Winona, MN Homes for Sale under $500,000

The beautiful open concept 3000 sq ft, 4-bedroom 2 bath home has vaulted ceilings and windows from floor to ceiling which allow you to take in the breathtaking views of the Pleasant Valley from most all the rooms in the house. The fully paved driveway leads to the house which sits perched on the wooded hillside and full of mature pines, oaks and hardwood timber. A concrete patio wraps around the

Jeff Brogle Bluff Country Properties,LLC.

Welcome to this spacious 5-bedroom home. 4 bedrooms conveniently located on the main floor plus a room in the basement that could be a bedroom or used as a rec room/bar. The house sits on a generous corner lot in a quiet, well-established neighborhood. This property offers a solid foundation and a functional layout, ready for your personal touch and updates. Large windows bring in plenty of

Gile Gibbons Edina Realty, Inc.

Great opportunity to own a well-located duplex in Winona featuring two units, each with 4 bedrooms and 1 bathroom. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this property offers excellent flexibility. The two-unit setup offers the potential for strong rental income while giving an owner-occupant the opportunity to

Laura Slavey Keller Williams Premier Realty

Welcome home to this spacious and inviting 2-bedroom, 3-bath residence conveniently located in the heart of Winona! With exceptionally large bedrooms, each featuring its own private bathroom, this home offers comfort, privacy, and a layout that's perfect for a variety of lifestyles. The oversized living room provides an ideal gathering space, while the generous dining room is ready for everything

Tina Goettelman Edina Realty, Inc.

Paul J Van Eijl Richard L. Jacobson Real Estate

Looking for country living in one the most energy efficient homes you will ever see? Well, look no further! This three bedroom, two bath home nestled on 9 acres in Homer Valley was meticulously constructed with efficiency in mind. Triple pane windows, double insulated, insulated concrete forms, geothermal air conditioning, and high efficiency appliances keep your cost of living low year-round.

Paul Ebner RE/MAX Advantage Plus

LOCATION, LOCATION, LOCATION! Long time investment property for sale right across the street from the WSU Wellness Center. This is a certified duplex with 3 bedrooms down and 2 bedrooms up. Long, solid rental history. Rental certified for 5 unrelated down and 3 unrelated up. No laundry on site. Both units are rented for June 1, 2026-May 25, 2027. Upstairs rent is $850/month and downstairs rent is

Brent Kimmerle Real Broker, LLC.

Welcome home to this beautifully maintained 3-bedroom, 3-bathroom property offering generous living spaces, abundant storage, and a wonderful setting overlooking an open field. The spacious layout includes an inviting eat-in kitchen, a separate dining room, and large bedrooms designed with both comfort and functionality in mind.The primary suite features a large walk-in closet and a bathroom

Eric Nustad Key Real Estate

Better than new! Located in the heart of Winona, this stunning 4-bedroom, 3-bath home has been rebuilt from the ground up with quality craftsmanship throughout. Nearly everything is new, including the plumbing, electrical, furnace, central air, roof, and so much more—offering the peace of mind and feel of new construction while maintaining its convenient in-town location.Step inside to an

Angela Thompson Coldwell Banker River Valley, REALTORS

Immaculate townhome in quiet neighborhood. Easy main floor living with primary bedroom walk-in closet and private bathroom. Vaulted open kitchen with large breakfast bar/island and spacious living & dining room with fireplace that walks out to the deck overlooking woods. Lower level has family room that walks out to the patio, second and third bedrooms or office, full bath. Laundry and half bath

Jonelle Moore Coldwell Banker River Valley, REALTORS

Welcome to this charming and nicely updated home on a desirable corner lot. Everything has been done for you, including a brand-new metal roof, a new HVAC system and newer flooring throughout. Best of all, this property is rental certified, making it an incredible find for both future homeowners and smart investors. Do not miss out on a turn-key property that combines modern comfort with a

Mark Miranda Edina Realty, Inc.

