
$3,995,000
1600 Legion Drive
Winter Park, FL 32789
Listing updated: June 15, 2026 at 10:40 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveJun 15, 2026
- Listed$3,995,000Jun 15, 2026
- Price increased$3,995,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Green Oaks Rep
- County
- Orange
- Year built
- 2008
- Living area
- 4,483 sq ft
- Price/sq ft
- $891
- Building area
- 6,182 sq ft (Public Records)
- Lot size
- 13,787 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0255F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $20,740 (2025)
- Parcel #
- 31-21-30-3172-00-102
- Zoning
- R-1AA
- MLS #
- O6415591
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 5
- Half bathrooms
- 1
- Flooring
- Carpet, Slate, Wood
- Appliances
- 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
- Laundry
- Common Area, Inside, Laundry Room
- Stories / Levels
- Two
- Direction faces
- West
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Curb Parking, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, On Street, Oversized
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- It is the responsibility of the buyer's agent and buyer to verify with the City of Winter Park regarding any leasing or rental restrictions applicable to this property.
Exterior & Construction
- Exterior features
- Balcony, French Doors, Garden, Lighting, Outdoor Grill, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Meter, Water Connected
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Office | First | 15.7x13 |
| Dining Room | First | 15.7x13 |
| Kitchen | First | 19.3x20.5 |
| Dinette | First | 13.8x11 |
| Great Room | First | 21.1x19.5 |
| Primary Bedroom | First | 19.5x15.1 |
| Primary Bathroom | First | 16x13 |
| Bedroom 2 | First | 15.9x16 |
| Bedroom 3 | Second | 15x14 |
| Bedroom 4 | Second | 15x14 |
| Bedroom 5 | Second | 14.5x13 |
| Balcony/Porch/Lanai | First | 20.7x12 |
Listing Details
- Listing date
- 2026-06-13
- On market date
- 2026-06-15
- Original list price
- $3,995,000
- Occupant type
- Owner
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-15
- Tax legal description
- REPLAT OF GREEN OAKS Q/30 THE S 91.7 FTOF W 150 FT LOT A
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 15, 2026 at 10:40 AM ET. All data is obtained from various sources and may not have been verified by 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.
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