Newest Homes for Sale in Winterset, IA

• 

  

  

  /19

  $300,000

  • 4 Beds
  • 3 Baths
  • 1,087 Sq Ft

  301 N 15th Ave, Winterset, IA 50273

  Welcome to 301 N 15th Avenue, a well-maintained home ideally located in a quiet, established neighborhood on the north side of Winterset. This inviting property offers a functional layout with comfortable living spaces, making it a great fit for a variety of lifestyles. The home features a bright and welcoming interior with ample natural light throughout. The spacious kitchen provides convenient

  Kate Anderson RE/MAX Concepts

  301 N 15th Ave, Winterset, IA 50273
• Explore Winterset

• 

  

  

  /31

  $389,900

  • 5 Beds
  • 4 Baths
  • 2,600 Sq Ft

  223 W Lane St, Winterset, IA 50273

  Spacious 5-bedroom, 4-bath ranch situated on a desirable corner lot with a large yard built for both relaxation and recreation. Enjoy your own basketball court and patio—perfect for entertaining, family time, or unwinding after a long day. Inside, you’ll find a formal dining room ideal for hosting gatherings, along with the added benefit of new windows for improved comfort and efficiency. With

  Rachel Eller Summerset Realty

  223 W Lane St, Winterset, IA 50273
• 

  

  

  /17

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,270 Sq Ft

  1413 W Washington St, Winterset, IA 50273

  Beautifully maintained, this 4-bedroom ranch offers easy single-level living with an inviting open floor plan. A rare oversized 3-car garage with additional storage is a dream for car enthusiasts or hobbyists, and the deck off the kitchen provides the perfect backdrop for outdoor dining and entertaining!

  Sarah Cowman Homefront Real Estate, LLC

  1413 W Washington St, Winterset, IA 50273
• 

  

  /2

  $125,000

  • Land

  000 198th Ct, Winterset, IA 50273

  Want to build outside of town but don't like gravel? This lot is for you! Bring your own builder! Nestled just north of Winterset, this lot is in a very small development so only a few neighbors! Conveniently located just minutes from all that our amazing town has to offer! Schedule a time to view this property for yourself!

  Sarah Cowman Homefront Real Estate, LLC

  000 198th Ct, Winterset, IA 50273
• 

  

  

  /35

  $455,000

  • Land
  • 3 Acres
  • $151,667 per Acre

  2075 Hogback Bridge Rd, Winterset, IA 50273

  Acreages this close to the town of Winterset are extremely hard to find, but finding one engineered to this standard is nearly impossible. This expansive 2,568 sq. ft. homestead on 3 pristine acres features 3 bedrooms, 3 bathrooms, and a large kitchen designed with plenty of storage and a sprawling floor plan for the active country lifestyle. The home features spray foam insulation throughout the

  Ian Sparks Homefront Real Estate, LLC

  2075 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /35

  $340,000

  • 5 Beds
  • 2.5 Baths
  • 2,217 Sq Ft

  621 W Jefferson St, Winterset, IA 50273

  Step into timeless charm with this deceptively spacious 1903 home, perfectly situated on a corner lot along the picturesque, tree-lined W. Jefferson Street—just blocks from the square in Winterset. From the moment you arrive, the inviting front porch sets the tone for relaxed mornings, evening conversations, and a true sense of home. Inside, you’ll find the perfect blend of character and modern

  Jennifer Stover Madison County Realty

  621 W Jefferson St, Winterset, IA 50273
• 

  

  /28

  $455,000

  • 4 Beds
  • 3 Baths
  • 1,555 Sq Ft

  802 N 10th Ave, Winterset, IA 50273

  Easy living in this open floor plan ranch home. A large covered front porch greets you as you enter the foyer. There is a nice drop zone for coats and shoes. The living room is very spacious and has a stunning gas fireplace. The kitchen is bright and features a breakfast bar and nice sized pantry. The dining is off the kitchen. The primary bedroom is large and has a huge bathroom with tile

  Sarah Cowman Homefront Real Estate, LLC

  802 N 10th Ave, Winterset, IA 50273
• 

  

  /27

  $330,000

  • 4 Beds
  • 3 Baths
  • 1,990 Sq Ft

  1706 W Summit St, Winterset, IA 50273

  This two-story brick home, built in 1923, has all of the character and charm that goes with a 1920s house. Original built-ins, woodwork, hardwood floors and glass doorknobs still remain in the house. With 1990 sf, 4 bedroom and 3 baths, there is plenty of room for everyone. The first floor features a large family room with beautiful built-ins surrounding the fireplace. French doors from the

  Larry Corkrean Madison County Realty

  1706 W Summit St, Winterset, IA 50273
• 

  

