Home in 1600 Legion Dr Winter Park for sale with MLS# O6415591
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 Dr, Winter Park, FL 32789
- Price:
- $3,795,000.00
- Previous Asking Price:
- $3,995,000.00
- Original List Price:
- $3,995,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $846.53
- Listing Type:
- For Sale
- Status:
- Active
- Previous Status:
- Coming Soon
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6415591
- Bedrooms:
- 5
- Bathrooms Total:
- 6
- Full Bath:
- 5
- Half Bath:
- 1
- Additional Rooms:
- Attic, Den/library/office, Inside Utility, Family Room, Formal Dining Room Separate, Storage Rooms, Breakfast Room Separate
- Living Area:
- 4,483 Sqft
- Built-Up Area:
- 6,182 Sqft
- Lot Area:
- 13,787 Sqft
- Lot Size Dimensions and Info:
- 150x91.7
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- Corner Lot, Oversized Lot, Paved, Level, City Limits, Sidewalk, Landscaped
- Lot Size Acres:
- 0.32
- View from the Property:
- Pool, Garden
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Gunite, Heated, In Ground, Salt Water, Outside Bath Access, Lighting, Deck, Lap
- Security:
- Smoke Detector(s), Security System, Secured Garage/Parking
- Furnished:
- Negotiable
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
- Interior:
- Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Built-in Features, Wet Bar, Ceiling Fans(s), Split Bedroom, Stone Counters, Thermostat, Window Treatments, Solid Wood Cabinets, Crown Molding, Chair Rail, Coffered Ceiling(s), Primary Bedroom Main Floor
- Exterior:
- Balcony, Lighting, Outdoor Grill, Private Mailbox, Sidewalk, Rain Gutters, French Doors, Garden, Private Yard
- Patio and Porch:
- Patio, Deck, Covered, Front Porch, Side Porch
- Windows:
- Blinds, Drapes, Wood Frames, Double Pane Windows, Shades, Shutters, Display Window(s)
- Other Structures:
- Cabana
- Laundry:
- Common Area, Inside, Laundry Room
- Fireplace
- Fireplace:
- Gas, Wood Burning, Family Room, Other, Outside
- Air Conditioning System:
- Central Air
- Heating System:
- Central, Electric
- Fence:
- Fenced
- Vegetation and Trees:
- Trees/landscaped
- Property Entrance Faces:
- West
- Road Responsibility:
- Public Maintained Road
- Other Equipment:
- Generator, Irrigation Equipment, Private Yard
- Year Built:
- 2008
- Roof:
- Shingle
- Builder Name:
- Keith D. Field
- Architectural Style:
- Traditional
- Levels:
- Two
- Construction Materials:
- Block, Stucco
- Flooring:
- Carpet, Wood, Slate
- Number of stories:
- 2
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Property Condition:
- Completed
- Property Description:
- Walk-up
- Homestead Property
- Tax Annual Amount:
- $20,740.00
- Tax Year:
- 2025
- Garage
- Garage Spaces:
- 3
- Attached Garage
- Parking Features:
- Driveway, Garage Door Opener, On Street, Electric Vehicle Charging Station(s), Oversized, Garage Faces Rear, Curb Parking
- Sewer:
- Public Sewer
- Utilities Available:
- Phone Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected, Public, Cable Connected, Broadband/High Speed Internet Available, Propane, Sprinkler Meter
- Water Source:
- Public
- Minimum Lease Term:
- No Minimum
- Subdivision Name:
- GREEN OAKS REP
- Community Features:
- Sidewalks, Street Lights, Park, Playground
- Senior Community:
- No
- Number of Ownership Years Prior To Lease:
- 0
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Owner
- Buyer Possession:
- Close Of Escrow
- Lease Considered:
- Yes
- Tax Legal Description:
- REPLAT OF GREEN OAKS Q/30 THE S 91.7 FTOF W 150 FT LOT A
- Real Estate Folio Number (Parcel Number):
- 31-21-30-3172-00-102
- Zoning:
- R-1AA
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Dommerich Elem
- High School:
- Winter Park High
- Middle Or Junior School:
- Maitland Middle
- Originally published on:
- June 13, 2026 12:41 pm
- Active on the market since:
- June 15, 2026
- Listing Agreement executed on:
- June 13, 2026
- Price change occurred on:
- July 13, 2026 9:54 am
- Listing Status Last Changed On:
- June 15, 2026 10:25 am
- Photos updated on:
- June 24, 2026 10:38 am
- Last Modified:
- July 13, 2026 9:55 am
- Courtesy of:
- COLDWELL BANKER REALTY
- Attribution:
- 407-647-1211
- Road Surface Type:
- Asphalt
- Street Name:
- LEGION
- Street Number:
- 1600
- City:
- WINTER PARK
- State:
- Florida
- Zip Code:
- 32789
- County:
- Orange
- Latitude:
- N28° 36' 50.4''
- Longitude:
- W82° 38' 29.8''
Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates

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