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1587 S Old Hwy 66, Bourbon
$450,000
5 Beds ⋅ 3 Baths ⋅ 26069171 MLS ⋅ ACTIVE Status
Spacious 5 bedroom 3 bath home on 5 Acres. Most of this beautiful home was remodeled 5-6 years ago. Covered front porch (52x7) to enjoy the panoramic view of the setting sun. Back yard is fenced for the pets or children. 24' AG pool with 20x20 fenced composite deck. Tool shed. In addition, there is a patio w/gazebo and another composite deck off the Great Room. This deck has a composite ramp for easy access. Inside you will find open living with lots of room for entertaining. Cozy living room with wood-burning brick fireplace and a cathedral ceiling. Dining room for your family-sized table and WI pantry. Granite topped island eating bar. Kitchen cabinets are updated with gorgeous granite tops. Appliances were all replaced when remodeling was done 5-6 years ago. SS 5 burner electric range. SS French door refrigerator w/2 drawers. Bosch Dishwasher (Black). Counter top microwave can stay. Tray ceiling and additional pantry closet. Laundry room between kitchen and garage with exterior door. Then walk into your 20 x 20 Great Room with Cathedral ceiling and walkout sliding doors (3 yrs old) to deck. Attractive laminate flooring in all of these living areas. Master bedroom also has a tray ceiling with WI closet and laminate flooring. Master bath has a 4x6 floor to ceiling tiled shower and no shower door to clean. 3 additional carpeted bedrooms and 5th bedroom(not shown in photos) with laminate floor. Seller uses the 5th bedroom as an office. Good sized 10x11, 11x12 and (2) 12x13 rooms. 2 additional WI closets. Two additional bathrooms. DH Tilt-in windows. Two car attached garage. Basement area has a finished family room under the addition part of the home. 2 Gas F/A furnaces and C/A units. Lots and lots of closets and storage space. All garage doors are newer. Shingles are 2 yrs, water heater 6 yrs, Exterior building has the 3rd garage space and area for other storage items. Land is flat and open pasture. There is also a garden spot and chicken house. Gazebo stays but the two Ring cameras do not stay. Not in Bourbon City Limits. No city tax and no restrictions on the land.

1587 S Old Hwy 66, Bourbon

2362 Hwy C, Bourbon
$625,000
4 Beds ⋅ 3 Baths ⋅ 26067322 MLS ⋅ ACTIVE Status
Spacious family home on 5.5 ac., features 3 bedrooms & 2 full baths on the main level, along with an additional bedroom and full bath on the lower level. The property includes a formal dining room & a well-appointed kitchen equipped with granite countertops, stainless steel appliances (some are new), and a breakfast bar. A main floor laundry/mudroom and a central vacuum system add to the convenience of the home. Large family room w/fireplace, updated deck with stairs leads down to a patio and hot tub area. The lower level has rustic finishes and a sizable bar and lot of space for entertaining. Completing the property is a 36x30 detached garage, equipped with concrete flooring and a workshop area. The sellers recently installed a new roof on both the home and the detached garage, ensuring peace of mind for the new owners.

2362 Hwy C, Bourbon

2699 Hwy C, Bourbon
$171,000
3 Beds ⋅ 3 Baths ⋅ 26063245 MLS ⋅ ACTIVE UNDER CONTRACT Status
Enjoy the best of country living in this ranch home, offering a peaceful setting with the convenience of being just a few miles from the interstate—ideal for commuters! The main level features 3 bedrooms and 1.5 baths, along with beautiful hardwood floors that add warmth and character. Relax in the enclosed porch or step out onto the adjoining deck to enjoy the surrounding outdoor space. The walk-out lower level offers even more possibilities, featuring a large family room, an additional half bath, and a bonus room that could serve as a possible sleeping area, hobby room, or home office. Outside, you'll appreciate the detached two-car garage, two additional outbuildings for extra storage with plenty of room for tools, equipment, hobbies, or outdoor enjoyment. If you're looking for a home that combines country charm, flexible living space, and convenient access to the interstate, this property is worth a closer look. Enjoy the peaceful surroundings while keeping your daily commute within easy reach!

