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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!

3 Beds ⋅ 3 Baths ⋅ 202609731 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$170,000

Looking for a home with a fenced yard and a 2 car garage? This 2 bedroom, 1 bath home on Madison’s hilltop has both. Enjoy a backyard with room for pets, gardening, or evenings outside, plus a detached garage with plenty of space for parking and storage. The location keeps you close to shopping, dining, and everything Madison’s hilltop has to offer. Come take a look and see how you could make this home your own.

2 Beds ⋅ 1 Baths ⋅ 202609418 MLS

Looking for a home with a fenced yard and a 2 car garage? This 2 bedroom, 1 bath home on Madison’s hilltop has both. Enjoy a backyard with room for pets, gardening, or evenings outside, plus a detached garage with plenty of space for parking and storage. The location keeps you close to shopping, dining, and everything Madison’s hilltop has to offer. Come take a look and see how you could make this home your own.

2510 Franks Drive, Madison

Listing courtesy of eXp Realty, LLC.

$324,900

Welcome to this charming Country Estate home offering comfort, quality, and plenty of character. Situated on a beautiful corner lot in a desirable neighborhood, this 3-bedroom, 2.5-bath home features a covered front porch, attached two-car garage, and a durable metal roof. The inviting kitchen showcases quartz countertops, a stylish sink, and thoughtful finishes throughout. Enjoy cozy evenings by the wood stove with custom ceramic surround, while the high-efficiency heat pump provides year-round comfort. A wonderful blend of peaceful country living and modern conveniences awaits! Call for your showing today!

3 Beds ⋅ 3 Baths ⋅ 202609422 MLS

Welcome to this charming Country Estate home offering comfort, quality, and plenty of character. Situated on a beautiful corner lot in a desirable neighborhood, this 3-bedroom, 2.5-bath home features a covered front porch, attached two-car garage, and a durable metal roof. The inviting kitchen showcases quartz countertops, a stylish sink, and thoughtful finishes throughout. Enjoy cozy evenings by the wood stove with custom ceramic surround, while the high-efficiency heat pump provides year-round comfort. A wonderful blend of peaceful country living and modern conveniences awaits! Call for your showing today!

5260 W Quail Run Lane, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$329,900

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!

3 Beds ⋅ 2 Baths ⋅ 202609219 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$2,300,000

Almost 48 acres of prime real estate located on Madison Hilltop. Lots of potential uses. Land is currently being farmed. Call today!!

202609388 MLS

Almost 48 acres of prime real estate located on Madison Hilltop. Lots of potential uses. Land is currently being farmed. Call today!!

701 W Hutchinson Lane, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$189,900

TERRIFIC SECOND HOME OR WEEKEND PLACE IN HISTORIC DOWNTOWN MADISON,IN. FORMERLY COZY COTTAGE AIR B&B. CLOSE TO THE HERITAGE TRAIL, DOWNTOWN SHOPPING, CLIFTY FALLS STATE PARK OR THE OHIO RIVER FRONT. GREAT OPPORTUNITY! SUBJECT TO SELLER CLOSING ON A SPECIFIC HOME THAT THEY CURRENTLY HAVE AN ACCEPTED OFFER. SELLERS ARE LEAVING MUCH OF THE PERSONAL PROPERTY BUT PLESASE SEE ATTACHMENT WITH THAT LIST. WALL HEATER IN BA NOT WORKING.

2 Beds ⋅ 1 Baths ⋅ 202609317 MLS

TERRIFIC SECOND HOME OR WEEKEND PLACE IN HISTORIC DOWNTOWN MADISON,IN. FORMERLY COZY COTTAGE AIR B&B. CLOSE TO THE HERITAGE TRAIL, DOWNTOWN SHOPPING, CLIFTY FALLS STATE PARK OR THE OHIO RIVER FRONT. GREAT OPPORTUNITY! SUBJECT TO SELLER CLOSING ON A SPECIFIC HOME THAT THEY CURRENTLY HAVE AN ACCEPTED OFFER. SELLERS ARE LEAVING MUCH OF THE PERSONAL PROPERTY BUT PLESASE SEE ATTACHMENT WITH THAT LIST. WALL HEATER IN BA NOT WORKING.

1041 W MAIN Street, Madison

Listing courtesy of Real Estate Inc.

$459,000

If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

1 Beds ⋅ 1 Baths ⋅ 1720413 MLS

If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

2945 N Greenbrier Rd, Madison

Listing courtesy of Trueblood Real Estate.

$127,000

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.

202609125 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$599,000

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.

4 Beds ⋅ 5 Baths ⋅ 202609020 MLS

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

Listing courtesy of Legacy Land Use & Realty.

$350,000

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.

1 Beds ⋅ 1 Baths ⋅ 202609040 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$515,000

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.

12 Beds ⋅ 3 Baths ⋅ 202608867 MLS

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

Listing courtesy of Coldwell Banker Harrell & Asso.

$199,900

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!

1 Beds ⋅ 1 Baths ⋅ 202608700 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$219,900

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.

2 Beds ⋅ 2 Baths ⋅ 202608635 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$1,100,000

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.

4 Beds ⋅ 2 Baths ⋅ 202608456 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$49,000

Prime vacant lot in highly sought-after neighborhood. This lot offers the perfect canvas to build your dream home, nestled among beautifully designated residences in a vibrant and established community. With a cul-de-sac location, this property provides both privacy and convenience. Enjoy easy access to historic and award-winning downtown Madison. Schedule your showing today!

202608287 MLS

Prime vacant lot in highly sought-after neighborhood. This lot offers the perfect canvas to build your dream home, nestled among beautifully designated residences in a vibrant and established community. With a cul-de-sac location, this property provides both privacy and convenience. Enjoy easy access to historic and award-winning downtown Madison. Schedule your showing today!

581 S Indian Cave Road, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$300,000

You don't want to miss this beautifully updated 3 bedroom, 2 bath home offering over 1500 sq. ft. in a quiet cul-de-sac just minutes from town. Recent upgrades include new West Shore doors and windows, new flooring, new carpet, and fresh paint throughout. The kitchen also features new appliances! The roof is less than 2 years old and it has a brand new sump pump. Inside you'll love the spacious feel created by both tray and vaulted ceilings. The perfect blend of comfort, style, and convenience!

3 Beds ⋅ 2 Baths ⋅ 202608313 MLS

You don't want to miss this beautifully updated 3 bedroom, 2 bath home offering over 1500 sq. ft. in a quiet cul-de-sac just minutes from town. Recent upgrades include new West Shore doors and windows, new flooring, new carpet, and fresh paint throughout. The kitchen also features new appliances! The roof is less than 2 years old and it has a brand new sump pump. Inside you'll love the spacious feel created by both tray and vaulted ceilings. The perfect blend of comfort, style, and convenience!

401 Maple Hill Drive, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$324,900

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.

2 Beds ⋅ 3 Baths ⋅ 202608000 MLS

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

Listing courtesy of Century 21 River Valley.

$275,000

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.

202608094 MLS

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

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$139,900

Rare opportunity to own a beautiful 10 acre buildable lot in one of the area’s most desirable locations. Enjoy the peace and privacy of country living while being just minutes from town conveniences, shopping, dining, and schools. This property offers city water and city sewer access, making it ready for your dream home. Plenty of space for a custom build, gardens, workshop, or recreational use. A perfect blend of rural charm and modern convenience. Taxes currently reflect the full 30 acre parcel and will be adjusted accordingly for each individual 10 acre parcel. Soybeans have been planted for the 2026 season; seller will retain all rights to the 2026 crops.

202607751 MLS

Rare opportunity to own a beautiful 10 acre buildable lot in one of the area’s most desirable locations. Enjoy the peace and privacy of country living while being just minutes from town conveniences, shopping, dining, and schools. This property offers city water and city sewer access, making it ready for your dream home. Plenty of space for a custom build, gardens, workshop, or recreational use. A perfect blend of rural charm and modern convenience. Taxes currently reflect the full 30 acre parcel and will be adjusted accordingly for each individual 10 acre parcel. Soybeans have been planted for the 2026 season; seller will retain all rights to the 2026 crops.

2000+ E Cross Road Unit Lot 1, Madison

Listing courtesy of eXp Realty, LLC.

$324,900

Beautiful first floor Federal style condominium 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. Amazing remodeled kitchen boasts all major appliances, granite counter top, track lighting, under-cabinet lighting and plenty of counter space. Open floor plan with 10 ft ceilings, crown molding, recess lighting, chandeliers, hardwood flooring in foyer, living room and kitchen. Split bedrooms with owner using third bedroom as a sitting room. Owners suite has large dressing closet with additional vanity and built in desk. Large front porch for residence use. Small patio for owners use. One car garage space with storage and easy access from the condo. Don't let this move-in ready maintenance-free home pass you by.

3 Beds ⋅ 2 Baths ⋅ 202607581 MLS

Beautiful first floor Federal style condominium 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. Amazing remodeled kitchen boasts all major appliances, granite counter top, track lighting, under-cabinet lighting and plenty of counter space. Open floor plan with 10 ft ceilings, crown molding, recess lighting, chandeliers, hardwood flooring in foyer, living room and kitchen. Split bedrooms with owner using third bedroom as a sitting room. Owners suite has large dressing closet with additional vanity and built in desk. Large front porch for residence use. Small patio for owners use. One car garage space with storage and easy access from the condo. Don't let this move-in ready maintenance-free home pass you by.

610A W Second Street Unit 1, Madison

Listing courtesy of Century 21 River Valley.

$464,500

Completely remodeled and thoughtfully designed, this stunning 4-bedroom, 3.5-bath home offers 2,544 sq ft of beautifully updated living space in the heart of downtown Madison. Blending modern updates with timeless character, you’ll find exposed brick, wood beams, and quality craftsmanship throughout. The spacious kitchen features abundant cabinetry, a pantry, large island, and an attached dining area—perfect for everyday living and entertaining. The primary suite offers a generous layout with a large bath, and large closet. while natural light fills the home, creating a warm and inviting atmosphere, you wont want to miss what outside has to offer! Enjoy a private courtyard ideal for relaxing or outdoor dining, which leads to a detached two-car garage for added convenience and storage. Located just moments from shops, dining, wineries, and all that downtown Madison has to offer, this home is truly a must-see.

4 Beds ⋅ 4 Baths ⋅ 202607755 MLS

Completely remodeled and thoughtfully designed, this stunning 4-bedroom, 3.5-bath home offers 2,544 sq ft of beautifully updated living space in the heart of downtown Madison. Blending modern updates with timeless character, you’ll find exposed brick, wood beams, and quality craftsmanship throughout. The spacious kitchen features abundant cabinetry, a pantry, large island, and an attached dining area—perfect for everyday living and entertaining. The primary suite offers a generous layout with a large bath, and large closet. while natural light fills the home, creating a warm and inviting atmosphere, you wont want to miss what outside has to offer! Enjoy a private courtyard ideal for relaxing or outdoor dining, which leads to a detached two-car garage for added convenience and storage. Located just moments from shops, dining, wineries, and all that downtown Madison has to offer, this home is truly a must-see.

422 St Michaels Avenue, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$1,375,000

Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you're just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana's most sought after river towns.

10 Beds ⋅ 8 Baths ⋅ 1713737 MLS

Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you're just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana's most sought after river towns.

513 & 515 West St, Madison

Listing courtesy of EXP Realty LLC.

$1,375,000

Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you’re just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana’s most sought after river towns. $124,000 in gross income in the first full year of operation.

10 Beds ⋅ 8 Baths ⋅ 202607078 MLS

Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you’re just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana’s most sought after river towns. $124,000 in gross income in the first full year of operation.

513 & 515 West Street, Madison

Listing courtesy of eXp Realty, LLC.

$35,000

One bedroom, one bath, wood frame structure on the property. Assessor information shows 495 Sq ft. Property is inhabitable, but possibilities of a Pace Grant. Sold "As Is"

202606516 MLS

One bedroom, one bath, wood frame structure on the property. Assessor information shows 495 Sq ft. Property is inhabitable, but possibilities of a Pace Grant. Sold "As Is"

801 Gerry Lane, Madison

Listing courtesy of Century 21 River Valley.

