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424 Valley Oaks Drive, Winona
$614,900
2 Beds ⋅ 2 Baths ⋅ 7164508 MLS
Immaculate custom-built home offering the perfect combination of luxury, comfort, and effortless one-level living! Thoughtfully designed with zero-entry access and absolutely no steps throughout, this stunning 2-bedroom, 2-bath home showcases exceptional craftsmanship and beautiful finishes. The open-concept kitchen and living area features vaulted ceilings, a cozy fireplace, and a beautifully appointed kitchen with premium Café appliances. The Café toaster oven is also staying. The spacious primary en-suite offers a walk-in closet, beautifully finished shower, heated bathroom floor, and direct access to the backyard. Enjoy year-round comfort in the inviting four-season sunroom and the peace of mind of a whole-house generator. Keyless exterior doors add everyday convenience, while the welcoming covered front porch is the perfect place to relax. An impressive three-car garage and abundant storage complete this exceptional property. Meticulously maintained inside and out, every detail has been thoughtfully taken care of. **Truly move-in ready with nothing left to do but enjoy!

424 Valley Oaks Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

557 W Sanborn Street, Winona
$199,900
3 Beds ⋅ 3 Baths ⋅ 7161005 MLS
Come take a look at this 3 bedroom, 2 bathroom home with plenty to offer! Featuring two bedrooms on the main level and a third upstairs, this home provides a flexible layout with the added convenience of two kitchens, one on each level. Several updates and improvements have been completed throughout the home, including a beautifully updated main-level kitchen with newer appliances and an updated bathroom. Outside, you'll find a nice patio along the side of the home, perfect for relaxing or entertaining, along with a convenient 1 car garage. With plenty of space and a versatile floor plan, this home offers a variety of possibilities for its next owners. Schedule your showing today and see all this home has to offer!

557 W Sanborn Street, Winona

Listing courtesy of Real Broker, LLC..

1553 Gilmore Valley Road, Winona
$299,000
3 Beds ⋅ 2 Baths ⋅ 7159615 MLS
Located in Winona's desirable Gilmore Valley, this well built 3 bedroom, 2 bathroom home offers a great combination of space, functionality, and opportunity to make it your own! The main level features comfortable living spaces, while the lower level offers additional flexibility, including a spacious third bedroom with a gas fireplace that could also serve as a family room. An additional room on the lower level, conveniently located near the recently renovated bathroom with shower, offers even more possibilities for a home office, hobby room, or potential fourth bedroom with the addition of an egress window. You'll also appreciate the window lined sunroom, nice backyard, and convenient 2 car tuck under garage. With a great location, quality construction, and plenty of possibilities, this home is ready for its next chapter!

1553 Gilmore Valley Road, Winona

Listing courtesy of Real Broker, LLC..

2197 Clinton Drive, Winona
$439,900
4 Beds ⋅ 3 Baths ⋅ 7160918 MLS
Welcome to desirable Valley View Estates! Lovingly cared for by the same owner since it was built in 1979, this exceptionally well-maintained 4-bedroom, 3-bath rambler is situated on a beautiful ¾-acre lot in one of the area’s most sought-after neighborhoods! The inviting main level features spacious living and dining areas, a cozy fireplace, three bedrooms, and two bathrooms. The fantastic walkout lower level offers an expansive family room complete with a pool table and second fireplace, an additional bedroom, and bathroom. Step outside to enjoy the beautiful backyard, offering plenty of space for relaxation and entertaining. The extensive list of improvements reflects decades of meticulous care, including a new roof in 2025, central air in 2024, furnace in 2022, Marvin replacement windows, and updated front porch and rear deck featuring maintenance-free decking and aluminum railings. A rare opportunity to own a truly cherished, one-owner home in an exceptional neighborhood!

2197 Clinton Drive, Winona

Listing courtesy of Edina Realty, Inc..

