Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.
Property Details
Price:
$3,495,000
MLS #:
O6450869
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
GREEN OAKS REP
Neighborhood:
32789winterpark
Listed Date:
Oct 19, 2026
Finished Sq Ft:
4,483
Total Sq Ft:
6,182
Lot Size:
13,787 sqft / 0.32 acres (approx)
Year Built:
2008
See this Listing
Schools
Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Slate, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Smart Thermostat, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
Laundry Features
Common Area, Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Attached Garage YN
1
Common Walls
Corner Unit
Community Features
Park, Playground, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
East
Exterior Features
Balcony, French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Smart Lock(s)
Fencing
Fenced, Masonry
Garage Spaces
3
Lot Features
Corner Lot, City Lot, Landscaped, Level, Oversized Lot, Sidewalk
Open Parking YN
1
Other Structures
Cabana
Parking Features
Curb Parking, Driveway, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized
Patio And Porch Features
Covered, Front Porch, Patio, Rear Porch, Side Porch
Roof
Shingle
Security Features
Fire Alarm, Security System, Smoke Detector(s)
View
Garden
Window Features
Blinds, Double Pane Windows, Drapes, Tinted Windows, Window Treatments
Financial
Tax Year
2025
Taxes
$20,740
Map
Community
- Address1600 LEGION DRIVE WINTER PARK FL
- SubdivisionGREEN OAKS REP
- 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 Oct 23, 2026
271
Single Family Listed
87
Avg DOM
485
Avg $ / SqFt
$1,390,881
Avg List Price
Property Summary
- Located in the GREEN OAKS REP subdivision, 1600 LEGION DRIVE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $3,495,000 and features 5 beds, 6 baths, and has approximately 4,483 square feet of living space, and was originally constructed in 2008. The current price per square foot is $780. 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 $1,390,881. To schedule a showing of MLS#o6450869 at 1600 LEGION DRIVE in WINTER PARK, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of COLDWELL BANKER 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 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. 1600 LEGION DRIVE
WINTER PARK, FL
