1600 LEGION DRIVE WINTER PARK FL 32789 MLS #O6415591

1600 LEGION DRIVE
WINTER PARK, FL, 32789
$3,995,000
5 Beds
5.5 Baths
4,483 SqFt
0.32 Acres
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MLS #O6415591 image #0
Open House Jun 21, 2026
02:00 – 04:00
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:
$3,995,000
MLS #:
O6415591
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
GREEN OAKS REP
Neighborhood:
32789winterpark
Listed Date:
Jun 15, 2026
Finished Sq Ft:
4,483
Total Sq Ft:
6,182
Lot Size:
13,787 sqft / 0.32 acres (approx)
Year Built:
2008
TraditionalPoolPrimary Bedroom Main Floor32789 – Winter Park32789winterparkGreen Oaks RepDommerich ElemMaitland MiddleWinter Park HighIt Is The Responsibility Of The Buyer’s Agent And Buyer To Verify With The City Of Winter Park Regarding Any Leasing Or Rental Restrictions Applicable To This Property.No Minimum

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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, 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
Community Features
Park, Playground, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
West
Exterior Features
Balcony, French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
Fencing
Fenced
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, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized
Patio And Porch Features
Covered, Deck, Front Porch, Patio, Side Porch
Roof
Shingle
Security Features
Security System, Smoke Detector(s)
View
Garden, Pool
Window Features
Blinds, Display Window(s), Double Pane Windows, Drapes, Shades, Shutters, Wood Frames

Financial

Tax Year
2025
Taxes
$20,740

Map

Community

Subdivisions in WINTER PARK

Market Summary

Current real estate data for Single Family in WINTER PARK as of Jun 15, 2026
320
Single Family Listed
85
Avg DOM
472
Avg $ / SqFt
$1,385,554
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 $3,995,000 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 $891. The average price per square foot for Single Family listings in WINTER PARK is $472. The average listing price for Single Family in WINTER PARK is $1,385,554. To schedule a showing of MLS#o6415591 at 1600 LEGION DRIVE in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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