Madison, IN Homes for Sale under $400,000

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  /80

  $275,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,154 Sq Ft

  8273 Indiana 56, Madison, IN 47250

  Location is key, and this property sits between two of the "Best Small Midwest Towns in America," according to USA Today. Conveniently located between Madison and Vevay, this versatile 10 acre tract offers a mix of residential, recreational, and small business potential. The parcel features about 1,100 feet of State Road 56 frontage and roughly 100 feet on E Splinter Ridge Road. A paved road that

  

  Brad Garrison

  Whitetail Properties

  (812) 561-6963

  8273 Indiana 56, Madison, IN 47250
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  /93

  $275,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,154 Sq Ft

  8273 State Road 56, Madison, IN 47250

  Location is key, and this property sits between two of the Best Small Midwest Towns in America, according to USA Today. Conveniently located between Madison and Vevay, this versatile 10 acre tract offers a mix of residential, recreational, and small business potential. The parcel features approximately 1,100 feet of State Road 56 frontage and about 100+ feet of frontage on E Splinter Ridge Road.

  

  Brad Garrison

  Whitetail Properties Real Estate

  (317) 701-8655

  8273 State Road 56, Madison, IN 47250
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  /22

  $115,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  5653 W 400 N, Madison, IN 47250

  5.03 scenic acres with a pond in a tranquil setting near Madison. Property includes an existing structure being sold as-is. Excellent opportunity for redevelopment, new construction, or renovation. Beautiful natural surroundings with water feature, privacy, and convenient access to Madison's historic downtown, riverfront, and outdoor recreation.

  

  Candice Ritchie

  Green Tree Real Estate Services

  (812) 370-8110

  5653 W 400 N, Madison, IN 47250
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  /44

  $232,500

  $32K PRICE DROP

  • Land
  • 18.23 Acres
  • $12,754 per Acre

  3500 E Lemon Rd, Madison, IN 47250

  Beautiful weekend retreat with a fully usable cabin. This great weekend getaway is perfect for a family camp or the annual deer camp. The off-grid cabin is powered by a generator with inverter/charger battery backup, composting toilet, woodburning stove, mini split AC/heat unit and a 100-gallon cistern tank for water. The property has a nice entrance with a gravel lane and parking. The terrain

  Rob Haubry Geswein Farm & Land Realty, LLC

  3500 E Lemon Rd, Madison, IN 47250
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  /21

  $390,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  113 Jefferson St, Madison, IN 47250

  I am pleased to present an exceptional investment opportunity featuring two successful, side-by-side Airbnb properties in the heart of downtown Madison, Indiana. These one-level homes are within walking distance of all downtown amenities and are being offered for sale separately, however the opportunity to purchase 2 successful Airbnb properties side-is-side is very rare!Key highlights of

  Jackie Armel Greene Coldwell Banker Harrell & Asso

  113 Jefferson St, Madison, IN 47250
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  /19

  $299,800

  • 4 Beds
  • 2 Baths
  • 1,176 Sq Ft

  330 W State St, Madison, IN 47250

  This wonderful home was in one family for the last 60 + years! It has been fully renovated and ready for the next family to enjoy for decades to come! Inside the lower level has new flooring, paint, bath fixtures and new clothes W/D. Upstairs has all new appliances, granite counters, completely new full bathroom with tile shower, fresh paint and new light fixtures. Outside the siding has been

  Robin Mingione eXp Realty, LLC

  330 W State St, Madison, IN 47250
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  /43

  $232,500

  $32K PRICE DROP

  • 0.5 Baths

  3500 Lemon Rd, Madison, IN 47250

  Beautiful weekend retreat with a fully usable cabin. This great weekend getaway is perfect for a family camp or the annual deer camp. The off-grid cabin is powered by a generator with inverter/charger battery backup, composting toilet, woodburning stove, mini split AC/heat unit and a 100-gallon cistern tank for water. The property has a nice entrance with a gravel lane and parking. The terrain

  Rob Haubry Geswein Farm & Land Realty

  3500 Lemon Rd, Madison, IN 47250
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  /25

  $275,000

  $15K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft

  423 Mill St, Madison, IN 47250

  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,

  Christi Sauley-Kernen F.C. Tucker/Scott Lynch Group

  423 Mill St, Madison, IN 47250
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  /32

  $324,900

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  610 W 2nd St Unit 1, Madison, IN 47250

  Beautiful first floor Federal style condominium blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today'sBest 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