Three bedrooms, three bathrooms, and a comfortable 2,172 square feet — this house has the kind of breathing room that makes daily life feel a whole lot easier. Whether you're looking for extra space or simply want more room to spread out, this floor plan delivers.Inside, the layout keeps things practical without feeling cramped. The primary bedroom gives you a quiet spot to retreat to,

Luke Ihde Homes Plus Realty

Whether you want to have your business right at home or need plenty of storage space, this is the one, just minutes from Winona. This home is booming with character and waiting for you to add your touches. With four generous bedrooms, two bathrooms, an updated kitchen with new appliances, large dining & living rooms, attached one car garage, a partially finished basement for additional living

Jesse Ebner RE/MAX Advantage Plus

Welcome home to this charming 3-bedroom, 2-bathroom home in a fantastic Winona location! Enjoy stunning views from the living room and primary bedroom, along with beautiful red oak hardwood floors in the main living and dining areas and two main-floor bedrooms. The hardwood floors were refinished in 2018, and the kitchen features a new laminate countertop installed in December 2024. The inviting

Donna Dahl Pemberton RE

Charming ranch style home in excellent condition located in valley among bluffs on 1.4 acres. Main floor features a sunroom that walks out to maintenance free deck overlooking beautiful lot. Large living room/ dining room area has fireplace and view of bluffs. Three bedrooms on main floor. Lower level has huge family room, storage/utility room and half bath. Extra long garage allows for both cars

Jonelle Moore Coldwell Banker River Valley, REALTORS

Escape to the peace and privacy of country living with this charming farmhouse situated on 6.7 scenic acres at the end of a quiet dead-end gravel driveway. Updated in 2014/2015, this inviting home blends modern comforts with much charm. The spacious kitchen serves as the heart of the home, featuring in-floorheat, a cozy pellet stove, and two convenient exterior doors providing easy access to

Bruce Bechly Keller Williams Premier Realty

The shop is the true standout. With 2,275 sq. ft. that have 16-foot ceilings, two 14-foot garage doors, three additional 8-foot garage doors, and a heated portion of the building, there is an incredible amount of room for vehicles, equipment, hobbies, storage, and a 1/4 bathroom. Finding this kind of substantial workspace on a property this close to everything Winona has to offer is exceptionally

Shawn Beier Real Broker, LLC.

Welcome home to this beautifully updated 3-bedroom property offering the convenience of all three bedrooms on the main level, including two spacious bedrooms with the master having a wonderful walk-in closet! The heart of the home is the beautiful, remodeled kitchen (2025), featuring modern finishes and thoughtful updates that make it perfect for everyday living and entertaining. Extensive

Tina Goettelman Edina Realty, Inc.

Warrantied home! Welcome to this spacious and beautifully updated 5-bedroom, 4-bathroom home offering over 4,000 square feet of thoughtfully designed living space on a desirable quarter-acre lot in WE Valley. Perfect for both everyday living and entertaining, this impressive home features two extra-large family rooms in addition to a formal living room, providing plenty of space for gatherings,

Celeste Liesch Edina Realty, Inc.

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

Jim Clark Keller Williams Premier Realty

Motivated sellers! Welcome to this well-maintained two-story duplex offering an excellent opportunity for both owner-occupants and investors. Featuring one upper unit and one lower unit, each residence has its own private laundry, creating convenience and eliminating shared common spaces.This property has seen numerous recent updates, including newer appliances, brand-new ovens in both units,

Tina Scharmach Castle Realty, LLC

Welcome to river living! Enjoy your own piece of Mississippi River paradise with this charming 2 bedroom home offering the perfect combination of comfort, convenience, and a peaceful waterfront setting. Whether you're searching for a year-round residence, weekend getaway, or investment opportunity, this property delivers the lifestyle buyers dream about. Relax & take in the river views, watch the

Dawn Levandoski RE/MAX Results

Immaculately maintained and nicely updated 3-4 Bedroom, 2 Bath Rambler in convenient West side location. Close to shopping, schools and restaurants! The 2-car attached garage features a newer 10'x20' workshop addition on the back. You are sure to enjoy the tranquil backyard green space, the manicured landscaping, and the new paver patio. The main level boasts 3 bedrooms, newer LVP flooring, and

Brent Kimmerle Real Broker, LLC.