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Built in 2022, this all-brick townhome offers a rare opportunity to enjoy historic downtown Madison living without any of the headaches or upkeep of an older home. Set right along the Ohio River, the residence blends classic riverfront charm with modern, turnkey luxury. Inside, the open layout is built for effortless living and entertaining, featuring rich hardwood floors, custom finishes, and a chef's kitchen outfitted with Bosch stainless steel appliances. A private elevator currently services the first two floors and is fully prepped to be extended to the third level if desired. Another major downtown standout is the oversized two-car attached garage paired with dedicated off-street parking, taking the stress out of coming and going. The outdoor spaces are designed to let you enjoy the fresh air and scenic river views all year round. Spend crisp mornings on the private deck or unwind on the spacious screened-in porch without worrying about bugs or passing weather. Just outside your front door, you are steps away from Madison's best local dining, boutique shops, the riverfront walkway, and year-round festivals. Whether you are looking for a full-time residence or a worry-free weekend retreat, 819 W First Street delivers modern comfort and convenience in the heart of downtown.

3 Beds ⋅ 4 Baths ⋅ 2026013216 MLS

Built in 2022, this all-brick townhome offers a rare opportunity to enjoy historic downtown Madison living without any of the headaches or upkeep of an older home. Set right along the Ohio River, the residence blends classic riverfront charm with modern, turnkey luxury. Inside, the open layout is built for effortless living and entertaining, featuring rich hardwood floors, custom finishes, and a chef's kitchen outfitted with Bosch stainless steel appliances. A private elevator currently services the first two floors and is fully prepped to be extended to the third level if desired. Another major downtown standout is the oversized two-car attached garage paired with dedicated off-street parking, taking the stress out of coming and going. The outdoor spaces are designed to let you enjoy the fresh air and scenic river views all year round. Spend crisp mornings on the private deck or unwind on the spacious screened-in porch without worrying about bugs or passing weather. Just outside your front door, you are steps away from Madison's best local dining, boutique shops, the riverfront walkway, and year-round festivals. Whether you are looking for a full-time residence or a worry-free weekend retreat, 819 W First Street delivers modern comfort and convenience in the heart of downtown.

819 W 1st Street, Madison

Listing courtesy of Legacy Land Use & Realty.

$595,000

Welcome to the Historic Maddox House! A stunning example of Italianate architecture, this elegant two-story, all-brick residence is ideally situated on Main Street in the heart of historic downtown Madison. Rich in character and timeless charm, this beautifully maintained home offers an exceptional blend of historic elegance, modern comfort, and versatility. Featuring FOUR private suites, the home boasts spacious living areas, beautiful interior finishes, and oversized windows that fill the rooms with natural light. Two of the suites offer private entrances with individual access codes and have previously been utilized as short-term rentals. Both will remain furnished, providing an excellent opportunity for potential income generation or private guest accommodations. Additional highlights include gas and electric options, multiple off-street parking spaces, a well-maintained oversized storage shed with ample room for a golf cart, and a clean, dry cellar housing the home’s utilities. Whether you’re searching for a spacious family residence, a historic downtown retreat, or a turnkey investment opportunity, the Maddox House offers incredible flexibility in one of Madison’s most desirable locations. Experience the charm, elegance, and convenience of Main Street living in this truly remarkable historic property!

4 Beds ⋅ 4 Baths ⋅ 2026013231 MLS

Welcome to the Historic Maddox House! A stunning example of Italianate architecture, this elegant two-story, all-brick residence is ideally situated on Main Street in the heart of historic downtown Madison. Rich in character and timeless charm, this beautifully maintained home offers an exceptional blend of historic elegance, modern comfort, and versatility. Featuring FOUR private suites, the home boasts spacious living areas, beautiful interior finishes, and oversized windows that fill the rooms with natural light. Two of the suites offer private entrances with individual access codes and have previously been utilized as short-term rentals. Both will remain furnished, providing an excellent opportunity for potential income generation or private guest accommodations. Additional highlights include gas and electric options, multiple off-street parking spaces, a well-maintained oversized storage shed with ample room for a golf cart, and a clean, dry cellar housing the home’s utilities. Whether you’re searching for a spacious family residence, a historic downtown retreat, or a turnkey investment opportunity, the Maddox House offers incredible flexibility in one of Madison’s most desirable locations. Experience the charm, elegance, and convenience of Main Street living in this truly remarkable historic property!

934 W Main Street, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$1,100,000

40-ACRE GENTLEMAN'S FARM JUST OFF MADISON'S HILLTOP! Enjoy the best of both worlds with this exceptional property offering a country setting just minutes from Madison's amenities. Situated on 40 acres, this spacious ranch-style home offers approximately 3,438 sq. ft. of living space, 3 bedrooms, and 3.5 baths. The large rear sunroom provides a wonderful place to relax and take in views of the beautiful 3-acre lake and surrounding property. The full basement offers additional living space, featuring two bedrooms, a full bath, a large recreation room, and ample storage. An attached 1-car garage and detached pole barn with concrete and gravel floors provide versatility for vehicles, equipment, hobbies, or a workshop. Approximately 30 acres of tillable ground offer opportunities for farming, recreation, or investment. With its scenic setting, impressive acreage, and potential for future development, this is a rare opportunity to own a versatile property in a highly desirable location just off Madison's Hilltop!