  /35

  $650,000

  • Land
  • 4.6 Acres
  • $141,304 per Acre

  2223 Holliwell Valley Ct, Winterset, IA 50273

  This exceptional walkout ranch presents an extraordinary opportunity for those seeking space, comfort, and country charm. Situated on over four and a half acres of stunning Iowa countryside, the home boasts more than three thousand square feet of beautifully finished living space with four bedrooms and four bathrooms. The open floorplan and wall of windows make the main level light, bright and

  Melissa Hatchitt Zealty Home Advisors

  2223 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /23

  $299,900

  • 3 Beds
  • 2 Baths
  • 838 Sq Ft

  521 W Hutchings St, Winterset, IA 50273

  Walk out ranch home with huge yard! This is a must see property! You will appreciate the updated inside featuring a bright eat in kitchen (the kitchen appliances are all included!). The living room has a cozy electric fireplace and nice big windows overlooking the huge back yard. There are 2 bedrooms and a full bath upstairs. The basement is a bright sunny walk out with a large family room,

  Sarah Cowman Homefront Real Estate, LLC

  521 W Hutchings St, Winterset, IA 50273
• 

  

  /17

  $165,000

  • 2 Beds
  • 1 Bath
  • 1,286 Sq Ft

  415 E Buchanan St, Winterset, IA 50273

  Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1,286 sq ft, this home features a well-designed main-level layout with comfortable living space and a first-floor bedroom. Enjoy the added charm of a 3-season room perfect for relaxing or entertaining. Equipped with natural gas heating, city water and sewer, and included kitchen appliances for added

  Anagha Berodia Iowa Realty Waukee

  415 E Buchanan St, Winterset, IA 50273
• 

  

  /25

  $249,000

  • 3 Beds
  • 1 Bath
  • 962 Sq Ft

  710 N 3rd Ave, Winterset, IA 50273

  Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home has fenced yard, great fire pit area for outdoor entertaining, contained decorative garden/flower beds and a row of new trees. Other new yard features include landscaping rock and creative oval garden landscaping mound. Updates include fully encapsulated deep crawl space with warranty and new sump pump.

  

  Toni Tindle

  Covered Bridge Realty

  (515) 949-4406

  710 N 3rd Ave, Winterset, IA 50273
• 

  

  /34

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,574 Sq Ft

  222 Oak Tree Dr, Winterset, IA 50273

  Well cared for one-owner home featuring 3 bedrooms, 3 bathrooms with high 9 ft ceilings that create a bright, open feel throughout the main living area. The thoughtfully designed floor plan includes a functional kitchen, and a primary suite with a private bath. Enjoy the 4-season porch, perfect for relaxing or entertaining year round. The basement is ready to finish, already drywalled just

  Amber Stemler Iowa Realty Mills Crossing

  222 Oak Tree Dr, Winterset, IA 50273
• 

  

  /14

  $317,250

  • Land
  • 13.5 Acres
  • $23,500 per Acre

  2571 250th Ln, Winterset, IA 50273

  A stunning piece of ground at the end of a dead end road! Aproximately 13.5 acres to be surveyed off. This would make a beautiful executive building lot, or a fun place to go camp on the weekends! The pond is stocked for all of you who like to fish. There will be some restrctive covenants but horses and some farm animals will be allowed. Final price will be per acre based on the survey. Come

  Sarah Cowman Homefront Real Estate, LLC

  2571 250th Ln, Winterset, IA 50273
• 

  

  /23

  $169,900

  • 3 Beds
  • 1.5 Baths
  • 1,306 Sq Ft

  604 E Jefferson St, Winterset, IA 50273

  Story and 1/2, 3BR 1.5 bath affordable home located in Winterset. Large eat-in kitchen, huge living room with staircase on one end. Staircase leads to 3 bedrooms on the second floor with 1/2 bath. Main floor laundry. Bath on second floor can be entered from the hall or access through SW bedroom. Enclosed rear porch off kitchen attached one car garage with entrance on both ends totals 544 sq feet.

  

  Toni Tindle

  Covered Bridge Realty

  (515) 361-3110

  604 E Jefferson St, Winterset, IA 50273
• 

  /2

  $382,500

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

  309 Maple Pointe, Winterset, IA 50273

  Stryker Ranch New Construction with oversized 3 car garage. Front porch with 2 stone base posts. 9' ceilings throughout main floor. Open stairs to basement. Granite or quartz countertops 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.

