Newest Homes for Sale in Winterset, IA

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  /35

  $395,000

  • 4 Beds
  • 3 Baths
  • 2,576 Sq Ft

  1473 280th St, Winterset, IA 50273

  Sitting on 4.96± acres in the countryside of Madison County, this Amish-built home offers the perfect opportunity to create your dream rural retreat. Built in 2018, the 2,576 sq. ft. home features 4 bedrooms, 3 bathrooms, vaulted ceilings, and a unique natural tree centerpiece. The home offers a durable metal exterior and roof, spray-foam insulation, rural water, plumbing, propane, hot water

  Will Cooper Midwest Land Group LLC

  1473 280th St, Winterset, IA 50273
• Explore Winterset

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  /34

  $565,000

  • 4 Beds
  • 3 Baths
  • 1,506 Sq Ft

  5219 Cherrywood Ln, Winterset, IA 50273

  Stunning 4 bed (5 non-conforming) 3 bath home nestled on 2.24 acres! Walking in you are instantly drawn to over-sized windows showcasing a beautiful backyard. Home features 2x6 exterior walls & 9' ceilings. Kitchen has 11' long single piece quartz island w/ double-sided cabinets that demands its own zip code. A large walk-in pantry & custom built wood shelving and all appliances included complete

  Jonathan Lee RE/MAX Precision

  5219 Cherrywood Ln, Winterset, IA 50273
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  /34

  $239,000

  • 3 Beds
  • 2.5 Baths
  • 1,246 Sq Ft

  207 E Buchanan St, Winterset, IA 50273

  Now this is a home you'll want to show off! A historic Frame House in the heart of Winterset, fully renovated & remarkably designed. Huge curb appeal, mature trees, brand new front deck. Inside is a beautiful entry that leads to a stunning, expansive living room with original shiplap ceiling, tons of natural light. Gorgeous, grand dining room. The kitchen meets your needs & has tons of style. New

  Alison Frank Platinum Realty LLC

  207 E Buchanan St, Winterset, IA 50273
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  /33

  $235,000

  • 5 Beds
  • 2 Baths
  • 1,701 Sq Ft

  204 S 8th Ave, Winterset, IA 50273

  Welcome home to this charming two-story home situated on a spacious corner lot! Offering 5 bedrooms and 2 bathrooms, there's plenty of room to spread out and make it your own. Inside, you'll find a comfortable blend of carpeting and laminate flooring that creates a warm and welcoming feel throughout. The attached garage offers space for two vehicles plus a dedicated workshop area, making it ideal

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  204 S 8th Ave, Winterset, IA 50273
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  /26

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  420 W Mills St, Winterset, IA 50273

  This well-maintained home offers a ton of space and a sprawling floor plan that sets it apart from your traditional split-level layout. A major highlight is the large, completely finished master suite situated privately above the garage. In total, the home features 4 bedrooms, 2 full bathrooms, and one half bathroom, along with its own dedicated laundry room. The kitchen includes a convenient bar

  Ian Sparks Homefront Real Estate, LLC

  420 W Mills St, Winterset, IA 50273
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  /35

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  2381 Adair Madison Ave, Winterset, IA 50273

  Discover the perfect blend of country living, outdoor recreation, and modern updates with this exceptional 10-acre hobby farm, located just one mile off Highway 92. Step inside the beautifully updated 3-bedroom, 1-bathroom home featuring a comfortable, flowing floor plan. The heart of the home is a large country kitchen with abundant cabinet space and room for a dining table, which seamlessly

  Ian Sparks Homefront Real Estate, LLC

  2381 Adair Madison Ave, Winterset, IA 50273
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  /30

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  423 E Jefferson St, Winterset, IA 50273

  Welcome home to this adorable 3-bedroom, 2-bath Arts & Crafts bungalow built in 1920, offering 1,913 sq ft of timeless charm and thoughtful updates. From the inviting covered porch and fenced front yard to the beautiful original details throughout, this home perfectly blends historic character with today’s conveniences. Step inside to find a warm and welcoming family room featuring wood beams, a

