4469 Old Bear Run, Winter Park, Florida 32792

  • $1,799,999
  • $1,850,000

Overview

Property ID: HZO6375415
  • Single Family Residence, Residential
  • Property Type
  • 5
  • Bedrooms
  • 5
  • Bathrooms
  • 2
  • Garages
  • 5731 Sqft
  • Area Size

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.

  • Address: 4469 OLD BEAR RUN
  • City: Winter Park
  • State/county: FL
  • Zip/Postal Code: 32792
  • Country: US

Details

Updated on June 9, 2026 at 9:17 pm
  • Property ID HZO6375415
  • Price $1,799,999
  • Property Size 5731 Sqft
  • Land Area 0.74 Acres
  • Bedrooms 5
  • Bathrooms 5
  • Garages 2
  • Year Built 1978
  • Property Type Single Family Residence, Residential
  • Property Status Active

Additional details

  • Listing Terms Cash, Conventional
  • Roof Shingle
  • Utilities BB/HS Internet Available, Electricity Connected, Water Connected
  • Sewer Septic Tank
  • Cooling Central Air, Zoned
  • Heating Central, Electric, Zoned
  • Flooring Carpet, Ceramic Tile, Tile
  • County Seminole
  • Property Type Residential
  • Pool Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosure, Tile
  • Parking Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
  • Elementary School Red Bug Elementary
  • Middle School Tuskawilla Middle
  • High School Lake Howell High
  • Community Features Street Lights
  • Waterfront Lake Front
  • Architectural Style Florida

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