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For saleErrorPrice cut: $50K (5/22)
$1,799,999
5beds
4,288sqft

4469 OLD BEAR RUN, WINTER PARK, FL 32792

5beds
4,288sqft
Single family residence
Built in 1978
0.74 Acres
2 Attached garage spaces
$420 price/sqft

What's special

Fully fenced yardPrivate gated lakefront livingContemporary backsplashQuartz countertopsAbundant custom storage throughoutNew pool deck paversRussound sound system

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 ...

169 days
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1,162
|
46
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Source: Stellar MLS,MLS#: O6375415MLS LogoOriginating MLS: Orlando Regional
Travel times

Living Room

Kitchen

Primary Bedroom

Primary Bathroom

Screened Patio /Pool

Outdoor 1

Zillow last checked:

Listing updated:

Listed by:

Keigan Lewis 305-393-8683,

LPT REALTY, LLC 877-366-2213

Source: Stellar MLS,MLS#: O6375415MLS LogoOriginating MLS: Orlando Regional

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 5
  • Bathrooms: 5
  • Full bathrooms: 4
  • 1/2 bathrooms: 1
Rooms
  • Room types: Attic, Great Room, Utility Room
Primary bedroom
  • Features: En Suite Bathroom, Walk-In Closet(s)
  • Level: First
  • Area: 380 Square Feet
  • Dimensions: 20x19
Bedroom 2
  • Features: En Suite Bathroom, Walk-In Closet(s)
  • Level: First
  • Area: 342 Square Feet
  • Dimensions: 19x18
Bedroom 3
  • Features: En Suite Bathroom, Walk-In Closet(s)
  • Level: First
  • Area: 380 Square Feet
  • Dimensions: 20x19
Bedroom 4
  • Features: Jack & Jill Bathroom, Built-in Closet
  • Level: First
  • Area: 180 Square Feet
  • Dimensions: 12x15
Bedroom 5
  • Features: Jack & Jill Bathroom, Built-in Closet
  • Level: First
  • Area: 110 Square Feet
  • Dimensions: 10x11
Great room
  • Features: Ceiling Fan(s), No Closet
  • Level: First
  • Area: 1054 Square Feet
  • Dimensions: 31x34
Gym
  • Features: Ceiling Fan(s), No Closet
  • Level: First
  • Area: 228 Square Feet
  • Dimensions: 12x19
Kitchen
  • Features: Breakfast Bar, No Closet
  • Level: First
  • Area: 270 Square Feet
  • Dimensions: 15x18
Heating
  • Central, Electric, Zoned
Cooling
  • Central Air, Zoned
Appliances
  • Included: Bar Fridge, Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Laundry: Inside, Laundry Room
Features
  • Ceiling Fan(s), Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Flooring: Carpet, Ceramic Tile, Porcelain Tile
  • Doors: Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors
  • Windows: Skylight(s)
  • Has fireplace: No
Interior area
  • Total structure area: 5,731
  • Total interior livable area: 4,288 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 2
  • Parking features: Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
  • Attached garage spaces: 2
  • Has uncovered spaces: Yes
Features
  • Levels: One
  • Stories: 1
  • Patio & porch: Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
  • Exterior features: Irrigation System, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Storage
  • Has private pool: Yes
  • Pool features: Auto Cleaner, Deck, Gunite, In Ground, Lighting, Salt Water, Screen Enclosure, Tile
  • Fencing: Fenced,Other
  • Has view: Yes
  • View description: Water, Lake
  • Has water view: Yes
  • Water view: Water,Lake
  • Waterfront features: Lake Front, Lake Privileges, Lift - Covered, Skiing Allowed
  • Body of water: BEAR GULLY
Lot
  • Size: 0.74 Acres
  • Features: In County, Landscaped, Oversized Lot
  • Residential vegetation: Mature Landscaping
Details
  • Additional structures: Outdoor Kitchen, Shed(s), Storage
  • Parcel number: 36213050100000050
  • Zoning: R-1AA
  • Special conditions: None

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Florida
  • Property subtype: Single Family Residence
Materials
  • Stucco, Wood Frame (FSC Certified)
  • Foundation: Slab
  • Roof: Shingle
Condition
  • New construction: No
  • Year built: 1978

Utilities & green energy

  • Sewer: Septic Tank
  • Water: Canal/Lake For Irrigation, Public
  • Utilities for property: BB/HS Internet Available, Electricity Connected, Street Lights, Water Connected

Community & HOA

Community
  • Security: Security Gate, Security System, Security System Owned, Smoke Detector(s)
  • Pet fee: $0 monthly
  • Subdivision: PERVIS SURVEY FOR R E
HOA
  • Has HOA: No
Location
  • Region: Winter Park

Financial & listing details

  • Price per square foot: $420/sqft
  • Tax assessed value: $1,495,643
  • Annual tax amount: $10,710
  • Date on market: 2/9/2026
  • Cumulative days on market: 163 days
  • Listing terms: Cash,Conventional
  • Ownership: Fee Simple
  • Total actual rent: 0
  • Electric utility on property: Yes
  • Road surface type: Paved

