Off Market Jul 2018 for $700K

$1,318,732

Est. refi paymentEst. refi $3,973/mo

•

3,499

sq ft

211 Overlook Rd, Winter Park, FL 32789

About this home

Wonderful two story character home in the heart of Winter Park on a quiet tree lined brick street. This adorable home has such great curb appeal and is in a wonderful part of Olde Winter Park-this cutie pie is pure potential! The interior offers five bedrooms, three and one-half baths, a formal living room, separate den and/or office, and family room. Master suite (downstairs) is overly spacious and features a wood burning fireplace and en suite, complete with a large soaking tub, shower, and expansive walk-in closet. Downstairs guest suite has private bath and could easily be enclosed to serve as a guest wing. Kitchen has been updated with stainless steel appliances, built-in oven, and pantry closet. Outdoor living space is extraordinary! Located on 0.34 acres the backyard is fantastic and has both an open deck and a covered patio that overlook the mature lawn and gardens. Hardwood floors, butler’s pantry, bay windows, high ceilings, and more. Charming and delightful this house will make you feel right at home. This home is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School.

Single-familyProperty Type

1936Year Built

0.34 acresLot Size

$377Est. Price/Sq.Ft.

2 car garageParking

Listed by Kelly Price • KELLY PRICE & COMPANY LLC

Bought with Jennifer Sloan • KELLY PRICE & COMPANY LLC

Redfin checked: 2 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #O5570876

Redfin Estimate

$1,318,732

$619K since sold in July 2018$12K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 36.7% lower than the average sale price ($2.08M) of 6 comparable homes.

SOLD JUL 24, 2026
$1,300,000
A
3 beds2.5 baths2,821 sq ft
321 Sylvan Blvd, Winter Park, FL 32789
SOLD JUL 31, 2026
$2,650,000
B
5 beds4 baths4,917 sq ft
1630 Lasbury Ave, Winter Park, FL 32789
SOLD JUN 25, 2026
$1,400,000
C
4 beds5.5 baths3,609 sq ft
234 Detmar Dr, Winter Park, FL 32789
SOLD MAY 15, 2026
$1,300,000
D
3 beds3.5 baths3,215 sq ft
1661 Woodland Ave, Winter Park, FL 32789
SOLD JUN 1, 2026
$4,250,000
E
4 beds4 baths3,181 sq ft
1336 College Pt, Winter Park, FL 32789
SOLD APR 22, 2026
$1,600,000
F
4 beds2.5 baths3,263 sq ft
446 Alberta Dr, Winter Park, FL 32789

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Sell

$774,952

Est. take-home

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Est. cash available

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Rent

$4,720/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

96.1%

0.2% MoM

Median sale price

$1.2M

$337K MoM

Avg. days on market

36d

0 days MoM

Recently sold homes

144

14 MoM

New listings for sale

NEW 5 HRS AGO
$130,000
1 bed1 bath645 sq ft
2500 Lee Rd #143, Winter Park, FL 32789
COMING SOON
$6,995,000
5 beds5.5 baths5,479 sq ft
901 Golfview Ter, Winter Park, FL 32789
COMING SOON
$1,649,000
3 beds3 baths2,857 sq ft
1200 Woodmere Dr, Winter Park, FL 32789
NEW 7 HRS AGO
$1,350,000
4 beds4 baths2,998 sq ft
1320 Orchid Ave, Winter Park, FL 32789
OPEN SAT, 1PM TO 4PM
$1,350,000
3 beds4 baths2,191 sq ft
720 Pansy Ave, Winter Park, FL 32789
FOR SALE BY OWNER
$155,000
3 beds2 baths1,149 sq ft
1695 Lee Rd, Winter Park, FL 32789
OPEN SAT, 12PM TO 2PM
$725,000
3 beds2 baths1,563 sq ft
1850 Bryan Ave, Winter Park, FL 32789
COMING SOON
$700,000
4 beds3 baths2,016 sq ft
1592 Arbor Park Dr, Winter Park, FL 32789
OPEN SAT, 11AM TO 2PM
$1,100,000
3 beds2.5 baths2,196 sq ft
2227 Howard Dr, Winter Park, FL 32789
COMING SOON
$1,050,000
3 beds2 baths1,469 sq ft
393 Holt Ave, Winter Park, FL 32789
See all

