Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park’s unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.
Property Details
Price:
$750,000
MLS #:
O6442587
Status:
Active
Beds:
3
Baths:
1
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LAKE KNOWLES TERRACE
Neighborhood:
32789winterpark
Listed Date:
Sep 18, 2026
Finished Sq Ft:
1,325
Total Sq Ft:
1,980
Lot Size:
7,441 sqft / 0.17 acres (approx)
Year Built:
1952
See this Listing
Schools
Interior
Appliances
Range
Bathrooms
1 Full Bathroom
Cooling
Central Air
Flooring
Hardwood
Heating
Electric
Interior Features
Ceiling Fan(s)
Laundry Features
Other
Levels
One
Exterior
Architectural Style
Traditional
Construction Materials
Brick
Covered Spaces
1
Direction Faces
South
Exterior Features
Sidewalk
Garage Spaces
1
Roof
Shingle
Financial
Tax Year
2025
Taxes
$1,882
Map
Community
- Address1421 CHESTNUT AVENUE WINTER PARK FL
- SubdivisionLAKE KNOWLES TERRACE
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- ACREAGE & UNREC
- ALBERT LEE RIDGE
- ALBERT LEE RIDGE 1ST ADD
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE ANNEX
- ALBERT LEE RIDGE FIRST ADD
- ALEXANDER PLACE
- ALOMA
- ALOMA PARK
- ALOMA TRAILS
- ARROWHEAD COVE
- ART SYSTEMS CENTER
- ATTILIO G PANACCIONES SUB
- AUTUMN GLEN PH 3
- BANKS COLONIAL ESTATES
- BEAR GULLY BAY
- BEAR GULLY POINTE
- BROOKSHIRE HEIGHTS
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE
- CEDARWOOD VILLAGE
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CHEROKEE PARK
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLLEGE PLACE REP
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CONWILL ESTS
- CORONATION ADD
- COUNTRY LANE
- CRANES CREEK
- CRANES CRK
- DETMAR TERRACE WINTER PARK
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 8
- EASTBROOK SUBD UNIT NO 05
- EASTGATE SUB
- EDGEWOOD SUB
- ELIZABETH HEIGHTS SUB
- ELLNO WILLO
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRSHORES PLACE
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS
- FLAMINGO SHORES
- FONTAINEBLEAU
- FOREST HILLS
- FORREST HILLS
- FREMAR
- GARDEN LAKE ESTATES UNIT 1
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE
- GLENCOE SUB
- GLENCOE SUBDIVISION
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GRAND PINES
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN TERRACE V/140 LOT 3 BLK B
- GREENVIEW AT WINTER PINES
- H VANWIES SUB
- HAMILTON PLACE
- HARBOR EAST
- HENKEL ADD
- HENKELS ADD/WINTER PARK
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- 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 REP
- J KRONENBERGER SUB
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- 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 SPIER XING
- LAKE SYLVAN SHORES
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WODS
- LAKE WAUNATTA WOODS
- LAKESIDE ESTATES
- LAKESIDE MANOR APTS CONDO
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LANDMARK WINTER PARK CONDO
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- MACK PETER REV
- MAGNOLIA GARDENS SUB
- MAITLAND SHORES 1ST ADD
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEAD GARDEN CONDOMINIUM
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MORSE & PENNSYLVANIA TWNHMS
- MORSELAND SUB
- MRS L A DENNIS SUB
- NEW ENGLAND BLDG
- NORTH GOLDENROD COMMERCE PARK
- NORTHWOOD TERRACE
- OAKCREST-516
- OLYMPIA HEIGHTS
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA SHORES SEC 02
- OSCEOLA SHORES SEC 03
- PALMER AVE LAKESIDE PROP
- PARK GROVE
- PARK MANOR FIRST ADD
- PARK POINTE REP
- PARK WEST CONDO
- PARKLANDO
- PARKLANDO #3
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PARKVIEW VILLAGE CONDO BLVD 2918
- PERLE DU LAC
- PHILLIPS CIRCLE REP
- PINES
- PRESERVE AT HAWKS CREST
- QUARTERS AT WINTER PARK CONDO
- RIDGE HIGH 1ST ADD
- RIDGE HIGH SUB
- SANDLEWOOD CREEK PHASE 2
- SEVILLE PARK
- SHARON PLACE
- SHERBROOKE
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES
- SLOVAK VILLAGE
- SOUTH INTERLACHEN PLACE
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- SYLVAN PARK
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TEMPLE ESTATES
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- TERRAZO DEL SOL
- THE ENCLAVE WINTER PARK
- TIMBERLANE SHORES
- TOWN OF WINTER PARK
- TOWNHOMES/HARPER PLACE
- TRINITY BAY
- TRINITY BAY PH 2
- TROTTERS REP
- TUSCANY TERRACE
- TWIN ACRES
- URBAN GREEN 12
- VERSAILLES WINTER PARK CONDO
- VIA LAGO/HANGING MOSS CONDO
- VIA LAGO/HANGING MOSS PH 09
- VILASA TWNHMS
- VILLA VIEW PARK
- VILLAGE CONDOS
- VILLAGE GREEN
- VILLAGE WINTERSET INC
- VILLAS OF ARAGON CONDO
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 3
- VILLAS OF CASSELBERRY PH 4
- 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
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD CONDO
- WHISPERWOOD CONDO 02
- WINDSONG ELIZABETHS WALK 43/81
- 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 HEIGHTS
- WINTER PARK OAKS
- WINTER PARK OASIS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES REP
- WINTER PARK PINES UNIT 4
- 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 03
- WINTER WOODS UNIT 04
- WOODCREST UNIT 5
- WOODMERE TERRACE REP
- WRENWOOD CONDO
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 3RD ADD
Market Summary
Current real estate data for Single Family in WINTER PARK as of Sep 18, 2026
308
Single Family Listed
87
Avg DOM
487
Avg $ / SqFt
$1,331,784
Avg List Price
Property Summary
- Located in the LAKE KNOWLES TERRACE subdivision, 1421 CHESTNUT AVENUE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $750,000 and features 3 beds, 1 baths, and has approximately 1,325 square feet of living space, and was originally constructed in 1952. The current price per square foot is $566. The average price per square foot for Single Family listings in WINTER PARK is $487. The average listing price for Single Family in WINTER PARK is $1,331,784. To schedule a showing of MLS#o6442587 at 1421 CHESTNUT AVENUE in WINTER PARK, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of CHARLES RUTENBERG REALTY ORLANDO. 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 WINDERMERE INTERNATIONAL REALTY include the name of the listing broker. Neither the listing company nor WINDERMERE INTERNATIONAL REALTY 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. 1421 CHESTNUT AVENUE
WINTER PARK, FL
