2827 Riddle Dr, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$253,200

Trulia Estimate
as of Sep 11, 2026
  • 3 Beds
  • 1 Bath
  • 1,260 sqft

2827 Riddle Dr, Winter Park, FL 32789

Home Highlights

Apartment
Built in 1958
1,260 sqft
$201/sqft

Local Information

  • Map ViewExplore the area around 2827 Riddle Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Property Representative: Mensny Oreste

Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.

This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living environment with central heating and air conditioning, complemented by ceiling fans for added comfort.

While rent does not include utilities such as gas, electricity, or water, you'll have the flexibility to set up services to suit your preferences. Winter Park offers a welcoming atmosphere, and this rental will connect you to everything you love about the area.

Don't miss the opportunity to make this lovely space your new home. Contact us today to schedule a viewing and see firsthand what this property has to offer!
2827 Riddle Dr, Winter Park, FL 32789 is a 3 bedroom, 1 bathroom, 1,260 sqft apartment built in 1958. It last sold for $115,000 on Nov 2, 2004 (4,900% above the $2,300 asking price). More recently, it was listed as a rental in April 2026 with an asking price of $2,300 per month. That rental listing was removed on May 20, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $253,200, with a rent estimate of $1,999/month.

Home Details for 2827 Riddle Dr

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 Year

Interior Features

Heating & Cooling
Air Conditioning

Exterior Features

Parking & Garage
Parking: Street Parking

Comparable Sales for 2827 Riddle Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4328 Edgewater Dr, Orlando, FL
0.58
Apartment
$199,000
06/29/26
1
600 sqft
1216 Virginia Dr, Orlando, FL
2.72
Apartment
$1,670,000
11/05/25
2
1
670 sqft
916 Lake Destiny Rd #E, Altamonte Springs, FL
3.18
Apartment
$125,000
08/28/26
3
2
1,112 sqft
5053 Maui Cir #14, Orlando, FL
2.98
Apartment
$220,000
08/09/26
2
2
1,250 sqft
400 E Colonial Dr #1003, Orlando, FL
3.18
Apartment
$170,000
09/30/25
2
2
1,109 sqft
285 Wymore 207 Rd, Altamonte Springs, FL
4.21
Apartment
$125,000
04/30/26
2
1
828 sqft
660 Osceola Ave #101, Winter Park, FL
2.73
Apartment
$2,232,000
04/17/26
3
3.5
2,714 sqft
385 Woodside 108 Dr, Altamonte Springs, FL
4.36
Apartment
$127,000
08/18/26
2
2
893 sqft
450 Cherrywood Gardens Dr, Maitland, FL
3.65
Apartment
$180,000
08/27/26
2
1.5
905 sqft
514 Orange 31 Dr, Altamonte Springs, FL
4.43
Apartment
$180,000
11/03/25
2
2
1,252 sqft
Home facts updated by county records

Nearby homes

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Rental Market Trends in Winter Park

Last updated Sep 2026
Trulia Rent Estimate$1,999/mo
Average rent
$1.92K
$84MoM
Available listings
272
View rental market trends in Winter Park, FL

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
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  • 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
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  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
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  • 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
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  • 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"
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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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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 20, 2026
Source: Zillow Rentals
ListingRemoved
$2,300
Apr 9, 2026
Source: Zillow Rentals
Listed For Rent
$2,300
Feb 26, 2023
Source: Stellar MLS #O6025369
ListingRemoved
Dec 29, 2022
Source: Stellar MLS #O6025369
Pending
$239,900
Nov 11, 2022
Source: Stellar MLS #O6025369
PriceChange
$239,900
Price decreased by 4%

Frequently asked questions about 2827 Riddle Dr

  • What is 2827 Riddle Dr estimated to be worth?
    Trulia's estimated value for 2827 Riddle Dr in Winter Park, FL is $253,200.
  • What is the price history for 2827 Riddle Dr?
    2827 Riddle Dr in Winter Park, FL last sold for $115,000 in November 2004.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $451K. That is down $833 from the prior month.
  • Does 2827 Riddle Dr have parking?
    Yes, 2827 Riddle Dr in Winter Park, FL has on-site parking.

Homes for rent near 2827 Riddle Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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