Off market mar 2019 for $832K

$1,548,836

Est. refi paymentEst. refi $4,607/mo

•

3,058

sq ft

1590 Highland Rd, Winter Park, FL 32789

About this home

Beautiful 4 Bedroom, 3.5 Bath + Office Pool Home in Winter Park! Highly Desirable Location in Virginia Heights with neighborhood access to Lake Virginia. Brand New Roof was just installed in July 2018, this home is a must see! Price to sell this ½ acre lot sits high in one of Winter Park’s best neighborhoods and is ideal for future building or is perfect for the buyer looking to do a little renovation and add their own personal touches to a home. Interior layout is open and spacious. Charming character greets you as you walk in the front door; hardwood floors, crown moldings, plantation shutters, fireplace and more. Formal living and family room off the kitchen. Front office has a half bath and could be used as an optional 5th bedroom. Master suite has an extended foyer-like entrance with a set of French doors that opens to the lanai. Hands down the best part of this home is the amazing backyard. Covered patio, outdoor kitchen with grill all overlooking the pool and oversized fenced backyard. Located on a half-acre of land the backyard is beautifully complimented by tropical landscaping and mature oak and pine trees. Located just a short walk to Rollins College and Park Avenue you’re just minutes from fine restaurants and boutique shops as well as zoned for the brand new Audubon K-8 school.

Single-familyProperty Type

1948Year Built

0.46 acresLot Size

$506Est. Price/Sq.Ft.

2 car garageParking

Listed by Kelly Price • KELLY PRICE & COMPANY LLC

Bought with Suzanne Tellam • FLORIDA ONE REAL ESTATE LLC

Redfin checked: a minute ago

•Source:Stellar MLS as Distributed by MLS Grid #O5734056

Redfin Estimate

$1,548,836

$717K since sold in March 2019$186K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.5% lower than the average sale price ($2.08M) of 6 comparable homes.

SOLD JUN 22, 2026
$1,295,100
A
Land— sq ft
220 W Reading Way, Winter Park, FL 32789
SOLD JUN 1, 2026
$4,250,000
B
4 beds4 baths3,181 sq ft
1336 College Pt, Winter Park, FL 32789
SOLD JUL 31, 2026
$1,825,000
C
5 beds3.5 baths2,976 sq ft
1500 Nottingham St, Orlando, FL 32803
SOLD DEC 29, 2025
$1,589,000
D
4 beds3 baths2,785 sq ft
1450 Glencoe Rd, Winter Park, FL 32789
SOLD DEC 10, 2025
$1,750,000
E
4 beds3.5 baths2,907 sq ft
1513 Nottingham St, Orlando, FL 32803
SOLD SEP 3, 2026
$1,770,000
F
4 beds3.5 baths3,815 sq ft
2410 Lake Shore Dr, Orlando, FL 32803

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$895,848

Est. take-home

List your home with Redfin and save $15,488

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,733/mo

Redfin rental estimate

List your home for rent

Market trends in 32789, FL

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

96.3%

+0.2% MoM

Median sale price

$1.0M

$135K MoM

Avg. days on market

46d

10 days MoM

Recently sold homes

147

6 MoM

New listings for sale

NEW 7 HRS AGO
$350,000
3 beds2 baths1,344 sq ft
310 Granada Dr, Winter Park, FL 32789
$850,000
3 beds2 baths1,639 sq ft
100 S Interlachen Ave #401, Winter Park, FL 32789
COMING SOON
$774,000
2 beds1.5 baths897 sq ft
640 N Park Ave #3, Winter Park, FL 32789
3D WALKTHROUGH
$169,900
1 bed1 bath645 sq ft
2500 Lee Rd #123, Winter Park, FL 32789
$290,000
2 beds2.5 baths1,133 sq ft
188 Sandlewood #1, Winter Park, FL 32789
$448,000
3 beds1 bath1,304 sq ft
712 Baffie Ave, Winter Park, FL 32789
$850,000
4 beds3 baths2,301 sq ft
870 N Phelps Ave, Winter Park, FL 32789
VIDEO TOUR
$950,000
3 beds2.5 baths1,957 sq ft
1256 S Pennsylvania Ave #9, Winter Park, FL 32789
$140,000
2 beds1 bath881 sq ft
1695 Lee Rd Unit C206, Winter Park, FL 32789
3D WALKTHROUGH
$265,000
2 beds2 baths908 sq ft
1250 S Denning Dr #119, Winter Park, FL 32789
See all

Provided by Redfin

Sale history for 1590 Highland Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5734056

Mar 6, 2019

Sold

$832,000

$272/sq ft

Feb 4, 2019

Pending

—

Jan 29, 2019

Price Changed

$860,000

$281/sq ft

Oct 23, 2018

Price Changed

$885,000

$289/sq ft

Sep 14, 2018

Listed

$925,000

$302/sq ft

Stellar MLS as Distributed by MLS Grid #O5558484

May 23, 2018

Listing Removed

—

Public Records

Apr 4, 2000

Sold

$500,000

$164/sq ft

Public Records

Feb 2, 1998

Sold

$439,500

$144/sq ft

Public Records

Jun 1, 1977

Sold

$47,800

$16/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$14,259 (+3.3%)

