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

605 Walnut Street, Madison
2510 Franks Drive, Madison
$170,000
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
1041 W MAIN Street, Madison
$189,900
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
512 E Main Street Unit 1, Madison
$199,900
1 Beds ⋅ 1 Baths ⋅ 202608700 MLS ⋅ ACTIVE Status
Experience downtown living at its finest in this sunny first-floor condo located in a beautiful historic building on Main Street in Madison. Offering approximately 1,000 square feet, this charming condo features soaring 12-foot ceilings throughout, creating a bright and spacious atmosphere. The large one-bedroom, one-bath layout includes a walk-in shower, inviting family room with a fireplace, and a charming eat-in kitchen perfect for everyday living. Additional highlights include bonus exterior storage space, shared patio area, off-street parking, and several newer appliances. Conveniently located just steps from local shops, restaurants, wineries, popular festivals, and the scenic Ohio River, this condo offers the perfect blend of historic charm and downtown convenience. A must-see opportunity!

512 E Main Street Unit 1, Madison
931 W Main Street, Madison
$219,900
2 Beds ⋅ 2 Baths ⋅ 202608635 MLS ⋅ ACTIVE Status
Charming two-story home located in the heart of downtown Madison! This well-maintained property offers 2 bedrooms, 2 full baths, a spacious living room, cozy family room, large laundry room, separate dining area, and an inviting kitchen with plenty of space for everyday living. Enjoy relaxing on the covered front porch with Main Street views. Take advantage of alley access to the backyard with convenient off-street parking. Recent updates include a newer roof approximately 5 years old and Thermopane windows throughout. Just a short walk to downtown shops, local eateries, wineries, and the picturesque Ohio River waterfront, this home combines comfort, convenience, and small-town charm in an ideal location.

931 W Main Street, Madison
423 Mill Street, Madison
$265,000
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
2159 Lanier Drive, Madison
$219,000
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
707 Walnut Street, Madison
$114,900
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
1122 W Second Street, Madison
$250,000
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

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