← Back to homesACTIVE · MLS MFRO6415591

Winter Park, FL · Single Family Residence

1600 Legion Dr

$3,795,000
MLS MFRO6415591
5Bedrooms
6Bathrooms
4,483Square feet
0.32Acres

THE SETTING, AND THE DETAILS

A closer look.

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.

Private poolGarage

The details that help you decide.

Details supplied with the listing. Information that was not provided is marked below.

Home essentials
Price per square foot
$847
Full bathrooms
5
Half bathrooms
1
Heated living area
4483
Lot size (acres)
0.32
Lot size (sq ft)
13787
Year built
2008
Property type
Residential
Property style
Traditional
Interior & rooms
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
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Flooring
Carpet, Slate, Wood
Additional rooms
Attic,Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Inside Utility,Storage Rooms
Land, water & community
Waterfront
No
Waterfront type
Not provided
Water body / lake name
Not provided
Water view
Not provided
Dock
Not provided
Dock features
Not provided
Other views
Garden, Pool
Lot features
Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Exterior features
Balcony, French Doors, Garden, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
Community amenities
Park, Playground, Sidewalks, Street Lights
Zoning
R-1AA
Current use
Not provided
Horse amenities
Not provided
Fencing
Fenced
Other structures
Cabana
Pool, parking & systems
Private pool
Yes
Pool features
Deck, Gunite, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water
Garage
Yes
Garage spaces
3
Carport
No
Carport spaces
Not provided
Parking features
Curb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized
Fireplace
Yes
Fireplace features
Family Room, Gas, Other, Outside, Wood Burning
Heating
Central, Electric
Cooling
Central Air
Water supply
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
Construction
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Stories
2
Levels
Two
Location & schools
City
WINTER PARK
Subdivision
GREEN OAKS REP
County
Orange
ZIP code
32789
Elementary school
Dommerich Elem
Middle school
Maitland Middle
High school
Winter Park High
Association, taxes & listing
HOA / association
No
Association fee
Not provided
Fee frequency
Not provided
Included services
Not provided
Association amenities
Not provided
Additional association fee
Not provided
Additional fee frequency
Not provided
Condo fee
Not provided
Condo fee frequency
Not provided
Annual property taxes
$20,740
Tax year
2025
Other annual assessments
Not provided
CDD
No
Listing status
Active
Days on market
34
Listing broker
COLDWELL BANKER REALTY
MLS number
MFRO6415591

Explore the area

Location supplied with the listing. Confirm boundaries and access for the property.

Listed by COLDWELL BANKER REALTY · MLS MFRO6415591
Source: mfrmls · Listing updated 2026-07-19 20:05:29 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.

Listing photograph

MLS MFRO6415591 · COLDWELL BANKER REALTY

A GOOD CONVERSATION IS A GOOD START

Let’s talk about
your next move.

Ask about this home, arrange a showing, or talk through what you’re looking for.

Call Scott: (407) 760-0382

Your inquiry goes directly to Scott.

Enter the answer as a number. Or call Scott if you prefer.

By submitting, you ask Scott to respond to this inquiry. Privacy Policy