New Listing - 02/09/2026

$1,950,000 ($454.76 per sqft)

Est. Mortgage $9,104/mo *

Quick Pre-Approval

4469 OLD BEAR RUN, Winter Park, FL, 32792

4469 OLD BEAR RUN, Winter Park, FL, 32792

8 rooms

5 beds

4 Full / 1 Half baths

1978

Florida

4,288 sqft

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.


Status:

Active

Type:

Single-family residential

Furnished Remarks:

Unfurnished

Laundry Remarks:

Inside, Laundry Room

Subdivision:

PERVIS SURVEY FOR R E

Garage:

2-car Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side

Heating:

Central, Electric, Zoned

Cooling:

Central Air, Zoned

Acreage:

0.74

Est. Taxes:

$10,710

Construction

Stucco, Wood Frame (FSC Certified)

Utilities

BB/HS Internet Available, Electricity Connected, Street Lights, Water Connected

Lot Description:

In County, Landscaped, Oversized Lot

View Description:

Water

Elementary School:

Red Bug Elementary

Middle School:

Tuskawilla Middle

High School:

Lake Howell High

Days on Market:

6

Appliances:

Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator

Pool:

Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosure, Tile

Min Lease Term:

No Minimum

MLS #:

O6375415


Community Info

School Info

Walk Score

Yelp


Listing courtesy of LPT Realty 877-366-2213