Properties For Sale in West Main Street, Madison

Azalea Manor, a historic Federal-style home with Italianate updates. Features 5 ensuite bedrooms, 2 new HVAC systems, a large veranda, and custom kitchen cabinetry. Beautiful hardwood floors and period details are preserved. Furnishings negotiable.

Cozy 2 bed/1 bath cottage in Madison's Historic District. Updated kitchen with quartz countertops, new appliances & flooring. Metal roof, walkout basement, off-street parking. Perfect for those seeking charm & convenience.

Historic downtown Madison live-work space! This 2-story building boasts a commercial/specialty district area downstairs & a private upstairs apartment with living, dining, bedroom, and bath. Totally remodeled, with endless possibilities as retail, office, or apartments. Includes 2 additional 1-bedroom apartments.

Charming 2-bedroom, 1-bath historic shotgun home in a fantastic location. Minutes from downtown festivals, perfect for AirBnb. Recent updates include new flooring, furnace, and AC.

L-shaped lot with approx 200 ft frontage on Clifty Drive. Includes 2 parcels. City utilities available. Suitable for those seeking a large lot with development potential.

Stately colonial home on ~2.5 acres across from Clifty Falls State Park. 5 bedrooms, 2.5 baths, hardwood floors, 3 fireplaces, oversized 3-car garage, and multiple outbuildings. Perfect family retreat!

Historic home in downtown Madison with modern renovations. Features updated kitchen, spacious main bedroom, full bathroom, and rare off-street parking. Perfect for those seeking historic charm with modern conveniences.

High traffic, commercial property located on Madison's hilltop. Zoned General Business. All city utilities available. One parcel.

Two contiguous downtown Madison lots offer endless possibilities. Build two homes or combine for a larger property. All city utilities available. Zoned HDR. Sold together.

Amazing updated home in Miles Ridge! New roof, gutters, exterior doors, deck, flooring, paint, light fixtures, stainless appliances, granite counters, vanities, HVAC & ductwork! Open concept living, 4 large bedrooms, 3.5 baths, flex/den, & office. A must-see!

Move-in ready 3 bed, 2 bath Federal style home in Madison's oldest neighborhood. Features original hardwood floors, double parlor, cozy kitchen, and private courtyard. Recent updates throughout.

80 acre farm in Southern Indiana with development potential. 50+ acres tillable, wooded areas, creek, 1800s barn, city utilities. Ideal for those seeking a blend of nature and development opportunity.

Beautiful open floor plan home on Sunrise Golf Course with separate living quarters. Main house features 4 bedrooms, 4 bathrooms, finished basement, 2-car garage, inground pool, and hot tub. Additional quarters include 1450 sq ft, 2 beds, 2 baths, full kitchen, and 1-car garage. Plenty of storage.

Clean 4 BR 2 BA home across from Clifty Falls State Park. Features a covered porch, fenced backyard, 2-car garage, and storage building. Close to Rucker Sports Complex and shopping. Possession at closing.

10 acres near Madison, IN's historic downtown. Includes 2 homes (one renovated, one needing work), a garden area, and 8.5 acres of vacant land. Potential for RV parking, hotel, short-term rentals, or multi-family housing. Requires zoning approval for development.

Vacant lot in Historic Madison, IN. Potential to combine with adjacent properties (1137, 1127, 1131, 1100 Walnut). Ideal for development or expansion.

1131 Walnut Street is a historic duplex in Madison, Indiana, needing interior renovations. It features charming 19th-century architecture and is close to downtown and the Ohio River. Ideal for those seeking a fixer-upper with potential in a quaint river town.

Fantastic investment opportunity! 3-unit residential rental property with 2-car garage in downtown Madison. Features two 1-bedroom apartments, one efficiency unit, and a shared utility room with coin-operated washer/dryer. Great rental income potential!

Almost 9 acres available in Historic Madison, IN. Combine with 1131, 1127, and 1100 Walnut Street for a larger property.

Former dental office built in 1982, vacant since 2001, ready for redevelopment. Ideal for investors or entrepreneurs seeking a versatile space.

Brick 2-bedroom, 1-bath home with a new roof, new atrium door, and new tub/shower surround. Features a 24x30 garage with 100 amp service and commercial lighting. Needs TLC.

Total Rehab Historic Folk-Victorian home. A must-see!

Beautiful 3 bed, 2 bath home on scenic hilltop. Remodeled kitchen, hardwood floors, soaring ceilings, new roof, energy-efficient heat pump, 2-car garage, and safe basement. Perfect blend of modern updates and classic appeal.

Beautiful 3 bed, 2 bath home with a new roof! Located on a quiet street near restaurants, schools, and a golf course. Features a brick fireplace, spacious patio, and large front porch. Perfect for entertaining or enjoying peaceful evenings.

Charming 19th-century home in historic Madison, Indiana. Short walk to downtown, Ohio River, and Heritage Trail. Potential for B&B or expansion with adjacent parcels.

Two adjacent downtown Madison lots (0.326 acres total) ideal for investors or homeowners. Build two homes or one large home. All city utilities available. Zoned HDR. Sold together only.

Beautiful, well-kept home in DOWNTOWN Madison! Enjoy Main St access & adjacent John Paul Park. Features 2 bedrooms, top-of-the-line galley kitchen, bamboo flooring, & potential attic expansion. Low utilities! Off-street parking & 1-car garage. Perfect for those seeking downtown convenience and character.

Charming 3-bedroom, 2-bath ranch with gleaming hardwood floors, granite countertops, and a fenced-in backyard. Includes a 1-year home warranty and a $2,000 appliance upgrade allowance. Perfect for those seeking comfort and style in a desirable neighborhood.

Spacious 4-bedroom, 2.5-bathroom home with eat-in kitchen, stainless steel appliances, high ceilings, and master suite with walk-in closets, jetted tub, and walk-in shower. Features a covered porch, large deck, corner lot, irrigation system, two heat pumps, Jack and Jill bathroom, huge driveway, and 3-car garage. Ideal for families.

This rumble stone row house is part of Madison's historic district which was recognized as "Best Small Town in the Midwest". Step inside to a...

Discover a fantastic investment opportunity with this 3-unit residential and 2 car garage rental property conveniently located in downtown Madison and minutes from the Madison...

Charming home on corner lot. This home offers 3 bedroom and 1 full bath. Eat-in kitchen, spacious family room, two-car detached garage, and storage shed....

Discover a fantastic investment opportunity with this 3-unit residential and 2 car garage rental property conveniently located in downtown Madison and minutes from the Madison...

Brittany’s Brick Oven Pizza, “B-Bop’s”, is a THRIVING pizza parlor, in a community that demands more! As a highly recognized champion of brick oven pizza,...