Welcome to 8705 County Road 99 in Headland—a truly one-of-a-kind historic estate where timeless Southern charm meets rich local history. Situated on nearly 6 gated and fenced acres in the highly desirable Headland school district, this remarkable property offers privacy, character, and space unlike anything else on the market.… Read More Built in 1969 by a renowned pilot, this 3,528 sq ft architectural gem was uniquely designed so that its aerial footprint resembles the shape of an airplane—a rare and fascinating nod to its original owner's legacy. Inside, you'll find 4 bedrooms, 3 bathrooms, and the convenience of one-level living, all filled with historic character and generous living spaces designed for both everyday comfort and entertaining. Major updates provide peace of mind while preserving the home's charm, including new roof, windows, HVAC units, and hot water heaters (2018), plus septic tanks pumped/cleaned in 2026 and new front field lines installed in 2026. Step outside and experience the full beauty of the grounds featuring: A large restored two-story barn Inviting sunroom Elegant backyard fountain Charming covered gazebo Expansive fenced acreage ideal for recreation, animals, or simply enjoying the peaceful setting This is more than a home—it's a piece of Wiregrass history offering the rare opportunity to own a truly distinctive estate with modern updates and unforgettable character. Read Less
Built in 1969, Building areatotal: 3,528, Living area: 3,528, Levels: "One", 1 story, Architectural style: "Ranch Rambler", "Other", Construction materials: "Brick", Other structures: "Barn(s)"
Cooling
"Heat Pump"
Accessibility Features
Accessibility features: "Not Handicap Accessible"
Fence
"Wrought Iron", "Wood"
Fireplaces
2 total fireplaces, "2"
Floors
"Tile", "Vinyl"
Foundation
Foundation details: "Crawl Space", "Slab"
Garage
2 garage spaces
Heating
"Heat Pump"
Interior Features
"Bonus Room", "Den", "Sunroom"
Lot
5.4 acres, 235,224 square feet, Size: 5
Parking
2 covered spaces, 2 total parkings, "2 Car", "Garage Door Opener"
Pool
"None"
Property
Property type: Residential, "Covered", "Porch-Covered", "No Waterfront"
Roof
"Metal"
Sewer
"Septic Tank"
Taxes
Tax annual amount: $1,044, Tax year: 2025
Utilities
Electric: "Alabama Power", "County Trash Service"
Windows
"Aluminum Frames", "Double Pane Windows"
Find The Perfect Home
'VIP' Listing Search
Whenever a listing hits the market that matches your criteria you will be immediately notified.
Information herein is deemed reliable but not guaranteed and 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. Listings last updated on .
Confirm your time
Fill in your details and we will contact you to confirm a time.
