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$265,000
3 Beds ⋅ 2 Baths ⋅ 202607860 MLS
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

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

$464,500
4 Beds ⋅ 4 Baths ⋅ 202607755 MLS
Completely remodeled and thoughtfully designed, this stunning 4-bedroom, 3.5-bath home offers 2,544 sq ft of beautifully updated living space in the heart of downtown Madison. Blending modern updates with timeless character, you’ll find exposed brick, wood beams, and quality craftsmanship throughout. The spacious kitchen features abundant cabinetry, a pantry, large island, and an attached dining area—perfect for everyday living and entertaining. The primary suite offers a generous layout with a large bath, and large closet. while natural light fills the home, creating a warm and inviting atmosphere, you wont want to miss what outside has to offer! Enjoy a private courtyard ideal for relaxing or outdoor dining, which leads to a detached two-car garage for added convenience and storage. Located just moments from shops, dining, wineries, and all that downtown Madison has to offer, this home is truly a must-see.

422 St Michaels Avenue, Madison

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

$160,000
2 Beds ⋅ 1 Baths ⋅ 202607644 MLS
Price adjustment! This charming home on a corner lot is perfectly positioned in the heart of downtown Madison, just minutes from the bridge and all the activities this vibrant community is known for. Enjoy the convenience of walkable living while still having your own private retreat. This home features hardwood and tile flooring, a dining room, and a layout ideal for everyday living and entertaining. The kitchen comes equipped with a gas stove and refrigerator (both new in 2022) Downstairs, you’ll find a partially finished full basement, offering additional living space and room to customize to your needs. There’s also attic access with a wood floor for even more storage. Step outside to enjoy the fenced yard, perfect for pets or gatherings. The property also includes a single-car detached garage and sits on a desirable corner lot. Key Updates & Features Include: Tankless water heater 2021 Water softener 2021 New interior water lines 2020 New exterior water & sewer lines 2025 HVAC system 2017 Roof, gutters, and aluminum siding 2019 Exterior cameras stay with the home (interior cameras function as live monitors only) As a unique bonus, the tanning bed will remain. With its prime location near the bridge for easy commuting, plus numerous updates, this home offers both convenience and peace of mind. Property is being sold AS IS. Buyers are welcome to complete any inspections, however the Sellers will not make repairs or provide repair concessions.

904 E Second Street, Madison

Listing courtesy of eXp Realty, LLC.

$1,375,000
10 Beds ⋅ 8 Baths ⋅ 1713737 MLS
Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you're just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana's most sought after river towns.

513 & 515 West St, Madison

Listing courtesy of EXP Realty LLC.

$1,375,000
10 Beds ⋅ 8 Baths ⋅ 202607078 MLS
Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you’re just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana’s most sought after river towns.

513 & 515 West Street, Madison

Listing courtesy of eXp Realty, LLC.

$379,000
3 Beds ⋅ 2 Baths ⋅ 202606645 MLS
Historic Federal style home built in 1850 in the heart of historic downtown Madison. Step into a beautifully maintained home by its owners. You will be welcomed by a open staircase, sunny living, and dining rooms with original, restored pine floors. Living room features the orginal fireplace (now decorative) and leaded glass hangings in the front windows. Large kitchen is highlighted with vintage General Electric steel kitchen cabinets in amazing condition. Granite counter top and tile back-splash. The unique kitchen floor is plank eucalyptus. The rear project/utility/garden room has a large storage closet and big picture window looking at the landscaped and peaceful fenced yard and patio. Covered back door entrance. Three spacious bedrooms. Second and third bedrooms currently used by the homeowners as TV/reading room and office. Completely remodeled baths (full and half) with tile flooring, shower, refinished claw-foot tub and stainglass window hangings in the full bathroom. Home is located close to dining, shopping, riverfront, festivals and all that Madison---USA Today's "Best Small Town in the Midwest"--has to offer.

507 E Main Street, Madison

Listing courtesy of Century 21 River Valley.

$376,900
2 Beds ⋅ 2 Baths ⋅ 202606763 MLS
Scenic river view and comfortable downtown living in this two year old home. This two bedroom, two bath residence provides a designer kitchen with breakfast bar, granite counter top and tile backsplash. Open concept living and dining area with open staircase to basement. River view from living and dining areas. Large family room walk-out to covered patio and river view. Have your morning coffee or evening beverage with view of the sun shinging on the river or the sunset over the bridge. Home is located close to river walk, riverfront parks, dining, shopping, festivals and all that Madison---USA Todays's "Best Small Town in the Midwest"--has to offer.

1010 E First Street, Madison

Listing courtesy of Century 21 River Valley.

$264,900
3 Beds ⋅ 2 Baths ⋅ 202606836 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, 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.

$349,900
4 Beds ⋅ 3 Baths ⋅ 202606801 MLS
Fully renovated historic Federal-style brick home located in downtown Madison. This two-story property offers 4 bedrooms and 2.5 bathrooms and blends timeless character with modern updates. Features include a spacious open kitchen with new cabinetry, stainless steel appliances, center island with breakfast bar, coffee bar, and butler’s pantry. Main level includes living room, flex room that offers the potential for a main level bedroom or office, powder room, and large laundry room with sink. Home showcases three decorative fireplaces and a primary suite with ensuite bath featuring double vanity and tiled shower. Enjoy a private fenced backyard, detached 2-car garage, and cellar for storage. Located in the heart of historic downtown near local shops and dining.

