Portland Homes for Sale

Welcome to Portland, Wisconsin – a hidden gem nestled in the heart of the Midwest! Known for its picturesque landscapes and vibrant community spirit, Portland offers a unique blend of small-town charm and modern conveniences. With its friendly neighborhoods and lush green parks, this delightful city is perfect for families, retirees, and anyone looking to embrace a tranquil lifestyle.

Portland boasts a rich history, reflected in its beautifully preserved architecture and local landmarks. Residents enjoy a variety of outdoor activities, from hiking and biking along scenic trails to fishing in the nearby rivers. The city also hosts a range of community events throughout the year, fostering a strong sense of belonging and camaraderie among its residents.

For those considering a move to this enchanting city, the real estate market in Portland is thriving. Homes for sale here cater to diverse tastes and budgets, whether you’re searching for a cozy cottage, a spacious family home, or a charming bungalow. Many properties feature modern amenities while retaining their classic character, ensuring you’ll find a place that feels like home.

With competitive pricing and a welcoming atmosphere, investing in Portland real estate is a smart choice. Imagine waking up to the serene beauty of nature, enjoying friendly neighborhood gatherings, and becoming part of a community that values connection and support. Don’t miss the opportunity to explore the homes for sale in Portland, Wisconsin – your dream home awaits!

Newest Portland Homes for Sale

$550,000

6 Beds ⋅ 4 Baths ⋅ 2028975 MLS ⋅ ACTIVE UNDER CONTRACT Status

Come home to the country! 4,900+ sq ft on 4.8 acres. This charming 6 bed/4 bath farmhouse with a thoughtfully designed 2005 addition offers so much space and flexibility. Beautiful kitchen with a walk-in pantry, formal dining room, office, a large room plumbed and set up to be another kitchen. Upstairs has 4 bedrooms, including a primary suite with a walk-in closet and double-vanity bath. The addition features 2 additional bedrooms, a full bath, and a living room above the 3-car zero-entry garage. New roof and deck, fresh paint, carpeting. 75x40 pole shed, 30x30 shed, and 20x40 corn crib offer endless storage for equipment and toys. The perfect property for multi-generational living or for those who love to entertain. Peaceful and spacious- this is country living at its best.

W12242 Clarkson Rd, 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

$1,095,000

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

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This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.