1600 LEGION DRIVE Winter Park, FL $ 3,995,000
1600 LEGION DRIVE
$ 3,995,000
Recently Listed
Open House 6/21 2pm - 4pm
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1600 LEGION DRIVE

Winter Park, FL, 32789
$ 3,995,000
Bedrooms5 Baths5.1 Sq 4,483

Monthly Estimate*

$ 24,598

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Single Family Home for sale in Winter Park, FL

for $3,995,000 with 5 bedrooms and 5 full baths, 1 half bath. This 4,483 square foot home was built in 2008 on a lot size of 0.32.

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.

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Open House

6/21/2026 2:00 PM - 4:00 PM
1600 LEGION DRIVE Winter Park, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 3,995,000

Bedrooms

5

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 20,740

Style

Traditional

Lot Size

0.32

Year Built

2008

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6415591

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Connected Electricity Connected Natural Gas Connected Phone Available Propane Public Sewer Connected Sprinkler Meter Street Lights Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Disposal Dryer Gas Water Heater Microwave Range Range Hood Refrigerator Tankless Water Heater Washer Wine Refrigerator
Zoning R-1AA
Garage Spaces 3
Patio/Porch Features Covered Deck Front Porch Patio Side Porch
Architectural Style Traditional
Pool Features Deck Gunite Heated In Ground Lap Lighting Outside Bath Access Salt Water
Security Features Security System Smoke Detector(s)
Construction Materials Block Stucco
Year Built 2008
View Garden Pool
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Park Playground Sidewalks
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name GREEN OAKS REP
Facing Direction West
Garage Y/N true
Other Structures Cabana
Total Rooms 12
Full Baths 5
Status Active
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.
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 13787
Carport Y/N false
Listing Terms Cash Conventional
Elementary School Dommerich Elem
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 20740
Home Warranty Y/N false
Middle/Junior High School Maitland Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://apex-imaging-media-1.aryeo.com/videos/019ebf03-e62a-716d-ab2b-89a89ecb4b68
Building Area Units Square Feet
Living Area Units Square Feet
Builder Name Keith D. Field
Standard Status Active
Occupancy Type Owner
Tax Lot A
Legal Description REPLAT OF GREEN OAKS Q/30 THE S 91.7 FTOF W 150 FT LOT A
Minimum Lease No Minimum
Water Access Y/N false
Additional Rooms Attic Breakfast Room Separate Den/Library/Office Family Room Formal Dining Room Separate Inside Utility Storage Rooms
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Carpet Slate Hardwood
Furnished Y/N Negotiable
Fireplace Features Family Room Gas Other Room Outside Wood Burning
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Display Window(s) Double Pane Windows Drapes Shades Shutters Wood Frames
Fireplace Y/N true
Half Baths 1
Laundry Features Common Area Inside Laundry Room
Total Bedrooms 5
Total Baths 6
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Exterior
Exterior Amenities Balcony French Doors Garden Irrigation System Lighting Outdoor Grill Private Mailbox Private Yard Rain Gutters Sidewalk
Vegetation Trees/Landscaped
Fencing Fenced
Parking Features Curb Parking Driveway Electric Vehicle Charging Station(s) Garage Door Opener Garage Faces Rear On Street Oversized
Lot Features Corner Lot City Lot Landscaped Level Oversized Lot Sidewalk
Water Source Public
Lot Size Area 13787
Foundation Details Slab
Spa false
Building Area Total 6182
Lot Dimensions 150 x 91.7
Lot Size Acres 0.32
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Paved
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Coldwell Banker Realty

Broker

brian@brianteach.com

Email

Affordability Calculator

$26,326
Per Month
93%
7%
0%
Monthly Principal & Interest
$24,598
Monthly Property Taxes
$1,728
Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
6/13/2026$3,995,000 Listed Price

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1600 LEGION DRIVE, Winter Park, FL, 32789 is a Single Family Home for sale at $3,995,000 with 4,483 sqft and a lot size of 0.32. 1600 LEGION DRIVE has 5 bedrooms, 5.1 baths, and was built in 2008. The property's zip code is 32789 which is in Winter Park, FL