2024

$13,804 (+3.8%)

2023

$13,293 (+6.8%)

2022

$12,451 (+1.0%)

2021

$12,325 (+1.2%)

2020

$12,178 (+68.8%)

$630,000 + $190,780

$820,780

2019

$7,212 (+0.6%)

2018

$7,173 (−37.1%)

2017

$11,404 (+63.8%)

$507,000 + $172,529

$679,529

2016

$6,964 (−2.3%)

$507,000 + $172,529

$679,529

2015

$7,131 (−0.8%)

2014

$7,192 (−1.5%)

2013

$7,305 (−0.7%)

2012

$7,358

Tax history for 1590 Highland Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,259 (+3.3%)

2024

$13,804 (+3.8%)

2023

$13,293 (+6.8%)

2022

$12,451 (+1.0%)

2021

$12,325 (+1.2%)

2020

$12,178 (+68.8%)

$630,000 + $190,780

$820,780

2019

$7,212 (+0.6%)

2018

$7,173 (−37.1%)

2017

$11,404 (+63.8%)

$507,000 + $172,529

$679,529

2016

$6,964 (−2.3%)

$507,000 + $172,529

$679,529

2015

$7,131 (−0.8%)

2014

$7,192 (−1.5%)

2013

$7,305 (−0.7%)

2012

$7,358

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.46 Acres

Year renovated

1958

Sq. Ft.

3,058

Year built

1948

Style

Single Family Residential

County

Orange County

APN

302207890815090

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

R-1AA \N

Residential District

These districts are established within the city to provide areas for single-family dwellings and necessary accessory buildings. The regulations enumerated for this district are designed to encourage and promote the construction of and the continued use of the land for single-family dwellings, to promote and encourage a suitable environment for family life, to prohibit uses of the land which would substantially interfere with development or continuation of single-family dwellings in the districts, and to prevent use of the land for purposes which would overburden the public facilities. Permitted as conditional uses within these districts will be certain structures and uses required to serve the residents such as public schools, churches and noncommercial recreational uses. Areas zoned for R-1AA districts shall be those existing low-density residential areas plus certain undeveloped areas which should develop in a similar manner according to the comprehensive plan.

Permitted uses

Include but are not limited to:

Housing-Single unit

Property details

Parking

Parking Information
Garage Dimensions: 20x20
Parking Features: Circular Driveway, Garage Faces Rear, Garage Faces Side
Garage Spaces: 2
Has Attached Garage
Has Garage

Interior

Bedroom Information
# of Bedrooms: 4

Bathroom Information
# of Full Baths (Total): 3
# of Half Baths (Total): 1

Other Rooms Information
Additional Rooms: Den/Library/Office,Family Room,Formal Living Room Separate,Inside Utility
# of Rooms: 8

Fireplace Information
Has Fireplace

Heating & Cooling
Heating Information: Electric
Cooling Information: Central Air

Interior Features
Interior Features: Crown Molding, Solid Surface Counters
Window Features: Blinds
Appliances: Built-In Oven, Cooktop, Dishwasher, Microwave, Refrigerator
Flooring: Carpet, Wood

Exterior

Building Information
Construction Materials: Block, Stucco
Roof: Shingle

Exterior Features
Patio And Porch Features: Covered, Patio
Exterior Features: Fence, French Doors, Outdoor Kitchen

Pool Information
Has Private Pool
Pool Features: In Ground

Waterfront Information
Water Body Name: LAKE VIRGINIA
Waterfront Feet Total: 0
Water View Y/N: 0
Water Access Y/N: 1
Water Access Description: Lake,Lake - Chain of Lakes
Water Extras Y/N: 0

Property Information
CDD Y/N: 0
Homestead Y/N: 1
Property Type: Residential
Property Sub Type: Single Family Residence
Other Structures: Outdoor Kitchen
Zoning: R-1AA

Land Information
Vegetation: Mature Landscaping, Trees/Landscaped
Total Acreage: 1/4 Acre to 21779 Sq. Ft.

Lot Information
Lot Features: City Limits, Oversized Lot, Paved
Lot Size Acres: 0.46
Lot Size Dimensions: 100x200

Financial

Tax Information
Tax Annual Amount: $7,173
Tax Year: 2018

Lease / Rent Details
Lease Restrictions YN: 0

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: Electricity Connected

Location

Multi-Unit Information
Unit Number YN: 0

HOA Information
Association Fee Requirement: None
Association Approval Required Y/N: 0

School Information
High School: Winter Park High

Location Information
Directions: From Fairbanks: East on Pennsylvania. Left on Highland. Home is on the right.

