Madison, IN Homes for Sale under $500,000

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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

  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

  8273 State Road 56, Madison, IN 47250
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  /104

  $459,000

  • 1 Bed
  • 1 Bath
  • 1,233 Sq Ft

  2945 N Greenbrier Rd, Madison, IN 47250

  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.

  

  Greg Taylor

  Trueblood Real Estate

  2945 N Greenbrier Rd, Madison, IN 47250
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  /47

  $214,500

  $50K PRICE DROP

  • Land
  • 18.23 Acres
  • $11,766 per Acre

  3500 E Lemon Rd, Madison, IN 47250

  Escape to your own private outdoor paradise with this beautiful recreational property featuring a brand-new Amish-Built log cabin constructed with exceptional craftmanship and quality materials. Built for comfort and durability, this solid log cabin comfortably sleeps up to 6 people and offers many of the conveniences of home while allowing you to enjoy the peace and privacy of nature.The

  Rob Haubry Geswein Farm & Land Realty, LLC

  3500 E Lemon Rd, Madison, IN 47250
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  /6

  $299,000

  • Land
  • 41.91 Acres
  • $7,134 per Acre

  0 Cr 925 S 350w Unit 207830, Madison, IN 47250

  A 41.91 Acre Wooded building site with electric hook up and private drive to a cleared ready to build site.Public water available. Septic perk test available. This is a great get away site to hunt, camp or build your dream property away from the Public. Call to see this today !

  John Lucas RE/MAX Preferred Choice

  0 Cr 925 S 350w Unit 207830, Madison, IN 47250
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  /21

  $375,000

  $15K PRICE DROP

  • 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 Greene Coldwell Banker Harrell & Asso

  113 Jefferson St, Madison, IN 47250
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  /46

  $489,900

  • 4 Beds
  • 3.5 Baths
  • 3,348 Sq Ft

  5300 E Wolf Run Rd, Madison, IN 47250

  Rare Find! Beautiful Home in a Spectacular Park-Like Setting! Fall in love with this beautifully updated 4-bedroom, 3.5-bathroom retreat tucked into a private, wooded backdrop.Interior Highlights:Brand-new hardwood flooring & fresh, modern paint throughout.Fully updated kitchen—the true heart of the home.Bright, airy layout with generous bedroom sizes.Full, walk-out basement

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

  5300 E Wolf Run Rd, Madison, IN 47250
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  /33

  $309,900

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  2330 Cragmont St, Madison, IN 47250

  Welcome home! This move-in ready property combines many big updates, a thoughtful layout, and an ideal location just minutes from schools, shopping, and the charm of historic downtown Madison. Every detail reflects years of meticulous care, making this home ready for its next owner. Step inside to discover a welcoming floor plan, featuring a comfortable living room, an additional family room

  Kelsey Shaw F.C. Tucker/Scott Lynch Group

  2330 Cragmont St, 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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  /28

  $384,900

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,674 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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  /27

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  2836 Springwood Dr, Madison, IN 47250

  Here's your chance! Back on the market at no fault of the seller; buyer financing fell through. Don't wait! This charming 3-bedroom, 2-full-bath home offers flexible living with a versatile bonus room that could serve as a primary suite, formal dining room, or family room - the choice is yours. Enjoy low-maintenance laminate flooring throughout, plus a modern kitchen featuring six-year-old

  Jacqueline Ober Exp Realty

  2836 Springwood Dr, Madison, IN 47250
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  /39

  $369,900

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  515 N Hereford Ln, Madison, IN 47250

  Looking for space, storage, and lake access? This well-maintained 4-bedroom, 2 full bath home offers a huge living room filled with natural light, creating the perfect gathering space for family and friends. The adjacent eat-in kitchen provides plenty of room for everyday meals and entertaining. Enjoy access to the popular Hereford Lake, where you can spend your days fishing, kayaking, or simply

  Austin Ketcham eXp Realty, LLC

  515 N Hereford Ln, 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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  /44

  $390,000

  $9K PRICE DROP

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

  195 Autumnwood Ct, 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 Ct, 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 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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  /39

  $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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  /30

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 1,842 Sq Ft

  234 Hargan Dr, Madison, IN 47250

  Don't miss this Bedford stone beauty located on a corner lot in the established Highland Heights neighborhood of Madison. Conveniently situated near Anderson Elementary and just minutes from shopping, restaurants, and other local amenities, this 3 bedroom, 1.5 bath home offers over 1,500 square feet of living space. The spacious living room features a decorative accent wall, while the bonus room

