Madison, IA Homes

/13
$159,900
- 5 Beds
- 2 Baths
- 1,556 Sq Ft
523 S 2nd St, Winterset, IA 50273

This conversion duplex offers the perfect opportunity to add value and generate strong returns. Located just blocks from downtown Winterset, this property is ideal for house hackers, investors, or anyone looking to expand their portfolio in a growing community. Each unit offers spacious layouts with room for updates and personalization. With separate entrances, utilities, and off-street parking

Ben Grotzke LPT Realty, LLC

523 S 2nd St, Winterset, IA 50273
/20
$450,000 Sold May 14, 2025
- 2,464 Sq Ft
- $183/SF
- 17 Days On Market
- 5 Beds
- 3 Baths
- Built 1905
522 W Green St, Winterset, IA 50273

This stunning two-story home offers 5 bedrooms, 3 full baths, and is packed with charm and detail throughout. Nestled on a corner lot, this property features a fully fenced yard- for pets, play, and privacy. Inside, you'll find spacious living areas with beautiful finishes, ample natural light, and thoughtful design elements. The well- appointed kitchen offers plenty of counter space AND a

Rachel Eller Summerset Realty

522 W Green St, Winterset, IA 50273

/25
Est $191,102 Not Listed For Sale
- 2 Beds
- 1 Bath
- 984 Sq Ft
422 W Filmore St, Winterset, IA 50273

422 W Filmore St, Winterset, IA 50273

/32
$183,000
- 3 Beds
- 1.5 Baths
- 1,192 Sq Ft
409 W Filmore St, Winterset, IA 50273

Welcome to this charming and well-maintained 3-bedroom, 1.5-bath home in a quiet, established neighborhood. The spacious main floor offers abundant natural light, a functional layout, and convenient main floor laundry. The heart of the home is the large kitchen featuring ample cupboard and counter space, a generous walk-in pantry, and a new dishwasher—perfect for everyday living and entertaining.

Misty Darling BH&G Real Estate Innovations

409 W Filmore St, Winterset, IA 50273
/25
$190,000 Sold May 14, 2025
- 921 Sq Ft
- $206/SF
- 147 Days On Market
- 2 Beds
- 1 Bath
- Built 1920
209 W Filmore St, Winterset, IA 50273

Just a few blocks from Historic Winterset square, welcome home to this 1920 home with lots of character. The property has been completely remodeled from top to bottom. Updates include limestone sidewalk and accents, siding and roof, oak wrapped front porch, vaulted ceilings, vinyl flooring, oak trim, woodwork and windows, cabinets, granite countertops, coffee bar, stainless steel farm sink,

Michael Fagerstrom Keller Williams Realty GDM

209 W Filmore St, Winterset, IA 50273

/24
Est $287,836 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
604 W Filmore St, Winterset, IA 50273

604 W Filmore St, Winterset, IA 50273

/12
$215,000
- Land
- 4.68 Acres
- $45,940 per Acre
2215 245 Ln, Winterset, IA 50273

Beautiful rolling building lot just south of town and on minimal gravel located on a dead end road! This 4.68 acre m/l lot is ready for you to bring your builder and build your dream home! The lot gently rolls to the north for a walk out opportunity and overlooks the neighbor's pristine pond! There will be very minimal covenants (currenty being drawn up by attorney) and the county needs to

Sarah Cowman Homefront Real Estate, LLC

2215 245 Ln, Winterset, IA 50273
/30
$181,000 Sold May 12, 2025
- 1,358 Sq Ft
- $133/SF
- 207 Days On Market
- 3 Beds
- 1 Bath
- Built 1905
712 N 2nd Ave, Winterset, IA 50273

Winterset west side 1 1/2 story home with many updates. New furnace & air, roof, windows, siding and more, all within the last few years. Home has large formal dining room open to living room. Kitchen has double closets on one side which make a nice pantry or additional storage. Three season room off the kitchen ready for you to update with some included materials. One main floor bedroom. The

Toni Tindle Covered Bridge Realty

712 N 2nd Ave, Winterset, IA 50273

/25
Est $209,137 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
809 E Benton St, Winterset, IA 50273

809 E Benton St, Winterset, IA 50273

/11
$170,000
- Land
- 6 Acres
- $28,239 per Acre
1804 Millstream Ct, Winterset, IA 50273

Wonderful opportunity to build on a 6 acre lot in Covered Bridge Estate. This lot provides private scenery with multiple places you could build your homesite. This lot has the potential for walking trails to the secluded lake or build with the lake in your back yard. North part of Winterset, 30 minutes to West Des Moines.

