Refine Search
Sort by
5616 W SR 256, Madison
$379,900
3 Beds ⋅ 2 Baths ⋅ 2026010877 MLS ⋅ ACTIVE Status
First time on the market! Move-in-ready quality stick-built home with updates on 3.8 beautiful acres (mix of cleared & wooded), conveniently located between Madison/Hanover. Welcoming, relaxing porch sits at 50' long. This well-maintained property offers 3 bedrooms & 2 full bathrooms all on one floor. Two amazing pole barns—#1- 40' x 40' & 18 ft. tall w/ 20'x40' reinforced second floor. #2 -30' x 60' & 9' tall. Both with concrete floors/electric. These buildings provide plenty of room for storage, a workshop, equipment, recreational vehicles, hobbies & more. The enclosed covered cement pad- shelter house? dog kennel? You decide. Two car attached garage. Inside, you will find quality Andersen windows and doors, poured-concrete basement for additional storage & storm cover. There is even more potential upstairs! The upper level has 950 sq. ft. & is framed, incl plumbing stubbed in for full bathroom giving the new owner an excellent opportunity to finish the space to fit their needs—whether for additional bedrooms, living space, a home office, or a guest suite. Efficiency at its best- dual heat sourced: Geothermal heat & a coal/wood-burning furnace ductwork plumbed w/thermostat. Underground dog fence conveys. Washer & Dryer can stay.

5616 W SR 256, Madison

515 N Hereford Lane, Madison
$339,900
4 Beds ⋅ 2 Baths ⋅ 2026011013 MLS ⋅ ACTIVE Status
NEW PRICE!! Looking for space, storage, and lake access? This well-maintained 4-bedroom, 2 full bath home offers a huge living room filled with natural light, creating the perfect gathering space for family and friends. The adjacent eat-in kitchen provides plenty of room for everyday meals and entertaining. This home also features new shingles! Enjoy access to the popular Hereford Lake, where you can spend your days fishing, kayaking, or simply relaxing by the water. Conveniently located just minutes from Historic Downtown Madison—recently voted the Best Small Town in the Midwest—you'll have easy access to shopping, dining, festivals, and riverfront attractions. A standout feature of this property is the impressive 24' x 36' detached garage. Complete with concrete floors, electric service, partial insulation, and HVAC, this versatile space stays comfortable year-round and is ideal for vehicles, hobbies, storage, or a workshop. Whether you're looking for a full-time residence or a place to enjoy the outdoors, this property offers the perfect combination of comfort, convenience, and recreation. Grab your kayaks and fishing poles and come see all this home has to offer!

515 N Hereford Lane, Madison

306 Fairmount Drive, Madison
$419,900
4 Beds ⋅ 3 Baths ⋅ 2026011001 MLS ⋅ ACTIVE Status
Authentic All-Brick Mid-Century Modern with 3,600 SF & Seasonal Ohio River Views! Step into quintessential 1960s architecture with this expansive 4-bedroom, 2.5-bathroom Mid-Century Modern home boasting 3,600 total square feet of living space! Designed with classic MCM flair, the main level features a bright open-concept layout accented by soaring exposed beam ceilings and rich vertical wood siding that seamlessly blends natural warmth with sleek modern lines. The highlight of the home is the huge four-seasons sunroom stretching across the entire back of the house. Lined with windows, it offers a stunning vantage point over the lush, manicured backyard, complete with a basketball court, and scenic, clear views of the Ohio River during the winter months. Constructed with a solid all-brick exterior and offering ample space for both quiet living and vibrant entertaining, this architectural treasure perfectly balances timeless style with spacious comfort. Schedule your private walkthrough today!

306 Fairmount Drive, Madison

234 Hargan Drive, Madison
$239,900
3 Beds ⋅ 2 Baths ⋅ 2026010971 MLS ⋅ ACTIVE Status
NEW PRICE $239,900! Spacious, updated, and full of character, this Bedford stone home offers over 1,800 square feet of living space in Madison's established Highland Heights neighborhood. Situated on a corner lot near Anderson Elementary, shopping, dining, and everyday conveniences, this 3 bedroom, 1.5 bath home has more space than you might expect. Inside, you'll find a spacious living room with a decorative accent wall and a separate bonus room featuring a wood burning fireplace, perfect for a family room, home office, playroom, or hobby space. New vinyl plank flooring extends through the kitchen, dining room, laundry room, and hallway. Additional updates include a newer furnace, updated lighting, several replacement windows, a completely renovated half bath, and an updated full bath that keeps its vintage tile charm. The oversized laundry room provides plenty of additional storage and functionality. All kitchen appliances remain, and a new stainless steel side by side refrigerator will be installed prior to closing. The living room desk also remains. With its Bedford stone exterior, flexible living spaces, recent updates, and convenient Madison location, this home has plenty to offer at its new price.

