Homes for Sale near Winterset Middle School

• 

  

  

  /27

  $499,000

  • 4 Beds
  • 3 Baths
  • 1,404 Sq Ft

  2155 148th St, Winterset, IA 50273

  Tranquil Country Living Just Minutes from the City Experience peaceful country living with city convenience on this stunning 4.19-acre corner lot innorth-central Madison County—just 20 miles west of Jordan Creek Mall and 7 miles from I-80.A tree-lined drive welcomes you to this serene property featuring a 36x34 metal outbuilding withpower, concrete floors, and 14-ft overhead

  

  Cindy Miller

  Keller Williams Realty GDM

  (515) 493-7953

  2155 148th St, Winterset, IA 50273
• 

  Explore Winterset Middle School

• 

  

  

  /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
• 

  

  

  /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 over the sink window facing south, included

  

  Toni Tindle

  Covered Bridge Realty

  (515) 495-5285

  609 E Filmore St, Winterset, IA 50273
• 

  

  

  /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
• 

  

  

  /6

  $275,000

  • Land
  • 10.23 Acres
  • $26,882 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Don't miss this rare opportunity to own 10 acres m/l of picturesque countryside just 8 miles west of Winterset, situated on a hard surface road and a prime corner lot. This walkout lot is ready for your dream home with rural water, electricity, and a driveway already added, saving you the time and expense of major improvements. The gently rolling terrain offers stunning views and the perfect

  

  Chris Kew

  RE/MAX Precision

  (515) 531-5829

  2212 Deer Run Ave, Winterset, IA 50273
• 

  

  /15

  $149,000

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

  207 E Buchanan St, Winterset, IA 50273

  Discover this inviting frame home located near the Winterset Square. The main level features a generous sized living room with an enclosed entryway, a full bathroom, and a main floor bedroom. The kitchen opens to the dining area, creating a warm and functional space for everyday living.Upstairs, you'll find two additional bedrooms, offering flexibility for family, guests, or a home

  

  Toni Tindle

  Covered Bridge Realty

  (515) 493-7698

  207 E Buchanan St, Winterset, IA 50273
• 

  

  /9

  $272,875

  • Land
  • 29.49 Acres
  • $9,253 per Acre

  Pioneer Ave, Winterset, IA 50273

  Discover this beautiful small-acreage in Madison County, located less than 10 minutes from Winterset and just 30 minutes from West Des Moines. Situated less than a mile from pavement, this farm offers a perfect blend of tillable ground and open pasture. Approximately 8 acres are currently in a corn and soybean rotation, with the remaining balance used for pasture and recreation. A small creek

  KILOTERRA KILOTERRA KILOTERRA | Land Sales & Auctions

  Pioneer Ave, Winterset, IA 50273
• 

  

  /37

  $495,000

  • Land
  • 60 Acres
  • $8,250 per Acre

  2340 Holliwell Bridge Rd, Winterset, IA 50273

  KILOTERRA is proud to present this diverse 60-acre property in Madison County, offering a rare blend of productive land, prime hunting, and build potential. Located less than 10 minutes from Winterset and just 30 minutes from West Des Moines, this property delivers the ideal balance of rural seclusion and modern convenience. Access is available from the east, west, and south sides, with pavement

  KILOTERRA KILOTERRA KILOTERRA | Land Sales & Auctions

  2340 Holliwell Bridge Rd, Winterset, IA 50273
• 

  

  /41

  $1,225,000

  • Land
  • 153.2 Acres
  • $7,996 per Acre

  290th Street, MacKsburg, IA 50155

  153.2 Acres Madison County, IowaLocated north of Macksburg Road on 290th Street, this 153.2-acre farm offers an excellent balance of income-producing acres and recreational opportunities. With 107.62 acres currently in row crop production and a CSR2 rating of 48.53, the farm provides steady returns and is well-suited for expansion of an existing operation. The cropland has been in a corn

  KILOTERRA KILOTERRA KILOTERRA | Land Sales & Auctions

  290th Street, MacKsburg, IA 50155
• 

  

  /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 Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /27

  $437,520

  • Land
  • 36.46 Acres
  • $12,000 per Acre

  0 Iowa 92, Prole, IA 50229

  Peoples Company is proud to present 36.46 acres m/l of exceptional recreational land with Middle River frontage, conveniently located along Highway 92 in Madison County, Iowa. Situated just 10 miles east of Winterset, and only 15 minutes from the Des Moines Metro, this property offers a blend of recreational opportunities and natural beauty, all within a short drive of urban amenities.The

