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$320,000
5 Beds 2 Baths 7077668 MLS
Welcome to this spacious and move-in ready 5-bedroom, 2-bath home offering room for everyone inside and out! Step inside to find multiple living spaces, updated flooring, and a functional layout designed for everyday living and entertaining. The kitchen offers ample cabinet space, a center island, and flows nicely into the dining area with access to the large deck and fenced backyard. The finished lower level provides additional living space, extra bedrooms, and a beautifully updated bathroom with a tiled walk-in shower. Outside, you’ll appreciate the oversized yard, mature trees, and attached 2-car garage. Conveniently located near parks and a school, this home combines space, comfort, and value all in one package.

5250 W 9th Street, Winona

Listing courtesy of Richard L. Jacobson Real Estate.

$2,550,000
3 Beds 4 Baths 7069381 MLS
Welcome to paradise, located in the Pleasant Valley minutes outside Winona. This estate has many amazing qualities. Enter the estate on a fully paved driveway with an arched wrought iron entrance and custom concrete bridge, which passes over the teaming stream. The paved drive bordered by white picket fences leads to a concrete circle driveway entrance to the house. The 5,000+ square foot house is a 3-bedroom 4-bath, 2+ car heated and finished garage, open style executive walkout rambler. The entire house spares no detail and has been very well taken care of. Enjoy the large main floor master suite, with a large walk-in closet, and overlooks the pool and trout stream. Solid surface counters are in the kitchen and throughout the house. Main floor and lower floor laundry rooms. 3-season east and south-facing sunroom for a quiet place to take in the beautiful bluff country. Generous living room, family room, storage, abundant custom oak cabinets throughout, and a unique sit-down bar in the lower level. There is a sprawling custom concrete space with an in-ground pool and a custom-built pool pavilion that includes a kitchen and bathroom. The 36’x48’ horse barn has 3 stalls, a tack room, and an open area for managing the horses. There is a very large remodeled dairy barn, which has hand-hewn timber beams along with finished and heated workshop spaces. The 50’x70’ outbuilding has both cold storage and finished heated spaces. The 50’ x 80’ cold storage machine shed provides space to house farm equipment and supplies. The 140 acres of land includes 1/2 mile of private Pleasant Valley Creek, which has an abundance of trout, springs which feed two ponds, 40 acres of fenced and gated rotational grazing grounds, well-maintained trails through the property, valuable mature timber, 40 acres of tillable land, clover and alfalfa food plots for deer and turkey hunting, and 4 permanent enclosed hunting blinds. There is a custom-built trapper’s cabin which has bunks, heat, and a front porch where one can retreat to get away from it all. 1 mile from the 18-hole Bridges Golf Course and restaurant. Minutes to Lake Winona, where there are miles of paved biking and running trails, downtown Winona, and the Mississippi River.

24020 CTY RD 17, Winona

Listing courtesy of Bluff Country Properties,LLC..

$475,000
2 Beds 1 Baths 7069283 MLS
Escape to your own private retreat in the scenic bluff country of Winona, MN. This charming rustic log home, built with beautiful Montana pine, sits at the end of a quiet road on 27 acres, offering seclusion, privacy, and peaceful surroundings. This cozy 2-bedroom, 1-bath lodge is perfect as a personal getaway or a basecamp for outdoor adventure. Enjoy nearby hiking and camping, with plenty of space to explore and experience the natural beauty surrounding the property. Relax and unwind on the inviting covered front porch, where you can take in the fresh air, wooded views, and tranquil setting. Whether you're looking for a quiet escape or a place to reconnect with nature, this Private wilderness-style property delivers.

24141 Homer Valley Road, Winona

Listing courtesy of Keller Williams Premier Realty.

$850,000
5 Beds 3 Baths 7062600 MLS
This house truly has it all—set on 40 acres of land on Bollers Lake in Goodview, it offers a rare combination of luxury, comfort, and country living just 2 minutes to Winona. Completely renovated throughout, the home showcases a designer chef’s kitchen with premium finishes, high-end bathrooms featuring custom tile and stone, and a stunning great room with soaring 20-foot ceilings. A private indoor heated swimming pool, complete with a fireplace and water feature, creates a year-round retreat right at home. The property includes a 3-car attached garage, plus a bonus outdoor wood stove capable of heating both the home and the pool room. With space for small livestock and zoning for agriculture and natural resources, the opportunities are endless—whether you envision a private getaway, hobby farm, or lakeside estate. This one-of-a-kind property blends modern elegance with natural beauty in an unmatched setting.

2331 Goodview Road, Winona

Listing courtesy of Edina Realty, Inc..

