Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$589,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,637 Sq. Ft.
  • Updated 1 hour ago
See This Home
Save This Home
See This Home
Save This Home
Welcome to 2803 Riddle Drive, where thoughtful updates, timeless charm, and an exceptional Winter Park location come together to create the perfect place to call home. Situated on an oversized lot, this beautifully maintained three-bedroom, two-and-a-half-bath residence offers a spacious floor plan, a two-car garage, and a sparkling private pool designed for year-round Florida living. Step inside to discover a bright, inviting interior featuring fresh paint throughout, brand-new carpeting, and all-new designer light fixtures. The functional layout provides comfortable living spaces for everyday living while offering the ideal setting for entertaining family and friends. Large windows fill the home with natural light, creating a warm and welcoming atmosphere. Step outside to your own private backyard retreat. The oversized, fully fenced yard offers endless possibilities for relaxing, entertaining, gardening, or enjoying sunny Florida afternoons by the pool. A storage shed provides additional space for lawn equipment, tools, or seasonal items, making the backyard as functional as it is enjoyable. Thoughtfully maintained over the years, the home also features a newer roof, newer HVAC system, fresh interior paint, new carpeting, and updated light fixtures, giving the next owner added peace of mind and the opportunity to move right in. Conveniently located just minutes from beautiful Lake Killarney, the shops and restaurants of Park Avenue, and premier shopping and dining throughout Winter Park, this home also offers quick access to i4 and 408, making commuting throughout Central Florida simple and convenient. For investors or buyers seeking future rental potential, the property has been consistently leased since 2017, generating $2,800 per month in rental income, demonstrating its strong desirability and investment appeal. Offering the perfect blend of modern updates, outdoor living, and an unbeatable location, 2803 Riddle Drive is truly move-in ready and waiting for its next owner to call it home.

Full Property Details for 2803 Riddle Dr

General

  • Price: $589,000
  • Taxes: $6,477 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6423829
  • Updated: Today (7/10/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 7
  • Interior Features: Cathedral Ceiling(s), Crown Molding, 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
  • 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
  • Stories/Levels: One
  • Square Feet: 1,637
  • Sq. Ft. Source: Public Records
  • Year Built: 1955

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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

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
7/10/2026
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.

Estimate the Cost for 2803 Riddle Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Corcoran Premier Realty

Similar Properties near 2803 Riddle Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2758 Banchory Rd, Winter Park, FL 32792 - Photo 1
$598,000

2758 Banchory Rd  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 10 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,539
    Sq. Ft.
Listed by Mr Vargas Property Management Llc
140 Wigwam Pl, Maitland, FL 32751 - Photo 1
$609,900

140 Wigwam Pl  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 7 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,236
    Sq. Ft.
Listed by Lpt Realty, Llc
1317 E Harding St, Orlando, FL 32806 - Photo 1
$585,000

1317 E Harding St  Orlando, FL 32806

  • Single Family
  • Active
  • Updated 10 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,671
    Sq. Ft.
Listed by Orlando Brothers Real Estate Llc
1315 E Harding St, Orlando, FL 32806 - Photo 1 Price Reduced
-$5,000 (-0.85%)
$580,000

1315 E Harding St  Orlando, FL 32806

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,789
    Sq. Ft.
Listed by Orlando Brothers Real Estate Llc

Just Listed near 2803 Riddle Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1140 S Orlando Ave, Maitland, FL 32751 - Photo 1 Just Listed
$420,000

1140 S Orlando Ave  #K15  Maitland, FL 32751

  • Condo
  • Active
  • Updated 7 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 816
    Sq. Ft.
Listed by Fannie Hillman & Associates
1460 Lake Shadow Cir, Maitland, FL 32751 - Photo 1 Just Listed
$245,000

1460 Lake Shadow Cir  #7207  Maitland, FL 32751

  • Condo
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,372
    Sq. Ft.
Listed by Infinity Real Estate Group
623 Woodley Rd, Maitland, FL 32751 - Photo 1 Just Listed
$600,000
Open House

623 Woodley Rd  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 20 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,770
    Sq. Ft.
Listed by Keller Williams Winter Park
2462 Carolton Rd, Maitland, FL 32751 - Photo 1 Just Listed
$769,000
Open House

2462 Carolton Rd  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 1 day ago
  • 6
    Beds
  • 3
    Total Baths
  • 2,654
    Sq. Ft.
Listed by Mainframe Real Estate

Price Reduced near 2803 Riddle Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2130 Deloraine Trail, Maitland, FL 32751 - Photo 1 Price Reduced
-$20,000 (-2.5%)
$779,000

2130 Deloraine Trail  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 19 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,175
    Sq. Ft.
Listed by Compass Florida Llc
1404 Caring Ct, Maitland, FL 32751 - Photo 1 Price Reduced
-$20,500 (-3.11%)
$639,000

1404 Caring Ct  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,110
    Sq. Ft.
Listed by Rock Springs Realty, Llc
755 Woodside Rd, Maitland, FL 32751 - Photo 1 Price Reduced
-$50,000 (-5.13%)
$925,000
Open House

755 Woodside Rd  Maitland, FL 32751

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,049
    Sq. Ft.
Listed by Empire Network Realty
1010 Winderley Pl, Maitland, FL 32751 - Photo 1 Price Reduced
-$2,600 (-0.78%)
$329,900

1010 Winderley Pl  #127  Maitland, FL 32751

  • Townhouse
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,563
    Sq. Ft.
Listed by Don Harkins Realty Llc

Recent Sales near 2803 Riddle Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

681 Overspin Dr, Winter Park, FL 32789 - Photo 1 Sold
$669,000

681 Overspin Dr  Winter Park, FL 32789

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,220
    Sq. Ft.
Listed by Re/Max Select Group
Sold by Dj & Lindsey Real Estate
352 Cambridge Blvd, Winter Park, FL 32789 - Photo 1 Sold
$640,000

352 Cambridge Blvd  Winter Park, FL 32789

  • Single Family
  • Closed
  • 5
    Beds
  • 3
    Total Baths
  • 1,917
    Sq. Ft.
Listed by Karen Jacobs
Sold by Charles Rutenberg Realty Orlando
218 Orange Terrace Dr, Winter Park, FL 32789 - Photo 1 Sold
$560,000

218 Orange Terrace Dr  Winter Park, FL 32789

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,618
    Sq. Ft.
Listed by Anne Rogers Realty Group Inc
Sold by Compass Florida Llc
1951 Staunton Ave, Winter Park, FL 32789 - Photo 1 Sold
$599,900

1951 Staunton Ave  Winter Park, FL 32789

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,556
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Re/Max Downtown

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 $589,000 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.

Tour this property