4469 OLD BEAR RUN, Winter Park, FL 32792

• 5 beds |
• 5 baths |
• 4,288 sqft

Property 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.

Listing Status:

Active

Date Added:

February 9, 2026

Data Last Updated:

February 9, 2026 at 7:23PM

Listing Office:

LPT REALTY, LLC : 877-366-2213

Listing Agent:

Keigan Lewis : 305-393-8683

MLS ID:

O6375415

Interior

• General: Ceiling Fans(s)Open FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsSplit BedroomThermostatVaulted Ceiling(s)Walk-In Closet(s)
• Rooms: AtticGreat RoomInside Utility
• Appliances: Bar FridgeBuilt-In OvenConvection OvenCooktopDishwasherDisposalDryerElectric Water HeaterExhaust FanMicrowaveRefrigeratorWasherWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: CarpetCeramic TileTile
• A/C: Central AirZoned
• Heating: CentralElectricZoned

Exterior

• General: Outdoor GrillOutdoor KitchenOutdoor ShowerSliding DoorsStorage
• Style: Florida
• Other Structures: Outdoor KitchenShed(s)StorageEnclosedPorchFront PorchDeckRear PorchScreenedPatioCovered
• Pool: Auto CleanerDeckGuniteIn GroundLightingSalt WaterScreen EnclosureTile
• Parking: Circular DrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces Side

Construction

• Roofing: Shingle
• Windows: Skylight(s)BlindsDouble Pane WindowsTinted Windows
• General: StuccoFrameOneSlab

Location

• Road/Access: Paved
• Originating MLS: Stellar MLS
• County: Seminole

Lot

• Zoning: R-1AALOT 5 SURVEY FOR R E PERVIS DB 151 PG 319 S C R36-21-30-501-0000-0050
• View: Water
• Fencing: FencedOther

Utilities

• Utilities: BB/HS Internet AvailableElectricity ConnectedWater Connected
• Water: Canal/Lake For IrrigationPublic
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple