$319,900 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). 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
$759,900 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! 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
$479,900 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 ⋅ 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
$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 ⋅ ACTIVE Status 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
$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 ⋅ ACTIVE Status 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
$339,999 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 ⋅ 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
$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 ⋅ ACTIVE Status 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
$564,900 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! 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
$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 ⋅ 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
$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 ⋅ 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
$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 ⋅ 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
$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 ⋅ 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
$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 ⋅ 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
$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 ⋅ 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
$310,000 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 ⋅ ACTIVE Status 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
$649,000 Check out this truly rare opportunity in Madison, where you can enjoy the convenience of being just minutes from town while owning over 6 acres of private, picturesque land. Properties like this are hard to find, offering the accessibility and peaceful country living. This stunning home lives up to the hype with beauty, quality, space, and a sense of tranquility that’s hard to match. Inside, you’ll find beautiful living space filled with custom finishes and intricate detailing. From crown molding and unique ceilings with ambient lighting to the impressive fireplace, every element has been thoughtfully designed to impress. The versatile floor plan offers flexibility to fit your lifestyle, with options for a first-floor bedroom or office, and additional rooms upstairs that could serve as a nursery or sitting area. Entertaining is a breeze with a formal dining room, breakfast nook, and open-concept main living areas that flow seamlessly together. In addition to the attached 2+ car garage, a detached 2-car pole barn provides ample storage for vehicles, hobbies, or recreational equipment. If you're seeking privacy, high-quality finishes, and room to roam—all while staying close to town—this exceptional property is truly a must-see. 4 Beds ⋅ 3 Baths ⋅ 202607868 MLS ⋅ ACTIVE Status Check out this truly rare opportunity in Madison, where you can enjoy the convenience of being just minutes from town while owning over 6 acres of private, picturesque land. Properties like this are hard to find, offering the accessibility and peaceful country living. This stunning home lives up to the hype with beauty, quality, space, and a sense of tranquility that’s hard to match. Inside, you’ll find beautiful living space filled with custom finishes and intricate detailing. From crown molding and unique ceilings with ambient lighting to the impressive fireplace, every element has been thoughtfully designed to impress. The versatile floor plan offers flexibility to fit your lifestyle, with options for a first-floor bedroom or office, and additional rooms upstairs that could serve as a nursery or sitting area. Entertaining is a breeze with a formal dining room, breakfast nook, and open-concept main living areas that flow seamlessly together. In addition to the attached 2+ car garage, a detached 2-car pole barn provides ample storage for vehicles, hobbies, or recreational equipment. If you're seeking privacy, high-quality finishes, and room to roam—all while staying close to town—this exceptional property is truly a must-see. 4502 N SR 7, Madison
$265,000 Modern Luxury Meets Historic Convenience! This fully remodeled home offers a "brand new" living experience in the heart of downtown Madison. Interior Reinvention: The floor plan was strategically reconfigured to embrace a modern, open-concept layout. By merging the kitchen, dining, and living areas, the home now feels significantly more expansive and fluid. Complete Overhaul: Brand new roof, HVAC, double pane windows, and upgraded systems to include washer/dryer hookup. Privacy: A newly installed privacy fence secures the backyard, creating a dedicated, quiet sanctuary for outdoor living. Storage Galore: Multiple large closets throughout—rare for the area! Layout: 3 spacious bedrooms with primary suite on 1st floor and 2 full baths with modern finishes. Move-In Ready: Open layout perfect for entertaining or everyday living. Don't miss this opportunity to own a high-quality, low-maintenance home steps away from shopping, dining, and the Ohio River! -- Also, off-street parking perfect for golf cart/car!! 3 Beds ⋅ 2 Baths ⋅ 202607860 MLS ⋅ ACTIVE Status Modern Luxury Meets Historic Convenience! This fully remodeled home offers a "brand new" living experience in the heart of downtown Madison. Interior Reinvention: The floor plan was strategically reconfigured to embrace a modern, open-concept layout. By merging the kitchen, dining, and living areas, the home now feels significantly more expansive and fluid. Complete Overhaul: Brand new roof, HVAC, double pane windows, and upgraded systems to include washer/dryer hookup. Privacy: A newly installed privacy fence secures the backyard, creating a dedicated, quiet sanctuary for outdoor living. Storage Galore: Multiple large closets throughout—rare for the area! Layout: 3 spacious bedrooms with primary suite on 1st floor and 2 full baths with modern finishes. Move-In Ready: Open layout perfect for entertaining or everyday living. Don't miss this opportunity to own a high-quality, low-maintenance home steps away from shopping, dining, and the Ohio River! -- Also, off-street parking perfect for golf cart/car!! 423 Mill Street, Madison
$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 ⋅ ACTIVE Status 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
$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 ⋅ ACTIVE Status 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
$379,000 Historic Federal style home built in 1850 in the heart of historic downtown Madison. Step into a beautifully maintained home by its owners. You will be welcomed by a open staircase, sunny living, and dining rooms with original, restored pine floors. Living room features the orginal fireplace (now decorative) and leaded glass hangings in the front windows. Large kitchen is highlighted with vintage General Electric steel kitchen cabinets in amazing condition. Granite counter top and tile back-splash. The unique kitchen floor is plank eucalyptus. The rear project/utility/garden room has a large storage closet and big picture window looking at the landscaped and peaceful fenced yard and patio. Covered back door entrance. Three spacious bedrooms. Second and third bedrooms currently used by the homeowners as TV/reading room and office. Completely remodeled baths (full and half) with tile flooring, shower, refinished claw-foot tub and stainglass window hangings in the full bathroom. Home is located close to dining, shopping, riverfront, festivals and all that Madison---USA Today's "Best Small Town in the Midwest"--has to offer. 3 Beds ⋅ 2 Baths ⋅ 202606645 MLS ⋅ ACTIVE Status Historic Federal style home built in 1850 in the heart of historic downtown Madison. Step into a beautifully maintained home by its owners. You will be welcomed by a open staircase, sunny living, and dining rooms with original, restored pine floors. Living room features the orginal fireplace (now decorative) and leaded glass hangings in the front windows. Large kitchen is highlighted with vintage General Electric steel kitchen cabinets in amazing condition. Granite counter top and tile back-splash. The unique kitchen floor is plank eucalyptus. The rear project/utility/garden room has a large storage closet and big picture window looking at the landscaped and peaceful fenced yard and patio. Covered back door entrance. Three spacious bedrooms. Second and third bedrooms currently used by the homeowners as TV/reading room and office. Completely remodeled baths (full and half) with tile flooring, shower, refinished claw-foot tub and stainglass window hangings in the full bathroom. Home is located close to dining, shopping, riverfront, festivals and all that Madison---USA Today's "Best Small Town in the Midwest"--has to offer. 507 E Main Street, Madison
$376,900 Scenic river view and comfortable downtown living in this two year old home. This two bedroom, two bath residence provides a designer kitchen with breakfast bar, granite counter top and tile backsplash. Open concept living and dining area with open staircase to basement. River view from living and dining areas. Large family room walk-out to covered patio and river view. Have your morning coffee or evening beverage with view of the sun shinging on the river or the sunset over the bridge. Home is located close to river walk, riverfront parks, dining, shopping, festivals and all that Madison---USA Todays's "Best Small Town in the Midwest"--has to offer. 2 Beds ⋅ 2 Baths ⋅ 202606763 MLS ⋅ ACTIVE Status Scenic river view and comfortable downtown living in this two year old home. This two bedroom, two bath residence provides a designer kitchen with breakfast bar, granite counter top and tile backsplash. Open concept living and dining area with open staircase to basement. River view from living and dining areas. Large family room walk-out to covered patio and river view. Have your morning coffee or evening beverage with view of the sun shinging on the river or the sunset over the bridge. Home is located close to river walk, riverfront parks, dining, shopping, festivals and all that Madison---USA Todays's "Best Small Town in the Midwest"--has to offer. 1010 E First Street, Madison