3 Beds ⋅ 4 Baths ⋅ 2026013146 MLS

40-ACRE GENTLEMAN'S FARM JUST OFF MADISON'S HILLTOP! Enjoy the best of both worlds with this exceptional property offering a country setting just minutes from Madison's amenities. Situated on 40 acres, this spacious ranch-style home offers approximately 3,438 sq. ft. of living space, 3 bedrooms, and 3.5 baths. The large rear sunroom provides a wonderful place to relax and take in views of the beautiful 3-acre lake and surrounding property. The full basement offers additional living space, featuring two bedrooms, a full bath, a large recreation room, and ample storage. An attached 1-car garage and detached pole barn with concrete and gravel floors provide versatility for vehicles, equipment, hobbies, or a workshop. Approximately 30 acres of tillable ground offer opportunities for farming, recreation, or investment. With its scenic setting, impressive acreage, and potential for future development, this is a rare opportunity to own a versatile property in a highly desirable location just off Madison's Hilltop!

3617 N Graham Road, Madison

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

$194,900

Very clean and well cared for home with many updates. New metal roof 2022. Heat Pump and C/A 2024. Shows beautifully. Great home to get started. Nice yard with large deck on back.

3 Beds ⋅ 1 Baths ⋅ 2026013204 MLS

Very clean and well cared for home with many updates. New metal roof 2022. Heat Pump and C/A 2024. Shows beautifully. Great home to get started. Nice yard with large deck on back.

3380 N QUAIL Drive, Madison

Listing courtesy of Real Estate Inc.

$179,900

Move-in ready and built for low-maintenance living! This 3-bed, 1-bath home features over 1,000 finished square feet, a functional floor plan, and major system upgrades—complete with a brand-new HVAC system and new water heater for peace of mind. Located on a quiet lot in Madison, this property offers incredible value. Don't wait—schedule a showing today!

3 Beds ⋅ 2 Baths ⋅ 2026013091 MLS

Move-in ready and built for low-maintenance living! This 3-bed, 1-bath home features over 1,000 finished square feet, a functional floor plan, and major system upgrades—complete with a brand-new HVAC system and new water heater for peace of mind. Located on a quiet lot in Madison, this property offers incredible value. Don't wait—schedule a showing today!

3335 N Quail Drive, Madison

Listing courtesy of RE/MAX FIRST.

$83,900

Corner lot. Great downtown location. In the Georgetown area (underground Railroad). Ornate fireplace, Natural Sunlight. Utility room ceiling has historic tin. Transom windows have been preserved. Much of the original trim work was preserved. Door between kitchen and utility room is in storage. Some of the original trim is available if wanted. Some door hinges are original to the house. A PACE grant has not be pursued on this property yet. Front porch is inviting relaxing.

1 Beds ⋅ 1 Baths ⋅ 2026013162 MLS

Corner lot. Great downtown location. In the Georgetown area (underground Railroad). Ornate fireplace, Natural Sunlight. Utility room ceiling has historic tin. Transom windows have been preserved. Much of the original trim work was preserved. Door between kitchen and utility room is in storage. Some of the original trim is available if wanted. Some door hinges are original to the house. A PACE grant has not be pursued on this property yet. Front porch is inviting relaxing.

622 Jefferson Street, Madison

Listing courtesy of ReaL Broker, LLC.

$379,900

Enjoy beautiful riverfront living in the heart of Downtown Madison! This spacious 3-bedroom, 2-full-bath condo offers 1,793 sq. ft. of comfortable living space with an inviting open-concept kitchen, dining, and living area, perfect for everyday living and entertaining. The desirable split-bedroom floor plan provides added privacy, while custom cherry cabinetry throughout adds warmth and timeless appeal. Step outside to your private balcony and take in the beautiful views of the Ohio River and marina. Additional features include soundproof insulation in the ceilings and walls, a sprinkler system, and a convenient one-car garage located on the first level. Enjoy the charm of downtown Madison, scenic river views, and the convenience of low-maintenance condo living in a wonderful riverfront location!

3 Beds ⋅ 2 Baths ⋅ 2026013054 MLS

Enjoy beautiful riverfront living in the heart of Downtown Madison! This spacious 3-bedroom, 2-full-bath condo offers 1,793 sq. ft. of comfortable living space with an inviting open-concept kitchen, dining, and living area, perfect for everyday living and entertaining. The desirable split-bedroom floor plan provides added privacy, while custom cherry cabinetry throughout adds warmth and timeless appeal. Step outside to your private balcony and take in the beautiful views of the Ohio River and marina. Additional features include soundproof insulation in the ceilings and walls, a sprinkler system, and a convenient one-car garage located on the first level. Enjoy the charm of downtown Madison, scenic river views, and the convenience of low-maintenance condo living in a wonderful riverfront location!

1213 Hatteras Way Unit 103, Madison

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

$219,000

Great fixer-upper opportunity just minutes from Madison! This one-story, wheelchair-accessible home offers approximately 2,650 sq. ft. of living space, 3 bedrooms, and 3 full baths on a beautiful 2.37-acre lot. The home features a cozy family room with a brick hearth ready for a wood-burning stove, along with a spacious living room, dining area, and kitchen offering an opportunity to create a space tailored to your style. The main bedroom features convenient access to a full bath, with two additional full baths providing added functionality. A sunroom with Thermopane windows offers a relaxing space and leads to an outdoor patio. The attached garage provides room for a workshop or hobby area. Outside, you'll find an impressive 75' x 40' barn with a 30' x 36' addition, along with 2 storage sheds. With its acreage, substantial outbuildings, and convenient location near Madison, this property offers plenty of possibilities!

