$3,995,000
Active

1600 LEGION DRIVE

WINTER PARK, FL 32789 — GREEN OAKS REP
5 Beds
6 Baths
4,483 sqft
0.32 acres
Built 2008
3-Car Garage

About This Property

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

Basics

Property Type
Residential
Property Subtype
Single Family Residence
MLS Number
O6415591
Year Built
2008
Levels
Two
Architectural Style
Traditional
Additional Rooms
Attic,Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Inside Utility,Storage Rooms
Direction Faces
West
Occupant Type
Owner

Size & Structure

Living Area
4,483 sqft
Total Area
6,182 sqft
Lot Size
0.32 acres
Lot Sq Ft
13,787 sqft
Bedrooms
5
Full Baths
5
Half Baths
1
Garage Spaces
3
Stories
2

Interior

Flooring
Carpet, Slate, Wood
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Interior Features
Built-in Features, Ceiling Fans(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eat-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
Common Area, Inside, Laundry Room
Windows
Blinds, Display Window(s), Double Pane Windows, Drapes, Shades, Shutters, Wood Frames
Fireplace
Yes — Family Room, Gas, Other, Outside, Wood Burning
Furnished
Negotiable
A/C
Central Air
Heating
Central, Electric

Exterior & Lot

Exterior Features
Balcony, French Doors, Garden, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
Construction
Block, Stucco
Roof
Shingle
Foundation
Slab
Patio/Porch
Covered, Deck, Front Porch, Patio, Side Porch
Other Structures
Cabana
Fencing
Fenced
Lot Features
Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
View
Garden, Pool

Water & Pool

Pool
Yes — Deck, Gunite, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water

Community & HOA

HOA
No
Community Features
Park, Playground, Sidewalks, Street Lights
Homestead
Yes
Security
Secured Garage/Parking, Security System, Smoke Detector(s)

Utilities & Systems

Water
Public
Sewer
Public Sewer
Utilities
BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Meter, Water Connected
Cooling
Central Air
Heating
Central, Electric
Flood Zone
X
Parking
Curb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized

Financial

List Price
$3,995,000
Annual Taxes
$20,740
Tax Year
2025
Listing Terms
Cash, Conventional
Special Conditions
None
Possession
Close Of Escrow

Schools

Elementary
Dommerich Elem
Middle School
Maitland Middle
High School
Winter Park High

Virtual Tour

View Virtual Tour

Location