  Jennifer Stover Madison County Realty

  423 E Jefferson St, Winterset, IA 50273
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  /9

  $44,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 106, Winterset, IA 50273

  Discover affordable small-town living at its finest in this beautiful 3-bedroom, 2-bathroom home nestled in Winterset's peaceful Covered Bridges community! Step inside to find an impressively spacious living room and a large, welcoming kitchen perfect for family gatherings or entertaining friends. Offering unbeatable value with LVP throughout, Carpet in the bedrooms, freshly painted, steel

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 106, Winterset, IA 50273
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  /35

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  3035 Clark Tower Rd, Winterset, IA 50273

  Rare opportunity to own a beautifully improved 24+/- acre pasture and timber farm less than 9 miles from Winterset on pavement. Built in 2023, the ranch home offers 5 bedrooms, 3 bathrooms, an additional non-conforming bedroom, 2,800 finished square feet, and an unfinished 2,800-square-foot basement ready for your finishing touches. The attached 2,685-square-foot, 3-door insulated garage features

  Aaron Creger Midwest Land Group LLC

  3035 Clark Tower Rd, Winterset, IA 50273
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  /35

  $949,900

  • 3 Beds
  • 2.5 Baths
  • 3,210 Sq Ft

  1524 260th St, Winterset, IA 50273

  DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. The CRAFTSMANSHIP of this home is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The LARGE GRANITE BAR has a built-in beverage frig and seating for 8.

  Betsy Breeding Realty ONE Group Impact

  1524 260th St, Winterset, IA 50273
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  /34

  $1

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  00 235th St, Winterset, IA 50273

  Madison County, Iowa Land Auction! Presenting the sale of 75.33 surveyed acres m/l of premium recreational land located just southwest of Winterset, Iowa, in Madison County. This unique offering presents an excellent opportunity to purchase quality recreational property, attractive building sites, and a rural acreage in one of Iowa's most desirable counties. The property will be offered in three

  Daran Becker Peoples Company

  00 235th St, Winterset, IA 50273
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  /32

  $270,000

  • 4 Beds
  • 2 Baths
  • 866 Sq Ft

  715 N 3rd Ave, Winterset, IA 50273

  ** MOVE IN READY WITH ALL THE UPDATES ** This 4 bed 2 bath has been thoughtfully and skillfully updated and is ready for its new owners! Improvements include: All new interior paint. New/updated trim. All new Flooring. New lighting. New windows in 2025. Interior doors summer 2025. New siding approx 15 years ago with new paint summer 2025. New roof/sofit/facia approx 10 years. Furnace 3 years.

  Alyssa Tadlock Madison County Realty

  715 N 3rd Ave, Winterset, IA 50273
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  /7

  $165,000

  • Land
  • 7.68 Acres
  • $21,484 per Acre

  001 Rolling Green Ave, Winterset, IA 50273

  Build your dream home on 7.68 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM.

  Jodi Broadbent Realty ONE Group Impact

  001 Rolling Green Ave, Winterset, IA 50273
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  /7

  $140,000

  • Land
  • 5.36 Acres
  • $26,119 per Acre

  002 220th St, Winterset, IA 50273

  Build your dream home on 5.36 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM

  Jodi Broadbent Realty ONE Group Impact

  002 220th St, Winterset, IA 50273
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  /29

  $190,000

  • 3 Beds
  • 1 Bath
  • 1,926 Sq Ft

  415 N 1st Ave, Winterset, IA 50273

  Just blocks from Winterset’s historic square, this 1.5-story home blends charm with everyday function. A wraparound porch (swing included) sets the tone before you even walk in. Inside, a bright living room with a cozy fireplace opens into an eat-in kitchen with white cabinetry, stainless appliances, and a walk-in pantry. All three bedrooms sit on the main level, along with a full bath and

  