  Brenda Eversole Century 21 River Valley

  610 W 2nd St Unit 1, Madison, IN 47250
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  /29

  $389,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 837 Sq Ft

  1010 E 1st St, Madison, IN 47250

  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

  Brenda Eversole Century 21 River Valley

  1010 E 1st St, Madison, IN 47250
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  /20

  $234,900

  • 2 Beds
  • 2 Baths
  • 1,514 Sq Ft

  931 W Main St, Madison, IN 47250

  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

  Tony Bilz F.C. Tucker/Scott Lynch Group

  931 W Main St, Madison, IN 47250
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  /17

  $199,000

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  2527 Franks Dr, Madison, IN 47250

  This beautifully updated home offers comfort, function, and thoughtful improvements throughout. Major updates completed in summer 2025 include a new HVAC system (inside and out), freshly updated flooring, sealed driveway, and a refreshed kitchen with brand-new appliances. The converted garage now serves as a spacious dining area, adding valuable living space and a large built-in storage closet

  Rachel Avery

  2527 Franks Dr, Madison, IN 47250
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  /44

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,156 Sq Ft

  195 Autumnwood Ln, Madison, IN 47250

  Welcome to Autumnwood Estates! Enjoy this beautifully maintained home that offers the perfect blend of comfort, space, and privacy in one of Madison's desired neighborhoods! Featuring 3 bedrooms, 2 bathrooms, and a bonus living room, there is plenty of room for relaxing, entertaining, or creating the perfect home office or play space.The oversized laundry room provides additional storage and

  Sarah Hollihan eXp Realty, LLC

  195 Autumnwood Ln, Madison, IN 47250
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  /22

  $399,900

  • 6 Beds
  • 4 Baths
  • 1,950 Sq Ft

  117 Jefferson St, Madison, IN 47250

  I am pleased to present an exceptional investment opportunity featuring two successful, side-by-side Airbnb properties in the heart of downtown Madison, Indiana. These one-level homes are within walking distance of all downtown amenities and are being offered for sale separately, however the opportunity to purchase 2 successful Airbnb properties side-is-side is very rare!Key highlights of

  Jackie Armel Greene Coldwell Banker Harrell & Asso

  117 Jefferson St, Madison, IN 47250
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  /12

  $215,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  715 Walnut St, Madison, IN 47250

  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

  Jason Clifton F.C. Tucker/Scott Lynch Group

  715 Walnut St, Madison, IN 47250
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  /40

  $379,000

  • 3 Beds
  • 1.5 Baths
  • 2,164 Sq Ft

  507 E Main St, Madison, IN 47250

  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

  Brenda Eversole Century 21 River Valley

  507 E Main St, Madison, IN 47250
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  /49

  $384,900

  • 3 Beds
  • 2.5 Baths
  • 2,570 Sq Ft

  508 Jefferson St, Madison, IN 47250

  Beautiful Brick Federal style home built in 1847 with gas light front door entry. In the heart of historic downtown Madison, with original woodwork and flooring. Double parlor accented with arched doors and gingerbread. Home showcases a curved hallway staircase with stained glass window and door, which also leads to the upstairs covered porch at the landing. For convenience, an additional back

  Brenda Eversole Century 21 River Valley

  508 Jefferson St, Madison, IN 47250
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  /41

  $349,000

  • 2 Beds
  • 1.5 Baths
  • 1,774 Sq Ft

  712 E Main St, Madison, IN 47250

  This captivating stone residence, built in 1839, offers a whimsical blend of timeless elegance and modern comfort. Step through the beautiful Dutch door at the front stoop into a sanctuary rich with character and history. Original chestnut and old-growth pine flooring whisper stories of bygone eras throughout the home. The foyer offers an inviting transition, leading to the parlor and dining room

  Jessica Butler Legacy Land Use & Realty

  712 E Main St, Madison, IN 47250
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  /45

  $218,000

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,299 Sq Ft

  2131 Seneca Dr, Madison, IN 47250

  Welcome to this charming all-brick home hilltop home, offering rare privacy as it backs directly up to the State Park. This 3-bedroom, 2-bath property is full of character and ready for your personal touch. The primary suite features its own private full bath, while the home offers multiple living spaces including a formal dining room, a cozy kitchen with an additional dining area, and a spacious

  Jim Pruett eXp Realty, LLC

  2131 Seneca Dr, Madison, IN 47250
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  /9

  $175,000

  $24K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  822 Green Rd, Madison, IN 47250

  Large home with many options, located across from the Sports Complex on Madison’s hilltop. Large bedrooms with room to grow. Close to schools, shopping, and downtown. This property has many possibilities- come take a tour and put your imagination to work...investment property or family home. Updates include: New roof (2023), Floor joist repairs, new duct work, and new laminate flooring

  Candice Fulk McDole Century 21 River Valley

  822 Green Rd, Madison, IN 47250
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  /32

  $354,900

  • 4 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  7526 E Riverside Dr, Madison, IN 47250

  This beautiful home offers two exceptional features: Stunning river views and direct access to the Ohio River. From the deck, you can enjoy watching boats and barges pass by against the peaceful backdrop of the hills of Kentucky. The property also boasts additional wonderful outdoor amenities, including a fenced yard, a swimming pool, and an additional lot providing plenty of space for enjoyment.

