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8965 Old Jackson Road, Fredericktown, MO, 63645

Discover the beauty of rural living in the heart of rural Missouri wine country, where rolling landscapes, scenic country roads, and the charm of local vineyards set the scene for a slower, more intentional way of life. Spanning 7.44 picturesque acres, this inviting property blends thoughtful updates, versatile living spaces, and rustic character with room to roam, create, and cultivate your own country lifestyle. The 1,068-square-foot main level has been thoughtfully designed for convenient everyday living, with easy access from the driveway through the porch area. Important updates—including a metal roof, siding, engineered hardwood flooring, updated HVAC and heat pump, and water softener—were completed approximately seven years ago, offering peace of mind on the essentials. The split-foyer layout provides exceptional flexibility, with a lower level that functions almost as its own living quarters. A cozy wood-burning fireplace anchors the family room, while a finished full bathroom features the comfort of heated floors and a walk-in shower. The partially finished basement also offers potential for an additional bedroom, creating room to grow, host guests, or customize the space to suit your needs. Beyond the home, the property truly shines with an abundance of storage, workspace, and outdoor opportunity. A detached two-car garage, two carports, a classic red barn, and a dedicated shop with workbenches provide room for equipment, projects, hobbies, and all the essentials of country living. The shop's impressive wood stove adds warmth and character, making it an inviting retreat for pursuing your favorite craft throughout the seasons. Set amid the natural beauty of rural Missouri, the 7.44 acres feature a peaceful stream, partial woods, and open pasture, offering a beautiful backdrop for gardening, small-scale farming, animals, recreation, or simply enjoying the quiet pleasures of country life. The surrounding wine country adds another layer of appeal, with opportunities to explore local vineyards, discover regional wines, enjoy scenic drives, and experience the distinctive character of Missouri's countryside. Here, weekends can be spent tending the land, gathering with friends, exploring nearby wineries, or savoring a quiet evening as the sun settles over the pasture. Whether you envision a hobby farm, a creative workshop, a recreational escape, or a private country haven with room to roam, this property offers the space and setting to bring your vision to life. With major updates already in place, versatile living arrangements, charming outbuildings, and the appeal of Missouri wine country nearby, this is a special opportunity to embrace a lifestyle rooted in comfort, independence, and the simple pleasures of the land.

Status: Active · MLS# 26066504 · Listing Courtesy of Triple Creek Realty LLC, [email protected]

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Subdivision: N/A

List Price

$ 349,900

Status

Active

Days on market

0

MLS#

26066504

Bedrooms

3

Full baths

2

Sq. Ft. Above

1,068

Subdivision

N/A

School District

Farmington R-VII

County

St Francois

Property Type

Residential

Style

Split Foyer

Type

Residential

Additional Information

Property Tax (2025)

$990

Recent Nearby Sales in 63645

Last 6 closed homes in this zip.

Address Bd/Ba SqFt List Sold Closed
Tract 1 BCR 810, Unincorporated, MO 63645 0/0 -- $135,000 $135,000
100% of ask
Nov 10, 2026
1 Christian Court, Fredericktown, MO 63645 2/2 1,322 $220,000 $220,000
100% of ask
Nov 9, 2026
1101 Madison 9541, Unincorporated, MO 63645 3/2 1,248 $175,000 $160,000
91.4% of ask
Nov 9, 2026
1043 Madison 333, Unincorporated, MO 63645 3/2 1,247 $184,500 $184,500
100% of ask
Nov 6, 2026
1815 Madison 234, Unincorporated, MO 63645 0/0 -- $32,500 $34,020
104.7% of ask
Oct 30, 2026
1110 Madison 9292, Fredericktown, MO 63645 3/2 1,560 $110,000 $110,000
100% of ask
Oct 30, 2026

Price & Listing History

Listed for sale
Oct 22, 2026 at $349,900
Current status: Active
As of Nov 11, 2026 · $349,900

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