Southwest Region, WI Timberland Properties, Undeveloped 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

Timberland Property for sale in Monroe County, Wisconsin

MAP

$5,950,00053.9 acres

Kyle Schultz

Whitetail Properties Real Estate

Richland County Acreage

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

Timberland Property for sale in Richland County, Wisconsin

VIDEOMAP

$1,945,000106 acres

5 beds4 baths6,290 sqft

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

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

Timberland Property for sale in Sauk County, Wisconsin

$665,00065.6 acres

Aaron Dobbs

Weiss Realty LLC

Dane County Acreage

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

Timberland Property for sale in Dane County, Wisconsin

$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

Timberland Property 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

Timberland Property 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

Timberland Property 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

Timberland Property in Iowa County, Wisconsin

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

Timberland Property in Juneau County, Wisconsin

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

Whitetail Properties Real Estate

Timberland Property in Crawford County, Wisconsin

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

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

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

Timberland Property in Richland County, Wisconsin

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

Timberland Property in Vernon County, Wisconsin

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

Timberland Property for sale in Vernon County, Wisconsin

VIDEOMAP

$335,00050.9 acres

S4708 Muncie Road, Hillsboro, WI, 54634, Vernon 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

VIDEOMAP

$335,00050.9 acres

S4708 Muncie Rd, Hillsboro, WI, 54634, Vernon 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

VIDEOMAP

$249,90026 acres

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

Youre looking at one of the most decorated Gentlemen Estates to hit the market in the Midwestern United States. This private 552+/- acre masterpiece lies in the heart of Richland County set amidst an unspoiled landscape teeming with cascading bluffs,

Sold Mar 17, 2021

$3,100,000552 acres

6 beds4 baths5,525 sqft

Snow Valley Road, Richland Center, WI, 53581, Richland County

This rare, large-acreage parcel presents a strategic acquisition opportunity for commercial developers, institutional investors, and specialized operators in energy, tech infrastructure, and industrial storage. Bordering both the City of Portage and

Timberland Property for sale in Columbia County, Wisconsin

VIDEOMAP

$599,90024.2 acres

N7558 Boeck Road, Portage, WI, 53901, Columbia County

Travis Hamele

If you’ve been searching for an impressive hunting property here in the Driftless Area, you have to take a look at this new listing! If you enjoy deer and turkey hunting with beautiful hardwood ridges, you are going to love this place. While taking p

VIDEOMAP

$1,550,000207 acres

000 Byrds Creek Valley Dr., Blue River, WI, 53518, Richland County

Kyle Schultz

Whitetail Properties Real Estate

Sold Mar 17, 2021

$3,100,000552 acres

6 beds4 baths5,525 sqft

Snow Valley Road, Richland Center, WI, 53581, Richland County