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$3,495,000
Monthly Est:$17,396
5 Beds
- 6 Baths
5 full baths + 1 half bath
4,483sqft
1600 Legion Dr, Winter Park, FL 32789
$3,495,000
$17,396/moEst:
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Single Family Residence
Built in 2008
$-- HOA
13,787 sqft lot
$780/sq.ft
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.
- Houzeo last checked: 7 hours ago
- Listing updated: October 21, 2026 at 5:30 pm
- Listing Provided by: Brian Teach (407) 923-9313 | COLDWELL BANKER REALTY (407) 647-1211
- Source: Stellar MLS-FL | MLS#: O6450869

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
2
County
City
Neighborhood
--
Year Built
2008
HOA Fees
-
Finished Area
4,483 sqft
Lot Size
13,787 sqft lot
Basement Area
- sqft
MLS Name
Stellar MLS
MLS Number
O6450869
MLS Status
Active
Days on Market
3
Cumulative Days on Market
2
Open House

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 6
Interior
Window Features
Blinds, Double Pane Windows, Drapes, Tinted Windows, Window Treatments
Sewer
Public Sewer
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Flooring
Carpet, Slate, Wood
Cooling
Central Air
Heating
Central, Electric
Exterior Features
Balcony, Garden, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
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
Construction
Year Built
Year Built: 2008
Home type
Single Family Residence
Foundation Details
Slab
Architectural Style
Traditional
Roof
Shingle
Construction Materials
Block, Stucco
Property Condition
Completed
Utilities & Energy
Parking Features
Curb Parking, Driveway, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized
Fireplace Features
Family Room, Gas, Living Room, Outside
Laundry Features
Common Area, Inside, Laundry Room
Utilities
Bb/hs Internet Available, Cable Available, Electricity Connected, Fire Hydrant, Natural Gas Connected, Propane, Sewer Connected, Sprinkler Meter, Water Connected
Water Source
Public
Pool Features
In Ground, Child Safety Fence, Gunite, Lap, Lighting, Salt Water
Security Features
Fire Alarm, Secured Garage/parking, Security System, Smoke Detector(s)
Other Features
Lot Features
Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Community Features
Park, Playground, Sidewalks, Street Lights
Patio And Porch Features
Covered, Front Porch, Patio, Rear Porch, Side Porch
Vegetation
Trees/landscaped
Subdivision Name
Green Oaks Rep
Price History
| Date | Event | Price |
|---|---|---|
10/19/2026 Source: | Listed for Sale | $3,495,000 -7.91% $780/sqft |
07/31/2026 Source: | Listing Removed | $3,795,000 $847/sqft |
07/13/2026 Source: | Price Decreased | $3,795,000 -5.01% $847/sqft |
06/15/2026 Source: | Listed for Sale | $3,995,000 $891/sqft |
06/13/2026 Source: | Coming Soon | $3,995,000 +207.31% $891/sqft |
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Based on information from Stellar MLS® through Oct 22, 2026, 03:45PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.
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