4285 Bear Gully Rd, Winter Park, FL 32792
OFF MARKET

4285 Bear Gully Rd
Winter Park, FL 32792

  • 5 Beds
  • 4 Baths
  • 3,490 sqft

$1,700,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $11,775/mo*
Refinance Your Home

$1,700,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $11,775/mo*
Refinance Your Home
5 Beds
4 Baths
3,490 sqft

Local Information

  • Map ViewExplore the area around 4285 Bear Gully Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1953
Living Area
3,490 sqft
Price/Sqft
$487

About this House

This single-family home is located at 4285 Bear Gully Rd, Winter Park, FL. 4285 Bear Gully Rd is in Winter Park, FL and in ZIP code 32792. This property has 5 bedrooms, 4 bathrooms and approximately 3,490 sqft of floor space. This property was built in 1953.
4285 Bear Gully Rd, Winter Park, FL 32792 is a 5 bedroom, 4 bathroom, 3,490 sqft single-family home built in 1953. It last sold for $605,000 on Feb 14, 2011. It is currently off market. The Trulia Estimate is $1,700,900, with a rent estimate of $4,601/month.

Home Details for 4285 Bear Gully Rd

Interior Features

Interior Details
Basement
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1953Year Updated: 1953
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
Exterior: Cement Concrete

Community

Units in Building: 1

Price History for 4285 Bear Gully Rd

DatePriceEventSource
02/14/2011$605,000Sold
Stellar MLS #O5021618
11/30/2007$1,495,000ListingRemovedAgent Provided
11/14/2007$1,495,000Listed For SaleAgent Provided
05/05/2006$1,500,000Sold
N/A
04/10/2001$545,000Sold
N/A
08/04/1999$400,000Sold
N/A

Market trends in Winter Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$452K
$7.33KMoM
Sale-to-List Price
97.7%
0.2%MoM
Price per sq ft
$288
$1MoM
Available listings
380
7MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$13,749
Assessment$982,732
Home facts updated by county records

Comparable Sales for 4285 Bear Gully Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5325 CYPRESS RESERVE PLACE, Winter Park, FL
0.20
Single-Family Home
$905,000
03/11/26
5
3.5
3,598
7895 PLEASANT PINE CIRCLE, Winter Park, FL
0.43
Single-Family Home
$719,000
11/19/25
5
3.5
3,568
2880 OLD CASTLE DRIVE, Winter Park, FL
0.30
Single-Family Home
$1,010,000
09/30/25
5
4.5
3,839
4190 BEAR GULLY ROAD, Winter Park, FL
0.17
Single-Family Home
$465,000
07/07/26
4
2.5
2,058
2890 WILD GINGER COURT, Winter Park, FL
0.37
Single-Family Home
$893,000
10/09/25
4
4.5
3,408
2791 MEADOW SAGE COURT, Oviedo, FL
0.39
Single-Family Home
$824,950
02/26/26
4
3
3,111
4048 GILDER ROSE PLACE, Winter Park, FL
0.41
Single-Family Home
$1,206,400
10/15/25
4
3.5
3,321
7864 PLEASANT PINE CIRCLE, Winter Park, FL
0.38
Single-Family Home
$550,000
10/23/25
4
2.5
2,182
7888 PLEASANT PINE CIRCLE, Winter Park, FL
0.43
Single-Family Home
$625,000
11/03/25
4
2.5
2,267
7988 PLEASANT PINE CIRCLE, Winter Park, FL
0.47
Single-Family Home
$596,500
10/02/25
4
2.5
2,267

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 4285 Bear Gully Rd.
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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

132 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

51 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

124 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

120 rentals with a pool in Winter Park, FL

Explore by feature - Washer/dryer

110 rentals with a washer/dryer in Winter Park, FL

Explore by feature - Outdoor Space

58 rentals with an outdoor space in Winter Park, FL

Homes for sale near 4285 Bear Gully Rd

Skip to last item
Skip to first item

Off Market Homes Near 4285 Bear Gully Rd

Skip to last item
Skip to first item