Southwest Region, WI Land for Sale with Recently Sold Properties

Legacy Farm in Driftless WI

4850 County Highway H, Ridgeway, WI, 53582, Iowa County

MAP

$2,200,000306 acres

2 beds2 baths

Historic farm with productive ag land, trout stream frontage, mature hardwoods, and two rental homes—offering income, recreation, and rich heritage.

Unparalleled private estate in Wisconsin's scenic Richland County offers luxurious rural living and exceptional hunting.

Richland County Acreage

31361 Oakridge Drive, Muscoda, WI, 53573, Richland County

Land for sale in Richland County, Wisconsin

VIDEOMAP

$1,945,000106 acres

5 beds4 baths6,290 sqft

Exceptional 65+ acre parcel near Spring Green offers privacy, natural beauty, and convenience in the renowned Driftless Area.

Sauk County Acreage

Paulus Road, Spring Green, WI, 53588, Sauk County

$665,00065.6 acres

Aaron Dobbs

Weiss Realty LLC

Dane County Acreage

+/-236 Ac Old Stone Road, Stoughton, WI, 53575, Dane County

$3,500,000236 acres

Versatile land offering productive tillable acreage, lakefront development potential, and abundant recreation, near protected green space and a major city.

Alex Weber

Wildland Properties

VIDEOMAP

$970,000139 acres

30084 Overbrook Avenue, Elroy, WI, 53929, Monroe County

Set along a quiet dead-end road on the Monroe and Vernon County line, this 139.37 acre picturesque farm offers a Driftless Region landscape featuring multiple access points, multiple potential building sites, tillable ground, food plots, diverse age

Patrick Guyse

Whitetail Dreams Real Estate LLC

Land for sale in Grant County, Wisconsin

$3,500,000393 acres

16884 County Road S, Boscobel, WI, 53805, Grant County

Discover a rare opportunity to own this incredible 392.61-acre farm, perfectly situated in a peaceful valley setting just minutes from town. This expansive property features a farmhouse, a spacious machine shed, and multiple additional storage buildi

Garrick Olerud

NextHome Prime Real Estate

$4,275,000340 acres

2 beds2 baths1,951 sqft

8580 Roelke Road, Blue Mounds, WI, 53517, Iowa County

Pristine 340 Acres located in Iowa County Wisconsin. Potential for 4 Homesites! This property has it all! Abundant Wildlife, Trophy Whitetail Deer (Q.D.M) implemented since 1995! Food plots, thick bedding, water holes, & timber. 100.78 Cropland lease

Kelly Gilboy

Restaino & Associates

Land for sale in Crawford County, Wisconsin

$779,00086 acres

86 Ac County Road S, Gays Mills, WI, 54631, Crawford County

Nestled in the heart of the Driftless area of Crawford County, Wisconsin, this 86-acre property has it all. This is as turn-key a hunting property as you can get. 2 Redneck Blinds and 7 Millennium Ladder stands go with the property. Professionally ma

Ashley Straka

Century 21 Affiliated

Land for sale in Green County, Wisconsin

$2,231,250213 acres

212 Acres County Road H, Blanchardville, WI, 53516, Green County

Over 200 acres of contiguous land with 185 tillable acres. The land is under contract for rent for the 2025 season. Previous seller indicated a well on site. Huntsville and Dodgeville Silt Loam soil. Almost all of this land is tillable and profitable

Melodie Hawkins

EXIT Professional Real Estate

Sold Jun 15, 2024

$699,00040.4 acres

5555 Farmers Ridge Road, Highland, WI, 53543, Iowa County

From the time you roll down the drive into this 40.4+/- acre property just north of Highland, youll feel like youre in a special place. With 23+/- acres of woods, 5.25+/- acres of pasture and about 5 acres of tillable ground, it is a great mix for mu

Jay Frazier

Weiss Realty

Sold

$535,00081.2 acres

N6199 Cty Rd H, Camp Douglas, WI, 54618, Juneau County

Grab this piece while you have the chance! Not many properties in this area come available! Discover the perfect blend of natural beauty, recreation, and investment potential with this exceptional property located in Wisconsin’s coveted Driftless Reg

Brian Ruesch

Located at the end of a dead-end lane, you will find one of the best hunting properties that Southwest Wisconsin has to offer. With a long history of great bucks on the property, you won’t want to miss out on this one. At the center of the property i

