Southwest Region, WI Land for Sale

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

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$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.

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

Dane County Acreage

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

$3,500,000236 acres

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

VIDEOMAP

$250,000100 acres

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

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

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

Jay Frazier

Weiss Realty

Land for sale in Vernon County, Wisconsin

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$335,00050.9 acres

S4708 Muncie Rd, 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

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$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

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$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

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$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

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$3,150,000277 acres

5 beds2 baths2,500 sqft

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

Alden Tinder

Set along a quiet dead-end road on the Monroe and Vernon County line, this 80 acre picturesque farm offers a Driftless Region landscape featuring direct access, multiple potential building sites, tillable ground, diverse age classes of timber, and a

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$548,00080 acres

Overbrook Avenue, Elroy, WI, 53929, Monroe County

Patrick Guyse

Whitetail Dreams Real Estate LLC

VIDEOMAP

$411,00059.4 acres

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

Set along a quiet dead-end road on the Monroe and Vernon County line, this 59.37 acre picturesque farm offers a Driftless Region landscape featuring multiple access points, multiple potential building sites, tillable ground, food plots, diverse age c

Patrick Guyse

Whitetail Dreams Real Estate LLC

VIDEOMAP

$385,00058 acres

Berry Hill Drive, Richland Center, WI, 53581, Richland County

Recreational Paradise & Trophy Whitetail Hunting Haven in Southwest Wisconsin Discover 58+/- acres of pristine recreational and hunting land lying in the heart of trophy whitetail country, off Berry Hill Road in Richland Center. This rare piece of de

LOCATION Grant County, Wisconsin This tillable land is located 6.9 miles south of Lancaster, Wisconsin, 16 miles west of Platteville, Wisconsin, and 27 miles north of Dubuque, Iowa. The farm is further described as being located in Section 4, 3N-3W,

Auction115 acres

Lancaster, WI, 53813, Grant County

Sullivan Auctioneers

Land for sale in Juneau County, Wisconsin

MAP

$449,90030 acres

4 beds2 baths2,093 sqft

W10130 Powers Road, Elroy, WI, 53929, Juneau County

Welcome to one of the most enchanting hobby farms in Southwest Wisconsinan idyllic 30-acre country retreat located in the heart of Juneau County, just outside the quaint town of Elroy. Set amidst a storybook landscape of rolling bluffs, deep valleys,

Whitetail Properties Real Estate is honored to present this amazing 104 +/- acre property that offers breathtaking views, ideal for your dream home. Multiple advantageous building site locations capitalize on mesmerizing views. The expansive acreage

MAP

$1,248,000104 acres

Fesenfeld Rd, Black Earth, WI, 53515, Dane County

Alden Tinder

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

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$135,00012 acres

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

Dream Retreat for Sale in Richland County, Wisconsin Priced Below Appraised Value! Are you in search of the perfect Southwest Wisconsin deer hunting camp or a tranquil countryside escape? This incredible 40-acre recreational property in Richland Coun

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$574,90040 acres

2 beds2 baths2,600 sqft

13504 Jungle Bar Lane, Cazenovia, WI, 53924, Richland County

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$250,000100 acres

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