Newest Homes for Sale in Winterset, IA

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  /35

  $1,195,000

  • Land
  • 36.34 Acres
  • $32,884 per Acre

  1524 260th St, Winterset, IA 50273

  DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 36ac in beautiful MADISON COUNTY. As soon as you walk in the door you will see what makes this home stand out. The CRAFTSMANSHIP is amazing, from the CUSTOM CABINETS and DOORS and CUSTOM COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this

  Betsy Breeding Realty ONE Group Impact

  1524 260th St, Winterset, IA 50273
• Explore Winterset

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  /2

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  510 E Court Ave, Winterset, IA 50273

  3-bedroom ranch with a 2-car detached garage offering tons of potential! Recent updates include a new roof, exterior paint, boiler, and garage door. Home is in need of TLC and cosmetic updates but provides a great opportunity for buyers looking to add their own touch. Solid bones with plenty of possibilities! photos coming soon

  Rachel Eller Summerset Realty

  510 E Court Ave, Winterset, IA 50273
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  /35

  $650,000

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

  2223 Holliwell Valley Ct, Winterset, IA 50273

  Perfect acreage alert! This exceptional walkout ranch is ready for new owners to move in and enjoy the breathtaking sunsets over the valley. All of the big ticket items have been upgraded: roof, HVAC, windows, deck - radon mitigation installed - nothing to worry about here! Situated on over 4.5 acres of stunning Iowa countryside, the home features more than 3,000 square feet of beautifully

  Melissa Hatchitt Realty ONE Group Impact

  2223 Holliwell Valley Ct, Winterset, IA 50273
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  /26

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  406 N 7th St, Winterset, IA 50273

  This home was a complete remodel down to the studs in 2024, with New Electric, Plumbing, Drywall, Doors, Windows, Trim...Everything! This property has a spacious kitchen, 2 bedrooms, 2 baths and a large, flat backyard! There are all new windows with nice natural light. Off of the living room is a back deck overlooking the backyard. The eat in kitchen is very spacious with nice cabinet space,

  Dakoda Overbeck Iowa Realty Waukee

  406 N 7th St, Winterset, IA 50273
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  /28

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft

  1514 MacKensie Cir, Winterset, IA 50273

  Spacious 2 story home in the Birchwood development. 3 bedrooms, 2.5 baths, 1669sf. Modern open floor plan. Large kitchen and dining area. Sliding door from dining area leads to the deck. Just off the kitchen is a home office/formal dining room. The 2nd floor features 3 generous bedroom, 2 baths, and laundry room. The lower level is ready for the new homeowners to finish for even more living

  Jennifer Stover Madison County Realty

  1514 MacKensie Cir, Winterset, IA 50273
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  /31

  $400,000

  • Land
  • 3.82 Acres
  • $104,712 per Acre

  1509 State 92 Hwy, Winterset, IA 50273

  Step back in time and imagine the possibilities with this classic farmhouse nestled on 3.82 scenic acres surrounded by mature timber and peaceful countryside views. Built in 1925, this 2-story home offers 1,680 square feet filled with original character and timeless charm. Inside, you’ll find 4 bedrooms, a home office, beautiful original trim, stunning French doors in the dining room and living

  Jennifer Stover Madison County Realty

  1509 State 92 Hwy, Winterset, IA 50273
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  /27

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  511 W Washington St, Winterset, IA 50273

  Welcoming 1 1⁄2 story brick home on Winterset West side. Recent remodel, galley kitchen, main floor bedroom and full bath. Living room open to dining area. Handy drop zone near rear door from detached garage. Full unfinished basement with included washer and dryer and 1⁄2 bath with a bonus laundry sink and workshop area. Three bedrooms on the second level hardwood floors and full bath upstairs.