234 Hargan Drive, Madison

308 E Third Street, Madison
$465,000
5 Beds ⋅ 4 Baths ⋅ 2026010293 MLS ⋅ ACTIVE Status
Outstanding Home in the heart of Downtown Madison and formerly used as a Bed and Breakfast! This home has a highly sought after primary suite, laundry, guest half bath, updated Kitchen and living areas ALL on the main floor! Upstairs there are large and inviting 4 bedrooms and 2 bathrooms for family or guests and a dry basement for utilities and extra storage. Outside you will find the rare off street parking for downtown, tool/toy barn with room for outdoor entertainment or future pool/garage! Electronic remote shades and mounted TVs all convey with home. The historic details have been preserved with loads of updates. Historic Madison has been titled yet another award for outstanding living! Golf Cart around town, enjoy all the music and art festivals throughout the year and cruise on the river at your leisure! Schedule a showing today! ***All photographs and details are NOT AI generated.

308 E Third Street, Madison

3339 N Shun Pike Road, Madison
$5,500
2026010176 MLS ⋅ ACTIVE Status
5,000 Sq. Ft. Pole Barn for Lease – Endless Possibilities! Looking for a versatile space for your business? This 5,000-square-foot pole barn is now available for lease and offers the flexibility to accommodate a variety of commercial and industrial uses. Ideal for light manufacturing, warehousing, distribution, contractor operations, storage, workshop space, or other business ventures, this property provides ample room to help your business grow. The open floor plan allows for easy customization to meet your operational needs, with plenty of space for equipment, inventory, and production. Whether you’re expanding an existing business or launching a new venture, this property offers the functionality and flexibility you’ve been searching for. Property Highlights: 5,000 sq. ft. of versatile space Ideal for light manufacturing, warehouse, or commercial use Open layout with endless configuration possibilities Ample space for equipment, inventory, and operations Excellent opportunity for growing businesses Contact us today for more information or to schedule a private tour of this outstanding commercial leasing opportunity!

3339 N Shun Pike Road, Madison

604 Mulberry Street, Madison
$465,000
2 Beds ⋅ 3 Baths ⋅ 202609984 MLS ⋅ ACTIVE Status
Stunning full transformation of a mid-1800s brick home in Madison’s Historic District. Nearly every component has been rebuilt while preserving original character, including exposed brick walls, restored historic doors, and refinished original poplar floors on the second level. Main floor features an urban-historic aesthetic with clean lines, coffered ceilings, shiplap fireplace wall, wide-plank flooring, and a bright kitchen with quartz counters, white cabinetry, stainless appliances, and large pantry. Rear wing includes built-ins, half bath, laundry room, and access to a cathedral-ceiling porch. Upstairs offers two master suites with designer baths and coffered ceilings. New staircases are stained to match original floors. Extensive structural upgrades: new first-floor framing, rebuilt rear addition with conditioned crawlspace, conditioned basement with wood-plank-look finish and speakeasy feel, new insulated slab, restored masonry, steel lintels, spray-foamed attic, new 200-amp service, plumbing, gas lines, HVAC, and on-demand water heater. A rare historic home rebuilt for modern living. Schedule your showing today!

604 Mulberry Street, Madison

605 Walnut Street, Madison
$244,998
2 Beds ⋅ 2 Baths ⋅ 202609995 MLS ⋅ ACTIVE Status
Positioned within walking distance to Downtown Amenities, this move-in-ready Federal-style residence presents a compelling opportunity to capitalize on ongoing neighborhood investment and appreciation. The home successfully balances historic character with thoughtful modern updates, offering both authenticity and functionality. Key features include main floor updated kitchen appliances, living room, fireplace, dining room area, and half bath. Tall Ceilings, and finished painted hardwood floors that create a bright, durable living environment. A notably spacious, dry cellar provides flexible-use space not found in comparable Madison properties, ideal for a bonus room, work out space, or a secret "Speak Easy" space. The upper-level has an additional living or lounge area, both bedrooms, and a full bathroom - Enhancing the home's versatility from Owner Occupied, to Bed & Breakfast! Lots of possibilities. Outside, a fully fenced backyard offers multiple seating and entertainment spaces, including the covered Patio, and complemented by a storage barn for added convenience.

