Winterset, IA Homes

• 

  

  

  /24

  Est $325,735

  Not Listed For Sale

  225 N 14th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,415 Sq Ft
  • Built 2000

  225 N 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  

  /10

  $69,900

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  714 E Benton St, Winterset, IA 50273

  Tremendous potential in this cute little ranch home in the heart of Winterset. Sitting on a wonderful lot and brimming with potential. With a few basic cosmetics, this would be an excellent Investment property or starter home. Sold As Is.

  Ted Weaver RE/MAX Concepts

  714 E Benton St, Winterset, IA 50273
• 

  

  

  /30

  $285,000

  Sold Oct 31, 2025

  701 W Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 58 Days On Market

  Current Estimated Value $277,083

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  701 W Buchanan St, Winterset, IA 50273
• 

  

  

  /17

  Est $305,334

  Not Listed For Sale

  802 N 4th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1960

  802 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Lissa Baker RE/MAX Revolution
• 

  

  /2

  $69,000

  $6K PRICE DROP

  • Land
  • 3.45 Acres
  • $20,000 per Acre

  36 St, Winterset, IA 50273

  3.45 Acres – Bring Your Own Builder!LAKE LOT available in Covered Bridge Estates, a welcoming community with paved roads. Enjoy the feel of peaceful country living while still having quick, convenient access to the Des Moines metro. All information obtained from seller and public records.

  Rachel Eller Summerset Realty

  36 St, Winterset, IA 50273
• 

  

  /25

  $288,000

  Sold Nov 14, 2025

  722 W Mills St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 1993

  Last Sold Summary

  • 4% Below List Price
  • $230/SF
  • 24 Days On Market

  Current Estimated Value $282,448

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  722 W Mills St, Winterset, IA 50273
• 

  

  /35

  Est $454,528

  Not Listed For Sale

  1410 W Washington St, Winterset, IA 50273

  • 5 Beds
  • 4.5 Baths
  • 2,000 Sq Ft
  • Built 1979

  1410 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 317 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /31

  $199,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,131 Sq Ft

  816 S 4th Ave, Winterset, IA 50273

  This super cute, affordable 3-bedroom, 1-bath home packs a giant punch in a smart 1,131 sq ft package! Perfectly situated right in the heart of Winterset—midway between all local schools and directly across from the hospital—this gem is ideal for a first-time buyer or anyone seeking low-maintenance living with everything you need. Step inside through a convenient mudroom into a layout showcasing

  Ian Sparks Homefront Real Estate, LLC

  816 S 4th Ave, Winterset, IA 50273
• 

  

  /35

  $300,000

  Sold Nov 03, 2025

  2385 Holliwell Bridge Rd, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft
  • Built 1933

  Last Sold Summary

  • 6% Below List Price
  • $222/SF
  • 73 Days On Market

  Current Estimated Value $281,284

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  2385 Holliwell Bridge Rd, Winterset, IA 50273
• 

  

  /28

  Est $339,832

  Not Listed For Sale

  1427 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,414 Sq Ft
  • Built 1991

  1427 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Alyssa Tadlock Madison County Realty
• 

  

  /28

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,032 Sq Ft

  401 E Benton St, Winterset, IA 50273

  Welcome home to this warm and inviting ranch offering comfortable living space both upstairs and down! Built in 1995, this 4-bedroom(2 beds on 1st flr, 2 LL) 2-bath home features 1,032 square feet on the main level plus an impressive 936 square feet of finished lower-level space, giving you plenty of room to spread out. The spacious enclosed breezeway is a standout feature, creating the perfect

  Jennifer Stover Madison County Realty

  401 E Benton St, Winterset, IA 50273
• 

  

  /31

  $245,000

  Sold Jun 11, 2026

  317 E Washington St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1880

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 5 Days On Market

  Current Estimated Value $244,400

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  317 E Washington St, Winterset, IA 50273
• 

  

  /29

  Est $319,045

  Not Listed For Sale

  1233 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft
  • Built 1976

  1233 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 293 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /34

  $549,999

  $45K PRICE DROP

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

  505 E Court Ave, Winterset, IA 50273

  Step into timeless character with this stately 19th-century home, showcasing stunning original woodwork and rich architectural charm throughout. Set on an expansive lot, the property features a 4-car attached garage, a welcoming wrap around porch, and plenty of parking space. Inside, you’ll find a beautiful open floor plan designed for both everyday living and entertaining. The spacious living

  Sarah Cowman Homefront Real Estate, LLC

  505 E Court Ave, Winterset, IA 50273
• 

  

  /27

  $220,000

  Sold Jul 10, 2026

  619 N 10th St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,095 Sq Ft
  • Built 1880

  Last Sold Summary

  • 8% Below List Price
  • $201/SF
  • 104 Days On Market

  Current Estimated Value $222,639

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  619 N 10th St, Winterset, IA 50273
• 

  

  /32

  Est $478,537

  Not Listed For Sale

  924 Husky Dr, Winterset, IA 50273

  • 5 Beds
  • 3 Baths
  • 2,051 Sq Ft
  • Built 2004

  924 Husky Dr, Winterset, IA 50273

  Last Sold Summary

  • 537 Days On Market

  Last Listing Agent Betsy Breeding Realty ONE Group Impact
• 

  

  /35

  $337,500

  $12K PRICE DROP

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

  117 E North St, Winterset, IA 50273

  Welcome to timeless Americana charm in the heart of beautiful Winterset. Nestled on a quiet, tree lined street just moments from the beloved historic square, this spacious 2 sty offers warmth, character and a sense of community that make Winterset such a special place to call home. With 6 bedrooms and 3 baths, this home offers remarkable flexibility and room to grow. 4 bedrooms are on 2nd level

  Lisa Davis RE/MAX Precision

  117 E North St, Winterset, IA 50273
• 

  

  /35

  $725,000

  Sold Oct 15, 2025

  1813 Maple Ct, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft
  • Built 2017

  Last Sold Summary

  • 3% Below List Price
  • $417/SF
  • 22 Days On Market

  Current Estimated Value $741,349

  Last Listing Agent Amy Lucht Century 21 Signature

  1813 Maple Ct, Winterset, IA 50273
• 

  

  /26

  Est $301,763

  Not Listed For Sale

  803 S 3rd St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1961

  803 S 3rd St, Winterset, IA 50273

  Last Sold Summary

  • 212 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /30

  $324,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  423 E Jefferson St, Winterset, IA 50273

  Welcome home to this adorable 3-bedroom, 2-bath Arts & Crafts bungalow built in 1920, offering 1,913 sq ft of timeless charm and thoughtful updates. From the inviting covered porch and fenced front yard to the beautiful original details throughout, this home perfectly blends historic character with today’s conveniences. Step inside to find a warm and welcoming family room featuring wood beams, a

  Jennifer Stover Madison County Realty

  423 E Jefferson St, Winterset, IA 50273
• 

  

  /6

  $125,000

  Sold Nov 21, 2025

  Lot 5 114th Ct, Winterset, IA 50273

  • Land
  • 2.9 Acres
  • $43,103 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 363 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 5 114th Ct, Winterset, IA 50273
• 

  

  /19

  Est $291,880

  Not Listed For Sale

  1018 N 3rd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 2007

  1018 N 3rd Ave, Winterset, IA 50273

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Rusty Dickinson Realty ONE Group Impact
• 

  

  /7

  $160,000

  Pending

  • Land
  • 3.32 Acres
  • $48,193 per Acre

  2211 Cedar Bridge Rd, Winterset, IA 50273

  Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

  Jennifer Stover Madison County Realty

  2211 Cedar Bridge Rd, Winterset, IA 50273
• 

  

  /25

  $205,500

  Sold Oct 28, 2025

  417 S 2nd St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft
  • Built 1921

  Last Sold Summary

  • 4% Below List Price
  • $135/SF
  • 91 Days On Market

  Current Estimated Value $206,463

  Last Listing Agent Sue Monroe Spire Real Estate

  417 S 2nd St, Winterset, IA 50273
• 

  

  /21

  Est $279,928

  Not Listed For Sale

  926 N 3rd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2005

  926 N 3rd Ave, Winterset, IA 50273

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /33

  $474,000

  • 3 Beds
  • 2.5 Baths
  • 2,616 Sq Ft

  1818 Patricia Acres, Winterset, IA 50273

  WELCOME HOME to this beautiful, CUSTOM-BUILT home on 2.1 private acres. Did I mention how CLOSE it is to Winterset? The main floor has a nice sized LIVING ROOM and FORMAL DINING ROOM, with an abundance of windows, for plenty of NATURAL LIGHT. The kitchen with GRANITE countertops, STAINLESS STEEL APPLIANCES that stay, also has a nice breakfast nook and opens to the large family room with a wood

  Betsy Breeding Realty ONE Group Impact

  1818 Patricia Acres, Winterset, IA 50273
• 

  

  /19

  $298,000

  Sold Aug 29, 2025

  103 W Lane St, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 2,696 Sq Ft
  • Built 1908

  Last Sold Summary

  • $111/SF
  • 20 Days On Market

  Current Estimated Value $341,577

  Last Listing Agent Amanda Poganski Realty ONE Group Impact

  103 W Lane St, Winterset, IA 50273
• 

  

  /34

  Est $439,692

  Not Listed For Sale

  1145 W Summit St, Winterset, IA 50273

  • 4 Beds
  • 4.5 Baths
  • 2,532 Sq Ft
  • Built 1867

  1145 W Summit St, Winterset, IA 50273

  Last Sold Summary

  • 237 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /29

  $449,900

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,743 Sq Ft

  703 N 10th Ave, Winterset, IA 50273

  Easy living in this spacious ranch home. You will love the covered front porch as you are greeted at the front door. The open floorplan is great for entertaining! Generous kitchen with beautiful back splash, SS appliances and pantry! The dining area is right off the kitchen with door to the covered deck - perfect for grilling! The living room has a cozy gas fireplace with beautiful built ins

  Sarah Cowman Homefront Real Estate, LLC

  703 N 10th Ave, Winterset, IA 50273
• 

  

  /17

  $84,000

  Sold Dec 19, 2025

  315 N 4th Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1888

  Last Sold Summary

  • 20% Below List Price
  • $78/SF
  • 176 Days On Market

  Current Estimated Value $115,755

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  315 N 4th Ave, Winterset, IA 50273
• 

  

  /17

  Est $273,966

  Not Listed For Sale

  818 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft
  • Built 1950

  818 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /35

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft

  310 W Washington St, Winterset, IA 50273

  A truely unique and well kept historic home is ready for new owners. The character is abundant in this sprawling 2 story home. Walk in the front door and you will be greeted by a sweet vestibule for sitting and taking off shoes and hanging up your jacket. You will be greeted with a large front living room with stunning gas fireplace and lots of windows for natural light. There is an

  Sarah Cowman Homefront Real Estate, LLC

  310 W Washington St, Winterset, IA 50273
• 

  

  /32

  $320,000

  Sold Jul 13, 2026

  59 E Benton St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • Built 1909

  Last Sold Summary

  • 4% Below List Price
  • $167/SF
  • 7 Days On Market

  Current Estimated Value $327,164

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  59 E Benton St, Winterset, IA 50273
• 

  

  /35

  Est $418,411

  Not Listed For Sale

  924 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 3.5 Baths
  • 1,664 Sq Ft
  • Built 1956

  924 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /29

  $299,900

  Pending

  • 4 Beds
  • 2 Baths
  • 2,281 Sq Ft

  322 W Washington St, Winterset, IA 50273

  Step into the timeless charm of this beautiful 4-bedroom, 2-bath Victorian home in the heart of Winterset! Blending classic character with thoughtful updates, this home features original hardwood floors, newer exterior paint, light fixtures, refrigerator, storm doors, and a fully fenced quarter-acre yard. The roof was replaced in 2020, giving added peace of mind. Outside, you'll find fruit trees,

  Tony Berry RE/MAX Concepts

  322 W Washington St, Winterset, IA 50273
• 

  

  /32

  $485,000

  Sold Nov 03, 2025

  301 Magnolia Point, Winterset, IA 50273

  • 6 Beds
  • 3.5 Baths
  • 2,351 Sq Ft
  • Built 2020

  Last Sold Summary

  • 9% Below List Price
  • $206/SF
  • 146 Days On Market

  Current Estimated Value $495,838

  Last Listing Agent Rachel Eller Summerset Realty

  301 Magnolia Point, Winterset, IA 50273
• 

  

  /26

  Est $366,654

  Not Listed For Sale

  925 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft
  • Built 1972

  925 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /17

  $229,100

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  59 E North St, Winterset, IA 50273

  Welcome home to this beautifully maintained 3-bedroom, 2-bath, 1.5-story home filled with charm and curb appeal! Step outside and enjoy the beautifully landscaped, fully fenced yard—perfect for relaxing, entertaining, pets, or play. The open patio with pergola creates a wonderful outdoor gathering space, while the newer storm shelter and storage shed add extra peace of mind and convenience. A

  Rachel Eller Summerset Realty

  59 E North St, Winterset, IA 50273
• 

  

  /13

  $210,000

  Sold Jun 24, 2026

  411 W Madison St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $204/SF
  • 188 Days On Market

  Last Listing Agent Alyssa Tadlock Madison County Realty

  411 W Madison St, Winterset, IA 50273
• 

  

  /35

  Est $270,122

  Not Listed For Sale

  901 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1958

  901 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Jon Niemeyer EXIT Realty & Associates

Showing Results 81 - 120, Page 3 of 18