Provided by Redfin

Sale history for 211 Overlook Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5570876

Jul 11, 2018

Sold

$700,000

$200/sq ft

May 31, 2018

Pending

—

May 21, 2018

Relisted

—

May 14, 2018

Pending

—

Mar 26, 2018

Listed

$749,900

$214/sq ft

Stellar MLS as Distributed by MLS Grid #O5479705

Jun 1, 2017

Listing Removed

—

Jun 1, 2017

Sold

$3,950

$1/sq ft

May 18, 2017

Pending

—

May 8, 2017

Price Changed

$775,000

$221/sq ft

Apr 24, 2017

Relisted

—

Apr 21, 2017

Pending

—

Mar 10, 2017

Price Changed

$790,000

$226/sq ft

Feb 2, 2017

Price Changed

$825,000

$236/sq ft

Dec 6, 2016

Price Changed

$875,000

$250/sq ft

Dec 5, 2016

Listed

$985,000

$282/sq ft

Gorgeous 1930’s character home in the heart of Winter Park. White panel siding, green Board and Batten shutters, and a gated driveway all lend to this home’s amazing curb appeal. Stunning interior offers five bedrooms, three and one-half baths, a formal living room, separate den and/or office, and family room. Master suite is overly spacious and features a wood burning fireplace and en suite, complete with a large soaking tub, shower, and expansive walk-in closet. Downstairs guest suite has private bath and could easily be enclosed to serve as a guest wing. Kitchen has been updated with stainless steel appliances, built-in oven, and pantry closet. Outdoor living space is extraordinary! Located on 0.34 acres the backyard is fantastic and has both an open deck and a covered patio that overlook the beautifully cared for lawn and gardens. Hardwood floors, butler’s pantry, bay windows, high ceilings, and more. Charming and delightful this house will make you feel right at home.

Stellar MLS as Distributed by MLS Grid #O5366483

Nov 24, 2015

Listing Removed

—

Nov 24, 2015

Sold

$3,500

$1/sq ft

Nov 18, 2015

Pending

—

Sep 21, 2015

Price Changed

$875,000

$250/sq ft

Sep 4, 2015

Relisted

—

Aug 28, 2015

Listing Removed

—

Jul 2, 2015

Price Changed

$935,000

$267/sq ft

Jul 1, 2015

Relisted

—

Jul 1, 2015

Listing Removed

—

May 13, 2015

Listed

$985,000

$282/sq ft

Just Reduced!!! Gorgeous 1930’s two story character home in the heart of Winter Park on a quiet tree lined brick street. White panel siding, green Board and Batten shutters, and a gated driveway all lend to this home’s amazing curb appeal. Stunning interior offers five bedrooms, three and one-half baths, a formal living room, separate den and/or office, and family room. Master suite is overly spacious and features a wood burning fireplace and en suite, complete with a large soaking tub, shower, and expansive walk-in closet. Downstairs guest suite has private bath and could easily be enclosed to serve as a guest wing. Kitchen has been updated with stainless steel appliances, built-in oven, and pantry closet. Outdoor living space is extraordinary! Located on 0.34 acres the backyard is fantastic and has both an open deck and a covered patio that overlook the beautifully cared for lawn and gardens. Hardwood floors, butler’s pantry, bay windows, high ceilings, and more. Charming and delightful this house will make you feel right at home.

Public Records

Aug 27, 2003

Sold

$735,000

$210/sq ft

Public Records

Jun 1, 1989

Sold

$210,000

$60/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$11,460 (+3.5%)

2024

$11,077 (+4.0%)

2023

$10,648 (+8.0%)

2022

$9,855 (+1.1%)

2021

$9,752 (+11.4%)

2020

$8,752 (−6.4%)

2019

$9,351 (−21.0%)

$372,000 + $240,257

$612,257

2018

$11,843 (−0.2%)

$372,000 + $240,257

$612,257

2017

$11,863 (+1.3%)

$372,000 + $334,840

$706,840

2016

$11,713 (+49.5%)

$372,000 + $334,840

$706,840

2015

$7,836 (−0.9%)

2014

$7,904 (+2.2%)

2013

$7,736 (−1.7%)

2012

$7,866

Tax history for 211 Overlook Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,460 (+3.5%)

2024

$11,077 (+4.0%)

2023

$10,648 (+8.0%)

2022

$9,855 (+1.1%)

2021

$9,752 (+11.4%)

2020

$8,752 (−6.4%)

2019

$9,351 (−21.0%)

$372,000 + $240,257

$612,257

2018

$11,843 (−0.2%)

$372,000 + $240,257

$612,257

2017

$11,863 (+1.3%)

$372,000 + $334,840

$706,840

2016

$11,713 (+49.5%)

$372,000 + $334,840

$706,840

2015

$7,836 (−0.9%)

2014

$7,904 (+2.2%)

2013

$7,736 (−1.7%)

2012

$7,866

*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

0.34 Acres

Year renovated

1970

Sq. Ft.

