4445 Old Bear Run, Winter Park, FL 32792
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Property image
OFF MARKET

4445 Old Bear Run
Winter Park, FL 32792

  • 4 Beds
  • 4 Baths
  • 3,675 sqft (on 0.71 acres)

$1,993,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $13,548/mo*
Refinance Your Home

$1,993,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $13,548/mo*
Refinance Your Home
4 Beds
4 Baths
3,675 sqft
(on 0.71 acres)

Local Information

  • Map ViewExplore the area around 4445 Old Bear Run.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautifully Well Kept 3,675 Sq. Ft. "Custom Lakefront" Home Situated On The East Side of Bear Gully Lake. A Private Access Only Lake For Skiing, Fishing And Recreational Use Located In Northeast Winter Park In Seminole County. The Home Offers Views of Screened Swimming Pool, Lakefront And Dock From Most Every Room In The Home. This 4 Bedroom, 3 Full And One 1/2 Bath Home Is The Perfect Home For Entertaining Guests And Contains A Total of 5,384 Sq. Ft. of Covered Roof Area With A 3 Way Split Bedroom Floor Plan, A Huge 15' X 22' Kitchen With Island Cooking/Preparation Area, Separate Dinette Room Off The Kitchen Overlooks A Serine Creek View To The North. Large Private Office / Study With Built In Book Shelves And Pocket Doors For Privacy. A Private Sitting Room And 4th Bedroom Can Be Used As An In-Law Suite Or Guest Retreat Which Also Has Views of The Screened Pool, Boat Dock & Lake. Expansive Great Room Floor Plan With Fireplace And Vaulted Ceilings Throughout The Home Adjoins The Open Dining Room. Also An Over Sized 3 Car Garage With Workbench With Plenty of Additional Storage. The Fishing Dock Also Has 2 Covered Boat Lifts, Sitting Area & Plenty of Room For Fishing. Large Front Yard For The Children To Play On A Private Street With Ample Parking & Pavered Driveway. Please Feel Free To Inquire About Additional Photos of The Home To Be Forwarded To You. Must See This Home To Appreciate Everything It Has To Offer.
4445 Old Bear Run, Winter Park, FL 32792 is a 4 bedroom, 4 bathroom, 3,675 sqft single-family home built in 1994. It last sold for $795,000 on Mar 20, 2012. It is currently off market. The Trulia Estimate is $1,993,600, with a rent estimate of $5,342/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4445 Old Bear Run

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco, Wood, BrickFoundation Type: FootingPatio
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1994Year Updated: 2014
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.71 acres

Price History for 4445 Old Bear Run

DatePriceEventSource
03/20/2012$795,000Sold
N/A

Market trends in Winter Park

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$445K
$11.4KMoM
Sale-to-List Price
97.4%
0.5%MoM
Price per sq ft
$289
$4MoM
Available listings
371
6MoM
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Property Tax and Assessment

Year2025
Tax$13,109
Assessment$1,685,940
Home facts updated by county records

Comparable Sales for 4445 Old Bear Run

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2791 Meadow Sage Ct, Oviedo, FL
0.17
Single-Family Home
$824,950
02/26/26
4
3
3,111
2220 Fairglenn Way, Winter Park, FL
0.22
Single-Family Home
$610,000
06/30/26
4
2.5
2,636
4107 Gabriella Ln, Winter Park, FL
0.50
Single-Family Home
$800,200
10/03/25
4
3.5
3,074
4048 Gilder Rose Pl, Winter Park, FL
0.67
Single-Family Home
$1,206,400
10/15/25
4
3.5
3,321
2820 Bear Island Point, Winter Park, FL
0.29
Single-Family Home
$2,000,000
05/11/26
3
4.5
5,138
5325 Cypress Reserve Pl, Winter Park, FL
0.41
Single-Family Home
$905,000
03/11/26
5
3.5
3,598
2530 Creekview Cir, Oviedo, FL
0.25
Single-Family Home
$514,000
12/30/25
4
2.5
2,101
4052 Gilder Rose Pl, Winter Park, FL
0.65
Single-Family Home
$1,180,000
07/31/25
4
4
4,015
1909 Cyril Ct, Winter Park, FL
0.53
Single-Family Home
$684,000
12/23/25
3
3.5
3,102
2880 Old Castle Dr, Winter Park, FL
0.59
Single-Family Home
$1,010,000
09/30/25
5
4.5
3,839

Nearby homes

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Assigned Schools

These are the assigned schools for 4445 Old Bear Run.
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 594 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."
    0
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  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
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  • 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
    Flag
  • 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
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  • 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
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  • 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
    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
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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
    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
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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
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  • 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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Homes for sale near 4445 Old Bear Run

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Off Market Homes Near 4445 Old Bear Run

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