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$3,995,000
1 Day On Site

1600 LEGION DRIVE
WINTER PARK, FL 32789

Single Family Residence|Coming Soon
5
Beds
6
Total Baths
5
Full Baths
1
Partial Bath
4,483
SqFt
$891
/SqFt
2008
Built
Subdivision:
GREEN OAKS REP
County:
Orange
Call Now: 407-810-1374
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407-810-1374
1600 LEGION DRIVE1600 LEGION DRIVE1600 LEGION DRIVE1600 LEGION DRIVE
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Monthly Payment (Est.)

$18,227
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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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Listing Snapshot
Price 
$3,995,000
Days On Site 
1 Day
Bedrooms 
5
Inside Area (SqFt) 
4,483 sqft
Total Baths 
6
Full Baths 
5
Partial Baths 
1
Lot Size 
0.32 Acres
Year Built 
2008
MLS® Number 
O6415591
Status 
Coming Soon
Property Tax 
$20,740
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
17 hours agoListing updated with changes from the MLS®
yesterdayListing first seen on site
General Features
Acres 
0.32
Attached Garage 
Yes
Direction Faces 
West
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Levels 
Two
Number Of Stories 
2
Parking 
DrivewayElectric Vehicle Charging Station(s)Garage Door OpenerGarage Faces RearOn StreetOversizedAttached
Property Sub Type 
Single Family Residence
Security 
Secured Garage/ParkingSecurity SystemSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
6182
Style 
Traditional
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPhone AvailablePropaneSewer ConnectedWater Connected
Water Source 
Public
Zoning 
R-1AA
Interior Features
Appliances 
DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWine Refrigerator
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Family RoomGasOtherOutsideWood Burning
Flooring 
CarpetSlateWood
Furnished 
Negotiable
Heating 
CentralElectric
Interior 
Built-in FeaturesCoffered Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsStone CountersWalk-In Closet(s)Wet Bar
Laundry Features 
Common AreaInsideLaundry Room
Window Features 
BlindsDisplay Window(s)Double Pane WindowsDrapesShuttersWood Frames
Balcony/Porch/Lanai 
Dimensions - 20.7x12Level - First
Bedroom 2 
Dimensions - 15.9x16Level - FirstFeatures - Ceiling Fan(s), Stone Counters
Bedroom 3 
Dimensions - 15x14Level - SecondFeatures - Ceiling Fan(s)
Bedroom 4 
Dimensions - 15x14Level - SecondFeatures - Ceiling Fan(s)
Bedroom 5 
Dimensions - 14.5x13Level - Second
Dinette 
Dimensions - 13.8x11Level - First
Dining Room 
Dimensions - 15.7x13Level - First
Great Room 
Dimensions - 21.1x19.5Level - FirstFeatures - Ceiling Fan(s)
Kitchen 
Dimensions - 19.3x20.5Level - FirstFeatures - Breakfast Bar, Granite Counters, Kitchen Island
Master Bathroom 
Dimensions - 16x13Level - FirstFeatures - Double Vanity, Granite Counters
Master Bedroom 
Dimensions - 19.5x15.1Level - First
Office 
Dimensions - 15.7x13Level - First
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Exterior Features
Construction Details 
BlockStucco
Exterior 
BalconyGardenLightingOutdoor GrillPrivate YardRain Gutters
Fencing 
Fenced
Lot Features 
Corner LotLandscapedLevelPaved
Other Structures 
Cabana
Patio And Porch 
CoveredDeckFront PorchPatioSide Porch
Pool Features 
GuniteHeatedIn GroundLapSalt WaterPrivate
Private Pool 
Yes
Roof 
Shingle
View 
GardenPool
Waterview 
GardenPool
Windows/Doors 
BlindsDisplay Window(s)Double Pane WindowsDrapesShuttersWood Frames
Community Features
Community Features 
ParkPlaygroundSidewalksStreet Lights
Financing Terms Available 
CashConventional
MLS Area 
32789 - Winter Park
Roads 
Asphalt
Township 
21
Schools
School District
Unknown
Elementary School
Dommerich Elem
Middle School
Maitland Middle
High School
Winter Park High
Listing courtesy of COLDWELL BANKER REALTY (407) 923-9313



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-06-14 11:15 PM EDT

Neighborhood & Commute
Source: Walkscore
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