593 +3.4%	$77,016 +3%
2021	$574 +0.1%	$74,773 +1.4%
2020	$573 -0.1%	$73,741 +2.3%
2019	$574 +0.1%	$72,083 +1.9%
2018	$573	$70,739 -39.3%
2017	$573 +1.6%	$116,517 +22.5%
2016	$564 -0.8%	$95,090 +12%
2015	$568 -3.5%	$84,914 +21.3%
2014	$589 +2.2%	$70,003 +6.3%
2013	$576 -0.3%	$65,864 +0.5%
2012	$578 -0.7%	$65,524 -1.8%
2011	$582 +5.8%	$66,758 -6.7%
2010	$550	$71,520 -14.2%
2009	--	$83,373 -21.7%
2008	$487 -14.4%	$106,448 -1.7%
2007	$568 -6.4%	$108,271 +4.5%
2006	$607 +1.8%	$103,588 +6.1%
2005	$596 +6.7%	$97,608 +27.8%
2004	$559 +1.5%	$76,364 +6.5%
2003	$551 +4.5%	$71,683 +7.3%
2002	$527 0%	$66,781 +13.2%
2001	$527 +4.9%	$59,005 +5.9%
2000	$502	$55,727

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Monthly payment

Est. payment

Payment breakdown

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Principal & interest
$1,547
Mortgage insurance
$0
Property taxes
$170
Home insurance
$105
HOA fees
$0
Utilities
Not included

All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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