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801 Spring Brook Drive, Winona
$899,900
4 Beds ⋅ 5 Baths ⋅ 7128634 MLS
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 lower level adds even more flexibility with a spacious family room, wet bar, media room, 5th bedroom, bath, and abundant storage. Outside, enjoy the level backyard, patio with fire pit, and private Sport Court—ideal for basketball, pickleball, and year-round family fun. Two separate heated 3-car garages provide outstanding space for vehicles, recreational toys, hobbies, a workshop, and storage. A new septic system adds additional peace of mind. With its acreage, impressive square footage, recreational amenities, and unmatched garage space, 801 Spring Brook Drive offers a lifestyle and versatility that are truly hard to find.

801 Spring Brook Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

419 E Broadway Street, Winona
$175,000
3 Beds ⋅ 1 Baths ⋅ 7127670 MLS
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!

419 E Broadway Street, Winona

Listing courtesy of Keller Williams Premier Realty.

720 Main Street, Winona
$570,000
4 Beds ⋅ 3 Baths ⋅ 7126672 MLS
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.

720 Main Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

574 Wilson Street, Winona
$205,000
3 Beds ⋅ 1 Baths ⋅ 7122198 MLS
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.

574 Wilson Street, Winona

Listing courtesy of Edina Realty, Inc..

765 E Lake Boulevard, Winona
$299,900
4 Beds ⋅ 1 Baths ⋅ 7125858 MLS
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 located in town. If you've been looking for a property that combines a home, land, breathtaking views, and an exceptionally large shop in the heart of Winona, this is one you won't want to miss. The shop alone makes this property a rare find—and the location, acreage, and views make it even more special. WELCOME HOME!

765 E Lake Boulevard, Winona

Listing courtesy of Real Broker, LLC..

24334 County Road 9, Winona
$674,900
3 Beds ⋅ 4 Baths ⋅ 7122835 MLS
Where the prairie meets the horizon and peace becomes part of everyday life. Nestled in the breathtaking natural beauty of Cedar Valley, this 10+ acre country retreat offers a rare opportunity to experience peaceful country living surrounded by rolling bluffs, open meadows, and abundant wildlife. Built in 1984, this well-constructed home was thoughtfully designed to embrace its spectacular surroundings, with large windows throughout filling the home with natural light and showcasing stunning views in every direction. Offering over 4,200 square feet of living space, the home features 3 spacious bedrooms and 3 bathrooms, soaring vaulted ceilings, two inviting fireplaces, and a generous primary suite with a private ensuite. The kitchen opens to a wraparound deck through sliding glass doors, creating the perfect place to enjoy your morning coffee, entertain guests, or simply take in the breathtaking prairie sunrises, sunsets, and star-filled skies. This remarkable property serves as a peaceful sanctuary while remaining just a scenic drive from Winona, Minnesota, and La Crosse, Wisconsin. Cedar Creek, a healthy, clean trout stream, winds through the valley, creating a truly picturesque setting. Wildlife enthusiasts will appreciate the abundance of birds, butterflies, and native prairie habitat, making every season something special. A 2-car attached garage and a large pole barn provide plenty of space for vehicles, recreational equipment, hobbies, or a hobby farm. A new septic system has already been installed, providing added value and peace of mind. Whether you're searching for a private country retreat, a hobby farm, or simply a place where family and friends can gather to enjoy nature, this property offers a lifestyle that is becoming increasingly difficult to find.

24334 County Road 9, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

763 W Mark Street, Winona
$164,900
3 Beds ⋅ 1 Baths ⋅ 7120056 MLS
763 W Mark Street, Winona Has New Updates; NEW LVP Flooring in Living Room, NEWLY Stained Front Porch, NEWLY Stained Back Deck & Steps, NEWLY Stained Back Yard Fence & Front & Backyard Landscaping! You will LOVE the 3 Main Floor Bedrooms, Spacious Kitchen with Tiled Floors, Replaced Cabinetry & Countertops & Stainless Steel Appliances. The Backyard is Fully Fenced, offering privacy & safety for families, children & pets, plus open parking for 2+ vehicles! The Roof, Thermo Windows, Stainless Steel Appliances, Water Heater & Forced Air Furnace are all in good condition! The Main Floor also includes a separate Laundry Room with Washer & Dryer included in the sale. Special Bonus - The Fully Finished Upstairs offers 2 rooms which are perfect for many purposes: an office, hobby room, exercise room, den, storage, media/gaming, additional sleeping & storage galore! This property is Rental Certified. Come & Look Now!

763 W Mark Street, Winona

Listing courtesy of Jewson Realty.

