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$569,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,709 Sq. Ft.
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Life in Winter Park is about more than just where you live-it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates-including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting-provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

Full Property Details for 2803 Riddle Dr

General

  • Price: $569,000
  • Taxes: $6,477 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6423829
  • Updated: 7/22/2026
  • Added to Site: 46 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 7
  • Interior Features: Cathedral Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room, Wood Burning
  • Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Travertine

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Garage

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground

Exterior

  • Exterior Features: Irrigation System, Sliding Doors
  • Deck/Patio: Deck, Patio, Porch
  • Porch/Patio/Deck: Deck, Patio, Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener, Guest

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: FAIRSHORES PLACE
  • Driving Directions: From Fairbanks take a right onto Wymore then take a left onto Riddle Drive. The home will be on your right.
  • Direction Faces: South

School Information

  • Elementary School: Killarney Elem
  • Middle School: College Park Middle
  • High School: Edgewater High

Community

  • Community Name: 32789 - Winter Park
  • Community Features: None

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Sprinkler Meter

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 1,709
  • Sq. Ft. Source: Estimated
  • Year Built: 1955

Additional Structures

  • Other Structures: Shed(s), Storage

Lot Features

  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 11,050
  • Lot Size: 11050
  • Lot Dimensions: 85 x 130
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Financial Considerations

  • Assoc Fee Desc.: None
  • Tax Amount: $6,477
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: FAIRSHORES PLACE T/87 LOT 4
  • Flood Zone Info: x
  • APN: 22229260000040
  • Property ID: 22229260000040

Listed by Corcoran Premier Realty

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Listing agent

— 2803 Riddle Dr —

  • Corcoran Premier Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2803 Riddle Dr

School District:Orange County School District
NameGradesDistance
Killarney Elementary School
2401 Wellington Boulevard, Winter Park, FL 32789
PK-50.3 mi
College Park Middle School
1201 Maury Road, Orlando, FL 32804
6-81 mi
Edgewater High School
3100 Edgewater Drive, Orlando, FL 32804
9-121.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2803 Riddle Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/20/2026
Price Reduced
$569,000
-3.4%
MLS
7/10/2026
Listed
$589,000
156.2%
MLS
10/30/2014
Sold
$229,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2803 Riddle Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,477
—
$373,110
-1%
2025
$6,477
8%
$377,800
3%
2024
$5,973
8%
$365,566
-3%
2023
$5,529
28%
$376,451
46%
2021
$4,330
-12%
$258,030
-19%
2022
$4,901
13%
$320,448
75%
2021
$4,330
74%
$183,262
3%
2019
$2,493
1%
$178,653
2%
2018
$2,469
2%
$175,322
2%
2017
$2,427
1%
$171,716
2%
2016
$2,399
-15%
$168,184
-11%
2015
$2,828
58%
$189,387
114%
2014
$1,795
6%
$88,403
6%
2013
$1,694
—
$83,164
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Corcoran Premier Realty

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2803 Riddle Drive, Winter Park, FL 32789 (MLS# O6423829) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 2803 Riddle Drive is currently listed for $569,000 and was received on July 10, 2026. Want to learn more about 2803 Riddle Drive? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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