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833 & 835 W Main Street, Madison
$759,900
3 Beds ⋅ 3 Baths ⋅ 2026012471 MLS ⋅ ACTIVE Status
Historic Downtown Madison – Live, Work & Invest! This distinctive mixed-use property offers the perfect blend of commercial opportunity and upscale downtown living. Featuring approximately 3,233 sq. ft. of main-level retail space with an extensive remodel, the property also includes a luxurious second-floor residence with its own private entrance. The inviting residence features 3 bedrooms, 2 bathrooms, beautiful hardwood floors, an updated kitchen, and an open floor plan. Additional amenities include off-street rear parking and an all-brick detached garage. Located in the heart of historic downtown Madison, this unique property offers the opportunity to enjoy a spacious, upscale residence while operating a business or generating rental income. An exceptional opportunity for an owner-occupant or investor seeking character, convenience, and versatility in a prime downtown location. Call today for additional details!

833 & 835 W Main Street, Madison

532 Miles Ridge Road, Madison
$349,900
3 Beds ⋅ 3 Baths ⋅ 2026012114 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated 3-bedroom, 2.5-bath ranch home in the desirable Miles Ridge neighborhood! Situated on a spacious corner lot, this inviting home offers a thoughtful split-bedroom floor plan, fresh finishes, and plenty of room to enjoy both inside and out. The heart of the home is the newly finished kitchen, featuring refinished cabinetry, stunning quartz countertops, a farmhouse sink, and brand-new stainless steel appliances. The dining area features access to a covered back porch and a newly fenced-in yard, perfect for entertaining family and friends! The home features many more updates, including newly finished bathrooms, newly painted trim and walls throughout the home, new flooring through the majority of the home, fresh landscaping, and more. With its desirable location, corner-lot setting, extensive updates, and inviting floor plan, this Miles Ridge gem is truly move-in ready and waiting for its next owner. Schedule your showing today!

532 Miles Ridge Road, Madison

2020 Galway Trail S, Madison
$365,000
3 Beds ⋅ 2 Baths ⋅ 2026011948 MLS ⋅ ACTIVE Status
Interior Features: Move-In Ready Updates: Enjoy peace of mind with a brand-new HVAC system and fresh interior paint throughout. Thoughtful Layout: The popular split floor plan provides maximum privacy for the primary suite. Refined Finishes: Highlights include rich wood flooring, elegant crown molding, custom cabinetry, and sleek stainless steel appliances. Outdoor Living & Yard: Outdoor Oasis: Step out onto the covered porch and spacious brick patio—perfect for entertaining or quiet morning coffee. Fully Equipped Yard: The large backyard features raised garden beds ready for your green thumb and a charming yard barn for extra storage. Whether you're relaxing inside surrounded by high-end finishes or enjoying the spacious backyard, this move-in-ready home has it all. Schedule your showing today before it's gone!

2020 Galway Trail S, 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

239 Sunrise Drive, Madison
$399,900
3 Beds ⋅ 3 Baths ⋅ 2026011848 MLS ⋅ ACTIVE Status
Welcome to 239 Sunrise Drive in historic Madison, Indiana! Located in desirable Sunrise Falls Estates, this home is nestled in a welcoming community where neighbors are often out walking or cruising by on golf carts. This spacious 3-bedroom, 2.5-bath ranch offers approximately 2,580 sq ft of finished living space with plenty of room to gather and entertain. The main level features a spacious kitchen with an island and pantry, a formal dining area, and inviting living spaces filled with natural light. A desirable split-bedroom floor plan provides privacy, with the primary suite offering a peaceful retreat complete with an updated en-suite bath and dual-sink vanity. Two additional generously sized bedrooms and a full bath complete the main level. The finished lower level offers even more living space and features newly installed laminate flooring. A large family room is anchored by a striking stone wood-burning fireplace, creating the perfect setting for movie nights, entertaining, or simply relaxing at home. A convenient half bath and laundry area are located just off the family room, while the adjacent foyer provides direct access to the spacious two-car garage. Outside, enjoy generous front and rear decks along with a newly fenced yard, ideal for pets, play, entertaining, or simply enjoying the outdoors. A newly added storage shed provides additional space for lawn equipment, tools, bikes, and more. Schedule your private showing today!