3 Beds ⋅ 3 Baths ⋅ 2026013115 MLS

Great fixer-upper opportunity just minutes from Madison! This one-story, wheelchair-accessible home offers approximately 2,650 sq. ft. of living space, 3 bedrooms, and 3 full baths on a beautiful 2.37-acre lot. The home features a cozy family room with a brick hearth ready for a wood-burning stove, along with a spacious living room, dining area, and kitchen offering an opportunity to create a space tailored to your style. The main bedroom features convenient access to a full bath, with two additional full baths providing added functionality. A sunroom with Thermopane windows offers a relaxing space and leads to an outdoor patio. The attached garage provides room for a workshop or hobby area. Outside, you'll find an impressive 75' x 40' barn with a 30' x 36' addition, along with 2 storage sheds. With its acreage, substantial outbuildings, and convenient location near Madison, this property offers plenty of possibilities!

4606 W Sr 250, Madison

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

$950,000

PRIME LAND on Madison's Hilltop Commercial/Industrial Area. The almost 24 tillable acres are currently leased, but it's a great opportunity to take advantage of the increasing development of Madison's Railroad industry with railroad access dividing this property ready for industrial or commercial development. The Bedford stone home is currently rented. It has 3BD/1BA on a full basement. The large barn also has a current tenant leasing for storage. Property has a deeded 12' easement to Clifty Dr. as well as a 30' railroad easement. Seller prefers to sell as a whole, however will entertain offers to split.

2 Beds ⋅ 1 Baths ⋅ 2026013070 MLS

PRIME LAND on Madison's Hilltop Commercial/Industrial Area. The almost 24 tillable acres are currently leased, but it's a great opportunity to take advantage of the increasing development of Madison's Railroad industry with railroad access dividing this property ready for industrial or commercial development. The Bedford stone home is currently rented. It has 3BD/1BA on a full basement. The large barn also has a current tenant leasing for storage. Property has a deeded 12' easement to Clifty Dr. as well as a 30' railroad easement. Seller prefers to sell as a whole, however will entertain offers to split.

602 Clifty Drive, Madison

Listing courtesy of eXp Realty, LLC.

$329,900

Discover the charm of this beautifully updated 2-bedroom home offering 1,788 sq. ft. of inviting living space in the heart of Downtown Madison with beautiful slate roof! From the moment you enter, you'll appreciate the beautiful front entry featuring a staircase leading to the second floor, along with stunning exposed brick accents that add warmth, character, and timeless appeal. The exposed brick continues into the lovely kitchen, creating a unique blend of character and modern updates. Situated on a desirable corner lot, this home also offers a private side patio, perfect for enjoying a little outdoor relaxation. With 1.5 baths, thoughtful updates, and an unbeatable location within walking distance of downtown shops, restaurants, and local attractions, this home offers the perfect combination of character, comfort, and convenience. A wonderful opportunity to enjoy downtown living!

2 Beds ⋅ 2 Baths ⋅ 2026013049 MLS

Discover the charm of this beautifully updated 2-bedroom home offering 1,788 sq. ft. of inviting living space in the heart of Downtown Madison with beautiful slate roof! From the moment you enter, you'll appreciate the beautiful front entry featuring a staircase leading to the second floor, along with stunning exposed brick accents that add warmth, character, and timeless appeal. The exposed brick continues into the lovely kitchen, creating a unique blend of character and modern updates. Situated on a desirable corner lot, this home also offers a private side patio, perfect for enjoying a little outdoor relaxation. With 1.5 baths, thoughtful updates, and an unbeatable location within walking distance of downtown shops, restaurants, and local attractions, this home offers the perfect combination of character, comfort, and convenience. A wonderful opportunity to enjoy downtown living!

426 East Street, Madison

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

$419,900

Prime turnkey investment opportunity in the heart of historic downtown Madison! Extensively renovated in 2023, this low-maintenance 4-unit income property comes fully furnished and ready to perform from day one. Capitalizing on the high-demand traveling professional market, the property rents effortlessly to traveling nurses and corporate contractors with an established 90-day minimum lease structure. The building features an ideal layout with two units on the first floor and two on the second floor, all boasting brand-new 2023 shingles, fresh interior and exterior paint, completely remodeled interiors, and efficient PTAC heating and cooling systems. Cash flow is immediate and robust: Unit 1 generates $1,300/mo (utilities included), Unit 3 is occupied by a stable long-term tenant at $1,000/mo, and Units 2 and 4 are ready to lease at $1,300/mo each. An additional $100–$150/mo in passive income is generated by the common hallway coin-operated laundry. With a total potential gross income pushing $5,050+ per month and all furnishings included, this is the ultimate hands-off addition to your real estate portfolio and an amazing 11% cap rate! Schedule your showing today!

