Winterset, IA Homes

/25
Est $186,407 Not Listed For Sale
- 2 Beds
- 1 Bath
- 984 Sq Ft
422 W Filmore St, Winterset, IA 50273

422 W Filmore St, Winterset, IA 50273

/35
$285,000
- 3 Beds
- 2 Baths
- 1,913 Sq Ft
423 E Jefferson St, Winterset, IA 50273

Classic 1920 Craftsman with all of the charm and character you'd expect. As you walk up to the front porch you'll never want to leave! Perfect spot for your morning coffee or lounging at the end of a long day. As you enter, you'll immediately see the exposed wood beams in the family room that make it a cozy space. Newer gas fireplace is the focus of the family room, flanked by built in

Jennifer Stover Madison County Realty

423 E Jefferson St, Winterset, IA 50273
/28
$358,409 Sold Apr 04, 2025
- 1,712 Sq Ft
- $209/SF
- 635 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
1912 Dogwood Ln, Winterset, IA 50273

Beautiful new construction of this 2-story home in a quiet neighborhood. Home features 3 bedrooms on 2nd floor, primary with carpet, tray ceiling, ceiling fan and primary bath with double sink, tile shower, LVP flooring and walk in closet. Bedrooms 2 and 3 have vaulted ceilings and carpet. Hall bath with quartz countertop, full tub/shower, and LVP flooring. Laundry room located on upper level.

Robert D. Weeks Iowa Realty Waukee

1912 Dogwood Ln, Winterset, IA 50273

/24
Est $275,145 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
604 W Filmore St, Winterset, IA 50273

604 W Filmore St, Winterset, IA 50273

/15
$189,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
408 E Benton St, Winterset, IA 50273

Charming & Updated in Winterset! This adorable home is move-in ready with tons of recent upgrades you'll love. Step into a brand-new kitchen and bathroom featuring modern finishes, complemented by stylish LVP flooring and fresh carpet throughout. The exterior shines with new siding and windows, offering both great curb appeal and energy efficiency. Sitting on a huge yard, there's plenty of space

Jamie Adkins RE/MAX Precision

408 E Benton St, Winterset, IA 50273
/35
$315,000 Sold Apr 01, 2025
- 1,984 Sq Ft
- $159/SF
- 103 Days On Market
- 4 Beds
- 2 Baths
- Built 1925
119 E Buchanan St, Winterset, IA 50273

Classic charm and character describe this beautifully maintained 4-bedroom Winterset home, located on a tree-lined street. Walk up to the enclosed porch and stylish brick of this craftsman home, with southern exposure, it is the perfect spot to enjoy a morning cup of coffee or a rocking chair in the afternoon. Step inside to the charming living space perfect for the whole family to enjoy movie

Adam Bugbee EXP Realty, LLC

119 E Buchanan St, Winterset, IA 50273

/25
Est $171,707 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
809 E Benton St, Winterset, IA 50273

809 E Benton St, Winterset, IA 50273

/9
$216,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
413 E Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

Alyssa Tadlock Madison County Realty

413 E Madison St, Winterset, IA 50273
/15
$313,000 Sold Mar 28, 2025
- 1,356 Sq Ft
- $231/SF
- 61 Days On Market
- 3 Beds
- 3 Baths
- Built 2021
815 N 11th Avenue Cir, Winterset, IA 50273

Beautiful newer home with a large primary suite and a finished basement with 3rd bedroom. Large rear deck. The home is move in ready. Located on a cul de sac street for added peacefulness. There is an attached two car garage. Property is being sold As-Is. Inspections are for buyers knowledge only. Buyer will be responsible for all abstracting costs. Seller is The Secretary of Veterans

Brent Kelso Silverado Realty

815 N 11th Avenue Cir, Winterset, IA 50273

/16
Est $239,979 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
602 E Benton St, Winterset, IA 50273

602 E Benton St, Winterset, IA 50273

/8
$220,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
411 W Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet in bedrooms and a

Alyssa Tadlock Madison County Realty

411 W Madison St, Winterset, IA 50273
/29
$85,000 Sold Mar 28, 2025
- 1,232 Sq Ft
- $69/SF
- 95 Days On Market
- 3 Beds
- 1 Bath
- Built 1890
808 S 5th Ave, Winterset, IA 50273

Large corner double lot, close to School and Hospital. 3 bed 1 bath. Mature trees surround the property giving a tranquil feeling. Winterset is a vibrant community with entertainment and activities year around. Needs repairs before ready to live in. Selling "As Is".

