Saint Charles, IA Homes for Sale

• 

  

  

  /35

  $226,900

  • 3 Beds
  • 1.5 Baths
  • 958 Sq Ft

  513 W Hutchings St, Winterset, IA 50273

  Step into this beautifully remodeled 2025 home complete with 3 bedrooms and 1.5 bathrooms. Thoughtfully updated throughout, this residence includes new sheet rock and fresh paint, new LVP flooring, new central air system and duct work, upgraded plumbing and electrical and all new windows. Lage kitchen features custom Amish-built cabinetry, quartz countertops and just around the corner a main

  

  Toni Tindle

  Covered Bridge Realty

  (515) 481-5094

  513 W Hutchings St, Winterset, IA 50273
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  /35

  $450,000

  • 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 proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & 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
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  /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
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  /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
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  /15

  $1,150,000

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

  0 Clark Tower Rd, Winterset, IA 50273

  Prime Rural Residential Developmental Land Offering | Just south of Winterset, IowaPeoples Company is proud to represent 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 Residentialan

  Andrew Zellmer

  0 Clark Tower Rd, Winterset, IA 50273
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  /29

  $360,000

  • 5 Beds
  • 4 Baths
  • 2,110 Sq Ft

  309 N 15th Ave, Winterset, IA 50273

  Don’t miss your chance to own this beautifully appointed 2-story home tucked away on a quiet street. From the moment you arrive, the inviting front porch sets the tone—perfect for sipping your morning coffee or unwinding with a sunset view. Step inside to an open-concept layout designed for gathering, with seamless flow from the spacious living areas to the patio, ideal for evening

  Sarah Cowman Homefront Real Estate, LLC

  309 N 15th Ave, Winterset, IA 50273
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  /30

  $499,900

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

  400 N 14th Ave, Winterset, IA 50273

  This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless style. Built in 2013 and exceptionally cared for, every detail radiates warmth, quality, and convenience. Step inside to an inviting open layout highlighted floor-to-ceiling stone fireplace—a stunning centerpiece for cozy evenings or lively gatherings with family and friends. The beautiful kitchen is both

  Sarah Cowman Homefront Real Estate, LLC

  400 N 14th Ave, Winterset, IA 50273
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  /25

  $614,000

  • 5 Beds
  • 2 Baths
  • 2,074 Sq Ft

  2283 Pioneer Ave, Winterset, IA 50273

  Escape to the serenity of this stunning story-and-a-half home nestled on 20 acres of timber, open land, and a flowing creek. Built in 1997 and tastefully remodeled in 2018, this 5-bedroom, 2-bath home offers the perfect blend of comfort, functionality, and natural beauty. Step inside to discover custom hickory cabinets in the kitchen with stainless steel appliances, cozy living spaces, and warm

  Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273
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  /35

  $389,900

  • 4 Beds
  • 2.5 Baths
  • 1,333 Sq Ft

  215 W Buchanan St, Winterset, IA 50273

  Completely Renovated Winterset Gem!This 4-bedroom, 3-bath home (1,333 sq ft above grade + 409 finished basement) is in the heart of Winterset—steps from parks, schools, and the historic town square. Enjoy all Winterset has to offer, including the John Wayne Birthplace & Museum, the famous Covered Bridges of Madison County, and year-round festivals.Fully renovated from top to

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
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  /31

  $314,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  516 S 8th Ave, Winterset, IA 50273

  Step into history without the hassle! Built in 1890 and recently renovated, this 4-bedroom, 2-bath home offers the character you love with the updates you need. Sunlight pours through abundant windows, filling the spacious layout and large kitchen. Situated on nearly a half-acre (.418) lot right in town, you’ll have plenty of room to spread out, just minutes from Main Street and the birthplace of

  Tiffany Marcum The American Real Estate Co.

