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.
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.
Property Details
Price:
$1,950,000
MLS #:
O6375415
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
PERVIS SURVEY FOR R E
Neighborhood:
32792winterparkaloma
Listed Date:
Feb 9, 2026
Finished Sq Ft:
4,288
Total Sq Ft:
5,731
Lot Size:
32,200 sqft / 0.74 acres (approx)
Year Built:
1978
See this Listing
Schools
Elementary School:
Red Bug Elementary
Middle School:
Tuskawilla Middle
High School:
Lake Howell High
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Carpet, Ceramic Tile, Porcelain Tile
Heating
Central, Electric, Zoned
Laundry Features
Inside, Laundry Room
Exterior
Architectural Style
Florida
Construction Materials
Stucco, Wood Frame (FSC Certified)
Exterior Features
Irrigation System, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors, Storage
Other Structures
Outdoor Kitchen, Shed(s), Storage
Parking Features
Circular Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side
Roof
Shingle
Security Features
Security Gate, Security System, Security System Owned, Smoke Detector(s)
Financial
Tax Year
2024
Taxes
$10,710
Map
Community
- Address4469 OLD BEAR RUN WINTER PARK FL
- SubdivisionPERVIS SURVEY FOR R E
- CityWINTER PARK
- CountySeminole
- Zip Code32792
Subdivisions in WINTER PARK
- 3223171-3223171
- 4572 PALMETTO CONDO
- ACREAGE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ARBORS/ARAGON
- ARROWHEAD COVE
- ARROWHEAD COVE UNIT 02
- ART SYSTEMS CENTER
- AUTUMN GLEN
- AUTUMN GLEN PH 2
- AZALEA LANE
- BANKS COLONIAL ESTATES
- BEAR GULLY BAY
- BEAR GULLY FOREST
- BEAR GULLY POINTE
- BEL AIRE PINES
- BEL-AIRE PINES, UNIT TWO
- BRIDGEWATER
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 3RD ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- BROOKSHIRE HEIGHTS 4TH ADDITION
- BUNGALOW PARK
- CAMPO BELLO
- CAMWOOD SUB
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE UNIT 3
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLLEGE PLACE REP
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORINTHEAN/WINTER PARK CONDO
- CORONADO TWNHMS
- CORONATION ADD
- CORTLAND PARK
- COUNTRY LANE
- CROSSROADS BUS CNTR CONDP
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 07
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTBROOK SUBD UNIT NO 14
- EASTGATE SUB
- EDEN POINT
- ELLNO WILLO
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 5TH ADD
- FAIRBANKS SHORES FIRST ADD
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS PH 3
- FLAMINGO SHORES
- FLORA PARK FIRST ADD
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS
- FOUR SEASONS CONDO
- GALLERY AT WINTER PARK SEC 02
- GALLOWAY PLACE REP
- GARDEN ACRES 2ND REP OF BLK E
- GARDEN ACRES REP
- GARDEN LAKE ESTATES UNIT 1
- GEORGEANN HOMES
- GLENCOE SUB
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENS/PK
- GREENVIEW AT WINTER PINES
- HAMILTON PLACE
- HARBOUR RIDGE
- HAWK’S CREST
- HAWKS CREST
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 04
- HIDDEN OAKS CONDO PH 05
- HIDDEN OAKS CONDO PH 07
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 10
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL ESTATES 2ND ADD
- HOWELL ESTATES REP
- HUNTINGTON CONDO
- HYDE PARK
- J KRONENBERGER SUB
- JENKINS ADD
- JENKINS SECOND ADD
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KENILWORTH SHORES SEC 1
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KINGS COVE
- KNOWLES MANOR NORTH CONDO
- LACHEN HOUSE CONDO
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE MONTE SUB
- LAKE SPIER CROSSING
- LAKE VIRGINIA CONDO
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- LAKEMONT HEIGHTS
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LANDMARK WINTER PARK CONDO
- LAUREL SPGS
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LORING CHASE
- LOST CREEK
- LOT 59 HYDE PARK PB 34 PGS 38 TO 40
- LUGANO TERRACE
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MC INTYRE PLACE CONDO
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- MORSELAND SUB
- NORTHWOOD TERRACE
- OAKS CONDO
- OLYMPIA HEIGHTS
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 03
- OSCEOLA SUMMIT
- PALMER AVE LAKESIDE PROP
- PALMER PARK
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK HILL
- PARK SHORE
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO BLDG 2929
- PELICAN BAY
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD
- PRESERVE AT HAWKS CREST
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- RIDGE HIGH 1ST ADD
- SANCTUARY AT ALOMA
- SANCTUARY AT LAKE ANN
- SANDALWOOD CREEK CONDO PH 09
- SANDALWOOD CREEK CONDO PH 11
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO
- SELLS TERRACE
- SEMINOLE COUNTY
- SEMORAN MEDICAL-SURGICAL CENTER CONDO
- SEVILLA
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TAMARAK
- TANGERINE COURT
- TANGLEWOOD SEC 2
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TAX EQUITIES INC REP
- TEMPLE ESTATES
- TEMPLE HEIGHTS
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- THE COLONIES CONDO
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUSCANIA
- TUSCANY PLACE FIRST ADD
- TUSCANY TERRACE
- URBAN GREEN 12
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 1
- VILLAGE WINTERSET INC
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS CONDO
- VIRGINIA HEIGHTS REP
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERWOOD CONDO
- WILLA GROVE
- WINDSONG
- WINDSONG LAKESIDE
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDWARD SQUARE SEC 1
- WINTER PARK
- WINTER PARK COMMERCE CENTER
- WINTER PARK ESTATES
- WINTER PARK FOREST 1ST ADD
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK MANOR
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES REP
- WINTER PARK PINES VILLAS
- WINTER PARK RESIDENTIAL
- WINTER PARK VILLAGE
- WINTER PARK VILLAS CONDO
- WINTER PARK VILLAS CONDO BLDG 12
- WINTER PARK WOODS CONDO
- WINTERBROOK
- WOODCREST CONDO
- WOODCREST UNIT 04
- WOODCREST UNIT5
- WRENWOOD CONDO
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 2ND ADD
Market Summary
Current real estate data for Single Family in WINTER PARK as of Mar 12, 2026
235
Single Family Listed
98
Avg DOM
485
Avg $ / SqFt
$1,484,798
Avg List Price
Property Summary
- Located in the PERVIS SURVEY FOR R E subdivision, 4469 OLD BEAR RUN WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32792. It is listed for $1,950,000 and features 5 beds, 5 baths, and has approximately 4,288 square feet of living space, and was originally constructed in 1978. The current price per square foot is $455. The average price per square foot for Single Family listings in WINTER PARK is $485. The average listing price for Single Family in WINTER PARK is $1,484,798. To schedule a showing of MLS#o6375415 at 4469 OLD BEAR RUN in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of LPT REALTY, LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 4469 OLD BEAR RUN
WINTER PARK, FL












































































