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

MAP

$5,950,00053.9 acres

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

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$970,000139 acres

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

Patrick Guyse

Whitetail Dreams Real Estate LLC

MAP

$550,00063.9 acres

Altman Rd, Orfordville, WI, 53576, Rock County

Opportunity knocks in Rock County with this turnkey 63.93+/- acre parcel on Altman Road in Orfordville, WI. Located on a quiet dead-end road, this diverse property offers everything a land buyer could wantprime whitetail and turkey hunting, income-pr

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

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

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

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

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$1,050,000165 acres

Miess Road, Dodgeville, WI, 53533, Iowa County

Patrick Guyse

Whitetail Dreams Real Estate LLC

MAP

$450,0005 acres

5 beds2 baths2,608 sqft

14821 W Altman Rd, Orfordville, WI, 53576, Rock County

Welcome to a one-of-a-kind opportunity in Rock County at 14821 W Altman Rd, Orfordville. This secluded country property on 5 acres offers both privacy and proximity, located on a quiet dead-end road just minutes from town with quick access to Highway

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

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$425,0004.8 acres

3 beds2 baths2,170 sqft

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

If you’ve been looking to escape to the country and raise some animals, then you need to take a look at this new listing! This would be the perfect place to raise livestock and create the self-sustainable life you’ve always wanted. The log home on th

Land for sale in Grant County, Wisconsin

MAP

$655,00013.6 acres

14226 Birds Eye Rd, Fennimore, WI, 53809, Grant 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

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$335,00050.9 acres

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

Looking to get away from the city and enjoy some peace and quiet? This beautiful country home sits nearly mile off the county road, tucked behind mature pines and mature wooded ridges for complete privacy and a true sense of seclusion. The home itsel

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$789,00089.5 acres

3824 County Hwy E, Warrens, WI, 54666, Monroe County

Escape to the serene solitude of Wisconsins Driftless Region with this rustic 12-acre woodland getaway tucked into the bluff country of Crawford County. Located just minutes from Boscobel and the Wisconsin River, this secluded sanctuary offers the pe

Land for sale in Crawford County, Wisconsin

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$135,00012 acres

29855 Clear Creek Road, Boscobel, WI, 53805, Crawford County

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

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$529,00072 acres

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

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$335,00050.9 acres

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

Sold Mar 17, 2021

$3,100,000552 acres

6 beds4 baths5,525 sqft

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

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$249,90026 acres

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

Are you in search of a recreational property in Southwest Wisconsin that is unparalleled to any deer hunting land that youve ever seen? This veritable trophy whitetail kingdom consisting of 112.70-acres in Steuben, Wisconsin spotlights a catalog of m

Sold Apr 12, 2023

$598,500113 acres

24745 Heisz Road, Steuben, WI, 54657, Crawford County

Located in the heart of Southwest Wisconsins Driftless Region, this 11-acre Amish homestead offers an extraordinary opportunity for those seeking a serene lifestyle surrounded by natures splendor. Whether you envision it as a hobby farm or countrysid

Sold Jul 23, 2025

$399,90011 acres

3 beds1 baths

27325 Munz Drive, Lone Rock, WI, 53556, Richland County

Whitetail Properties Real Estate is proud to bring to market this exceptional and highly sought-after 108.57-acre tract in scenic Lafayette County, WI. This diverse landscape offers a rare combination of investment potential and recreational appeal.A

Land for sale in Lafayette County, Wisconsin

MAP

$1,398,500109 acres

County Rd N, Blanchardville, WI, 53516, Lafayette County

Youre looking at one of the most decorated Legacy Farms for sale in Southwest Wisconsin sprawled across an extraordinary 139.73-acres. This ever-secluded dead-end road farm spans across a breathtaking ridgetop between Boscobel and Gays Mills set amid

Sold Jul 5, 2023

$1,085,000140 acres

3 beds1 baths1,900 sqft

20990 Apple Ridge Lane, Gays Mills, WI, 54631, Crawford County

Youre looking at a stunning ridgetop country home settled upon some of the very best deer hunting in the region. This rural wonderland is your gateway to a sprawling 92+/- acres in the very heart of the Driftless Region. This estate is settled upon a

Sold Jan 6, 2023

$924,90092.1 acres

4 beds3 baths4,200 sqft

16195 Coy Lane, Viola, WI, 54664, Richland County