Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue.
This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, flowing seamlessly into a sun-drenched sunroom destined to become a favorite retreat. Chicago brick flooring, fixed glass windows, and accordion doors frame serene views of the private backyard oasis.
The gourmet kitchen is both stunning and functional, featuring custom soft-close cabinetry, quartz countertops, floating shelving, exquisite millwork, and a full suite of Thermador appliances. A generous 4.9-by-10-foot island with storage on both sides anchors the space, complemented by a cozy breakfast nook and built-in bar. French doors provide effortless indoor-outdoor connection. Just beyond, a thoughtfully designed mudroom and pool bath with Chicago brick flooring offers convenient access to the pool area. A spacious first-floor bedroom—ideal as a guest suite, office, or den—along with a full bath completes the main level.
Upstairs, the luxurious primary suite offers a private sanctuary with dual walk-in closets and a spa-inspired bath featuring separate vanities, soaking tub, steam shower, and private water closet. Two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas for comfort and privacy. The expansive laundry room adds charm and practicality with a retro sink, built-in ironing board, and abundant storage.
The tranquil backyard is designed for quintessential Florida living, showcasing a beautifully resurfaced pool surrounded by lush landscaping—perfect for entertaining or quiet relaxation.
Additional highlights include engineered hardwood flooring throughout, designer lighting, a wrought-iron staircase, new baseboards and crown molding, fresh interior and exterior paint, newer roof (2023), two HVAC systems (2022 & 2023), and an oversized two-car garage with dedicated workshop space. Located within highly regarded A-rated schools.
This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, flowing seamlessly into a sun-drenched sunroom destined to become a favorite retreat. Chicago brick flooring, fixed glass windows, and accordion doors frame serene views of the private backyard oasis.
The gourmet kitchen is both stunning and functional, featuring custom soft-close cabinetry, quartz countertops, floating shelving, exquisite millwork, and a full suite of Thermador appliances. A generous 4.9-by-10-foot island with storage on both sides anchors the space, complemented by a cozy breakfast nook and built-in bar. French doors provide effortless indoor-outdoor connection. Just beyond, a thoughtfully designed mudroom and pool bath with Chicago brick flooring offers convenient access to the pool area. A spacious first-floor bedroom—ideal as a guest suite, office, or den—along with a full bath completes the main level.
Upstairs, the luxurious primary suite offers a private sanctuary with dual walk-in closets and a spa-inspired bath featuring separate vanities, soaking tub, steam shower, and private water closet. Two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas for comfort and privacy. The expansive laundry room adds charm and practicality with a retro sink, built-in ironing board, and abundant storage.
The tranquil backyard is designed for quintessential Florida living, showcasing a beautifully resurfaced pool surrounded by lush landscaping—perfect for entertaining or quiet relaxation.
Additional highlights include engineered hardwood flooring throughout, designer lighting, a wrought-iron staircase, new baseboards and crown molding, fresh interior and exterior paint, newer roof (2023), two HVAC systems (2022 & 2023), and an oversized two-car garage with dedicated workshop space. Located within highly regarded A-rated schools.
