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235 E Schafer Lane, Madison
$280,000
4 Beds ⋅ 2 Baths ⋅ 2026011732 MLS ⋅ ACTIVE Status
Looking for a property that offers space, privacy, and plenty of possibilities? Welcome to East Schafer Lane in Madison, Indiana! Tucked away on a quiet dead-end road and surrounded by mature trees, this home offers a peaceful setting with the convenience of being just a short drive from downtown Madison, local shopping, dining, schools, and everyday amenities. The flexible layout features two private entrances, creating options for separate living quarters, multi-generational living, a home office setup, or potential income-producing space. Whether you're searching for a home with room to spread out, space to accommodate changing needs, or a property you can make your own, this one offers versatility in a great Madison location. Enjoy the privacy of the tree-lined setting while staying within easy reach of everything this historic river town has to offer. Come explore the possibilities! Square footage and room sizes are approximate; buyer to verify.

235 E Schafer Lane, Madison
542 W Seventh Street, Madison
$279,000
3 Beds ⋅ 2 Baths ⋅ 2026012503 MLS ⋅ ACTIVE Status
This three-bedroom, two full bath, ranch-style home is neat as a pin inside and out. Located in a quiet, tree-lined neighborhood. Is a must-see for any Buyer looking for an inviting home. Imagine enjoying warm evenings on the covered front porch, barbecues on the back deck, or just staying cozy on a winter evening. Close to everything! Within walking distance to Madison Consolidated's junior high and high school campuses, near Clifty Drive shopping and restaurants, and only minutes from Historic Downtown Madison. Eat-in kitchen includes a disposal, microwave, stove and refrigerator; utility room includes washer and dryer. And there's plenty of parking, with an attached two-car garage and free-standing two-car pole barn, each with paved driveways, offering plenty of storage for lawn and garden equipment and other tools.

542 W Seventh Street, Madison
957 W Main Street, Madison
$276,900
2 Beds ⋅ 2 Baths ⋅ 2026012641 MLS ⋅ ACTIVE Status
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
225 E Main Street, Madison
$275,000
202608094 MLS ⋅ ACTIVE Status
Located in the heart of downtown Madison on Main Street, this versatile three-story building offers 2,745 sq ft and endless possibilities. The main floor is currently operating as a t-shirt shop, but the space could easily accommodate a variety of retail, office, or service-based businesses. The upper floors provide excellent rental or residential potential. The second floor offers additional usable space, while the third floor is unfinished and ready for a buyer to customize to fit their needs. With the option to live and work in the same building or generate additional rental income, this property presents a unique investment opportunity. Situated on Main Street in Madison IN with high foot and vehicle traffic, you’ll be just steps away from popular restaurants, shops, wineries, and local attractions. A prime location with incredible potential in one of southern Indiana’s most charming historic downtowns.

225 E Main Street, Madison
152 E CR 350 N, Madison
$274,900
4 Beds ⋅ 2 Baths ⋅ 2026011539 MLS ⋅ ACTIVE Status
Beautifully updated home on 1 acre. Home has a front and back deck for enjoying nature and relaxation. 4 bedrooms with 2 full baths. Lots of refinished hardwood throughout. New kitchen with granite countertops, new appliances, and new cabinets. New roof, paint, floors, baths, kitchen, and much more. Plenty of parking including a 1 car garage with an extra room. This property is a must see! Call today!!

152 E CR 350 N, Madison
709 Montclair Street, Madison
$269,900
3 Beds ⋅ 2 Baths ⋅ 2026012233 MLS ⋅ ACTIVE Status
Welcome to this beautifully maintained 3-bedroom, 2 full bath home situated on a desirable corner lot in Madison’s hilltop area, just two blocks from the junior high and high schools. Thoughtfully updated and cared for, the home offers an inviting open-concept layout with fresh paint, recessed lighting, ceiling fans, and a mix of refinished hardwood, carpet, and tile flooring. The spacious primary bedroom features a walk-in closet with built-in organizers, while the remodeled full bath and convenient half bath add comfort and functionality. The kitchen flows easily into the living and dining areas and includes the refrigerator, range, and dishwasher. A fireplace offers the option for ventless gas logs, and the breezeway provides a convenient laundry area with washer and dryer. Outside, enjoy established landscaping, mature trees, a privacy-fenced backyard, and large deck—perfect for relaxing or entertaining. Recent improvements include a new water heater in December 2025, new furnace blower motor, thermostat and three control boards in 2026, plus a remodeled bathroom. Additional features include a newer roof, replaced main water and sewer lines, crawl space vapor barrier and sump pump, LeafFilter gutter guards, and double-hung windows with lifetime guarantees. Move-in ready and conveniently located near schools, shopping, and downtown Madison, this home offers comfort, convenience, and thoughtful updates throughout.

709 Montclair Street, Madison
725 W Third Street, Madison
$269,000
3 Beds ⋅ 2 Baths ⋅ 2026011867 MLS ⋅ ACTIVE Status
Completely remodeled and move-in ready, this downtown home offers the feel of new construction with the character of its historic setting. The extensive remodel includes a new roof, windows, HVAC, wiring, plumbing, siding, and front and rear covered porches. The thoughtfully designed interior features a spacious second-floor primary suite with access to a Jack-and-Jill bathroom shared with an additional bedroom, plus convenient laundry. The stylish kitchen offers stainless steel appliances and a granite island. Located in Madison’s historic district, just one block from Lydia Middleton Elementary School and within easy walking distance of downtown shops, restaurants, and more. This beautifully updated home is ready for its next chapter!

