Winterset, IA homes for sale & real estate

60 homes

Sort:

Recommended

OPEN SUN, 1PM TO 4PM3D WALKTHROUGH

ABOUT THIS HOME
Winterset, IA Homes for Sale
STEP INTO HISTORY in Winterset! Preservationists will appreciate this lovingly cared-for 1896 2Story, one of Winterset’s early homes, where historic charm blends w/ updates. Madison County’s famous covered bridges, John Wayne’s birthplace & numerous National Register sites, incl. America’s Underground Railroad Network to Freedom, add to the area’s unique appeal. A welcoming front porch sets the stage; inside, a gorgeous original staircase, woodwork & well-preserved hardwood floors make a lasting impression. FOUR spacious BRs + a sitting/bonus room offers flexibility, incl. home office space. Large windows bring abundant natural light. Spacious kitch

$330,000

4 beds3 baths2,724 sq ft

615 N 1st Ave, Winterset, IA 50273

Historic charm • Butler's pantry • Fire pit

FLOOR PLAN

$409,000

7 beds4 baths2,600 sq ft

223 W Lane St, Winterset, IA 50273

0.4 acre lot • Garage • Built 1960

ABOUT THIS HOME
Winterset, IA Homes for Sale
Introducing a soaring piece of Winterset architectual history in this 1905 Colonial two story. A sweeping wrap around porch invites you in upon entry, perfect for late summer nights or early morning coffee conversations. Upon entry, the grand foyer greets you, opening to an elaborate hardwood staircase featuring handcrafted balusters. Fall in love with the soaring ceilings, wide baseboards, and tall windows. The formal parlor transitions into the open kitchen, overlooking a dining area that flows into the outdoor space. A modern twist without sacrificing the charming elements from the past. The first floor is finished with a half bath, convenient for guests and an additional living area. Up

$290,000

3 beds1.5 baths1,976 sq ft

612 W Jefferson St, Winterset, IA 50273

Wrap around porch • Tall windows • Half bath

ABOUT THIS HOME
Winterset, IA Homes for Sale
Thia 1.5 story home layout features two bedrooms and a bath on each floor. It is located just south of Winterset high school on South 4th Ave in Winterset. The main floor includes a formal dining room off the kitchen with included appliances. Large living room facing east with foyer off the front entrance and staircase leading to second floor. Full bath on the main floor includes closet and washer and dryer hookups. Second level includes two large bedrooms both with walk-in closets. Half bath off the hall on the upper level. Partial basement is insulated and includes a sump pump. Basement entrance is located on the outside. An important key feature is the newer windows and plumbing. Home is

$179,000

2 beds1.5 baths1,230 sq ft

1624 S 4th Ave, Winterset, IA 50273

Formal dining room • Walk-in closets • Large living room

ABOUT THIS HOME
Winterset, IA Homes for Sale
Good location for this 1 bedroom, 1 bath ranch home. Located on a large corner lot(76x102). This property would make a great investment opportunity. This property could be zoned commercial or residential.

