Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated
community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137-
acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is
surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the
moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings,
expansive windows and sliding glass doors that draw your attention to the pool and picturesque
backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the
beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble
countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall
ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking
the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor-
to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering
space. A secondary bedroom and full bathroom are conveniently located just off the family
room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant
windows and a French door providing direct access to the pool and lanai. Completely remodeled
in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious
shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond
the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room,
two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower.
Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly
together. The heated pool and spa are surrounded by a covered, screened lanai and a lush
backyard oasis complete with mature trees and charming walking paths—creating a private
setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a
brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter
Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool
resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in
2013.
community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137-
acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is
surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the
moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings,
expansive windows and sliding glass doors that draw your attention to the pool and picturesque
backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the
beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble
countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall
ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking
the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor-
to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering
space. A secondary bedroom and full bathroom are conveniently located just off the family
room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant
windows and a French door providing direct access to the pool and lanai. Completely remodeled
in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious
shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond
the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room,
two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower.
Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly
together. The heated pool and spa are surrounded by a covered, screened lanai and a lush
backyard oasis complete with mature trees and charming walking paths—creating a private
setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a
brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter
Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool
resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in
2013.
Property Details
Price:
$1,395,000
MLS #:
O6438691
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BEAR GULLY POINTE
Neighborhood:
32792winterparkaloma
Listed Date:
Sep 8, 2026
Finished Sq Ft:
4,247
Total Sq Ft:
5,575
Lot Size:
25,595 sqft / 0.59 acres (approx)
Year Built:
1993
See this Listing
Schools
Elementary School:
Eastbrook Elementary
Middle School:
Tuskawilla Middle
High School:
Lake Howell High
Interior
Appliances
Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Gas Water Heater, Microwave, Refrigerator
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Carpet, Marble, Porcelain Tile, Hardwood
Heating
Central, Electric, Zoned
Interior Features
Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Custom
Association Amenities
Gated, Playground
Attached Garage YN
1
Community Features
Dock, Lake, Waterfront, Deed Restrictions, Gated Community – No Guard, Playground, Sidewalks, Tennis Court(s)
Construction Materials
Stucco, Wood Frame
Covered Spaces
3
Direction Faces
West
Exterior Features
French Doors, Irrigation System, Sidewalk, Sliding Doors
Garage Spaces
3
Lot Features
In County, Landscaped, Oversized Lot, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Garage Faces Side, Oversized
Patio And Porch Features
Covered, Rear Porch, Screened
Roof
Built-Up, Shingle
Security Features
Gated Community, Security System Owned, Smoke Detector(s)
Spa Features
Heated, In Ground
Waterfront Features
Lake, Waterfront
Window Features
Drapes, Shutters
Financial
HOA Fee
$500
HOA Fee Frequency
Quarterly
HOA Includes
Recreational Facilities
HOA Name
Michael Leqve
HOA Phone
(407) 876-9599
Tax Year
2025
