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1020 W 2nd Street, Madison
$319,000
4 Beds ⋅ 2 Baths ⋅ 2026011340 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated 4-bedroom, 2-full-bath, two-story home located on 2nd Street in the heart of historic downtown Madison! Situated outside the floodplain, this home offers an ideal combination of historic downtown charm and modern updates. The interior features spacious bedrooms and high ceilings on both the first and second floors, creating an open and inviting feel throughout. Major improvements include brand-new electrical and HVAC systems, updated plumbing, new appliances, cabinetry, countertops, and flooring, making this home move-in ready. Step outside onto the second-story deck and enjoy partial views of the Ohio River. The property also features a large contiguous lot with multiple off-street parking spaces conveniently accessible from the alley—a valuable find in downtown Madison. Priced right and ready to sell, this home is perfectly positioned near the restaurants, shops, entertainment, festivals, and attractions that make historic downtown Madison such a desirable place to live. Whether you’re looking for a primary residence, weekend getaway, or investment opportunity, this downtown property is one you won’t want to miss!

1020 W 2nd Street, Madison
2241 Seneca Drive, Madison
$209,000
3 Beds ⋅ 2 Baths ⋅ 2026010596 MLS ⋅ ACTIVE Status
This spacious 3-bedroom, 1.5-bath home offers a practical layout with plenty of living space. The standout feature is the location, as the property sits right against Clifty Falls State Park, giving you quick access to trails and nature. Inside, the house feels open and functional, making it a great fit for anyone wanting a solid home with an incredible backyard extension. You can cross new roof off your to do's because the roof is just under 3 years old. It is a quiet, convenient spot that lets you enjoy the connivence of being located on Madison's hilltop!

2241 Seneca Drive, Madison
411 W State Street, Madison
$189,900
3 Beds ⋅ 1 Baths ⋅ 2026011097 MLS ⋅ ACTIVE Status
Offering 1,348 square feet of living space, this 3-bedroom, 1-bath home provides plenty of flexibility to fit your needs. The converted garage creates a spacious bonus room that could serve as a second living area, home office, or potential 4th bedroom. Major updates include a newer HVAC system, windows approx. a year old, and a roof approximately 8 years old. Outside, enjoy a private, fully fenced backyard—perfect for pets, outdoor activities, or simply relaxing. A solid opportunity with versatile living space and room to make it your own!

411 W State Street, Madison
132 Mouser Street, Madison
$265,000
3 Beds ⋅ 2 Baths ⋅ 2026010890 MLS ⋅ ACTIVE Status
Classic Bedford Stone Ranch on a Double Lot with Big Upgrades & Endless Possibilities! Discover easy, single-level living on this solid Bedford stone ranch situated on two parcels totaling approximately .47 acres, offering an exceptional amount of space and flexibility in a convenient location near local schools, shopping, and dining. The 3-bedroom, 2-bath home features a roof installed in 2018, HVAC replaced in 2022, a new crawl space moisture barrier installed in 2021, and a brand-new water heater. The additional parcel extends the backyard and provides access from Wray Street, creating added space for future possibilities such as an in-law suite, garage, lean-to for boat or recreational storage, workshop, expanded outdoor space, or whatever best fits your lifestyle, subject to applicable approvals and restrictions. Step outside to enjoy a large, fully fenced yard with a storage shed, mature shade trees, and plenty of room for entertaining, gardening, pets, or relaxing. Additional conveniences include a covered carport and paved driveway. With its solid construction, desirable location, extensive updates, and rare double-lot setting, this property offers both comfortable living and room to grow. Schedule your private showing today!

132 Mouser Street, Madison
413 Bellaire Drive, Madison
$209,900
3 Beds ⋅ 2 Baths ⋅ 2026011045 MLS ⋅ ACTIVE Status
Check out this 3-bedroom, 1.5-bath home hardwood floors, a newer roof, and newer HVAC. It has a very nice porch to enjoy as well. The home may need a little TLC, but with some care and personal touches, it has the potential to become a wonderful home. A great opportunity for buyers looking to add their own style and value. Come take a look and imagine the possibilities!

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

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

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

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

1344 Lockard Street, Madison
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
5260 W Quail Run Lane, Madison
$324,900
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
2037 Ridgewood Drive, Madison
$339,999
3 Beds ⋅ 2 Baths ⋅ 202609219 MLS ⋅ ACTIVE Status
Beautifully updated 3-bedroom, 2 full bath home located in the desirable Sunrise neighborhood and within walking distance of Sunrise Golf Course. This move-in ready home features a spacious kitchen complete with appliances, a large pantry, center island, and dining area—perfect for everyday living and entertaining. Generous-sized bedrooms offer walk-in closets, while an additional room provides the ideal space for a home office, hobby room, or flex space. Step outside to enjoy the large covered rear deck and patio overlooking the nice-sized backyard, complete with a raised garden bed and a storage shed. Thoughtfully updated throughout, this home combines modern conveniences with comfortable living in a great location. Don't miss this opportunity to own a beautifully redone home in one of the area's most sought-after neighborhoods!

2037 Ridgewood Drive, Madison
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
316 W Main Street, Madison
$350,000
1 Beds ⋅ 1 Baths ⋅ 202609040 MLS ⋅ ACTIVE Status
Discover this Italianate two-part in a commercial block, constructed circa 1870, brimming with potential for various business ventures or investment opportunities! **Property Highlights** Spacious first floor - Enjoy approximately 3140 sq ft of versatile space, perfect for retail or office use. Flexible Second Floor - Currently utilized for storage, this level can easily be transformed to suit your needs, whether it be additional office space or even more retail opportunities. Third Floor Comfort - A welcoming apartment provides both convenience and potential rental income, making this property a smart investment. Property runs from Main Street to the back alley. Don't miss out on a chance to own this property! Contact us today for more information or schedule a viewing.

316 W Main Street, Madison
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
401 Maple Hill Drive, Madison
$310,000
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
612B W Second Street Unit 4, Madison
$324,900
2 Beds ⋅ 3 Baths ⋅ 202608000 MLS ⋅ ACTIVE Status
Spacious, comfortable condominium in downtown Madison. Features tall ceilings, beautiful woodwork, and great natural light throughout. Cherry kitchen cabinets, granite counter top, all appliances, and breakfast bar. Large main suite with oversized window overlooking gardens and rooftops. Main suite includes well designed walk-in closet. Besides the main suite bath additional full bath and half bath off the second bedroom. Fireplaces are decorative. Beautiful staircase in common area with landing at this unit and additional back staircase. Large front porch for residence use. Front and back staircase. One car garage space with storage. Great location blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today's Best Small Town in the Midwest"--has to offer.

612B W Second Street Unit 4, Madison
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
610A W Second Street Unit 1, Madison
$324,900
3 Beds ⋅ 2 Baths ⋅ 202607581 MLS ⋅ ACTIVE Status
Beautiful first floor Federal style condominium blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today's Best Small Town in the Midwest"--has to offer. Amazing remodeled kitchen boasts all major appliances, granite counter top, track lighting, under-cabinet lighting and plenty of counter space. Open floor plan with 10 ft ceilings, crown molding, recess lighting, chandeliers, hardwood flooring in foyer, living room and kitchen. Split bedrooms with owner using third bedroom as a sitting room. Owners suite has large dressing closet with additional vanity and built in desk. Large front porch for residence use. Small patio for owners use. One car garage space with storage and easy access from the condo. Don't let this move-in ready maintenance-free home pass you by.

610A W Second Street Unit 1, Madison
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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