Portland Real Estate

Welcome to Portland, Wisconsin – a hidden gem nestled in the heart of the Badger State! This charming city, rich in history and natural beauty, offers a unique blend of small-town warmth and vibrant community spirit. With its picturesque landscapes and friendly residents, Portland is the perfect place to call home.

Portland is renowned for its stunning outdoor recreational opportunities. Residents and visitors alike can enjoy the tranquil beauty of the nearby Kinnickinnic River, which provides excellent fishing, kayaking, and hiking options. The city is also surrounded by lush parks and nature trails, making it an ideal spot for those who appreciate the great outdoors.

The local community is tight-knit, with a variety of events and activities throughout the year that foster a sense of belonging. From farmers' markets featuring local produce to seasonal festivals celebrating the rich culture of the area, there’s always something happening in Portland. The city's commitment to supporting local businesses ensures a vibrant economy and a diverse selection of shops and eateries.

Education is a priority in Portland, with well-regarded schools that focus on providing quality learning experiences for children of all ages. The welcoming atmosphere and strong community values make it an ideal place for families to grow and thrive.

Whether you're seeking a peaceful retreat or an active lifestyle, Portland, Wisconsin, offers the perfect blend of both. With its charming ambiance, beautiful surroundings, and a community that feels like family, it’s no wonder that so many people are proud to call this city home. Come discover the magic of Portland – your new home awaits!

Newest Listings in Portland

$79,900

Built in 1983, this 36 x 40 shed/shop on .11 acres is located in the ''Town'' of Portland and just a very short distance from Hwy 33. Heated with Fuel Oil and insulated, this structure was constructed as a shed/shop for a milk hauling business and has had various uses since. Solid and well maintained. Located across road from residence which is assigned this address but is a separate tax parcel. Also listed with home across road for $319,900.

28067 Nash Rd, Portland

Listing courtesy of Shane Peterson Realty.

$249,900

4 Beds ⋅ 2 Baths

Location,Location, Location. Find yourself in this spacious pre-1900 home (with 1974 addition) on a .55 acre lot in the small ''Town'' of Portland. Only a 22 mile drive to La Crosse and views of farmland from your front deck. This spacious, well cared for 2 story home offers 4 bedrooms and 1 full bath above grade. Below grade there is an additional family room possible (no flooring currently so not counted in square footage) with fireplace (not used in 29 years so may need updates) and bar area. Vintage full bath below grade as well. 1 car extra deep attached garage and older front and rear decks as well as fenced yard. Updates include full window replacement in past 7 years and furnace at about 5 years old. Roof is around 10 years old. Character, charm and move in ready.

28067 Nash Rd, Portland

Listing courtesy of Shane Peterson Realty.

$299,900

3 Beds ⋅ 1 Baths

Opportunity and Location: 1977 Split Level Ranch on 11 acres just a short distance from Cashton. First time on market, has been owner occupied since build in 1977. Please note the many trophy buck mounts in both the home and the garage, all harvested from this property. Main level has 3 bedrooms and 1 bathroom. Lower level had a finished room but flooring is not present so is not counted in square footage. Two tax parcels (032-00571-0000 is 2 acres, Town of Portland and 016-00611-0000 is 9 acres, Town of Jefferson). Additional shed for storage. Note: basement is WOOD BASEMENT and some bowing has taken place and one support is broken. Functional, but will eventually need replacement and may not qualify for conventinoal loans. Priced accordingly or would be priced higher.

29053 State Highway 27 -, Portland

Listing courtesy of Shane Peterson Realty.

$524,900

4 Beds ⋅ 2 Baths

Looking to seek shelter from the social storm? If it's a fortress of solitude you're after, this fully functional homestead set on a picturesque 15.64 acres is the field of dreams you've been waiting for! Rolling hills, goats/chickens at pasture & waves of cornfields will be a few initial impressions. Generous enclosed porch leads directly into a wide open Kit/DR combo. Step outside & take in what true privacy & seclusion is all about. Epic sunrises/sunsets, an enclosed garden & endless horizons are sure to relax the soul. LR w/ NFP, 1/2 BA & full laundry round out the main level. Head up the refinished stairway to find the Primary BR boasting a WIC, jetted tub & sizable balcony providing even more incredible views. 2 ample BR's & a full BA complete the 2nd floor. Schedule a showing today!

N2440 Mulvaney Ln, Portland

Listing courtesy of Compass RE WI-Tosa.

$94,900

Rare opportunity to own 1.6 wooded acres along the scenic Crawfish River! Tucked away on a quiet dead-end road, this beautiful property offers the perfect setting for a private recreational retreat surrounded by mature trees, abundant wildlife, and picturesque river views. The owner has selectively cleared portions of the property to create open spaces while preserving its natural beauty, making it ideal for camping, relaxing, fishing, kayaking, birdwatching, or simply enjoying the outdoors. An existing driveway entrance, on-site well, and electricity available nearby provide added convenience.

N1926 River Oaks Rd, Portland

Listing courtesy of Platner Realty.

$550,000

6 Beds ⋅ 4 Baths

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

Listing courtesy of eXp Realty.

$625,000

5 Beds ⋅ 2 Baths

Rare 10-acre farmette offering 5+ tillable acres & a beautifully updated brick farmhouse with 5 bedrooms, 2.5 baths, hardwood floors, tall ceilings, & charming woodwork. The inviting layout features a modernized kitchen with granite island & pantry, spacious living room, den, main floor bedroom, full bath & laundry, & a 3-season porch leading to a wraparound deck & fenced front yard for pets. Upstairs you'll find four bedrooms, walk-in closets, full bath & a walk-up attic. Outbuildings offer storage or income potential including barns, pole shed, silos & Quonset shed- perfect for livestock, crops, or equipment. Set in a serene country setting just outside Dane County with rolling views, this property offers endless possibilities for your dream hobby farm or private retreat. Call today!

W12040 Sullivan Rd, Portland

Listing courtesy of Realty Executives Platinum.

$1,095,000

3 Beds ⋅ 3 Baths

Leave the city behind for 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 is made for relaxing and entertaining. Cook in the gourmet kitchen, cozy up by the fireplaces, host summer gatherings on the spacious lower deck, or enjoy morning coffee from the private 2nd floor deck off the primary suite. Major updates include flooring, luxury baths, roof, windows, siding, electrical, plumbing, furnaces, central AC, mound system, and landscaping. The large barn needs TLC but adds endless possibilities for hobbies, animals, or storage. Escape to the calm of a quiet country road and a picturesque drive home, with Madison less than an hour away.

W10823 Port Rd, Portland

Listing courtesy of RE/MAX Community Realty.

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Source of listing data: Metro MLS. Copyright 2026 Multiple Listing Service, Inc. - All Rights Reserved. Information is supplied by seller and other third parties and has not been verified. IDX information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.