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$1,850,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,288 Sq. Ft.
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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.

Full Property Details for 4469 Old Bear Run

General

  • Price: $1,850,000
  • Taxes: $10,710 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6375415
  • Updated: 4/2/2026
  • Added to Site: 98 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 8
  • 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)
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile, Porcelain Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosure, Tile
  • Security/Safety: Security Gate, Security System, Security System Owned, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors, Storage
  • Deck/Patio: Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Seminole
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: PERVIS SURVEY FOR R E
  • Driving Directions: From SR 417 exit West on Aloma, right on Tuscawilla Rd, Left on Old Bear Run.
  • Direction Faces: East

School Information

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

Community

  • Community Name: 32792 - Winter Park/Aloma

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Central, Electric, Zoned

Utilities

  • Sewer: Septic Tank
  • Water District: BEAR GULLY
  • Water: Canal/Lake For Irrigation, Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Street Lights, Water Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Stucco, Wood Frame (FSC Certified)
  • Roof: Shingle
  • Windows: Blinds, Double Pane Windows, Tinted Windows
  • Stories/Levels: One
  • Square Feet: 4,288
  • Sq. Ft. Source: Public Records
  • Year Built: 1978

Additional Structures

  • Other Structures: Outdoor Kitchen, Shed(s), Storage

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.74
  • Lot Size (Sq. Ft.): 32,200
  • Lot Size: 32200
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced, Other

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: BEAR GULLY
  • Water Front Desc.: Lake Front

Financial Considerations

  • Tax Amount: $10,710
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 5 SURVEY FOR R E PERVIS DB 151 PG 319 S C R
  • Flood Zone Info: AE, X
  • APN: 36213050100000050
  • Property ID: 36213050100000050
  • Block/Lot/Section: 1000

Listed by Lpt Realty, Llc

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Listing agent

— 4469 Old Bear Run —

  • Lpt Realty, Llc

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NMLS#: 1598647

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NMLS#: 1598647

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Schools serving 4469 Old Bear Run

School District:Seminole County School District
NameGradesDistance
Red Bug Elementary School
4000 Red Bug Lake Road, Casselberry, FL 32707
K-52 mi
Tuskawilla Middle School
1801 Tuskawilla Road, Oviedo, FL 32765
6-80.8 mi
Lake Howell High School
4200 Dike Road, Winter Park, FL 32792
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4469 Old Bear Run Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/02/2026
Price Reduced
$1,850,000
-5.13%
MLS
2/09/2026
Listed
$1,950,000
158.62%
MLS
7/22/2015
Sold
$754,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 4469 Old Bear Run

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,430
7%
$851,743
3%
2024
$10,710
2%
$827,739
3%
2023
$10,469
3%
$803,630
6%
2021
$10,145
-1%
$757,498
-3%
2022
$10,227
1%
$780,223
4%
2021
$10,145
2%
$747,039
4%
2018
$9,929
—
$716,627
2%
2017
$9,897
-1%
$701,887
-4%
2019
$9,997
-7%
$730,243
5%
2016
$10,806
4%
$698,240
6%
2015
$10,437
14%
$660,589
8%
2014
$9,168
-5%
$613,839
-2%
2013
$9,635
—
$625,805
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Lpt Realty, Llc

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4469 Old Bear Run, Winter Park, FL 32792 (MLS# O6375415) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 4469 Old Bear Run is currently listed for $1,850,000 and was received on February 09, 2026. Want to learn more about 4469 Old Bear Run? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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