Roger Queck Pro Team Realty

808 S 5th Ave, Winterset, IA 50273

/20
Est $267,146 Not Listed For Sale
- 4 Beds
- 2 Baths
- 924 Sq Ft
802 E Benton St, Winterset, IA 50273

802 E Benton St, Winterset, IA 50273

/19
$229,500
- 3 Beds
- 1 Bath
- 1,118 Sq Ft
223 N 8th St, Winterset, IA 50273

Amazing home renovation! Sweet ranch home on a large corner lot. 3 bedroom, 1 bath, 1118sf. The all new kitchen is efficient with a breakfast bar all new cabinetry/countertops and newer stainless steel appliances. Enjoy your morning coffee in the sunny dining area right off the kitchen. The spacious breezeway is the perfect spot for 1st floor laundry and plenty of extra room for coats/shoes. Next

Jennifer Stover Madison County Realty

223 N 8th St, Winterset, IA 50273
/5
$369,555 Sold Mar 27, 2025
- 1,400 Sq Ft
- $264/SF
- 99 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
301 Maple Point, Winterset, IA 50273

Stryker Ranch with over-sized 3 car garage. Front porch with 2 stone base posts. 9'ceilings throughout main floor. Open stairs to basement. Granite or quartz counter tops in baths and kitchen. Kitchen boasts of a large walk-in pantry and stainless-steel appliances. White cabinets throughout. Luxury vinyl flooring. Gas fireplace. Master bath with raised vanity and elongated stool. High-efficiency

Robert D. Weeks Iowa Realty Waukee

301 Maple Point, Winterset, IA 50273

/24
Est $273,366 Not Listed For Sale
- 2 Beds
- 1 Bath
- 840 Sq Ft
317 E North St, Winterset, IA 50273

317 E North St, Winterset, IA 50273

/33
$549,900
- 6 Beds
- 4 Baths
- 3,155 Sq Ft
2237 Holliwell Valley Ct, Winterset, IA 50273

Are you looking for space, peace, and charm? This 4.3-acre homestead has everything you're looking for—and more. Step into a spacious home with over 3,100 sq ft on the main level—perfect for entertaining, relaxing, and enjoying life to the fullest.At the heart of the home is a gorgeous kitchen with soft-close drawers, a walk-in pantry, and breathtaking views of the fenced backyard and peaceful

Wendy Eilander RE/MAX Concepts

2237 Holliwell Valley Ct, Winterset, IA 50273
/26
$229,000 Sold Mar 26, 2025
- 2,438 Sq Ft
- $94/SF
- 131 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1910
304 W Jefferson St, Winterset, IA 50273

Charming 1900's Traditional Two Story Home in the Heart of Winterset! Located in the heart of a peaceful, tree lined neighborhood, this gem is perfect for those seeking a home w/Character and timeless appeal. Original natural woodwork, & floors, intricate moldings,& large windows that fill each room w/natural light. This home boasts 4 beds, 2 baths, spread across the two levels. You will also

Tobi Sharon RE/MAX Precision

304 W Jefferson St, Winterset, IA 50273

/20
Est $214,357 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,252 Sq Ft
506 E Filmore St, Winterset, IA 50273

506 E Filmore St, Winterset, IA 50273

/18
$240,000
- 2 Beds
- 2 Baths
- 1,480 Sq Ft
715 W North St, Winterset, IA 50273

Check out this adorable home makeover! 2 bedroom, 2 bath, 1480sf, 1st floor laundry. Great kitchen with ample counter space and a large dining area. Just off the kitchen is the 1st floor laundry and a large bonus space. This space would be perfect for a home office or extra space for kids. It also has access to the backyard. The primary bedroom has the 3/4 bath and access to the back deck.

