Iowa, WI Homes

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  /27

  $224,900

  • 3 Beds
  • 1 Bath
  • 2,100 Sq Ft

  916 Diagonal St, Highland, WI 53543

  Welcome to your new happy place in the heart of Highland! This adorable 3-bedroom home is full of charm and ready for its next chapter. Picture yourself sipping coffee on the porch, then heading inside to a warm, inviting space that feels like home from the moment you walk in. The one-car garage keeps life simple, and the brand-new fenced yard is perfect for four-legged friends, backyard games,

  Emily Lins RE/MAX Preferred

  916 Diagonal St, Highland, WI 53543
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  /32

  $147,000 Sold Jul 14, 2025

  • 1,504 Sq Ft
  • $98/SF
  • 8 Days On Market

  • 4 Beds
  • 1.5 Baths

  604 Isabell St, Highland, WI 53543

  If you're looking for a place to call home, this 4-bedroom, 1.5-bath house on a corner lot is ready for you! Step into the cozy living room with beautiful newly refinished wood floor, perfect for relaxing after a long day. The eat-in kitchen offers lots of cabinet space - great for cooking, baking, & gathering with family or friends. With 2 bedrooms on the main floor & 2 more upstairs, there’s

  Heather McNeill Lori Droessler Real Estate, In

  604 Isabell St, Highland, WI 53543
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  /8

  Est $215,440 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,358 Sq Ft

  5074 County Road Q, Highland, WI 53543

  5074 County Road Q, Highland, WI 53543
• 

  

  

  /14

  $44,900

  • Land
  • 10 Acres
  • $4,490 per Acre

  0000 19th Ave E, Highland, WI 54849

  Very nice 10 acre parcel ideal for your residential home or a recreational cabin, camping, etc. Just a few miles to the Brule River State Forest and Stone's Bridge Landing to access the famous Bois Brule River. Property is heavily wooded in hardwoods and an easement road is in place and meanders thru the West side of property. Use easement to access, or create your own driveway access right off

  Sara Haakenson Re/Max 4 Seasons, LLC

  0000 19th Ave E, Highland, WI 54849
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  /44

  $203,000 Sold Jul 11, 2025

  • 1,700 Sq Ft
  • $119/SF
  • 3 Days On Market

  • Built 1996

  207 Dodgeville St, Highland, WI 53543

  BACK ON THE MARKET! Move-In Ready Duplex on 1/2 Acre with Big Sky & Country Views. Don’t miss this great investment opportunity just minutes from downtown Highland! This well-maintained duplex sits on a spacious half-acre lot and offers beautiful open views and convenient access to main roads. Property Highlights: Two Units — each with a main level bathroom and laundry. Full basement for ample

  Kathi Schmidt Keller Williams Realty

  207 Dodgeville St, Highland, WI 53543
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  /55

  Est $746,373 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft

  5555 Farmers Ridge Rd, Highland, WI 53543

  5555 Farmers Ridge Rd, Highland, WI 53543
• 

  

  /33

  $206,000

  • 7 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  535 Spring St, Highland, WI 53543

  Showings begin again - 6/28/25. Extra large home in the Village of Highland Wisconsin. For the buyer looking for a place for lots of family or friends, with 7 bedrooms and 3+ bathrooms there's plenty of room. Wrap around decks, large lot, 2 car garage, lots of additional off street parking. The basement offers potential for even more usable space. Easily merged into 1 unit by opening a few locked

  Brady Conner Wisconsin.Properties Realty, LLC

  535 Spring St, Highland, WI 53543
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  /6

  $262,600 Sold Jun 24, 2025

  • 1,500 Sq Ft
  • $175/SF
  • 0 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1968

  342 Grand St, Highland, WI 53543

  Ranch home with 4 bedrooms, large kitchen, full basement, and large lot. Updates include newer bathroom, flooring, trim and doors throughout. This home is ready to be enjoyed!

  Bobbi Jo Bomkamp Drone Century 21 Affiliated

  342 Grand St, Highland, WI 53543
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  /27

  Est $289,080 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft

  1787 Pompeys Pillar Rd, Highland, WI 53543

  1787 Pompeys Pillar Rd, Highland, WI 53543
• 

  

  /13

  $259,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  1370 Dodgeville St, Highland, WI 53543

  Introducing a fantastic opportunity! This two-story, three-bedroom, one-and-a-half-bath home is ready for you! The main floor has an open kitchen, dining area, living room, full bath, and laundry/office space. The upper level consists of three bedrooms and a bathroom. Key features include a new metal roof, two-car attached garage, and full basement. Situated on the edge of town on .37 acres, this

  Bobbi Jo Bomkamp Drone Century 21 Affiliated

  1370 Dodgeville St, Highland, WI 53543
• 

  