4 Beds ⋅ 4 Baths ⋅ 2026013030 MLS

Prime turnkey investment opportunity in the heart of historic downtown Madison! Extensively renovated in 2023, this low-maintenance 4-unit income property comes fully furnished and ready to perform from day one. Capitalizing on the high-demand traveling professional market, the property rents effortlessly to traveling nurses and corporate contractors with an established 90-day minimum lease structure. The building features an ideal layout with two units on the first floor and two on the second floor, all boasting brand-new 2023 shingles, fresh interior and exterior paint, completely remodeled interiors, and efficient PTAC heating and cooling systems. Cash flow is immediate and robust: Unit 1 generates $1,300/mo (utilities included), Unit 3 is occupied by a stable long-term tenant at $1,000/mo, and Units 2 and 4 are ready to lease at $1,300/mo each. An additional $100–$150/mo in passive income is generated by the common hallway coin-operated laundry. With a total potential gross income pushing $5,050+ per month and all furnishings included, this is the ultimate hands-off addition to your real estate portfolio and an amazing 11% cap rate! Schedule your showing today!

521 West Street, Madison

Listing courtesy of eXp Realty, LLC.

$330,000

Welcome home to this well-maintained brick ranch offering 1,620 sq. ft. of comfortable living space! Featuring 3 bedrooms, 2.5 baths, a spacious family room filled with natural light, and a large living room, this home offers a welcoming and functional layout. The 2-car garage features separate garage doors, along with a bonus storage area just off the garage for added convenience. Outside, enjoy a nice yard with mature trees in an established, desirable neighborhood. Conveniently located close to schools, shopping, dining, and all that Madison has to offer, this property is a wonderful opportunity to make a well-cared-for home your own!

3 Beds ⋅ 3 Baths ⋅ 2026012992 MLS

Welcome home to this well-maintained brick ranch offering 1,620 sq. ft. of comfortable living space! Featuring 3 bedrooms, 2.5 baths, a spacious family room filled with natural light, and a large living room, this home offers a welcoming and functional layout. The 2-car garage features separate garage doors, along with a bonus storage area just off the garage for added convenience. Outside, enjoy a nice yard with mature trees in an established, desirable neighborhood. Conveniently located close to schools, shopping, dining, and all that Madison has to offer, this property is a wonderful opportunity to make a well-cared-for home your own!

129 Elmhurst Drive, Madison

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

$249,900

Updated & Move-In Ready! Welcome to this stunning 3 BR / 2 BA, 1,362 sq ft home featuring brand-new flooring through the living room, bedrooms, and main bath. Enjoy an attached 2-car garage and a fantastic outdoor setup complete with a covered patio, fully fenced backyard, and storage shed. Perfect for entertaining or relaxing in private. Don't miss this one—schedule your tour today!

3 Beds ⋅ 2 Baths ⋅ 1733236 MLS

Updated & Move-In Ready! Welcome to this stunning 3 BR / 2 BA, 1,362 sq ft home featuring brand-new flooring through the living room, bedrooms, and main bath. Enjoy an attached 2-car garage and a fantastic outdoor setup complete with a covered patio, fully fenced backyard, and storage shed. Perfect for entertaining or relaxing in private. Don't miss this one—schedule your tour today!

1851 Locust St, Madison

Listing courtesy of EXP Realty LLC.

$249,900

Updated & Move-In Ready! Welcome to this stunning 3 BR / 2 BA, 1,362 sq ft home featuring brand-new flooring through the living room, bedrooms, and main bath. Enjoy an attached 2-car garage and a fantastic outdoor setup complete with a covered patio, fully fenced backyard, and storage shed. Perfect for entertaining or relaxing in private. Don't miss this one—schedule your tour today!

3 Beds ⋅ 2 Baths ⋅ 2026012908 MLS

Updated & Move-In Ready! Welcome to this stunning 3 BR / 2 BA, 1,362 sq ft home featuring brand-new flooring through the living room, bedrooms, and main bath. Enjoy an attached 2-car garage and a fantastic outdoor setup complete with a covered patio, fully fenced backyard, and storage shed. Perfect for entertaining or relaxing in private. Don't miss this one—schedule your tour today!

1851 Locust Street, Madison

Listing courtesy of eXp Realty, LLC.

$195,000

Convenient Location in Downtown Historic Madison! Previous rental, ready to remodel and use your imagination- Make it a residence, Airbnb, long term rental or even a business! Open floor plan with 1/2 bath on main level with 2-3 bedrooms/offices and full bathroom upstairs. Small backyard - just enough for a patio or fenced in area. Selling As Is.

3 Beds ⋅ 2 Baths ⋅ 2026012829 MLS

Convenient Location in Downtown Historic Madison! Previous rental, ready to remodel and use your imagination- Make it a residence, Airbnb, long term rental or even a business! Open floor plan with 1/2 bath on main level with 2-3 bedrooms/offices and full bathroom upstairs. Small backyard - just enough for a patio or fenced in area. Selling As Is.

218 E Third Street, Madison

Listing courtesy of eXp Realty, LLC.

$275,000

A RARE DOWNTOWN MADISON TREASURE-HISTORY, CHARACTER & MODERN COMFORT! Step into history with this professionally & completely renovated historic property, built in 1844 by Archibald Taylor, a conductor on the Underground Railroad. Rich in history and timeless architectural appeal, this remarkable Federal-style, timberframed property beautifully preserves its historic character while offering modern-day comfort. Featuring 2 bedrooms, 1.5 baths, four decorative fireplaces, and 2 covered side porches, this property offers charm & character at every turn, Its historic architecture and thoughtful renovation create a truly special opportunity to own a piece of Madison, Indiana's storied past. Whether you're seeking a distinctive full-time residence, a weekend retreat, or a unique investment opportunity, this property offers possibilities as special as its history. The potential for off-street parking adds another desirable feature to this downtown gem.