2699 Hwy C, Bourbon

3324 Hwy D, Bourbon
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 26065229 MLS ⋅ ACTIVE Status
STUNNING PRIVATE COUNTRY ESTATE ON 77 ACRES M/L — BEAUTIFUL HOME, SHOP & MORE! Discover the perfect blend of country elegance, privacy, and functionality with this exceptional property offering 77 acres m/l of scenic countryside in a prime location close to town! Featuring a beautiful 3-bedroom, 2.5-bath home, impressive outbuildings, and a combination of open ground and wooded acreage, this property offers endless possibilities for country living, farming, recreation, or your own private retreat. Step inside and appreciate the character and charm of the vaulted wood ceilings in the kitchen, complemented by a spacious kitchen/dining combination featuring a large island perfect for gathering and entertaining. The living room boasts impressive 9-foot ceilings, while the expansive family room offers vaulted ceilings and a wet bar, creating the perfect space for hosting family and friends. The spacious master suite is designed for comfort and relaxation, featuring a large walk-in closet, Jacuzzi tub, separate shower, double-sink vanity, and bidet. A convenient main-floor laundry room includes a half bath, double closets, cabinetry, and a refrigerator for added storage and functionality. Additional features include a full walk-out basement with a safe room and central vacuum throughout the home. Enjoy the peaceful surroundings from the inviting wraparound porch, where scenic views and the seclusion of the countryside create the perfect setting to unwind. The land features approximately 30 acres m/l of open ground, with the balance wooded, offering a wonderful combination of pasture, wildlife habitat, hunting, and recreational opportunities. The property is fenced, with partial pipe fencing, making it well-suited for livestock or hobby farming. The improvements are equally impressive! You'll find multiple barns, an oversized detached 3-car garage, and a massive 40' x 70' shop with its own well and septic system—ideal for equipment, farm operations, hobbies, storage, or workshop needs. With three wells on the property, there are additional water resources for a variety of uses. A chip-and-seal driveway provides convenient access to this secluded setting. Whether you're looking for a working farm, recreational paradise, hunting retreat, or private country estate, this property delivers an outstanding combination of comfortable living, usable acreage, and versatile improvements—all conveniently located close to town. A rare opportunity to own a beautiful home with acreage, privacy, scenic views, and room to make your dreams a reality. Don't miss out—call today to schedule your private showing!

3324 Hwy D, Bourbon

2527 Hwy Jj, Bourbon
$1,499,000
4 Beds ⋅ 2 Baths ⋅ 26064546 MLS ⋅ ACTIVE Status
Rare opportunity to own this 77.3 acre farm that has been cared for and improved with TLC in every step. You can feel the history, appreciate the character and envision the next generation making dreams come true at this address. Warmth greets you through out with modern newer amenities. Family room with wood burning fireplace, inviting kitchen, oak cabinets, appliances, pantry, front dining room with original hardwood flooring, bay window, office area, hall bath offers a soaker tub & ship lap walls. Spacious primary bedroom suite, walk in closet with shower and garden tub, linen closet. 2nd main floor bedroom and laundry room with storage and cabinets. The upper floor offers two more appealing bedrooms with ship lap, bead board & plenty of closet space. Detached two car garage, covered breezeway, side entrance. Love the back covered patio with bar area, fireplace to enjoy the on peaceful & tranquil evenings. 77+ acres is over 3/4 open, lush pasture, some woods, fenced cross fenced, 3 hydrants, pond and 3 waterers. Ready for cattle, horses or choice of your own to roam. One original horse barn, barn with 7 stalls, 24x24 shed, 40x50 barn, 30x60 open equipment building, Located on black top road, 3 miles out of the town of Bourbon, and minutes to I-44 for all of your convenience this 77 acre farm is one not to pass up. So much to offer, wonderful home, beautiful property and all of the buildings and barns ready for the next owner.

