4469 Old Bear Run
Winter Park, FL 32792
5 Beds
4.5 Baths
4,288 sqft (on 0.74 acres)
5 Beds
4.5 Baths
4,288 sqft
(on 0.74 acres)
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Patio, Deck, Pool
Climate Control
Heating & Cooling
HOA
None
Price/Sqft
$420
Listed
162 days ago
Local Information
- Map ViewExplore the area around 4469 Old Bear Run.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
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.
Home Details for 4469 Old Bear Run
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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) |
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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 |
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Cumulative Days on Market: 155Days on Market: 162 |
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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 |
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Price List Price: $1,799,999Price Per Sqft: $420 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: Active |
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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 |
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Listing Agent Listing ID: O6375415 |
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Building Area Building Area: 5731 Square Feet |
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Not Senior Community |
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Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.74 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional |
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Business Information Ownership: Fee Simple |
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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 |
Last check for updates: about 4 hours ago
Listing Provided by: Keigan Lewis, (305) 393-8683
LPT REALTY, LLC, (877) 366-2213
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6375415
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
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Market trends in Winter Park
Last updated June 2026
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
Price History for 4469 Old Bear Run
| Date | Price | Event | Source |
|---|---|---|---|
| 07/20/2026 | $1,799,999 | PendingToActive | Stellar MLS #O6375415 |
| 07/14/2026 | $1,799,999 | Contingent | Stellar MLS #O6375415 |
| 05/22/2026 | $1,799,999 | PriceChange | Stellar MLS #O6375415 |
| 04/02/2026 | $1,850,000 | PriceChange | Stellar MLS #O6375415 |
| 02/09/2026 | $1,950,000 | Listed For Sale | Stellar MLS #O6375415 |
| 07/29/2025 | $1,899,000 | ListingRemoved | Stellar MLS #O6294027 |
| 06/10/2025 | $1,899,000 | PriceChange | Stellar MLS #O6294027 |
| 05/19/2025 | $1,996,000 | PriceChange | Stellar MLS #O6294027 |
| 04/23/2025 | $2,100,000 | PriceChange | Stellar MLS #O6294027 |
| 03/27/2025 | $2,200,000 | Listed For Sale | Stellar MLS #O6294027 |
| 07/28/2015 | $754,000 | Sold | N/A |
| 07/06/2015 | $829,000 | PendingToActive | Agent Provided |
| 07/06/2015 | $829,000 | Pending | Agent Provided |
| 07/02/2015 | $829,000 | PendingToActive | Agent Provided |
| 05/24/2015 | $829,000 | Pending | Agent Provided |
| 01/19/2015 | $829,000 | Listed For Sale | Agent Provided |
| 11/27/2014 | $829,000 | ListingRemoved | Agent Provided |
| 11/25/2014 | $829,000 | Listed For Sale | Agent Provided |
| 07/28/2014 | $700,000 | Sold | N/A |
| 05/24/2014 | $730,000 | Pending | Agent Provided |
| 05/24/2014 | $730,000 | Listed For Sale | Agent Provided |
| 08/05/2004 | $565,000 | Sold | N/A |
| 10/13/1997 | $270,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,733 |
| Assessment | $1,495,643 |
Home facts updated by county records
Comparable Sales for 4469 Old Bear Run
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.22 | Single-Family Home | $2,000,000 | 05/11/26 | 3 | 4.5 | 5,138 | |
0.14 | Single-Family Home | $824,950 | 02/26/26 | 4 | 3 | 3,111 | |
0.33 | Single-Family Home | $905,000 | 03/11/26 | 5 | 3.5 | 3,598 | |
0.54 | Single-Family Home | $1,010,000 | 09/30/25 | 5 | 4.5 | 3,839 | |
0.61 | Single-Family Home | $1,180,000 | 07/31/25 | 4 | 4 | 4,015 | |
0.63 | Single-Family Home | $1,206,400 | 10/15/25 | 4 | 3.5 | 3,321 | |
0.30 | Single-Family Home | $610,000 | 06/30/26 | 4 | 2.5 | 2,636 | |
0.53 | Single-Family Home | $800,200 | 10/03/25 | 4 | 3.5 | 3,074 | |
0.57 | Single-Family Home | $766,000 | 07/15/26 | 4 | 4 | 3,040 | |
0.25 | Single-Family Home | $514,000 | 12/30/25 | 4 | 2.5 | 2,101 |
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Assigned Schools
These are the assigned schools for 4469 Old Bear Run.
- Red Bug Elementary School
- PK-5
- Public
- 722 Students
6/10GreatSchools RatingParent Rating AverageI can’t say enough wonderful things about Dr. Thacker and the majority of the staff at Red Bug Elementary. They truly are an amazing school. They put together so many wonderful events for the students, and it’s clear how much they care. Dr. Thacker even spends her weekends at the park watching the students play—giving her personal time just to support and connect with our kids. That level of dedication and love for the students is truly special.Parent Review2mo ago - Tuskawilla Middle School
- 6-8
- Public
- 1067 Students
8/10GreatSchools RatingParent Rating AverageI believe parents should be able to raise concerns without feeling intimidated or experiencing negative consequences. In my experience, when I brought forward an issue, the situation escalated quickly rather than being addressed in a constructive and collaborative manner. This creates an environment where parents may hesitate to speak up. It may be beneficial to evaluate leadership practices and consider changes where necessary to ensure a more supportive and responsive environment for families. Some of the administration have worked together for a long time, and they seem to team up against students and families. Additionally, communication from staff has been inconsistent.Parent Review2mo ago - Lake Howell High School
- 9-12
- Public
- 2239 Students
7/10GreatSchools RatingParent Rating AverageAs a parent of a student at Lake Howell High School, I could not be happier with the experience my child has had here. From day one, the teachers and staff have shown genuine care for the students, providing not only strong academics but also the guidance and support kids need to succeed.My child has benefited from the wide range of AP and honors classes, as well as the many opportunities to explore sports, arts, and clubs. The school encourages balance—pushing for excellence in the classroom while also building character, leadership, and teamwork.What I appreciate most is the sense of community and inclusiveness. The administration communicates well with families, and I always feel confident that my child is safe and supported. It’s clear that the school is committed to preparing students for both college and life beyond high school.I am proud to have my child at Lake Howell High School and would recommend it to any family looking for a place where students are challenged, supported, and celebrated.Parent Review11mo ago 
Check out schools near 4469 Old Bear Run.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Keigan Lewis, LPT REALTY, LLC, (877) 366-2213
Agent Phone: (305) 393-8683
4469 Old Bear Run, Winter Park, FL 32792 is a 5 bedroom, 5 bathroom, 4,288 sqft single-family home built in 1978. This property is currently available for sale and was listed by Stellar MLS on Feb 9, 2026. The MLS # for this home is MLS# O6375415.