518 Jefferson Street, Madison

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

$264,900
3 Beds ⋅ 2 Baths ⋅ 202606592 MLS
Motivated Seller!!! Beautiful new construction home offering 1,450 sq ft of thoughtfully designed living space. This 3-bedroom, 2 full bath home features an open floor plan connecting the kitchen, dining area, and living room—perfect for everyday living and entertaining. The eat-in kitchen includes stainless steel appliances, abundant cabinet space, a large pantry, and a center island with additional storage drawers. The spacious primary suite offers a private bath with double vanity, walk-in shower, and both a walk-in closet plus a second closet for extra storage. The second full bath features a convenient tub/shower combination. Additional highlights include plenty of natural lighting throughout, a separate laundry room that leads directly to the garage, and a paved driveway with a turnaround for easy access. Step outside to enjoy the fenced backyard and back deck—ideal for relaxing or entertaining.

3450 N Michigan Road, Madison

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

$459,000
1 Beds ⋅ 1 Baths ⋅ 202605428 MLS
If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

2945 N Greenbrier Road, Madison

Listing courtesy of Trueblood Real Estate.

$219,000
2 Beds ⋅ 2 Baths ⋅ 2025013009 MLS
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

Listing courtesy of Century 21 River Valley.

$129,000
2025012675 MLS
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

Listing courtesy of Legacy Land Use & Realty.

$284,900
3 Beds ⋅ 1 Baths ⋅ 1703460 MLS
Immediate possession! Country Living with Convenience! Enjoy the best of both worlds with this brick 3 bedroom, 1.5 bath home situated in a rural setting, yet just 10 minutes from Madison's hilltop and about an hour from both Columbus and Jeffersonville, IN. The home offers multiple living spaces with a living room, family and a sunroom making this great for gatherings. The converted garage now serves as a spacious 19.7 x 13.9 bonus room, currently a laundry space, but ideal for storage, hobbies, a workshop, or even a man cave. A 26x32 detached 2 car garage and ample driveway parking add convenience. For horse enthusiasts, the property offers a 100x24 barn with 6 to 8 stalls, a tack room, and a large fenced pasture area. With so much space inside and out, this home provides endless possibilities for country living. This home has been recently inspected with no major defects found. Buyers are welcome to conduct any and all inspections; property is being sold in current condition, with no repairs to be made by the seller. With a full price offer, seller will give at closing a check to roofer for $9350.00 see attached estimate.

6734 N SR 7, Madison

Listing courtesy of EXP Realty LLC.

$284,900
3 Beds ⋅ 2 Baths ⋅ 2025011353 MLS
Immediate Possession! Country Living with Convenience! Enjoy the best of both worlds with this brick 3 bedroom, 1.5 bath home situated in a rural setting, yet just 10 minutes from Madison's hilltop and about an hour from both Columbus and Jeffersonville, IN. The home offers multiple living spaces with a living room, family and a sunroom making this great for gatherings. The converted garage now serves as a spacious 19.7 x 13.9 bonus room, currently a laundry space, but ideal for storage, hobbies, a workshop, or even a man cave. A 26x32 detached 2 car garage and ample driveway parking add convenience. For horse enthusiasts, the property offers a 100x24 barn with 6 to 8 stalls, a tack room, and a large fenced pasture area. With so much space inside and out, this home provides endless possibilities for country living. This home has been recently inspected with no major defects found. Buyers are welcome to conduct any and all inspections; property is being sold in current condition, with no repairs to be made by the seller.

6734 N SR 7, Madison

Listing courtesy of eXp Realty, LLC.

$274,500
2 Beds ⋅ 2 Baths ⋅ 2025012327 MLS
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

Listing courtesy of eXp Realty, LLC.

$454,900
5 Beds ⋅ 3 Baths ⋅ 202409255 MLS
So many possibilities await you with this lovingly maintained home on over 1 1/2 acres with mature trees and a parklike setting with a decorative pond. This home offers 3 bedrooms, 2 full baths, one with a jetted tub and heated tile floor, living room with a gas fireplace, eat in kitchen with a pantry and granite counter tops, family room with a brick hearth and flue for a wood stove and a utility room in the main living quarters. In addition to the main living area, there is an attached living quarters/guest suite with a kitchen, full bathroom, 2 bedrooms, a living room/play room and it's own front entry and rear entry with a deck. Wait that isn't all! There are front and rear keyless entries on main living quarters doors, 2 - 2+ car detached garages, a blacktop drive with extras parking, a nice back patio and a 24' above ground pool with a deck. This home is conveniently located within 4 miles of Madison's hilltop area and Clifty Falls State Park, within 4.5 miles from Hanover and within 5 miles of Madison's historic downtown area that was named the #1 Small Town in the Midwest by USA Today 10 Best Readers' Choice Award for 2024. Potted plants will be taken by Seller and some starts off of some perennials will be take by the seller. New Survey Attached. New w/s installed July 2025 also new elements in water heater. All new paint June-July 2026 in the living room, kitchen, hallway, 1 bedroom and 1 bathroom. Mantel @ fireplace will not convey.

317 Meadow Lane, Madison

Listing courtesy of Real Estate Inc.