  Robert D. Weeks Iowa Realty Waukee

  309 Maple Pointe, Winterset, IA 50273
• 

  

  /34

  $1,225,000

  • 5 Beds
  • 5 Baths
  • 2,434 Sq Ft

  2188 114th Ct, Winterset, IA 50072

  Welcome to modern acreage living at its finest! Set on 5.32 picturesque acres in gorgeous Madison County and located in the highly desirable Adel school district, this stunning home offers the perfect blend of peaceful country living with everyday convenience. Just 13 minutes from Grand Prairie Parkway, you’ll enjoy an easy drive on all blacktop roads—no gravel! Inside, discover 4,593 sq ft of

  Julie Baudler RE/MAX Concepts

  2188 114th Ct, Winterset, IA 50072
• 

  

  /35

  $1,250,000

  • Land
  • 57.36 Acres
  • $21,792 per Acre

  1826 Green Ln, Winterset, IA 50273

  57.36 Acres with Log Home, Livestock Facilities & Equipment – Earlham School District Located just 3 miles north of Highway 92 and approximately 2 miles east of Earlham Road, this 57.36 gross acre property offers a great combination of rural living, pasture ground, and functional farm improvements. The property features a 2-story log cabin style home built in 1996 offering approximately 2,282

  Shane Spyksma Kiloterra

  1826 Green Ln, Winterset, IA 50273
• 

  

  /35

  $899,900

  • Land
  • 19.93 Acres
  • $45,153 per Acre

  1516 Roseman Bridge Rd, Winterset, IA 50273

  Welcome to your own private retreat on 20 beautiful acres near Winterset. This thoughtfully updated 3-bedroom, 4-bath, over 3100 sqft ranch home offers the perfect balance of comfort, space, and peaceful country living. Inside, you'll find inviting living spaces including a dedicated home office and a relaxing four-season sunroom, perfect for enjoying the surrounding views year-round. Step

  Lauren Moore Agency Iowa

  1516 Roseman Bridge Rd, Winterset, IA 50273
• 

  

  /27

  $230,000

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

  619 N 10th St, Winterset, IA 50273

  Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006 lift with a full poured-concrete basement. The main level offers a bright eat-in kitchen with all appliances included, whih opens to a deck - perfect for grilling. Off the kitchen is a full bathroom with laundry! There is a main floor bedroom that could also be used as a living room or flex space. Upstairs

  Sarah Cowman Homefront Real Estate, LLC

  619 N 10th St, Winterset, IA 50273
• 

  

  /34

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  114 N 8th Ave, Winterset, IA 50273

  Completely updated 3-bedroom, 2-bath home blending timeless character with extensive upgrades! Original woodwork, detailed craftsmanship, and charming built-ins pair beautifully with newer hardwood floors (2022), granite countertops, stainless steel appliances, updated cabinetry, and tile flooring. The main level features a spacious living room with built-ins, formal dining room with classic

  Kari Stone RE/MAX Precision

  114 N 8th Ave, Winterset, IA 50273
• 

  

  /13

  $309,990

  • 4 Beds
  • 3 Baths
  • 1,464 Sq Ft

  623 W Green St, Winterset, IA 50273

  Charming, solid, and beautifully cared for -this all-brick ranch in historic Madison County is the one you've been waiting for. With standout curb appeal and numerous updates throughout, this home blends classic construction with modern comfort. The main level offers three comfortable bedrooms, while the partially finished lower level provides a full additional bedroom plus a fifth non-conforming

  Markjon Trierweiler RE/MAX Precision

  623 W Green St, Winterset, IA 50273
• 

  

  /34

  $750,000

  • 4 Beds
  • 3.5 Baths
  • 2,088 Sq Ft

  1685 McBride Ridge Ct, Winterset, IA 50273

  The perfect balance of executive luxury and rural serenity in this stunning 4-bedroom, 3.5-bathroom partial brick walkout ranch, situated on 4.56 scenic acres in Madison Co. Located on a private drive just off Cumming Highway, this property offers a peaceful country lifestyle on hard surface for an easy commute to DSM or Winterset. The home features 2x6 construction, rich woodwork, granite

  Sean Asada RE/MAX Real Estate Center

  1685 McBride Ridge Ct, Winterset, IA 50273
• 

  

  /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
• 

  

  /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
• 

  

  /33

  $478,750

  • Land
  • 5 Acres
  • $95,750 per Acre

  2980 Clark Tower Rd, Winterset, IA 50273

  Located in scenic Madison County this newly built home and buildings offers peace and quiet with close commute to Winterset and West Des Moines. Located on hard surface road 8.5 miles south of Winterset. The home offers 2 bedrooms and 2 baths. The main floor offers an open concept with a nice main living and dining area. The upstairs offers the opportunity to expand to increase finished square

  Luke Skinner Iowa Land Company

  2980 Clark Tower Rd, Winterset, IA 50273
• 

  

  /7

  $250,000

  • Land
  • 5.1 Acres
  • $49,020 per Acre

  2269 205th Ln, 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

  2269 205th Ln, Winterset, IA 50273
• 

  

  /7

  $160,000

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

  2259 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

  2259 Cedar Bridge Rd, Winterset, IA 50273
• 

  

  /32

  $360,000

  • Land
  • 8 Acres
  • $45,000 per Acre

  2817 Carver Rd, Winterset, IA 50273

  A bit of elbow grease and this sweet ranch home could be your dream acreage! With a fabulous layout, 3 bedrooms, 2 and 1/2 baths, large kitchen and dining area, huge living room and the full basement is a blank slate. The most beautiful setting on a hill overlooking a pond and surrounded by nature! There are no covenants so you can have your 4-H Animals or horses or whatever your heart desires.

