Madison, IA Homes

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  /6

  $275,000

  • Land
  • 10 Acres
  • $26,882 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Don't miss this rare opportunity to own 10 acres m/l of picturesque countryside just 8 miles west of Winterset, situated on a hard surface road and a prime corner lot. This walkout lot is ready for your dream home with rural water, electricity, and a driveway already added, saving you the time and expense of major improvements. The gently rolling terrain offers stunning views and the perfect

  

  Chris Kew

  RE/MAX Precision

  (515) 531-5829

  2212 Deer Run Ave, Winterset, IA 50273
• 

  Explore Winterset

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  /9

  $1,300 per month

  • 2 Beds
  • 2.5 Baths
  • 1,213 Sq Ft
  • Apartment for Rent

  721 N 6th Avenue Cir, Winterset, IA 50273

  Well maintained townhome located at the end of a quiet Culdesac. This 2 bedroom 2 bath is available to rent month to month up to 6 months. Lawn care and snow are included in rent. One month rent deposit due prior to possession. Tenant will be responsible for utilities. All information obtained from seller and public records.

  

  David Welch

  RE/MAX Precision

  (515) 800-9723

  721 N 6th Avenue Cir, Winterset, IA 50273
• 

  

  

  /25

  $185,000 Sold Aug 25, 2025

  • 1,030 Sq Ft
  • $180/SF
  • 83 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2021

  507 W Madison St, Winterset, IA 50273

  EZ living on one level! This 2 bedroom, 1 bath triplex has center location which is very quiet and economical.Kitchen has an open floor plan to living area boasting vaulted ceilings. Handy pantry closet located in kitchen.Features include: 36-inch doorways throughout, easy access to tiled walk-in shower, master bedroom has large walk-in closet with access from bathroom and bedroom, trey

  Toni Tindle Covered Bridge Realty

  507 W Madison St, Winterset, IA 50273
• 

  

  

  /10

  Not Listed For Sale

  Lot 9 Scenic Ridge St, Winterset, IA 50273

  Lot 9 Scenic Ridge St, Winterset, IA 50273
• 

  

  

  /35

  $313,500

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  1220 W Court Ave, Winterset, IA 50273

  Instantly appealing 1 1/2 story family home on Winterset W side with attached 2 car garage. There is a large level 70x157 lot w/a fenced backyard & shed. Front entrance leads to a cheerful living room with wide staircase to the upper floor. The bright southern facing kitchen has newer appliances & a pantry. The kitchen is open to a formal dining room with hardwood floors & gas fireplace as a

  

  Toni Tindle

  Covered Bridge Realty

  (515) 498-5106

  1220 W Court Ave, Winterset, IA 50273
• 

  

  /18

  $800 - $995 per month

  The Bridges

  1 - 2 Beds

  1111 N 8th Ave, Winterset, IA 50273

  Formerly Known as Candle Ridge, The Bridges, an Apartment Community, offers affordable 1 and 2 bedroom apartments. Apartments are being freshened up with brand-new LVP flooring, updated cabinetry, and counters. Age restrictions no longer apply!

  1111 N 8th Ave, Winterset, IA 50273
• 

  

  /34

  $495,000 Sold Aug 22, 2025

  • 1,728 Sq Ft
  • $286/SF
  • 67 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  2381 Carver Rd, Winterset, IA 50273

  Escape to nature with this serene sqft ranch-style home set on 10+ acres of private land with miles of hiking trails and breathtaking views. Perfect for outdoor lovers seeking tranquility without sacrificing comfort. This 3 bed 2 bath home was built out of ICF (Insulated Concrete Forms) which makes it very efficient and able to withstand severe storms. The R-value/U-value of ICF in combination

  Lindsay Range EXIT Realty & Associates

  2381 Carver Rd, Winterset, IA 50273
• 

  

  /21

  Est $166,175 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,324 Sq Ft

  520 N 3rd Ave, Winterset, IA 50273

  520 N 3rd Ave, Winterset, IA 50273
• 

  

  /33

  $239,900 Pending

  • 3 Beds
  • 1 Bath
  • 942 Sq Ft

  1755 280th St, Winterset, IA 50273

  Three-bedroom 1 bath acreage home on 2.5 acres more or less. Home has had complete remodel with new sheetrock and insulation. Newer roof and AC with new duct work. Newer laminate flooring throughout within last two years. Replaced all fixtures cabinets sinks and more. Added extras include all appliances. 16x20 detached garage with 8 ft by 16 ft lean-to in rear. Included animal pens outside the

  

  Toni Tindle

  Covered Bridge Realty

  (515) 690-7594

  1755 280th St, Winterset, IA 50273
• 

  

  /25

  $157,800 Sold Aug 20, 2025

  • 1,336 Sq Ft
  • $118/SF
  • 59 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1870

  702 N 2nd Ave, Winterset, IA 50273

  Step inside this spacious 1.5-story and discover a home designed for comfort, convenience, and memorable gatherings. The living and dining areas provide the perfect setting for entertaining friends and family. The cheerful kitchen with plenty of space for a breakfast table or island. A convenient half bath is located on the main level. There is a large bonus room off the living room with french

  Sarah Cowman Homefront Real Estate, LLC

  702 N 2nd Ave, Winterset, IA 50273
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  /12

  Est $230,161 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,184 Sq Ft

  816 E South St, Winterset, IA 50273

  816 E South St, Winterset, IA 50273
• 

  

  /28

  $274,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  609 E Filmore St, Winterset, IA 50273

  Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright south facing over the sink window, included

  

  Toni Tindle

  Covered Bridge Realty

  (515) 495-5285

  609 E Filmore St, Winterset, IA 50273
• 

  

  /35

  $749,900 Sold Aug 15, 2025

  • 1,742 Sq Ft
  • $430/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2016

  4726 Cherrywood Ln, Winterset, IA 50273

  Welcome home to your in-town acreage situated north of Winterset, right on Cumming Road. No gravel to worry about here! This four-bedroom, three-bath walkout ranch home has undergone many extensive updates in the kitchen & dining area. This home was made for entertaining with a gorgeous kitchen with a huge center island, perfect for large gatherings. The dining room off the kitchen has extra

  Sarah Cowman Homefront Real Estate, LLC

  4726 Cherrywood Ln, Winterset, IA 50273
• 

  

  /26

  Est $389,977 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2647 Bittersweet Ave, Winterset, IA 50273

  2647 Bittersweet Ave, Winterset, IA 50273
• 

  

  /30

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,389 Sq Ft

  1913 N 1st St, Winterset, IA 50273

  Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting on nearly an acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master BR on 1st floor has large walk-in closet, and tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal

  

  Toni Tindle

  Covered Bridge Realty

  (515) 824-5239

  1913 N 1st St, Winterset, IA 50273
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  /28

  $325,000 Sold Aug 15, 2025

  • 1,414 Sq Ft
  • $230/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  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
• 

  

  /35

  Est $531,712 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2395 148th St, Winterset, IA 50273

  2395 148th St, Winterset, IA 50273
• 

  

  /11

  $655,384

  • Land
  • 51 Acres
  • $12,975 per Acre

  0 Millstream Ct Unit 24336276, Winterset, IA 50273

  Premium Row Crop Ground with Endless Potential | Madison County, IowaPeoples Company is proud to represent 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

  Andrew Zellmer

  0 Millstream Ct Unit 24336276, Winterset, IA 50273
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  /18

  $226,000 Sold Aug 12, 2025

  • 1,480 Sq Ft
  • $153/SF
  • 94 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1890

  715 W North St, Winterset, IA 50273

  Check out this adorable home makeover! 2 bedroom, 2 bath, 1480sf, 1st floor laundry. Great kitchen with ample counter space and a large dining area. Just off the kitchen is the 1st floor laundry and a large bonus space. This space would be perfect for a home office or extra space for kids. It also has access to the backyard. The primary bedroom has the 3/4 bath and access to the back deck.

  Jennifer Stover Madison County Realty

  715 W North St, Winterset, IA 50273
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  /33

  Est $387,025 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  906 N 14th Ave, Winterset, IA 50273

  906 N 14th Ave, Winterset, IA 50273
• 

  

  /15

  $1,150,000

  • Land
  • 96 Acres
  • $11,965 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Prime Rural Residential Developmental Land Offering | Just south of Winterset, IowaPeoples Company is proud to represent 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 Residentialan

  Andrew Zellmer

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /31

  $226,000 Sold Aug 08, 2025

  • 1,584 Sq Ft
  • $143/SF
  • 43 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  318 W Green St, Winterset, IA 50273

  Appealing 1.5 story 3 - bedroom home on Winterset West side close to historic square. Welcoming covered front porch makes a perfect place to enjoy spending more time outdoors. Interior includes one BR on the main floor with corner closet allowing additional storage. This room would also make a great office space. Updated kitchen with bright south facing custom window, newer appliances and

  Toni Tindle Covered Bridge Realty

  318 W Green St, Winterset, IA 50273
• 

  

  /23

  Est $359,437 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,273 Sq Ft

  807 N 15th Ave, Winterset, IA 50273

  807 N 15th Ave, Winterset, IA 50273
• 

  

  /132

  $2,931,000

  • Land
  • 400 Acres
  • $7,328 per Acre

  2169 Adair Madison Ave, Winterset, IA 50273

  Welcome to a truly exceptional and one-of-a-kind property offering the very best of Iowa’s scenic countryside. Situated just a few miles west of Winterset, this breathtaking 400 +/- acre farm presents a rare opportunity to own a perfect blend of income-producing land and world-class hunting.This property features approximately120 +/- acres of tiled and terraced cropland, currently under

  Sean Stewart Midwest Land Group

  2169 Adair Madison Ave, Winterset, IA 50273
• 

  

  /35

  $310,000 Sold Aug 07, 2025

  • 1,792 Sq Ft
  • $173/SF
  • 10 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1915

  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
• 

  

  /35

  Est $404,194 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 1,504 Sq Ft

  905 N 15th Ave, Winterset, IA 50273

  905 N 15th Ave, Winterset, IA 50273
• 

  

  /26

  $415,000

  • 4 Beds
  • 3.5 Baths
  • 1,710 Sq Ft

  1011 N 14th Ave, Winterset, IA 50273

  Discover your own slice of heaven right in town! This inviting two-story home is set in a friendly neighborhood where there's plenty of room to play and grow. The thoughtful layout makes the most of every square foot, creating spaces that work well for everyday life.The main level welcomes you with a handy drop zone, half bath, and a office with French doors. The open kitchen and family room

  Michelle Hanson RE/MAX Concepts

  1011 N 14th Ave, Winterset, IA 50273
• 

  

  /18

  $297,500 Sold Aug 05, 2025

  • 995 Sq Ft
  • $299/SF
  • 41 Days On Market

  • Studio
  • 2 Baths
  • Built 1994

  515 E North 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. 515 E. North has a newer stove and water heater. 519

  Jennifer Stover Madison County Realty

  515 E North St, Winterset, IA 50273
• 

  

  /29

  Est $417,519 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,145 Sq Ft

  818 N 9th Ave, Winterset, IA 50273

  818 N 9th Ave, Winterset, IA 50273
• 

  

  /20

  $309,900

  • 3 Beds
  • 1.5 Baths
  • 2,130 Sq Ft

  721 W Court Ave, Winterset, IA 50273

  Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

  Larry Corkrean Madison County Realty

  721 W Court Ave, Winterset, IA 50273
• 

  

  /31

  $477,500 Sold Aug 01, 2025

  • 1,597 Sq Ft
  • $299/SF
  • 23 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2023

  519 W Mills St, Winterset, IA 50273

  Better Than New – Modern Elegance in a Serene Setting. Step into modern luxury with this stunning 4-bedroom, 3-bathroom home nestled in an established neighborhood and backing to mature trees for added privacy. From the moment you approach the front entrance, you'll be captivated by its sleek, contemporary design and inviting curb appeal. The main level features a spacious open-concept layout

  Renee Dunkel Century 21 Signature

  519 W Mills St, Winterset, IA 50273
• 

  

  /35

  Est $526,054 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  909 N 9th Ave, Winterset, IA 50273

  909 N 9th Ave, Winterset, IA 50273
• 

  

  /35

  $335,000

  • 4 Beds
  • 2 Baths
  • 1,912 Sq Ft

  59 E Benton St, Winterset, IA 50273

  Step inside this well-loved home that blends timeless character with modern updates—ready for its next owner to make it their own. The home’s original woodwork, in excellent condition, adds warmth and charm throughout. Enjoy relaxing mornings with coffee or peaceful evenings with dinner on the inviting front porch. Inside, you’ll find a spacious living room that flows seamlessly into a formal

  Sarah Cowman Homefront Real Estate, LLC

  59 E Benton St, Winterset, IA 50273
• 

  

  /26

  $289,500 Sold Aug 01, 2025

  • 1,344 Sq Ft
  • $215/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2008

  902 W Filmore St, Winterset, IA 50273

  WELCOME TO WINTERSET! Beautiful, well maintained, townhome has a nice open floor plan with plenty of natural light. The large living room, with gas fireplace, opens up to the dining area and kitchen, great for entertaining. The nice sized kitchen, with plenty of cabinets and a pantry, has beautiful new quartz countertops. All the flooring is new as well, including the water resistant/scratch

  Betsy Breeding Realty ONE Group Impact

  902 W Filmore St, Winterset, IA 50273
• 

  

  /17

  Est $294,439 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  809 W Mills St, Winterset, IA 50273

  809 W Mills St, Winterset, IA 50273
• 

  

  /35

  $649,500

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  2283 Clark Tower Rd, Winterset, IA 50273

  Discover this stunning newly built ICF (Insulated Concrete Form) berm home, showcasing executive-level finishes and exceptional energy efficiency. Nestled on just over 4 picturesque acres with scenic views of the iconic Clark Tower and Middle River Valley, this property offers both privacy and convenience. Ideally located on pavement for easy access. Enjoy ample space with several versatile

  Marcus Sereg Iowa Realty South

  2283 Clark Tower Rd, Winterset, IA 50273
• 

  

  /35

  $1,150,000 Sold Aug 01, 2025

  • 2,244 Sq Ft
  • $512/SF
  • 47 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2016

  1720 Merriam Ct, Winterset, IA 50273

  Spectacular acreage near Winterset with gorgeous 4+Bedroom/4 Bath home on 21+acres, including hunt-able private timber ground. It’s the details that make this property so special. Enjoy numerous outdoor spaces: covered deck with view of 2 ponds (1 is stocked), a covered patio, outdoor fireplace on fabulous open patio, large Pole Barn for all your hobbies, toys and tools and a 3+car tandem

  Nancy Shrader Keller Williams Ankeny Metro

  1720 Merriam Ct, Winterset, IA 50273
• 

  

  /25

  Est $210,475 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,213 Sq Ft

  821 W Fremont St, Winterset, IA 50273

  821 W Fremont St, Winterset, IA 50273
• 

  

  /35

  $485,000

  • 5 Beds
  • 3 Baths
  • 2,137 Sq Ft

  812 N 8th Ave, Winterset, IA 50273

  Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort and style. You will love the stunning stone fireplace as the focal point in the living room with vaulted-ceilings, creating a warm and welcoming atmosphere. The kitchen is nice with granite countertops and plenty of cabinets. The primary bedroom is complete with an ensuite featuring a tile shower with dual

  Matt Cole RE/MAX Concepts

  812 N 8th Ave, Winterset, IA 50273
• 

  

  /23

  $200,000 Sold Aug 01, 2025

  • 1,008 Sq Ft
  • $198/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1956

  324 W Filmore St, Winterset, IA 50273

  Adorable 2 bedroom 1.5 bath ranch on a corner lot. Nice size kitchen and living area. Updated LVP flooring on the main level, open floor plan and great lighting throughout the home. Spacious backyard, nice patio for entertainment, fenced in area for pets. Schedule your appointment today this won't last long!

  Sarah Cowman Homefront Real Estate, LLC

  324 W Filmore St, Winterset, IA 50273

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