4469 Old Bear Run, FL
Stellar MLS

$1,799,999

4469 Old Bear Run

Winter Park, FL 32792

Listing updated: May 22, 2026 at 1:17 PM ET

Active
5
Beds
5
Baths
4,288
Sq Ft
0.74
Acres
1978
Built
WaterfrontWater accessPrivate pool$420/sqft360° tour
Single Family Residence

Property type

1978

Year built

32,200 sqft

Lot size

$420

Price / sq ft

No HOA

HOA dues

102

Days on market

2

Garage spaces

AE, X

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$9,102
Property taxes$893
Home insurance (est.)$825

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history102 days on market

  1. Status: Active
    Feb 9, 2026
  2. Listed$1,950,000
    Feb 9, 2026
  3. Price reduced$1,799,999

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
102
Subdivision
Pervis Survey For R E
County
Seminole
Year built
1978
Living area
4,288 sq ft
Price/sq ft
$420
Building area
5,731 sq ft (Public Records)
Lot size
32,200 sq ft
Lot category
1/2 to less than 1
Flood zone
AE, X (12117C0260F)
Garage
2 spaces
Pool
Private pool
Annual taxes
$10,710 (2024)
Parcel #
36-21-30-501-0000-0050
Zoning
R-1AA
MLS #
O6375415

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Interior Details

Bedrooms
5
Full bathrooms
4
Half bathrooms
1
Flooring
Carpet, Ceramic Tile, Tile
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
Interior features
Ceiling Fans(s), Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
East

Heating & Cooling

Heating
Central, Electric, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Please check with Seminole county for any lease restrictions

Exterior & Construction

Exterior features
Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors, Storage
Construction materials
Stucco, Frame
Roof
Shingle
Foundation
Slab
Pool
Private pool
Waterfront
Yes
Water access
Yes
Water view
Yes
Road surface
Paved

Utilities

Sewer
Septic Tank
Water source
Canal/Lake For Irrigation, Public
Utilities
BB/HS Internet Available, Electricity Connected, Water Connected

Schools

ElementaryBRed Bug ElementaryGreatSchools ↗
MiddleATuskawilla MiddleGreatSchools ↗
High SchoolALake Howell HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Great RoomFirst31x34
KitchenFirst15x18
GymFirst12x19
Primary BedroomFirst20x19
Bedroom 2First19x18
Bedroom 3First20x19
Bedroom 4First12x15
Bedroom 5First10x11

Listing Details

Listing date
2026-01-05
On market date
2026-02-09
Original list price
$1,950,000
Occupant type
Owner
MLS area
32792 - Winter Park/Aloma
Listing AOR
Orlando Regional
Status changed
2026-02-09
Tax legal description
LOT 5 SURVEY FOR R E PERVIS DB 151 PG 319 S C R

Flood risk

High riskFEMA Zone AE, XPanel 12117C0260F

FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From SR 417 exit West on Aloma, right on Tuscawilla Rd, Left on Old Bear Run.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 22, 2026 at 1:17 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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