Madison, IA Homes

/32
$160,000 Sold Jul 08, 2025
- 2,018 Sq Ft
- $79/SF
- 41 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1922
415 E Jefferson St, Winterset, IA 50273

Are you looking for a large 4 bed/1.5 bath home with plenty of character, in the beautiful town of Winterset? Then this is the house for you. From the beautiful oak hardwood floors to the built-in corner cabinet in the dining area, and all of the smaller windows that bring in plenty of natural light, you will want to call this house HOME. The roomy kitchen has new stainless-steel appliances and

Betsy Breeding Realty ONE Group Impact

415 E Jefferson St, Winterset, IA 50273

/22
Est $211,818 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,213 Sq Ft
722 N 6th Avenue Cir, Winterset, IA 50273

722 N 6th Avenue Cir, Winterset, IA 50273

/28
$550,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
715 N John Wayne Dr, Winterset, IA 50273

Super unique investment opportunity! This property consists of a residential house and 4 rental units. The house is 1728 sf with 3 bedrooms, 2 bathrooms, 2 family rooms, 1st floor laundry, basement, 2 car garage. The lower level of the house also has 1 bedroom, bath, kitchen, fireplace. You could also rent out the LL of the house. Making total number of units available for rent: 6. The owners

Jennifer Stover Madison County Realty

715 N John Wayne Dr, Winterset, IA 50273
/22
$525,000 Sold Jul 08, 2025
- 1,911 Sq Ft
- $275/SF
- 98 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
1785 Millstream Ct, Winterset, IA 50273

Custom built and absolutely stunning, this three-bedroom, ranch home sitting on 3 acres with paved roads is in A+ condition! Walls of floor to ceiling windows flood the home with natural light and provide amazing sunset views of the valley. 2x6 quality construction, with clean, modern lines. Finishes are high end and the floor plan and space is perfect for right sizing, or a family. Radiant floor

JoAnn Manning Iowa Realty Mills Crossing

1785 Millstream Ct, Winterset, IA 50273

/36
Est $768,660 Not Listed For Sale
- 4 Beds
- 3.5 Baths
2208 204th Ct, Winterset, IA 50273

2208 204th Ct, Winterset, IA 50273

/34
$350,000
- 5 Beds
- 2.5 Baths
- 2,968 Sq Ft
323 W Jefferson St, Winterset, IA 50273

Exquisite historic home in the heart of Winterset just blocks from the bustling downtown square. If you love a quality historic home, this one is for you! This Freestyle Queen Anne Victorian 2-story is sure to impress. The past 2 owners have taken exquisite care of this gem. You will love the original woodwork hard floors, leaded glass & character! A front porch greets you as you enter complete

Sarah Cowman Homefront Real Estate, LLC

323 W Jefferson St, Winterset, IA 50273
/21
$139,900 Sold Jun 30, 2025
- 672 Sq Ft
- $208/SF
- 5 Days On Market
- 2 Beds
- 1 Bath
- Built 1947
215 S 2nd St, Winterset, IA 50273

Welcome to historic Winterset! This updated 2-bed, 1-bath home is move-in ready with a new furnace and AC (2020), updated roof, fresh paint, and new flooring. The spacious backyard features a courtyard with pergola, new shed, and full privacy fence—perfect for relaxing or entertaining.Ideal for first-time buyers, downsizers, or as a short-term rental. Includes an HSA home warranty for

Nicholas Scar Iowa Realty Mills Crossing

215 S 2nd St, Winterset, IA 50273

/16
Est $215,249 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,016 Sq Ft
1510 W Jefferson St, Winterset, IA 50273

1510 W Jefferson St, Winterset, IA 50273

/35
$345,900
- 3 Beds
- 2.5 Baths
- 2,436 Sq Ft
724 W Jefferson St, Winterset, IA 50273

Prepare to be impressed with the renovations done to bring this stately home back to it's orignal glory! Step up to the inviting front covered porch & through the original leaded glass door into the stunning entryway showcasing the gorgeous stairway & original woodwork. The orignal hardwood floors flow throughout the entry room, HUGE living room, and into the formal dining room. Off the living

Sarah Cowman Homefront Real Estate, LLC

724 W Jefferson St, Winterset, IA 50273
/9
$22,000 Sold Jun 30, 2025
- 1,031 Sq Ft
- $21/SF
- 19 Days On Market
- 2 Beds
- 1 Bath
- Built 2025
415 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

415 E Madison St, Winterset, IA 50273

/33
Est $321,163 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,060 Sq Ft
215 N 15th Ave, Winterset, IA 50273

215 N 15th Ave, Winterset, IA 50273

/34
$299,000
- 3 Beds
- 2 Baths
- 1,741 Sq Ft
620 W Filmore St, Winterset, IA 50273

