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1600 Legion Drive , Winter Park, FL 32789

$3,995,000
  • 1600 Legion Drive , Winter Park, FL 32789 Main Photo
New to the Market Active
BEDS5 BATHS5 full 1 partial SQUARE FEET4,483 MLS#O6415591
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONGREEN OAKS REP

Property 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.

1600 Legion Drive | MLS# O6415591

This single family home located at 1600 Legion Drive , Winter Park, FL 32789 is currently listed for sale with an asking price of $3,995,000. This property was built in 2008 and has 5 bedrooms and 5 full and 1 partial baths with 4483 sq. ft. Legion Drive is located in the GREEN OAKS REP subdivision. Search GREEN OAKS REP real estate on wfeble.floridaexecutiverealty.com today.

Upcoming Open Houses

Open House Sunday June 21st, 2:00pm - 4:00pm

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Garage: 3 car attached
Heating: Central, Electric
Home Style: Traditional
Lot Size: 0.32 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $20,740
Year Built: 2008

Amenities

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
Balcony
French Doors
Garden
Lighting
Outdoor Grill
Private Mailbox
Private Yard
Rain Gutters
Sidewalk

Feature Descriptions

Additional Rooms: Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Inside Utility, Storage Rooms
Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Builder: Keith D. Field
Community Features: Park, Playground, Sidewalks, Street Lights
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.
Exterior: Block, Stucco
Fencing: Fenced
Fireplace: Family Room, Gas, Other, Outside, Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Carpet, Slate, Wood
Foundation: Slab
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: Corner Lot, City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Lot Dimensions: 0.32
Other Equipment: Irrigation Equipment, Private Yard, Generator
Other Structures: Cabana
Ownership: Fee Simple
Parking: Curb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized
Parking Notes: Curb Parking, Driveway, Electric Vehicle Charging St
Patio/Porch: Covered, Deck, Front Porch, Patio, Side Porch
Pool: Deck, Gunite, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Secured Garage/Parking, Security System, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: Appointment Only, Call Listing Agent, No Lockbox, See Remarks, ShowingTime
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Meter, Water Connected
Vegetation: Trees/Landscaped
Water: Public
Water Access Y/N: No
Windows: Blinds, Display Window(s), Double Pane Windows, Drapes, Shades, Shutters, Wood Frames
Zoning: R-1AA

Room Sizes

Office: 15.7x13
Dining Room: 15.7x13
Kitchen: 19.3x20.5
Dinette: 13.8x11
Great Room: 21.1x19.5
Primary Bedroom: 19.5x15.1
Primary Bathroom: 16x13
Bedroom 2: 15.9x16
Bedroom 3: 15x14
Bedroom 4: 15x14
Bedroom 5: 14.5x13
Balcony/Porch/Lanai: 20.7x12

Local Schools

High School: Winter Park High
Middle School: Maitland Middle
Elementary School: Dommerich Elem

Listed By / Shown By

Listed By

Agency Name: COLDWELL BANKER REALTY
Agency Contact: 407-647-1211

Shown By

Agent Name: Walter John Feble
Agent Phone: Cell: (813) 474-9698
Agency Title: Florida Executive Realty

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Estimated Payment

$ 11,784.68 per month $8,891.14 Principal & Interest $1,728.33 Property Tax $1,165.21 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 06/15/2026. The listing information on this page last changed on 06/15/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 06/15/2026 12:02:14 AM EST) or Stellar MLS (last updated Sun 06/14/2026 11:44:38 PM EST). Real estate listings held by brokerage firms other than Florida Executive Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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