$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 ⋅ ACTIVE Status 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
$219,000 Charming and newly renovated home with fresh paint, updated flooring, and a sleek modern kitchen offers the perfect blend of comfort and functionality. The home offers 2 BD/2BA and a bonus room upstairs that can be a 3rd BD with spacious storage. The unfinished basement offers excellent potential for additional living space, making this home a fantastic opportunity with room to grow. This home blends comfort, character, and convenience in a great location on the hilltop. Schedule your showing today. 2 Beds ⋅ 2 Baths ⋅ 2025013009 MLS ⋅ ACTIVE Status Charming and newly renovated home with fresh paint, updated flooring, and a sleek modern kitchen offers the perfect blend of comfort and functionality. The home offers 2 BD/2BA and a bonus room upstairs that can be a 3rd BD with spacious storage. The unfinished basement offers excellent potential for additional living space, making this home a fantastic opportunity with room to grow. This home blends comfort, character, and convenience in a great location on the hilltop. Schedule your showing today. 2159 Lanier Drive, Madison
$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 ⋅ ACTIVE Status 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
$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 ⋅ ACTIVE Status 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
$454,900 So many possibilities await you with this lovingly maintained home on over 1 1/2 acres with mature trees and a parklike setting with a decorative pond. This home offers 3 bedrooms, 2 full baths, one with a jetted tub and heated tile floor, living room with a gas fireplace, eat in kitchen with a pantry and granite counter tops, family room with a brick hearth and flue for a wood stove and a utility room in the main living quarters. In addition to the main living area, there is an attached living quarters/guest suite with a kitchen, full bathroom, 2 bedrooms, a living room/play room and it's own front entry and rear entry with a deck. Wait that isn't all! There are front and rear keyless entries on main living quarters doors, 2 - 2+ car detached garages, a blacktop drive with extras parking, a nice back patio and a 24' above ground pool with a deck. This home is conveniently located within 4 miles of Madison's hilltop area and Clifty Falls State Park, within 4.5 miles from Hanover and within 5 miles of Madison's historic downtown area that was named the #1 Small Town in the Midwest by USA Today 10 Best Readers' Choice Award for 2024. Potted plants will be taken by Seller and some starts off of some perennials will be take by the seller. New Survey Attached. New w/s installed July 2025 also new elements in water heater. All new paint June-July 2026 in the living room, kitchen, hallway, 1 bedroom and 1 bathroom. Mantel @ fireplace will not convey. 5 Beds ⋅ 3 Baths ⋅ 202409255 MLS ⋅ ACTIVE Status So many possibilities await you with this lovingly maintained home on over 1 1/2 acres with mature trees and a parklike setting with a decorative pond. This home offers 3 bedrooms, 2 full baths, one with a jetted tub and heated tile floor, living room with a gas fireplace, eat in kitchen with a pantry and granite counter tops, family room with a brick hearth and flue for a wood stove and a utility room in the main living quarters. In addition to the main living area, there is an attached living quarters/guest suite with a kitchen, full bathroom, 2 bedrooms, a living room/play room and it's own front entry and rear entry with a deck. Wait that isn't all! There are front and rear keyless entries on main living quarters doors, 2 - 2+ car detached garages, a blacktop drive with extras parking, a nice back patio and a 24' above ground pool with a deck. This home is conveniently located within 4 miles of Madison's hilltop area and Clifty Falls State Park, within 4.5 miles from Hanover and within 5 miles of Madison's historic downtown area that was named the #1 Small Town in the Midwest by USA Today 10 Best Readers' Choice Award for 2024. Potted plants will be taken by Seller and some starts off of some perennials will be take by the seller. New Survey Attached. New w/s installed July 2025 also new elements in water heater. All new paint June-July 2026 in the living room, kitchen, hallway, 1 bedroom and 1 bathroom. Mantel @ fireplace will not convey. 317 Meadow Lane, Madison