MLS Listings for Sale in Charleston, MO

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ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Beautifully remodeled historic home sitting right in the heart of the Dogwood Azalea trail of Charleston. From the welcoming front porch to the coffee bar, this is one to see! This charming 2 story home features 4 bedrooms, 2.5 bathrooms, living room with pocket doors, and has been completed updated. Whether you are looking for cozy family time or entertaining, this home offers ample space for daily life, dining, cooking, along with well proportioned bedrooms and dedicated storage space. This 1910 home not only has been completely remodeled, this also includes roof and HVAC system to those updates. Make sure to schedule your tour today!

$250,000

4 beds2.5 baths3,135 sq ft

409 E Cypress, Charleston, MO 63834

Coffee bar • 0.37 acre lot • Parking

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Welcome to this beautifully updated 4 bedroom, 2 1/2 bath home, nestled on a nearly half acre lot, it is the perfect blend of indoor comfort and outdoor living. Recent upgrades include a new roof, fresh paint inside and out, new flooring and lighting, along with electrical updates. Step inside to find a flexible layout, including a formal living room, currently used as a dining room, offering a versatile space to fit your needs. The kitchen features ample storage, a peninsula for extra counter space, and a dining area that flows into the cozy and inviting den with a fireplace and built-in shelving—ideal for relaxing or entertaining. The spacious primary bedroom is located on the main

$230,000

4 beds2.5 baths2,738 sq ft

201 S Clayton St, Charleston, MO 63834

New lighting • Fresh paint • Electrical updates

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Charming Fixer-Upper, perfect for investors, flippers, DIY enthusiasts, and those who appreciate the character of older homes! Bring your vision as this 1915 property is ready for a makeover! Every room has endless potential. Whether you’re looking to restore its original charm or create a modern retreat, this property offers the perfect canvas. Conveniently located within walking distance to the grocery store and other town amenities. With its prime location and large lot, this property is full of opportunity. Bring your imagination and turn this diamond in the rough into something special! (Property is located in B-1 General Business District and X500 flood zone).

$39,500

1 bed1 bath2,211 sq ft

514 S Main St, Charleston, MO 63834

1915 property • Large lot • 0.46 acre lot

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Welcome to this beautifully preserved 1937 home, full of character and smart updates. With 3 bedrooms and 1 fully renovated bathroom, this cozy space makes the most of every square foot—perfect for first-time buyers, downsizers, or anyone looking for low-maintenance living with vintage appeal. Original hardwood floors, recently refinished, run throughout most of the home, adding warmth and timeless charm. The updated kitchen features stylish butcher block counters, includes appliances, and a convenient coffee or serving bar—great for casual mornings or hosting friends. Enjoy peace of mind with updated windows, a new central heat & air system (2021), and a Ring security sys

$109,900

3 beds1 bath1,034 sq ft

901 E Cypress St, Charleston, MO 63834

Updated windows • Ring security system • Corner lot

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Welcome to this one of a kind, custom-built luxury residence, situated just steps from the country club, offering golf, dining, and amenities. Stepping inside, you'll be captivated by the attention to detail and design. The formal living room sets the tone with a stunning marble fireplace, built-in shelving, and double doors to the screened patio. A separate formal dining room provides the perfect setting for hosting, while the dedicated home office offers a quiet space to work. The main-level primary suite is a true retreat—flooded with natural light and featuring direct access to the patio, along with a luxurious en-suite bathroom. Enjoy two expansive walk-in closets, dual vanities,