2 Beds ⋅ 2 Baths ⋅ 2026012645 MLS

A RARE DOWNTOWN MADISON TREASURE-HISTORY, CHARACTER & MODERN COMFORT! Step into history with this professionally & completely renovated historic property, built in 1844 by Archibald Taylor, a conductor on the Underground Railroad. Rich in history and timeless architectural appeal, this remarkable Federal-style, timberframed property beautifully preserves its historic character while offering modern-day comfort. Featuring 2 bedrooms, 1.5 baths, four decorative fireplaces, and 2 covered side porches, this property offers charm & character at every turn, Its historic architecture and thoughtful renovation create a truly special opportunity to own a piece of Madison, Indiana's storied past. Whether you're seeking a distinctive full-time residence, a weekend retreat, or a unique investment opportunity, this property offers possibilities as special as its history. The potential for off-street parking adds another desirable feature to this downtown gem.

627 Walnut Street, Madison

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

$219,900

Welcome home to this charming, cozy 3-bedroom, 2-bath ranch cottage, beautifully remodeled from the bottom up and ready for you to enjoy! Blending timeless charm with fresh, modern updates, this inviting, all-one-level home offers the perfect combination of style, comfort, and low-maintenance living. The thoughtfully designed split-bedroom floor plan provides added privacy, with a true primary suite tucked away on its own side of the home. Throughout, you'll find new LVP flooring, plush bedroom carpet, new cabinetry, and two beautifully updated bathrooms featuring stunning tub-to-ceiling tile. Even the floor joists are new, reflecting the extensive renovation from the ground up. Outside, enjoy a spacious backyard with a storage shed and a large front porch that's perfect for morning coffee or relaxing evenings. Conveniently located within walking distance of Madison Schools and just minutes from shopping, restaurants, and Historic Downtown Madison, this home offers the charm you've been looking for with the peace of mind of a complete remodel. Come see all the care and thoughtful updates that make this a place to call home!

3 Beds ⋅ 2 Baths ⋅ 2026012788 MLS

Welcome home to this charming, cozy 3-bedroom, 2-bath ranch cottage, beautifully remodeled from the bottom up and ready for you to enjoy! Blending timeless charm with fresh, modern updates, this inviting, all-one-level home offers the perfect combination of style, comfort, and low-maintenance living. The thoughtfully designed split-bedroom floor plan provides added privacy, with a true primary suite tucked away on its own side of the home. Throughout, you'll find new LVP flooring, plush bedroom carpet, new cabinetry, and two beautifully updated bathrooms featuring stunning tub-to-ceiling tile. Even the floor joists are new, reflecting the extensive renovation from the ground up. Outside, enjoy a spacious backyard with a storage shed and a large front porch that's perfect for morning coffee or relaxing evenings. Conveniently located within walking distance of Madison Schools and just minutes from shopping, restaurants, and Historic Downtown Madison, this home offers the charm you've been looking for with the peace of mind of a complete remodel. Come see all the care and thoughtful updates that make this a place to call home!

519 Highland Drive, Madison

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

$359,900

This 4-bedroom, 3-bath home is situated in the desirable Country Estates subdivision. Enjoy the covered front porch with a view of Hereford Lake. Home offers living room, dining/gathering room with breakfast bar, eat-in kitchen, large wall of pantry, family room with built-in gas fireplace, and additional room for crafts or your pets' own space. Step outside to an exceptional outdoor setting with a large, well-landscaped backyard, new fencing, and 3 decks for entertaining or your morning coffee or evening relaxation. Large decking for the new pool you have been waiting for. (Pool pump, ladder, steps, electrical hook-up, and automatic chlorinator to remain) 18 x 12 attached utility garage with overhead door for outdoor equipment storage or workshop. Home features a Ring system and MYQ garage door system. Short drive from historic downtown or Madison Hilltop, this home combines the quiet charm of country-style living, recreation, and city convenience.

4 Beds ⋅ 3 Baths ⋅ 2026012720 MLS

This 4-bedroom, 3-bath home is situated in the desirable Country Estates subdivision. Enjoy the covered front porch with a view of Hereford Lake. Home offers living room, dining/gathering room with breakfast bar, eat-in kitchen, large wall of pantry, family room with built-in gas fireplace, and additional room for crafts or your pets' own space. Step outside to an exceptional outdoor setting with a large, well-landscaped backyard, new fencing, and 3 decks for entertaining or your morning coffee or evening relaxation. Large decking for the new pool you have been waiting for. (Pool pump, ladder, steps, electrical hook-up, and automatic chlorinator to remain) 18 x 12 attached utility garage with overhead door for outdoor equipment storage or workshop. Home features a Ring system and MYQ garage door system. Short drive from historic downtown or Madison Hilltop, this home combines the quiet charm of country-style living, recreation, and city convenience.

280 N Lakeside Drive, Madison

Listing courtesy of Century 21 River Valley.

$319,900

This beautiful home offers incredible convenience, situated just a few blocks from the new shopping center on Michigan Rd while backing up to the quiet, desirable Hatcher Hill Road. Additionally, downtown Madison is only a few minutes away. The property features spacious indoor and outdoor living. A newer back deck leads to a nice pool—perfect for warm summer days. There is even a small creek in the tree line that gives addt'l outdoor enjoyment! And the full walkout basement provides excellent space for mechanicals and storage. It is also already plumbed for an extra 1/2 bath in basement! NOTE: The sale of this home is contingent on the seller closing on another specific property to purchase.