$65,000

1 bed1 bath576 sq ft

624 W Summit St, Winterset, IA 50273

7,752 sq ft lot • Built 1904 • Listed 49 days

Property at 423 E Jefferson St, Winterset, IA 50273, 3 beds, 2 baths

$299,900

3 beds2 baths1,913 sq ft

423 E Jefferson St, Winterset, IA 50273

Property at 313 E North St, Winterset, IA 50273, 3 beds, 1 bath

$65,000

3 beds1 bath1,221 sq ft

313 E North St, Winterset, IA 50273

Property at 1479 280th St, Winterset, IA 50273

$478,577

— beds— baths— sq ft

1479 280th St, Winterset, IA 50273

Property at 1018 N 3rd Ave, Winterset, IA 50273, 2 beds, 2 baths

$289,900

2 beds2 baths1,426 sq ft

1018 N 3rd Ave, Winterset, IA 50273

Property at 310 W Washington St, Winterset, IA 50273, 4 beds, 2 baths

$349,000

4 beds2 baths2,430 sq ft

310 W Washington St, Winterset, IA 50273

Property at 715 N 5th St, Winterset, IA 50273, 3 beds, 2 baths

$177,500

3 beds2 baths1,456 sq ft

715 N 5th St, Winterset, IA 50273

Property at 602 N 1st Ave, Winterset, IA 50273, 4 beds, 3 baths

$259,000

4 beds3 baths2,146 sq ft

602 N 1st Ave, Winterset, IA 50273

Property at 703 E Filmore St, Winterset, IA 50273, 4 beds, 1 bath

$254,000

4 beds1 bath1,338 sq ft

703 E Filmore St, Winterset, IA 50273

Property at 401 E Benton St, Winterset, IA 50273, 4 beds, 2 baths

$310,000

4 beds2 baths1,032 sq ft

401 E Benton St, Winterset, IA 50273

Property at 816 E Washington St, Winterset, IA 50273, 3 beds, 1.5 baths

$234,900

3 beds1.5 baths1,241 sq ft

816 E Washington St, Winterset, IA 50273

Property at 1515 W Washington St, Winterset, IA 50273, 3 beds, 2 baths

$440,000

3 beds2 baths2,484 sq ft

1515 W Washington St, Winterset, IA 50273

Property at 804 N 4th Ave, Winterset, IA 50273, 4 beds, 1.5 baths

$249,999

4 beds1.5 baths1,880 sq ft

804 N 4th Ave, Winterset, IA 50273

Property at 505 E Court Ave, Winterset, IA 50273, 5 beds, 3.5 baths

$549,999

5 beds3.5 baths4,200 sq ft

505 E Court Ave, Winterset, IA 50273

Property at 305 Magnolia Pt, Winterset, IA 50273, 4 beds, 3.5 baths

$460,000

4 beds3.5 baths1,807 sq ft

305 Magnolia Pt, Winterset, IA 50273

Property at 110 N 10th Ave, Winterset, IA 50273, 3 beds, 2 baths

$210,000

3 beds2 baths964 sq ft

110 N 10th Ave, Winterset, IA 50273

Property at 523 S 2nd St, Winterset, IA 50273, 4 beds, 2 baths

$155,000

4 beds2 baths1,556 sq ft

523 S 2nd St, Winterset, IA 50273

Property at 204 S 8th Ave, Winterset, IA 50273, 5 beds, 2 baths

$220,000

5 beds2 baths1,701 sq ft

204 S 8th Ave, Winterset, IA 50273

Property at 511 W Washington St, Winterset, IA 50273, 4 beds, 2.5 baths

$320,000

4 beds2.5 baths1,540 sq ft

511 W Washington St, Winterset, IA 50273

Property at 1474 280th St. St, Winterset, IA 50273

$537,513

— beds— baths— sq ft

1474 280th St. St, Winterset, IA 50273

Property at 715 N 3rd Ave, Winterset, IA 50273, 4 beds, 2 baths

$249,900

4 beds2 baths866 sq ft

715 N 3rd Ave, Winterset, IA 50273

Property at 1913 N 1st St, Winterset, IA 50273, 3 beds, 3 baths

$375,000

3 beds3 baths2,389 sq ft

1913 N 1st St, Winterset, IA 50273

Property at 519 W Filmore St, Winterset, IA 50273, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths1,476 sq ft

519 W Filmore St, Winterset, IA 50273

Property at 117 E North St, Winterset, IA 50273, 6 beds, 3 baths

$329,900

6 beds3 baths1,800 sq ft

117 E North St, Winterset, IA 50273

Property at 322 W Washington St, Winterset, IA 50273, 4 beds, 2 baths

$299,900

4 beds2 baths2,281 sq ft

322 W Washington St, Winterset, IA 50273

Property at 302 W Court Ave, Winterset, IA 50273, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths2,396 sq ft

302 W Court Ave, Winterset, IA 50273

Property at 118 N 5th St, Winterset, IA 50273, 3 beds, 1 bath

$169,000

3 beds1 bath1,523 sq ft

118 N 5th St, Winterset, IA 50273

Property at 121 E Benton St, Winterset, IA 50273, 2 beds, 1 bath

$213,000

2 beds1 bath848 sq ft

121 E Benton St, Winterset, IA 50273

Property at 1824 W Summit St, Winterset, IA 50273, 3 beds, 1 bath

$325,000

Land6.36 acres (lot)

1824 W Summit St, Winterset, IA 50273

Property at 1509 State Highway 92, Winterset, IA 50273, 4 beds, 2 baths

$299,000

Land3.82 acres (lot)

1509 State Highway 92, Winterset, IA 50273

Property at 2394 Cumming Rd, Winterset, IA 50273, 3 beds, 2.5 baths

$775,000

Land3.35 acres (lot)

2394 Cumming Rd, Winterset, IA 50273

Property at 2381 Highway 169, Winterset, IA 50273, 4 beds, 4 baths

$949,000

Land4.88 acres (lot)

2381 Highway 169, Winterset, IA 50273

Property at 1818 Patricia Acres Ct, Winterset, IA 50273, 3 beds, 2.5 baths

$474,000

Land2.10 acres (lot)

1818 Patricia Acres Ct, Winterset, IA 50273

Property at Hogback Bridge Rd, Winterset, IA 50273

$195,000

Land7.48 acres (lot)

Hogback Bridge Rd, Winterset, IA 50273

Property at 1600 Roseman Bridge Rd, Winterset, IA 50273

$39,900

Land2.86 acres (lot)

1600 Roseman Bridge Rd, Winterset, IA 50273

Property at 5219 Cherrywood Ln, Winterset, IA 50273, 4 beds, 3 baths

$559,000

Land2.24 acres (lot)

5219 Cherrywood Ln, Winterset, IA 50273

Property at 2607 Quail Ridge Trl, Winterset, IA 50273, 4 beds, 1.5 baths

$399,900

Land3.00 acres (lot)

2607 Quail Ridge Trl, Winterset, IA 50273

Viewing page 1 of 2

Average home prices near Winterset, IA

Cities

Zip Codes

50273 homes for sale
$289,950

Winterset, IA real estate trends

All Home Types trends in Winterset, IA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$260,000

+1.0% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

Winterset, IA

$260,000

+1.0%

See more Winterset, IA market insights

More to explore in Winterset, IA

Featured
Price
Bedroom

How to buy a house in Winterset, IA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Buy the right home at the right price near Winterset with a local Redfin real estate agent.

Popular Markets in Iowa

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.