239 Sunrise Drive, Madison

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

221 Miles Ridge Road, Madison
$369,900
3 Beds ⋅ 3 Baths ⋅ 2026011730 MLS ⋅ ACTIVE Status
Welcome to this spacious 3-bedroom, 2.5-bath home situated on a large lot surrounded by abundant wildlife. With numerous recent updates and plenty of room to relax and entertain, this property offers comfort, charm, and versatility. Recent improvements include a roof approximately two years old, a new heating unit, and fresh paint throughout. The bathrooms have been refreshed with new vanities and luxury vinyl plank flooring. The bright eat-in kitchen features abundant cabinetry, plenty of natural light, and newer stainless-steel appliances. A formal dining room provides additional space for gatherings and special occasions. The large family room is a standout feature, offering vaulted ceilings and a cozy fireplace—perfect for entertaining guests or relaxing at the end of the day. Upstairs, a bonus area accessed through the bedroom closet offers exciting potential and could be finished as an expanded closet, home office, hobby space, or additional room. Step outside to enjoy the spacious deck, which is partially covered and provides a wonderful setting for outdoor dining, relaxing, and watching the surrounding wildlife. With its generous lot, thoughtful updates, and flexible living spaces, this home has so much to offer.

221 Miles Ridge Road, Madison

522 Quail Ridge Court, Madison
$429,900
3 Beds ⋅ 3 Baths ⋅ 2026011214 MLS ⋅ ACTIVE Status
This full-brick home offers exceptional curb appeal and is ideally located near the cul-de-sac of a highly sought-after neighborhood. Key features of the home include a covered front porch that leads into a large foyer with beautiful marble flooring, followed by genuine hardwood floors. The living area opens directly into a stunning kitchen equipped with granite countertops, a large center island, extensive cabinet space, two pantries, and a separate den that is perfect for a home office. The upper level features three bedrooms, including a primary suite with a large bathroom and a walk-in closet with custom built-in shelving. The outdoor space is equally as nice. The kitchen and Liv Rm opens onto a private, spacious back deck that overlooks a peaceful, park-like backyard with mature trees, providing privacy, shade and tranquility. There is also a finished climate-controlled spacious room above the garage that offers excellent versatility for a recreation room, additional office, guest space, or storage. Many recent important updates - New roof in 2019, new Geothermal heat and air in 2022, and new water heater this month (Aug 2026). Check out this wonderful home at your earliest opportunity, because homes this nice don't come along very often!!

522 Quail Ridge Court, Madison

11945 N JEFFERSON Road, Madison
$254,900
3 Beds ⋅ 2 Baths ⋅ 2026010401 MLS ⋅ ACTIVE Status
Looking for peaceful country living with room to spread out? This 3 BR 2 BA home sits on 1.35 acres in rural Madison,offering the opportunity to enjoy a little extra space, fresh air, and a more relaxed lifestyle. Inside you'll find a comfortable floor plan with updated laminate flooring, a spacious living area dividing the master suite from the 2 additional BR's providing flexibility for family, guests, a home office or hobbies. Step outside to enjoy the covered front porch, perfect for relaxing evenings or the surrounding country setting. Multiple storage buildings provide useful space for tools, lawn equipment, gardening supplies, and outdoor projects. The rolling hill and backyard trees provide a relaxing backyard oasis. This property offers a combination of indoor comfort and outdoor space. If you have been looking for a home with a little breathing room, space for pets and hobbies and the feel of country living close to town, schedule you showing today!

