95 properties for sale in East Winona

Affordable, move-in ready and maintenance free! 2+ bedroom home with an updated bath/laundry, full basement with high ceilings, plus a 2nd floor bath waiting for development! Great quiet neighborhood with a full lot and lots of yard space

Prepare to be surprised by everything this spacious home has to offer! Step inside and you’ll find a warm, inviting interior featuring beautiful bamboo flooring and a fantastic kitchen with stainless steel appliances, solid-surface countertops and plenty of space for cooking and gathering. The sun-filled four-season room, cozy gas fireplace and inviting living spaces make this home wonderful for both everyday living and entertaining. Generously sized bedrooms include a primary suite with a private half bath, while the lower level offers incredible flexibility with a large family room, kitchenette, additional bedroom and ¾ bath—ideal for guests, extended family or multigenerational living, with potential for rental use, subject to City rental certification. Additional highlights include a newer roof, yard sprinkler system, an impressive four-car garage and an additional carport providing exceptional parking and storage. Conveniently located near downtown Winona, this exceptionally well-

This clean, well-maintained, move in ready home is a 3-bedroom, 2.5 bath and offers plenty of space and natural light. The large windows brighten the home, while the spacious primary bedroom provides a comfortable retreat. The lower level features a family room, storage room, and additional space to enjoy. A 2-car attached garage adds convenience, and the wooded backyard offers a peaceful setting

Welcome to this spacious 4-bedroom, 3+ bathroom home located in the desirable Valley Oaks neighborhood! This home offers plenty of space along with features that make it comfortable for both everyday living and entertaining. Cozy up around the wood-burning fireplace or step outside onto the large back deck, offering a great space to relax, entertain, and enjoy the outdoors. The primary bedroom features its own full private bathroom and closet, while the additional bedrooms and bathrooms provide plenty of flexibility throughout the home. A 3-car attached garage offers excellent space for vehicles, storage, and more. Out front, the covered porch and porch swing create an inviting spot to sit back and enjoy the neighborhood. With 4 bedrooms, 3+ bathrooms, a large deck, wood-burning fireplace, 3-car garage, and a great Valley Oaks location, this home has plenty to offer

Very hard to find spacious 2,900 square foot 3-bedroom, 3 bath townhouse in a very private setting with wildlife abounding on all three sides! This property includes his and her offices/dens, 2 living rooms, main floor laundry, newer kitchen, custom stained glass, whole house surround sound plus a 4-car garage and a full basement just waiting for development

Welcome to this well-cared-for 3-bedroom, 2-bath home on Lake Boulevard, where year-round views of Lake Winona take center stage. Large living room windows bring the beautiful lake scenery inside and create a welcoming space to relax and enjoy the changing seasons. The home features new windows throughout, new laminate flooring, and spacious bedrooms with plenty of room for family, guests or a home office. An attached tuck-under garage adds everyday convenience, while the private backyard provides a great setting for gathering with friends, enjoying the outdoors or simply taking in the peaceful surroundings. A standout feature for hobbyists, mechanics or anyone needing extra space is the detached 18' x 26' garage in the backyard, offering plenty of room for a workshop, projects, storage or recreational equipment. With its combination of lake views, updates, outdoor space and exceptional garage setup, this Winona home offers a lifestyle that is hard to duplicate

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 offset their housing costs. Conveniently located near downtown Winona and just blocks from WSU, this property is an attractive option for both investors and owner-occupants

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 house with nice landscaping and a large new maintenance free deck which overlooks the Pleasant Valley creek which runs across the road to the east. What a great place to enjoy your morning coffee! The main floor has open kitchen/dining/living room area with multiple patio doors which lead to the new deck. The main floor master, laundry, and office are very nice features as well. There are 3 bedrooms upstairs, loft area and full bathroom. There is a 2-car heated and insulated garage along with a large attached heated workshop and paved 2 car carport area. There is a partially fenced in area and

2 bedroom, 1 bath home with lots of updates and plenty of space. The kitchen has tons of cabinets, a pantry, and all new black stainless steel appliances added in January 2025. New furnace and central air, plus new water and gas lines to the home. Main floor laundry and a freshly updated bathroom add convenience. Enjoy the front porch and watch the activity along the brand new road and sidewalks out front. The private fenced backyard includes two storage sheds. No garage, but there is plenty of off street parking. A great home with lots to offer!

