Under contract-accepting backup offers. Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.
Property Details
Price:
$3,100,000
MLS #:
O6345511
Status:
Pending
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTER PARK
Neighborhood:
32789winterpark
Listed Date:
Sep 26, 2025
Finished Sq Ft:
3,896
Total Sq Ft:
3,896
Lot Size:
18,001 sqft / 0.41 acres (approx)
Year Built:
1920
See this Listing
Schools
Elementary School:
Audubon Park K8
Middle School:
Audubon Park K-8
High School:
Winter Park High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Carpet, Tile, Hardwood
Heating
Central, Zoned
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Construction Materials
Vinyl Siding, Wood Frame
Direction Faces
South
Exterior Features
Irrigation System, Rain Gutters, Sidewalk
Lot Features
Corner Lot, City Lot, Landscaped, Level, Oversized Lot, Sidewalk
Open Parking YN
1
Other Structures
Guest House
Parking Features
Circular Driveway, Driveway, Parking Pad
Patio And Porch Features
Covered, Patio, Rear Porch, Wrap Around
Roof
Shingle
Window Features
Insulated Windows, Shades
Financial
Tax Year
2024
Taxes
$3,876
Map
Community
- Address457 E NEW ENGLAND AVENUE WINTER PARK FL
- SubdivisionWINTER PARK
- 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 Single Family in WINTER PARK as of May 05, 2026
290
Single Family Listed
82
Avg DOM
485
Avg $ / SqFt
$1,453,800
Avg List Price
Property Summary
- Located in the WINTER PARK subdivision, 457 E NEW ENGLAND AVENUE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $3,100,000 and features 5 beds, 5 baths, and has approximately 3,896 square feet of living space, and was originally constructed in 1920. The current price per square foot is $796. 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 $1,453,800. To schedule a showing of MLS#o6345511 at 457 E NEW ENGLAND 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. 457 E NEW ENGLAND AVENUE
WINTER PARK, FL

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