Taxes
$11,148
Map
Community
- Address2873 OLD CASTLE DRIVE WINTER PARK FL
- SubdivisionBEAR GULLY POINTE
- CityWINTER PARK
- CountySeminole
- Zip Code32792
Subdivisions in WINTER PARK
- 147 INTERLACHEN PLACE
- 3223171-3223171
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA BUS CENTER
- ALOMA PARK
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ART SYSTEMS CENTER
- AUTUMN GLEN
- AUTUMN GLEN PH 3
- BEAR GULLY FOREST
- BEL-AIRE PINES, UNIT TWO
- BLDG 6 UNIT 189 THE STRATFORD A WINTER PARK CONDOM
- BLK C PT REP 02
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- CAMPO BELLO
- CAMWOOD SUB
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CASA ALOMA
- CEDAR RIDGE UNIT 2
- CEDARWOOD VILLAGE 1
- CHANTILLY SUB
- CHARMONT
- CHATEAUX DU LAC
- CINNAMON SHORES
- CLOISTER GROVE REP
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORONADO TWNHMS
- CORONATION ADD
- COUNTRY LANE
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 14
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 16
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- EDGEWOOD SUB
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- ETHEL PARK
- FAIRBANKS PARK
- FERNBROOK TRAILS
- FERNBROOK TRAILS PH 3
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- GALLOWAY PLACE REP
- GARDEN GROVE
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE SUB
- GOLDEN ROD MANOR
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE GOLF COURSE SEC 01
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENVIEW AT WINTER PINES
- H VANWIES SUB
- HENKEL ADD
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 06
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL ESTATES 1ST ADD
- HOWELL HEIGHTS
- HUNTINGTON COURT
- HYDE PARK
- J KRONENBERGER SUB
- KAROLINA ON KILLARNEY
- KENILWORTH ESTATES
- KENILWORTH SHORES
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KENILWORTH SHORES SECTION FOUR Y/71 LOT 21 BLK B
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KILLARNEY SHORES
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE MONTE SUB
- LAKE SPIER XING
- LAKE VIRGINIA
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- LAKEMONT HEIGHTS
- LAKESIDE ESTATES
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LAS CASAS DE INDIANA
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- LYNN HAVEN
- MAGNOLIA GARDENS SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MERRIE OAKS VILLAGE PH 01
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- NORTHWOOD TERRACE
- OAKS CONDO
- OLYMPIA HEIGHTS
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA COURT
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 1
- OSCEOLA SUMMIT
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK MANOR
- PARK NORTH
- PARKLANDO
- PARKLANDO #3
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PELICAN BAY
- PENNSYLVANIA STATION 01 CONDO
- PERLE DU LAC
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD SUB
- PRESERVE AT HAWKS CREST
- QUARTERS AT WINTER PARK CONDO
- ROBERT DHU MACDONALD PARK
- SANCTUARY AT ALOMA
- SANDALWOOD CREEK CONDO PH 01
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO PH 10
- SEVILLA
- SEVILLE PARK
- SICILIAN SHORES
- SLOVAK VILLAGE
- SORENSEN HEIGHTS
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- STRATFORD WINTER PARK
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- SYLVAN PARK
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANGLEWOOD SEC 4
- TEMPLE HEIGHTS
- TEMPLE TERRACE ANNEX
- TERAZZO DEL SOL CONDO ASSN INC
- THOMAS M HENKELS ADD
- TIMBERLANE SHORES
- TRINITY BAY PH 2
- TUSCANIA
- TUSCANY TERRACE
- TWIN ACRES
- URBAN GREEN 12
- VALENCIA TERRACE
- VILASA TWNHMS
- VILLAGE/WHISPERWOOD
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD CONDO
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 2
- WINTER GREEN
- WINTER PARK
- WINTER PARK ESTATES
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK REP BLK 75
- WINTER PARK VILLAGE
- WINTER PARK VILLAS BLDG 14
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 01
- WINTER WOODS UNIT 03
- WINTER WOODS UNIT 04
- WOODCREST UNIT 01
- WRENWOOD CONDO
Market Summary
Current real estate data for Single Family in WINTER PARK as of Sep 10, 2026
287
Single Family Listed
91
Avg DOM
475
Avg $ / SqFt
$1,288,941
Avg List Price
Property Summary
- Located in the BEAR GULLY POINTE subdivision, 2873 OLD CASTLE DRIVE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32792. It is listed for $1,395,000 and features 4 beds, 4 baths, and has approximately 4,247 square feet of living space, and was originally constructed in 1993. The current price per square foot is $328. The average price per square foot for Single Family listings in WINTER PARK is $475. The average listing price for Single Family in WINTER PARK is $1,288,941. To schedule a showing of MLS#o6438691 at 2873 OLD CASTLE DRIVE in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of FANNIE HILLMAN & ASSOCIATES. 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. 2873 OLD CASTLE DRIVE
WINTER PARK, FL
