1600 Legion Dr | Image 1
New
Open House
1600 Legion Dr | Image 2
1600 Legion Dr | Image 3
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1600 Legion Dr | Image 7

$3,995,000

For Sale

2 days ago

1600 Legion Dr, Winter Park, FL

House

MLS® O6415591

5 Bed

6 Bath

4483 sqft

3 Parking

Open House
Sun Jun 21, 2:00-4:00 PM EDT
  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 4483 sqft
Garage Yes
Taxes $20,740
Days Active 2
Lot Size 0.32 Acres
Approx. Age 2008
Avg. Price Per Sqft $891
MLS® Number O6415591

Property Address: 1600 Legion Dr, Winter Park, FL, 32789-1433

Average square foot calculated using Size range provided by listing agent.

Description

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.
MLS® NumberO6415591
Laundry LevelEnsuite
Central VacNo
FireplaceYes
Acreage
Exterior
GarageYes
Approx. Age2008
Basement
DrivewayCurb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized
Garage Spaces
HeatCentral, Electric
A/CCentral Air

Extras

Rooms

Kitchen:First Floor19.3 × 20.5 ft
Bedroom 5:Second Floor14.5 × 13 ft
Other:First Floor20.7 × 12 ft
Great Room:First Floor21.1 × 19.5 ft
Other:First Floor13.8 × 11 ft
Bedroom 2:First Floor15.9 × 16 ft
Office:First Floor15.7 × 13 ft
Dining Room:First Floor15.7 × 13 ft
Bedroom 4:Second Floor15 × 14 ft
Bedroom 3:Second Floor15 × 14 ft
Other:First Floor19.5 × 15.1 ft
Other:First Floor16 × 13 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Jun 13, 2026List Date
$3,995,000List Price

Home Appraisal

This property is estimated to sell between: $3,655,000 and $4,165,000.
Similar properties in this area sold on average for: $3,655,000
Expected to sell in 62 days. Similar properties sold in 64 days. This home has been on eXp Realty for 2 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

  • Commute

Commute

Starting Address
Destination Address
1600 Legion Dr, Winter Park, FL

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