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.

📅 View days on the market

Days on the market

1600 Legion Dr, Winter Park, FL 32789

Price
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
Property Status and Type
Listing Type:
For Sale
Status:
Active
Previous Status:
Coming Soon
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6415591
Rooms Distribution
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
Measures
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
Property Features
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
Construction
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
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$20,740.00
Tax Year:
2025
Parking
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
Utilities
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
Community
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
Terms
Listing Terms Considered by Seller:
Cash, Conventional
Occupant Type:
Owner
Buyer Possession:
Close Of Escrow
Lease Considered:
Yes
Zoning and Legal
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
Public Schools Assigned
Elementary School:
Dommerich Elem
High School:
Winter Park High
Middle Or Junior School:
Maitland Middle
Listing History
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
Additional Information
Courtesy of:
COLDWELL BANKER REALTY
Attribution:
407-647-1211
Road Surface Type:
Asphalt
Location
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''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $100,213
Median Home Value $695,000
Median Rent $1,667/mo
Median Age 44
Population 26,884

Want to schedule an in-person or virtual tour? Have questions?

Want to schedule an in-person or virtual tour? Have questions?
Schedule a Tour or Ask a Question


Mortgage Calculator

Please note: Monthly HOA / Condo Fees Not Included. The calculator shows the listing price as home value. Update all fields at your convenience.

Calculate Your Mortgage Payment

$.00
$.00
6.5
30

Taxes and Insurance

$.00
$.00
%

Financial Analysis

%

%

$

$

$

$

$
Ver la Propiedad Ver la propiedad 1600 Legion Dr
Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. 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. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House information, if any, 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 or agent presenting the information. The data is deemed reliable but is not guaranteed by MLS GRID. Use of MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS and as amended from time to time. Some IDX listings have been excluded from this website. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available. Based on information submitted to MLS GRID as of July 13, 2026, 9:55 AM.