1555 48th Avenue, Winona
$450,000
5 Beds ⋅ 4 Baths ⋅ 7113201 MLS
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, relaxation, or recreation. Enjoy the convenience of two dining areas, three cozy gas fireplaces, and two laundry rooms. The expansive lower level boasts a large bar area with ample room for a pool table, game room, or additional dining space, making it an ideal entertainment hub. An oversized garage offers generous storage and parking, while the freshly painted interior and numerous recent updates give the home a fresh, move-in-ready feel. With its exceptional space, versatile layout, and desirable location, this WE Valley home is ready to welcome its next owners. Seller to provide 1 year home warranty with purchase.

1555 48th Avenue, Winona

Listing courtesy of Edina Realty, Inc..

53 W Lake Boulevard, Winona
$799,900
5 Beds ⋅ 5 Baths ⋅ 7110230 MLS
Backing up to a wooded city park and nearby Sugarloaf, this unique home sits on 2 1/2 acres of lush and verdant gardens. This oasis overlooks Lake Winona and beyond it much of Winona proper and the river. The pool house is made from the original stables on the property, and the hillside is dotted with trails to the gazebo, pickleball court and various seating areas. A koi pond and waterfall feature sit just beyond the kitchen and mere steps out the door is a wonderful patio and screen porch to enjoy whatever kind of day the weather brings. This home is expansive and in addition to the 5 bedrooms and 5 bathrooms includes design features you won't find elsewhere. A distinctive turret, a beautifully painted room with vaulted chapel-like ceilings and natural woodwork throughout are just some of the notable features. Outside a spacious detached garage has three individual stalls as well as unfinished updoor space that would make a great workshop, office space, or storage. Many new updates in this home, but some notable ones include: Custom blinds (2023), new boiler (2019), new water heater (2025), Tiled floor in family room (2025). The open kitchen is perfect for entertaining and features custom maple cabinets with exquisite detailing, a down-venting stove, double ovens, a walk-in pantry and a commercial sized fridge. The outdoor areas are not-to-be-missed too; outdoor speakers, expansive gardens, landscape lighting and more make this yard a show-stopper. The pool has many updates including a new liner and pump (2023), new filtration system (2024), new heater and light (2025) and new skimmer (2026).

53 W Lake Boulevard, Winona

Listing courtesy of Creek Realty.

104 Forest Oak Court, Winona
$625,000
4 Beds ⋅ 4 Baths ⋅ 7111839 MLS
Hidden at the end of a quiet cul-de-sac, this remarkable cedar home offers the best of both worlds: a peaceful, wooded setting on 1.72 acres with the convenience of being just minutes from everything Winona has to offer. With over 4,700 finished square feet, there's room for everyone to spread out without ever feeling connected. Sunlight pours through walls of windows, highlighting the beautiful hardwood floors and stunning natural woodwork that make this home feel warm, inviting, and truly one of a kind. The main level was designed with gathering in mind. Whether you're hosting Thanksgiving dinner, cheering on your favorite team, or enjoying a quiet evening by the fire, you'll appreciate the spacious living areas connected by a gorgeous double-sided wood-burning fireplace. The kitchen offers everything a home chef could want, including a large center island, wall oven, cooktop, wine cooler, extensive cabinetry, and plenty of prep space. Choose between casual meals in the breakfast area or hosting friends and family in the formal dining room. Upstairs, you'll find four spacious bedrooms, including a private primary suite where you can wake up to peaceful views of nature. The ensuite features a jetted soaking tub, separate walk-in shower, and the perfect place to relax after a long day. Need even more room? The finished lower level offers endless possibilities with expansive recreation space, an additional sitting area, a ¾ bathroom, and generous storage. Whether you envision a game room, home gym, movie room, or guest retreat, the space is ready to fit your lifestyle. The pool table is negotiable with the sale. Step outside and you'll quickly understand what makes this property so special. The current owners have thoughtfully designed the landscape to showcase a variety of native Minnesota wildflowers, creating a yard that's as beautiful as it is intentional. From cheerful Black-eyed Susans to fragrant lavender hyssop and native peppermint, the gardens come alive in waves of color throughout the growing season while naturally attracting pollinators and helping create a more enjoyable outdoor space. Relax in the included hot tub, entertain on the deck or patio, or simply take in the peaceful views of mature trees and rolling green space. Every season brings something new to enjoy, and every window offers a view worth appreciating. Additional highlights include main floor laundry, zoned heating and cooling with two furnaces and two central air units, an oversized three-stall garage with more than 1,000 square feet of space, and a large turnaround driveway for guests. Homes like this rarely become available. If you've been searching for space, privacy, incredible craftsmanship, and a setting that feels like a retreat without sacrificing convenience, this home deserves a spot at the top of your list.

