Madison, IA Homes

• 

  

  

  /34

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,451 Sq Ft

  520 W Benton St, Winterset, IA 50273

  Charming 1.5 Story Home with Space for Everyone! This adorable 4-bedroom, 2-bath home offers a versatile layout perfect for families or anyone looking for room to grow. Enjoy a spacious main floor living room and two main-level bedrooms with hardwood floors hidden beneath the carpet—ready to be revealed if you love that classic touch. The eat-in kitchen features ample counter space, ideal for

  Misty Darling BH&G Real Estate Innovations

  520 W Benton St, 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
• 

  

  

  /21

  Est $265,697 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  926 N 3rd Ave, Winterset, IA 50273

  926 N 3rd Ave, Winterset, IA 50273
• 

  

  

  /4

  $74,500

  • Land
  • 3.00 Acres
  • $24,833 per Acre

  1796 Millstream Ct, Winterset, IA 50273

  Beautiful 3-acre lot located in the desirable Covered Bridge Estates! This scenic property offers the perfect blend of country feel with community convenience. Ideal for building your dream home with room to spread out—bring your own builder! Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town, with easy access to

  Rachel Eller Summerset Realty

  1796 Millstream Ct, 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
• 

  

  /34

  Est $560,368 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths

  1145 W Summit St, Winterset, IA 50273

  1145 W Summit St, Winterset, IA 50273
• 

  

  /35

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 3,298 Sq Ft

  2218 N John Wayne Dr, Winterset, IA 50273

  Welcome to this exceptional 3300 sq ft 3/4-bedroom, 4-bath brick ranch that perfectly balances privacy, convenience, and expansive living. Situated on private acreage within city limits but just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways.From the moment you step through the grand entry, you'll appreciate

  Alyssa Tadlock Madison County Realty

  2218 N John Wayne Dr, 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
• 

  

  /33

  Est $361,426 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,102 Sq Ft

  1169 W Summit St, Winterset, IA 50273

  1169 W Summit St, Winterset, IA 50273
• 

  

  /18

  $195,000

  • Land
  • 4.88 Acres
  • $39,959 per Acre

  4922 Cedar Ln, Winterset, IA 50273

  Looking for the perfect mix of privacy, space, and convenience? This stunning 4.88-acre lot at the end of a quiet cul-de-sac offers just that. Located on a paved road between West Des Moines and Winterset, this property features a beautiful blend of open grassland and mature timber, ideal for creating your custom retreat.There's room for it all: your dream home, an outbuilding, or even a

  Timothy Scheib RE/MAX Precision

  4922 Cedar Ln, Winterset, IA 50273
• 

  

  /24

  $280,000 Sold Jun 11, 2025

  • 2,212 Sq Ft
  • $127/SF
  • 271 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1930

  217 E Jefferson St, Winterset, IA 50273

  Seller offering $5000 worth of buyer’s concessions for closing costs or beautification to make home their own! Unique property; two homes 1 lot. Main home is 5 bedroom, 2 remodeled baths with new carpet and flooring throughout. Kitchen has been remodeled with new cabinets, new dishwasher w/warranty and new stove and refrigerator. New Washer and Dryer are also included! Other updates in the main

  Sarah Cowman Homefront Real Estate, LLC

  217 E Jefferson St, Winterset, IA 50273
• 

  

  /28

  Est $295,749 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,311 Sq Ft

  907 W Washington St, Winterset, IA 50273

  907 W Washington St, Winterset, IA 50273
• 

  

  /29

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  66 E High St, Winterset, IA 50273

  Charming and fully updated 1.5 story home on a large corner lot in historic Winterset--roughly 30 minutes from the Des Moines metro! This 3-bed, 2-bath home features a spacious living room and a wrap-around layout that flows seamlessly from the living area to the updated kitchen with newer stainless steel appliances, and into the dining space. Stylish LVP flooring throughout the main level adds

  Cameron Campos RE/MAX Concepts

  66 E High St, Winterset, IA 50273
• 

  

  /28

  $260,000 Sold Jun 05, 2025

  • 1,500 Sq Ft
  • $173/SF
  • 19 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1964

  421 W Buchanan St, Winterset, IA 50273

  This charming and beautifully updated 2-story home in Winterset has everything you need and is perfect for entertaining indoors or out! The main level features a spacious living room, great size eat-in kitchen, and a convenient half bath. Upstairs, you'll find four large bedrooms?three with stunning hardwood floors and all with generous closet space, and a full bath. The finished basement

  Stephanie Anania RE/MAX Revolution

  421 W Buchanan St, Winterset, IA 50273
• 

  

  /25

  Est $487,552 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,595 Sq Ft

  614 W Benton St, Winterset, IA 50273

  614 W Benton St, Winterset, IA 50273
• 

  

  /30

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft

  701 W Buchanan St, Winterset, IA 50273

  Easy living in this Ranch with many updates including roof, siding, gutters, furnace, a/c in 2021, yard drainage system, and updates to the electrical. This unique ranch home has a large front porch that is great for sipping coffee and chatting with the neighbors! Inside you will love the large front living room with wood burning fireplace that is adjacent to the formal dining room that flows

  Sarah Cowman Homefront Real Estate, LLC

  701 W Buchanan St, Winterset, IA 50273
• 

  

  /29

  $174,900 Sold Jun 03, 2025

  • 784 Sq Ft
  • $223/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  501 W Summit St, Winterset, IA 50273

  This well-maintained two-bedroom ranch is the perfect place to call home! Conveniently located near schools, this home features a cozy living space, an efficient kitchen, and a full bath. Enjoy the ease of single-level living with the added bonus of a detached one-car garage, providing extra storage space. The spacious fenced in yard offers room to relax, garden, or entertain. Whether you're a

  Rachel Eller Summerset Realty

  501 W Summit St, Winterset, IA 50273
• 

  

  /3

  Est $130,015 Not Listed For Sale

  1019 N 4th Ave, Winterset, IA 50273

  1019 N 4th Ave, Winterset, IA 50273
• 

  

  /35

  $749,900

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  1813 Maple Ct, Winterset, IA 50273

  Welcome to your private escape in Covered Bridge Estates- where peaceful acreage, custom living, and endless opportunity meet.This rare offering includes two lots, totaling over 6.25 acres of scenic rural residential land just minutes from Winterset. Tucked into the heart of Madison County, this property features a custom-built 1,740 sq ft ranch with thoughtful upgrades throughout: a

  Amy Lucht RE/MAX Precision

  1813 Maple Ct, Winterset, IA 50273
• 

  

  /35

  $549,000 Sold Jun 02, 2025

  • 1,344 Sq Ft
  • $408/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1910

  2640 206th St, Winterset, IA 50273

  Step right into your own magical country oasis compete with party barn, pond and amazing views! This sweet homestead has so much to offer! Located directly off of highway 92 - barely any gravel! The completely renovated 3 bedroom 1 bath home is bursting with character & has the most stunning southern views! Walk into the cozy living room with tons of natural light & enjoy the ambiance of the

  Sarah Cowman Homefront Real Estate, LLC

  2640 206th St, Winterset, IA 50273
• 

  

  /20

  Est $230,408 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  501 W Buchanan St, Winterset, IA 50273

  501 W Buchanan St, Winterset, IA 50273
• 

  

  /21

  $180,000

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  601 E Green St, Winterset, IA 50273

  This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft of thoughtfully designed living space. Full of character, the home features an eat-in kitchen, a cozy living room with plenty of natural light, and a bonus room that can easily serve as an office or an extra bedroom. The updated bathroom and fresh flooring throughout the main level add modern convenience.

  Theodore Craig Developers Realty Group LLC

  601 E Green St, Winterset, IA 50273
• 

  

  /28

  $294,000 Sold Jun 02, 2025

  • 1,464 Sq Ft
  • $201/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  1210 W Jefferson St, Winterset, IA 50273

  Move in ready Winterset Home blocks from the Historic Square & across the street from the city pool, park, tennis & Pickleball courts! With over 1,900 sq ft finish, this 3 BR (4th non-conforming) 2.5 BA home has all the updates to make this a peace of mind investment. Updates by the current seller include new roof, garage door, carpet throughout, garage epoxy & radon mitigation system. Updates

  Ou Meksay RE/MAX Concepts

  1210 W Jefferson St, Winterset, IA 50273
• 

  

  /22

  Est $216,595 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  618 N 4th Ave, Winterset, IA 50273

  618 N 4th Ave, Winterset, IA 50273
• 

  

  /14

  $235,000

  • 3 Beds
  • 1.5 Baths
  • 912 Sq Ft

  1021 W South St, Winterset, IA 50273

  Come enjoy small town living in Winterset in this adorable 3 bedroom ranch home! The spacious living area has tons of natural light with the large windows and beautiful hardwood floors. Find three bedrooms and a full bath on the main floor, as well as the farmhouse style kitchen featuring white subway tile backsplash and white cabinets. The lower level features an extra living space, half bath,

  Jenna Carney Keller Williams Realty GDM

  1021 W South St, Winterset, IA 50273
• 

  

  /35

  $314,900 Sold Jun 02, 2025

  • 1,278 Sq Ft
  • $246/SF
  • 91 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2020

  602 W Stone St, Winterset, IA 50273

  Welcome to 602 W Stone St – a stunning corner unit bi-attached ranch townhome in the heart of historic Winterset! This beautifully maintained, turn-key property offers nearly 2,400 sq. ft. of finished living space with 3 bedrooms, 3 bathrooms, and a 2-car attached garage. Step into the stylish kitchen featuring painted maple cabinets, white quartz countertops, and abundant storage—ideal for both

  Ryan Rohlf Keller Williams Legacy Group

  602 W Stone St, Winterset, IA 50273
• 

  

  /25

  Est $211,708 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  1016 W South St, Winterset, IA 50273

  1016 W South St, Winterset, IA 50273
• 

  

  /35

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  1821 Millstream Ct, Winterset, IA 50273

  Prepare to be taken back by this distinguished two-story residence, masterfully crafted and lavishly finished with beautiful living space. Setting on three breathtaking acres, every inch of this estate exudes luxury and warmth—from the inviting front porch to expansive decks, professionally designed landscaping, a cozy inviting firepit, and an astounding garage capacity for seven vehicles—yes,

  Sarah Cowman Homefront Real Estate, LLC

  1821 Millstream Ct, Winterset, IA 50273
• 

  

  /21

  $60,000 Sold May 30, 2025

  • 1,174 Sq Ft
  • $51/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1904

  110 E Grade St, Winterset, IA 50273

  3 BR 1 bath one story frame home in Winterset. It has a large kitchen with entrance to basement from inside the home. Rear yard with front and back decks. Home is being sold "AS IS". Some upgrades within the last ten years to mechanicals and exterior features. Hardwood floors in many areas. Bonus room off SW corner of the home. Priced below assessed value. Come to view.

  Toni Tindle Covered Bridge Realty

  110 E Grade St, Winterset, IA 50273
• 

  

  /21

  Est $205,417 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 964 Sq Ft

  110 N 10th Ave, Winterset, IA 50273

  110 N 10th Ave, Winterset, IA 50273
• 

  

  /31

  $128,000

  • 2 Beds
  • 1 Bath
  • 942 Sq Ft

  59 E Washington St, Winterset, IA 50273

  Great opportunity for an investor or a first-time buyer looking to make a place their own!! This 942 sq ft ranch-style home offers potential, and an opportunity to build equity with a little TLC. The main level features a spacious living room with built-ins, a generously sized bedroom with double closets, and an eat-in kitchen ready for your personal touch. Toward the back of the home, youll

  John Brummett RE/MAX Precision

  59 E Washington St, Winterset, IA 50273
• 

  

  /14

  $121,000 Sold May 30, 2025

  • 664 Sq Ft
  • $182/SF
  • 147 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1880

  603 W Hutchings St, Winterset, IA 50273

  Charming and updated home nestled in a quiet, small-town neighborhood. This cozy residence features modern finishes, a spacious master bedroom and a functional layout perfect for comfortable living. Enjoy a modern renovated kitchen, updated flooring, and well-maintained systems throughout. The backyard offers a great space for relaxation or entertaining. With its affordable price and convenient

  Anthony Dennis RE/MAX Revolution

  603 W Hutchings St, Winterset, IA 50273
• 

  

  /24

  Est $245,081 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,260 Sq Ft

  906 W Court Ave, Winterset, IA 50273

  906 W Court Ave, Winterset, IA 50273
• 

  

  /25

  $213,000

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft

  417 S 2nd St, Winterset, IA 50273

  A must-see home in a fantastic location, just moments from the historic John Wayne birthplace and just blocks away from the bustling downtown square. Walk up to your “new “front porch that welcomes you with new columns, railings, and a porch swing that you'll never want to leave! Perfect spot for your morning coffee , reading your favorite book or lounging at the end of a long day. As you enter,

  Sue Monroe Spire Real Estate

  417 S 2nd St, Winterset, IA 50273
• 

  

  /31

  $305,000 Sold May 28, 2025

  • 1,904 Sq Ft
  • $160/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1967

  602 W Hutchings St, Winterset, IA 50273

  Absolutely stunning ranch on a large corner lot in the heart of Winterset! Plenty of space with over 2600 of finished living space! 3 bedrooms on the main level with 2 bathrooms, eat in kitchen with TONS of storage, beautiful hardwood floors leading into the extra living room/dining area. You will LOVE the family room with stone fireplace with plenty of room to entertain! Partially finished

  Susan Sheldahl Realty One Group Impact

  602 W Hutchings St, Winterset, IA 50273
• 

  

  /35

  Est $264,112 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  704 N 4th Ave, Winterset, IA 50273

  704 N 4th Ave, Winterset, IA 50273
• 

  

  /10

  $299,000

  • Land
  • 10 Acres
  • $29,900 per Acre

  TBD Iowa 92, Winterset, IA 50273

  Build Your Dream Home on this Scenic 10-Acre Parcel!Located just off paved Highway 92 and only 25 minutes from the Des Moines metro, this beautiful ±10 acre lot offers the perfect mix of convenience and peaceful country living. With scenic views, open space, and rural water and electric at the road, it’s an ideal setting for your future home, hobby farm, or weekend retreat.Plenty of

  Rachel Eller Summerset Realty

  TBD Iowa 92, Winterset, IA 50273
• 

  

  /23

  $190,000 Sold May 23, 2025

  • 992 Sq Ft
  • $192/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1947

  323 E Jefferson St, Winterset, IA 50273

  Charming Brick Bungalow Full of Character on a Prime Corner Lot! Step into timeless charm with this beautifully maintained brick bungalow just a short walk from the town square. Bursting with original character, this home features gorgeous hardwood floors, elegant crystal door knobs, and classic built-ins that tell a story of craftsmanship and care. The main floor offers two comfortable bedrooms

  Deanna Roth Century 21 Signature

  323 E Jefferson St, Winterset, IA 50273
• 

  

  /31

  Est $215,865 Not Listed For Sale

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

  322 W South St, Winterset, IA 50273

  322 W South St, Winterset, IA 50273
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18