Sold Nov 9, 2022

$920,000160 acres

Idle Lane, Wauzeka, WI, 53826, Crawford County

Kyle Schultz

Hidden at the end of a private gravel road, this 165-acre peaceful outdoor paradise offers quality hunting for whitetails and turkey, trout fishing in a Class II stream, or simply enjoying time with the family! It features 36 acres of CRP generating

VIDEOMAP

$1,050,000165 acres

Miess Road, Dodgeville, WI, 53533, Iowa County

Patrick Guyse

Whitetail Dreams Real Estate LLC

Sold Jun 25, 2025

$234,90011.5 acres

1 beds1 baths688 sqft

64986 Howath Road, De Soto, WI, 54624, Crawford County

Tucked high above the Mississippi River Valley at an elevation of 1,120 feet lies a truly enchanting cabin retreat that captures the very spirit of Wisconsins Driftless Region. Located in Crawford County, just outside the historic river town of DeSot

Nestled in the emerald hills of Sauk County, Wisconsin, this enchanting country home offers 4.8-acres of country living surrounded by towering hardwoods, pristine landscaping, and the tranquil sounds of nature. Whether youre seeking a private year-ro

VIDEOMAP

$425,0004.8 acres

3 beds2 baths2,170 sqft

E4377 Dawn Road, Plain, WI, 53577, Sauk County

Welcome to one of the most premier recreational tracts for sale in Southwest Wisconsinan immaculate 50.90-acre haven nestled in the rolling ridges of Vernon County just minutes outside Hillsboro. This rare slice of paradise is located in a region cel

Land for sale in Vernon County, Wisconsin

VIDEOMAP

$335,00050.9 acres

S4708 Muncie Road, Hillsboro, WI, 54634, Vernon County

VIDEOMAP

$335,00050.9 acres

S4708 Muncie Rd, Hillsboro, WI, 54634, Vernon County

Joe Nawrot

If youve ever dreamed of owning a manageable-yet-mighty slice of Driftless bluff countrywhere world-class trout water meets trophy deer habitatthis 34+/- acre recreational property near Viola, WI deserves your full attention. Set in the rugged folds

VIDEOMAP

$285,00034 acres

Elk Creek Rd, Viola, WI, 54664, Richland County

VIDEOMAP

$285,00034 acres

Elk Creek Rd, Viola, WI, 54664, Richland County

Joe Nawrot

Here is a rare opportunity to own your own estate at the end of a dead-end road, with a view of true Driftless Area beauty in each direction. Richland County ranks high as a recreational destination and this property leaves little to be desired. The

Sold Oct 4, 2024

$1,449,000197 acres

2 beds2 baths1,560 sqft

26275 Homestead Lane, Blue River, WI, 53518, Richland County

Jay Frazier

Weiss Realty

Sold Oct 4, 2024

$600,00092.6 acres

S5505 County Road N, Viroqua, WI, 54665, Vernon County

Check out this 92.6 +/- acre recreational parcel in the heart of Vernon Countys big buck country. Its conveniently located 15 minutes from the eclectic town of Viroqua, and also 15 minutes from recreational opportunities on the Mississippi River. The

Jay Frazier

Weiss Realty

VIDEOMAP

$1,620,000217 acres

2 beds1 baths1,568 sqft

18125 County Highway I, Hillsboro, WI, 54634, Richland County

Located deep in Wisconsins famed Driftless Region, this 217-acre hunting sanctuary in Richland County is a rare opportunity for serious whitetail and wildlife enthusiasts. This property has been a proven producer of trophy-class bucks year after year

Travis Hamele

Alden Tinder of Whitetail Properties Real Estate is honored to represent this opportunity to own a piece of the coveted driftless region south of Avoca, Wisconsin. This property combines field land and mixed hardwood forest, with a small stream runni

VIDEOMAP

$529,00072 acres

6833 State Rd 80, Avoca, WI, 53506, Iowa County

Alden Tinder

Among the idyllic rolling hills between Dodgeville and Mount Horeb and located 5-miles north of Ridgeway, WI lies one of Southwest Wisconsins most remarkable and storied propertiesa historic 306+/- acre farm that offers far more than fertile ground.

MAP

$2,200,000306 acres

4850 County Highway H, Ridgeway, WI, 53582, Iowa County

Joe Nawrot