4 Beds ⋅ 2 Baths ⋅ 2026012755 MLS

This beautiful home offers incredible convenience, situated just a few blocks from the new shopping center on Michigan Rd while backing up to the quiet, desirable Hatcher Hill Road. Additionally, downtown Madison is only a few minutes away. The property features spacious indoor and outdoor living. A newer back deck leads to a nice pool—perfect for warm summer days. There is even a small creek in the tree line that gives addt'l outdoor enjoyment! And the full walkout basement provides excellent space for mechanicals and storage. It is also already plumbed for an extra 1/2 bath in basement! NOTE: The sale of this home is contingent on the seller closing on another specific property to purchase.

1816 Michigan Road, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$234,900

This updated home is move-in ready with plenty of space and a flexible layout. You’ll find beautiful flooring, lots of natural light, fresh updates throughout, and a kitchen with white cabinets, generous counter space, and new appliances. Multiple living areas give you room for a recreation room, office, game room, or additional gathering space. The home also features central heat and air, comfortable bedrooms, an updated bathroom with a large vanity, and plenty of usable space inside and out. A great combination of updates, space, and character, all ready for its next owner. A one year home warranty provided at closing.

3 Beds ⋅ 2 Baths ⋅ 2026012766 MLS

This updated home is move-in ready with plenty of space and a flexible layout. You’ll find beautiful flooring, lots of natural light, fresh updates throughout, and a kitchen with white cabinets, generous counter space, and new appliances. Multiple living areas give you room for a recreation room, office, game room, or additional gathering space. The home also features central heat and air, comfortable bedrooms, an updated bathroom with a large vanity, and plenty of usable space inside and out. A great combination of updates, space, and character, all ready for its next owner. A one year home warranty provided at closing.

2542 Franks Drive, Madison

Listing courtesy of Paradigm Realty Solutions, LLC.

$199,000

Enjoy the charm and character of an early 1900s home with the peace of mind of a complete rebuild completed in 2023. Rebuilt from the ground up, this home features extensive improvements, including a new foundation, flooring, windows, roof, and more. Offering 3 bedrooms and 1 bathroom, this home combines timeless appeal with the benefits of substantial updates. Step outside and enjoy the large back deck, perfect for entertaining guests, relaxing outdoors, or enjoying your morning coffee. A charming home with a unique history and major improvements already completed—ready for its next owner to make it their own!

3 Beds ⋅ 1 Baths ⋅ 2026012679 MLS

Enjoy the charm and character of an early 1900s home with the peace of mind of a complete rebuild completed in 2023. Rebuilt from the ground up, this home features extensive improvements, including a new foundation, flooring, windows, roof, and more. Offering 3 bedrooms and 1 bathroom, this home combines timeless appeal with the benefits of substantial updates. Step outside and enjoy the large back deck, perfect for entertaining guests, relaxing outdoors, or enjoying your morning coffee. A charming home with a unique history and major improvements already completed—ready for its next owner to make it their own!

417 W State Street, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$169,900

Enjoy the charm of historic downtown Madison in this two-story home offering 1,134 sq. ft. of living space, 3 bedrooms, and 1 full bath. The home features an eat-in kitchen, a spacious loft providing the third bedroom or flexible space, and a cellar-style basement with a utility area and ample storage. Situated on a corner lot with gated access to the rear of the property, this home is conveniently located within walking distance of downtown shops, restaurants, wineries, and all the unique attractions Madison has to offer. Enjoy the character, convenience, and lifestyle of downtown living!

3 Beds ⋅ 1 Baths ⋅ 2026012723 MLS

Enjoy the charm of historic downtown Madison in this two-story home offering 1,134 sq. ft. of living space, 3 bedrooms, and 1 full bath. The home features an eat-in kitchen, a spacious loft providing the third bedroom or flexible space, and a cellar-style basement with a utility area and ample storage. Situated on a corner lot with gated access to the rear of the property, this home is conveniently located within walking distance of downtown shops, restaurants, wineries, and all the unique attractions Madison has to offer. Enjoy the character, convenience, and lifestyle of downtown living!

414 E Third Street, Madison

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

$2,300

**Prime Restaurant Opportunity in Historic Downtown Madison!** Located at 221 E. Main Street in Madison, Indiana, recognized as one of the Best Small Towns in the Midwest, this proven restaurant location offers an exceptional opportunity for an established operator or exciting new dining concept. Situated in the heart of downtown, the property benefits from excellent Main Street visibility, local foot traffic, year-round tourism, and proximity to shopping, entertainment, and established businesses. The space features an approximately 400 SF built-out commercial kitchen with a three-compartment sink, dedicated handwashing sink, and mop sink. Ideally suited for a breakfast or brunch concept, café, bakery, or full-service restaurant. Bring your vision to one of the Midwest's most charming and celebrated historic downtown destinations!

