Ask Redfin
NEW 9 HRS AGO
For sale
$299,900
Est. $2,304/mo —
4
bd
•
2.5 ba
•
2,445
sq ft

2821 Riddle Dr, Winter Park, FL 32789

map-entry

About this home

Single-familyProperty Type
1943Year Built
9,750 sq ftLot Size
$123Price/Sq.Ft.
Listed by Linda Mardegan • ORLANDO REGIONAL REALTY
Contact: 407-751-2111
Listing updated:
Redfin checked: a few seconds ago
•Source:Stellar MLS as Distributed by MLS Grid #O6457113
9 hours on Redfin • 11 views • 1 favorites

Payment calculator

$2,304 per month

Principal and interest$1,637
Property taxes
HOA dues
Home insurance
Utilities
Down payment
20% ($59,980)
Home price
$299,900
Loan details
30-yr fixed, 7.25%
5 minutes to get started. No credit impact. 

See this home in person

Open houses
No upcoming open houses.

Around this home

Schools

Killarney Elementary School

Public PreK-5 • Assigned • 0.3mi

7/10
College Park Middle School

Public 6-8 • Assigned • 1.0mi

3/10
Edgewater High School

Public 9-12 • Assigned • 1.1mi

5/10
Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Property details

Kitchen

Bathroom

Bedroom

  • Interior features
  • Built-in features
  • Bedrooms
  • 4 bedrooms
  • Bathrooms
  • 2 full bathrooms
  • 1 half bathroom
  • Kitchen
  • Refrigerator
  • Laundry & utility
  • Inside laundry
  • Flooring
  • Laminate flooring
  • Heating & cooling
  • Central heating
  • Central air conditioning

Sale and tax history for 2821 Riddle Dr

Public record

Beds
4
Baths
3
Stories
1
Lot width
—
Lot depth
—
Lot size
9,750 Sq. Ft.
Year renovated
2000
Finished Sq. Ft.
2,445
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,445
Year built
1943
Style
Single Family Residential
County
Orange County
APN
292211256200060
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Mar 11, 2026.

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°
82°
68°
78°
60°
73°
56°
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Sun exposure

94/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in Winter Park. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.7 hrs
7.6 hrs
JuneDecember
Provided by Shadowmap

Redfin Estimate for 2821 Riddle Dr

$299,792
$108 under list price of $300K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $305K to $1.5M.

More resources

Rental earnings

Est. $3,694 per month, based on comparable rentals

Tour for free, no strings attached

Make a winning offer with the help of a local agent
Ask a question
(407) 594-7296

Early Access listings

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON
$420,000
3 beds2 baths1,844 sq ft
1109 Saldivar Rd, The Villages, FL 32159
EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON
$799,900
5 beds3 baths2,911 sq ft
10622 Cape Hatteras Dr, Tampa, FL 33615
EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON
$724,000
3 beds2 baths1,492 sq ft
2055 Gulf of Mexico Dr Unit G2102, Longboat Key, FL 34228
EARLY ACCESSCOMPASS COMING SOON
$499,900
3 beds3 baths2,230 sq ft
10851 Mangrove Cay Ln NE #1213, St Petersburg, FL 33716
EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON
$725,000
4 beds3 baths3,015 sq ft
12337 Creek Edge Dr, Riverview, FL 33579
EARLY ACCESSREDFIN COMING SOON
$235,000
2 beds1.5 baths1,144 sq ft
1229 Winter Green Way, Winter Garden, FL 34787

Nearby similar homes

$450,000
3 beds1 bath1,229 sq ft
2942 Helen Ave, Orlando, FL 32804
Corner lot • Neighborhood parks • Convenient access
3D WALKTHROUGH
$1,575,000
3 beds2.5 baths2,733 sq ft
2207 Kindel Ave, Winter Park, FL 32789
Lakefront luxury • Waterfront setting • Gourmet kitchen
3D & VIDEO TOUR
$682,000
3 beds2 baths1,671 sq ft
3400 Neptune Dr, Orlando, FL 32804
Updated home • Huge pool • Fully-fenced yard
$449,900
3 beds2 baths1,614 sq ft
1660 Orange Ave, Winter Park, FL 32789
Remodeled bathrooms • Open kitchen • New outdoor deck
$419,900
3 beds1 bath1,304 sq ft
712 Baffie Ave, Winter Park, FL 32789
Updated bungalow • Wood floors • Crown molding
3D WALKTHROUGH
$659,000
3 beds3 baths1,794 sq ft
900 Carver St, Winter Park, FL 32789
Remodeled kitchen • Shaker cabinetry • Remodeled bathrooms

New listings for sale in 32789

NEW 9 HRS AGO
$299,900
4 beds2.5 baths2,445 sq ft
2821 Riddle Dr, Winter Park, FL 32789
9,750 sq ft lot • Built 1943
$1,699,999
4 beds3.5 baths2,923 sq ft
647 Randy Ln, Winter Park, FL 32789
Corner lot • Chef's kitchen • Expansive patio
NEW 19 HRS AGO
$4,695,000
11 beds7.5 baths4,603 sq ft
617 N Interlachen Ave, Winter Park, FL 32789
Renovated in 1981 • 0.5 acre lot • Built 1929
NEW 22 HRS AGO
$415,000
3 beds2 baths1,440 sq ft
2821 Chantilly Ave, Winter Park, FL 32789
0.76 acre lot • Waterfront setting • 250 feet of frontage
$2,100,000
4 beds4.5 baths2,830 sq ft
Winter Park, FL 32789
Heated wading pool • Outdoor kitchen • Gas grill
$629,500
2 beds2 baths858 sq ft
640 N Park Ave #26, Winter Park, FL 32790
Renovated • New ac • Auto window shades
OPEN SUN, 12PM TO 2PM
$1,100,000
3 beds3 baths2,626 sq ft
531 Worthington Dr, Winter Park, FL 32789
Corner lot • Updated kitchen • Formal dining room
3D WALKTHROUGH
$450,000
3 beds2 baths1,511 sq ft
2885 Roxbury Rd, Winter Park, FL 32789
Hardwood floors • Updated kitchen • Versatile bonus room
$485,000
2 beds2 baths970 sq ft
535 N Interlachen Ave #302, Winter Park, FL 32789
Top floor • Screened porch • Updated kitchen
Details provided by Stellar MLS as Distributed by MLS Grid and may not match the public record. Learn more.

More real estate resources

Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

Join us

Become an Agent
Get referrals
Careers

Find homes faster

Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

About us

Why Redfin?
Community Impact
Inclusion
Culture
Press
Investors
Blog
Real Estate News

Find us

Contact Us
Help Center
Advertise

Subsidiaries

Rent.
ApartmentGuide

Affiliated Business

Rocket Close
Rocket Mortgage

Countries

US flagUnited States

Canadian flagCanada

Copyright: © 2026 Redfin. All rights reserved.

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.