Winterset, IA Homes

• 

  

  

  /31

  $234,000

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  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

  (515) 375-1789

  318 W Green St, Winterset, IA 50273
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• 

  

  

  /18

  $799 - $899 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
• 

  

  

  /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 $413,141 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 2,625 Sq Ft

  923 S 4th Ave, Winterset, IA 50273

  923 S 4th Ave, Winterset, IA 50273
• 

  

  

  /25

  $210,000

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft

  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

  (515) 385-4853

  507 W Madison St, Winterset, IA 50273
• 

  

  /4

  $1,074 per month

  • 1-2 Beds
  • 2 Baths
  • 640 Sq Ft
  • Condo for Rent

  428 W Mills St, Winterset, IA 50273

  Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is

  428 W Mills 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
• 

  

  /23

  Est $175,293 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 981 Sq Ft

  201 S 4th St, Winterset, IA 50273

  201 S 4th St, Winterset, IA 50273
• 

  

  /35

  $319,000

  • 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
• 

  

  /4

  $1,074 per month

  • 1-2 Beds
  • 2 Baths
  • 640 Sq Ft
  • Condo for Rent

  428 W Mills St, Winterset, IA 50273

  Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is

  428 W Mills 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
• 

  

  /12

  Est $237,783 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
• 

  

  /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
• 

  

  /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
• 

  

  /26

  Est $404,991 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2647 Bittersweet Ave, Winterset, IA 50273

  2647 Bittersweet Ave, Winterset, IA 50273
• 

  

  /30

  $474,000

  • 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, walk-in shower & also features a bidet in master bath. Main floor laundry off the kitchen. Other features on the 1st

  

  Toni Tindle

  Covered Bridge Realty

  (515) 824-5239

  1913 N 1st 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
• 

  

  /35

  Est $551,876 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2395 148th St, Winterset, IA 50273

  2395 148th St, Winterset, IA 50273
• 

  

  /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
• 

  

  /35

  $750,000 Sold Jun 13, 2025

  • 1,534 Sq Ft
  • $489/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  2176 148th St, Winterset, IA 50273

  This M/L 18 acres has something for everyone! You have the wildlife, timber, a pond for fishing, grass & alfalfa mix for your horses or to sell. A nice almost new 30 by 40 pole barn with 2 >10ft by 10ft doors, a concrete floor, electric and outside RV hookups. A detached 2 car garage, 2 sheds, ample parking for extra trailers and several fruit trees. The home has over 2600 sq foot of finished

  Lisa Pierce Honer Summit Realty

  2176 148th St, Winterset, IA 50273
• 

  

  /33

  Est $382,515 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
• 

  

  /35

  $1,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,244 Sq Ft

  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

  $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 $352,891 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
• 

  

  /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
• 

  

  /35

  Est $392,732 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
• 

  

  /12

  $195,000

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

  4922 Cedar Ln, Winterset, IA 50273

  If you're ready to build your dream home, this stunning 4.88-acre lot is a must-see! Located on a paved road between West Des Moines and Winterset, this end of cul-de-sac property features a perfect blend of grassland and timber. With ample space for your home, an outbuilding, or even a pool, you'll enjoy beautiful views and the charm of local wildlife, all while having convenient access to the

  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
• 

  

  /29

  Est $438,081 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
• 

  

  /23

  $320,000

  • 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 great big 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

  Alyssa Tadlock Madison County Realty

  203 W Green 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
• 

  

  /35

  Est $509,854 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
• 

  

  /20

  $550,000

  • 3 Beds
  • 2 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 owners currently live in the house and Airbnb the 4 units. Each rental unit is 360 sf, with a kitchenette, living area, 1 bedroom and 3/4 bath. Sweet covered front porch. The 5th

  Jennifer Stover Madison County Realty

  715 N John Wayne Dr, 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
• 

  

  /17

  Est $298,864 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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  Est $217,423 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

  $349,900

  • 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

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