12

Recently Sold Highland, WI Homes

Section Image
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /13

    $67,900 Sold Jul 12, 2024

    • Land
    • 1.21 Acres
    • $56,116 per Acre
    • 113 Days On Market

    Lot 4 Steinhilpert Dr, Highland, WI 54873

    Situated on 1.21 acres and 159 feet of shoreline, this Catherine Lake Lot offers an ideal canvas for future development. This lot provides an easy access to this 70-acre lake. Per the DNR it holds panfish and largemouth bass. With mature trees for privacy, it can be your peaceful retreat, while still within reach of all the recreational opportunities and attractions that Douglas County has to

    Kevin Brisky Lakewoods Real Estate

    Lot 4 Steinhilpert Dr, Highland, WI 54873
  • /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
How to Buy a Home How to Sell a Home How to Rent a Home