Charming Ranch with Modern Updates on a Quiet StreetWelcome to this beautifully updated home nestled on a peaceful street, perfect for those seeking both comfort and convenience. Step onto the quaint front porch and into a home that blends cozy charm with modern finishes throughout.This spacious home features a large primary bedroom with an attached bathroom, plus two additional

Alyssa Tadlock Madison County Realty

620 W Filmore St, Winterset, IA 50273
/31
$310,000 Sold Jun 30, 2025
- 1,415 Sq Ft
- $219/SF
- 54 Days On Market
- 5 Beds
- 2.5 Baths
- Built 2002
221 N 15th Ave, Winterset, IA 50273

Welcome to your future home in the heart of Winterset! This beautiful 1.5-story home offers 1,415 sq ft of living space, featuring 5 bedrooms, 2.5 bathrooms, an attached 2-car garage, and a fully fenced backyard with a spacious deck—ideal for enjoying the outdoors.The main level includes the master bedroom and first-floor laundry for your everyday convenience.Just minutes away

Danielle Burnight RE/MAX Revolution

221 N 15th Ave, Winterset, IA 50273

/25
Est $348,951 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,172 Sq Ft
307 N 14th Ave, Winterset, IA 50273

307 N 14th Ave, Winterset, IA 50273

/22
$440,000
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
2369 Saint Charles Rd, Winterset, IA 50273

MADISON COUNTY ACREAGE! Beautiful ZERO ENTRY home, that was built with CONCRETE WALLS, on 10+- wooded acres. The beauty of the country, but on a paved road, close to Winterset and a 30-minute commute to West Des Moines. This home has a large kitchen with HICKORY CABINETS and plenty of counter space. You will love all of the big windows and French doors, bringing in so much natural light. The OPEN

Betsy Breeding Realty ONE Group Impact

2369 Saint Charles Rd, Winterset, IA 50273
/26
$337,000 Sold Jun 27, 2025
- 2,267 Sq Ft
- $149/SF
- 1 Day On Market
- 3 Beds
- 2.5 Baths
- Built 1972
925 W Jefferson St, Winterset, IA 50273

One of the homes with the best curb appeal in town has just hit the market! This spacious 1.5-story Cape Cod-style home is clean, tidy, and ready for a new owner. Walk up to the inviting front porch and enter the foyer. The spacious living room, featuring a picture window, will greet you as you enter. The formal dining room is off the living room & adjacent to the spacious kitchen with lots of

Sarah Cowman Homefront Real Estate, LLC

925 W Jefferson St, Winterset, IA 50273

/24
Est $327,961 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,415 Sq Ft
225 N 14th Ave, Winterset, IA 50273

225 N 14th Ave, Winterset, IA 50273

/32
$499,900
- 6 Beds
- 3.5 Baths
- 2,351 Sq Ft
301 Magnolia Point, Winterset, IA 50273

Spacious and beautifully maintained 6-bedroom, 3.5-bath home situated on a generous 0.65-acre lot! Built in 2020, this home offers the perfect blend of modern style and functional living. The open-concept main level features a bright kitchen with ample storage and a cozy living area. The walk-out basement provides even more living space—ideal for entertaining, a home gym, or rec area. Enjoy the

Rachel Eller Summerset Realty

301 Magnolia Point, Winterset, IA 50273
/29
$215,000 Sold Jun 26, 2025
- 1,673 Sq Ft
- $129/SF
- 27 Days On Market
- 2 Beds
- 1 Bath
- Built 1944
315 W Washington St, Winterset, IA 50273

Welcome to your dream home in the heart of Winterset! This charming and spacious brick ranch offers everything you need for comfortable, convenient living. As soon as you step inside, you will be greeted by beautiful hardwood floors that flow throughout the main level. No more carrying laundry up and down stairs - this home features a main level laundry with the option to easily move it

Misty Darling BH&G Real Estate Innovations

315 W Washington St, Winterset, IA 50273

/17
Est $289,767 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,008 Sq Ft
802 N 4th Ave, Winterset, IA 50273

802 N 4th Ave, Winterset, IA 50273

/34
$585,000
- 5 Beds
- 3 Baths
- 1,739 Sq Ft
711 E Madison St, Winterset, IA 50273

Spectular 5 bedroom ranch beautiful finish and an enormous 30x54 shop/garage with concrete floor on 1.75 acres! This home boasts a huge living room which features high ceilings and a beautiful fireplace while the formal dining room offers a bit of privacy, both with attractive hardwood floors. The kitchen has tons of storage and leads to an eating area. Off the dining area is an enormous deck

Sarah Cowman Homefront Real Estate, LLC

711 E Madison St, Winterset, IA 50273
/35
$348,000 Sold Jun 20, 2025
- 1,411 Sq Ft
- $247/SF
- 12 Days On Market
- 5 Beds
- 3 Baths
- Built 2002
1303 N 7th St, Winterset, IA 50273

Welcome to this beautifully maintained 5-bedroom, 3-bath walk-out ranch nestled on a spacious 1-acre corner lot in town! This home offers the perfect blend of comfort, convenience, and charm. Step inside to find a functional and inviting layout, with a new furnace, A/C, water heater, newer roof and newer appliances providing peace of mind for years to come. The walk-out basement adds great living

Rachel Eller Summerset Realty

1303 N 7th St, Winterset, IA 50273

/12
Est $229,462 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,169 Sq Ft
1002 N 4th Ave, Winterset, IA 50273

1002 N 4th Ave, Winterset, IA 50273

/33
$348,000
- 4 Beds
- 2.5 Baths
- 2,026 Sq Ft
708 W Fremont St, Winterset, IA 50273

Tons of room to spread out in this 4 bed 3 bath home. Walk into the gathering room that has many uses. It could be a formal dining room or a great sitting area. The spacious kitchen has plenty of cabinets and counter tops space and all appliances are included. The dining area can accommodate a large table. There is a huge mudroom off the kitchen as well as a 3/4 bath. The living room is huge

Sarah Cowman Homefront Real Estate, LLC

708 W Fremont St, Winterset, IA 50273
/17
$235,000 Sold Jun 20, 2025
- Land
- 35 Acres
- $6,714 per Acre
- 333 Days On Market
2430 Highway 169, Winterset, IA 50273

This land had been used as a motocross track "Riverside Raceway", and is now being offered as land only. This property includes two parcels, the larger parcel runs along the Middle River south of Winterset and is IDEAL for hunting and recreation, and the smaller adjacent parcel is suitable for building and is NOT in a flood plain. The property is just a couple miles South from the town of

Keith Soldwisch Zealty Home Advisors

2430 Highway 169, Winterset, IA 50273

/22
Est $243,522 Not Listed For Sale
- 4 Beds
- 1 Bath
- 1,032 Sq Ft
501 W Benton St, Winterset, IA 50273

501 W Benton St, Winterset, IA 50273

/28
$325,000 Pending
- 3 Beds
- 2 Baths
- 1,414 Sq Ft
1427 W Washington St, Winterset, IA 50273

Charming 3-Bed, 2-Bath Ranch on Peaceful, Established Street.Welcome home to this beautifully maintained 3-bedroom, 2-bath ranch nestled on a quiet, tree-lined street in a well-established neighborhood. This move-in ready gem offers the perfect blend of comfort and functionality, featuring newer heating and air systems to keep you cozy year-round.Step inside to find a spacious layout with

Alyssa Tadlock Madison County Realty

1427 W Washington St, Winterset, IA 50273
/21
$515,000 Sold Jun 18, 2025
- 1,590 Sq Ft
- $324/SF
- 19 Days On Market
- 4 Beds
- 3 Baths
- Built 2025
902 S 9th Ave, Winterset, IA 50273

New construction ranch with a finished walk-out lower level. 4 bedroom, 3 bath, over 2800sf finished. Kitchen features a coffee bar, breakfast bar, walk-in pantry. Great open concept floor plan. The lower level features a large family room and 2 bedrooms with oversized closets. Covered front porch and back deck. Located in a small, quiet residential neighborhood.

Jennifer Stover Madison County Realty

902 S 9th Ave, Winterset, IA 50273

/34
Est $284,143 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 1,372 Sq Ft
201 S 14th Ave, Winterset, IA 50273

201 S 14th Ave, Winterset, IA 50273

/19
$298,000 Pending
- 4 Beds
- 2.5 Baths
- 2,696 Sq Ft
103 W Lane St, Winterset, IA 50273

Spacious 4-Bedroom Home on a Corner Lot!Welcome to this beautifully maintained 4-bedroom, 3-bath home offering 2,696 sq ft of versatile living space. Situated on a desirable corner lot, this property features a formal dining room, two spacious family rooms, and hardwood floors throughout.Upstairs, the oversized primary suite offers a flexible bonus area with a large closet. All three

Amanda Poganski Boutique Real Estate

103 W Lane St, Winterset, IA 50273
/30
$246,600 Sold Jun 16, 2025
- 1,474 Sq Ft
- $167/SF
- 49 Days On Market
- 3 Beds
- 2 Baths
- Built 1887
416 N 1st Ave, Winterset, IA 50273

Charming 3-bedroom Home with Spacious Heated Shop!This well-maintained 3-bedroom 2-bath home offers comfortable living with an added bonus- a 30x32 spray foam insulated and heated shop perfect for hobbies, storage, or a workspace! Inside you'll find a welcoming layout with a bright living area, a functional kitchen, and plenty of natural light. Outside, enjoy a spacious yard with room to relax or

Rachel Eller Summerset Realty

416 N 1st Ave, Winterset, IA 50273

/33
Est $184,406 Not Listed For Sale
- 3 Beds
- 1 Bath
- 876 Sq Ft
205 S 16th Ave, Winterset, IA 50273

205 S 16th Ave, Winterset, IA 50273

/35
$310,000 Pending
- 3 Beds
- 1.5 Baths
- 1,792 Sq Ft
522 N 7th Ave, Winterset, IA 50273

If you love gorgeous woodwork, you must see this stunning 2-story home! The first thing you will notice is the large inviting front porch - the perfect spot for relaxing! Inside, you will notice the immaculate woodwork in the living and dining rooms. The dining room features built-ins and boasts a beautiful staircase. The kitchen is very large, with plenty of cabinet and countertop space, as well

Sarah Cowman Homefront Real Estate, LLC

522 N 7th Ave, Winterset, IA 50273
/31
$395,000 Sold Jun 16, 2025
- 1,518 Sq Ft
- $260/SF
- 67 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1996
2923 N John Wayne Dr, Winterset, IA 50273

Here is your chance to live on 3 acres right off of Hwy 169 in Madison County. Check out this updated ranch home featuring 4 bedrooms 3 baths. On the main level you have the Primary suite, with tons of closet space, 2nd bedroom or office. spacious living area with large picture windows, and a large deck off the dining room. On the finished lower level there are 2 additional bedrooms, 2nd family

Rachel Eller Summerset Realty

2923 N John Wayne Dr, Winterset, IA 50273

/29
Est $473,126 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,484 Sq Ft
1515 W Washington St, Winterset, IA 50273

1515 W Washington St, Winterset, IA 50273

/11
$655,384
- Land
- 96 Acres
- $6,819 per Acre
00 Millstream Ave, Winterset, IA 50273

Premium Row Crop Ground with Endless Potential | Madison County, IowaRepresenting the Utsler Family Trust in the sale of 50.51 gross acres m/l located in Section 18 of Scott Township in Madison County. This farm consists of an estimated 48.19 FSA cropland acres currently in row crop production boasting highly productive soils including Sharpsburg, Macksburg, and Clearfield silty clay

Andrew Zellmer Peoples Company

00 Millstream Ave, Winterset, IA 50273
/25
$213,865 Sold Jun 13, 2025
- 1,061 Sq Ft
- $202/SF
- 13 Days On Market
- 3 Beds
- 1 Bath
- Built 1910
707 E Buchanan St, Winterset, IA 50273

Fully remodeled 3 bedroom 1 bathroom 2 stall garage home in Winterset! Spacious living room with windows all around offering so much natural light! New kitchen!! New cabinets, new countertops, and new appliances in this kitchen offering plenty of cabinet and countertop space! All new appliances also included in this home! One bedroom on the main level, along with the full bathroom with laundry

Jenn Ho Goh GoSynergy Realty

707 E Buchanan St, Winterset, IA 50273

/23
Est $253,424 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,270 Sq Ft
1413 W Washington St, Winterset, IA 50273

1413 W Washington St, Winterset, IA 50273

/14
$1,150,000
- Land
- 96 Acres
- $11,965 per Acre
00 Clark Tower Rd, Winterset, IA 50273

Prime Rural Residential Developmental Land Offering | Just south of Winterset, IowaRepresenting the Utsler Family Trust in the sale of an exceptional 96.11-acre m/l property located just 3 miles south of Winterset, Iowa, with paved access from Clark Tower Road. This offering represents a rare opportunity to acquire a tract of land already zoned Rural Residential—an increasingly difficult

Andrew Zellmer Peoples Company

00 Clark Tower Rd, Winterset, IA 50273
/21
$225,000 Sold Jun 11, 2025
- 960 Sq Ft
- $234/SF
- 107 Days On Market
- 3 Beds
- 1 Bath
- Built 1976
703 N 3rd Ave, Winterset, IA 50273

You will want to check out this well kept 3 bedroom home with finished basement on a corner lot. Home features 3 bedrooms and one bath on the main level. The kitchen is bright and nicely updated with newer appliances which are included! The dining area is adjacent to the kitchen which has a door that leads to the huge deck - perfect for grilling! The living room is very large with a big bright

Sarah Cowman Homefront Real Estate, LLC

703 N 3rd Ave, Winterset, IA 50273

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