725 W Third Street, Madison
723 W Third Street, Madison
$269,000
3 Beds ⋅ 2 Baths ⋅ 2026011865 MLS ⋅ ACTIVE Status
Completely remodeled and move-in ready, this downtown home offers the feel of new construction with the character of its historic setting. The extensive remodel includes a new roof, windows, HVAC, wiring, plumbing, siding, and front and rear covered porches. The thoughtfully designed interior features a spacious second-floor primary suite with access to a Jack-and-Jill bathroom shared with an additional bedroom, plus convenient laundry. The stylish kitchen offers stainless steel appliances and a granite island. Located in Madison’s historic district, just one block from Lydia Middleton Elementary School and within easy walking distance of downtown shops, restaurants, and more. This beautifully updated home is ready for its next chapter!

723 W Third 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
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
115 Walnut Street, Madison
$259,900
3 Beds ⋅ 2 Baths ⋅ 2026012567 MLS ⋅ ACTIVE Status
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
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
410 Mouser Street, Madison
$249,900
3 Beds ⋅ 2 Baths ⋅ 2026011716 MLS ⋅ ACTIVE Status
Welcome home to this move-in ready 3-bedroom, 1.5-bathroom gem offering the perfect blend of modern comfort and outdoor convenience right here in Madison! Step inside to find a fully equipped kitchen featuring a refrigerator, dishwasher, range, and garbage disposal, all complementing a highly functional floor plan. In the utility room there is a washer and dryer included. Behind the scenes, this home offers premium updates, including energy-efficient thermopane windows that flood the home with natural light and a water softener system. The exceptional living space extends outdoors! The sliding doors lead you out to a spacious concrete patio, ideal for weekend barbecues and morning coffee. Enjoy a fully fenced-in backyard that offers a secure area for children or pets to run free. Storage is never an issue thanks to the sizable outdoor storage shed. Whether you are a first-time homebuyer or looking to downsize, this meticulously maintained property is ready for you to move right in and make it your own!

410 Mouser Street, 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
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
2315 Allen Street, Madison
$239,000
3 Beds ⋅ 1 Baths ⋅ 2026012265 MLS ⋅ ACTIVE Status
This beautiful Bedford Stone house has 3 bedrooms and 1 bathroom. There is a large backyard with tremendous potential. The home offers original hardwood flooring. There is a nice deck off of the backside of the home. The home has an open concept layout, with a kitchen island included. The property is located within the neighborhood adjacent to Madison Junior/Senior high schools. This central hilltop location is a perfect fit for a classic home such as this one. Make it yours!

2315 Allen Street, Madison
520 Seventh Street, Madison
$227,900
4 Beds ⋅ 2 Baths ⋅ 2026011160 MLS ⋅ ACTIVE Status
Seller is offering $5,000 towards closing costs or a rate buydown! Check out this great 4 BEDROOMS 2 full bath home! Location! Detached garage! Spacious corner lot with a metal roof for peace of mind. Come take a look today!

520 Seventh Street, 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
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
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
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
327 MONTCLAIR Street, Madison
$204,900
3 Beds ⋅ 1 Baths ⋅ 2026012619 MLS ⋅ ACTIVE Status
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
111 E Fourth, Madison
$199,999
2026012292 MLS ⋅ ACTIVE Status
This is the Custer-Cosby house, and the pursuer of this property will become a next person in the fabled legacy from within these walls. The original front of the home is enhanced by its restoration. Behind the front rooms is an entirely fitting new build! The property is being marketed to the person who wants to make this house a home. The bones are good and the opportunities endless! There are architect floorplans that can be your layout design, or you may entirely reimagine it for your use. There is a good area for outdoor enjoyment with an interior yard porch that is inviting. This is best understood with a look for yourself!

111 E Fourth, Madison
715 Walnut Street, Madison
$199,900
2 Beds ⋅ 2 Baths ⋅ 2026012661 MLS ⋅ ACTIVE Status
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
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
1667 E Wehner Drive, Madison
$189,900
3 Beds ⋅ 1 Baths ⋅ 2026011479 MLS ⋅ ACTIVE Status
Move-In Ready & Energy-Efficient 3-Bedroom Ranch. Welcome to 1667 E Wehner Drive. 3-bedroom, 1-bathroom single-family home offers 1,101 sq. ft. on a 0.34-acre lot in the quiet Wehner Addition subdivision. What truly sets this property apart is the extensive list of high-ticket, structural upgrades designed for worry-free living and low utility bills: Roof & Flooring: A durable, low-maintenance metal roof was installed just 9 years ago, alongside beautiful updated flooring throughout most of the home. HVAC & Windows: Enjoy year-round comfort and efficiency with a central HVAC system and replacement windows—all less than 10 years old. Superior Insulation: The crawl space is fully insulated, and the attic has been insulated well above standard requirements, ensuring maximum energy savings. Outside, the yard provides opportunities for gardening, pets, or outdoor entertaining. Located just minutes from historic downtown Madison, local shopping, and Clifty Falls State Park, this home is perfect for first-time buyers, downsizers, or savvy investors. Schedule your showing today before it's gone!

1667 E Wehner 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
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
1713 Valley Drive, Madison
$174,900
3 Beds ⋅ 2 Baths ⋅ 2026012612 MLS ⋅ ACTIVE Status
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
2078 E Gardner Lane, Madison
$174,900
3 Beds ⋅ 1 Baths ⋅ 2026012347 MLS ⋅ ACTIVE Status
Nice 3-bedroom, 1 bath home located on a quiet cul-de-sac just minutes from beautiful downtown Madison. The home has had some great updates including all new flooring and fresh paint throughout. The bathroom has been completely remodeled, and the HVAC is only 2 years old. Conveniently located near downtown, shopping, restaurants, and local amenities. This one is move-in ready!!!

2078 E Gardner Lane, Madison

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