Highland, WI homes for sale & real estate

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ABOUT THIS HOME
Highland, WI Homes for Sale
Terrific downtown location. If you want your own place, but want some help to pay for it, look at this opportunity to live in one unit and let your renter help with the payments. Currently, used as an air bnb. Last year, the income was $16,000. The first floor is completely done and ready for you to live there or rent out?either short or long term. The upstairs is a blank slate. Use your sweat equity and finish it to your specifications. The HVAC for both units is new, all the appliances on the main level are newer as are many windows. From top to bottom, ie roof to foundation, many major elements have been updated. See the long list of updates in documents.

$150,000

2 beds2 baths— sq ft

522 Main St, Highland, WI 53543

New hvac • Newer appliances • Downtown location

Torre Pustina • The Professional Brokers

ABOUT THIS HOME
Highland, WI Homes for Sale
Offer w/ bump 08/12/2025. 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, or stargazing nights. Love small-town life? You?ll be steps from shops, parks, and everything Highland has to offer. Come see it?you?ll fall in love!

$209,995

3 beds1 bath2,100 sq ft

916 Diagonal St, Highland, WI 53543

One-car garage • Fenced yard • Steps from shops

Emily Lins • RE/MAX Preferred

ABOUT THIS HOME
Highland, WI Homes for Sale
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 bathroom with a double sink vanity and a private toilet. Enjoy the wrap around porch with a view that will make you feel like you're in the country. The basement walks out to the backyard, has two bedrooms, full bath, fireplace and plenty of room to hang out or entertain. Let's not forget about the 3 car

$499,900

3 beds2.5 baths3,160 sq ft

110 Grand St, Highland, WI 53543

Wrap around porch • Open concept • Stone gas fireplace

Michelene Fisher • Fisher Realty Group, LLC

ABOUT THIS HOME
Highland, WI Homes for Sale
BIG VIEWS, improved property, and a BEAUTIFUL place in the country! Seller bought this 68 acre property a few years ago, loved it, improved it, but life happened and he needs to move on - TAKE ADVANTAGE! The hard work is done - Seller cleaned up debris, cut new trails, cleaned up logging roads, added multiple food plots, enrolled the property in MFL, increased the amount of tillable acreage, and had a soil test for a septic, now you can enjoy it! This property is PRIME TIME with tons of deer and turkey and BIG VIEWS across the valley. Admire the beautiful older growth timber scattered throughout the property! Seller planned to build a cabin and keep this property for years, now its YOUR CHA

$524,900

— beds— baths— sq ft

445 Busch Rd, Highland, WI 53543

68 acre property • Soil test for septic • 68.8 acre lot

Tyler Wilkinson • Wilkinson Auction & Realty Co.

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ABOUT THIS HOME
Highland, WI Homes for Sale
Brand new ranch style condo with brand new appliances. Over 1,800 sq ft living space on the main level. Full unfinished basement. Stubbed for bathroom, walls in basement studded for 2 more bedrooms and a big family rec room. This would double your living space. Spacious 2 car garage. Open floor plan. Big roomy kitchen with lots of cupboards and counter top area! Master bedroom has walk in closet and master bathroom. 3rd bedroom in the basement to be completed prior to closing.

$289,900

3 beds2 baths1,923 sq ft

105 Prospect St, Montfort, WI 53569

7,840 sq ft lot • $25 HOA • 2 garage spots

Gerald Adametz • Jon Miles Real Estate

ABOUT THIS HOME
Highland, WI Homes for Sale
Conveniently Located and Fully Renovated 3-Bed, 2-Bath Home in Montfort! Taken down to the studs and rebuilt with quality upgrades?metal roof (2012), furnace (2020), central air (2021), water heater (2018), and updated windows. All-new wiring, plumbing, lighting, oak doors, LVP flooring, cabinets, and countertops. Kitchen boasts Frigidaire appliances with transferable warranty. Plus, Ring security(Buyer will be responsible for the monthly fee), new subpanel, and basement tuck-pointing. County-inspected through every step?move in with confidence! Preapproval letter or proof funds requested by Seller prior to showings.

$260,000

3 beds2 baths1,325 sq ft

300 W Main St, Montfort, WI 53569

0.68 acre lot • Garage • Car-dependent

Jim Pahnke • Keller Williams Realty Signature

ABOUT THIS HOME
Highland, WI Homes for Sale
Renovated 3 bedroom 1 1/2 bath home with enclosed front porch. New kitchen and baths, electrical and plumbing updates, hvac, flooring, windows and exterior siding. This is a Fannie Mae Homepath Property.

$198,000

3 beds1.5 baths1,214 sq ft

3155 N Main St, Dodgeville, WI 53533

0.32 acre lot • Car-dependent

James Kilbane • Century 21 Affiliated

ABOUT THIS HOME
Highland, WI Homes for Sale
Accepted offer with bump as of 8/11/25. Brand new ranch style condo with brand new appliances. Over 1,800 sq ft living space on the main level. Full unfinished basement. Stubbed for bathroom, walls in basement studded for 2 more bedrooms and a big family rec room. This would double your living space. Spacious 2 car garage. Open floor plan. Big roomy kitchen with lots of cupboards and counter top area! Master bedroom has walk in closet and master bathroom. 3rd bedroom in the basement to be completed prior to closing. HOA fees are $25/month.

$289,000

3 beds2 baths1,923 sq ft

103 S Prospect St, Montfort, WI 53569

7,840 sq ft lot • $25 HOA • 2 garage spots

Gerald Adametz • Jon Miles Real Estate

$999,000

— beds— baths— sq ft

165+/- Acres Miess Rd, Dodgeville, WI 53533

165 acre lot • Car-dependent

Patrick Guyse • Whitetail Dreams Real Estate

ABOUT THIS HOME
Highland, WI Homes for Sale
Residential building site near the park, pool and downtown Montfort and adjoins a flat village owned lot for more elbow room. Sloped enough for a walkout lower level to economically add extra living space for your new home. Utilities to the lot line for your convenience ! Seller rep can be contracted to build for you or bring your own builder and get started while rates are down !

$20,000

— beds— baths— sq ft

308 S Madison St, Montfort, WI 53569

0.27 acre lot • Car-dependent

Gerard Abing • RE/MAX Advantage Realty

Average home prices near Highland, WI

Cities

Zip Codes

53543 homes for sale
$209,995
53569 homes for sale
$289,900

Highland, WI real estate trends

$260K

Sale price

+73.3%
since last year

$165

Sale $/sq ft

+32.0%
since last year

Over list price

Days on market

Down payment

—

Total homes sold

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