  Cathy Jackson Schuler Bauer Real Estate Services ERA Powered (N

  234 Hargan Dr, 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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  /47

  $474,900

  $65K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,909 Sq Ft

  7877 Upper Dry Fork Rd, Madison, IN 47250

  Welcome to your country oasis in Madison Indiana. This 4-bedroom, 3.5 bath home on 5.92 acres boasts a truly serene living environment. Close to town, but far enough away from the hustle and bustle will make any homeowner truly happy with this location. The pole barn will house any and all toys and the pool/outdoor living space is perfect for all of your summer gatherings.

  Suzanne Pieczonka

  7877 Upper Dry Fork Rd, 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
  • 3,510 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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  /34

  $404,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,127 Sq Ft

  128 West St, Madison, IN 47250

  An extremely rare 2 structure opportunity for OWNER-OCCUPANTS or for INVESTORS looking for an IMMEDIATE INCOME-PRODUCING property - proven AIRBNB GROSS INCOME OF OVER $69k FROM mid 2024-and all 2025 (financials available). The home has been maintained personally by local owners. FULLY FURNISHED with an acceptable offer. You can move right in or continue renting immediately! This beautifully

  Scott Lynch F.C. Tucker/Scott Lynch Group

  128 West St, Madison, IN 47250
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  /43

  $242,900

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  609 Walnut St, Madison, IN 47250

  Turn Key Historic 2 story pre 1900. Just a short walk to the Ohio River entertainment area, as well as the shops of Madison. This walkable community also has a trolly, residents commute by golf cart. Great for Air B&B or several other uses. Tourist community, nice place for a 2nd home. One of just a very few homes that have a garage. Newer HVAC, newer HWH, newer baseboard heat upstairs, newer

  Sue Ann Collins Teamwork Real Estate

  609 Walnut St, 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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  /38

  $489,900

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  212 Saint Michaels Ave, Madison, IN 47250

  Charming old meets new home 1 block from the river and out of the flood plain. Home has been completely updated. 3 bedroom 2.5 bath with beautiful finishes, large closets, 2 decorative fireplaces, oak stairs, new appliances, high-end countertops, new cabinets, new windows, new roof, new water heater, and much, much, more! Large partially fenced yard with 2+ car garage and additional off-street

  JR Harrell Coldwell Banker Harrell & Asso

  212 Saint Michaels Ave, 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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  /31

  $240,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  1460 E Wehner Dr, Madison, IN 47250

  Welcome home to this charming brick ranch located on Telegraph Hill! Conveniently situated just minutes from downtown Madison and Madison Hilltop, you'll enjoy easy access to shopping, dining, entertainment, and everyday amenities. This well-maintained home features 2 bedrooms, 1 full bath, a spacious living room, and a kitchen with a dining area. The cozy family room is highlighted by a

  Scott Lynch F.C. Tucker/Scott Lynch Group

  1460 E Wehner Dr, Madison, IN 47250
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  /27

  $209,900

  $15K 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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  /31

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  9727 E Vernon Ridge Rd, Madison, IN 47250

  Check out this peaceful small homestead waiting for you! A well maintained 3 bedroom, 2 bath home on just over an acre with several fruit trees, berries, garden, chicken coop and more! Home has a nice open concept, wonderful sunroom and good size bedrooms. Updates include new flooring in entry and living areas, all new screens, new clothes washer, wood interior window sills and plans to complete

  Robin Mingione eXp Realty, LLC

  9727 E Vernon Ridge Rd, Madison, IN 47250
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  /18

  $254,900

  $20K 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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  /47

  $359,900

  $39K 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

  $264,900

  $10K PRICE DROP

  • 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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  /39

  $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

  $244,900

  $5K PRICE DROP

  • 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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  /39

  $417,000

  • 3 Beds
  • 2.5 Baths
  • 2,984 Sq Ft

  2660 N Borcherding Rd, Madison, IN 47250

  Picture-Perfect Cape Cod with Exceptional Curb Appeal!Prepare to fall in love with this stunning, light-filled home that perfectly balances traditional charm with spacious functionality.Key Features Include:Stunning Exterior: Beautiful brick-accented front facade, mature landscaping, and an expansive covered front porch designed for relaxing.Spacious Living: Classic Cape Cod

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

  2660 N Borcherding Rd, 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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