Welcome home to this charming 2-bedroom, 1-bath home located just one block from Lake Winona! Inside, you'll find beautiful natural woodwork, hardwood floors, and built-ins that add warmth and character throughout. Numerous updates have already been completed, including a remodeled bathroom, many replacement windows, all-new plumbing, and new garage doors. Enjoy extra living and entertaining space with two three-season porches, a deck, and a patio overlooking the large background. An oversized 2-car garage with an additional carport provides plenty of room for vehicles, storage, and more. The home is also rental certified with a recently renewed rental certification, making is a great option for both an owner-occupant or investor. A cute, well-updated home in a great location close to the lake, walking and biking paths, and all that Winona has to offer!

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, while the two additional bedrooms flex into whatever your life calls for — think guest space, an office, or a room for the hobbies you actually want time for. Three full bathrooms means the morning rush stops being a battle of wills. Location is where this one really earns its keep. Winona East Lake Park sits nearby, so time spent along the water can become part of your regular routine. The Winona train station is located nearby, making trips out of town refreshingly simple. Winona itself is a gem — a friendly river town with plenty of character, local charm, and that easygoing pace that lets you actual

Step into the timeless beauty of this meticulously maintained 1893 Victorian home, showcasing Queen Anne architectural details and remarkable craftsmanship throughout. Decorative gables, beautiful hardwood floors, solid wood doors and original details give this home a character and warmth that simply cannot be recreated. The main level offers a living room, family room, formal dining room, three-quarter bath and a welcoming kitchen with a charming breakfast nook. Two separate staircases lead upstairs, where you’ll find three generously sized bedrooms, a full bathroom and a spacious laundry room. A clean, unfinished attic provides fantastic potential for future expansion. The full basement offers abundant storage and a large workshop. Outside, enjoy a one-car garage connected by a breezeway and a beautiful, covered patio perfect for relaxing or entertaining. Located just blocks from downtown Winona, you’ll enjoy convenient access to shopping, dining, entertainment and all that this hist

Welcome to 34810 Old Homer Road, a cozy, cabin-like retreat situated just across from the Mississippi River! This charming three-bedroom, one-bath home offers comfortable one-level living with spacious bedrooms, a generous full bathroom, newer furnace and central air, and a warm, inviting feel throughout. What truly sets this property apart is the additional lot, offering an incredible opportunity to build your dream home while enjoying the existing home for yourself, guests, or future possibilities. The additional lot features a gazebo/entertainment area, creating a great spot to relax and gather with family and friends. Outside, you’ll also find a storage shed, an established garden area with apple trees, rhubarb and beautiful lilacs, plus a large deck offering plenty of outdoor living space and ready for a little TLC. With its unique setting, additional lot and fantastic location across from the Mississippi River, this property offers possibilities that are hard to find!

Super convenient location close to the bike path with great views of Sugar Loaf! Set back from the street, this home offers a little more privacy and space, plus a yard filled with established perennials. Check out all of these updates! New roof in 2021 and brand new hot water heater. With the exception of the refrigerator, all appliances, including the washer and dryer, are under 5 years old. You'll find 4 bedrooms, including one extra large room that could easily be a crafting room, playroom, or whatever fits your needs. Two bedrooms are on the main level and two are upstairs, along with a large amount of storage space. Enjoy the outdoors from the front porch without worrying about the bugs. Main floor laundry and bathroom add convenience and make everyday living easier. This home is an open canvas ready for your personal touches and ideas!

