1600 Legion Drive, FL
Stellar MLS

$3,995,000

1600 Legion Drive

Winter Park, FL 32789

Listing updated: June 15, 2026 at 10:40 AM ET

Active
5
Beds
6
Baths
4,483
Sq Ft
0.32
Acres
2008
Built
Private poolFireplace3-car garage$891/sqft
Single Family Residence

Property type

2008

Year built

13,787 sqft

Lot size

$891

Price / sq ft

No HOA

HOA dues

0

Days on market

3

Garage spaces

X

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$20,201
Property taxes$1,728
Home insurance (est.)$1,831

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Jun 15, 2026
  2. Listed$3,995,000
    Jun 15, 2026
  3. Price increased$3,995,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
0
Subdivision
Green Oaks Rep
County
Orange
Year built
2008
Living area
4,483 sq ft
Price/sq ft
$891
Building area
6,182 sq ft (Public Records)
Lot size
13,787 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X (12095C0255F)
Garage
3 spaces
Pool
Private pool
Annual taxes
$20,740 (2025)
Parcel #
31-21-30-3172-00-102
Zoning
R-1AA
MLS #
O6415591

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Interior Details

Bedrooms
5
Full bathrooms
5
Half bathrooms
1
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
Stories / Levels
Two
Direction faces
West
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric
Cooling
Central Air

Parking

Garage spaces
3
Attached garage
Yes
Parking features
Curb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
It 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.

Exterior & Construction

Exterior features
Balcony, French Doors, Garden, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Meter, Water Connected

Schools

ElementaryADommerich ElemGreatSchools ↗
MiddleBMaitland MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
OfficeFirst15.7x13
Dining RoomFirst15.7x13
KitchenFirst19.3x20.5
DinetteFirst13.8x11
Great RoomFirst21.1x19.5
Primary BedroomFirst19.5x15.1
Primary BathroomFirst16x13
Bedroom 2First15.9x16
Bedroom 3Second15x14
Bedroom 4Second15x14
Bedroom 5Second14.5x13
Balcony/Porch/LanaiFirst20.7x12

Listing Details

Listing date
2026-06-13
On market date
2026-06-15
Original list price
$3,995,000
Occupant type
Owner
MLS area
32789 - Winter Park
Listing AOR
Orlando Regional
Status changed
2026-06-15
Tax legal description
REPLAT OF GREEN OAKS Q/30 THE S 91.7 FTOF W 150 FT LOT A

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From N. Park Avenue, head NORTH on Summerland Avenue. Continue as the road curves LEFT, transforming into Dixie Parkway. RIGHT on Legion Drive. The home is located immediately on your RIGHT, 1600 Legion Drive.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 15, 2026 at 10:40 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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