2026012675 MLS

**Prime Restaurant Opportunity in Historic Downtown Madison!** Located at 221 E. Main Street in Madison, Indiana, recognized as one of the Best Small Towns in the Midwest, this proven restaurant location offers an exceptional opportunity for an established operator or exciting new dining concept. Situated in the heart of downtown, the property benefits from excellent Main Street visibility, local foot traffic, year-round tourism, and proximity to shopping, entertainment, and established businesses. The space features an approximately 400 SF built-out commercial kitchen with a three-compartment sink, dedicated handwashing sink, and mop sink. Ideally suited for a breakfast or brunch concept, café, bakery, or full-service restaurant. Bring your vision to one of the Midwest's most charming and celebrated historic downtown destinations!

221 E Main Street, Madison

Listing courtesy of eXp Realty, LLC.

$199,900

2 story home in the heart of downtown Madison. Located in a community recognized by USA Today as the #1 Small Town in the Midwest, this property perfectly blends timeless character with thoughtful modern updates. The recently renovated kitchen features new cabinetry, updated fixtures, and quality butcher block countertops, creating a warm and inviting space ideal for everyday living and entertaining. The spacious primary bedroom and full bath are located upstairs, offering privacy and comfort. An added bonus is the highly sought-after off-street parking, a true rarity in the downtown district. Enjoy walkable access to shops, dining, festivals, and riverfront attractions — all while owning a piece of Madison’s rich history. Schedule your private showing today!

2 Beds ⋅ 2 Baths ⋅ 2026012661 MLS

2 story home in the heart of downtown Madison. Located in a community recognized by USA Today as the #1 Small Town in the Midwest, this property perfectly blends timeless character with thoughtful modern updates. The recently renovated kitchen features new cabinetry, updated fixtures, and quality butcher block countertops, creating a warm and inviting space ideal for everyday living and entertaining. The spacious primary bedroom and full bath are located upstairs, offering privacy and comfort. An added bonus is the highly sought-after off-street parking, a true rarity in the downtown district. Enjoy walkable access to shops, dining, festivals, and riverfront attractions — all while owning a piece of Madison’s rich history. Schedule your private showing today!

715 Walnut Street, Madison

Listing courtesy of Keller Williams Realty Consultants.

$299,000

Imagine enjoying peaceful, secluded living in this immaculate 3-bedroom, 2.5-bath home offering 1,848 sq. ft. of living space on 2.69 acres in a beautiful park-like setting, yet just minutes from town. A gravel drive leads to a barn near the road, while a paved driveway continues to a detached, heated two-car garage with ample room for a workshop, hobbies, or additional hangout space. Step inside from the covered front porch to a welcoming formal living and dining room that flows into a spacious eat-in kitchen and cozy family room featuring a built-in bookcase, electric fireplace, and mounted 75-inch TV. Two bedrooms share a full bath, while the primary suite offers a full-length walk-in closet and private ensuite with a corner soaking tub, walk-in shower, and double vanity. Step outside from the kitchen to a welcoming two-level deck with a gazebo equipped for outdoor TV viewing, overlooking the expansive backyard complete with a pond, storage shed, and dedicated cornhole court. With its inviting interior, versatile garage space, and exceptional outdoor setting, this property offers the perfect blend of comfort, privacy, and convenience.

3 Beds ⋅ 3 Baths ⋅ 2026012649 MLS

Imagine enjoying peaceful, secluded living in this immaculate 3-bedroom, 2.5-bath home offering 1,848 sq. ft. of living space on 2.69 acres in a beautiful park-like setting, yet just minutes from town. A gravel drive leads to a barn near the road, while a paved driveway continues to a detached, heated two-car garage with ample room for a workshop, hobbies, or additional hangout space. Step inside from the covered front porch to a welcoming formal living and dining room that flows into a spacious eat-in kitchen and cozy family room featuring a built-in bookcase, electric fireplace, and mounted 75-inch TV. Two bedrooms share a full bath, while the primary suite offers a full-length walk-in closet and private ensuite with a corner soaking tub, walk-in shower, and double vanity. Step outside from the kitchen to a welcoming two-level deck with a gazebo equipped for outdoor TV viewing, overlooking the expansive backyard complete with a pond, storage shed, and dedicated cornhole court. With its inviting interior, versatile garage space, and exceptional outdoor setting, this property offers the perfect blend of comfort, privacy, and convenience.

4170 W 700 N, Madison

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

$276,900

Located on Historic Madison's Main Street. Close to the riverfront, heritage trail, festivals, concerts, shopping, and dining. Featuring 2 bedrooms, two updated baths and updated kitchen with granite countertops and all appliances. Possible third bedroom, den, or office. Custom-made wormy pine flooring from Tiny Timber in entry, kitchen, and dining. Large entry from covered porch. 15 x 16 wood deck great for enjoying a morning cup of coffee or entertaining in the evening. Oversized two-story car pole barn garage. Garage has ample storage with possibilities of a guest suite. Furniture in hallway and living room will remain. Home is being sold "AS IS", requires a little TLC.

2 Beds ⋅ 2 Baths ⋅ 2026012641 MLS

Located on Historic Madison's Main Street. Close to the riverfront, heritage trail, festivals, concerts, shopping, and dining. Featuring 2 bedrooms, two updated baths and updated kitchen with granite countertops and all appliances. Possible third bedroom, den, or office. Custom-made wormy pine flooring from Tiny Timber in entry, kitchen, and dining. Large entry from covered porch. 15 x 16 wood deck great for enjoying a morning cup of coffee or entertaining in the evening. Oversized two-story car pole barn garage. Garage has ample storage with possibilities of a guest suite. Furniture in hallway and living room will remain. Home is being sold "AS IS", requires a little TLC.