2527 Hwy Jj, Bourbon

3031 Oak Haven Ln, Bourbon
$445,000
3 Beds ⋅ 4 Baths ⋅ 26064338 MLS ⋅ ACTIVE Status
Situated on the corner of the desirable subdivision of Forest Knolls with 2.7 pristine acres at your disposal. This classic traditional home perfectly blends timeless elegance with expansive, park-like privacy. Boasting 3 bedrooms, 4 bathrooms, and a fully finished basement, this magnificent property is an entertainer's paradise and the ultimate backdrop for creating lifelong family memories. Three generously sized bedrooms paired with beautifully appointed bathrooms, ensuring every family member and guest enjoys maximum comfort and privacy. A seamless flow between the formal dining areas and a sunny kitchen, making everyday living and hosting completely effortless. Don't miss the rare opportunity to own one of Forest Knoll's premier properties!

3031 Oak Haven Ln, Bourbon

2899 Old Hwy 66, Bourbon
$385,000
3 Beds ⋅ 2 Baths ⋅ 26063680 MLS ⋅ ACTIVE Status
Beautifully appointed 3-bedroom, 2-bath home built in 2020 and set on 5.24 beautiful acres. Thoughtfully designed with an open-concept layout, this home offers the perfect blend of modern style, comfort, and peaceful country living. Beautiful wood-beam accents and vaulted ceilings add warmth, character, and an inviting sense of space throughout the main living area. The stunning kitchen is truly the heart of the home, featuring an oversized island, an abundance of custom cabinetry, and stainless steel appliances—creating the perfect space for cooking, gathering, and entertaining. The desirable split-bedroom floor plan provides privacy and functionality, with a spacious primary suite featuring a private en-suite bath. A spacious laundry room just off the kitchen adds convenience and functionality. Step outside to enjoy the peaceful setting from the covered front porch or spacious covered concrete back patio, perfect for morning coffee, relaxing evenings, or entertaining guests. A 2-car garage provides convenient parking and additional storage. With its newer construction, thoughtful layout, beautiful kitchen, charming wood-beam accents, vaulted ceilings, and 5.24 acres to enjoy, this property offers a wonderful opportunity to have the space and tranquility of country living with the comfort and style of a newer home. Come see all this beautiful property has to offer!

2899 Old Hwy 66, Bourbon

229 Anthonies Mill Rd, Bourbon
$40,000
26058483 MLS ⋅ ACTIVE Status
2 +/- Acre WATERFRONT lot at Anthonies Mill Resort NOW AVAILABLE! Build your new home overlooking the lake and build your own waterfront dock surrounded by the beauty of the rolling hills in this part of the country! This sloped lot was prepared for a walk-out basement home overlooking the lake and sheltered from the road via an easement access from the side rather than the top of the property. Join the private, gated community and all that Lake Life has to offer... skiing, boating, fishing tournaments, and community events for the holidays! The community includes a Member pool overlooking the lake, a sandy beach for volleyball, paddleboard docking, an inflatable bounce dock for lake play, and tennis/basketball courts for additional entertainment. Just over an hour from St. Louis and only 15 minutes off the interstate...make time to see this listing today!

229 Anthonies Mill Rd, Bourbon

4411 Rock Rd, Bourbon
$769,900
5 Beds ⋅ 6 Baths ⋅ 26055213 MLS ⋅ ACTIVE Status
AN EXTRAORDINARY ESTATE - 4411 ROCK RD IN BOURBON! Set upon 18.25 +/- picturesque acres in the Sullivan School District, this remarkable 5-bedroom, 5.5-bath contemporary residence delivers an unparalleled combination of architectural drama, privacy, luxury, and resort-style living. From the moment you enter, 3-story atrium windows command attention, filling the home with natural light and framing spectacular views. The gourmet kitchen is thoughtfully appointed with custom-designed cabinetry, an expansive island and breakfast bar, 8-burner stove, and pot filler. The vaulted living room flows effortlessly toward a covered, shaded deck overlooking the backyard and in-ground pool. The lower level elevates entertaining to an entirely new level with a full kitchen and bar, spacious family room, full gym, 2 generously sized bedrooms, 1.5 baths, covered patio, and direct pool access. A mature banana tree growing beside the staircase adds an unforgettable touch—and yes, it produces edible bananas! Each upper-level bedroom offers exceptional space and its own private full bath. An oversized garage with loft offers additional possibilities. Beyond the residence, the grounds unfold with gently rolling acreage, a fully stocked +/- 1-acre pond, wooded areas, trails, spring-fed Carter Creek, and a fenced recreation area with fire pit. A tree-lined, lamp-post-lit driveway provides a fitting entrance to this remarkable property. Impeccably designed with countless thoughtful details, this is not simply a home—it is a private estate designed to be experienced.

