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4469 Old Bear Run

Winter Park, FL 32792
  • $1,799,999
  • STATUS: Active
  • ON SITE: 125 Days
  • MLS #: O6375415
$1,799,999
  • 5
    BEDS
  • 0.74
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 4,288
    SQFT
  • $420
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1978
County:

School Information

Elementary School:
Middle School:
High School:

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.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-06-15T19:45:26.837.
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4469 Old Bear Run Winter Park, FL 32792

  • Price: $1,799,999
  • Status: Active
  • On Site: 125 Days
  • MLS #: O6375415
5
Beds
4
Baths
1
½ Baths
0.74
Acres
4,288
SQFT
$420
$/SQFT
1978
Built
Neighborhood:
Pervis Survey For R E
County:
Seminole
Area:
Winter Park/Aloma
Elementary School:
Red Bug Elementary
Middle School:
Tuskawilla Middle
High School:
Lake Howell High
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.
Exterior Features

Architectural Style Florida Attached Garage Yn Yes Carport Yn No Construction Materials StuccoWood Frame (FSC Certified) Covered Spaces 2 Direction Faces East Exterior Features Irrigation SystemOutdoor GrillOutdoor KitchenOutdoor ShowerSliding DoorsStorage Fencing FencedOther Foundation Details Slab Lot Features In CountyLandscapedOversized Lot Open Parking YN Yes Other Structures Outdoor KitchenShed(s)Storage Parking Features Circular DrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces Side Patio And Porch Features CoveredDeckEnclosedFront PorchPatioPorchRear PorchScreened Pool Features Auto CleanerDeckGuniteIn GroundLightingSalt WaterScreen EnclosureTile Pool Private Yn Yes Road Frontage Type Street Paved Road Surface Type Paved Roof Shingle Spa YN No View Water Water Access Lake Water Access Yn Yes Water Body Name BEAR GULLY Water Extras Lift - CoveredSkiing Allowed Water Extras Yn Yes Water View Lake Water View Yn Yes Waterfront Features Lake Front Waterfront Yn Yes

Interior Features

Additional Rooms AtticGreat RoomInside Utility Appliances Bar FridgeBuilt-In OvenConvection OvenCooktopDishwasherDisposalDryerElectric Water HeaterExhaust FanMicrowaveRefrigeratorWasherWine Refrigerator Building Area Total 5731 Cooling Central AirZoned Cooling YN Yes Fireplace Yn No Flooring CarpetCeramic TilePorcelain Tile Furnished Unfurnished Heating CentralElectricZoned Heating YN Yes Interior Features Ceiling Fan(s)Open FloorplanPrimary Bedroom Main FloorSkylight(s)Solid Wood CabinetsSplit BedroomThermostatVaulted Ceiling(s)Walk-In Closet(s) Laundry Features InsideLaundry Room Levels One Sewer Septic Tank Water Source Canal/Lake For IrrigationPublic Window Features BlindsDouble Pane WindowsTinted Windows

Property Features

Additional Lease Restrictions Please check with Seminole county for any lease restrictions Additional Parcels YN No Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code AEX Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventional Minimum Lease No Minimum New Construction Yn No Number Of Septics 1 Occupant Type Owner Ownership Fee Simple Property Sub Type Single Family Residence Realtor Info As-IsSignTermite Bond/Warranty Security Features Security GateSecurity SystemSecurity System OwnedSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 10710 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableElectricity ConnectedStreet LightsWater Connected Zoning R-1AA


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of LPT REALTY, LLC: 877-366-2213.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-06-15T19:45:26.837.
 
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