  Jackie Armel Greene Coldwell Banker Harrell & Asso

  7526 E Riverside Dr, Madison, IN 47250
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  /32

  $239,000

  $11K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,852 Sq Ft

  2159 Lanier Dr, Madison, IN 47250

  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

  Tasha Jenkins Century 21 River Valley

  2159 Lanier Dr, Madison, IN 47250
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  /40

  $374,900

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,410 Sq Ft

  1421 Cherokee Ct, Madison, IN 47250

  Spacious 5-bedroom, 3-bath home offering comfort, space, and a peaceful setting. The open floor plan features vaulted ceilings, abundant natural light, and two cozy woodburning fireplaces. The kitchen includes granite countertops, a breakfast bar, and plenty of cabinet space for storage. Enjoy multiple living areas including a family room with built-in shelving and a finished basement with

  Nancy Sobeck ReaL Broker, LLC

  1421 Cherokee Ct, Madison, IN 47250
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  /66

  $299,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,575 Sq Ft

  6734 N Sr 7, Madison, IN 47250

  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

  Jim Pruett EXP Realty LLC

  6734 N Sr 7, Madison, IN 47250
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  /30

  $289,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft

  718 W 3rd St, Madison, IN 47250

  Built in 2023, this stunning 1,330 sq ft modern home perfectly blends contemporary comfort with the charm of downtown living. Located in the heart of Madison’s historic district, you’ll enjoy being just steps from boutique shops, local restaurants, wineries, and the city’s beloved festivals and year-round events. This newer construction features a bright, open-concept floor plan filled with

  Christi Sauley-Kernen F.C. Tucker/Scott Lynch Group

  718 W 3rd St, Madison, IN 47250
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  /17

  $225,000

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft

  7132 W Sr 256, Madison, IN 47250

  Quaint 2-bedroom, 1-bath home situated on 2 peaceful acres, offering space and versatility both inside and out. The home features a large living room with newer carpet and updated windows that provide great natural light. A full unfinished basement offers excellent storage or potential for future expansion. Outside, you’ll find a nice-sized barn and a detached garage, ideal for equipment,

  Nancy Sobeck ReaL Broker, LLC

  7132 W Sr 256, Madison, IN 47250
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  /40

  $329,900

  • 2 Beds
  • 2.5 Baths
  • 1,991 Sq Ft

  612 W 2nd St Unit 4, Madison, IN 47250

  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

  Brenda Eversole Century 21 River Valley

  612 W 2nd St Unit 4, Madison, IN 47250
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  /27

  $219,900

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  1202 Esplano Dr, Madison, IN 47250

  Tucked away on the largest lot on quiet Esplano Drive, this beautifully updated 3-bedroom, 1-bath home offers the perfect blend of privacy, convenience, and small-town charm. Featuring an open floor plan, bonus room, spacious laundry room, new flooring, new appliances, new heating and air, and a new roof, this move-in-ready property is designed for comfortable living. Enjoy a paved driveway with

  Van Crafton Coldwell Banker Harrell & Asso

  1202 Esplano Dr, Madison, IN 47250
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  /27

  $295,900

  $29K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  2816 N Rykers Ridge Rd, Madison, IN 47250

  Charming all-brick home offering 1,380 sq ft of comfortable living space, featuring 2 bedrooms and 1.5 baths. This well-maintained property blends classic character with important modern updates, including a new roof, HVAC system, and flooring—all completed in 2024. Step inside to a warm and inviting living room complete with a fireplace insert and built-in bookcases, perfect for cozy evenings

  Christi Sauley-Kernen F.C. Tucker/Scott Lynch Group

  2816 N Rykers Ridge Rd, Madison, IN 47250
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  /18

  $259,900

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  2309 Taylor St, Madison, IN 47250

  All brick 4 bedroom, 2 full bath on the hilltop next to the Junior High School. Fenced-in backyard. New roof in 2024. New windows in 2023, except for the ones in the family room. Remodeled bath in 2025. Detached 2.5-car garage with workshop, insulated and heated. Carport in front.