Price history

DateEventPrice
7/20/2026Listed for sale$1,799,999$420/sqft
Source: Stellar MLS #O6375415 Report a problem
7/14/2026Contingent$1,799,999$420/sqft
Source: Stellar MLS #O6375415 Report a problem
5/22/2026Price change$1,799,999-2.7%$420/sqft
Source: Stellar MLS #O6375415 Report a problem
4/2/2026Price change$1,850,000-5.1%$431/sqft
Source: Stellar MLS #O6375415 Report a problem
2/9/2026Listed for sale$1,950,000+2.7%$455/sqft
Source: Stellar MLS #O6375415 Report a problem
7/29/2025Listing removed$1,899,000$443/sqft
Source: Stellar MLS #O6294027 Report a problem
6/10/2025Price change$1,899,000-4.9%$443/sqft
Source: Stellar MLS #O6294027 Report a problem
5/19/2025Price change$1,996,000-5%$465/sqft
Source: Stellar MLS #O6294027 Report a problem
4/23/2025Price change$2,100,000-4.5%$490/sqft
Source: Stellar MLS #O6294027 Report a problem
3/27/2025Listed for sale$2,200,000+191.8%$513/sqft
Source: Stellar MLS #O6294027 Report a problem
7/28/2015Sold$754,000-9%$176/sqft
Source: Public Record Report a problem
7/6/2015Listed for sale$829,000$193/sqft
Source: AMERITEAM REALTY, INC. #O5339833 Report a problem
7/6/2015Pending sale$829,000$193/sqft
Source: AMERITEAM REALTY, INC. #O5339833 Report a problem
7/2/2015Listed for sale$829,000$193/sqft
Source: AMERITEAM REALTY, INC. #O5339833 Report a problem
5/24/2015Pending sale$829,000$193/sqft
Source: AMERITEAM REALTY, INC. #O5339833 Report a problem
1/19/2015Listed for sale$829,000$193/sqft
Source: AmeriTeam Realty, Inc. #O5339833 Report a problem
11/27/2014Listing removed$829,000$193/sqft
Source: AmeriTeam Realty, Inc. #O5332463 Report a problem
11/25/2014Listed for sale$829,000+18.4%$193/sqft
Source: AmeriTeam Realty, Inc. #O5332463 Report a problem
7/28/2014Sold$700,000-4.1%$163/sqft
Source: Public Record Report a problem
5/24/2014Pending sale$730,000$170/sqft
Source: AmeriTeam Realty, Inc. #O5221892 Report a problem
5/24/2014Listed for sale$730,000+29.2%$170/sqft
Source: AmeriTeam Realty, Inc. #O5221892 Report a problem
8/5/2004Sold$565,000+109.3%$132/sqft
Source: Public Record Report a problem
10/13/1997Sold$270,000$63/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$11,733 +12.8%$851,743 +2.9%
2024$10,405 +2.4%$827,739 +3%
2023$10,164 +2.4%$803,630 +3%
2022$9,927 -2.1%$780,223 +3%
2021$10,145 +0.6%$757,498 +1.4%
2020$10,082 +0.8%$747,039 +2.3%
2019$9,997 $730,243 +1.9%
2018$9,997 +0.7%$716,627 +2.1%
2017$9,929 +0.3%$701,887 -1.3%
2016$9,897 -8.4%$711,454 +7.7%
2015$10,806 $660,589 +7.6%
2014$10,806 +14.7%$613,839 -1.9%
2013$9,425 -8.1%$625,805 -11.2%
2012$10,256 +0.5%$704,968 +1.6%
2011$10,203 -4.5%$694,191 -3.3%
2010$10,688 -8.4%$718,246 -8.4%
2009$11,666 -11.2%$784,280 -13.8%
2008$13,144 +3.6%$910,274 +3%
2007$12,683 +2.2%$883,761 +11.2%
2006$12,405 +70.1%$794,757 +78.6%
2005$7,291 +63.1%$444,938 +53.7%
2004$4,471 +0.6%$289,554 +1.9%
2003$4,443 +1%$284,155 +2.4%
2002$4,400 +3.6%$277,495 +4.6%
2000$4,246 $265,170

Find assessor info on the county website

Monthly payment

Est. payment
$11,434/mo
Principal & interest
$9214
Property taxes
$2220
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Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 32792

Nearby schools

Red Bug Elementary School
Grades PK-5 • 2 miles
6/10
GreatSchools® Rating
Test Score Rating
7/10
Student Progress Rating
4/10
Tuskawilla Middle School
Grades 6-8 • 0.7 miles
8/10
GreatSchools® Rating
Test Score Rating
7/10
Student Progress Rating
8/10
Lake Howell High School
Grades 9-12 • 1.1 miles
7/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
8/10
Student Progress Rating
6/10

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