Off Market Jan 2016 for $720K

$1,363,980

Est. refi paymentEst. refi $5,692/mo

•

2,588

sq ft

1508 Highland Rd, Winter Park, FL 32789

About this home

Fabulous 1920's Dutch Colonial nestled in prime Olde Winter Park setting walking distance to Park Ave / Downtown Winter Park. .. This New England style home is elevated from street level on beautiful oversized 1/3 acre corner lot. .. Current owner has restored home with historic style and added some modern updates/finishes. .. 4 BE home including a detached private guest cottage or wonderful home office, Bright-open floor plan with tremendous character & charm await you from the moment you step into the foyer. .. Features include original smooth plaster walls, high ceilings, generous living areas, exquisite hardwood floors, French doors, period lighting, extensive moldings & true craftsmanship, plantation shutters, oversized brick masonry fireplaces in main living room and original master bedroom. .. Main level includes kitchen, mud room, formal dining room, living room with fireplace, primary master bedroom, sun room & lovely screened porch overlooking serene fabulous northern style back yard with flagstone patio area for outdoor entertaining. .. Recent enhancements include a lot of "TLC", complete new paint in/out, refinished hardwood floors, updated baths, upgraded electrical, new plumbing, new ac systems, refurbished some windows, all new landscaping and more! Also, deeded access to park on Lk Virginaia with amazing sunset & Rollins College views w/ kayak/canoe storage. .. must see to appreciate breathtaking Old Florida home that could easily be found in Nantucket as well!

Single-familyProperty Type

1923Year Built

0.33 acresLot Size

$527Est. Price/Sq.Ft.

1 car garageParking

Listed by Mick Night • COLDWELL BANKER REALTY

Listed by John Pinel • COLDWELL BANKER REALTY

Contact: 407-647-1211

Bought with Melissa Woodman • FANNIE HILLMAN & ASSOCIATES

Redfin checked: a minute ago

•Source:Stellar MLS as Distributed by MLS Grid #O5376880

Redfin Estimate

$1,363,980

$644K since sold in January 2016$34K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 28.9% lower than the average sale price ($1.92M) of 6 comparable homes.

SOLD AUG 31, 2026
$2,300,000
A
3 beds3.5 baths3,750 sq ft
3041 Westchester Ave, Orlando, FL 32803
SOLD JUN 1, 2026
$4,250,000
B
4 beds4 baths3,181 sq ft
1336 College Pt, Winter Park, FL 32789
SOLD JUN 22, 2026
$1,295,100
C
Land— sq ft
220 W Reading Way, Winter Park, FL 32789
SOLD SEP 3, 2026
$960,375
D
3 beds2.5 baths2,304 sq ft
241 W Lake Sue Ave, Winter Park, FL 32789
SOLD DEC 29, 2025
$1,589,000
E
4 beds3 baths2,785 sq ft
1450 Glencoe Rd, Winter Park, FL 32789
SOLD AUG 28, 2026
$1,115,000
F
4 beds2 baths2,750 sq ft
1981 Blue Ridge Rd, Winter Park, FL 32789

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Earn from this home

Sell

$840,603

Est. take-home

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Refinance

Est. cash available

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Rent

$4,290/mo

Redfin rental estimate

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Market trends in 32789, FL

Last updated August 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

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OPEN SUN, 12PM TO 2PM
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VIDEO TOUR
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OPEN TODAY, 1PM TO 3PM
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OPEN TODAY, 2PM TO 4PM
$2,195,000
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$1,300,000
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See all

Provided by Redfin

Sale history for 1508 Highland Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5376880

Jan 25, 2016

Sold

$720,000

$278/sq ft

Nov 19, 2015

Pending

—

Nov 5, 2015

Contingent

—

Sep 30, 2015

Price Changed

$749,000

$289/sq ft

Aug 18, 2015

Price Changed

$795,000

$307/sq ft

Jun 30, 2015

Listed

$825,000

$319/sq ft

Stellar MLS as Distributed by MLS Grid #O5144754

Jul 9, 2013

Sold

$525,000

$203/sq ft

Feb 21, 2013

Listed

$575,000

$222/sq ft

Own a piece of Winter Park history in prime Winter Park location! Original wood floors and French doors throughout add to the character and charm. Brick fireplace in spacious living room. Downstairs bedroom with full bath. 25 x 15 upstairs master with fireplace. Screened sun porch with tongue and groove ceiling and fan. Family has enjoyed living here since 1963 with window units. Single garage/attached 15 x12 space could be finished cottage! Enjoy strolling in lovely neighborhood just a short distance to downtown Winter Park shopping, restaurants & churches!