  Darson Grantham

  Keller Williams Realty GDM

  415 N 1st Ave, Winterset, IA 50273
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  /31

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  215 E Filmore St, Winterset, IA 50273

  Just listed: Winterset modestly priced ranch-style home.This property features two bedrooms, one full bathroom, and a partial bath located off the laundry room. The home offers easy entry through an enclosed front porch with a closet.The interior includes a large open kitchen and dining area. All kitchen appliances are included. For outdoor living and dining, sliders from the kitchen lead

  

  Toni Tindle

  Covered Bridge Realty

  215 E Filmore St, Winterset, IA 50273
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  /35

  $365,000

  • 4 Beds
  • 3 Baths
  • 1,524 Sq Ft

  1405 W Court Ave, Winterset, IA 50273

  Step inside and you'll be welcomed by a spacious entry that opens into the vaulted living room, where a cozy fireplace creates the perfect gathering space. This well-maintained ranch offers over 2,500 finished square feet, 4 bedrooms, and 3 bathrooms. The spacious kitchen features maple cabinetry, newer granite countertops, updated appliances, and large windows that showcase views of the

  Lauren Moore Agency Iowa

  1405 W Court Ave, Winterset, IA 50273
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  /29

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,476 Sq Ft

  519 W Filmore St, Winterset, IA 50273

  Old-world charm meets modern living in this beautifully maintained and renovated two story home, situated on a corner lot with landscaped grounds. Rich original woodwork, abundant natural light, and timeless character create a warm and inviting atmosphere throughout.The fully renovated kitchen and bathroom blend classic style with modern luxury, featuring custom cabinetry, premium Café

  Kurt Clements ListWithFreedom.com Inc

  519 W Filmore St, Winterset, IA 50273
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  /35

  $969,000

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft

  2318 Saint Charles Rd, Winterset, IA 50273

  Escape to your own peaceful slice of heaven with this stunning acreage offering over 45 scenic acres of rolling countryside, abundant wildlife, and endless possibilities. Approximately 18 acres are enrolled in a tax-deferred forestry program, while additional acreage provides excellent hay ground potential and beautiful pasture areas ideal for horses or hobby farming. A large outbuilding offers

  Helen Turner Iowa Realty Mills Crossing

  2318 Saint Charles Rd, Winterset, IA 50273
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  /64

  $949,900

  $245K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,210 Sq Ft

  1524 260th St, Winterset, IA 50273

  DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac 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, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The

  Betsy Breeding Realty ONE Group Impact

  1524 260th St, Winterset, IA 50273
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  /28

  $349,900

  $15K PRICE DROP

  • 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

  $370,000

  $30K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  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

  511 W Washington St, Winterset, IA 50273
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  /25

  $414,900

  $15K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,077 Sq Ft

  2607 Quail Ridge Trail, Winterset, IA 50273

  Set on 3 peaceful acres in Madison County, this charming 1.5-story farmhouse offers the perfect blend of country character, privacy and everyday function. With 2,077 square feet, the home features a warm farmhouse style throughout, including a farmhouse kitchen, inviting living spaces, 2 bathrooms, one bedroom on the main level, and three additional bedrooms upstairs.The sunroom overlooks the

  Julie Egli RE/MAX Precision

  2607 Quail Ridge Trail, Winterset, IA 50273
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  /7

  $45,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 122, Winterset, IA 50273

  Welcome home to this refreshed 3 bedroom, 2 bathroom home! Fresh paint throughout gives the home a clean, modern feel while the spacious layout offers comfort and functionality. The primary bedroom features its own private en suite bathroom, creating the perfect retreat at the end of the day. Cozy up by the fireplace in the living room and enjoy the inviting atmosphere this home has to offer.

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 122, 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

  $330,000

  $5K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 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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  /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

  $549,999

  $45K PRICE DROP

  • 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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  /26

  $259,000

  $11K PRICE DROP

  • 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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  /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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  /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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  /33

  $364,900

  $34K 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
• 

  

  /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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