1600 Legion Drive, Winter Park, FL 32789
$3,495,000 - For Sale
Property Details
Price: $3,495,000
Sq Ft: 4,483
($780 per sqft)
Bedrooms: 5
Bathrooms: 5
Partial Baths: 1
City:Winter Park
County:Orange
Type:Single Family
Development:Green Oaks
Subdivision:Green Oaks Rep
Acres:0.3200
Virtual Tour/Floorplan:View
Year Built:2008
Listing Number:O6450869
Status Code:A-Active
Taxes:$20,740.00
Tax Year: 2025
Garage: 3
/ Y
Furnishings: Unfurnished
Pets Allowed: Cats OK, Dogs OK
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Scheduled Open Houses
2026-10-25 2:00 pm - 4:00 pm
Equipment:
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
Exterior Features:
Balcony
Garden
Lighting
Outdoor Grill
Private Mailbox
Private Yard
Rain Gutters
Sidewalk
View:
Garden
Financial Information:
Taxes: $20,740.00
Tax Year: 2025
Room Dimensions:
Laundry: Common Area, Inside, Laundry Room
School Information:
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Junior High: Maitland Middle
High School: Winter Park High
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View Virtual Tour
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.
Building Description: Traditional
MLS Area: 32789 - Winter Park
Total Square Footage: 6,182
Price per Square Feet: $779.61
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-19 00:00:00
Pool: Y
Pool Description: In Ground, Child Safety Fence, Gunite, Lap, Lighting, Salt Water
Furnished: Unfurnished
Windows: Blinds, Double Pane Windows, Drapes, Tinted Windows, Window Treatments
Parking: Curb Parking, Driveway, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Slate, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air
Fireplace: Y
Security: Fire Alarm, Secured Garage/Parking, Security System, Smoke Detector(S)
Laundry: Common Area, Inside, Laundry Room
Pets: Cats Ok, Dogs Ok
Sewer: Public Sewer
Lot Desc.: Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Parcel ID: 31-21-30-3172-0
Listing Courtesy Of: Coldwell Banker Realty
brian@brianteach.com
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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Additional Information:
Building Description: Traditional
MLS Area: 32789 - Winter Park
Total Square Footage: 6,182
Price per Square Feet: $779.61
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-19 00:00:00
Pool: Y
Pool Description: In Ground, Child Safety Fence, Gunite, Lap, Lighting, Salt Water
Furnished: Unfurnished
Windows: Blinds, Double Pane Windows, Drapes, Tinted Windows, Window Treatments
Parking: Curb Parking, Driveway, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Slate, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air
Fireplace: Y
Security: Fire Alarm, Secured Garage/Parking, Security System, Smoke Detector(S)
Laundry: Common Area, Inside, Laundry Room
Pets: Cats Ok, Dogs Ok
Sewer: Public Sewer
Lot Desc.: Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Parcel ID: 31-21-30-3172-0
Map of 1600 Legion Drive, Winter Park, FL 32789
Listing Courtesy Of: Coldwell Banker Realty
brian@brianteach.com
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