Homes for Sale in 50273

• 

  

  

  /25

  $192,000

  • 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
• 

  

  

  /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

  $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
• 

  

  

  /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
• 

  

  

  /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, 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
• 

  

  /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
• 

  

  /16

  $675,000

  • Land
  • 60 Acres
  • $11,183 per Acre

  0 Ironwood Trail, Earlham, IA 50072

  Peoples Company and Madison County Realty, Inc are pleased to present 60.36 acres m/l of coveted Madison County, Iowa land perfect for hunting, recreation, or building a home. Conveniently located just 10 minutes north of Winterset and less than 30 minutes from the Des Moines Metro, this property offers almost 45 acres of dense timber and an estimated 12.61 acres of income-producing CRP, subject

  Bryan Bergdale Peoples Company

  0 Ironwood Trail, Earlham, IA 50072
• 

  

  /35

  $675,000

  • 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

  $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
• 

  

  /35

  $385,000

  • 2 Beds
  • 3 Baths
  • 1,531 Sq Ft

  701 North St, Patterson, IA 50218

  Rare In-Town Acreage with Pole Barn – Just Minutes from WDSM & Winterset! This unique property offers the best of both worlds—peaceful acreage living with quick access to West Des Moines (15 mins) and Winterset (5 mins). Located on the edge of town, this well-maintained acreage sits on two separate parcels, offering flexibility for personal use, rental income, or resale. The spacious 48’x80’x12’

  Becky Knight Iowa Realty Mills Crossing

  701 North St, Patterson, IA 50218
• 

  

  /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
• 

  

  /35

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  2385 Holliwell Bridge Rd, Winterset, IA 50273

  Welcome to your dream country escape! You’ll fall in love with the scenic backdrop and peaceful surroundings! Nestled on 3.17 acres, this beautifully updated 1.5 story home offers the peace and privacy of rural living with the convenience of being close to town. Inside, the home features several key updates including a new roof (March 2025), new water lines, a newer heating & cooling with a

  Misty Darling BH&G Real Estate Innovations

  2385 Holliwell Bridge Rd, Winterset, IA 50273
• 

  

  /35

  $650,000

  • 4 Beds
  • 3 Baths
  • 1,878 Sq Ft

  1694 McBride Ridge Ct, Winterset, IA 50273

  Acreage for sale in Winterset Iowa! Discover your own slice of country paradise just 100 yards off paved Cumming Road! This 4-bedroom, 3-bath walkout ranch sits on nearly 5 acres—about 90% fenced—and is a dream for nature lovers, hobby gardeners, and dog enthusiasts alike. Built in 2003, this spacious home boasts over 3,300 sq ft of finished living space. The main level features a cozy family

  Michelle Price Realty ONE Group Impact

  1694 McBride Ridge Ct, 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
• 

  

  /35

  $659,900

  • 4 Beds
  • 3 Baths
  • 1,788 Sq Ft

  2626 160th St, van Meter, IA 50261

  Open concept Ranch with a little more than 1800 square feet upstairs with a finished basement. Upstairs consists of large master bedroom with tray ceiling and his and her closets. Primary bedroom is huge and has its own bathroom with jetted tub, walk in shower and built in make up counter, toilet has an individual door for that added privacy. Large bedroom and bathroom with large linen closet

  Sarah Cowman Homefront Real Estate, LLC

  2626 160th St, van Meter, IA 50261
• 

  

  /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

  $345,900

  • 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
• 

  

  /33

  $348,000

  • 4 Beds
  • 2.5 Baths
  • 2,026 Sq Ft

  708 W Fremont St, Winterset, IA 50273

  Tons of room to spread out in this 4 bed 3 bath home. Walk into the gathering room that has many uses. It could be a formal dining room or a great sitting area. The spacious kitchen has plenty of cabinets and counter tops space and all appliances are included. The dining area can accommodate a large table. There is a huge mudroom off the kitchen as well as a 3/4 bath. The living room is huge

  Sarah Cowman Homefront Real Estate, LLC

  708 W Fremont St, Winterset, IA 50273
• 

  /2

  $384,500

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  304 Maple Pointe, Winterset, IA 50273

  Stryker Ranch with over-sized 3 car garage. Front porch with 2 stone base posts. 9'ceilings throughout main floor. Open stairs to basement. Granite or quartz counter tops in baths and kitchen. Kitchen boasts of a large walk-in pantry and stainless-steel appliances. White cabinets throughout. Luxury vinyl flooring. Gas fireplace. Master bath with raised vanity and elongated stool. High-efficiency

  Robert D. Weeks Iowa Realty Waukee

  304 Maple Pointe, Winterset, IA 50273
• 

  

  /11

  $414,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  204 E Grade St, Winterset, IA 50273

  New Construction. Two story home with a cool layout. Home features three bedrooms, two and a half bathrooms, two car attached garage, and "safe room" which can be used as a storm shelter and/or safe. Buyer still has time to pick out flooring, and appliances.

