For Sale
New
Open House
Single family home for sale at 1600 Legion Dr, Winter Park, FL 32789 | MLS# O6450869 | Listing updated on 2026-10-21
Photo 1 of Single family home for sale at 1600 Legion Dr, Winter Park, FL 32789 | MLS# O6450869 | Listing updated on 2026-10-21
Photo 2 of Single family home for sale at 1600 Legion Dr, Winter Park, FL 32789 | MLS# O6450869 | Listing updated on 2026-10-21
Photo 3 of Single family home for sale at 1600 Legion Dr, Winter Park, FL 32789 | MLS# O6450869 | Listing updated on 2026-10-21
Photo 4 of Single family home for sale at 1600 Legion Dr, Winter Park, FL 32789 | MLS# O6450869 | Listing updated on 2026-10-21
72+
Beds Icon

Virtual Tour

Beds Icon

Street View

$3,495,000

Monthly Est:$17,396

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon4,483sqft

1600 Legion Dr, Winter Park, FL 32789

$17,396/moEst:

Get Pre-Approved

  • 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 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Orange County

  • City

    Winter Park

  • 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

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

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

DateEventPrice

10/19/2026

Source: mls_logoStellar MLS-FL #MFRO6450869

Listed for Sale

$3,495,000 -7.91%

$780/sqft

07/31/2026

Source: mls_logoStellar MLS-FL #MFRO6415591

Listing Removed

$3,795,000

$847/sqft

07/13/2026

Source: mls_logoStellar MLS-FL #MFRO6415591

Price Decreased

$3,795,000 -5.01%

$847/sqft

06/15/2026

Source: mls_logoStellar MLS-FL #MFRO6415591

Listed for Sale

$3,995,000

$891/sqft

06/13/2026

Source: mls_logoStellar MLS-FL #MFRO6415591

Coming Soon

$3,995,000 +207.31%

$891/sqft

Show more

Nearby Homes

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.

Advertising Broker: Fred McGill | Simple Showing, Inc