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
- ALABAMA CONDO
- ALBERT LEE RIDGE
- ALBERT LEE RIDGE 1ST ADD
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALEXANDER PLACE
- ALOMA
- ALOMA PARK
- ALOMA TRAILS
- ARROWHEAD COVE
- ART SYSTEMS CENTER
- AUTUMN GLEN PH 3
- BANKS COLONIAL ESTATES
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 2ND ADD
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE
- CEDARWOOD VILLAGE
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CLOISTER GROVE SUB
- COLLEGE PLACE REP
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORONATION ADD
- COUNTRY LANE
- DUBSDREAD HEIGHTS
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 07
- EASTBROOK SUB UNIT 11
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 16
- EASTBROOK SUB UNIT 8
- EASTBROOK SUBD UNIT NO 05
- EASTGATE SUB
- EDGEWOOD SUB
- ELIZABETH HEIGHTS SUB
- ELLNO WILLO
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 5TH ADD
- FAIRSHORES PLACE
- FAIRVIEW HEIGHTS REP
- FLAMINGO SHORES
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- FREMAR
- GARDEN ACRES
- GARDEN GROVE
- GARDEN LAKE ESTATES UNIT 1
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE
- GLENCOE SUB
- GLENCOE SUBDIVISION
- GLENMOOR
- GOLFSIDE SEC 2
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GRAND PINES
- GRAYSON SQUARE
- GREEN TERRACE V/140 LOT 3 BLK B
- GREENVIEW AT WINTER PINES
- H VANWIES SUB
- HAMILTON PLACE
- HARBOUR RIDGE
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 10
- HIDDEN OAKS CONDO PH 11
- HIDDEN OAKS CONDO PH 12
- HIDDEN OAKS CONDO PH 7
- HILLS
- HORTON AARON
- HOWELL BRANCH WOODS
- HOWELL ESTATES 1ST ADD
- HYDE PARK
- J KRONENBERGER SUB
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KAWILLA CREST
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 05
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KILLARNEY POINT
- KINGS COVE
- KNOWLES MANOR NORTH CONDO
- LAKE ANN ESTATES UNIT 2
- LAKE ANN ESTATES UNIT 3
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY CONDOMINIUM ASSN INC.
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE 2ND ADD
- LAKE KNOWLES TERRACE ADD 02
- LAKE MAITLAND
- LAKE MONTE SUB
- LAKE SYLVAN SHORES
- LAKE VIRGINIA
- LAKE WAUNATTA WODS
- LAKE WAUNATTA WOODS
- LAKESIDE ESTATES
- 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
- LOST CREEK
- LOT 4 LESS N 80 FT OF E 102.66 FT BLK B SLOVAK V
- LUGANO TERRACE
- MACK PETER REV
- MAGNOLIA GARDENS SUB
- MAITLAND SHORES 1ST ADD
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MONDRIAN/WINTER PARK TWNHMS
- MORSE & PENNSYLVANIA TWNHMS
- MORSELAND SUB
- NEW ENGLAND BLDG
- NORTH GOLDENROD COMMERCE PARK
- NORTHWOOD TERRACE
- OAKCREST-516
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA HEIGHTS
- OSCEOLA OR LAKEVIEW DEED
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 02
- OSCEOLA SHORES SEC 03
- PARK GROVE
- PARK HILL
- PARK MANOR FIRST ADD
- PARK NORTH
- PARK POINTE REP
- PARK WEST CONDO
- PARKLANDO
- PARKLANDO #3
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PENNSYLVANIA PLACE REP
- PERLE DU LAC
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINES
- PRESERVE AT HAWKS CREST
- QUARTERS AT WINTER PARK CONDO
- RIDGE HIGH 1ST ADD
- ROBERT DHU MACDONALD PARK
- SEVILLE PARK
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES
- SLOVAK VILLAGE
- SOUTH INTERLACHEN PLACE
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- STRATFORD WINTER PARK
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- SYLVAN PARK
- TALMAN MEWS PH 2
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TEMPLE ESTATES
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- TEMPLE TRAIL VILLAGE
- TERRAZO DEL SOL
- THE ENCLAVE WINTER PARK
- TIMBERLANE SHORES
- TOWN OF WINTER PARK
- TRINITY BAY
- TRINITY BAY PH 2
- TROTTERS REP
- TUSCANY TERRACE
- TWIN ACRES
- UNIVERSITY GARDEN
- UNRECORDED PLAT
- URBAN GREEN 12
- VIA LAGO/HANGING MOSS CONDO
- VIA LAGO/HANGING MOSS PH 09
- VIA LAGO/HANGING MOSS PH 3
- VILASA TWNHMS
- VILLA VIEW PARK
- VILLAGE GREEN
- VILLAGE WINTERSET INC
- VILLAS OF ARAGON CONDO
- VILLAS OF CASSELBERRY PH 3
- VILLAS OF CASSELBERRY PH 4
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VIRGINIA HGTS REP
- VISTAS AT LAKE HOWELL
- WATERBRIDGE
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE AT WINTER PARK CONDOMINIUM D107
- WATERFALL COVE OF WINTER PARK
- WATERFALL COVE/WINTER PARK
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD CONDO
- WHISPERWOOD CONDO 02
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 2
- WINDWARD SQUARE SEC 3
- WINFLOR COURT PT REP
- WINTER PARK
- WINTER PARK COMM
- WINTER PARK ESTATES
- WINTER PARK GARDENS CONDO
- WINTER PARK OASIS
- WINTER PARK PINES
- WINTER PARK PINES CONDO
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK RESIDENTIAL
- WINTER PARK REV
- WINTER PARK VILLAGE
- WINTER PARK VILLAS
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 01
- WINTER WOODS UNIT 04
- WOODCREST UNIT 03
- WOODCREST UNIT 5
- WOODCREST UNIT 6
- WOODMERE TERRACE REP
- WRENWOOD CONDO
- WRENWOOD HEIGHTS
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 2ND ADD
- WRENWOOD UNIT 3 3RD ADD
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 800-783-8847.
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
