4469 OLD BEAR RUN, Winter Park, FL 32792
SOLD
SEP 11, 2026

$1,699,700

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 4,288 sqft (on 0.74 acres)

4469 OLD BEAR RUN, Winter Park, FL 32792

Est. Refi. Payment $12,129/mo*
Refinance Your Home
Currently Off Market - Sold Sep 11, 2026 for $1,700,000 (6% below list price)

Home Value

Trulia Estimate
$1.7M
Since last month
Increased$6K (+0.3%)
Since last year
Decreased$65K (-3.7%)
Since last sale
$400 (0%)
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 +100% in the last 10 years
MonthEstimated value
2026
September 2026$1.7M
August 2026$1.69M
July 2026$1.7M
June 2026$1.69M
May 2026$1.69M
April 2026$1.73M
March 2026$1.84M
February 2026$1.87M
January 2026$1.86M
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
2820 BEAR ISLAND POINTE, Winter Park, FL
0.22
Single-Family Home
$2,000,000
05/11/26
3
4.5
5,138
4048 GILDER ROSE PLACE, Winter Park, FL
0.63
Single-Family Home
$1,206,400
10/15/25
4
3.5
3,321
2880 OLD CASTLE DRIVE, Winter Park, FL
0.54
Single-Family Home
$1,010,000
09/30/25
5
4.5
3,839
2791 MEADOW SAGE COURT, Oviedo, FL
0.14
Single-Family Home
$824,950
02/26/26
4
3
3,111
2138 TALMAN COURT, Winter Park, FL
0.70
Single-Family Home
$1,450,000
08/27/26
4
5
4,249
1460 VIA SANGRO PLACE, Winter Park, FL
0.82
Single-Family Home
$1,500,000
12/23/25
7
4
5,111
2890 WILD GINGER COURT, Winter Park, FL
0.63
Single-Family Home
$893,000
10/09/25
4
4.5
3,408
2220 FAIRGLENN WAY, Winter Park, FL
0.30
Single-Family Home
$610,000
06/30/26
4
2.5
2,636

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
2664 TUSKAWILLA ROAD, Oviedo, FL 32765
0.10
$3,677,600
7
6
6,948
Off Market
2791 MEADOW SAGE COURT, Oviedo, FL 32765
0.14
$824,950
4
3
3,111
Recently Sold
4591 WHIMBREL PLACE, Winter Park, FL 32792
0.20
$480,000
3
2
1,942
Recently Sold
2730 MEADOW SAGE COURT, Oviedo, FL 32765
0.18
$1,460,200
7
6
4,997
Off Market
2742 MEADOW SAGE COURT, Oviedo, FL 32765
0.19
$1,518,200
6
6.5
5,245
Off Market
2746 MEADOW SAGE COURT, Oviedo, FL 32765
0.20
$988,100
5
4
3,180
Off Market
2820 BEAR ISLAND POINTE, Winter Park, FL 32792
0.22
$2,000,000
3
4.5
5,138
Recently Sold
4637 CREEKVIEW LANE, Oviedo, FL 32765
0.24
$515,000
4
2
1,819
Recently Sold
2530 CREEKVIEW CIRCLE, Oviedo, FL 32765
0.25
$514,000
4
2.5
2,101
Recently Sold
2524 CREEKVIEW CIRCLE, Oviedo, FL 32765
0.25
$483,300
4
2
1,847
Off Market

Local Information

  • Map ViewExplore the area around 4469 OLD BEAR RUN.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
0.74 acre lot
4,288 sqft
$396/sqft
2 Car Garage

About this House

Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
4469 OLD BEAR RUN, Winter Park, FL 32792 is a 5 bedroom, 5 bathroom, 4,288 sqft single-family home built in 1978. It last sold for $1,700,000 on Sep 11, 2026 (6% below the $1,799,999 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,699,700, with a rent estimate of $6,584/month.
Last check for updates: about 22 hours ago
Listed by Keigan Lewis, (305) 393-8683
LPT REALTY, LLC, (877) 366-2213
Bought with: Keigan Lewis, (305) 393-8683, LPT REALTY, LLC, (877) 366-2213
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6375415
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

Home Details for 4469 OLD BEAR RUN

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Great Room, Gym, Kitchen
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4288 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity Connected, Street Lights, Water ConnectedAppliances: Bar Fridge, Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Skylight(s)Door: Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding DoorsFlooring: Carpet, Ceramic Tile, Porcelain Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Porcelain Tile
View
Has a ViewView: Water, Lake
Security
Security: Security Gate, Security System, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, ScreenedFencing: Fenced, OtherVegetation: Mature LandscapingOther Structures: Outdoor Kitchen, Shed(s), StorageExterior: Irrigation System, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, StorageFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Electric Vehicle Charging Station(s),Garage Door Opener,Garage Faces Side
Pool
Pool: Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosure, TilePool
Frontage
WaterfrontWaterfront: Lake Front, Lake Privileges, Lift - Covered, Skiing AllowedRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: BEAR GULLY

Days on Market

Cumulative Days on Market: 164

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida
Building
Construction Materials: Stucco, Wood Frame (FSC Certified)Not a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 36213050100000050

Price & Status

Price
List Price: $1,799,999Price Per Sqft: $396/sqft
Status Change & Dates
Off Market Date: Wed Jul 29 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: PERVIS SURVEY FOR R E
School Information
Elementary School: Red Bug ElementaryJr High / Middle School: Tuskawilla MiddleHigh School: Lake Howell High

Building

Building Area
Building Area: 5731 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.74 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6375415Water ViewWater View: Water, LakeBack On Market Date: Mon Jul 20 2026Showing Advance Notice: 24Showing AttendedShowing Considerations: Pet(s) on PremisesShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12117-N-36213050100000050-R-N

Price and Tax history

DateEventPrice
Sep 11, 2026
Source: Stellar MLS #O6375415
Sold
$1,700,000
Aug 11, 2026
Source: Stellar MLS #O6375415
Pending
$1,799,999
Aug 8, 2026
Source: Stellar MLS #O6375415
ListingRemoved
$1,799,999
Aug 3, 2026
Source: Stellar MLS #O6375415
Pending
$1,799,999
Jul 20, 2026
Source: Stellar MLS #O6375415
PendingToActive
$1,799,999

Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

Around this home

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
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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
    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

Frequently asked questions about 4469 OLD BEAR RUN

  • What is 4469 OLD BEAR RUN estimated to be worth?
    Trulia's estimated value for 4469 OLD BEAR RUN in Winter Park, FL is $1,699,700.
  • What is the price history for 4469 OLD BEAR RUN?
    4469 OLD BEAR RUN in Winter Park, FL last sold for $1,700,000 in September 2026.
  • 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 $455K. That is up $4.03K from the prior month.
  • Does 4469 OLD BEAR RUN have air conditioning?
    Yes, 4469 OLD BEAR RUN in Winter Park, FL has air conditioning.
  • Does 4469 OLD BEAR RUN have a pool?
    Yes, 4469 OLD BEAR RUN in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

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