  

  Toni Tindle

  Covered Bridge Realty

  (515) 800-4015

  511 W Washington St, Winterset, IA 50273
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  /34

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft

  524 W Benton St, Winterset, IA 50273

  Full of cozy charm and timeless character, this delightful Cape Cod-style home offers 1,705 square feet of warm and inviting living space. Built in 1964, the home features 3 bedrooms — including a convenient main-floor bedroom and bath — designed for comfortable everyday living. 2 living rooms - one with oversized picture windows to take in the natural light and the other room features a

  Jennifer Stover Madison County Realty

  524 W Benton St, Winterset, IA 50273
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  /34

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  302 W Court Ave, Winterset, IA 50273

  Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideally located on historic Court Ave just one block from the town square. Offering 2,396 square feet, 3 bedrooms, and 2.5 baths, this beautifully maintained home blends original character with modern functionality in all the right ways. The showstopping custom-designed kitchen is truly the heart of the home,

  Jennifer Stover Madison County Realty

  302 W Court Ave, Winterset, IA 50273
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  /35

  $335,000

  • 4 Beds
  • 1,470 Sq Ft

  1405 W Jefferson St, Winterset, IA 50273

  Welcome to this well-maintained 4 bedroom, 3 bathroom home offering just under 1,500 square feet of comfortable living space in one of Central Iowa?s most charming communities. This home features a functional layout with spacious living areas, abundant natural light, and plenty of room for both everyday living and entertaining.The main living space offers a warm and inviting feel with an open

  Matt Law RE/MAX Precision

  1405 W Jefferson St, Winterset, IA 50273
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  /33

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  209 W Jefferson St Unit 17, Winterset, IA 50273

  Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

  Kent Brant Exit Country Realty

  209 W Jefferson St Unit 17, Winterset, IA 50273
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  /35

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  209 W Jefferson St Unit 23, Winterset, IA 50273

  Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

  Kent Brant Exit Country Realty

  209 W Jefferson St Unit 23, Winterset, IA 50273
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  /11

  $350,000

  • Land
  • 18.64 Acres
  • $18,777 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Luxury Executive Acreage on Pavement | 18.64 Acres Just South of Winterset, Iowa Presenting a premier 18.64-acre executive acreage opportunity located just three miles south of Winterset on paved Clark Tower Road. Opportunities of this caliber in Madison County are increasingly difficult to find, offering the perfect combination of scenic beauty, privacy, usable land, and convenient access to the

  Andrew Zellmer Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
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  /17

  $180,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  402 N 9th St, Winterset, IA 50273

  Well maintained ranch on a corner lot. Open floor plan with 1,152 sf, 3 bedroom, 1 full bath. 1st floor laundry room. Spacious kitchen and dining area. Gas fireplace in living room. Large covered patio space - perfect for grilling all year and relaxing in the summer. Parking pad for 2 cars. Newer roof.

  Randall Henry Madison County Realty

  402 N 9th St, Winterset, IA 50273
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  /2

  $130,000

  • Land
  • 39,204 Sq Ft
  • $144,444 per Acre

  Lot 1 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to build upon in Spring 2025, Street will be in Fall 2024. All utilities to the lots. Great location on north side of Winterset w/ easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 1 N 4th Ave, Winterset, IA 50273
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  /2

  $185,000

  • Land
  • 1.14 Acres
  • $161,996 per Acre

  Lot 4 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road will paved in Fall 2025. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 4 N 4th Ave, Winterset, IA 50273
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  /2

  $125,000

  • Land
  • 31,798 Sq Ft
  • $171,233 per Acre

  Lot 3 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to build upon in Spring 2025, Road is being paved in Fall 2024. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 3 N 4th Ave, Winterset, IA 50273
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  /2

  $395,000

  • Land
  • 3 Acres
  • $131,667 per Acre

  Lot 5 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road pave in Fall 2024. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property

  Peter Corkrean Madison County Realty

  Lot 5 N 4th Ave, Winterset, IA 50273
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  /34

  $595,000

  • 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
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  /27

  $269,900

  • 3 Beds
  • 1 Bath
  • 1,859 Sq Ft

  319 S 7th Ave, Winterset, IA 50273

  WELCOME HOME to this beautiful 3 bed/1 bath home on .32 ac lot. You will LOVE walking into the large living room, with plenty of NATURAL LIGHT and nice sized dining area. The kitchen has plenty of COUNTER SPACE and also a nice sized ISLAND. Off of the kitchen is the large 4 SEASON PORCH/family room (12'x33') with plenty of windows and natural light. The perfect area for ENTERTAINING! Two bedrooms