$875,000

4 beds5 baths5,943 sq ft

328 S Kathie Dr, Charleston, MO 63834

Screened patio • Marble fireplace • Formal living room

Property at 504 E Cypress St, Charleston, MO 63834, 4 beds, 2.5 baths

$229,900

4 beds2.5 baths2,701 sq ft

504 E Cypress St, Charleston, MO 63834

Property at 815 Gail St, Charleston, MO 63834, 5 beds, 3.5 baths

$275,000

5 beds3.5 baths2,559 sq ft

815 Gail St, Charleston, MO 63834

Property at 328 S Ann Dr, Charleston, MO 63834, 5 beds, 4 baths

$599,900

5 beds4 baths5,318 sq ft

328 S Ann Dr, Charleston, MO 63834

Property at 601 Elkins, Charleston, MO 63834

$4,000

0 beds— baths— sq ft

601 Elkins, Charleston, MO 63834

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NEW 26 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Welcome home to this inviting 4 bed, 3.5 bath brick beauty featuring new flooring throughout the front of the house and a private master suite tucked away in the back. Enjoy plenty of room to spread out with a large garage for vehicles and storage, plus an above-ground pool perfect for relaxing or entertaining. This home offers comfort, space, and great small-town charm—ready for its next owner to make it their own!

$190,000

4 beds3.5 baths2,442 sq ft

319 Crystal Lake Dr, Wickliffe, KY 42087

0.74 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
This one does not disappoint!! Looking for a large home, move in ready, and just one that gives you those cozy and inviting home vibes? I have it! This home sits in an great location on a corner lot. This beautiful home host 4 bedrooms and 2 baths. Wonderful layout for a growing family with multiple living spaces, multiple fireplaces, office area, huge laundry room, and the possibility of a 3rd bathroom, you will fall in love quickly! This home has large bedrooms, spacious bathrooms, dining in the kitchen and a separate formal dining, large pantry, and storage gallor. You will also get storage room in the attached garage and a storage building. You have to see this one in person to appr

$275,000

4 beds2 baths2,566 sq ft

445 Margaret Dr, East Prairie, MO 63845

0.37 acre lot • Garage • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Sitting down a peaceful, country road is this 3 bedroom, 3 bath home on 3.5 wooded acres. Numerous updates in the past year including a new, water heater, private well, evaporator coil in HVAC, vinyl plank flooring in the bedrooms & main level bathrooms and new gutters. Also a new refrigerator, gas range and dishwasher and new bathroom fixtures. Beautiful hardwood floors in the living room, kitchen & dining room. The full, walk-out basement is a blank slate. There are two additional bedrooms, a potential family room and the third bathroom. These rooms just need flooring. The basement also has utility sink and a storage room. You'll love the views of the wildlife from the covere

$199,900

3 beds3 baths2,552 sq ft

451 County Road 1320, Bardwell, KY 42023

3.5 acre lot • Garage • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Discover the natural beauty of this 26.26-acre property tucked between County Roads 1320 and 1324 in Western, KY. This expansive tract offers a rare mix of wooded privacy, elevation, and natural resources. Recently analyzed by a certified lab, there is a silica sand deposit that is over 98% quartz, adding potential for future resource value or development interest. The land is ideal for hunting, recreation, or simply escaping into nature. Rolling terrain and mature trees create the perfect habitat for deer, turkey, and other wildlife, while the bluff setting offers scenic views and seclusion. Whether you’re looking for a private hunting retreat, or a piece of untouched Kentucky countr

$78,780

— beds— baths— sq ft

000 County Road 1320, Bardwell, KY 42023

26.26 acre lot • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Welcome to 37 Kyle Drive in Benton, MO - completely remodeled and move-in ready! Located in the desirable Kelly School District, this home offers 1,650 square feet of updated living space on a 0.90-acre lot. Originally a manufactured home, it has been permanently affixed to the property and updated throughout for modern comfort. Step inside to find a bright, open floor plan featuring new flooring and fresh paint. The kitchen boasts new countertops and cabinetry with plenty of storage space and an adjoining dining area. The primary suite includes a spacious layout and an updated bath with dual vanities and a large soaking tub. Enjoy outdoor living from the covered front porch or the covered

