$1,799,999
4469 Old Bear Run
Winter Park, FL 32792
Listing updated: July 20, 2026 at 10:04 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history155 days on market
- Status: ActiveJul 20, 2026
- Listed$1,950,000Feb 9, 2026
- Price reduced$1,799,999
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 155
- Subdivision
- Pervis Survey For R E
- County
- Seminole
- Year built
- 1978
- Living area
- 4,288 sq ft
- Price/sq ft
- $420
- Building area
- 5,731 sq ft (Public Records)
- Lot size
- 32,200 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- AE, X (12117C0260F)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $10,710 (2024)
- Parcel #
- 36-21-30-501-0000-0050
- Zoning
- R-1AA
- MLS #
- O6375415
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Carpet, Ceramic Tile, Tile
- Appliances
- Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Ceiling Fans(s), Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- East
Heating & Cooling
- Heating
- Central, Electric, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Please check with Seminole county for any lease restrictions
Exterior & Construction
- Exterior features
- Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors, Storage
- Construction materials
- Stucco, Frame
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Canal/Lake For Irrigation, Public
- Utilities
- BB/HS Internet Available, Electricity Connected, Water Connected
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Great Room | First | 31x34 |
| Kitchen | First | 15x18 |
| Gym | First | 12x19 |
| Primary Bedroom | First | 20x19 |
| Bedroom 2 | First | 19x18 |
| Bedroom 3 | First | 20x19 |
| Bedroom 4 | First | 12x15 |
| Bedroom 5 | First | 10x11 |
Listing Details
- Listing date
- 2026-01-05
- On market date
- 2026-02-09
- Original list price
- $1,950,000
- Occupant type
- Owner
- MLS area
- 32792 - Winter Park/Aloma
- Listing AOR
- Orlando Regional
- Status changed
- 2026-07-20
- Tax legal description
- LOT 5 SURVEY FOR R E PERVIS DB 151 PG 319 S C R
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From SR 417 exit West on Aloma, right on Tuscawilla Rd, Left on Old Bear Run.
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