4411 Rock Rd, Bourbon

129 Shamrock Ln, Bourbon
$299,999
3 Beds ⋅ 1 Baths ⋅ 26054984 MLS ⋅ ACTIVE Status
Welcome to your own private retreat! Whether you're looking for a peaceful place to call home, a hunting and recreational property, or a getaway where you can bring your vision to life, this property offers plenty of potential. Situated on over 5 acres, this 3-bedroom, 1-bath home features an open-concept main floor with a spacious kitchen, living room, and dining area, along with a main-floor bedroom, full bathroom, laundry room, and convenient access to the oversized attached garage. Upstairs, you'll find two additional bedrooms, providing plenty of space for family, guests, or a home office. Outside, enjoy an established yard surrounded by woods and natural beauty. The property offers two entrances, an additional detached garage with a concrete floor, and plenty of room for animals, outdoor equipment, hunting, recreation, or off-road toys. Bring your ideas and make this property your own—whether you're dreaming of a country home, weekend retreat, hunting camp, or recreational getaway, the possibilities are here!

129 Shamrock Ln, Bourbon

270 Bridle Spur Rd, Bourbon
$39,900
26054846 MLS ⋅ ACTIVE Status
Build your dream home on this beautiful 2.7-acre lot in the desirable gated community of Anthonies Mill! Offering a unique combination of acreage, usable land, and waterfront setting, this property provides plenty of space to bring your vision to life. The lot offers a consistent layout from one side to the other, extending all the way down to the water, providing an exceptional connection to the lake and surrounding natural beauty. Its location is also conveniently positioned near the center of the water, offering a wonderful setting within the community. Enjoy all that Anthonies Mill has to offer, including multiple lakes for fishing, swimming and kayaking, a community pool, tennis courts, basketball court, clubhouse, playground, scenic surroundings, and golf-cart-friendly roads. Whether you’re looking to build a weekend getaway, family retreat, or forever home, this property offers an incredible opportunity to enjoy acreage and lake-oriented living in a private, gated community. Come see what makes 270 Bridle Spur such a special opportunity!

270 Bridle Spur Rd, Bourbon

334 Winter Ln, Bourbon
$205,000
26047882 MLS ⋅ ACTIVE Status
Build your dream home on this beautiful 20.3 acre property in Bourbon, Missouri! With a well and electric already on site, much of the groundwork is in place to bring your vision to life. Featuring mostly open pasture with gently rolling hills and scattered woods, this versatile property is ideal for horses, livestock, a hobby farm, or simply enjoying the peace and privacy of country living. Bring your building plans and create the country lifestyle you've been dreaming of, with plenty of room for a home, barn, shop, and more. Located in the Bourbon School District but just minutes from Sullivan, this property offers the perfect balance of rural living with convenient access to shopping, dining, schools, and everyday amenities. Don't miss this opportunity to own a beautiful piece of Missouri countryside that's ready for your next chapter.

334 Winter Ln, Bourbon

1574 Turkeyfoot Rd, Bourbon
$950,000
4 Beds ⋅ 5 Baths ⋅ 26045271 MLS ⋅ ACTIVE Status
Beautifully maintained and updated 4 bedroom 4.5 bath home on 47+/- acres near Bourbon, MO. An amazing country setting filled with woods and wildlife. This custom homes features an inviting covered front porch, 2x6 construction, and lots of woodwork. The main floor starts with 2-story entryway, oak flooring, a main floor master suite, large living room, kitchen with custom cabinets, breakfast and a dining room. Upstairs are two more spacious bedrooms and a full bathroom. The finished walk out lower level includes a 9 ft pour, an extra bedroom, craft room, wet bar, full bathroom and lots of storage. The attached 3 car garage is oversized, has A/C, a 1/2 bathroom and attic access. An additional newer outbuilding with electric provides plenty of space for all your toys or hobbies. Schedule your private tour today and come see everything this property has to offer. Just 5 miles from Bourbon and I-44 and only an hour from St. Louis.