Lindsay Range EXIT Realty & Associates

1804 Millstream Ct, Winterset, IA 50273
/24
$145,000 Sold May 09, 2025
- 1,776 Sq Ft
- $82/SF
- 5 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1916
513 E Jefferson St, Winterset, IA 50273

Stately 2 story home is ready for a handy person to bring it to its full glory! This spacious home has original wood work, a large living room, dining room, kitchen and 1/2 bath on the main level. Upstairs are 4 good sized bedrooms and a full bath. There is a nice 2 car detached garage and large flat yard. Come see this spacious 2 story and make it your own! This property was a rental. Owners

Sarah Cowman Homefront Real Estate, LLC

513 E Jefferson St, Winterset, IA 50273

/16
Est $247,279 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
602 E Benton St, Winterset, IA 50273

602 E Benton St, Winterset, IA 50273

/27
$225,000
- Land
- 10 Acres
- $21,676 per Acre
TBD Carver Rd, Winterset, IA 50273

Picturesque 10 acre building site w many miles of valley views to build your dream home or multiple cabin retreat. Multiple building locations and driveways are possible on this property. Enjoy complete privacy, abundant natural beauty, and endless possibilities for creating your ideal retreat. Enjoy private the existing trails through the land just a few minutes south of Winterset and a half

Lindsay Range EXIT Realty & Associates

TBD Carver Rd, Winterset, IA 50273
/34
$185,000 Sold May 09, 2025
- 1,005 Sq Ft
- $184/SF
- 209 Days On Market
- 3 Beds
- 1 Bath
- Built 1880
304 E Washington St, Winterset, IA 50273

This one 1/2 story home is all new on the inside with many updates on the exterior. It features a newer metal roof and is well insulated. It is located on a corner lot with landscaping rocks and plants surrounding the appealing yard and tidy house. Garage has fresh paint and new board walls. Covered rear deck with fresh stain leads to basement. Interior includes all NEW appliances, sheet rock,

Toni Tindle Covered Bridge Realty

304 E Washington St, Winterset, IA 50273

/20
Est $252,462 Not Listed For Sale
- 4 Beds
- 2 Baths
- 924 Sq Ft
802 E Benton St, Winterset, IA 50273

802 E Benton St, Winterset, IA 50273

/4
$310,000
- Studio
- 1 Bath
- 995 Sq Ft
418 N 6th St, Winterset, IA 50273

Investor Alert! Super clean and well-maintained duplex investment property. Each unit has 2 bedrooms and 1 full bath. Large living room, spacious kitchen and dining area. Sliding door from the dining area leads to the backyard. The bedrooms have good size closets. 1st floor laundry. Ample storage space in the basement. 1 car attached garage. 418 N 6th St. - furnace new 2021, newer flooring and

Jennifer Stover Madison County Realty

418 N 6th St, Winterset, IA 50273
/35
$442,000 Sold May 09, 2025
- 2,000 Sq Ft
- $221/SF
- 317 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1979
1410 W Washington St, Winterset, IA 50273

Absolutely stunning totally remodeled home! You will not believe the space in this home until you get inside! The main level boasts 2000 square feet of beauty. Walk in and you will love the open airy feel of the large front living room with gorgeous gas fireplace. This room is open to the brand new kitchen with tons of cabinets and quartz countertops. The dining is large and has a coffee

Sarah Cowman Homefront Real Estate, LLC

1410 W Washington St, Winterset, IA 50273

/24
Est $263,740 Not Listed For Sale
- 2 Beds
- 1 Bath
- 840 Sq Ft
317 E North St, Winterset, IA 50273

317 E North St, Winterset, IA 50273

/17
$91,000
- 3 Beds
- 1 Bath
- 1,075 Sq Ft
315 N 4th Ave, Winterset, IA 50273

. 1.5-story home with a welcoming front porch and a 1-car detached garage. This home offers 3 bedrooms and 1 bath. Hardwood floors and carpet. 2 window units stay with the home. Large yard and great location!. Call today for your viewing!