$848,000
5 Beds 5 Baths 7055050 MLS
This stately 5 Bedroom, 5 Bathroom 1930 English Tudor offers an incredible location in the heart of Winona with sweeping views of the Bandshell, Veteran's Park, Lake Winona and Sugar Loaf. It is packed with charm inside and out. Adjacent to four city owned tennis courts, it is situated on 3 city lots. The all-brick exterior has intricate pattern design and Biesanz stone highlights. A tile roof and leaded glass windows add to the curb appeal. Interior features include original hardwood floors, an updated kitchen with quartz countertops and custom tile bathrooms. The main level has 9-foot ceilings and beautifully textured plaster walls with crown molding. Each level has a stone, wood burning fireplace, spacious rooms and ample storage exists throughout. A Biesanz stone upper terrace walk was replaced in the late Fall of 2025. Every corner of this residence reflects nearly three decades of meticulous care and thoughtful updates, creating a sanctuary that is as move-in ready as it is soul-warming.

51 W Sarnia Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$549,000
2 Beds 3 Baths 7052964 MLS
This 2025-built home offers high-end finishes and thoughtful design throughout. Located within walking distance to Saint Mary’s University, the setting adds everyday convenience in a fantastic neighborhood with walking and biking trails, plus easy access through the underground tunnel. Step inside and you’re greeted by a stunning open-concept design, elevated craftsmanship, and attention to detail throughout. The kitchen features Cambria quartz countertops, cabinetry extending to the ceiling, and a seamless flow into the living space highlighted by a gas fireplace with custom tile. Solid panel doors, recessed lighting inside and out, sunlit Anderson windows, and in-floor heat in both the home and garage add to the comfort and quality. Designed for one-level living, the home features extra-wide hallways and doorways for added accessibility, while the upper level offers additional space that works well for guests, caregivers, or extended family. A whole-house reverse osmosis system and truly maintenance-free construction make everyday living simple and efficient. The primary suite includes a beautifully finished bath with a custom ceramic tile shower featuring both a rain showerhead and a second showerhead for added comfort. Concrete countertops in the bathrooms and laundry room add a custom, high-end touch throughout. The main floor also offers a convenient laundry room and dedicated office space. Upstairs, the loft provides a spacious family room, additional bedroom, and full bath—with plans already in place for a potential third bedroom if desired. The level of detail in this home is exceptional, including abundant electrical outlets—even in closets—adding everyday functionality that sets it apart. Outside, enjoy a maintenance-free Trex deck, a privacy-fenced yard, and professionally landscaped grounds complete with a sprinkler system. The oversized, heated two-car garage includes a water faucet, adding even more versatility. Enjoy neighborhood amenities including pickleball and tennis courts, along with a playground just steps away.

54 Brickyard Lane, Winona

Listing courtesy of Edina Realty, Inc..

$549,900
4 Beds 3 Baths 7052082 MLS
Welcome home to this beautifully designed 4-bedroom, 3-bath property nestled on a quiet cul-de-sac with breathtaking bluff views. From the moment you arrive, you’ll appreciate the peaceful setting and the opportunity to enjoy both sunrises from the covered front deck and relaxing evenings surrounded by nature on the back patio. The main level offers an inviting open-concept layout, where the kitchen and family room come together around a stunning two-sided gas fireplace—perfect for cozy nights and entertaining alike. Large windows frame the incredible views, bringing the outdoors in. You’ll also find a kitchen nook and a formal dining room that leads directly to the back patio, creating seamless indoor-outdoor living. The primary suite is conveniently located on the main floor and features a private ensuite bath and walk-in closet. Downstairs, the lower level boasts 9-foot ceilings, giving it a bright, spacious feel. A huge family room provides plenty of space for gatherings, along with two additional bedrooms and excellent storage options. Complete with a 2-car garage and thoughtfully designed spaces throughout, this home offers comfort, functionality, and views you won’t want to miss.

76 Rodeo Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$189,999
5 Beds 2 Baths 7023513 MLS
This rental-certified home is approved for 5 unrelated or 9 related occupants and is ideally located just three blocks from Downtown Winona, minutes from Winona State University, and within walking distance to a grocery store and everyday amenities. Offering five bedrooms and two main-floor bathrooms, the spacious layout provides flexibility for a variety of living arrangements — whether owner-occupied or used as an investment property. The home features main-floor laundry, off-street parking spaces, and a larger storage shed. Numerous updates have been completed over the years, including improvements to the electrical system, newer windows, lighting, newer washer and dryer, newer forced-air furnace and central air conditioning unit, and more — providing added value and peace of mind for the next owner. A well-maintained property in a convenient location with strong long-term potential.

263 Franklin Street, Winona

Listing courtesy of Edina Realty, Inc..

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