1574 Turkeyfoot Rd, Bourbon

1574 Turkeyfoot Rd, Bourbon
$950,000
4 Beds ⋅ 5 Baths ⋅ 26041964 MLS ⋅ ACTIVE Status
Beautifully maintained and updated 4 bedroom 4.5 bath home on 47+/- acres near Bourbon, MO. An amazing country setting filled with woods and wildlife. This custom homes features an inviting covered front porch, 2x6 construction, and lots of woodwork. The main floor starts with 2-story entryway, oak flooring, a main floor master suite, large living room, kitchen with custom cabinets, breakfast and a dining room. Upstairs are two more spacious bedrooms and a full bathroom. The finished walk out lower level includes a 9 ft pour, an extra bedroom, craft room, wet bar, full bathroom and lots of storage. The attached 3 car garage is oversized, has A/C, a 1/2 bathroom and attic access. An additional newer outbuilding with electric provides plenty of space for all your toys or hobbies. Schedule your private tour today and come see everything this property has to offer. Just 5 miles from Bourbon and I-44 and only an hour from St. Louis.

1574 Turkeyfoot Rd, Bourbon

274 Oak Ridge Rd, Bourbon
$15,000
26034776 MLS ⋅ ACTIVE Status
CREATE MEMORIES! Build your dream home or dream weekend get-away on this 1.2 acre (m/l) lot at the private, gated community of ANTHONIES MILL RESORT. This lot is only slightly sloped and perfect for a walk-out basement. Amenities not offered at other lake communities include: Skiing, Boating, Tubing, Fishing, & Playing on beautiful 110 acre Lake Ashley, Swimming Pool with Bathhouses for owners and guests, Sand Beach with Games and Volleyball, Beach Swimming area with Water Toys, Lighted Basketball, Tennis and Pickleball Courts, two Marinas, three Pavilions (one with fireplace) for family gatherings, Boat Storage, Horse Stables and more! Two additional lakes for quiet fishing stocked with Bluegill, Large Mouth Bass, Catfish, Crappie and a Campground available to owners with Hook-ups and Bathrooms. Enjoy watching deer, turkey, birds and other wildlife from your home on this lot in a quiet part of the community or simply enjoy all the amenities offered just over an hour from St Louis! South dock & Pavilion, Swing set, & Ball fields just down the hill.

274 Oak Ridge Rd, Bourbon

522 Hwy Ff, Bourbon
$335,000
5 Beds ⋅ 3 Baths ⋅ 26033715 MLS ⋅ ACTIVE UNDER CONTRACT Status
BUYER INCENTIVE! Seller is offering to cover 5% of the purchase price to cover buyers closing costs, lender fees, down payment, (what is allowed by your lender) etc. up to $16,750! Versatile 5-Bedroom Home on 6.32 Acres with Multigenerational Living Potential! Discover the possibilities at this spacious 5-bedroom, 3-full-bath home situated on 6.32 beautiful acres. With over 2,500 square feet of living space and a unique flexible layout, this property offers room for extended family, guests, a hobby farm, or simply more space to enjoy country living. The main level features 3 bedrooms and 2 full bathrooms, including a primary suite with a beautifully tiled bathroom and no-step walk-in shower. The spacious living room features a wood-burning stove, while the kitchen offers a pantry area and plenty of functionality. A recreation room, multiple storage and bonus rooms, and convenient washer and dryer hookups add even more usable space. The upper level provides a second living area with 2 additional bedrooms, a full bathroom, a comfortable sitting area, and a bright sunroom. The upper kitchen is equipped with a cooktop, built-in oven, and refrigerator, along with its own washer and dryer hookups and separate water heater. With separate exterior access and dedicated living spaces, the upper level offers excellent potential for multigenerational living, extended family, guests, or anyone needing additional private space. Outside, the property is set up with the homesteader in mind. Enjoy a 27x38 metal carport with metal trusses, multiple storage sheds, a lean-to with electric, chicken coop, garden beds, and dedicated garden space ready for planting. Sellers also installed a brand-new private well in 2025. Beautiful landscaping surrounds the home, while the 6.32 acres provide plenty of room for livestock, gardening, recreation, or simply enjoying the peace and privacy of country living. If you’re looking for a property that offers space, flexibility, acreage, and the opportunity to create the lifestyle you’ve been looking for, this one is worth a look!

