Portland Real Estate

Welcome to the charming city of Portland, nestled in the heart of Monroe County, Wisconsin. Known for its picturesque landscapes and a close-knit community, Portland offers a unique blend of rural charm and modern amenities, making it an ideal place to call home.

With its scenic views and abundant outdoor recreational opportunities, Portland is perfect for nature enthusiasts. The surrounding area is adorned with lush parks, tranquil lakes, and winding trails, providing residents with countless opportunities for hiking, fishing, and enjoying the great outdoors. The nearby Black River State Forest offers miles of trails for hiking, biking, and snowmobiling, ensuring that every season brings new adventures.

Portland's vibrant community spirit is reflected in its local events and gatherings. Throughout the year, residents come together to celebrate their small-town heritage with festivals, farmers' markets, and community picnics. The welcoming atmosphere fosters strong connections among neighbors, making it easy to feel at home.

In addition to its natural beauty, Portland boasts a variety of local shops, restaurants, and services that cater to the needs of its residents. Whether you’re grabbing a coffee at a cozy café or exploring unique boutiques, you’ll find that Portland has much to offer.

With its affordable housing options and family-friendly environment, Portland is not just a place to live; it’s a place to thrive. Discover the charm of this delightful Wisconsin city and experience the warmth of a community that feels like family. Come see why Portland is the perfect place to plant your roots!

Newest Listings in Portland

$479,900

4 Beds ⋅ 2 Baths ⋅ 2025250 MLS ⋅ ACTIVE UNDER CONTRACT Status

Extensively renovated from the studs with nearly every major component replaced in 2025-2026. This home offers the perfect blend of peaceful rural surroundings and modern updates. Situated on a spacious lot, this home has been thoughtfully updated throughout, making it move-in ready for its next owner. Inside, you'll find an open concept living space, fresh finishes, updated flooring, and a bright, inviting layout designed for comfortable everyday living. The kitchen features modern touches, a kitchen island, and plenty of space for cooking and entertaining, while the living areas offer a warm and welcoming atmosphere. *Completion anticipated for late JUNE 2026! *Final exterior improvements, a few basement windows, and garage completion underway.

N2485 County Road Ii, Portland

$1,150,000

1 Beds ⋅ 1 Baths ⋅ 2023867 MLS ⋅ ACTIVE Status

Available for the first time in over 2 decades! This pristine recreational property has it all! A fine balance of woods with a perfect blend of pasture/prairie that make this property ideal for hunters and those looking for utv/snowmobile use. Walk along the beautiful trails system that covers the property making it easy to access and appreciate all the land has to offer. On your tour, you'll see spring fed ponds, rock outcroppings, stunning views and beautiful ravines. This property is a true slice of heaven, but don't overlook the 40x60 fully insulated Shed with 14' sidewalls, 12' overhead door with 3 additional overhead doors, white steel sheeting and full electric service including multiple 220 outlets. Walk from the shop to the immaculate 1130 square foot living quarters with 12x15 loft, full kitchen complete with hickory hardwood cabinets, finished concrete floors, dining room and living room with stone backed woodburning fireplace. Don't miss out on this rare opportunity.

27526 County Highway X, Portland

$1,150,000

2023842 MLS ⋅ ACTIVE Status

27526 County Highway X, Portland

$1,199,000

3 Beds ⋅ 4 Baths ⋅ 2023360 MLS ⋅ ACTIVE Status

Leave the city behind and fall in love with this COMPLETELY remodeled farmhouse on 3.88 scenic acres bordering DNR land! Full of charm and packed with modern luxury updates, this 3-bedroom, 3.5-bath retreat offers peaceful countryside views with nature all around. Create unforgettable meals in the gourmet kitchen, cozy up by the fireplaces, host summer gatherings on the spacious lower deck, or sip morning coffee from the private second-story deck off the primary suite. Thoughtfully updated from top to bottom, improvements include new flooring, hi-end bathrooms, roof, gutters, windows, doors, siding, electrical, plumbing, furnaces, central AC, mound system, and fresh landscaping. Simply move in and enjoy! With some TLC, the large barn offers endless potential for hobbies, animals, or extra storage. Escape to the calm of a quiet country road and a picturesque drive home, yet enjoy dining, shopping, and entertainment in Madison less than an hour away.

W10823 Port Rd, Portland

$189,999

2 Beds ⋅ 1 Baths ⋅ 2013485 MLS ⋅ ACTIVE Status

Buyer to verify all measurements

27891 County Highway X, Portland

$75,000

2009114 MLS ⋅ ACTIVE Status

Buyers, this is the lot you've been waiting for! Over an acre lot at an affordable price of $75,000! This is a corner lot in a great location with just a 22 minute drive to Sun Prairie. Electric service at the lot line. Well and Septic required, and LP tank needed. Schedule your tour, today!

1.09 Acre Dalman Rd, Portland

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