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4469 OLD BEAR RUN
WINTER PARK, FL, 32792
$1,799,999
5 Beds
4.5 Baths
4,288 SqFt
0.74 Acres
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MLS #O6375415 image #0
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:
$1,799,999
MLS #:
O6375415
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
PERVIS SURVEY FOR R E
Neighborhood:
32792winterparkaloma
Listed Date:
Feb 9, 2026
Finished Sq Ft:
4,288
Total Sq Ft:
5,731
Lot Size:
32,200 sqft / 0.74 acres (approx)
Year Built:
1978
FloridaWaterfrontLakefrontPoolPrimary Bedroom Main Floor32792 – Winter Park/aloma32792winterparkalomaPervis Survey For R ERed Bug ElementaryTuskawilla MiddleLake Howell HighBear GullyWaterPlease Check With Seminole County For Any Lease RestrictionsNo Minimum

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Schools

Elementary School:
Red Bug Elementary
Middle School:
Tuskawilla Middle
High School:
Lake Howell High

Interior

Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Carpet, Ceramic Tile, Porcelain Tile
Heating
Central, Electric, Zoned
Interior Features
Ceiling Fan(s), Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
One

Exterior

Architectural Style
Florida
Attached Garage YN
1
Construction Materials
Stucco, Wood Frame (FSC Certified)
Covered Spaces
2
Direction Faces
East
Exterior Features
Irrigation System, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors, Storage
Fencing
Fenced, Other
Garage Spaces
2
Lot Features
In County, Landscaped, Oversized Lot
Open Parking YN
1
Other Structures
Outdoor Kitchen, Shed(s), Storage
Parking Features
Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
Patio And Porch Features
Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security Gate, Security System, Security System Owned, Smoke Detector(s)
View
Water
Waterfront Features
Lake Front
Window Features
Blinds, Double Pane Windows, Tinted Windows

Financial

Tax Year
2024
Taxes
$10,710

Map

Community

Subdivisions in WINTER PARK

Market Summary

Current real estate data for Single Family in WINTER PARK as of Jun 09, 2026
319
Single Family Listed
87
Avg DOM
464
Avg $ / SqFt
$1,338,110
Avg List Price

Property Summary

    Located in the PERVIS SURVEY FOR R E subdivision, 4469 OLD BEAR RUN WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32792. It is listed for $1,799,999 and features 5 beds, 5 baths, and has approximately 4,288 square feet of living space, and was originally constructed in 1978. The current price per square foot is $420. The average price per square foot for Single Family listings in WINTER PARK is $464. The average listing price for Single Family in WINTER PARK is $1,338,110. To schedule a showing of MLS#o6375415 at 4469 OLD BEAR RUN in WINTER PARK, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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