2803 RIDDLE DRIVE, Winter Park, FL 32789
Property image
Property image
FOR SALE
0.25 ACRES

$549,900

Original price: $569,000
  • 3 Beds
  • 2.5 Baths
  • 1,709 sqft (on 0.25 acres)

2803 RIDDLE DRIVE, Winter Park, FL 32789

Est. Mortgage $3,922/mo*
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We estimate this home will sell faster than 90% nearby.

Home Highlights

Single-Family Home
Built in 1955
0.25 acre lot
$322/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 2803 RIDDLE DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 1 hour 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
We estimate this home will sell faster than 90% nearby.

Home Details for 2803 RIDDLE DRIVE

Interior Features

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: 1709 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Sprinkler MeterAppliances: Dishwasher, Disposal, Electric Water Heater, Microwave, RefrigeratorDishwasherDisposalLaundry: In GarageMicrowaveRefrigerator
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

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, Patio, PorchFencing: FencedVegetation: Mature Landscaping, Trees/LandscapedOther Structures: Shed(s), StorageExterior: 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

Days on Market

Cumulative Days on Market: 46Days on Market: 56

Property Information

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

Price & Status

Price
List Price: $549,900Price Per Sqft: $322

Active Status

MLS Status: Active

Location

Direction & Address
City: WINTER PARKCommunity: FAIRSHORES PLACE
School Information
Elementary School: Killarney ElemJr High / Middle School: College Park MiddleHigh School: Edgewater High

Agent Information

Listing Agent
Listing ID: O6423829

Building

Building Area
Building Area: 2109 Square Feet

Community

Community Features: NoneNot Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.25 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6423829Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-022229260000040-R-N

Additional Information

None

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % 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.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
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  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
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  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
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  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
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  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
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  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
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  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
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  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
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  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
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  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

Home Value

Trulia Estimate
$534K
Since last month
Decreased$23K (-4.1%)
Since last year
Increased$72K (+15.5%)
Since last sale
Increased$305K (+132.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +108% in the last 10 years
MonthEstimated value
2026
August 2026$535K
August 2026$534K
July 2026$557K
June 2026$493K
May 2026$482K
April 2026$481K
March 2026$478K
February 2026$472K
January 2026$466K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
105 CONRAD COURT, Winter Park, FL
0.12
Single-Family Home
$429,999
10/21/25
3
2
1,573
709 ALTON AVENUE, Orlando, FL
0.18
Single-Family Home
$256,250
08/25/26
4
2
1,665
320 GRANADA DRIVE, Winter Park, FL
0.23
Single-Family Home
$360,200
01/15/26
3
2
1,401
4401 SANTEE STREET, Orlando, FL
0.26
Single-Family Home
$305,000
07/23/26
3
2
1,050
742 CANOVIA AVENUE, Orlando, FL
0.20
Single-Family Home
$450,000
09/29/25
3
2
1,372
2611 LOTAFUN AVENUE, Winter Park, FL
0.31
Single-Family Home
$449,000
08/12/26
3
2
1,838
758 CANOVIA AVENUE, Orlando, FL
0.24
Single-Family Home
$415,000
05/01/26
3
2
1,354
861 ALTON AVENUE, Orlando, FL
0.36
Single-Family Home
$423,000
08/27/26
3
2
1,482
819 CANOVIA AVENUE, Orlando, FL
0.34
Single-Family Home
$426,000
08/06/26
3
2
1,681
2381 ROXBURY ROAD, Winter Park, FL
0.37
Single-Family Home
$470,000
12/23/25
3
2
1,785

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2739 RIDDLE DRIVE, Winter Park, FL 32789
0.03
$628,000
4
2.5
1,881
Off Market
2886 ROXBURY ROAD, Winter Park, FL 32789
0.12
$316,400
3
1
1,162
Off Market
2827 EUSTON ROAD, Winter Park, FL 32789
0.17
$337,800
4
2
1,568
Off Market
105 CONRAD COURT, Winter Park, FL 32789
0.12
$428,300
3
2
1,573
Off Market
2891 ROXBURY ROAD, Winter Park, FL 32789
0.14
$401,400
3
2
1,477
Off Market
2612 ROXBURY ROAD, Winter Park, FL 32789
0.18
$629,900
5
3
2,472
For Sale
2721 SALISBURY BOULEVARD, Winter Park, FL 32789
0.21
$350,900
2
1
1,080
Off Market
2877 EUSTON ROAD, Winter Park, FL 32789
0.18
$466,900
2
2
1,030
Off Market
709 ALTON AVENUE, Orlando, FL 32804
0.18
$256,250
4
2
1,665
Recently Sold
2710 EUSTON ROAD, Winter Park, FL 32789
0.23
$551,100
4
3
1,946
Off Market
2541 ROXBURY RD, Winter Park, FL 32789
0.23
$398,900
3
2
1,210
Off Market

Price and Tax history

DateEventPrice
Aug 25, 2026
Source: Stellar MLS #O6423829
PriceChange
$549,900
Price decreased by 3%
Jul 20, 2026
Source: Stellar MLS #O6423829
PriceChange
$569,000
Price decreased by 3%
Jul 10, 2026
Source: Stellar MLS #O6423829
Listed For Sale
$589,000
May 12, 2025
Source: Zillow Rentals
ListingRemoved
$2,800
May 9, 2025
Source: Zillow Rentals
Listed For Rent
$2,800

LGBTQ Local Legal Protections

Allie George, CORCORAN PREMIER REALTY, (407) 965-1155
Agent Phone: (407) 457-4815

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Frequently asked questions about 2803 RIDDLE DRIVE

  • What is the estimated monthly payment for 2803 RIDDLE DRIVE?
    Based on a $549,900 list price with 20% down at today's rates, the estimated monthly payment for 2803 RIDDLE DRIVE in Winter Park, FL is approximately $3,938 (about $2,887 principal & interest, $976 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 2803 RIDDLE DRIVE compare to homes in Winter Park?
    2803 RIDDLE DRIVE in Winter Park, FL is listed at $549,900, about 22% above the $451K median sale price in Winter Park.
  • What do residents say about Winter Park?
    Residents describe Winter Park, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Park, FL.
  • What are the closest schools to 2803 RIDDLE DRIVE?
    The closest schools to 2803 RIDDLE DRIVE in Winter Park, FL are College Park Middle School (rated 3/10), Edgewater High School (rated 6/10), Killarney Elementary School (Pre-K, rated 4/10).
  • Does 2803 RIDDLE DRIVE have air conditioning?
    Yes, 2803 RIDDLE DRIVE in Winter Park, FL has air conditioning.
  • Does 2803 RIDDLE DRIVE have a pool?
    Yes, 2803 RIDDLE DRIVE in Winter Park, FL has a pool.
2803 RIDDLE DRIVE, Winter Park, FL 32789 is a 3 bedroom, 3 bathroom, 1,709 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.