Winterset, IA homes for sale & real estate

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NEW 19 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Winterset, IA Homes for Sale
This executive acreage has so much to offer! Located on pavement, just outside of Winterset, in beautiful Madison County. The perfect amount of land, completely updated spacious home, and a one-of-a kind premium shop make this property a must see! The two-story home features four bedrooms, five bathrooms, 4,000+ finished sqft, numerous living and entertaining spaces, office/study, screened porch, and a large deck overlooking the peaceful timbered setting. There is at least one bedroom and one bathroom on each of the three floors which allows versatility for daily living and guests. The 45'x64'x14' shop features 1,000+ finished sqft that boasts a designer's dream kitchen with a large island

$990,000

Land4.88 acres (lot)

2381 Highway 169, Winterset, IA 50273

Large deck • Screened porch

NEW 13 HRS AGO

ABOUT THIS HOME
Winterset, IA Homes for Sale
Bring your dream home to life on this beautiful 3.24-acre wooded, walkout lot in Cumming's desireable Polo Pointe neighborhood. Enjoy incredible panoramic views to the west and north!

$250,000

Land3.24 acres (lot)

Lot 9 Polo Pointe 2, Cumming, IA 50061

Walkout lot • Panoramic views

ABOUT THIS HOME
Winterset, IA Homes for Sale
Discover your little slice of heaven. This opportunity to own a couple acres along the Middle River is a unique one that will allow for many outdoor activities. Want a spot to picnic? have a garden? Maybe you'd like to riverside camp? This gem may be just the ticket! (Address is fictitious and for general location purposes only)

$39,900

Land2.86 acres (lot)

1600 Roseman Bridge Rd, Winterset, IA 50273

Listed 3 days

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Winterset, IA Homes for Sale
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 this room. Just off the kitchen is a living room w/ statement making floor to ceiling stone wrapped fireplace! Built-in bluetooth speakers in kitchen & living room ceiling offer yet another upgrade making this home stand above the rest. The Master Suite is adjoined to a laundry ro

$559,000

Land2.24 acres (lot)

5219 Cherrywood Ln, Winterset, IA 50273

Over-sized windows • Dual vanity • Large walk-in pantry

ABOUT THIS HOME
Winterset, IA Homes for Sale
WELCOME HOME to this beautiful, CUSTOM-BUILT home on 2.1 private acres. Did I mention how CLOSE it is to Winterset? The main floor has a nice sized LIVING ROOM and FORMAL DINING ROOM, with an abundance of windows, for plenty of NATURAL LIGHT. The kitchen with GRANITE countertops, STAINLESS STEEL APPLIANCES that stay, also has a nice breakfast nook and opens to the large family room with a wood burning FIREPLACE and WET BAR. The family room opens to the nice sized PRIVATE DECK, PERFECT FOR ENTERTAINING. There is also a half bath on the main floor. On the second floor, you will find a LARGE MASTER SUITE with a walk-thru closet, separate room with the shower and bath, and a nice PRIVATE DECK.

$474,000

Land2.10 acres (lot)

1818 Patricia Acres Ct, Winterset, IA 50273

3 garage spots • Built 1988

Property at North River School Rd, Winterset, IA 50273

$4,938,450

Land451.34 acres (lot)

North River School Rd, Winterset, IA 50273

Property at 1524 260th St, Winterset, IA 50273, 3 beds, 2.5 baths

$949,900

Land15.86 acres (lot)

1524 260th St, Winterset, IA 50273

Property at 1509 State 92 Hwy, Winterset, IA 50273, 4 beds, 1 bath

$350,000

Land3.82 acres (lot)

1509 State 92 Hwy, Winterset, IA 50273

Property at 2318 Saint Charles Rd, Winterset, IA 50273, 3 beds, 2 baths

$900,000

Land18.78 acres (lot)

2318 Saint Charles Rd, Winterset, IA 50273

Property at 001 Rolling Green Ave, Winterset, IA 50273

$165,000

Land7.68 acres (lot)

001 Rolling Green Ave, Winterset, IA 50273

Property at 2039 145th Ln, Earlham, IA 50072

$740,000

Land55.42 acres (lot)

2039 145th Ln, Earlham, IA 50072

Property at 2444 Quail Ridge Ave, Saint Charles, IA 50240, 2 beds, 2 baths

$389,000

Land1.80 acres (lot)

2444 Quail Ridge Ave, Saint Charles, IA 50240

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

$414,900

Land3.00 acres (lot)

2607 Quail Ridge Trl, Winterset, IA 50273

Property at Lot 1 Buck Creek Ln, Earlham, IA 50072

$152,500

Land3.00 acres (lot)

Lot 1 Buck Creek Ln, Earlham, IA 50072

Property at Lot 2 Buck Creek Ln, Earlham, IA 50072

$152,500

Land3.00 acres (lot)

Lot 2 Buck Creek Ln, Earlham, IA 50072

Property at 1796 Millstream Ct, Winterset, IA 50273

$55,000

Land3.00 acres (lot)

1796 Millstream Ct, Winterset, IA 50273

Property at 002 220th St, Winterset, IA 50273

$140,000

Land5.36 acres (lot)

002 220th St, Winterset, IA 50273

Property at 36 Lot Covered Bridge Estates St, Winterset, IA 50273

$69,000

Land3.45 acres (lot)

36 Lot Covered Bridge Estates St, Winterset, IA 50273

Property at 2323 Cedar Bridge Rd, Winterset, IA 50273

$160,000

Land3.27 acres (lot)

2323 Cedar Bridge Rd, Winterset, IA 50273

Property at 2212 Deer Run Ave, Winterset, IA 50273

$260,000

Land10.23 acres (lot)

2212 Deer Run Ave, Winterset, IA 50273

Property at 2269 205th Ln, Winterset, IA 50273

$250,000

Land5.10 acres (lot)

2269 205th Ln, Winterset, IA 50273

Property at 2215 245th Ln, Winterset, IA 50273

$169,900

Land4.68 acres (lot)

2215 245th Ln, Winterset, IA 50273

Property at 2259 Cedar Bridge Rd, Winterset, IA 50273

$160,000

Land3.32 acres (lot)

2259 Cedar Bridge Rd, Winterset, IA 50273

Property at RR Scott Township, Winterset, IA 50222

$450,000

Land30.00 acres (lot)

RR Scott Township, Winterset, IA 50222

Property at 2368 St Charles Rd, Winterset, IA 50273

$175,000

Land7.14 acres (lot)

2368 St Charles Rd, Winterset, IA 50273

Property at Lot 3 4th Ave N, Winterset, IA 50273

$125,000

Land0.73 acre (lot)

Lot 3 4th Ave N, 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 Lot 1 4th Ave N, Winterset, IA 50273

$130,000

Land0.90 acre (lot)

Lot 1 4th Ave N, Winterset, IA 50273

Property at Lot 4 4th Ave N, Winterset, IA 50273

$185,000

Land1.42 acres (lot)

Lot 4 4th Ave N, Winterset, IA 50273

Property at Lot 5 4th Ave N, Winterset, IA 50273

$395,000

Land3.00 acres (lot)

Lot 5 4th Ave N, Winterset, IA 50273

Viewing page 2 of 2

Average home prices near Winterset, IA

Cities

Zip Codes

50273 homes for sale
$259,500

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)

$259,859

+17.3% YoY | Jun 2026

1 year
3 year
5 year

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

Location

Data

Jun 2026

Growth

% YoY

Winterset, IA

$259,859

+17.3%

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