  Betsy Breeding Realty ONE Group Impact

  319 S 7th Ave, Winterset, IA 50273
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  /32

  $140,000

  • 2 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  906 S 4th Ave, Winterset, IA 50273

  Opportunity awaits in this 1.5-story home located at 906 S 4th Ave in Winterset, right next to the high school. This property offers a functional layout with a main floor bedroom, 1.5 baths, and convenient main floor laundry. Upstairs you'll find an additional bedroom, a full bathroom, and a non-conforming bedroom--providing flexible space for a variety of needs. Outside features include a 2-car

  Dezaray Buchwald iHome Realty

  906 S 4th Ave, Winterset, IA 50273
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  /7

  $160,000

  • Land
  • 3.27 Acres
  • $48,930 per Acre

  2323 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

  2323 Cedar Bridge Rd, Winterset, IA 50273
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  /24

  $262,500

  • 4 Beds
  • 2 Baths
  • 1,482 Sq Ft

  610 W Washington St, Winterset, IA 50273

  Charming Cape Cod with space, style, and a location you’ll love. This well-maintained 1.5-story home offers 1,482 square feet of inviting living space, featuring 4 bedrooms and 2 bathrooms designed for comfort and flexibility. Step inside to find a home that has been exceptionally cared for—clean, bright, and move-in ready. The layout offers a cozy yet functional flow, with a finished lower level

  Larry Corkrean Madison County Realty

  610 W Washington St, Winterset, IA 50273
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  /29

  $260,000

  $10K PRICE DROP

  • Land
  • 10.23 Acres
  • $25,415 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Have you been looking for the perfect country spot to build your dream home? This 10 acre lot has all of the infrastructure already in place. It is build-ready! $50,000 has been invested in the property for a building pad, water and electric brought from the road to the build site, new driveway, etc. A future barndominium or walkout home will enjoy rolling countryside views for miles.

  Jeffrey Longman RE/MAX Precision

  2212 Deer Run Ave, Winterset, IA 50273
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  /35

  $339,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  2197 175th Ct, Winterset, IA 50273

  Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all

  Ambria Vogt RE/MAX Precision

  2197 175th Ct, Winterset, IA 50273
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  /35

  $384,900

  $14K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,720 Sq Ft

  704 N 14th Ave, Winterset, IA 50273

  Tucked at the end of a quiet street, this 4-bedroom home sits on an oversized lot in a welcoming neighborhood. You'll love the fully fenced yard, wooden fencing, and large deck, perfect for enjoying the outdoors.Inside, the main level offers a functional layout with a drop zone at the front entry, a dedicated office/study, and a spacious living area with a cozy fireplace. The kitchen features

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  704 N 14th Ave, Winterset, IA 50273
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  /34

  $579,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  719 E Washington St, Winterset, IA 50273

  Discover the ultimate "wow factor" in this stunning Winterset property, truly like anything else. It’s been completely rebuilt to marry historic soul with modern luxury. This isn't just a renovation; it’s a turnkey masterpiece designed for entertaining and everyday living; featuring a main-level primary retreat bathed in incredible natural sunlight throughout the home. It includes 3 bedrooms +

  Sarah Cowman Homefront Real Estate, LLC

  719 E Washington St, Winterset, IA 50273
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  /35

  $339,900

  $10K 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
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  /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
• 

  

  /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
• 

  

  /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

  $159,000

  $6K PRICE DROP

  • 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
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  /27

  $234,900

  $20K PRICE DROP

  • 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
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  /34

  $389,900

  $10K PRICE DROP

  • 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
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  /14

  $285,000

  $32K PRICE DROP

  • Land
  • 13.5 Acres
  • $21,111 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
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  /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

  $1,187,500

  $63K PRICE DROP

  • Land
  • 57.36 Acres
  • $20,703 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
• 

  

  /27

  $225,000

  $15K PRICE DROP

  • 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
• 

  

  /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

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