1600 LEGION DRIVE
WINTER PARK, FL 32789
About this home
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.
Facts & features
Interior
- Bedrooms
- 5
- Bathrooms
- 6
- Living area
- 4,483 sqft
- Heating
- Central, Electric
- Cooling
- Central Air
- Flooring
- Carpet, Slate, Wood
- Fireplace
- Yes
- Stories
- 2
- Features
- Built-in Features, Ceiling Fans(s), Chair Rail, Coffered Ceiling(s), Crown Molding, Eat-in Kitchen…
- Appliances
- Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range…
Exterior & lot
- Lot size
- 13,787 sqft (0.32 ac)
- Pool
- Yes
- Roof
- Shingle
- Construction
- Block, Stucco
- Exterior
- Balcony, French Doors, Garden, Lighting, Outdoor Grill, Private Mailbox…
Parking
- Garage
- 3 spaces
Financial
- Annual tax
- $20,740 (2025)
- Price / sqft
- $847/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Propane…
Property
- Property type
- Single Family
- Year built
- 2008
- Subdivision
- GREEN OAKS REP
- County
- Orange
Assigned schools
- Elementary
- Dommerich Elem
- Middle
- Maitland Middle
- High
- Winter Park High
Listing
- Status
- Active
- Days on market
- 34 days
- MLS #
- MFR793094955
- Source
- Stellar MLS
Listed by Brian Teach · COLDWELL BANKER REALTY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 24 comparable sales within 1 mile of WINTER PARK, FL. priced over RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $20,199/mo
- Property tax
- $2,846/mo
- Home insurance
- $200/mo
Tax, insurance and HOA are editable estimates with Florida-typical defaults — Florida homeowners insurance in particular varies widely by location and elevation. Confirm exact figures with a lender and insurer.
Price historySample data
Reference timeline for $3,795,000. Live MLS history swaps in with the Stellar feed.
| Date | Event | Price | Change |
|---|---|---|---|
| 2026-07 | Listing updated | $3,795,000 | — |
| 2026-05 | Price changed | $3,795,000 | — |
| 2026-03 | Listed | $3,795,000 | — |
NeighbourhoodSample data
Reference scores for WINTER PARK, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Location
Similar homes nearby
Homes for sale in WINTER PARK within the same price band.



