Southwest Region, WI Land for Sale with Recently Sold Properties

Luxurious estate with panoramic views, world-class equestrian facilities, indoor arena, and fully licensed event venue—all crafted with custom finishes and comfort in mind.

Creekside Ranch

17595 Interior Rd., Tomah, WI, 54660, Monroe County

Land for sale in Monroe County, Wisconsin

VIDEOMAP

$5,950,00053.9 acres

Kyle Schultz

Trout Stream & Hunt Land WI

19920 State Hwy 56, Richland Center, WI, 53581, Richland County

Land for sale in Richland County, Wisconsin

$495,00079.5 acres

Versatile recreational land with tillable acreage, hardwood timber, and a Class I trout stream—perfect for hunting, fishing, farming, or building your dream retreat.

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

Under Contract

$625,00065.6 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

$1,050,000165 acres

Miess Road, Dodgeville, WI, 53533, Iowa County

Welcome to what may just be the best value recreational property on the market in all southern Wisconsin! Featuring the ultimate in seclusion and habitat surrounded by some of the most scenic landscape! Hidden at the end of a private gravel road, thi

Patrick Guyse

Whitetail Dreams Real Estate LLC

Land for sale in Grant County, Wisconsin

$2,900,000393 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

$725,00086 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

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

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

Sold

$535,00081.2 acres

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

Brian Ruesch

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

Sold Oct 4, 2024

$600,00092.6 acres

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

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

$920,000160 acres

Idle Lane, Wauzeka, WI, 53826, Crawford County

Kyle Schultz

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

Sold Jun 25, 2025

$234,90011.5 acres

1 beds1 baths688 sqft

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

Welcome to your secluded sanctuary in the heart of Wisconsins famed Driftless Regionan unglaciated landscape of deep valleys, steep ridges, and timeless beauty. Located between the charming communities of Viroqua and Readstown, this 26-acre wooded ha

Sold Aug 13, 2025

$249,90026 acres

S7454 U.S. 14, Readstown, WI, 54652, Vernon County

Joe Nawrot

Welcome to your ultimate recreational retreat located in the heart of Richland County, Wisconsin. This remarkable 100-acre property may be found at the scenic intersection of Sawmill Road and County HWY TB. Embrace an unparalleled opportunity to own

VIDEOMAP

$250,000100 acres

County Highway Tb, Richland Center, WI, 53581, Richland County

This beautiful Crawford County farm on Happy Place Lane (dead-end road) could be the culmination of your hunting land search. With 85+/- tillable acres and 122+/- wooded acres, it is a nearly ideal mix of hunting opportunities and income. The uninter

$1,727,800212 acres

43803 Happy Place Lane, Gays Mills, WI, 54631, Crawford County

The sellers call this Richland County farm, Field of Dreams; I call it very unique. After all, where can you leave 344+/- acres of hunting and recreation, and 5 minutes later be sitting at one of a half dozen restaurants? And for those that want othe

Sold May 9, 2024

$2,150,000344 acres

5 beds1 baths2,400 sqft

25994 Arnell Drive, Richland Center, WI, 53581, Richland 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 Rd, Hillsboro, WI, 54634, Vernon County

Joe Nawrot

VIDEOMAP

$335,00050.9 acres

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

Welcome to one of Wisconsins most unique and picturesque country estatesan extraordinary 28.24-acre retreat located in the Baraboo Bluffs of Sauk County. This breathtaking property blends luxurious rural living with unforgettable natural beauty, incl

VIDEOMAP

$675,00028.2 acres

4 beds3 baths2,352 sqft

E13019 Fairfield Road, Baraboo, WI, 53913, Sauk County

If you’ve been looking for a private setting in the Driftless Area to build your dream home, raise livestock, and have some incredible hunting opportunities, then you need to look at this new listing! This 120 acres +/- in Southeast Monroe County, Wi

VIDEOMAP

$918,000120 acres

000 Outfield Road, Elroy, WI, 53929, Monroe County

Kyle Schultz

Here’s your chance to own a truly rare legacy property spanning 277.38+/- surveyed acres in both Green and Iowa Counties, just outside Hollandale, WI. This is a wonderfully secluded location and one of a dwindling number of '275-acre-plus' properties

VIDEOMAP

$3,150,000277 acres

5 beds2 baths2,500 sqft

8991 Mckenzie Lane, Hollandale, WI, 53544, Iowa County

Alden Tinder