  /15

  $145,000 Sold May 07, 2025

  • 1,760 Sq Ft
  • $82/SF
  • 134 Days On Market

  • 4 Beds
  • 1.5 Baths

  1231 Dodgeville St, Highland, WI 53543

  Welcome to this charming 2-story home featuring 4 bedrooms, large living room and spacious dine in kitchen offering great entertaining spaces. Main floor laundry is a bonus! Located only a few blocks away from the park. This home is being sold "As Is" Parcel Id's 136-0277 and 136-0275

  Tammy McGuire McGuire Realty Group, LLC

  1231 Dodgeville St, Highland, WI 53543
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  /15

  Est $172,360 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft

  1111 Dodgeville St, Highland, WI 53543

  1111 Dodgeville St, Highland, WI 53543
• 

  

  /37

  $499,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,160 Sq Ft

  110 Grand St, Highland, WI 53543

  Offer with a Bump 7/1Newer 3 bedroom ranch style home located on a dead end street. This home offers an open concept that gives you the warm welcoming vibe. As you enter the home you will find a several windows that over look the deck. A large island that is great for entertaining. The stone gas fireplace is an elegant touch to the living room. Master bedroom offers a walk in closet, large

  Michelene Fisher Fisher Realty Group, LLC

  110 Grand St, Highland, WI 53543
• 

  

  /22

  $160,000 Sold Apr 07, 2025

  • 1,220 Sq Ft
  • $131/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths

  530 Delaney St, Highland, WI 53543

  Welcome home to this 3 bedroom 1.5 bath cozy two story home. As you enter the home you will find an updated entry way with new flooring, trim, and ceiling. Large kitchen that walks out to a decent size deck along with a fenced in yard. Laundry is located on the main floor. Second level offers 3 bedrooms and an updated half bath with new electrical and plumbing. Sq.Ftg. is approximate. Buyer to

  Michelene Fisher Fisher Realty Group, LLC

  530 Delaney St, Highland, WI 53543
• 

  

  /18

  Est $268,361 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,480 Sq Ft

  1270 Dodgeville St, Highland, WI 53543

  1270 Dodgeville St, Highland, WI 53543
• 

  

  /42

  $395,000 Sold Dec 20, 2024

  • 2,904 Sq Ft
  • $136/SF
  • 193 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1996

  1280 Smokey Hollow Rd, Highland, WI 53543

  Come check out this private country homestead set on 5 Acres in Southwest Wisconsin. Spacious, 4 Bed, 2 bath home with open layout and vaulted ceilings . A very large deck over looks this very peaceful land. There is a 1 car attached garage and a 30x36 insulated shed/shop with an attached open lean for extra storage. A huge yard, great garden area, rock outcroppings, woods and a creek all add to

  Ed Kraisinger RE/MAX Preferred

  1280 Smokey Hollow Rd, Highland, WI 53543
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  /6

  Est $160,156 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,200 Sq Ft

  606 Dodgeville St, Highland, WI 53543

  606 Dodgeville St, Highland, WI 53543
• 

  

  /77

  $612,000 Sold Dec 10, 2024

  • 2,924 Sq Ft
  • $209/SF
  • 98 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1900

  4669 State Road 80, Highland, WI 53543

  Discover your dream farmette! This lovingly renovated home (2005) features an open kitchen, dining, and sitting room with scenic views, plus a spacious living room. Custom laundry and mudroom connect to the garage and basement, simplifying country living. With 2 bedrooms on the main level, 2 upstairs, and an office, it's perfect for any family. The barn is exceptional, suitable for cows, goats,

  Christina Weitzel RE/MAX Preferred

  4669 State Road 80, Highland, WI 53543
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  /32

  Est $198,943 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,095 Sq Ft

  517 High St, Highland, WI 53543

  517 High St, Highland, WI 53543
• 

  

  /46

  $749,900 Sold Nov 15, 2024

  • Land
  • 87 Acres
  • $8,610 per Acre

  • 356 Days On Market

  1630 County Road I, Highland, WI 53543

  Your private amazing paradise awaits you. This 87+/- acres of mature trees, rolling hills and open spaces, located in the breathtaking Driftless Region of Southwest WI. Available for the first time in 33 years. It's a once in a lifetime opportunity to build your dream home in this truly incredible country setting. You'll find large timbers, Oaks, Rock outcroppings and Bluffs. Wildlife, deer,

  Pat Keegan Driftless Area LLC

  1630 County Road I, Highland, WI 53543
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  /24

  Est $185,937 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  511 Dodgeville St, Highland, WI 53543

  511 Dodgeville St, Highland, WI 53543
• 

  

  /27

  $186,000 Sold Oct 31, 2024

  • 1,288 Sq Ft
  • $144/SF
  • 20 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1967