Community Information
Community Features: Water Access
Pets Allowed: Yes

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 3,058
Stories: 1.0
Lot Size: 0.46 acres
Style: Single Family Residential
Year Built: 1948
Year Renovated: 1958
County: Orange County
APN: 302207890815090

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 0

Listing Information
Previous Status: Pending
Backups Requested YN: 1
Home Warranty YN: No

Listing Date Information
Days to Contract: 142
Status Contractual Search Date: 2019-03-06

Listing Price Information
Calculated List Price By Calculated Sq Ft: 281.23

Home Information
Living Area: 3058
Living Area Source: Public Records
Building Area Total: 4023
Building Area Source: Public Records
Foundation Details: Slab
Levels: One

Around this home

Schools

AUDUBON PARK SCHOOL

Public PreK-8 • Assigned • 1.2mi

10/10

Winter Park High School

Public 9-12 • Assigned • 1.6mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

9/10 Heat Factor

7 days above 107° expected this year, 22 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winter Park, FL • 32789

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 6.7 hours in December, placing it above the U.S. average for solar exposure.

8.6 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.47M – $1.78M

Reach more buyers when you sell with Redfin. Save up to $15,488 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$589,000

4 beds2 baths1,588 sq ft

212 E Harvard St, Orlando, FL 32804

$530,000

4 beds2 baths1,453 sq ft

2014 Linda St, Orlando, FL 32803

$479,000

3 beds2 baths1,498 sq ft

1652 Berkshire Ave, Winter Park, FL 32789

VIDEO TOUR

$1,275,000

3 beds2.5 baths1,329 sq ft

240 Killarney Dr, Winter Park, FL 32789

$589,999

3 beds3 baths1,650 sq ft

1417 Belgrade Ave, Orlando, FL 32803

VIDEO TOUR

$1,250,000

4 beds1 bath1,260 sq ft

230 Killarney Dr, Winter Park, FL 32789

New listings for sale in 32789

NEW 7 HRS AGO

$350,000

3 beds2 baths1,344 sq ft

310 Granada Dr, Winter Park, FL 32789

$850,000

3 beds2 baths1,639 sq ft

100 S Interlachen Ave #401, Winter Park, FL 32789

COMING SOON

$774,000

2 beds1.5 baths897 sq ft

640 N Park Ave #3, Winter Park, FL 32789

3D WALKTHROUGH

$169,900

1 bed1 bath645 sq ft

2500 Lee Rd #123, Winter Park, FL 32789

$290,000

2 beds2.5 baths1,133 sq ft

188 Sandlewood #1, Winter Park, FL 32789

$448,000

3 beds1 bath1,304 sq ft

712 Baffie Ave, Winter Park, FL 32789

$850,000

4 beds3 baths2,301 sq ft

870 N Phelps Ave, Winter Park, FL 32789

VIDEO TOUR

$950,000

3 beds2.5 baths1,957 sq ft

1256 S Pennsylvania Ave #9, Winter Park, FL 32789

$140,000

2 beds1 bath881 sq ft

1695 Lee Rd Unit C206, Winter Park, FL 32789

Home values near 1590 Highland Rd

Data from public records.

Address	Redfin Estimate
1520 Highland Road, Winter Park, FL 5 Beds \| 6 Baths \| 4720 Sq. Ft.	$2,792,320
1583 Highland Road, Winter Park, FL 3 Beds \| 3 Baths \| 2502 Sq. Ft.	$1,174,705

Address	Redfin Estimate
1599 Highland Road, Winter Park, FL 2 Beds \| 3 Baths \| 2443 Sq. Ft.	$996,438
1541 Highland Road, Winter Park, FL 3 Beds \| 2 Baths \| 2330 Sq. Ft.	$1,321,731

Address	Redfin Estimate
1551 Highland Road, Winter Park, FL 3 Beds \| 2 Baths \| 1689 Sq. Ft.	$999,143
1521 Highland Road, Winter Park, FL 4 Beds \| 3 Baths \| 3418 Sq. Ft.	$1,354,306

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2018. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

32803 homes for sale
32804 homes for sale
32789 homes for sale
32792 homes for sale
32751 homes for sale

Houses for rent in Winter Park	Agents near me	Sarasota, FL homes for sale	Winter Park Housing Market
Houses for sale near me	Orlando, FL homes for sale	Fort Lauderdale, FL homes for sale
Land for sale near me	Tampa, FL homes for sale	Boca Raton, FL homes for sale
Open Houses near me	Miami, FL homes for sale	Winter Park Property Records
Condos for sale near me	Jacksonville, FL homes for sale	FL New Listings

Orlando homes for sale
Kissimmee homes for sale
Winter Garden homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 32789, FL

Sale history for 1590 Highland Rd

Tax history for 1590 Highland Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 32789

Home values near 1590 Highland Rd

More real estate resources