First time on the market and truly one of a kind! This fun and whimsical property offers amazing views, beautiful established perennials and features you simply don't find every day. The main home has 3 bedrooms, a full bathroom, laundry tucked into a butler's pantry and 2 rooms with incredible views. The basement offers tons of storage. Outside, enjoy one of the most unique screened porches you will ever see, plus what is believed to be Winona Trolley #9, ready to become a garden shed or she shed. The lower level home includes a separate 1 bedroom living space with a kitchen, bathroom and laundry, perfect for guests, extended living or a mother in law suite. It could also offer potential for conversion to a garage. A truly special property!

A rare find in the heart of Winona! Built in 1980, this spacious home stands out among the surrounding historic homes and offers 3–4 bedrooms and 4 bathrooms. The main level features a welcoming living room, spacious kitchen with newer stainless-steel appliances and a large pantry, half bath, and a versatile den that could easily serve as a fourth bedroom or home office. Upstairs, you’ll find three generously sized bedrooms with exceptionally deep walk-in closets. The Jack-and-Jill style bathroom offers private vanity and toilet areas on each side with a shared tub/shower in between, providing both privacy and convenience. Step outside to a beautifully established yard featuring raspberries, blueberries, strawberries, colorful peonies, mint, and a garden area. A patio with gazebo provides a wonderful spot to relax or entertain, while a storage shed offers additional outdoor storage. With an attached one-car garage, abundant storage, a flexible floor plan, and a location in the heart of

Centrally located and just steps from the lake, this charming 3 bedroom, 1 bath home offers convenientmain-floor living at its finest! Inside you'll love the easy-to maintain vinyl and hardwood flooring throughout. No carpet! Step outside to your private outdoor space featuring a fully fenced backyard, spacious patio and a cozy fire pit. Perfect for relaxing or entertaining guests. Outstanding vehicle parking and storage space await in the oversized 2 car garage (That was freshly painted this spring). A wonderful place to call home

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 living room includes a wood-burning fireplace insert, while the sunroom offers triple-pane windows filled with krypton gas for exceptional insulation and energy efficiency. The home also features solar panels in the backyard, and all appliances are less than six years old. The water line to the main was replaced in 2020. Step outside to enjoy nearby walking and biking paths connecting to the lakes, with hiking in the bluffs also close by. The library and downtown Winona are approximately 1.5 miles away. Add in wonderful location that puts outdoor recreation and local amenities within easy reach

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 on main level. Low monthly association fees

Welcome to 363 Chatfield St. A beautifully maintained four-bedroom, two-full-bath home offering plenty of space, character, and versatility. Inside, you’ll find beautiful wood floors throughout much of the home, solid panel doors, a spacious kitchen, and vaulted ceilings on the upper level that add to the home’s charm. Numerous updates have been completed throughout the years, making this home truly move-in ready. Outside, you’ll find an open backyard with plenty of room to relax, entertain, garden, or enjoy outdoor activities. Whether you’re searching for a wonderful single-family home or an opportunity to add to your investment portfolio, this property offers options. The home is currently rental certified for up to five unrelated occupants, offering a great opportunity for homeowners and investors alike

3 bedroom, 1 bath home with plenty of potential to make it your own! Wood floors run throughout the home, and the basement offers bonus space for a family room, office, hobby area, or whatever fits your needs. This home needs some TLC, but it’s a great opportunity to put in your own updates and build equity alongthe way. The 2 stall garage provides great storage, and the large deck is a nice spot to relax orentertain. Located right on the parade route and just a short distance from the local donught shop, close enough to smell them!

