224 Overlook Rd, Winter Park, FL 32789
SOLD
DEC 5, 2025

224 Overlook Rd
Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,399 sqft

$645,000

Last Sold: Dec 5, 2025
3% below list $665K
$461/sqft
Est. Refi. Payment $4,495/mo*
Refinance Your Home

$645,000

Last Sold: Dec 5, 2025
3% below list $665K
$461/sqft
Est. Refi. Payment $4,495/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,399 sqft

Local Information

  • Map ViewExplore the area around 224 Overlook Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1936
Living Area
1,399 sqft
Price/Sqft
$461/sqft
Parking
Open Parking
HOA
None

About this House

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.
224 Overlook Rd, Winter Park, FL 32789 is a 2 bedroom, 2 bathroom, 1,399 sqft single-family home built in 1936. It last sold for $645,000 on Dec 5, 2025 (3% below the $665,000 asking price). It is currently off market. The Trulia Estimate is $678,700, with a rent estimate of $3,636/month.

Home Details for 224 Overlook Rd

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bathroom 1, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1399 Square Feet
Appliances & Utilities
Utilities: Public, Street LightsAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: In GarageRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: RodsFlooring: Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Tile, Hardwood
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShingleVegetation: Bamboo, Fruit Trees, Oak TreesOther Structures: Shed(s)Exterior: StorageFoundation: CrawlspaceNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway
Frontage
Road Surface Type: Brick, PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 3

Property Information

Year Built
Year Built: 1936
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Wood SidingNot a New ConstructionNot Attached PropertyNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 052230850608020

Price & Status

Price
List Price: $665,000Price Per Sqft: $461/sqft
Status Change & Dates
Off Market Date: Fri Oct 24 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: SYLVAN LAKE SHORES

Building

Building Area
Building Area: 1563 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Suncoast TampaNo HOA

Lot Information

Lot Area: 6156 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: TB8439469Showing Requirements: Appointment Only, Combination Lock BoxUniversal Property Id: US-12095-N-052230850608020-R-N
Last check for updates: about 7 hours ago
Listed by Stephen Hachey, (813) 642-6030
FLAT FEE MLS REALTY, (813) 642-6030
Bought with: Claudio Maciel, (407) 561-0108, NOVA REAL ESTATE SERVICES INC, (407) 592-1744
Originating MLS: Suncoast Tampa
Source: Stellar MLS, MLS#TB8439469
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price History for 224 Overlook Rd

DatePriceEventSource
12/05/2025$645,000Sold
Stellar MLS #TB8439469
10/24/2025$665,000PendingStellar MLS #TB8439469
10/21/2025$665,000Listed For SaleStellar MLS #TB8439469
01/26/2023$494,000Sold
N/A
12/13/2022$499,000PendingStellar MLS #O6062582
10/18/2022$499,000Listed For SaleStellar MLS #O6062582
02/02/2022$450,000Sold
N/A
12/14/2021$499,000PendingStellar MLS #O5985358
11/24/2021$499,000PendingToActiveStellar MLS #O5985358
11/19/2021$499,000PendingStellar MLS #O5985358
11/12/2021$525,000Listed For SaleStellar MLS #O5985358
10/16/2009$319,000ListingRemovedAgent Provided
08/13/2009$319,000PriceChange
Agent Provided
06/06/2009$365,000PriceChange
Agent Provided
04/17/2009$399,000PriceChange
Agent Provided
02/20/2009$420,000Listed For SaleAgent Provided
01/27/2004$215,000Sold
N/A
03/21/2003$190,000Sold
N/A
02/18/1997$125,000Sold
N/A

Market trends in Winter Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$452K
$7.33KMoM
Sale-to-List Price
97.7%
0.2%MoM
Price per sq ft
$288
$1MoM
Available listings
380
7MoM
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Property Tax and Assessment

Year2024
Tax$5,624
Assessment$413,036
Home facts updated by county records

Comparable Sales for 224 Overlook Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
311 Cortland Ave, Winter Park, FL
0.22
Single-Family Home
$750,000
09/25/25
2
2
1,382
1760 Greenwich Ave, Winter Park, FL
0.39
Single-Family Home
$595,000
06/19/26
3
2
1,610
250 Cortland Ave, Winter Park, FL
0.16
Single-Family Home
$920,000
07/22/26
3
2
2,114
1780 Goodrich Ave, Winter Park, FL
0.41
Single-Family Home
$615,000
06/24/26
3
2
1,283
801 Audubon Ln, Winter Park, FL
0.28
Single-Family Home
$850,000
01/08/26
2
2
1,320
1701 Goodrich Ave, Winter Park, FL
0.36
Single-Family Home
$680,000
07/17/26
3
2
1,528
171 Cortland Ave, Winter Park, FL
0.12
Single-Family Home
$1,245,000
09/03/25
2
2
1,683
1740 Anzle Ave, Winter Park, FL
0.38
Single-Family Home
$475,000
02/02/26
4
2
1,808
1871 Bryan Ave, Winter Park, FL
0.60
Single-Family Home
$499,000
06/24/26
3
2
1,232

Nearby homes

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Assigned Schools

These are the assigned schools for 224 Overlook Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 595 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 79 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
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  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
    Flag
  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
    Flag
  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
    Flag
  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
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  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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Explore by feature - Pet Friendly

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Homes for sale near 224 Overlook Rd

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Off Market Homes Near 224 Overlook Rd

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