104 Forest Oak Court, Winona

Listing courtesy of Real Broker, LLC..

617 W Howard Street, Winona
$162,900
2 Beds ⋅ 1 Baths ⋅ 7111037 MLS
Attractive 2 bedroom home in a wonderful West/Central location within walking distance to West Lake Park and all it has to offer! Maintenance free vinyl siding, newer windows, nice sized rooms throughout, completely glassed in front porch, spacious lot and quiet neighborhood! Great opportunity for home ownership.

617 W Howard Street, Winona

Listing courtesy of Edina Realty, Inc..

653 Johnson Street, Winona
$148,900
2 Beds ⋅ 1 Baths ⋅ 7110357 MLS
Cute and cozy 2 bedroom with tons of charm and character, plus it's located only 2 short blocks from Lake Park and all that it has to offer! Spacious rooms throughout, great open floor plan with a wonderful pantry off the kitchen. Large front porch featuring great morning sunshine.

653 Johnson Street, Winona

Listing courtesy of Edina Realty, Inc..

26238 County Road 17, Winona
$499,900
4 Beds ⋅ 4 Baths ⋅ 7107430 MLS
Enjoy the space and beauty of country living just minutes from Winona! Situated on 1.38 beautifully landscaped acres, this spacious two-story home offers an exceptional combination of generous living space, beautiful outdoor surroundings, and convenient access to town. Mature landscaping creates a wonderful sense of privacy while offering plenty of room to relax and enjoy the outdoors. Step inside to an inviting open-concept main level featuring a spacious kitchen, dining area, and living room centered around a beautiful three-sided gas fireplace. A versatile main-level den and full bathroom provide flexibility for a home office, guest room, or potential fourth bedroom. Upstairs, the spacious primary suite offers a walk-in closet, double vanity, jetted tub, and private deck overlooking the property. Two additional bedrooms, a full bathroom, and an open loft complete the upper level. The expansive walkout lower level features a huge family room with direct backyard access, another full bathroom, and a spacious laundry room. Outside, enjoy the beautifully landscaped grounds, covered front porch, deck, and fenced yard area perfect for pets or outdoor enjoyment. With 1.38 acres, generous living space, and a convenient location just minutes from Winona, this property offers an incredible opportunity to enjoy the benefits of country living at an exceptional value! FLOOD RISK CLARIFICATION: Despite the 9/10 third-party online flood risk rating, lender-required flood insurance does not apply to this property.

26238 County Road 17, Winona

Listing courtesy of Edina Realty, Inc..

13C Hickory Lane, Winona
$90,000
3 Beds ⋅ 3 Baths ⋅ 7104624 MLS
Beautifully updated 3 bedroom, 3 bath manufactured home offering 1,848 finished sq ft with an open and spacious layout! This home has been completely updated throughout and features new flooring, kitchen, appliances, lighting, doors, trim, paint, and much more. You’ll love the ample kitchen cabinet storage, large living spaces, and two fireplaces that make the home feel warm and inviting. Outside features a large lot with 3 spacious storage sheds and plenty of room to park a boat, trailer, or extra vehicles. Located in the scenic Country Valley manufactured home community, just minutes to town. If buyer chooses to keep the home in the park, park approval is required. Lot rent includes water, sewer, and trash. Seller is agent relative.

13C Hickory Lane, Winona

Listing courtesy of Edina Realty, Inc..

22189 Garvin Heights Road, Winona
$1,100,000
4 Beds ⋅ 5 Baths ⋅ 7099978 MLS
Set on five private acres just two minutes from Winona, this exceptional one-owner estate offers the rare combination of refined living, remarkable craftsmanship, and unparalleled functionality. With over 4,800 finished square feet, every space has been thoughtfully designed and impeccably maintained, showcasing timeless materials, custom details, and quality that stands apart. The heart of the home is a stunning great room where vaulted ceilings and expansive windows frame sweeping valley views, filling the space with natural light. Custom window coverings, rich Brazilian cherry flooring, extensive natural woodwork, handcrafted built-ins, and custom cabinetry create a warm atmosphere throughout. A formal dining room provides an elegant setting for entertaining, while the spacious floor plan offers effortless everyday living. The primary suite is a true retreat, featuring two walk-in closets and an en-suite bath complete with a soaking tub and separate shower. With four bedrooms and five bathrooms, the home offers generous accommodations for family and guests alike. There is a new walk-in-tub and shower on the second floor. The finished lower level includes a walk-out basement, a kitchenette, creating excellent potential for a private mother-in-law suite, along with a walk-in safe, abundant storage, and in-floor heat for year-round comfort. Practical luxury continues beyond the living spaces. The attached three-car garage is equipped with in-floor heat, while the impressive 79' x 49' outbuilding offers more than 3,600 square feet of versatile space. Partially heated and air-conditioned with a half-bathroom, it's ideal for collectors, hobbyists, home-based businesses, or anyone seeking exceptional workspace without compromise. Designed for low-maintenance living, the steel siding and maintenance-free deck allow you to spend more time enjoying the breathtaking valley sunsets that unfold each evening. A newer roof, installed in 2021, adds peace of mind, while the home's extraordinary level of care and attention to detail is evident at every turn. Waiting on results for Septic Compliance. Properties of this caliber, offering luxury, privacy, exceptional utility, and a location just moments from the conveniences of Winona, are rarely available. This is a home built not only to impress, but to be enjoyed for generations.

