Discover the timeless allure of this enchanting 2 bedroom, 1.5 bath home, built in 1936 and nestled in the heart of historic Winter Park steps from Lake Mizell. Located on one of the area's iconic brick-paved streets and surrounded by majestic oak trees, this Winter Park bungalow is a rare find. The home's classic design features original hard wood floors, original glass windows, a cozy wood-burning fireplace, and an abundance of natural light blending vintage charm with practical functionality. With its warm character and unbeatable location, this delightful property captures the essence of Winter Park living at its finest.
Single-familyProperty Type
1936Year Built
6,156 sq ftLot Size
$516Est. Price/Sq.Ft.
Listed by Stephen Hachey• FLAT FEE MLS REALTY
Contact: 813-642-6030
Bought with Claudio Maciel• NOVA REAL ESTATE SERVICES INC
Charming bungalow on olde brick street in the heart of Winter Park. Beautiful Sylvan Lake Shores neighborhood, steps from Lake Mizell. Improved- newer water heater, foundation supported and stabilized, all new electrical! Timeless and valuable- real hardwood floors and 1930’s custom wood burning fireplace. Architectural details throughout! Inviting front porch, curved wall detail, telephone niche turned into extra storage and craftsman built window seat with storage. Huge family room large enough for piano or office. Open and very spacious kitchen connected to family and dining room. Dishwasher and oven have been replaced with updated Stainless Steel appliances. Generous living room, dining room and 2 bedrooms oversized with great closet space. The owners have retained many charming original items in the home such as the original glass doors and door knobs and the original exterior doors and windows. French doors lead you out to entertaining deck and backyard perfect for pets! Excellent wood framed shed being utilized for laundry room and storage. Long driveway which can fit several cars. Total gem in a neighborhood full of multi million dollar homes. Adjacent to Windsong and easy walk to Park Avenue (1.0 mile). Home perfectly situated between Lake Mizell, Lake Sylvan and Lake Berry. Brookshire, Glenridge and WPHS. Convenient to private schools. Close to Rollins, and Winter Park Hospital. Own a piece of true Winter Park!
Stellar MLS as Distributed by MLS Grid #O5985358
Jan 27, 2022
Sold
$450,000
$322/sq ft
Dec 14, 2021
Pending
—
Nov 24, 2021
Relisted
—
Nov 22, 2021
Pending
—
Nov 19, 2021
Price Changed
$499,000
$357/sq ft
Nov 12, 2021
Listed
$525,000
$375/sq ft
Delightfully charming, 1936 cottage style home, 2 bedroom, 2 bath located in the beautiful Sylvan Lake Shores district of Winter Park. This home is situated on one of the most picturesque brick streets in town. Majestic oak trees, camellia bushes and blooming bougainvillea surround the home. A quick walk down the street will take you to Lake Mizell. Many of the historical details remain in the home beginning with a welcoming brick front porch overlooking the lawn. The sunny living room features a circa 1930’s wood burning fireplace and the adjacent dining room retains the craftsman built window seat with storage. Warm, well cared for wood floors flow through-out the main part of the home including the bedrooms. A spacious family room with tile floor is situated behind the living room and dining room with plenty of room for all, and is adjacent to the kitchen. Enter the surprisingly large and relaxing master bedroom with its en-suite bath and closet. The second bedroom has a full bath as well, located off the hall. The owners have retained many charming original items in the home such as the original glass doors and door knobs and the original exterior doors and windows. Easy access to the quiet backyard and deck from the French doors in the family room. A large wood framed shed is at the end of a long drive and offers storage as well as a laundry room. Excellent Winter Park Schools. A 10 minute walk to Park Ave for shopping and dining in downtown Winter Park! Come and take a look today!
Stellar MLS as Distributed by MLS Grid #O4897957
Feb 17, 2009
Listed
*
Public Records
Jan 27, 2004
Sold
$215,000
$154/sq ft
Public Records
Mar 21, 2003
Sold
$190,000
$136/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$5,806 (+3.2%)
2024
$5,624 (+24.9%)
2023
$4,503 (−12.6%)
2022
$5,155 (+133.3%)
$250,000 + $83,612
$333,612
2021
$2,210 (+4.3%)
$250,000 + $83,612
$333,612
2020
$2,120 (−3.0%)
2019
$2,184 (+0.9%)
2018
$2,165 (+1.3%)
2017
$2,138 (+2.3%)
2016
$2,090 (−2.3%)
2015
$2,140 (−0.8%)
2014
$2,157 (+2.6%)
2013
$2,103 (+1.4%)
2012
$2,074
Tax history for 224 Overlook Rd
Year
Property tax
Land + Additions
Assessment*
2025
$5,806 (+3.2%)
2024
$5,624 (+24.9%)
2023
$4,503 (−12.6%)
2022
$5,155 (+133.3%)
$250,000 + $83,612
$333,612
2021
$2,210 (+4.3%)
$250,000 + $83,612
$333,612
2020
$2,120 (−3.0%)
2019
$2,184 (+0.9%)
2018
$2,165 (+1.3%)
2017
$2,138 (+2.3%)
2016
$2,090 (−2.3%)
2015
$2,140 (−0.8%)
2014
$2,157 (+2.6%)
2013
$2,103 (+1.4%)
2012
$2,074
*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
2
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
6,156 Sq. Ft.
Year renovated
1970
Sq. Ft.
1,399
Year built
1936
Style
Single Family Residential
County
Orange County
APN
302205850608020
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
Sep 7, 2026 • Active
Demolition permit - single family residence
Complete the demolition, removal, and clean up of a single-family home.
Demolition
Aug 30, 2022 • Final
Residential electric
Perform a complete electrical rewiring of the house and install a new meter enclosure.
Electrical
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Parking Features: Driveway
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 2
Bathroom Information
# of Full Baths (Total): 1
# of Half Baths (Total): 1
Laundry Room Information
Laundry Features: In Garage
Other Rooms Information
Additional Rooms: Family Room
# of Rooms: 8
Fireplace Information
Has Fireplace
Fireplace Features: Living Room, Wood Burning
Heating & Cooling
Heating Information: Central, Electric
Cooling Information: Central Air
Interior Features
Interior Features: Eat-in Kitchen, Thermostat
Window Features: Rods
Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer