Winterset, IA Homes

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  /28

  $169,000 Sold Oct 21, 2025

  415 W Summit St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 810 Sq Ft
  • Built 1982

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Current Estimated Value $172,686

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  415 W Summit St, Winterset, IA 50273
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  /25

  Est $336,470 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
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  /24

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  212 N 14th Ave, Winterset, IA 50273

  Sweet ranch home located on a quiet street. The open concept floor plan makes this house feel bigger than it is. The 1st floor offers 2 large bedrooms, 1 full bath, kitchen with a breakfast bar and a private home office space. The lower level features a huge family room, large bedroom and full bath - and still plenty of storage space. Sliding door off the dining area leads to the private

  Jennifer Stover Madison County Realty

  212 N 14th Ave, Winterset, IA 50273
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  /25

  $575,000 Sold Nov 20, 2025

  2283 Pioneer Ave, Winterset, IA 50273

  • Land
  • 20 Acres
  • $28,750 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 40 Days On Market

  Last Listing Agent Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273
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  /24

  Est $321,889 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
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  /29

  $299,000

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  203 W Green St, Winterset, IA 50273

  You will love all the space in this UNIQUE 2000+ sq ft home on a large corner lot! Main level includes a massive family room, large kitchen with dinning area and a separate room that could be a formal dining room or office and a half bath. Upstairs there are 3 large bedrooms (one with en suite and walk in closet) plus another smaller room that could also be a bedroom, game room, office or craft

  Alyssa Tadlock Madison County Realty

  203 W Green St, Winterset, IA 50273
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  /6

  $100,000 Sold Aug 01, 2025

  Lot 1 114th Ct, Winterset, IA 50273

  • Land
  • 5.32 Acres
  • $18,797 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 269 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 1 114th Ct, Winterset, IA 50273
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  /17

  Est $297,631 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
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  /2

  $335,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,802 Sq Ft

  1001 N 8th Ave, Winterset, IA 50273

  Andrew DePhillips RE/MAX Concepts

  1001 N 8th Ave, Winterset, IA 50273
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  /27

  $269,000 Sold Oct 16, 2025

  822 N 3rd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 2005

  Last Sold Summary

  • $191/SF
  • 4 Days On Market

  Current Estimated Value $264,503

  Last Listing Agent Bruce Seymour RE/MAX Precision

  822 N 3rd Ave, Winterset, IA 50273
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  /12

  Est $223,773 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
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  /35

  $279,000

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  513 E Jefferson St, Winterset, IA 50273

  Motivated sellers! Welcome to this huge 3 bed, 3 bath home with a great, beautiful lot in the heart of Winterset (one of the BEST small towns in us)! What a GEM! One of lowest price per SF renovated homes on the market! Hardwood floors, original trim, large entryway, vaulted ceilings, oversized living room with beautiful windows, sunroom has all new windows & flooring for office, kid’s space or

  Alison Frank Platinum Realty LLC

  513 E Jefferson St, Winterset, IA 50273
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  /23

  $270,000 Sold Sep 18, 2025

  0000 Hogback Bridge Rd, Winterset, IA 50273

  • Land
  • 22.01 Acres
  • $12,267 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 4 Days On Market

  Last Listing Agent Dennis Williams Midwest Land Group LLC

  0000 Hogback Bridge Rd, Winterset, IA 50273
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  /34

  Est $286,377 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
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  /35

  $1,385,000 Pending

  • Land
  • 29.7 Acres
  • $46,633 per Acre

  1890 Hogback Bridge Rd, Winterset, IA 50273

  Rare 30-acre M/L retreat in Madison County Iowa with a 4,000+ sq. ft. custom home. Incredible views of the countryside teeming with wildlife including white-tailed deer and turkey. Main level features gourmet kitchen with 2 dishwashers & walk-in pantry, spacious living areas, and a primary suite with sitting room, spa bath, huge walk-in closet & laundry. Upstairs offers loft with wet bar, 4

  Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
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  /31

  $310,000 Sold Jun 30, 2025

  221 N 15th Ave, Winterset, IA 50273

  • 5 Beds
  • 2.5 Baths
  • 1,415 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $219/SF
  • 54 Days On Market

  Current Estimated Value $313,632

  Last Listing Agent Danielle Burnight RE/MAX Concepts

  221 N 15th Ave, Winterset, IA 50273
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  /29

  Est $448,394 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
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  /35

  $560,000

  • Land
  • 4.29 Acres
  • $130,536 per Acre

  2237 Holliwell Valley Ct, Winterset, IA 50273

  If you are dreaming of countryside peace and quiet and need alot of living space, you will definately enjoy the beauty and freedom of a 4.3-acre homestead featuring 6 bedrooms, 4 baths, and multiple living areas. The elegant kitchen boasts a walk-in pantry, an abundance of countertop and cabinet space, and picturesque views of rolling hills and a neighboring pond. Step out from the dining area

  Sarah Cowman Homefront Real Estate, LLC

  2237 Holliwell Valley Ct, Winterset, IA 50273
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  /22

  $125,000 Sold Oct 07, 2025

  103 S 3rd St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,093 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 82 Days On Market