  516 S 8th Ave, Winterset, IA 50273
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  /35

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,724 Sq Ft

  615 N 1st Ave, Winterset, IA 50273

  This beautifully remodeled residence combines timeless charm with modern comfort. Step inside to discover hardwood floors and a striking, gracefully designed staircase that sets the tone for the entire home. The inviting front porch offers the perfect spot to welcome guests or enjoy peaceful evenings outdoors. Featuring four generously sized bedrooms plus a bonus room, and a full bath on each

  Sarah Cowman Homefront Real Estate, LLC

  615 N 1st Ave, Winterset, IA 50273
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  /26

  $404,900

  • 4 Beds
  • 3.5 Baths
  • 1,710 Sq Ft

  1011 N 14th Ave, Winterset, IA 50273

  Discover your own slice of heaven right in town! This inviting two-story home is set in a friendly neighborhood where there's plenty of room to play and grow. The thoughtful layout makes the most of every square foot, creating spaces that work well for everyday life.The main level welcomes you with a handy drop zone, half bath, and a office with French doors. The open kitchen and family room

  Michelle Hanson RE/MAX Concepts

  1011 N 14th Ave, Winterset, IA 50273
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  /35

  $335,000

  • 4 Beds
  • 2 Baths
  • 1,912 Sq Ft

  59 E Benton St, Winterset, IA 50273

  Step inside this well-loved home that blends timeless character with modern updates—ready for its next owner to make it their own. The home’s original woodwork, in excellent condition, adds warmth and charm throughout. Enjoy relaxing mornings with coffee or peaceful evenings with dinner on the inviting front porch. Inside, you’ll find a spacious living room that flows seamlessly into a formal

  Sarah Cowman Homefront Real Estate, LLC

  59 E Benton St, Winterset, IA 50273
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  /35

  $475,000

  • 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
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  /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
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  /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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  /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
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  /35

  $330,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  724 W Jefferson St, Winterset, IA 50273

  Prepare to be impressed with the renovations done to bring this stately home back to it's orignal glory! Step up to the inviting front covered porch & through the original leaded glass door into the stunning entryway showcasing the gorgeous stairway & original woodwork. The orignal hardwood floors flow throughout the entry room, HUGE living room, and into the formal dining room. Off the living

  Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson St, Winterset, IA 50273
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  /29

  $260,000

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  120 S 8th Ave, Winterset, IA 50273

  Opportunity knocks on this ready-to-renovate 3-bed 2 and 1/2 bath ranch home. This has one of the coolest back yards in town! Professionally landscaped with numerous flowers, plants, bushes, and trees with your very own pond with a cool shed area. The house has a great layout with a large living room, very spacious kitchen with plenty of cabinets and countertop space, a large dining area, 3

  Sarah Cowman Homefront Real Estate, LLC

  120 S 8th Ave, Winterset, IA 50273
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  /35

  $1,385,000

  • 5 Beds
  • 5 Baths
  • 4,032 Sq Ft

  1890 Hogback Bridge Rd, Winterset, IA 50273

  Rare 30-acre M/L retreat in Madison County with 4,032 sq. ft. custom home. Main level features gourmet kitchen with 2 dishwashers & walk-in pantry, spacious living areas, and a primary suite with sitting room, spa bath, huge walk-in closet & laundry. Upstairs offers loft with wet bar, 4 bedrooms, 3 baths & 2nd laundry. Heated/cooled 2,240 sq. ft. attached garage includes office, canning kitchen,

  Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
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  /21

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  315 S 5th Ave, Winterset, IA 50273

  Charming Brick Home with Bonus Space! This well-kept 2 bedroom, 2 bath brick home offers both comfort and versatility. Inside, you’ll find a spacious layout with a bonus room that could easily serve as a 3rd bedroom, home office, or hobby space. Recent updates include a newer roof and AC, giving you peace of mind for years to come. The exterior features a fenced-in yard, perfect for pets, kids,

