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.
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.
Property Details
Price:
$549,900
MLS #:
O6423829
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
FAIRSHORES PLACE
Neighborhood:
32789winterpark
Listed Date:
Jul 10, 2026
Finished Sq Ft:
1,709
Total Sq Ft:
2,109
Lot Size:
11,050 sqft / 0.25 acres (approx)
Year Built:
1955
See this Listing
Schools
Elementary School:
Killarney Elem
Middle School:
College Park Middle
High School:
Edgewater High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Travertine
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
Laundry Features
In Garage
Levels
One
Exterior
Architectural Style
Florida
Attached Garage YN
1
Community Features
None
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Irrigation System, Sliding Doors
Fencing
Fenced
Garage Spaces
2
Lot Features
In County, Landscaped, Oversized Lot, Sidewalk
Other Structures
Shed(s), Storage
Parking Features
Garage Door Opener, Guest
Patio And Porch Features
Deck, Patio, Porch
Roof
Shingle
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$6,477
Map
Community
- Address2803 RIDDLE DRIVE WINTER PARK FL
- SubdivisionFAIRSHORES PLACE
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Aug 29, 2026
302
Single Family Listed
85
Avg DOM
468
Avg $ / SqFt
$1,281,345
Avg List Price
Property Summary
- Located in the FAIRSHORES PLACE subdivision, 2803 RIDDLE DRIVE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $549,900 and features 3 beds, 3 baths, and has approximately 1,709 square feet of living space, and was originally constructed in 1955. The current price per square foot is $322. The average price per square foot for Single Family listings in WINTER PARK is $468. The average listing price for Single Family in WINTER PARK is $1,281,345. To schedule a showing of MLS#o6423829 at 2803 RIDDLE DRIVE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of CORCORAN PREMIER REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2803 RIDDLE DRIVE
WINTER PARK, FL