  242 Dodgeville St, Highland, WI 53543

  Charming ranch-style home located in the heart of Highland! This well-maintained property boasts numerous recent updates, including a brand-new HVAC system installed within the past year, along with a newly replaced roof and windows for added peace of mind. Enjoy the expansive backyard, perfect for outdoor entertaining, gardening, or simply relaxing. Whether you're a first-time homebuyer or

  Joe VanMatre EXP Realty, LLC

  242 Dodgeville St, Highland, WI 53543
• 

  

  /67

  Est $178,148 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,123 Sq Ft

  344 Isabell St, Highland, WI 53543

  344 Isabell St, Highland, WI 53543
• 

  

  /21

  $185,900 Sold Oct 30, 2024

  • 1,884 Sq Ft
  • $99/SF
  • 9 Days On Market

  • 5 Beds
  • 1 Bath

  504 Spring St, Highland, WI 53543

  This beautifully maintained Craftsmen-style home boasts timeless charm and character throughout. Enjoy the updated kitchen, complete with stunning hickory cabinets, and a dining room featuring a handcrafted hutch, perfect for family gatherings. This home is filled with abundant natural light, highlighting the original woodwork that adds to it's warm ambiance. Modern convivences include central

  Jacqueline Benish First Weber Inc

  504 Spring St, Highland, WI 53543
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  /35

  Est $216,612 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft

  515 Spring St, Highland, WI 53543

  515 Spring St, Highland, WI 53543
• 

  

  /23

  $139,900 Sold Sep 30, 2024

  • 1,224 Sq Ft
  • $114/SF
  • 17 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1962

  506 Dodgeville St, Highland, WI 53543

  Welcome to Highland, a charming village in the Driftless region with stunning views in every direction. This inviting ranch-style home features 2 spacious bedrooms with hardwood floors and large closets, plus a beautifully remodeled bathroom with a deep soaking tub. Enjoy convenient first-floor laundry and an open-concept living area combining the kitchen, dining, and living spaces. The attached

  Risa Topper Realty of America, LLC

  506 Dodgeville St, Highland, WI 53543
• 

  

  /24

  Est $205,264 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  314 Spring St, Highland, WI 53543

  314 Spring St, Highland, WI 53543
• 

  

  /22

  $150,000 Sold Aug 30, 2024

  • 1,200 Sq Ft
  • $125/SF
  • 153 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  316 Main St, Highland, WI 53543

  Small town living in this nice 3 bedroom 1 bath home in Highland, Wisconsin. The home has a new basement foundation with one car garage, newer electric, plumbing, spray foam insulation, and there is even plumbing ready for a new bathroom in the basement. The kitchen and bathroom have both been remodeled, there are new cabinets and newer appliances stay with the home. Tons of potential with this

  Ed Kraisinger RE/MAX Preferred

  316 Main St, Highland, WI 53543
• 

  

  /15

  Est $159,528 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  608 Spring St, Highland, WI 53543

  608 Spring St, Highland, WI 53543
• 

  /2

  $245,000 Sold Jun 13, 2025

  • 1,900 Sq Ft
  • $129/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  1045 E Circle Dr, Highland, WI 53543

  Sold under single party listing.

  MHB Real Estate Team MHB Real Estate

  1045 E Circle Dr, Highland, WI 53543
• 

  

  /50

  Est $347,238 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  539 Prospect St, Highland, WI 53543

  539 Prospect St, Highland, WI 53543
• 

  /2

  $260,000 Sold Aug 01, 2025

  • 1,568 Sq Ft
  • $166/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths

  744 Main St, Highland, WI 53543

  Michelene Fisher Fisher Realty Group, LLC

  744 Main St, Highland, WI 53543
• 

  

  /32

  Est $228,970 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft

  515 Stone St, Highland, WI 53543

  515 Stone St, Highland, WI 53543
• 

  

  /28

  Est $187,449 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  520 Stone St, Highland, WI 53543

  520 Stone St, Highland, WI 53543
• 

  

  /14

  Est $187,301 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  915 Dodgeville St, Highland, WI 53543

  915 Dodgeville St, Highland, WI 53543
• 

  

  /21

  Est $160,756 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,176 Sq Ft

  518 Main St, Highland, WI 53543

  518 Main St, Highland, WI 53543
• 

  Est $166,746 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  522 Main St, Highland, WI 53543

  522 Main St, Highland, WI 53543
• 

  

  /21

  Est $236,493 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  6216 County Road Pp, Highland, WI 53543

  6216 County Road Pp, Highland, WI 53543
• 

  

  /82

  Est $509,849 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 2,561 Sq Ft

  2543 Adams Hill Rd, Highland, WI 53543

  2543 Adams Hill Rd, Highland, WI 53543
• 

  

  /59

  Est $501,260 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,420 Sq Ft

  1212 Harms Rd, Highland, WI 53543

  1212 Harms Rd, Highland, WI 53543

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