2256 N Brooksburg Manville Road, Madison

$494,900

Discover the possibilities with this stunning 101.54-acre property offering the perfect blend of privacy, recreation, and potential. Mostly wooded with some tillable ground, this diverse tract stretches down to the creek, creating a beautiful natural setting and attracting abundant wildlife. Previously used for hunting and camping, this land is ideal for outdoor enthusiasts looking for their own private getaway. Whether you envision a recreational retreat, hunting property, weekend camping spot, or building your country dream home tucked away in nature, the opportunities here are endless. Peaceful, private, and full of potential—make this acreage your own.

202606336 MLS

Discover the possibilities with this stunning 101.54-acre property offering the perfect blend of privacy, recreation, and potential. Mostly wooded with some tillable ground, this diverse tract stretches down to the creek, creating a beautiful natural setting and attracting abundant wildlife. Previously used for hunting and camping, this land is ideal for outdoor enthusiasts looking for their own private getaway. Whether you envision a recreational retreat, hunting property, weekend camping spot, or building your country dream home tucked away in nature, the opportunities here are endless. Peaceful, private, and full of potential—make this acreage your own.

2256 N Brooksburg Manville Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$459,000

If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

1 Beds ⋅ 1 Baths ⋅ 202605428 MLS

If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

2945 N Greenbrier Road, Madison

Listing courtesy of Trueblood Real Estate.

$114,900

Open to interpretation!! How shall this property be finished? The preservation organization succeeded in stabilizing and beatifying its original footprint! This cottage needs to be made cozy by an individual ready to give it its layout and design. There are preservation covenants, held by Indiana Landmarks, with this property.

2025012675 MLS

Open to interpretation!! How shall this property be finished? The preservation organization succeeded in stabilizing and beatifying its original footprint! This cottage needs to be made cozy by an individual ready to give it its layout and design. There are preservation covenants, held by Indiana Landmarks, with this property.

707 Walnut Street, Madison

Listing courtesy of Legacy Land Use & Realty.

$250,000

Motivated Seller...added NEW Privacy Fence, NEW Bedroom Windows and don't miss the River View from Front Porch! Check out this charming and fully renovated home with a new rear addition, covered patio and garage in Downtown Historic Madison, Indiana! A traditional Shotgun home converted into more functional living style with solid wood floors, full tile bath and half bath, new kitchen with granite counters and a great courtyard-outdoor living area between the home and garage. This home has all new Roof, HVAC, Water Heater and Stainless Appliances. AND great location to Marina and less than a block walking distance to the Heritage Trail and Connector to Clifty State Park! Schedule a showing today!

2 Beds ⋅ 2 Baths ⋅ 2025012327 MLS

Motivated Seller...added NEW Privacy Fence, NEW Bedroom Windows and don't miss the River View from Front Porch! Check out this charming and fully renovated home with a new rear addition, covered patio and garage in Downtown Historic Madison, Indiana! A traditional Shotgun home converted into more functional living style with solid wood floors, full tile bath and half bath, new kitchen with granite counters and a great courtyard-outdoor living area between the home and garage. This home has all new Roof, HVAC, Water Heater and Stainless Appliances. AND great location to Marina and less than a block walking distance to the Heritage Trail and Connector to Clifty State Park! Schedule a showing today!

1122 W Second Street, Madison

Listing courtesy of eXp Realty, LLC.

$110,000

High traffic, commercial location on Madison's hilltop. All city utilities available. Zoned General Business. One parcel.

202505225 MLS

High traffic, commercial location on Madison's hilltop. All city utilities available. Zoned General Business. One parcel.

606 Green Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$105,000

Wooded lots now available at the corner of Borcherding and Deputy Pike to build your dream home. Water and electricity are available at the front of the lot; septic approved. Lot 13

2024010731 MLS

Wooded lots now available at the corner of Borcherding and Deputy Pike to build your dream home. Water and electricity are available at the front of the lot; septic approved. Lot 13

2561 W Borcherding Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

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