22189 Garvin Heights Road, Winona

Listing courtesy of Real Broker, LLC..

24082 Homer Valley Road, Winona
$410,000
3 Beds ⋅ 3 Baths ⋅ 7089433 MLS
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. The open main floor contains your primary bathroom ensuite with and open floor plan containing your kitchen, dining and living space. A main floor laundry and half bath round out your first floor convenience. The lower level reveals another large bedroom with double closets, full bath, and a third bedroom or office space. A generous sized attached garage leaves plenty of room for tools and other outside toys, as well as the family vehicles. Still in need of additional storage? No problem with the large storage room in the basement or powered pole shed steps from your home. A stunning yard leaves plenty of room for your family or fur family to run free. Schedule a showing today and make this your own oasis, just minutes from Winona.

24082 Homer Valley Road, Winona

Listing courtesy of RE/MAX Advantage Plus.

25020 Gull Lane, Winona
$499,900
2 Beds ⋅ 2 Baths ⋅ 7079764 MLS
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 and take in the river views, watch the wildlife, enjoy fishing and boating, or simply unwind surrounded by nature. Conveniently located just minutes from Winona and La Crosse, you’ll love having a quiet retreat without giving up everyday conveniences. A rare opportunity to own along the Mississippi River. New roof added September 2026.

25020 Gull Lane, Winona

Listing courtesy of RE/MAX Results.

661 Market Street, Winona
$1,890,000
6 Beds ⋅ 6 Baths ⋅ 7081945 MLS
This English manor contains one of the most breathtaking views in Winona, MN and is set across four city lots for privacy and space. The view of Lake Winona can be seen from almost every window on the South side of the home as light streams in from the windows. Better yet, most of the windows have been updated with Andersen 400 windows, along with a new tile roof. The home is built with stone from five different quarries, has restored wood floors and showcases both artistry and strength. The kitchen area contains a lovely coffee bar and pantry, along with an informal and formal dining room. The main level family room is cozy with a fireplace, high ceilings and a beautiful library with lovely wood structures. Upstairs contains spacious bedrooms with bathrooms for all. The lower level offers versatile gathering space with a fireplace and arched alcoves, along with extra rooms to house materials for all different types of hobbies and storage. The back, closed in patio is the perfect place to drink your morning coffee. There are several other locations to take in the view and enjoy the 170 feet of land in between the home and lake. Enjoy the manicured grounds with stone garden walls, a garden house, raised garden beds, brick walkways, shaded patios, and a fire pit area, all that provide spaces to relax or entertain. Take in the view of the nearby rose garden, lake and park. The 3 stall garage is heated with Epoxy floors. With extensive storage and thoughtfully updated systems throughout, this one-of-a-kind residence balances historic charm with thoughtful modern amenities.

661 Market Street, Winona

Listing courtesy of Real Broker, LLC..

1888 Gilmore Avenue, Winona
$259,900
3 Beds ⋅ 2 Baths ⋅ 7068974 MLS
Spacious 3-bedroom Ranch on an extra-large lot in a quiet, residential neighborhood. This home features a very practical floor plan with a large Livingroom, nice size bedrooms, great storage, a main floor family/den area off the kitchen plus a large basement with all kinds of potential! Terrific opportunity for a great home in a wonderful location. A new roof along with new soffit and facia has just been completed along with a new 100 AMP electrical panel.

1888 Gilmore Avenue, Winona

Listing courtesy of Edina Realty, Inc..

76 Rodeo Drive, Winona
$519,900
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.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Regional Multiple Listing Service of Minnesota. Real estate listings held by brokerage firms other this firm are marked with the Broker Reciprocity logo. Information Deemed Reliable But Not Guaranteed. Property locations as displayed on any map are best approximations only and exact locations should be independently verified.

Listing data © 2026 Regional Multiple Listing Service of Minnesota. All rights reserved. By searching, you agree to the EULA.

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