605 Walnut Street, Madison

1344 Lockard Street, Madison
$319,900
3 Beds ⋅ 2 Baths ⋅ 202609939 MLS ⋅ ACTIVE Status
Charming 3 bedroom, 2 bath home tucked into a quiet neighborhood with updates already done for you. Enjoy peace of mind with a new roof and gutters with guards, plus new LVP flooring throughout for a stylish, low-maintenance feel. The kitchen features new quartz countertops and a bar area that opens seamlessly to the living room, creating an ideal layout for everyday living and entertaining, with vaulted ceilings adding an airy, spacious feel. A partial walk-out basement offers additional storage space and flexibility. Step outside to a large, fully fenced backyard with exceptional privacy—perfect for pets, play, or relaxing evenings. Move-in ready and easy to love. ** Take advantage of $5,000 in seller-paid concessions—use it toward closing costs, prepaid expenses, or reduce your monthly payment by buying down your interest rate (subject to lender approval).

1344 Lockard Street, Madison

4466 N SR 62, Madison
$759,900
7 Beds ⋅ 5 Baths ⋅ 202609873 MLS ⋅ ACTIVE Status
Excited to share details regarding this exceptional property situated on over 5 acres just on the edge of town. Located only 2 miles from the hub of Madison's hilltop and minutes from vibrant downtown Madison—recently rated the #1 Best Small Town in the Midwest by USA Today—this home offers an incredible amount of space and versatility. The interior features a gorgeous custom kitchen designed for entertaining, complemented by beautiful genuine hardwood floors throughout the main living area. The primary suite includes a modern soaking tub, tiled walk-in shower, and double vanities for ultimate comfort. The main level also offers 3 more bedrooms, a full bathroom, a half bath for guests, and a laundry room. Upstairs, you will find 2 large loft areas, 3 additional bedrooms, and a very spacious full bathroom. The full finished walk-out basement provides a very large Family room, a 2nd laundry room, ample storage, a play room, a safe room, and an additional full bathroom. Outdoor amenities are equally impressive, featuring large covered front and back porches with updated Trex flooring. The fenced backyard includes a playset and leads to 3 acres of wooded land. Additionally the property includes 2 detached garages: one is insulated, with rubber mat flooring across the entire floor, and has a heat & air system, while the 2nd features a 12-foot door perfect for an RV or boat. This dream home has so much to offer. Schedule your viewing today!

4466 N SR 62, Madison

118 Ferry Street, Madison
$479,900
3 Beds ⋅ 3 Baths ⋅ 202609731 MLS ⋅ ACTIVE Status
Located just one block from the Ohio Riverfront, this turnkey triplex investment property offers three updated rental units and multiple income streams through existing tenants and a proven AirBnB operation. Unit 1 and 2 feature comfortable one-bedroom layouts with full kitchens, living rooms, and baths, while Unit 3 offers a studio setup with a full bath. Each unit has been thoughtfully updated with luxury vinyl plank flooring, granite countertops, new cabinetry, and stainless-steel appliances within the last 4 years. Additional recent improvements include a newer roof (2023), newly paved patio (2023), new water heaters (Unit 2 & 3), and an added water softener, ensuring low-maintenance ownership for years to come. With off-street parking, attractive river views, and a location that puts residents within walking distance of the waterfront, this is an investment opportunity you won't want to miss!

118 Ferry Street, Madison

2037 Ridgewood Drive, Madison
$339,999
3 Beds ⋅ 2 Baths ⋅ 202609219 MLS ⋅ ACTIVE Status
Beautifully updated 3-bedroom, 2 full bath home located in the desirable Sunrise neighborhood and within walking distance of Sunrise Golf Course. This move-in ready home features a spacious kitchen complete with appliances, a large pantry, center island, and dining area—perfect for everyday living and entertaining. Generous-sized bedrooms offer walk-in closets, while an additional room provides the ideal space for a home office, hobby room, or flex space. Step outside to enjoy the large covered rear deck and patio overlooking the nice-sized backyard, complete with a raised garden bed and a storage shed. Thoughtfully updated throughout, this home combines modern conveniences with comfortable living in a great location. Don't miss this opportunity to own a beautifully redone home in one of the area's most sought-after neighborhoods!