Sarah Cowman Homefront Real Estate, LLC

315 N 4th Ave, Winterset, IA 50273
/20
$269,000 Sold May 02, 2025
- 1,483 Sq Ft
- $181/SF
- 24 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
316 S 7th Ave, Winterset, IA 50273

This beautiful 3 bedroom, 2 bath zero-entry residence built in 2021, boasts an open concept living area that creates a seamless flow throughout the home, making it perfect for entertaining and family gatherings. The spacious master bedroom with en suite off the living room, and at the separate end of the home from the two additional bedrooms, allows for a great private space. Laundry and mudroom

Kristin Flaherty Stoney Oak Properties LLC

316 S 7th Ave, Winterset, IA 50273

/20
Est $215,240 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,252 Sq Ft
506 E Filmore St, Winterset, IA 50273

506 E Filmore St, Winterset, IA 50273

/35
$285,000
- 3 Beds
- 2 Baths
- 1,913 Sq Ft
423 E Jefferson St, Winterset, IA 50273

Classic 1920 Craftsman with all of the charm and character you'd expect. As you walk up to the front porch you'll never want to leave! Perfect spot for your morning coffee or lounging at the end of a long day. As you enter, you'll immediately see the exposed wood beams in the family room that make it a cozy space. Newer gas fireplace is the focus of the family room, flanked by built in

Jennifer Stover Madison County Realty

423 E Jefferson St, Winterset, IA 50273
/35
$215,000 Sold May 02, 2025
- 1,254 Sq Ft
- $171/SF
- 201 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1958
815 W Court Ave, Winterset, IA 50273

Appealing brick ranch with two bedrooms & 1.5 bath on Winterset West side. This home has a very large living room with a brick fireplace as a focal point for this great space. Easy living on one level with a full basement including a second fireplace. There is a formal dining room with a closet which leads to a kitchen including all appliances. Kitchen has a generous amount of counter space and

Toni Tindle Covered Bridge Realty

815 W Court Ave, Winterset, IA 50273

/18
Est $227,164 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,248 Sq Ft
510 E Filmore St, Winterset, IA 50273

510 E Filmore St, Winterset, IA 50273

/18
$164,500
- 2 Beds
- 1 Bath
- 768 Sq Ft
408 E Benton St, Winterset, IA 50273

Charming & Updated in Winterset! This adorable home is move-in ready with tons of recent upgrades you'll love. Step into a brand-new kitchen and bathroom featuring modern finishes, complemented by stylish LVP flooring and fresh carpet throughout. The exterior shines with new siding and windows, offering both great curb appeal and energy efficiency. Sitting on a huge yard, there's plenty of space

Jamie Adkins RE/MAX Precision

408 E Benton St, Winterset, IA 50273
/29
$271,350 Sold May 02, 2025
- 2,106 Sq Ft
- $129/SF
- 293 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1976
1233 W Washington St, Winterset, IA 50273

If a large open living space is what you have been looking for, look no more. This easy living ranch home is very spacious with everything you need on the main level, including laundry! Inside the front door, you will love the front living room. Through the front living room, you will enter into the spacious kitchen with ample cabinet and countertop space with room for a dining table. Off the

Sarah Cowman Homefront Real Estate, LLC

1233 W Washington St, Winterset, IA 50273

/20
Est $188,008 Not Listed For Sale
- 2 Beds
- 1 Bath
- 986 Sq Ft
306 E Buchanan St, Winterset, IA 50273

306 E Buchanan St, Winterset, IA 50273

/9
$216,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
413 E Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

Alyssa Tadlock Madison County Realty

413 E Madison St, Winterset, IA 50273
/34
$745,000 Sold May 01, 2025
- Land
- 22 Acres
- $34,003 per Acre
- 150 Days On Market
1849 Fox Trail, Winterset, IA 50273

This is more than just a home! This is a picturesque rolling 20 acres with multiple streams, pond, and beautiful views. The tranquil setting has a 3 bed, 4 bath ranch home built in 2002 with over 3,000 sqft of finished living space. The home features hardwood and tile floors throughout the main level with multiple living spaces, dining room, large eat in white kitchen, laundry room and a