957 W Main Street, Madison

Listing courtesy of Century 21 River Valley.

$204,900

Very clean 3 BR 1 BA home on a deadend street. GFA furnace adn C/A approx. 3 years old Roof 5-6 years old. Replacement windows. 7x30 covered front porch. Detached garage is a fooler! 15x46. Take a look today!

3 Beds ⋅ 1 Baths ⋅ 2026012619 MLS

Very clean 3 BR 1 BA home on a deadend street. GFA furnace adn C/A approx. 3 years old Roof 5-6 years old. Replacement windows. 7x30 covered front porch. Detached garage is a fooler! 15x46. Take a look today!

327 MONTCLAIR Street, Madison

Listing courtesy of Real Estate Inc.

$174,900

3 BR 2 FULL BA Brick and frame home. Priced to sell. Selling as is. New metal roof and 6" gutters this year. New front and rear doors with new storm doors. New 10x12 deck on back. 8x21 covered front porch. This could be a very nice home. Sellers can not finish at this time. Priced accordingly.

3 Beds ⋅ 2 Baths ⋅ 2026012612 MLS

3 BR 2 FULL BA Brick and frame home. Priced to sell. Selling as is. New metal roof and 6" gutters this year. New front and rear doors with new storm doors. New 10x12 deck on back. 8x21 covered front porch. This could be a very nice home. Sellers can not finish at this time. Priced accordingly.

1713 Valley Drive, Madison

Listing courtesy of Real Estate Inc.

$479,000

Historic 1855 home on 5 acres. Built more than 170 years ago of solid brick, this residence retains it's robust construction and period character. The home has been fully rewired, plumbed, insulated, and features Pella windows throughout. The roof and gutters were new in 2023. 2,468 sq ft with 4 bedrooms and 2 full baths. The primary bedroom includes his-and-hers closets and an en-suite bath with a clawfoot tub and separate shower. Original wood floors in much of the house, oak cabinetry, and stainless appliances. Concrete patio overlooks open fields and mature trees. A standout feature is the 36×54 high-ceiling pole barn garage (2019), fully insulated and heated for workshop, storage, or multi-use. Located just outside Madison city limits—3.2 miles from McDonald’s and 4.3 miles from Walmart—it offers convenient access to daily needs while retaining a distinctly rural setting near historic Madison. Authentic mid-19th-century brick architecture paired with practical modern updates. Virtual Tour: https://tour.panoee.net/madison-paper-mill-house/img_20261027_143555_465

4 Beds ⋅ 2 Baths ⋅ 2026012604 MLS

Historic 1855 home on 5 acres. Built more than 170 years ago of solid brick, this residence retains it's robust construction and period character. The home has been fully rewired, plumbed, insulated, and features Pella windows throughout. The roof and gutters were new in 2023. 2,468 sq ft with 4 bedrooms and 2 full baths. The primary bedroom includes his-and-hers closets and an en-suite bath with a clawfoot tub and separate shower. Original wood floors in much of the house, oak cabinetry, and stainless appliances. Concrete patio overlooks open fields and mature trees. A standout feature is the 36×54 high-ceiling pole barn garage (2019), fully insulated and heated for workshop, storage, or multi-use. Located just outside Madison city limits—3.2 miles from McDonald’s and 4.3 miles from Walmart—it offers convenient access to daily needs while retaining a distinctly rural setting near historic Madison. Authentic mid-19th-century brick architecture paired with practical modern updates. Virtual Tour: https://tour.panoee.net/madison-paper-mill-house/img_20261027_143555_465

4515 N Paper Mill Road, Madison

Listing courtesy of Paradigm Realty Solutions, LLC.

$259,900

Built around 1870, this charming 2-story Federal-style brick home is located in the heart of downtown Madison, just half a block from the Ohio River and outside the flood plain. Offering 1,668 sq ft, the home features 3–4 bedrooms and 2 full baths, 3/4 unfinished basement blending timeless historic character with everyday convenience. Enjoy being within walking distance—or a quick golf cart ride—to local shops, dining, parks, festivals, and events. Inside, you’ll find spacious living areas filled with natural light and classic architectural details. The flexible layout allows for everyday living on the main level with additional space upstairs for guests. Recent updates, including a newer roof, windows, and water heater, add peace of mind while leaving room to make it your own. Outside, the low-maintenance yard includes a storage shed, with all appliances, blinds, and even lawn equipment included. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this downtown gem offers location, charm, and versatility!

3 Beds ⋅ 2 Baths ⋅ 2026012567 MLS

Built around 1870, this charming 2-story Federal-style brick home is located in the heart of downtown Madison, just half a block from the Ohio River and outside the flood plain. Offering 1,668 sq ft, the home features 3–4 bedrooms and 2 full baths, 3/4 unfinished basement blending timeless historic character with everyday convenience. Enjoy being within walking distance—or a quick golf cart ride—to local shops, dining, parks, festivals, and events. Inside, you’ll find spacious living areas filled with natural light and classic architectural details. The flexible layout allows for everyday living on the main level with additional space upstairs for guests. Recent updates, including a newer roof, windows, and water heater, add peace of mind while leaving room to make it your own. Outside, the low-maintenance yard includes a storage shed, with all appliances, blinds, and even lawn equipment included. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this downtown gem offers location, charm, and versatility!

115 Walnut Street, Madison

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

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