  Bryan Bergdale Peoples Company

  0 Iowa 92, Prole, IA 50229
• 

  

  /30

  $349,900

  • 5 Beds
  • 2 Baths
  • 1,700 Sq Ft

  150 S 4th St, Patterson, IA 50218

  Enjoy living along the Middle River! This spacious 5-bedroom, 2-bath home sits on just under 1.5 acres with direct river access right off the backyard. Watch deer, turkey, and other wildlife from the wrap-around deck looking through mature trees and beautiful views. Property features multiple outbuildings, a mancave, chicken coop, and exterior storage- offering plenty of space for hobbies or

  Rachel Eller Summerset Realty

  150 S 4th St, Patterson, IA 50218
• 

  

  /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
• 

  

  /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
• 

  

  /28

  $369,900

  • 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 bottom with all-new

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /17

  $340,000

  • 2 Beds
  • 1.5 Baths
  • 1,623 Sq Ft

  2797 Pioneer Ave, Peru, IA 50222

  Affordable acreage alert! Great location for this 2 bedroom, 1.5 bath brick home on 4.2 acres. This home has been lovingly cared for by the current owners for 14 years, but it's time for a new family to make new memories. This would make a great hobby farm or an acreage for 4-H projects. The current owner had horses thru the years. 1st floor laundry room, spacious kitchen/dining area. Large

  Randall Henry Madison County Realty

  2797 Pioneer Ave, Peru, IA 50222
• 

  

  /35

  $449,900

  • 5 Beds
  • 3 Baths
  • 2,137 Sq Ft

  812 N 8th Ave, Winterset, IA 50273

  Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort and style. You will love the stunning stone fireplace as the focal point in the living room with vaulted-ceilings, creating a warm and welcoming atmosphere. The kitchen is nice with granite countertops and plenty of cabinets. The primary bedroom is complete with an ensuite featuring a tile shower with dual

  Matt Cole RE/MAX Concepts

  812 N 8th Ave, Winterset, IA 50273
• 

  

  /35

  $370,000

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

  701 North St, Patterson, IA 50218

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

  Becky Knight Iowa Realty Mills Crossing

  701 North St, Patterson, IA 50218
• 

  

  /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
• 

  

  /34

  $350,000

  • 5 Beds
  • 2.5 Baths
  • 2,968 Sq Ft

  323 W Jefferson St, Winterset, IA 50273

  Exquisite historic home in the heart of Winterset just blocks from the bustling downtown square. If you love a quality historic home, this one is for you! This Freestyle Queen Anne Victorian 2-story is sure to impress. The past 2 owners have taken exquisite care of this gem. You will love the original woodwork hard floors, leaded glass & character! A front porch greets you as you enter complete

  Sarah Cowman Homefront Real Estate, LLC

  323 W Jefferson St, Winterset, IA 50273
• 

  

  /35

  $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
• 

  

  /35

  $440,000

  • 5 Beds
  • 4 Baths
  • 3,520 Sq Ft

  204 W Washington St, Winterset, IA 50273

  If you're looking for ** WOW ** this. is. IT!! This stunning 1875 two story has been well cared for and offers a long list of modern amenities. Situated just a couple blocks from the historic Winterset square and close to schools, restaurants and retail on a large corner lot with outdoor living and perennials waiting for you. Relax on the wrap around porch or entertain on the back patio

  Alyssa Tadlock Madison County Realty

  204 W Washington St, Winterset, IA 50273
• 

  

  /32

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  1541 Nature Ct, Winterset, IA 50273

  Endless possibilities on nearly 5 acres of peaceful countryside! This 3-bedroom, 2-bath manufactured home sits on 4.98 acres off a private drive, offering beautiful views and plenty of room to enjoy country living your way. With no covenants or restrictions, you’re free to bring animals, build a dream home, add a shop, or simply enjoy the open space. The home features an open layout with updated

  Elizabeth Gordon Realty ONE Group Impact

  1541 Nature Ct, Winterset, IA 50273
• 

  

  /34

  $675,000

  • 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 5+ acres just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways. The home boasts a large open-concept living area anchored by a beautiful double-sided fireplace,

  Alyssa Tadlock Madison County Realty

  2218 N John Wayne Dr, Winterset, IA 50273
• 

  

  /16

  $189,000

  • Land
  • 12.6 Acres
  • $15,000 per Acre

  0000 295th St, Lorimor, IA 50149

  This 12.6± acre tract in Madison County offers the perfect combination of peaceful country living and convenient access to town. Located just a half mile off the pavement, the property features a beautiful hilltop build site overlooking the surrounding countryside—an ideal setting for your dream home or weekend retreat. The land offers a balanced mix of open grassland and native habitat, creating

  Will Cooper Midwest Land Group LLC

  0000 295th St, Lorimor, IA 50149
• 

  

  /31

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 988 Sq Ft

  501 W Hutchings St, Winterset, IA 50273

  Welcome to this beautiful home in the heart of Winterset. This property features 3-beds, 1.5 baths, in almost 1,000 sq ft on the main level and a partially finished basement for extra storage or living space. Enjoy a nice-sized yard perfect for outdoor activities. The attached 1-car garage adds convenience year-round. Located within walking distance to the school.