Year

Property tax

Land + Additions

Assessment*

2025

$11,428 (+3.0%)

2024

$11,094 (+3.6%)

2023

$10,712 (+4.3%)

2022

$10,275 (+1.0%)

2021

$10,168 (+3.9%)

2020

$9,783 (−3.3%)

2019

$10,120 (−0.5%)

$416,000 + $243,399

$659,399

2018

$10,173 (−0.4%)

$416,000 + $243,399

$659,399

2017

$10,214 (−4.5%)

$416,000 + $231,489

$647,489

2016

$10,699 (+63.1%)

$416,000 + $231,489

$647,489

2015

$6,561 (−0.8%)

2014

$6,617 (+81.5%)

2013

$3,646 (+1.2%)

2012

$3,603

Tax history for 1508 Highland Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,428 (+3.0%)

2024

$11,094 (+3.6%)

2023

$10,712 (+4.3%)

2022

$10,275 (+1.0%)

2021

$10,168 (+3.9%)

2020

$9,783 (−3.3%)

2019

$10,120 (−0.5%)

$416,000 + $243,399

$659,399

2018

$10,173 (−0.4%)

$416,000 + $243,399

$659,399

2017

$10,214 (−4.5%)

$416,000 + $231,489

$647,489

2016

$10,699 (+63.1%)

$416,000 + $231,489

$647,489

2015

$6,561 (−0.8%)

2014

$6,617 (+81.5%)

2013

$3,646 (+1.2%)

2012

$3,603

*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

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.33 Acres

Year renovated

1985

Sq. Ft.

2,780

Year built

1923

Style

Single Family Residential

County

Orange County

APN

302207890815051

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
Parking Features: Garage Faces Rear, Garage Faces Side, Oversized, Workshop in Garage
Garage Spaces: 1
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 4

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

Other Rooms Information
Additional Rooms: Bonus Room,Double Master Bedroom,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Foyer,Interior In-Law Suite
# of Rooms: 8

Fireplace Information
Has Fireplace
Fireplace Features: Gas, Living Room, Master Bedroom, Wood Burning

Heating & Cooling
Heating Information: Electric, Wall Units / Window Unit, Zoned
Cooling Information: Zoned

Interior Features
Interior Features: Ceiling Fans(s), Eat-in Kitchen, Master Bedroom Main Floor, Open Floorplan, Other, Split Bedroom
Appliances: Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
Flooring: Brick, Wood

Exterior

Building Information
Construction Materials: Siding, Wood Frame
Roof: Shingle

Exterior Features
Patio And Porch Features: Deck, Patio, Porch, Screened
Exterior Features: French Doors, Irrigation System, Lighting

Property Features
Universal Property Id: US-12095-N-072230890815051-R-N

Waterfront Information
Water Body Name: LAKE VIRGINIA
Water View Y/N: 0
Water Access Y/N: 1
Water Access Description: 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: Guest House, Workshop
Zoning: R-1AA

Land Information
Vegetation: Mature Landscaping, Trees/Landscaped
Future Land Use: 0100
Total Acreage: 1/4 to less than 1/2

Lot Information
Lot Features: Corner Lot, City Limits
Lot Size Acres: 0.33
Lot Size Dimensions: 100x145
Zoning Compatible YN: 1
Other Exemptions YN: 0

Building Information
MFR_BuildingAreaTotalSrchSqM: 318.75

Financial

Tax Information
Tax Annual Amount: $6,617
Tax Year: 2014
Millage Rate: 17.66

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: Cable Connected, Public, Street Lights

Location

HOA Information
Association Fee Requirement: None

School Information
Elementary School: Baldwin Park Elementary
Middle Or Junior High School: Glenridge Middle
High School: Winter Park High

Location Information
Directions: Park Ave to right on Holt at Rollins College. Left on French Avenue to right on Lakeview. Left on Stirling to corner of Virginia and Highland.

Community Information
Pets Allowed: Yes

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 2,780
Stories: 2.0
Lot Size: 0.33 acres
Style: Single Family Residential
Year Built: 1923
Year Renovated: 1985
County: Orange County
APN: 302207890815051

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Attribution Contact: 407-647-1211
Previous Status: Pending
Backups Requested YN: 1
Home Warranty YN: No

Listing Date Information
Days to Contract: 125
Status Contractual Search Date: 2016-01-25

Listing Price Information
Calculated List Price By Calculated Sq Ft: 289.41

Green Information
Direction Faces: West

Home Information
Living Area: 2588
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 240.43
Building Area Total: 3431
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Crawlspace
Levels: Two

Around this home

Schools

AUDUBON PARK SCHOOL

Public PreK-8 • Assigned • 1.3mi

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

8/10 Heat Factor

7 days above 107° expected this year, 21 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

$1.30M – $1.57M

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Home values near 1508 Highland Rd

Data from public records.

Address	Redfin Estimate
1520 Highland Rd, Winter Park, FL 5 Beds \| 6 Baths \| 4720 Sq. Ft.	$2,781,980
1541 Highland Rd, Winter Park, FL 3 Beds \| 2 Baths \| 2330 Sq. Ft.	$1,326,195

Address	Redfin Estimate
1551 Highland Rd, Winter Park, FL 3 Beds \| 2 Baths \| 1689 Sq. Ft.	$1,000,739
1501 Highland Rd, Winter Park, FL 3 Beds \| 3 Baths \| 2203 Sq. Ft.	$1,058,788

Address	Redfin Estimate
1583 Highland Rd, Winter Park, FL 3 Beds \| 3 Baths \| 2502 Sq. Ft.	$1,180,868
1521 Highland Rd, Winter Park, FL 4 Beds \| 3 Baths \| 3418 Sq. Ft.	$1,356,102

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2015. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 32789, FL

Sale history for 1508 Highland Rd

Tax history for 1508 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 1508 Highland Rd

More real estate resources