Property Details
Price:
$2,200,000
MLS #:
O6386867
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CINNAMON SHORES
Neighborhood:
32789winterpark
Listed Date:
Mar 6, 2026
Finished Sq Ft:
3,472
Total Sq Ft:
4,432
Lot Size:
12,960 sqft / 0.30 acres (approx)
Year Built:
1990
See this Listing
Schools
Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Brick/Stone, Engineered Hardwood, Porcelain Tile
Heating
Central, Propane, Zoned
Laundry Features
Laundry Room, Upper Level
Exterior
Construction Materials
Brick, HardiPlank Type
Exterior Features
French Doors, Irrigation System
Parking Features
Driveway, Garage Door Opener, Oversized
Roof
Built-Up
Security Features
Smoke Detector(s)
Financial
Tax Year
2026
Taxes
$18,918
Map
Community
- Address2423 VIA SIENNA WINTER PARK FL
- SubdivisionCINNAMON SHORES
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- 3223171-3223171
- 4572 PALMETTO CONDO
- ACREAGE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ARBORS/ARAGON
- ARROWHEAD COVE
- ARROWHEAD COVE UNIT 02
- ART SYSTEMS CENTER
- AUTUMN GLEN
- AUTUMN GLEN PH 2
- AZALEA LANE
- BANKS COLONIAL ESTATES
- BEAR GULLY BAY
- BEAR GULLY FOREST
- BEAR GULLY POINTE
- BEL AIRE PINES
- BEL-AIRE PINES, UNIT TWO
- BRIDGEWATER
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 3RD ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- BROOKSHIRE HEIGHTS 4TH ADDITION
- BUNGALOW PARK
- CAMPO BELLO
- CAMWOOD SUB
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CARVER TOWN FIRST ADD
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE UNIT 3
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- 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
- CROSSROADS BUS CNTR CONDP
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 07
- 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
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS PH 3
- FLAMINGO SHORES
- 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 LAKE ESTATES UNIT 1
- GEORGEANN HOMES
- GLENCOE SUB
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENS/PK
- GREENVIEW AT WINTER PINES
- HAMILTON PLACE
- HARBOUR RIDGE
- HAWK’S CREST
- HAWKS 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 09
- HIDDEN OAKS CONDO PH 10
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL ESTATES 2ND ADD
- HOWELL ESTATES REP
- HUNTINGTON CONDO
- HYDE PARK
- 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 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KENILWORTH SHORES SEC 1
- 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 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 SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MC INTYRE PLACE CONDO
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- MORSELAND SUB
- NORTHWOOD TERRACE
- OAKS CONDO
- 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 GREEN
- PARK GROVE
- PARK HILL
- PARK SHORE
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO BLDG 2929
- PELICAN BAY
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD
- PRESERVE AT HAWKS CREST
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- RIDGE HIGH 1ST ADD
- SANCTUARY AT ALOMA
- SANCTUARY AT LAKE ANN
- SANDALWOOD CREEK CONDO PH 09
- SANDALWOOD CREEK CONDO PH 11
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO
- SELLS TERRACE
- SEMINOLE COUNTY
- SEMORAN MEDICAL-SURGICAL CENTER CONDO
- SEVILLA
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TAMARAK
- TANGERINE COURT
- TANGLEWOOD SEC 2
- TANGLEWOOD SEC 3 REP
- TANTUM ADD
- TAX EQUITIES INC REP
- TEMPLE ESTATES
- TEMPLE HEIGHTS
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- THE COLONIES CONDO
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUSCANIA
- TUSCANY PLACE FIRST ADD
- TUSCANY TERRACE
- URBAN GREEN 12
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 1
- VILLAGE WINTERSET INC
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS CONDO
- VIRGINIA HEIGHTS REP
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERWOOD CONDO
- WILLA GROVE
- WINDSONG
- WINDSONG LAKESIDE
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDWARD SQUARE SEC 1
- 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 PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES REP
- WINTER PARK PINES VILLAS
- WINTER PARK RESIDENTIAL
- WINTER PARK VILLAGE
- WINTER PARK VILLAS CONDO
- WINTER PARK VILLAS CONDO BLDG 12
- WINTER PARK WOODS CONDO
- WINTERBROOK
- WOODCREST CONDO
- WOODCREST UNIT 04
- WOODCREST UNIT5
- WRENWOOD CONDO
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 2ND ADD
Market Summary
Current real estate data for Single Family in WINTER PARK as of Mar 13, 2026
241
Single Family Listed
94
Avg DOM
486
Avg $ / SqFt
$1,493,621
Avg List Price
Property Summary
- Located in the CINNAMON SHORES subdivision, 2423 VIA SIENNA 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 3,472 square feet of living space, and was originally constructed in 1990. The current price per square foot is $634. The average price per square foot for Single Family listings in WINTER PARK is $486. The average listing price for Single Family in WINTER PARK is $1,493,621. To schedule a showing of MLS#o6386867 at 2423 VIA SIENNA 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. 2423 VIA SIENNA
WINTER PARK, FL











































