4469 Old Bear Run, Winter Park, FL 32792
Local realty services provided by:CENTURY 21 Affiliates
Listed by: keigan lewis
Office: lpt realty, llc.
MLS#:O6375415
Source:MFRMLS
Price summary
- Price:$1,950,000
- Price per sq. ft.:$340.25
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.
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Home facts
- Year built:1978
- Listing ID #:O6375415
- Added:13 day(s) ago
- Updated:February 22, 2026 at 07:37 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Living area:4,288 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Zoned
Structure and exterior
- Roof:Shingle
- Year built:1978
- Building area:4,288 sq. ft.
- Lot area:0.74 Acres
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:$1,950,000
- Price per sq. ft.:$340.25
- Tax amount:$10,710 (2024)
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