  Chloe Marean Homefront Real Estate, LLC

  204 E Grade St, Winterset, IA 50273
• 

  

  /11

  $655,384

  • Land
  • 96 Acres
  • $6,819 per Acre

  00 Millstream Ave, Winterset, IA 50273

  Premium Row Crop Ground with Endless Potential | Madison County, IowaRepresenting 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 Clearfield silty clay

  Andrew Zellmer Peoples Company

  00 Millstream Ave, Winterset, IA 50273
• 

  

  /14

  $1,150,000

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

  00 Clark Tower Rd, Winterset, IA 50273

  Prime Rural Residential Developmental Land Offering | Just south of Winterset, IowaRepresenting 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 Residential—an increasingly difficult

  Andrew Zellmer Peoples Company

  00 Clark Tower Rd, Winterset, IA 50273
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /34

  $308,900

  • 3 Beds
  • 4 Baths
  • 1,694 Sq Ft

  604 W Jefferson St, Winterset, IA 50273

  This Gorgeous historical home is waiting for you on one of the prettiest streets in Winterset! This 3 bed, 2 full bath, 2 half bath has updates galore! The wrap around front porch welcomes you to the main floor and spacious living area and dining room with coffee bar. The back deck access gives you plenty of space to enjoy your morning coffee right off the kitchen with a powder room for your

  Rene Soldwisch Zealty Home Advisors

  604 W Jefferson 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /35

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,972 Sq Ft

  522 N 10th St, Winterset, IA 50273

  Double Lot Opportunity! So Much Potential!!Don't miss out on this spacious 3+ bedroom, 2-bathroom home situated on a desirable double corner lot! The flexible 4th room offers endless possibilities. perfect as a den, craft room, nursery, or even a small bedroom (yes, it has a closet!).Inside, you'll find gorgeous wall-to-wall hardwood floors, a bright eat-in kitchen, and a generous

  Kristen Stehli RE/MAX Precision

  522 N 10th St, Winterset, IA 50273
• 

  

  /14

  $240,000

  • 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
• 

  

  /31

  $315,000

  • 4 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  804 N 4th Ave, Winterset, IA 50273

  Welcome to a truly extraordinary home where timeless craftsmanship, modern luxury, and stunningnatural beauty come together in perfect harmony. Rarely does a property offer such a unique blend of old-world artisan detail and contemporary design, all set against the backdrop of gardens so exquisite! From the moment you arrive, the lush landscaping captures your attention, showcasing a level of

  Sarah Cowman Homefront Real Estate, LLC

  804 N 4th Ave, Winterset, IA 50273
• 

  

  /18

  $80,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  3028 Carver Rd, Winterset, IA 50273

  Unique opportunity to own an affordable acreage!! NO Covenants!! 2bed/1 bath with bonus loft on +\- half acre in Madison County! 1+ car detached garage. Fenced area for optional livestock or garden.

  Alyssa Tadlock Madison County Realty

  3028 Carver Rd, Winterset, IA 50273
• 

  

  /22

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  410 N 6th St, Winterset, IA 50273

  Pride of ownership in this spacious home! 3 bedrooms, 2 baths, over 2,000 sf finished space and a huge backyard. Adorable kitchen with stainless steel appliances. Refrigerator is less than 1 year old. Large dining area with sliding door that leads to the deck/backyard. Great set up for the primary bedroom with access to the bathroom/laundry room. All 3 bedrooms are on the 1st floor. The lower

  Jennifer Stover Madison County Realty

  410 N 6th St, 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
• 

  

  /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
• 

  

  /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
• 

  

  /28

  $550,000

  • 4 Beds
  • 3 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 lower level of the house also has 1 bedroom, bath, kitchen, fireplace. You could also rent out the LL of the house. Making total number of units available for rent: 6. The owners

  Jennifer Stover Madison County Realty

  715 N John Wayne Dr, Winterset, IA 50273

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