  Keith Mahoney Century 21 River Valley

  2309 Taylor St, Madison, IN 47250
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  /57

  $387,500

  $60K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,850 Sq Ft

  6164 Mckay Rd, Madison, IN 47250

  NEW PRICE: ASKING $387,500. The Ultimate Privacy! Located close to Vevay (5-7 Miles) and Madison (20 Miles). Nature Lover's Dream! Walking or Quad Trails through many trees. Wildlife galore, Wild Turkeys, Deer, Birds, Fishing Pond, all on 11.59 Wooded Acres. Country Living with a Secluded Location. Includes A Custom Built Rustic 3 BR, 1 Full 2(1/2) Baths 1.5 Story home with Metal Roof (2018)

  Pamela Ginder RE/MAX Advantage 1

  6164 Mckay Rd, Madison, IN 47250
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  /48

  $379,900

  $19K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,652 Sq Ft

  518 Jefferson St, Madison, IN 47250

  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

  Scott Lynch F.C. Tucker/Scott Lynch Group

  518 Jefferson St, Madison, IN 47250
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  /26

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  115 Walnut St, Madison, IN 47250

  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,

  Tony Bilz F.C. Tucker/Scott Lynch Group

  115 Walnut St, Madison, IN 47250
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  /17

  $309,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  1041 Rabbit Ln, Madison, IN 47250

  Beautifully maintained brick home located on Madison’s desirable hilltop! This 3-bedroom, 2 full bath home features an open-concept kitchen, dining, and living area with vaulted ceilings, creating a bright and spacious feel throughout. The large primary suite offers a walk-in closet, soaking tub, and separate walk-in shower. A welcoming foyer entrance adds to the home’s charm and functionality.

  Patrick Lynch F.C. Tucker/Scott Lynch Group

  1041 Rabbit Ln, Madison, IN 47250
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  /40

  $184,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  716 Walnut St, Madison, IN 47250

  Step into timeless charm with this beautifully renovated 2-bedroom, 1-bath cottage-style in the heart of Historic DowntownMadison. Built ca. 1930 by a local millworker, this home blends original character with modern updates. The covered porchshelters the front door, which opens into a foyer with a coat closet, and a spacious living room featuring a cozy fireplace.Enjoy refinished

  John Demaree F.C. Tucker/Scott Lynch Group

  716 Walnut St, Madison, IN 47250
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  /36

  $310,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  401 Maple Hill Dr, Madison, IN 47250

  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

  Stephanie Brawner Coldwell Banker Harrell & Asso

  401 Maple Hill Dr, Madison, IN 47250
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  /22

  $250,000

  • 1 Bed
  • 1 Bath
  • 868 Sq Ft

  1057 W Main St, Madison, IN 47250

  Historic charm meets modern convenience right on Main Street in downtown Madison! This thoughtfully updated bungalow blends timeless character with tasteful improvements while preserving many original features, including the beautiful hardwood floors throughout much of the home. The spacious living room offers the perfect setting to showcase your antique furnishings and create a warm, inviting

  Andrew Flora 1 Percent Lists Indiana Real Estate

  1057 W Main St, Madison, IN 47250
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  /16

  $399,000

  $100K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,082 Sq Ft

  109 Central Ave, Madison, IN 47250

  Rare chance to own property directly across from Historic Downtown Madison festival hub Bicentennial Park, and close to the River Walk. This property sits in the heart of the action, offering unparalleled access to all the charm and activities downtown has to offer. The house itself is in need of renovation, but it provides a blank slate for any vision. Whether you dream of restoring the existing

  Alaina Tandy Century 21 River Valley

  109 Central Ave, Madison, IN 47250
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  /7

  $199,900

  • 1 Bed
  • 1 Bath
  • 1,040 Sq Ft

  512 E Main St Unit 1, Madison, IN 47250

  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,

  Patrick Lynch F.C. Tucker/Scott Lynch Group

  512 E Main St Unit 1, Madison, IN 47250
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  /13

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1046 Michigan Rd, Madison, IN 47250

  Location, Privacy, and Convenience!!! This well-maintained and nicely updated 3-bedroom, 2-bathroom home offers an impressive location. Situated behind The Fairmount House of Madison and backing up to Fairmount Drive, the property provides excellent privacy while being conveniently located at the edge of the hilltop, and just two miles from historic downtown Madison. The home features genuine

  Jackie Armel Greene Coldwell Banker Harrell & Asso

  1046 Michigan Rd, Madison, IN 47250

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