Jennifer Stover Madison County Realty

715 W North St, Winterset, IA 50273
/13
$226,000 Sold Mar 26, 2025
- 962 Sq Ft
- $235/SF
- 219 Days On Market
- 3 Beds
- 1 Bath
- Built 1989
710 N 3rd Ave, Winterset, IA 50273

WOW! Check out this beautiful remodel. This 3 bedroom ranch is right on trend with colors and finishes. Everything is new - flooring, kitchen, bathroom, lighting, roof, windows, siding, HVAC, gutters, paint(interior&exterior), appliances. 1st floor laundry, 1 car attached garage. Nothing to do here - move right in and enjoy!

Jennifer Stover Madison County Realty

710 N 3rd Ave, Winterset, IA 50273

/18
Est $213,388 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,248 Sq Ft
510 E Filmore St, Winterset, IA 50273

510 E Filmore St, Winterset, IA 50273

/16
$460,000
- Land
- 19 Acres
- $23,785 per Acre
1122 220th St, Winterset, IA 50273

Have you been looking for the perfect recreational property? This acreage will check all of the boxes: 40X64X12 outbuilding, timber, small cabin, great hunting, pond. The outbuilding has electric, spray foam insulation, water, plumbed for bath. Don't miss the cute cabin in the middle of the timber. The cabin makes a great hunting retreat. The cabin has an electric fireplace and wall heater. This

Jennifer Stover Madison County Realty

1122 220th St, Winterset, IA 50273
/21
$185,000 Sold Mar 25, 2025
- 1,072 Sq Ft
- $173/SF
- 164 Days On Market
- 2 Beds
- 1 Bath
- Built 1926
608 W South St, Winterset, IA 50273

Adorable well maintained 2 bedroom home. Owned by the same family for over 70 years. Inviting enclosed front porch to sip your morning coffee. Large living room, eat in kitchen with plenty of cupboards. Built in cabinets and walk in shower in the bathroom. Newer roof, gutters and furnace. Back porch facing good sized flat backyard. This sweet little home is move in ready. Schedule your

Sarah Cowman Homefront Real Estate, LLC

608 W South St, Winterset, IA 50273

/20
Est $189,383 Not Listed For Sale
- 2 Beds
- 1 Bath
- 986 Sq Ft
306 E Buchanan St, Winterset, IA 50273

306 E Buchanan St, Winterset, IA 50273

/30
$245,000
- 3 Beds
- 2 Baths
- 1,206 Sq Ft
409 S 8th Ave, Winterset, IA 50273

Move right into this squeaky clean three bed two bath ranch home! This well-cared-for home has many updates, including a roof in 2020, an updated kitchen, updated flooring, a newer fence, and updated electrical! You will love the huge living room as you walk in through the front door. The living room flows into the spacious dining area and large kitchen with beautiful butcher block countertops

Sarah Cowman Homefront Real Estate, LLC

409 S 8th Ave, Winterset, IA 50273
/35
$250,000 Sold Mar 21, 2025
- Land
- 20 Acres
- $12,500 per Acre
- 16 Days On Market
2646 Fieldstone Ave, Winterset, IA 50273

Escape to the country and embrace the tranquility of this stunning 20 m/l acre property in Madison County, Iowa. Located southwest of Winterset on Fieldstone Ave, this picturesque parcel offers the perfect blend of natural beauty and recreational opportunities.Imagine building your dream home, and waking every day to take in the breathtaking views that stretch across the rolling Iowa

Charles Johnson Kiloterra

2646 Fieldstone Ave, Winterset, IA 50273

/15
Est $212,605 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
423 E Benton St, Winterset, IA 50273

423 E Benton St, Winterset, IA 50273

/29
$225,000
- Land
- 10 Acres
- $22,433 per Acre
2391 Carver Rd, Winterset, IA 50273

Perfect location right off Hwy 169 with 10 acres more or less with a pond. Rural Water and Electric located at street for access.

