Portland Real Estate

Welcome to Portland, Wisconsin – a hidden gem nestled in the heart of the Midwest! This charming city offers a delightful blend of small-town warmth and vibrant community spirit, making it an ideal place to call home. With its picturesque landscapes and friendly residents, Portland is perfect for those seeking a peaceful lifestyle without sacrificing access to modern amenities.

Located just a short drive from the bustling city of Madison, Portland boasts easy access to a variety of recreational opportunities. The nearby scenic parks and nature trails invite outdoor enthusiasts to explore the beautiful surroundings, whether it’s hiking, biking, or simply enjoying a leisurely stroll. The pristine waters of the nearby lakes provide excellent fishing, boating, and swimming options, ensuring that residents can soak up the sun and enjoy the great outdoors.

Portland is not just about natural beauty; it also has a thriving local community. The city hosts numerous events throughout the year, from farmers' markets to seasonal festivals, fostering connections among residents and celebrating the rich culture of the area. With a strong emphasis on local businesses, Portland encourages a supportive atmosphere where you can find unique shops, cozy cafes, and delightful eateries that showcase the best of Wisconsin’s culinary scene.

Families will appreciate the excellent schools and safe neighborhoods, creating an environment where children can thrive. Whether you’re a first-time homebuyer, looking to downsize, or seeking a serene place to retire, Portland, WI, offers a welcoming community that feels like home. Discover the charm of Portland – where every day feels like a breath of fresh air!

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

Start Your Search

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.