4469 Old Bear Run, Winter Park, FL 32792
For Sale $1,950,000
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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.
Ceiling Fans(s)
Open Floorplan
Primary Bedroom Main Floor
Solid Wood Cabinets
Split Bedroom
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Taxes: $10,710.00
Tax Year: 2024
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sliding Doors
Storage
Bar Fridge
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Microwave
Refrigerator
Washer
Wine Refrigerator
Water
Lake Front
Elementary School: Red Bug Elementary
Middle School: Tuskawilla Middle
Junior High: Tuskawilla Middle
High School: Lake Howell High
MLS Area: 32792 - Winter Park/Aloma
Price per Square Feet: $454.76
Water: Canal/Lake For Irrigation, Public
Lot Desc.: In County, Landscaped, Oversized Lot, Paved
Construction: Stucco, Frame
Date Listed: 2026-02-09 12:54:05
Pool: Yes
Pool Type: Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosu
Private Spa: No
Furnished: Unfurnished
Windows: Skylight(S), Blinds, Double Pane Windows, Tinted Windows
Parking: Circular Driveway, Electric Vehicle Charging Station(S), Garage Door Opener, Garage Faces Side
Garage Spaces: 2
Flooring: Carpet, Ceramic Tile, Tile
Roof: Shingle
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Sewer: Septic Tank
Listing Courtesy Of: Lpt Realty, Llc
Keiganlewis@legacyestatesfl.com
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.
Property Details
Price: $1,950,000
Sq Ft: 4,288
($455 per
sqft)
Bedrooms: 5
Bathrooms: 4
Partial Baths: 1
City: Winter Park
County: Seminole
Type: Single Family Reside
Development: Pervis Survey For R E
Acres: 0.74
Virtual Tour/Floorplan: View
Year Built: 1978
Listing Number: O6375415
Status Code: A-Active
Taxes: $10,710.00
Tax Year: 2024
Garage:
2
Furnishings: Unfurnished
Interior Features:
Ceiling Fans(s)
Open Floorplan
Primary Bedroom Main Floor
Solid Wood Cabinets
Split Bedroom
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Financial Information:
Taxes: $10,710.00
Tax Year: 2024
Exterior Features:
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Sliding Doors
Storage
Equipment:
Bar Fridge
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Microwave
Refrigerator
Washer
Wine Refrigerator
View:
Water
Waterfront Description:
Lake Front
School Information:
Elementary School: Red Bug Elementary
Middle School: Tuskawilla Middle
Junior High: Tuskawilla Middle
High School: Lake Howell High
Additional Information:
MLS Area: 32792 - Winter Park/Aloma
Price per Square Feet: $454.76
Water: Canal/Lake For Irrigation, Public
Lot Desc.: In County, Landscaped, Oversized Lot, Paved
Construction: Stucco, Frame
Date Listed: 2026-02-09 12:54:05
Pool: Yes
Pool Type: Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosu
Private Spa: No
Furnished: Unfurnished
Windows: Skylight(S), Blinds, Double Pane Windows, Tinted Windows
Parking: Circular Driveway, Electric Vehicle Charging Station(S), Garage Door Opener, Garage Faces Side
Garage Spaces: 2
Flooring: Carpet, Ceramic Tile, Tile
Roof: Shingle
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Sewer: Septic Tank
Map of 4469 Old Bear Run, Winter Park, FL 32792
Listing Courtesy Of: Lpt Realty, Llc
Keiganlewis@legacyestatesfl.com