2037 Ridgewood Drive, Madison

507 W Main Street, Madison
$564,900
4 Beds ⋅ 3 Baths ⋅ 202609257 MLS ⋅ ACTIVE Status
Historic Downtown Madison Gem with Main-Level Bedroom Potential & Full Bath! Experience the timeless beauty of the Classic Federal Historic John Boyd Home, circa 1834, offering over 3,200 square feet of character-filled living space in the heart of downtown Madison. Listed on the National Register of Historic Places, one of this home's most versatile features is an enclosed main-level room with a privacy door and convenient access to a full bathroom—ideal for use as a potential first-floor bedroom, guest room, or home office. The kitchen windows open and have screens for viewing the backyard, granite countertops, Mike Young soft close cabinetry, all the appliances which includes gas range and original fireplace. Utility room includes utility sink and additional cabinetry. With beautiful original architectural details, spacious entertaining areas, a private garden, and walkable access to downtown shops, restaurants, and the riverfront, this home combines historic charm with flexibility for modern living. The home showcases 6 fireplaces, original wide plank wood flooring, crown molding, chandeliers throughout, front and back staircases. Upgrades to electrical, plumbing and anti-mold protection system and sump pump in basement. Oversized one car garage with 10 x 14 covered and lighted patio. Additional off street parking is available behind the garage. Schedule your private showing and discover the possibilities!

507 W Main Street, Madison

887 vine Street, Madison
$127,000
202609125 MLS ⋅ ACTIVE Status
Rare opportunity to own an extra-large residential lot in downtown Madison! Tucked away on a quiet dead-end street with only four neighboring homes, this private setting offers a unique blend of seclusion and convenience. Mature trees provide abundant shade and natural beauty, while a small creek along the rear of the property adds to its charm. The lot is approved for a manufactured home, making it ready for your future plans. Located near Historic Springdale Cemetery and just minutes from Madison's vibrant downtown, you'll enjoy easy access by foot, bicycle, or golf cart to local shops, restaurants, entertainment, and the Ohio River waterfront. The surrounding neighborhood is experiencing ongoing revitalization, with many homes being remodeled and updated, making this an excellent opportunity to build or invest in one of Madison's growing areas. City approved building permit is available for a custom Baird 2 Bedroom/2 Bathroom house. Please note online imagery from Google Maps is incorrect. Street view is not of this property.

887 vine Street, Madison

307 Hillcrest Drive, Madison
$599,000
4 Beds ⋅ 5 Baths ⋅ 202609020 MLS ⋅ ACTIVE Status
Welcome to 307 Hillcrest Drive, an impressive 4-bedroom, 4.5-bath home offering 4,424 square feet of finished living space in one of Madison’s most desirable neighborhoods. Designed for both comfortable everyday living and entertaining, the home features a formal dining room, private office, spacious living areas, a sunroom, bonus room, recreation room, and an eat-in kitchen with a center island. The basement provides additional living and storage space and includes a full bathroom. Outside, enjoy more than half an acre of beautifully established grounds with mature trees and landscaping, a gazebo, patio, deck, and enclosed porch. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the two-car attached garage and separate two-car detached garage. With generous room sizes, abundant storage, timeless character, and inviting indoor and outdoor spaces, this exceptional Hillcrest property offers the space and versatility to truly make it your own.

307 Hillcrest Drive, Madison

316 W Main Street, Madison
$350,000
1 Beds ⋅ 1 Baths ⋅ 202609040 MLS ⋅ ACTIVE Status
Discover this Italianate two-part in a commercial block, constructed circa 1870, brimming with potential for various business ventures or investment opportunities! **Property Highlights** Spacious first floor - Enjoy approximately 3140 sq ft of versatile space, perfect for retail or office use. Flexible Second Floor - Currently utilized for storage, this level can easily be transformed to suit your needs, whether it be additional office space or even more retail opportunities. Third Floor Comfort - A welcoming apartment provides both convenience and potential rental income, making this property a smart investment. Property runs from Main Street to the back alley. Don't miss out on a chance to own this property! Contact us today for more information or schedule a viewing.

316 W Main Street, Madison

313-315 Mulberry Street, Madison
$515,000
12 Beds ⋅ 3 Baths ⋅ 202608867 MLS ⋅ ACTIVE Status
Exceptional investment opportunity in the heart of historic downtown Madison! These two contiguous buildings offer three stories featuring over 1700sqft of open retail space combined with a total of 12 bedrooms, 3 bathrooms, a main floor office, and dedicated laundry room space. Out your front door overlooks the area beside the iconic Kindness Mural and Bicentennial Park, with convenient golf cart parking, newly renovated public parking areas, and updated streetscapes just outside your door. Main level on 313 has large open room that could be used for multiple types of business. Located in the center of booming downtown Madison, you are only steps away from shopping, restaurants, festivals, riverfront attractions, and everything this charming historic town has to offer. Whether you are looking for long-term rentals, short-term rental potential, employee housing, or a mixed-use investment, the possibilities are endless. Rare opportunity to own a large footprint in one of Indiana’s most desirable downtown districts.