  Sarah Cowman Homefront Real Estate, LLC

  2817 Carver Rd, Winterset, IA 50273
• 

  /2

  $395,000

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

  2210 Ash Tree Dr, Winterset, IA 50273

  Jackson Walkout Ranch Plan 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 a large walk-in pantry and stainless-steel appliances. White painted maple cabinets throughout. Luxury vinyl flooring. 60 inch gas fireplace. Master bath with raised vanity and

  Robert D. Weeks Iowa Realty Waukee

  2210 Ash Tree Dr, Winterset, IA 50273
• 

  

  /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
• 

  

  /21

  $249,900

  • 3 Beds
  • 2.5 Baths
  • 1,006 Sq Ft

  113 S 3rd St, Winterset, IA 50273

  Move-in ready and totally remodeled 3-bed 2.5-bath ranch! Everything you need is on the main level. This home has been thoughtfully renovated, utilizing every square inch. Walk in, and you will appreciate the large entry way ready for your locker system or bench area. The living room is bright and spacious and is open to the kitchen. The kitchen has nice counter and cabinet space with a pantry

  Sarah Cowman Homefront Real Estate, LLC

  113 S 3rd St, Winterset, IA 50273
• 

  

  /18

  $223,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1221 W Washington St, Winterset, IA 50273

  This super sweet ranch home makes a great starter home. The covered front porch is a great way to relax on the hot summer days. The first floor features a spacious kitchen, comfortable living room, 2 generous sized bedrooms and an updated full bath. The full basement is open and ready finish. The attached garage is heated and has access to the fenced backyard. The backyard features a large patio

  Jennifer Stover Madison County Realty

  1221 W Washington St, Winterset, IA 50273
• 

  

  /35

  $999,000

  • Land
  • 19.5 Acres
  • $51,231 per Acre

  2230 260th St, Winterset, IA 50273

  Set on 19.5 acres just outside Winterset, this property offers a rare combination of scale, function and lifestyle. With nearly 4,800 finished square feet, geothermal heating and cooling, a 36x54 outbuilding and approximately 13 acres of productive row crop, this is a well-rounded acreage package that is difficult to replicate.The 1.5-story home features a warm, timeless interior with vaulted

  Julie Egli RE/MAX Precision

  2230 260th St, Winterset, IA 50273
• 

  

  /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
• 

  

  /23

  $290,000

  • 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
• 

  

  /11

  $372,750

  • Land
  • 18.64 Acres
  • $19,997 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Premium Executive Building Lot on Pavement | Just South of Winterset, Iowa Peoples Company is proud to represent the Utsler Family Trust in the sale of an exceptional 18.64-acre executive building lot located just 3 miles south of Winterset, Iowa, with direct access off paved Clark Tower Road. This recently surveyed property offers the rare combination of privacy, premium views, utilities at

  Andrew Zellmer Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /10

  $52,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 109, Winterset, IA 50273

  This spacious 3 bedroom, 2 bathroom home features a primary bedroom with its own private en suite bathroom for added comfort. Enjoy freshly painted interiors and brand new carpet in the bedrooms, giving the home a clean and inviting feel. There's a fireplace in the living room for cozy winter night. Call today for a tour!

  Lea McFadden Covered Bridges MHP

  1624 W Summit St Unit 109, Winterset, IA 50273
• 

  

  /7

  $36,900

  • 2 Beds
  • 1 Bath

  1624 W Summit St Unit 134, Winterset, IA 50273

  This 2 bedroom, 1 bathroom home is a comfy, with an eat in kitchen with an island. This home has a NEW roof, plenty of windows, with newer blinds, that provides the home with natural light. The living room is very spacious in this home. The bathroom is conveniently located between both bedrooms for great efficiency.

  Lea McFadden Covered Bridges MHP

  1624 W Summit St Unit 134, Winterset, IA 50273
• 

  

  /30

  $449,000

  • Land
  • 9.8 Acres
  • $45,816 per Acre

  1024 W Summit St, Winterset, IA 50273

  In town acreage opportunity. 3-bedroom, 1-bath home on 9.88 m/l acres located just outside the Winterset city limits. The home offers 2,286 sq ft of living area with main-level and upper-level bedrooms, and a partial basement. A detached 1-car garage and a 1,620 sq ft pole building provides additional storage and workspace. The acreage features open ground with level to rolling terrain and treed

  Jerold Steenhoek Iowa Realty Waukee

  1024 W Summit St, Winterset, IA 50273

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