  Krymsin Graf Iowa Realty Ankeny

  501 W Hutchings St, Winterset, IA 50273
• 

  

  /23

  $229,900

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

  114 S 14th Ave, Winterset, IA 50273

  Well-maintained 4-bedroom ranch on a corner lot in Winterset! This home offers convenient single-level living with a functional layout and plenty of natural light. The detached 2-car garage provides excellent storage and parking. Great location near the Winterset Aquatic Center, parks, and other community amenities. A wonderful opportunity to own a home in a desirable area of town!

  Rachel Eller Summerset Realty

  114 S 14th Ave, Winterset, IA 50273
• 

  

  /17

  $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 Real Broker, LLC

  4922 Cedar Ln, Winterset, IA 50273
• 

  

  /21

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,174 Sq Ft

  110 E Grade St, Winterset, IA 50273

  Step into this beautifully remodeled and charming single-story home, thoughtfully designed to combine comfort and modern living. This inviting 3-bedroom, 2-bath residence showcases a spacious eat in kitchen (appliances included) and an airy, naturally lit living room with vaulted ceiling that creates a welcoming atmosphere throughout. This property offers both comfort and function. The primary

  Sarah Cowman Homefront Real Estate, LLC

  110 E Grade St, Winterset, IA 50273
• 

  

  /35

  $1,500,000

  • 3 Beds
  • 2 Baths
  • 2,272 Sq Ft

  1671 Us Highway 169 None, Winterset, IA 50273

  Horse Lover's Paradise in the beautiful rolling hills of Madison County. Charming 1929 Craftsman home on pavement with everything you need for your horses/livestock and your family! Set on 20 acres with 2 ponds, 5 paddocks (4 with sheds, all with auto waterers), 2 additional outbuildings plus an exceptional indoor arena with observation area and an attached 6-stall barn with wash rack, tack room

  Mindy Blasberg LPT Realty, LLC

  1671 Us Highway 169 None, Winterset, IA 50273
• 

  

  /35

  $650,000

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  1706 Mueller Ct, Winterset, IA 50273

  Nature lover’s dream! Tucked away on 8.1 breathtaking acres, this property offers peace, privacy, and a front-row seat to nature’s beauty. Mature trees surround the home, creating a serene setting filled with wildlife and seasonal color. Step inside to an open-concept main level designed to bring the outdoors in, featuring a spacious eat-in kitchen with walk-in pantry and large windows framing

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  1706 Mueller Ct, Winterset, IA 50273
• 

  

  /12

  $477,000

  • Land
  • 36 Acres
  • $13,250 per Acre

  2235 310 St, Lorimor, IA 50149

  36 acres in Madison County ready for your vision! This property has been cleared of previous homes and outbuildings, leaving a fresh slate for new owners to build their dream home, establish a hobby farm, or enjoy as recreational land. Rural water and a meter pole are already on site, and the sewer system was reported up to code per the previous owner. The property offers a blend of open ground

  Kenzie Brandsgard Iowa Realty Indianola

  2235 310 St, Lorimor, IA 50149
• 

  

  /28

  $924,900

  • 4 Beds
  • 2.5 Baths
  • 1,534 Sq Ft

  2176 148th St, Winterset, IA 50273

  Discover 17.9 Acres of Updated Country Living. Welcome to your dream acreage! This beautifully updated home sits on 17.9 acres of rolling countryside with a private pond, woods, and multiple outbuildings. Inside, the main level has been completely renovated with a brand-new kitchen featuring quartz countertops, sleek cabinetry, stainless appliances, and an open floor plan filled with natural

  Jason Russell Realty ONE Group Impact

  2176 148th St, Winterset, IA 50273
• 

  

  /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
• 

  

  /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 Iowa with a 4,000+ sq. ft. custom home. Incredible views of the countryside teeming with wildlife including white-tailed deer and turkey. 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

  Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /18

  $249,900

  • 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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