Timothy Schutte EXIT Realty & Associates

1849 Fox Trail, Winterset, IA 50273

/15
Est $221,662 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
423 E Benton St, Winterset, IA 50273

423 E Benton St, Winterset, IA 50273

/8
$220,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
411 W Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet in bedrooms and a

Alyssa Tadlock Madison County Realty

411 W Madison St, Winterset, IA 50273
/34
$310,180 Sold Apr 25, 2025
- Land
- 3.30 Acres
- $93,994 per Acre
- 9 Days On Market
2197 175th Ct, Winterset, IA 50273

Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all

Alison Frank Platinum Realty LLC

2197 175th Ct, Winterset, IA 50273

/19
Est $193,805 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
715 N 5th St, Winterset, IA 50273

715 N 5th St, Winterset, IA 50273

/19
$224,500
- 3 Beds
- 1 Bath
- 1,118 Sq Ft
223 N 8th St, Winterset, IA 50273

Amazing home renovation! Sweet ranch home on a large corner lot. 3 bedroom, 1 bath, 1118sf. The all new kitchen is efficient with a breakfast bar all new cabinetry/countertops and newer stainless steel appliances. Enjoy your morning coffee in the sunny dining area right off the kitchen. The spacious breezeway is the perfect spot for 1st floor laundry and plenty of extra room for coats/shoes. Next

Jennifer Stover Madison County Realty

223 N 8th St, Winterset, IA 50273
/17
$149,000 Sold Apr 18, 2025
- 772 Sq Ft
- $193/SF
- 3 Days On Market
- 2 Beds
- 1 Bath
- Built 1910
622 N 7th St, Winterset, IA 50273

Welcome to this charming 2-bedroom, 1-bath ranch-style home situated on a corner lot in the heart of Madison County. This cozy property offers a spacious living and kitchen area, perfect for relaxing or entertaining. Enjoy the convenience of a 2-car attached garage and a large, fenced-in yard. While it needs a little TLC (mostly cosmetic), this home offers great potential. Experience the

Nicholas Scar Iowa Realty Mills Crossing

622 N 7th St, Winterset, IA 50273

/25
Est $264,333 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
508 E Lane St, Winterset, IA 50273

508 E Lane St, Winterset, IA 50273

/33
$549,900
- 6 Beds
- 4 Baths
- 3,155 Sq Ft
2237 Holliwell Valley Ct, Winterset, IA 50273

Remarks: Welcome home! This 4.3 acre homestead will allow you to enjoy life to the fullest. Step into a spacious home with over 4,700 sq ft total of finished living space. At the heart of the home is a gorgeous kitchen with soft-close drawers, a walk-in pantry, and breathtaking views of the countryside hills and peaceful neighboring pond—best enjoyed from the sunny dining area or

Wendy Eilander RE/MAX Concepts

2237 Holliwell Valley Ct, Winterset, IA 50273
/19
$169,500 Sold Apr 16, 2025
- 1,216 Sq Ft
- $139/SF
- 109 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1921
706 N 1st Ave, Winterset, IA 50273

This picturesque Craftsman-style home offers 1920s charm. With 3 bedrooms, one that can be used as an office space and 1 1/2 baths, it features a spacious layout with high ceilings that enhance the feeling of openness. This home has retained much of its original woodwork, giving it a warm, inviting atmosphere. Recent upgrades include a new roof, replaced by previous owners, in the fall of 2022

Eric Vetsch Keller Williams Realty GDM

706 N 1st Ave, Winterset, IA 50273

/26
Est $251,971 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
622 W Fremont St, Winterset, IA 50273

622 W Fremont St, Winterset, IA 50273

/35
$450,000
- 5 Beds
- 4 Baths
- 3,520 Sq Ft
204 W Washington St, Winterset, IA 50273

If you're looking for ** WOW ** this. is. IT!! This stunning 1875 two story has been well cared for and offers a long list of modern amenities. Situated just a couple blocks from the historic Winterset square and close to schools, restaurants and retail on a large corner lot with outdoor living and perennials waiting for you. Relax on the wrap around porch or entertain on the back patio

Alyssa Tadlock Madison County Realty

204 W Washington St, Winterset, IA 50273

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