2803 Riddle Dr, Winter Park, FL 32789
Property image
Property image
FOR SALE
0.25 ACRES

2803 Riddle Dr
Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,637 sqft (on 0.25 acres)

$589,000

Est. Mortgage $4,058/mo*

$589,000

Est. Mortgage $4,058/mo*
3 Beds
2.5 Baths
1,637 sqft
(on 0.25 acres)
We estimate this home will sell faster than 87% nearby.

Local Information

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

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
3 days ago

Home Details for 2803 Riddle Dr

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: 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

Exterior Features

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

Days on Market

Cumulative Days on Market: 2Days on Market: 3

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: $589,000Price Per Sqft: $360

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
Last check for updates: about 12 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

Market trends in Winter Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$452K
$7.33K
MoM
Sale-to-List Price
97.7%
0.2%
MoM
Price per sq ft
$288
$1
MoM
Available listings
380
7
MoM

Price History for 2803 Riddle Dr

DatePriceEventSource
07/10/2026$589,000Listed For SaleStellar MLS #O6423829
05/12/2025$2,800ListingRemovedZillow Rentals
05/09/2025$2,800Listed For RentZillow Rentals
01/09/2021ListingRemovedN/A
05/03/2019$2,250ListingRemovedN/A
03/31/2019$2,250Listed For RentN/A
10/31/2014$229,900Sold
N/A
02/27/2014$249,000ListingRemovedAgent Provided
02/08/2014$249,000Listed For SaleAgent Provided
09/06/2012$73,200Sold
N/A
01/26/2007$265,000Sold
N/A
09/29/2005$229,000Sold
N/A

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Property Tax and Assessment

Year2024
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

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Assigned Schools

These are the assigned schools for 2803 Riddle Dr.
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 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.
  • 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."
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
  • 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. "
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
  • 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."
  • 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 "
  • 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."
  • 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. "
  • 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 "
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
  • 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"
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
  • 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."
  • 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."
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
  • 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 "
  • 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 !"
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
  • 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. "
  • 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."
  • 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."
  • 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"
  • 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. "
  • 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"
  • 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. "
  • 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."
  • 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"
  • 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. "
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
  • 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."
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
  • 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."
  • 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. "
  • 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 "

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.