A high motivation price improvement! Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside, enjoy the elegance of solid hardwood and modern tile flooring, high ceilings, and two wood burning fireplaces. The chef’s kitchen is equipped with premium appliances, including SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor boasts a secluded primary suite, a guest bedroom suite, and a study/library with closet and built-ins. Upstairs, find two additional bedrooms and a full bath. Modern amenities include zoned A/C, a new EV charger and epoxy flooring in the 2-car garage. Conveniently located near parks and the Winter Park Racquet Club, this home offers easy access to downtown Winter Park’s shops, dining, and cultural venues, making it ideal for families and active lifestyles. This property also offers deeded lake access to the Winter Park Chain of Lakes by becoming a member of the Maitland Shores Lakefront Preservation Association for an annual fee. The access is very convenient and offers a private ramp to store and launch kayaks, canoes, etc. This location offers effortless access to schools, green parks, fitness centers/trails, cultural venues—an ideal blend of amenities, charm and location for any homebuyer.
Property Details
Price:
$2,200,000
MLS #:
O6355858
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
MAITLAND SHORES
Neighborhood:
32789winterpark
Listed Date:
Nov 4, 2025
Finished Sq Ft:
3,986
Total Sq Ft:
5,353
Lot Size:
17,640 sqft / 0.40 acres (approx)
Year Built:
1953
See this Listing
Schools
Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Porcelain Tile, Tile, Hardwood
Heating
Central
Interior Features
High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Mid-Century Modern, Traditional
Attached Garage YN
1
Community Features
Park, Playground, Sidewalks, Tennis Court(s)
Construction Materials
Block
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Awning(s), Garden, Irrigation System, Private Mailbox, Sidewalk
Fencing
Other, Wood
Garage Spaces
2
Lot Features
Landscaped, Oversized Lot, Private, Sidewalk
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
Patio And Porch Features
Covered, Front Porch, Patio
Roof
Shingle
View
Garden, Pool
Financial
Tax Year
2025
Taxes
$26,035
Map
Community
- Address2299 VIA TUSCANY WINTER PARK FL
- SubdivisionMAITLAND SHORES
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- —
- 147 INTERLACHEN PLACE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA BUS CENTER
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ART SYSTEMS CENTER
- AUTUMN GLEN
- BANKS COLONIAL ESTATES
- 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 4TH ADD
- CAMPO BELLO
- CAMWOOD SUB
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CEDAR RIDGE UNIT 1
- CEDAR RIDGE UNIT 2
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CLOISTER GROVE REP
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- 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 13
- EASTBROOK SUB UNIT 14
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- EDGEWOOD SUB
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 5TH ADD
- FERNBROOK TRAILS
- FERNBROOK TRAILS PH 3
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- GALLERY AT WINTER PARK SEC 01
- GALLOWAY PLACE REP
- GARDEN GROVE
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE SUB
- GLENMOOR
- GOLDEN ROD MANOR
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE GOLF COURSE SEC 01
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENVIEW AT WINTER PINES
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 06
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 10
- HILLS
- HOWELL ESTATES 1ST ADD
- HOWELL ESTATES REP
- HUNTINGTON COURT
- HYDE PARK
- J KRONENBERGER SUB
- KAROLINA ON KILLARNEY
- KENILWORTH ESTATES
- KENILWORTH SHORES
- 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 SHORES
- LACHEN HOUSE CONDO
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- 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
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- LYNN HAVEN
- MACCALLUM SUB
- MAGNOLIA GARDENS SUB
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MORSELAND SUB
- NORTHWOOD TERRACE
- OAKCREST-516
- OAKS CONDO
- OLYMPIA HEIGHTS
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR STRATFORD SEC
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA COURT
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 1
- OSCEOLA SUMMIT
- PALMER AVE LAKESIDE PROP
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK HILL
- PARK MANOR
- PARK NORTH
- PARK SHORE
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PELICAN BAY
- PENNSYLVANIA STATION 01 CONDO
- PERLE DU LAC
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINEWOOD SUB
- PRESERVE AT HAWKS CREST
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- ROBERT DHU MACDONALD PARK
- SANCTUARY AT ALOMA
- SANDLEWOOD CREEK CONDO PH 10
- SEVILLA
- SEVILLE PARK
- SHORES LAKE KILLARNEY
- SLOVAK VILLAGE
- SORENSEN HEIGHTS
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANGLEWOOD SEC 4
- TEMPLE ESTATES
- TEMPLE HEIGHTS
- TEMPLE TERRACE ANNEX
- TERAZZO DEL SOL CONDO ASSN INC
- THOMAS M HENKELS ADD
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TRINITY BAY PH 2
- TROVILLION CONDO
- TUSCANIA
- TUSCANY TERRACE
- TWIN ACRES
- URBAN GREEN 12
- VALENCIA TERRACE
- VILASA TWNHMS
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VILLAS OF CASSELBERRY PH 4
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD 3
- WHISPERWOOD CONDO
- WILLA GROVE
- WINDSONG ELIZABETHS WALK
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 2
- WINDWARD SQUARE SEC 3
- WINTER GREEN
- WINTER PARK
- WINTER PARK COMMERCE CENTER
- WINTER PARK ESTATES
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK OAKS
- 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 04
- WOODCREST UNIT 01
- WRENWOOD CONDO
Market Summary
Current real estate data for Single Family in WINTER PARK as of Apr 23, 2026
274
Single Family Listed
86
Avg DOM
491
Avg $ / SqFt
$1,484,233
Avg List Price
Property Summary
- Located in the MAITLAND SHORES subdivision, 2299 VIA TUSCANY WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $2,200,000 and features 4 beds, 4 baths, and has approximately 3,986 square feet of living space, and was originally constructed in 1953. The current price per square foot is $552. The average price per square foot for Single Family listings in WINTER PARK is $491. The average listing price for Single Family in WINTER PARK is $1,484,233. To schedule a showing of MLS#o6355858 at 2299 VIA TUSCANY in WINTER PARK, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
Similar Listings Nearby
Courtesy of CORCORAN PREMIER 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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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. 2299 VIA TUSCANY
WINTER PARK, FL