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 rare. A total of 3,601 insulated and heated, including an extra 560 sq. Ft. not heated = total 4,161 sq. Ft. The home offers the opportunity to make it your own and needs new flooring throughout, allowing the next owner to choose flooring that fits their style and vision. Adding even more value and peace of mind, the roofs on both the home and shop were put on in 2022. Outside, enjoy the incredible setting beneath Sugar Loaf and take in the views of Winona and the surrounding Driftless Area. With more than a half-acre of land, there is room to enjoy the property while still being conveniently

Rarely does a property offer this combination of space, privacy, recreation, and versatility. Situated on approximately 1.6 acres in the desirable Spring Brook/Cobblestone neighborhood, this impressive home offers nearly 5,900 sq. Ft. of finished living space, 5 bedrooms, exceptional outdoor amenities, and an incredible six heated garage spaces. At the heart of the home is a beautifully designed kitchen with generous living and dining areas that flow effortlessly for everyday living and entertaining. The primary suite is a private retreat featuring its own fireplace, spa-inspired 5-piece bath, expansive walk-in closet, and adjoining bonus room—perfect for an office, fitness area, or quiet getaway. Upstairs are three additional spacious bedrooms, each with a walk-in closet, including two connected by a Jack-and-Jill bath and another with a private ensuite. The main level also features a dedicated office, laundry, multiple gathering spaces, and an inviting three-season room. The finished

Want to be close to town and the interstate while still enjoying space and privacy? This could be just the place for you! Situated just off Highway 43 on a little over 2 acres, this beautifully updated home offers the perfect blend of convenience and country living. Step inside to an inviting open-concept kitchen, dining, and living area featuring beautiful cabinetry, JennAir appliances, and a cozy gas fireplace. Large windows capture peaceful views from both the front and back of the home. With four bedrooms, two baths, and an attached two-car garage, there’s plenty of room to spread out. Need even more space? You’ll love the impressive 36x48 pole shed—perfect for all your toys, hobbies, storage, or workshop needs. Updated, spacious, private, and conveniently located—this property has so much to offer!

Located near the golf course, this 3 bedroom home offers plenty of space and possibilities. All 3 bedrooms are on one level, with one currently being used as a laundry and storage room. Move the laundry to the basement and open up that room for additional living space. Wood floors add character throughout the home. The large eat in kitchen is great for everyday meals, while the basement offers a spacious family room plus plenty of storage. Lots of closet space throughout, along with a great front porch to enjoy. The 40 x 16 garage gives you room for vehicles, a workshop, or all your extra toys

Welcome to 556 W 5th Street in Winona! This charming home offers an excellent opportunity for anyone seeking an affordable property in a convenient location. The comfortable floor plan makes great use of the space, while the fenced-in yard provides room for pets, gardening, entertaining, or relaxing outdoors. Conveniently situated near Winona’s shopping, dining, parks, schools, and other everyday amenities, this property delivers location and value at an attractive price. Whether you’re purchasing your first home, downsizing, or looking for an investment opportunity, this great little property is ready for its next owner. Schedule your showing today!

Stately 4 bedroom, 2.5 bath home with open porch and patio which looks out onto Lake Park. All bedrooms are on the upper level. The main floor boosts a formal dining room, huge living room with fireplace, sunroom which overlooks Lake Park and has a half bath

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 fantastic location

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 complete with a relaxing, jetted tub. You'll appreciate the convenience of the attached two-car garage and the additional living space provided by the enclosed three-season room. Step outside onto the rear deck and enjoy peaceful views with no backyard neighbors. With its thoughtful layout, spacious rooms, and meticulous upkeep, this home is ready for its next owners to move right in and enjoy

Charming 2-Bedroom Home in the Heart of Winona Welcome to this 2-bedroom, 2-bathroom home conveniently located in the heart of Winona. The home features main-floor laundry and a one-car garage with additional space for storage or hobbies. One of the highlights of this property is the fully fenced backyard, offering a great outdoor space to relax, entertain, garden, or enjoy time with pets. With two bedrooms, two bathrooms, main-floor laundry, a garage with extra space, and a private fenced backyard, this home offers comfortable living in a convenient Winona location. Come take a look and see what this home has to offer!