3,499

Year built

1936

Style

Single Family Residential

County

Orange County

APN

302205850602180

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

R-1A \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-1A 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 Spaces: 2
Has Garage

Interior

Bedroom Information
# of Bedrooms: 5

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

Other Rooms Information
Additional Rooms: Den/Library/Office,Family Room,Formal Dining Room Separate,Inside Utility
# of Rooms: 11

Fireplace Information
Has Fireplace
Fireplace Features: Living Room, Wood Burning

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

Interior Features
Interior Features: Eat-in Kitchen, Split Bedroom, Walk-in Closet(s)
Window Features: Blinds
Appliances: Built-In Oven, Cooktop, Dishwasher, Refrigerator
Flooring: Carpet, Wood

Exterior

Building Information
Construction Materials: Wood Frame
Roof: Shingle

Exterior Features
Patio And Porch Features: Deck, Patio, Porch
Exterior Features: French Doors

Waterfront Information
Waterfront Feet Total: 0
Water View Y/N: 0
Water Access Y/N: 0
Water Extras Y/N: 0

Property Information
CDD Y/N: 0
Homestead Y/N: 0
Property Type: Residential
Property Sub Type: Single Family Residence
Zoning: R-1A

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

Lot Information
Lot Features: City Limits, Street Brick
Lot Size Acres: 0.34
Lot Size Dimensions: 150 x 100
Zoning Compatible YN: 1

Financial

Tax Information
Tax Annual Amount: $11,863
Tax Year: 2017
Millage Rate: 17.62

Lease / Rent Details
Lease Restrictions YN: 0

Utilities

Utility Information
Water Source: Public
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public

Location

Multi-Unit Information
Unit Number YN: 0

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

School Information
Elementary School: Brookshire Elem
Middle Or Junior High School: Glenridge Middle
High School: Winter Park High

Location Information
Directions: E on Fairbanks, right on Sylvan, Sylvan merges to become Overlook, house on right.

Community Information
Pets Allowed: Yes

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,499
Stories: 2.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1936
Year Renovated: 1970
County: Orange County
APN: 302205850602180

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: 65
Status Contractual Search Date: 2018-07-11T00:00:00.000

Listing Price Information
Calculated List Price By Calculated Sq Ft: 214.32

Home Information
Living Area: 3499
Living Area Units: Square Feet
Living Area Source: Public Records
Building Area Total: 4305
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Basement, Crawlspace, Slab
Levels: Two

Around this home

Schools

Brookshire Elementary School

Public PreK-5 • Assigned • 1.2mi

4/10

Glenridge Middle School

Public 6-8 • Assigned • 1.4mi

7/10

Winter Park High School

Public 9-12 • Assigned • 1.2mi

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

$1.25M – $1.52M

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Home values near 211 Overlook Rd

Data from public records.

Address	Redfin Estimate
151 Overlook Road, Winter Park, FL 3 Beds \| 3 Baths \| 2547 Sq. Ft.	$1,062,536
193 Overlook Road, Winter Park, FL 3 Beds \| 1.5 Baths \| 2201 Sq. Ft.	$1,172,860

Address	Redfin Estimate
165 Overlook Road, Winter Park, FL 3 Beds \| 2 Baths \| 1951 Sq. Ft.	$894,917
220 Overlook Road, Winter Park, FL 2 Beds \| 2 Baths \| 1393 Sq. Ft.	$726,445

Address	Redfin Estimate
183 Overlook Road, Winter Park, FL 3 Beds \| 2 Baths \| 2291 Sq. Ft.	$892,353
224 Overlook Road, Winter Park, FL 2 Beds \| 1.5 Baths \| 1399 Sq. Ft.	$721,669

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

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