11945 N JEFFERSON Road, 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

4466 N SR 62, Madison
$759,900
7 Beds ⋅ 5 Baths ⋅ 202609873 MLS ⋅ ACTIVE Status
Excited to share details regarding this exceptional property situated on over 5 acres just on the edge of town. Located only 2 miles from the hub of Madison's hilltop and minutes from vibrant downtown Madison—recently rated the #1 Best Small Town in the Midwest by USA Today—this home offers an incredible amount of space and versatility. The interior features a gorgeous custom kitchen designed for entertaining, complemented by beautiful genuine hardwood floors throughout the main living area. The primary suite includes a modern soaking tub, tiled walk-in shower, and double vanities for ultimate comfort. The main level also offers 3 more bedrooms, a full bathroom, a half bath for guests, and a laundry room. Upstairs, you will find 2 large loft areas, 3 additional bedrooms, and a very spacious full bathroom. The full finished walk-out basement provides a very large Family room, a 2nd laundry room, ample storage, a play room, a safe room, and an additional full bathroom. Outdoor amenities are equally impressive, featuring large covered front and back porches with updated Trex flooring. The fenced backyard includes a playset and leads to 3 acres of wooded land. Additionally the property includes 2 detached garages: one is insulated, with rubber mat flooring across the entire floor, and has a heat & air system, while the 2nd features a 12-foot door perfect for an RV or boat. This dream home has so much to offer. Schedule your viewing today!

4466 N SR 62, Madison

2904 N Rykers Ridge Road, Madison
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 202608456 MLS ⋅ ACTIVE Status
Welcome to an extraordinary property in the highly desirable Rykers Ridge area of Jefferson County, Indiana—where refined living meets breathtaking natural beauty. Situated on 57 pristine acres of rolling pasture & wooded acreage, this private retreat offers a rare combination of elegance, tranquility, & space. From the moment you arrive, the home’s timeless charm is evident in its inviting covered front porch & wraparound veranda—perfect for enjoying sweeping views & peaceful surroundings. Designed for both relaxation & entertaining, the outdoor spaces include a covered back porch & patio, all immersed in a serene landscape rich with wildlife. Inside, impeccable craftsmanship shines through with high ceilings, exquisite cabinetry, & two striking fireplaces that anchor the home’s sophisticated living spaces. The residence features two beautifully appointed kitchens, ideal for seamless multi-generational living or hosting guests in style with dedicated private quarters. Offering 4 spacious bedrooms & 2 spa-inspired bathrooms, every detail has been curated to provide comfort & luxury. A detached two-car garage with lean-to & a barn add both function & versatility to this remarkable property. Located just minutes from the charm & culture of Madison, Indiana, this estate delivers an unparalleled lifestyle of privacy, beauty, & elevated country living. If you’ve been dreaming of space, privacy, & a place to truly unwind—this Rykers Ridge property in Jefferson County is it.

2904 N Rykers Ridge Road, Madison

4502 N SR 7, Madison
$649,000
4 Beds ⋅ 3 Baths ⋅ 202607868 MLS ⋅ ACTIVE Status
Check out this truly rare opportunity in Madison, where you can enjoy the convenience of being just minutes from town while owning over 6 acres of private, picturesque land. Properties like this are hard to find, offering the accessibility and peaceful country living. This stunning home lives up to the hype with beauty, quality, space, and a sense of tranquility that’s hard to match. Inside, you’ll find beautiful living space filled with custom finishes and intricate detailing. From crown molding and unique ceilings with ambient lighting to the impressive fireplace, every element has been thoughtfully designed to impress. The versatile floor plan offers flexibility to fit your lifestyle, with options for a first-floor bedroom or office, and additional rooms upstairs that could serve as a nursery or sitting area. Entertaining is a breeze with a formal dining room, breakfast nook, and open-concept main living areas that flow seamlessly together. In addition to the attached 2+ car garage, a detached 2-car pole barn provides ample storage for vehicles, hobbies, or recreational equipment. If you're seeking privacy, high-quality finishes, and room to roam—all while staying close to town—this exceptional property is truly a must-see.

4502 N SR 7, 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

422 St Michaels Avenue, Madison
$464,500
4 Beds ⋅ 4 Baths ⋅ 202607755 MLS ⋅ ACTIVE Status
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

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