4469 Old Bear Run, Winter Park, FL 32792
Local realty services provided by:Bingham Realty ERA Powered
Listed by: keigan lewis
Office: lpt realty, llc.
MLS#:O6375415
Source:MFRMLS
Price summary
- Price:$1,799,999
- Price per sq. ft.:$314.08
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....
Contact an agent
Home facts
- Year built:1978
- Listing ID #:O6375415
- Added:146 day(s) ago
- Updated:July 06, 2026 at 12:43 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Flooring:Carpet, Ceramic Tile, Tile
- Kitchen Description:Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Exhaust Fan, Microwave, Refrigerator, Solid Wood Cabinets, Wine Refrigerator
- Bedroom Description:Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
- Living area:4,288 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Zoned
- Central air:Yes
Structure and exterior
- Roof:Shingle
- Year built:1978
- Building area:4,288 sq. ft.
- Lot area:0.74 Acres
- Lot Features:Landscaped, Oversized, Paved
- Architectural Style:Florida
- Construction Materials:Frame, Stucco
- Exterior Features:Covered Porch/Patio, Deck, Enclosed, Front Porch, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Patio, Porch, Rear Porch, Screened
- Foundation Description:Slab
- Levels:1 Story
Schools
- High school:Lake Howell High
- Middle school:Tuskawilla Middle
- Elementary school:Red Bug Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Septic Tank
Finances and disclosures
- Price:$1,799,999
- Price per sq. ft.:$314.08
- Tax amount:$10,710 (2024)
Features and amenities
- Appliances:Bar Fridge, Built-in Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Irrigation Equipment, Microwave, Refrigerator, Washer, Wine Refrigerator
- Laundry features:Dryer, Inside, Laundry Room, Washer
- Amenities:BB/HS Internet Available, Ceiling Fans(s), Irrigation Equipment, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Pool features:Automatic Cleaner, Gunite, In Ground, Pool/Deck, Private Pool, Salt Water, Screen Enclosure, Tile
Parking
- Parking description:Attached Garage, Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
- Garage:Yes
- Garage spaces:2
New listings near 4469 Old Bear Run
- New
$280,000Active2 beds 2 baths1,008 sq. ft.5184 Lazy Oaks Drive, WINTER PARK, FL 32792
MLS# O6422366Listed by: PAINE-ANDERSON PROPERTIES, INC - New
$299,900Active3 beds 2 baths1,998 sq. ft.7500 Waunatta Court, WINTER PARK, FL 32792
MLS# TB8525179Listed by: FUTURE HOME REALTY INC - New
$799,000Active4 beds 3 baths2,332 sq. ft.729 Monmouth Way, WINTER PARK, FL 32792
MLS# O6422168Listed by: KELLER WILLIAMS WINTER PARK - New
$450,000Active4 beds 2 baths1,525 sq. ft.1189 Lazy Hollow Place, WINTER PARK, FL 32792
MLS# O6422142Listed by: KELLER WILLIAMS CLASSIC
$475,000Active3 beds 2 baths1,622 sq. ft.3641 Hawthorne Lane, WINTER PARK, FL 32792
MLS# TB8519391Listed by: LPT REALTY, LLC
$439,000Pending3 beds 2 baths1,592 sq. ft.1612 Lawndale Circle, WINTER PARK, FL 32792
MLS# O6418472Listed by: TOP VALUE PROPERTIES LLC- New
$279,900Active2 beds 2 baths1,295 sq. ft.2305 Sun Valley Cir, Winter Park, Fl 32792, WINTER PARK, FL 32792
MLS# O6421422Listed by: MARKET CONNECT REALTY LLC - New
$85,000Active2 beds 2 baths1,085 sq. ft.252 Scottsdale Sq #252, WINTER PARK, FL 32792
MLS# O6421977Listed by: CHARLES RUTENBERG REALTY ORLANDO
$499,500Pending3 beds 2 baths2,067 sq. ft.7509 Glenmoor Lane, WINTER PARK, FL 32792
MLS# O6421887Listed by: RE/MAX PRIME PROPERTIES- New
$549,000Active3 beds 2 baths1,923 sq. ft.1956 Japonica Road, WINTER PARK, FL 32792
MLS# O6421731Listed by: PROPLOGIK REALTY INC