Nicholas Scar Iowa Realty Mills Crossing

2391 Carver Rd, Winterset, IA 50273
/13
$24,500 Sold Mar 20, 2025
- Land
- 5 Acres
- $4,667 per Acre
- 161 Days On Market
000 Roseman Bridge Rd, Winterset, IA 50273

We are proud to present this 5.25 acre recreational tract in the heart of Madison County, just West of the town of Winterset. This property sits just 2 miles North of one of the historic Madison County covered bridges, the "Roseman Bridge". This unique property sits right on the Middle River, composed of a couple very neat sand bars and native grasses, making it the perfect getaway for

Shane Spyksma Kiloterra

000 Roseman Bridge Rd, Winterset, IA 50273

/19
Est $172,765 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
715 N 5th St, Winterset, IA 50273

715 N 5th St, Winterset, IA 50273

/25
$239,900
- Land
- 24 Acres
- $10,080 per Acre
0 Carver Rd Unit 710768, Winterset, IA 50273

Great building site with some income potential This 23.8 Acre building site has timber, some tillable ground, and access to the river. Best of all worlds with plenty of wildlife!!!

Nicholas Scar Iowa Realty Mills Crossing

0 Carver Rd Unit 710768, Winterset, IA 50273
/35
$245,500 Sold Mar 14, 2025
- 1,064 Sq Ft
- $231/SF
- 11 Days On Market
- 3 Beds
- 2 Baths
- Built 1958
901 W Jefferson St, Winterset, IA 50273

Winterset has so much to offer but still maintains that small rural community lifestyle so many people are looking for. Take the short drive from the Des Moines Metro and see this charming 3 bedroom and 2 bath home with an attached garage. Located in the NW part of town, it is convenient to walk to amenities like the beautiful aquatic center. The home is ready to move right in and has many new

Jon Niemeyer EXIT Realty & Associates

901 W Jefferson St, Winterset, IA 50273

/25
Est $250,085 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
508 E Lane St, Winterset, IA 50273

508 E Lane St, Winterset, IA 50273

/21
$199,900
- 2 Beds
- 2.5 Baths
- 1,213 Sq Ft
723 N 6th Avenue Cir, Winterset, IA 50273

Fresh Paint on main level and sellers are offering $4000 flooring allowance! Easy living in this 2 bed 2 and 1/2 bath townhome on a quiet cul de sac! You will love the open bright feel of this sweet home. The large living room has a gas fireplace and nice walk-in closet for coat storage There is a dining area by the patio doors that go out to a good sized deck. The kitchen has plenty of counter

Sarah Cowman Homefront Real Estate, LLC

723 N 6th Avenue Cir, Winterset, IA 50273
/41
$311,000 Sold Mar 14, 2025
- 2,004 Sq Ft
- $155/SF
- 147 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2019
1109 Meredith Cir, Winterset, IA 50273

This traditional 4 Bedroom two story home is anything but traditional!! The contemporary flair starts in the kitchen with white shaker cabinets mixed with a ‘removable island, ‘Smart’ Refrigerator, two oven Range, Microwave and Pantry. Dining area is convenient to large Patio with built-in gas grill, stone fire-pit and large fenced-in back yard. The spacious Family Room has built-ins for

Jordan Nelson Creston Realty

1109 Meredith Cir, Winterset, IA 50273

/26
Est $239,330 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
622 W Fremont St, Winterset, IA 50273

622 W Fremont St, Winterset, IA 50273

/35
$450,000
- 4 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
/16
$235,000 Sold Mar 07, 2025
- 796 Sq Ft
- $295/SF
- 13 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
908 E Benton St, Winterset, IA 50273

This charming bungalow offers approximately 1,500 square feet of finished living space and was built in 2006. Meticulously maintained, it provides the perfect balance of comfort and functionality. The main floor features a spacious living room with vaulted ceilings and a cozy fireplace, creating a warm and inviting atmosphere. The kitchen is equipped with stainless steel appliances, ample

Tammy Heckart RE/MAX Concepts

908 E Benton St, Winterset, IA 50273

/20
Est $187,421 Not Listed For Sale
- 2 Beds
- 1 Bath
- 896 Sq Ft
617 S 2nd St, Winterset, IA 50273

617 S 2nd St, Winterset, IA 50273

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