  Current Estimated Value $123,200

  Last Listing Agent Zineta Imamovic Realty ONE Group Impact

  103 S 3rd St, Winterset, IA 50273
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  /32

  Est $479,337 Not Listed For Sale

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

  924 Husky Dr, Winterset, IA 50273

  924 Husky Dr, Winterset, IA 50273
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  /2

  $70,500

  • Land
  • 3.45 Acres
  • $20,435 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
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  /35

  $245,500 Sold Mar 14, 2025

  901 W Jefferson St, Winterset, IA 50273

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

  Last Sold Summary

  • 2% Below List Price
  • $231/SF
  • 11 Days On Market

  Current Estimated Value $248,836

  Last Listing Agent Jon Niemeyer EXIT Realty & Associates

  901 W Jefferson St, Winterset, IA 50273
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  /26

  Est $270,090 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 960 Sq Ft

  803 S 3rd St, Winterset, IA 50273

  803 S 3rd St, Winterset, IA 50273
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  /7

  $160,000

  • 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
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  /35

  $217,000 Sold Jan 15, 2026

  324 S 10th Ave, Winterset, IA 50273

  • 1 Bed
  • 2.5 Baths
  • 1,213 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 27 Days On Market

  Last Listing Agent Toni Tindle Covered Bridge Realty

  324 S 10th Ave, Winterset, IA 50273
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  /19

  Est $284,763 Not Listed For Sale

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

  1018 N 3rd Ave, Winterset, IA 50273

  1018 N 3rd Ave, Winterset, IA 50273
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  /21

  $2

  • Land
  • 230.9 Acres
  • $0 per Acre

  2107 265th St, Winterset, IA 50273

  The currently tilled farmland consists of low-80s to low-90s CSR2 soils. This highly productive ground has the ability to perform year after year. This is a farm that not only produces, but has the soil quality to sustain long-term appreciation and value. For the lifestyle and recreational buyer, the eastern tract is truly special. It offers an outstanding hunting setup with excellent access,

  Jason Smith DreamDirt Farm & Ranch Real Estate

  2107 265th St, Winterset, IA 50273
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  /25

  $213,865 Sold Jun 13, 2025

  707 E Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 13 Days On Market

  Current Estimated Value $183,002

  Last Listing Agent Jenn Ho Goh GoSynergy Realty

  707 E Buchanan St, Winterset, IA 50273
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  /21

  Est $275,207 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
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  /13

  $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 home! 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

  Alyssa Tadlock Madison County Realty

  411 W Madison St, Winterset, IA 50273
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  /34

  $250,000 Sold Sep 22, 2025

  520 W Benton St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1966

  Last Sold Summary

  • $172/SF
  • 19 Days On Market

  Current Estimated Value $250,544

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  520 W Benton St, Winterset, IA 50273
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  /34

  Est $545,038 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths

  1145 W Summit St, Winterset, IA 50273

  1145 W Summit St, Winterset, IA 50273
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  /33

  $649,999

  • Land
  • 11.44 Acres
  • $56,818 per Acre

  1634 170th St, Winterset, IA 50273

  Scenic Winterset Acreage – Earlham Schools - Ranch Home on 11+ Acres with Walkout Basement & Hobby Farm Features!Discover your dream homestead just minutes from Winterset! This beautifully maintained ranch-style home sits on 11.2 acres of rolling countryside and offers 4 bedrooms, 3 full bathrooms, and a fully finished walkout basement.Step into the heart of the home — a chef’s kitchen

  Kate Carlson Realty ONE Group Impact

  1634 170th St, Winterset, IA 50273
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  /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 $281,664

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  701 W Buchanan St, Winterset, IA 50273
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  /33

  Est $331,440 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
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  /35

  $1,050,000

  • Land
  • 19.5 Acres
  • $53,846 per Acre

  2230 260th St, Winterset, IA 50273

  Situated on 20 acres, this 11⁄2-story home offers nearly 4,800 sq ft of finished living space designed with scale, quality and comfort in mind. The main level features vaulted wood ceilings, exposed beams, hardwood floors and a stone fireplace that anchors the living area. An open kitchen with solid wood cabinetry, island and generous counter space connects seamlessly to the dining and living

  Julie Egli RE/MAX Precision

  2230 260th St, Winterset, IA 50273
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  /25

  $185,000 Sold Aug 25, 2025

  507 W Madison St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 2021

  Last Sold Summary

  • 12% Below List Price
  • $180/SF
  • 83 Days On Market

  Current Estimated Value $200,528

  Last Listing Agent Toni Tindle Covered Bridge Realty

  507 W Madison St, Winterset, IA 50273
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  /17

  Est $267,301 Not Listed For Sale

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

  818 W Jefferson St, Winterset, IA 50273

  818 W Jefferson St, Winterset, IA 50273
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  /7

  $170,000

  • Land
  • 3.76 Acres
  • $45,213 per Acre

  Lot 27 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

  Julie Baudler RE/MAX Concepts

  Lot 27 114th Ct, Winterset, IA 50273
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  /29

  $85,000 Sold Mar 28, 2025

  808 S 5th Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1890

  Last Sold Summary

  • 34% Below List Price
  • $69/SF
  • 95 Days On Market

  Current Estimated Value $323,000

  Last Listing Agent Roger Queck Pro Team Realty

  808 S 5th Ave, Winterset, IA 50273

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