  Dustin Crawford Iowa Home & Land Realty

  315 S 5th Ave, Winterset, IA 50273
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  /18

  $260,000

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

  1413 W Washington St, Winterset, IA 50273

  Move-in ready and 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
• 

  

  /23

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  303 E Court Ave, Winterset, IA 50273

  Welcome to one of the charming historical homes in Winterset. Walking through the front entrance, visitors are greeted with natural light spilling across the hardwood floors. As they enter the kitchen, the openness is easily noticeable making it a perfect place to host or have family dinners. The living room has charming built-ins which adds to the cozy feel. The laundry area is located on the

  Tamra Yeager Pro Team Realty

  303 E Court Ave, Winterset, IA 50273
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  /14

  $150,000

  • Land
  • 3.67 Acres
  • $40,872 per Acre

  2228 Holliwell Valley Ct, Winterset, IA 50273

  Picture your dream home nestled on 3.67 acres in the heart of Madison County. This flat, buildable acreage is framed by mature trees and rolling valleys, creating a private country retreat. With utilities available at the road and multiple sites to choose from, you can design the perfect layout for your new home. Just a short drive from Winterset and steps away from the Holliwell Valley Covered

  Misty Darling BH&G Real Estate Innovations

  2228 Holliwell Valley Ct, Winterset, IA 50273
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  /31

  $1,750,000

  • Land
  • 141.79 Acres
  • $12,342 per Acre

  00 N River Trail, Winterset, IA 50273

  We are pleased to present this unique 141.79-acre property located just north of Winterset in Madison Co., IA. Located just 1.5 miles off of Cumming HWy and within a 30-minute drive to the Des Moines Metro, this highly maintained and manicured property offers a rare mix of income-producing tillable land, recreational opportunities, building site potential, and a pole building with living quarters

  Eric Lonnevik Peoples Company

  00 N River Trail, Winterset, IA 50273
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  /25

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft

  722 W Mills St, Winterset, IA 50273

  Beautifully maintained 3-bedroom, 2-bath ranch showcasing an inviting open floor plan with dining area. The partially finished basement includes a comfortable family room with an egress window, perfect for entertaining or relaxing. Step outside to a private, fenced backyard featuring a charming deck that offers a peaceful view of the yard—ideal for gatherings or quiet evenings at home.

  Sarah Cowman Homefront Real Estate, LLC

  722 W Mills St, Winterset, IA 50273
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  /35

  $540,500

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

  2571 250th Ln, Winterset, IA 50273

  Stunning Executive Building site located just south of Winterset on a dead-end road. If you have been dreaming of a country escape, this is something you need to consider. Approximately 23 acres to be surveyed off will include clean timber, spring-fed creek with well possibilities, wild flowers, limestone ledges, nice rolling pasture, and a stocked pond. Stunning views and wildlife galore!

  Sarah Cowman Homefront Real Estate, LLC

  2571 250th Ln, Winterset, IA 50273
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  /11

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft

  2366 Holliwell Bridge Rd, Winterset, IA 50273

  3 Bedroom - 2 Bath mobile home with a 780 Sq Ft family room added! Located on 6 acres more or less! Property is a combination of Timber and open grass. There is a building pad ready for construction and owners have planted 60 new trees in this area. Property has well that was drilled new in 2003. There is rural water located across from the house. New shingles in 2022, septic tank was new

  Betty Craig Saylor Realty

  2366 Holliwell Bridge Rd, Winterset, IA 50273
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  /35

  $629,900

  • 5 Beds
  • 3.5 Baths
  • 2,229 Sq Ft

  1795 Millstream Ct, Unincorporated, IA 50273

  This stunning 1.5-story home sits on just over 3 acres of paved countryside 3miles north of Winterset & only 20 minutes from West Des Moines. With 5 bedrooms plus an exerciseroom, 4 bathrooms, and more than 3,200 sq. ft. of finished living space, this property combines comfort,style, and convenience. Step inside to find a soaring 2-story vaulted great room with a fireplace. The

