2803 Riddle Dr
Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,637 sqft (on 0.25 acres)
3 Beds
2.5 Baths
1,637 sqft
(on 0.25 acres)
We estimate this home will sell faster than 87% nearby.
Local Information
-- mins to
Description
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.
We estimate this home will sell faster than 87% nearby.
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
$360
Listed
2 days ago
Home Details for 2803 Riddle Dr
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Interior Details Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Dining Room, Great Room, Kitchen |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 1637 Square Feet |
Appliances & Utilities Utilities: Cable Available, Electricity Connected, Sprinkler MeterAppliances: Dishwasher, Disposal, Electric Water HeaterDishwasherDisposalLaundry: In Garage |
Heating & Cooling Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Living Room, Wood BurningHas a Fireplace |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Door: Sliding DoorsFlooring: Carpet, Travertine |
Levels, Entrance, & Accessibility Stories: 1Levels: OneFloors: Carpet, Travertine |
View No View |
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Exterior Home Features Roof: ShinglePatio / Porch: Deck, Patio, PorchFencing: FencedVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation SystemFoundation: Crawlspace, SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener,Guest |
Pool Pool: Gunite, In GroundPool |
Frontage Road Surface Type: Paved, AsphaltNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
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Cumulative Days on Market: 2Days on Market: 2 |
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Year Built Year Built: 1955 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida |
Building Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty |
Property Information Parcel Number: 022229260000040 |
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Price List Price: $589,000Price Per Sqft: $360 |
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MLS Status: Active |
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Direction & Address City: WINTER PARKCommunity: FAIRSHORES PLACE |
School Information Elementary School: Killarney ElemJr High / Middle School: College Park MiddleHigh School: Edgewater High |
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Listing Agent Listing ID: O6423829 |
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Building Area Building Area: 2109 Square Feet |
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Community Features: NoneNot Senior Community |
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Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.25 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional, FHA |
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Business Information Ownership: Fee Simple |
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Mls Number: O6423829Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-022229260000040-R-N |
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None |
Last check for updates: about 8 hours ago
Listing Provided by: Allie George, (407) 457-4815
CORCORAN PREMIER REALTY, (407) 965-1155
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6423829

Also Listed on Stellar MLS.
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
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Market trends in Winter Park
Last updated June 2026
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
Price History for 2803 Riddle Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 07/10/2026 | $589,000 | Listed For Sale | Stellar MLS #O6423829 |
| 05/12/2025 | $2,800 | ListingRemoved | Zillow Rentals |
| 05/09/2025 | $2,800 | Listed For Rent | Zillow Rentals |
| 01/09/2021 | ListingRemoved | N/A | |
| 05/03/2019 | $2,250 | ListingRemoved | N/A |
| 03/31/2019 | $2,250 | Listed For Rent | N/A |
| 10/31/2014 | $229,900 | Sold | N/A |
| 02/27/2014 | $249,000 | ListingRemoved | Agent Provided |
| 02/08/2014 | $249,000 | Listed For Sale | Agent Provided |
| 09/06/2012 | $73,200 | Sold | N/A |
| 01/26/2007 | $265,000 | Sold | N/A |
| 09/29/2005 | $229,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $5,973 |
| Assessment | $365,566 |
Home facts updated by county records
Comparable Sales for 2803 Riddle Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $429,999 | 10/21/25 | 3 | 2 | 1,573 | |
0.23 | Single-Family Home | $360,200 | 01/15/26 | 3 | 2 | 1,401 | |
0.26 | Single-Family Home | $265,400 | 04/24/26 | 3 | 2 | 1,050 | |
0.17 | Single-Family Home | $341,000 | 08/08/25 | 4 | 2 | 1,568 | |
0.20 | Single-Family Home | $450,000 | 09/29/25 | 3 | 2 | 1,372 | |
0.19 | Single-Family Home | $385,000 | 08/18/25 | 2 | 2 | 1,544 | |
0.24 | Single-Family Home | $415,000 | 05/01/26 | 3 | 2 | 1,354 | |
0.37 | Single-Family Home | $470,000 | 12/23/25 | 3 | 2 | 1,785 | |
0.49 | Single-Family Home | $330,000 | 07/10/26 | 3 | 2 | 1,500 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 2803 Riddle Dr.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Allie George, CORCORAN PREMIER REALTY, (407) 965-1155
Agent Phone: (407) 457-4815

2803 Riddle Dr, Winter Park, FL 32789 is a 3 bedroom, 3 bathroom, 1,637 sqft single-family home built in 1955. This property is currently available for sale and was listed by Stellar MLS on Jul 10, 2026. The MLS # for this home is MLS# O6423829.

