Under contract-accepting backup offers. Life in Winter Park is about more than just where you liveit'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 updatesincluding a new roof (2022), HVAC system (2022), fresh interior paint, and updated lightingprovide 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.
Charming Winter Park Pool Home! This fantastic three bedroom, two and one-half bath home has been completely renovated inside and out with high-end finishes. New Tile floors throughout with beautiful inlay in the foyer, granite counters and cabinets in the kitchen and bathrooms, stainless steel appliances, freshly painted inside and out, all new windows throughout home with blinds. Hot water heater, plumbing, roof and HVAC all replaced in 2013. Great open floor plan with rooms that flow seamlessly. Family Room offers a wood burning fireplace, bar and sliding doors that lead to the patio and new marcited pool. Nice fenced yard, oversized lot and two car garage. All this with a Winter Park address! Do not miss this one!
Stellar MLS as Distributed by MLS Grid #O5324776
Oct 30, 2014
Sold
$229,900
$135/sq ft
Oct 13, 2014
Pending
—
Oct 13, 2014
Listed
$229,900
$135/sq ft
Charming Winter Park pool home! This fantastic three bedroom, two and one-half bath home has been completely renovated inside and out with high-end finishes. New tile floors throughout with beautiful inlay in the foyer, granite counters and cabinets in the kitchen and bathrooms, stainless steel appliances, freshly painted inside and out, all new windows throughout home with blinds. Hot water heater, plumbing, roof, and HVAC were all replaced in 2013. Great open floor plan with rooms that flow seamlessly. The family room offers a wood burning fireplace, bar, and sliding doors that lead to the patio and new marcited pool. Nice fenced yard, oversized lot, and two car garage. All this with a Winter Park address! Do not miss this one!
Stellar MLS as Distributed by MLS Grid #O5109673
Sep 12, 2012
Sold
$73,200
$43/sq ft
Jul 6, 2012
Listed
$67,320
$39/sq ft
Public Records
Jan 26, 2007
Sold
$265,000
$155/sq ft
Public Records
Sep 29, 2005
Sold
$229,000
$134/sq ft
Public Records
Apr 1, 1992
Sold
$79,500
$47/sq ft
Public Records
Jun 1, 1977
Sold
$33,000
$19/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$6,477 (+8.4%)
$105,000 + $272,800
$377,800
2024
$5,973 (+8.0%)
$105,000 + $272,800
$377,800
2023
$5,529 (+12.8%)
$105,000 + $260,566
$365,566
2022
$4,901 (+13.2%)
$115,000 + $205,448
$320,448
2021
$4,330 (+77.5%)
$115,000 + $205,448
$320,448
2020
$2,439 (−2.1%)
$75,900 + $182,130
$258,030
2019
$2,493 (+1.0%)
2018
$2,469 (+1.7%)
2017
$2,427 (+1.2%)
2016
$2,399 (−15.1%)
2015
$2,827 (+57.5%)
$42,000 + $147,387
$189,387
2014
$1,795 (+5.9%)
2013
$1,694 (−17.3%)
2012
$2,050
Public record
Public record
Zoning
Beds
3
Baths
3
Stories
1
Lot width
—
Lot depth
—
Lot size
0.25 Acres
Year renovated
1990
Finished Sq. Ft.
1,637
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,637
Year built
1955
Style
Single Family Residential
County
Orange County
APN
292202260000040
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1A
Single-Family Dwelling Districts
The areas included within R-1-A single-family dwelling districts are intended to be single-family residential areas with large lots and low population densities. Certain structures and uses required to serve educational, religious, utilities and noncommercial recreational needs of such areas are permitted within the districts as special exceptions.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Fire house
Police station
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
7 days above 107° expected this year, 22 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winter Park, FL • 32789
Average low and high temperatures (°F)
68
48
75
55
81
61
84
65
90
73
92
75
94
77
91
76
88
74
83
69
78
60
73
56
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
97/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 17% for direct sun exposure in Winter Park. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10 hrs
7.4 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 2803 Riddle Dr
$516,732
$8,268 under list price of $525K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $420K to $640K.