522 Hwy Ff, Bourbon

Turkey Foot Rd, Bourbon
$475,000
26032548 MLS ⋅ ACTIVE Status
Tucked away on a quiet gravel road in the heart of Crawford County, this breathtaking 78.44± acre tract offers the kind of beauty and privacy that’s becoming increasingly difficult to find. Towering pines and mature hardwoods stretch across rolling Ozark terrain, creating a peaceful, park-like setting with endless opportunities to build, explore, hunt, and enjoy the outdoors. The property features multiple incredible building sites with excellent privacy and gently rolling topography ideal for a dream home, hunting cabin, or family retreat. Seasonal waterfalls and wet-weather creeks wind through portions of the property during rains, adding to the natural beauty and character of the land. A great open pasture also provides an outstanding location to establish food plots, trail systems, campsites, or recreational area. The timber is open and easy to walk, making it simple to envision future improvements while still maintaining the secluded feel buyers are searching for. Wildlife sign is abundant throughout the property, offering strong deer and turkey hunting potential. Located near Bourbon and Leasburg with convenient access to Interstate 44, this property delivers the perfect combination of accessibility and seclusion. Whether you’re looking for a recreational getaway, hunting property, private homestead, or long-term investment, the possibilities here are truly endless. The owners are also open to dividing the property, creating additional opportunities for buyers seeking smaller acreage options.

Turkey Foot Rd, Bourbon

341 Spruce St, Bourbon
$169,900
2 Beds ⋅ 2 Baths ⋅ 26018989 MLS ⋅ ACTIVE Status
Completely restored from the foundation up, this beautifully renovated home at 341 Spruce St in Bourbon offers the perfect blend of craftsmanship, efficiency, and long-term durability. No detail was overlooked in this full-scale transformation. The home features all new plumbing to the city sewer connection, updated water supply lines, and fully replaced electrical wiring providing peace of mind for years to come. Inside, you’ll find new drywall, flooring throughout, and mineral wool insulation for superior energy efficiency and sound control. The kitchen is built to impress with solid white oak Amish-crafted cabinetry constructed to last generations—paired with quartz countertops, porcelain tile finishes, and a commercial grade double oven induction stove. Bathrooms continue the high-end feel with matching porcelain tile and quality finishes. This is not your typical renovation this is a true rebuild with lasting quality at its core.

341 Spruce St, Bourbon

Tbb State Hwy N, Bourbon
$69,800
26013756 MLS ⋅ ACTIVE Status
Escape to your own private retreat on this beautiful 9.82-acre wooded property just outside of Bourbon. Tucked away for peace and privacy yet easily accessible via a well-maintained blacktop road, this land offers endless possibilities. With no known restrictions, you have the freedom to build your dream home, establish a peaceful weekend getaway, or simply enjoy it as a secluded recreational escape. The mature trees create a tranquil, natural setting—perfect for exploring, hiking, or enjoying the quiet of the countryside. Utilities are nearby, and the layout provides flexibility for site planning and development. Whether you’re looking for a private homestead, a hunting or camping spot, or to invest in land with room to grow, this property delivers space, privacy, and opportunity—all within reach of Bourbon’s small-town charm and the conveniences of larger nearby communities, while being just an hour outside of St. Louis.

Tbb State Hwy N, Bourbon

Listings courtesy of Mid America Regional Information Systems Internet Data Exchange as distributed by MLS GRID.


Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of 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. Some listings have been excluded from this website.


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