A rare opportunity to build your custom dream home on a cleared homesite spanning more than one-half acre in a prime Winter Park location. Large, buildable parcels of this size are becoming increasingly difficult to find, making this an exceptional offering for those seeking space, flexibility and freedom to create a custom residence. Along Pennsylvania Avenue, this expansive homesite is ready for construction, with no HOA, allowing you to bring your builder and vision to life (Building: 35% FAR approximately 7,800 square feet + excluded porches square feet, all calculations to be confirmed with your architect and City of WP Building Dept). The generous dimensions easily accommodate a substantial residence with room for a resort-style pool, expansive outdoor living areas, guest house or other amenities, creating endless possibilities. Enjoy an exceptional lifestyle just minutes from many of Winter Park’s most popular destinations. Go to, bike or take a golf cart ride to the historic Winter Park 9 Golf Course, the boutiques, award-winning restaurants and sidewalk cafés of Park Avenue, the vibrant dining scene of Hannibal Square, Winter Park Village, Mead Botanical Garden and numerous parks, cultural attractions and community events. This central location also offers convenient access to Rollins College, Valencia College, highly regarded public and private schools, downtown Orlando, major hospitals, Orlando Executive Airport, Orlando International Airport and Central Florida’s major roadways. Whether your vision is a timeless estate, a contemporary architectural masterpiece or a private retreat with exceptional outdoor living, this oversized homesite provides the rare canvas to bring it to life. Opportunities to purchase a cleared, build-ready parcel of more than one-half acre in Winter Park are few and far between, making this an outstanding opportunity to create a one-of-a-kind residence in one of Central Florida’s established communities.
Property Details
Price:
$1,295,000
MLS #:
O6429124
Status:
Active
Beds:
0
Baths:
0
Type:
Land
Subdivision:
WINTER PARK OASIS
Neighborhood:
32789winterpark
Listed Date:
Sep 2, 2026
Lot Size:
22,198 sqft / 0.51 acres (approx)
See this Listing
Schools
Elementary School:
Lakemont Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Exterior
Direction Faces
East
Fencing
Masonry
Lot Features
Buildable, Cleared, Corner Lot, Curb and Gutters, City Lot, Level, Oversized Lot, Room For Pool, Sidewalk
Financial
Tax Year
2025
Taxes
$5,407
Map
Community
- Address1021 N PENNSYLVANIA AVENUE WINTER PARK FL
- SubdivisionWINTER PARK OASIS
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- 3223171-3223171
- 4572 PALMETTO CONDO
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ARROWHEAD COVE
- ART SYSTEMS CENTER
- AUTUMN GLEN PH 2
- BANKS COLONIAL ESTATES
- BEAR GULLY POINTE
- BEL AIRE PINES
- BEL-AIRE PINES, UNIT TWO
- BRIDGEWATER
- BRIDGEWATER PH 2
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 3RD ADD
- BROOKSHIRE HEIGHTS 4TH ADDITION
- BUNGALOW PARK
- CAMPO BELLO
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE UNIT 1
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CHEROKEE PARK
- CLOISTER GROVE REP
- 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
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 06 REP OF PT OF BLK 14
- EASTBROOK SUB UNIT 07
- EASTBROOK SUB UNIT 13
- 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
- FAIRBANKS SHORES THIRD ADD
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS PH 3
- 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 GROVE
- GARDEN LAKE ESTATES UNIT 1
- GEORGEANN HOMES
- GEORGETOWN ESTATES UT 1
- GLENCOE SUB
- GOLDENROD VILLAS CONDO
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENS/PK
- GREENVIEW AT WINTER PINES
- HAMILTON PLACE
- HARBOUR RIDGE
- HAWK’S 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 10
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL BRANCH WOODS
- HOWELL ESTATES 1ST ADD
- HOWELL ESTATES REP
- HUNTINGTON CONDO
- 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 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- 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
- 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 GARDENS SUB
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MC INTYRE PLACE CONDO
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MINNESOTA CONDO
- MORSELAND SUB
- NORTHWOOD TERRACE
- 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 GROVE
- PARK HILL
- PARK SHORE
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PARKVIEW VILLAGE CONDO BLDG 2929
- PELICAN BAY
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD
- PRESERVE AT HAWKS CREST
- RIDGE HIGH 1ST ADD
- SANCTUARY AT LAKE ANN
- SANDALWOOD CREEK CONDO PH 09
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO
- SELLS TERRACE
- SEVILLA
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- SPRINGVIEW
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TAMARAK
- TANGERINE COURT
- TANGLEWOOD SEC 2
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TAX EQUITIES INC REP
- TEMPLE HEIGHTS
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- THE COLONIES CONDO
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUCKS KNOLL
- TUSCANIA
- TUSCANY TERRACE
- URBAN GREEN 12
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 1
- VILASA TWNHMS
- VILLAGE WINTERSET INC
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS CONDO
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WEST WINTER PT
- WHISPERING WATERS
- WHISPERWOOD CONDO
- WHISPERWOOD CONDO 04
- WILLA GROVE
- WINDSONG ELIZABETHS WALK
- WINDSONG LOOKOUT LANDING 43/79
- WINDSONG PRESERVE POINT 43/76
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 3
- 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 OASIS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK PINES VILLAS
- WINTER PARK RESIDENTIAL
- WINTER PARK VILLAGE
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 03
- WINTERBROOK
- WOODCREST UNIT 01
- WOODCREST UNIT5
- WOODMERE TERRACE REP
- WRENWOOD CONDO
- WRENWOOD HEIGHTS UNIT 2
Market Summary
Current real estate data for Land in WINTER PARK as of Sep 05, 2026
24
Land Listed
104
Avg DOM
$1,576,787
Avg List Price
Property Summary
- Located in the WINTER PARK OASIS subdivision, 1021 N PENNSYLVANIA AVENUE WINTER PARK FL is a Land for sale in WINTER PARK, FL, 32789. It is listed for $1,295,000 and features 1 acres. To schedule a showing of MLS#o6429124 at 1021 N PENNSYLVANIA AVENUE in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of PREMIER SOTHEBY’S INTL. REALTY. 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. 1021 N PENNSYLVANIA AVENUE
WINTER PARK, FL

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