  Jenny Wille Iowa Realty Mills Crossing

  1795 Millstream Ct, Unincorporated, IA 50273
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  /16

  $209,000

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft

  520 W Madison St, Winterset, IA 50273

  Charming 2BR/1BA Townhome with Attached Garage in the Heart of Madison County! This inviting home features an open-concept layout with warm earth tones throughout. Enjoy a spacious kitchen that flows into the dining area and family room, perfect for relaxing or entertaining. Vaulted ceilings enhance the airy feel, while large windows bring in natural light. The ADA-compliant, no-step entry offers

  Nicholas Scar Iowa Realty Mills Crossing

  520 W Madison St, Winterset, IA 50273
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  /23

  $159,900

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  516 W Summit St, Winterset, IA 50273

  Are you looking for a house with a LARGE YARD, close to SCHOOLS and WINTERSET TOWN SQUARE.Come take a look at this well-maintained ranch, on a big lot, in the beautiful town of Winterset! The three nice sized bedrooms also have great closet space. You will also like the open kitchen/dining area, with plenty of natural light, that leads out to the NEW LARGE DECK, perfect for morning coffee and

  Betsy Breeding Realty ONE Group Impact

  516 W Summit St, Winterset, IA 50273
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  /34

  $650,000

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

  719 E Washington St, Winterset, IA 50273

  If the "Wow Factor" is what you are hoping for in a home, this one is a must-see! This home was gutted down to the studs and completely rebuilt, so it is just like brand new! Walk in the front door, and you will love all the natural light as you enter the living room with a cozy gas fireplace. The large dining area adjoins the gorgeous kitchen with tons of cabinets and countertop space. There is

  Sarah Cowman Homefront Real Estate, LLC

  719 E Washington St, Winterset, IA 50273
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  /27

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  202 S 7th Ave, Winterset, IA 50273

  Full of character and charm, this home sits on a desirable corner lot in the heart of Winterset Step inside to bright living spaces with new flooring throughout. The functional kitchen features ample storage and prep space and opens to the dining room. An inviting 3 season room steps from the living room and adjoined to the garage offers the perfect bonus space for entertaining or quiet mornings.

  Tiffany Ehler Boutique Real Estate

  202 S 7th Ave, Winterset, IA 50273
• 

  

  /23

  $309,900

  • 3 Beds
  • 1.5 Baths
  • 2,130 Sq Ft

  721 W Court Ave, Winterset, IA 50273

  Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

  Larry Corkrean Madison County Realty

  721 W Court Ave, Winterset, IA 50273
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  /27

  $247,900

  • 3 Beds
  • 2 Baths
  • 1,106 Sq Ft

  316 E Jefferson St, Winterset, IA 50273

  Charming Victorian that has been fully renovated. The living room has ten-foot ceilings, beautiful chandeliers, and a gas fireplace. In the main bedroom, there is a unique stained glass window. Walking into the kitchen, you are greeted with quartz countertops and custom cabinets, which adds a modern touch. All the appliances are 2-3 years old. Washer/dryer hookups are in the basement along with a

  Tamra Yeager Pro Team Realty

  316 E Jefferson St, Winterset, IA 50273
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  /20

  $139,500

  • Land
  • 4.15 Acres
  • $33,614 per Acre

  TBD 176th Ct, Winterset, IA 50273

  Located just 2 miles north of Winterset and just east off Highway 169, this 4.15-acre property offers a rare opportunity to build your dream home in a scenic setting.Perched on a hillside overlooking the beautiful North River Valley, the property features two potential build site locations with breathtaking views. With utilities available at the highway, the groundwork is set for an easy

  Colin Ortmeier Kiloterra

  TBD 176th Ct, Winterset, IA 50273
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  /11

  $655,384

  • Land
  • 96.11 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
• 

  

  /4

  $74,500

  • Land
  • 3 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

  $699,000

  • 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
• 

  

  /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

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