$189,900

3 beds2 baths1,650 sq ft

37 Kyle Dr, Benton, MO 63736

0.9 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Charleston, MO
Premium River Bottom Investment: 440 +/- Acres in the Wolf Island Region of Mississippi County, Missouri- An exceptional opportunity to acquire approximately 440 acres of highly productive, Mississippi River bottom row crop land in the renowned Wolf Island region of Mississippi County, Missouri. This property is an excellent agricultural asset, distinguished by its superior soils and irrigation capabilities. The history of this area is defined by the very land itself; centuries of Mississippi River floods deposited alluvial, nutrient-rich topsoil here, making the reclaimed lands some of the most sought-after and high-yielding acreage in the country. The fields consist primarily of Commerce

$4,700,000

0 beds— baths— sq ft

0 County Road 507, East Prairie, MO 63845

440 acre lot • Car-dependent

Property at 942 Crews Rd, Wickliffe, KY 42087, 3 beds, 2 baths

$479,900

3 beds2 baths2,637 sq ft

942 Crews Rd, Wickliffe, KY 42087

Property at 207 W Olive, East Prairie, MO 63845, 5 beds, 2 baths

$180,000

5 beds2 baths1,662 sq ft

207 W Olive, East Prairie, MO 63845

Property at 1355 Ridgeway Cir, Benton, MO 63736, 5 beds, 7 baths

$1,425,000

5 beds7 baths6,646 sq ft

1355 Ridgeway Cir, Benton, MO 63736

Property at 2035 Martin Luther King Jr Dr, Cairo, IL 62914, 3 beds, 2 baths

$45,000

3 beds2 baths2,700 sq ft

2035 Martin Luther King Jr Dr, Cairo, IL 62914

Property at 200 Margaret Dr, East Prairie, MO 63845, 2 beds, 2 baths

$228,900

2 beds2 baths1,888 sq ft

200 Margaret Dr, East Prairie, MO 63845

Property at 81 S 523rd Rd, East Prairie, MO 63845, 3 beds, 2.5 baths

$330,000

3 beds2.5 baths3,463 sq ft

81 S 523rd Rd, East Prairie, MO 63845

Property at 1608 County Road 711, Matthews, MO 63867, 4 beds, 4 baths

$3,250,000

4 beds4 baths3,000 sq ft

1608 County Road 711, Matthews, MO 63867

Property at 20601 Maggie Ln, Tamms, IL 62988, 2 beds, 1.5 baths

$450,000

2 beds1.5 baths2,150 sq ft

20601 Maggie Ln, Tamms, IL 62988

Property at 00 State Route 58, Clinton, KY 42031

$2,899,900

— beds— baths— sq ft

00 State Route 58, Clinton, KY 42031

Property at 000 County Road 1320, Bardwell, KY 42023

$78,780

— beds— baths— sq ft

000 County Road 1320, Bardwell, KY 42023

Property at 000 Center Church Rd, Villa Ridge, IL 62996

$74,900

— beds— baths— sq ft

000 Center Church Rd, Villa Ridge, IL 62996

Property at Lot 11 County Highway 401, Benton, MO 63736

$77,000

0 beds— baths— sq ft

Lot 11 County Highway 401, Benton, MO 63736

Property at 00 Road Runner Hollow Rd, Olive Branch, IL 62990

$375,000

0 beds— baths— sq ft

00 Road Runner Hollow Rd, Olive Branch, IL 62990

Property at 0 Mayfield Rd, Wickliffe, KY 42087

$194,500

— beds— baths— sq ft

0 Mayfield Rd, Wickliffe, KY 42087

Based on information submitted to the MLS GRID as of Wed Nov 12 2025. 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.

MLS Listings for Sale in Charleston

There are currently 9 mls listings for sale in Charleston at a median listing price of $230K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Charleston stay on the market for 46 days. This map is refreshed with the newest listings in Charleston every 15 minutes.

In the past month, 1 home has been sold in Charleston. Find your dream home in Charleston using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Charleston are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Charleston. Our Charleston real estate stats and trends will give you more information about home buying and selling trends in Charleston. If you're looking to sell your home in the Charleston area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Charleston with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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