313-315 Mulberry Street, Madison

512 E Main Street Unit 1, Madison
$199,900
1 Beds ⋅ 1 Baths ⋅ 202608700 MLS ⋅ ACTIVE Status
Experience downtown living at its finest in this sunny first-floor condo located in a beautiful historic building on Main Street in Madison. Offering approximately 1,000 square feet, this charming condo features soaring 12-foot ceilings throughout, creating a bright and spacious atmosphere. The large one-bedroom, one-bath layout includes a walk-in shower, inviting family room with a fireplace, and a charming eat-in kitchen perfect for everyday living. Additional highlights include bonus exterior storage space, shared patio area, off-street parking, and several newer appliances. Conveniently located just steps from local shops, restaurants, wineries, popular festivals, and the scenic Ohio River, this condo offers the perfect blend of historic charm and downtown convenience. A must-see opportunity!

512 E Main Street Unit 1, Madison

931 W Main Street, Madison
$219,900
2 Beds ⋅ 2 Baths ⋅ 202608635 MLS ⋅ ACTIVE Status
Charming two-story home located in the heart of downtown Madison! This well-maintained property offers 2 bedrooms, 2 full baths, a spacious living room, cozy family room, large laundry room, separate dining area, and an inviting kitchen with plenty of space for everyday living. Enjoy relaxing on the covered front porch with Main Street views. Take advantage of alley access to the backyard with convenient off-street parking. Recent updates include a newer roof approximately 5 years old and Thermopane windows throughout. Just a short walk to downtown shops, local eateries, wineries, and the picturesque Ohio River waterfront, this home combines comfort, convenience, and small-town charm in an ideal location.

931 W Main Street, Madison

2904 N Rykers Ridge Road, Madison
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 202608456 MLS ⋅ ACTIVE Status
Welcome to an extraordinary property in the highly desirable Rykers Ridge area of Jefferson County, Indiana—where refined living meets breathtaking natural beauty. Situated on 57 pristine acres of rolling pasture & wooded acreage, this private retreat offers a rare combination of elegance, tranquility, & space. From the moment you arrive, the home’s timeless charm is evident in its inviting covered front porch & wraparound veranda—perfect for enjoying sweeping views & peaceful surroundings. Designed for both relaxation & entertaining, the outdoor spaces include a covered back porch & patio, all immersed in a serene landscape rich with wildlife. Inside, impeccable craftsmanship shines through with high ceilings, exquisite cabinetry, & two striking fireplaces that anchor the home’s sophisticated living spaces. The residence features two beautifully appointed kitchens, ideal for seamless multi-generational living or hosting guests in style with dedicated private quarters. Offering 4 spacious bedrooms & 2 spa-inspired bathrooms, every detail has been curated to provide comfort & luxury. A detached two-car garage with lean-to & a barn add both function & versatility to this remarkable property. Located just minutes from the charm & culture of Madison, Indiana, this estate delivers an unparalleled lifestyle of privacy, beauty, & elevated country living. If you’ve been dreaming of space, privacy, & a place to truly unwind—this Rykers Ridge property in Jefferson County is it.

2904 N Rykers Ridge Road, Madison

612B W Second Street Unit 4, Madison
$324,900
2 Beds ⋅ 3 Baths ⋅ 202608000 MLS ⋅ ACTIVE Status
Spacious, comfortable condominium in downtown Madison. Features tall ceilings, beautiful woodwork, and great natural light throughout. Cherry kitchen cabinets, granite counter top, all appliances, and breakfast bar. Large main suite with oversized window overlooking gardens and rooftops. Main suite includes well designed walk-in closet. Besides the main suite bath additional full bath and half bath off the second bedroom. Fireplaces are decorative. Beautiful staircase in common area with landing at this unit and additional back staircase. Large front porch for residence use. Front and back staircase. One car garage space with storage. Great location blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today's Best Small Town in the Midwest"--has to offer.

612B W Second Street Unit 4, Madison

225 E Main Street, Madison
$275,000
202608094 MLS ⋅ ACTIVE Status
Located in the heart of downtown Madison on Main Street, this versatile three-story building offers 2,745 sq ft and endless possibilities. The main floor is currently operating as a t-shirt shop, but the space could easily accommodate a variety of retail, office, or service-based businesses. The upper floors provide excellent rental or residential potential. The second floor offers additional usable space, while the third floor is unfinished and ready for a buyer to customize to fit their needs. With the option to live and work in the same building or generate additional rental income, this property presents a unique investment opportunity. Situated on Main Street in Madison IN with high foot and vehicle traffic, you’ll be just steps away from popular restaurants, shops, wineries, and local attractions. A prime location with incredible potential in one of southern Indiana’s most charming historic downtowns.

225 E Main Street, Madison

How much is your home worth?

Get instant property value now!