1473 Gilmore Valley Road, Winona
$674,900
6 Beds ⋅ 3 Baths ⋅ 7159002 MLS
Space, Comfort & Room to Roam on 4 Acres! This impressive 6-bedroom, 3-bath home offers an abundance of space inside and out! A major addition completed just five years ago doubled the size of the home, creating plenty of room for everyday living and entertaining. The spacious primary ensuite features a walk-in closet and relaxing soaking tub. Cozy up by one of two fireplaces and enjoy the convenience of a 4-car garage. Step outside and discover everything this beautiful 4-acre property has to offer! From the outdoor bar and greenhouse to the clubhouse and invisible dog fence, there's something for everyone in the family. Whether you love gardening, entertaining friends and family, or simply enjoying the outdoors, this property offers endless possibilities. Room to live, room to play, and room to make lasting memories!

1473 Gilmore Valley Road, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

22544 Windy Point Road, Winona
$469,900
3 Beds ⋅ 2 Baths ⋅ 7157491 MLS
Beautiful log home complemented by a durable metal roof nestled on 4 scenic acres in a picturesque location. This charming three-bedroom, 2 bath home features a spacious kitchen and inviting living room with hardwood floors and Amish handcrafted solid wood cabinetry. The primary bedroom is conveniently located on the main level and offers a walk-in closet. The lower level provides a spacious family room along with two additional bedrooms, offering plenty of room for family and guests. Enjoy the convenience of a two-car attached garage, plus a separate 12’ x 18’ shed for additional storage. Surrounded by nature and offering privacy and beautiful views, this property provides the perfect combination of rustic charm, comfort, and acreage. Professional photos will be added 10/15/26.

22544 Windy Point Road, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

54 Brickyard Lane, Winona
$498,800
2 Beds ⋅ 3 Baths ⋅ 7157901 MLS
Welcome to desirable Knopp Valley, a 55+ community! This stunning 2025-built home features high-end finishes, exceptional craftsmanship, and thoughtful design throughout. Located within walking distance of Saint Mary’s University, where you can enjoy convenient access to sporting events, musical performances, lectures, and a variety of cultural and educational activities. This fantastic neighborhood also offers walking and biking trails, convenient access through the underground tunnel, pickleball and tennis courts, green space, and a playground just steps away. Step inside to discover a beautiful open-concept design with in-floor heat in both the home and garage. Designed for comfortable one-level living, the home features extra-wide hallways and doorways for added accessibility. The gorgeous primary suite includes a beautifully finished bath with a custom ceramic tile shower featuring dual showerheads, including a rainfall showerhead. The main level also offers convenient laundry and a dedicated office. Upstairs, the spacious loft features a family room, additional bedroom, and full bath, making it ideal for guests or extended family. Plans are already in place for a potential third bedroom and additional storage. A whole-house reverse osmosis system and low-maintenance construction add to the home's appeal. Outside, enjoy a privacy-fenced yard, professional landscaping, a sprinkler system, and an oversized, heated two-car garage. Move right in and enjoy the exceptional quality, comfort, and convenience this beautiful home has to offer! An added bonus—this home can also be purchased completely furnished, offering a truly turnkey opportunity!

54 Brickyard Lane, Winona

Listing courtesy of Edina Realty, Inc..

357 Valley Oaks Drive, Winona
$625,000
4 Beds ⋅ 3 Baths ⋅ 7152307 MLS
Welcome to this exceptional 4-bedroom, 3-bath home built in 2023 and located in the desirable Valley Oaks neighborhood! Offering over 3,300 finished square feet, this beautifully designed home combines modern style, spacious living and the convenience of main-level living. The impressive great room features a vaulted ceiling and modern gas fireplace and flows seamlessly into the dining area and gorgeous kitchen with quartz countertops, a large center island, upgraded cabinetry, black stainless steel appliances and a fantastic walk-in pantry. The main level features three bedrooms, including a beautiful primary suite with a tray ceiling, generous walk-in closet and spa-inspired bath with double vanities and a luxurious walk-in shower. Laundry and all essential living facilities are conveniently located on the main level. The finished lower level provides even more room to spread out with a spacious family room, fourth bedroom, full bath and dedicated office space, plus additional unfinished space for storage. Enjoy the heated screened-in deck, perfect for relaxing or entertaining throughout much of the year, along with an attached 3-car garage. With modern finishes throughout and no updating needed, this home is truly move-in ready. Best of all, the HOA takes care of lawn maintenance and snow removal, giving you more time to simply enjoy your home!

357 Valley Oaks Drive, Winona

Listing courtesy of Edina Realty, Inc..

51 W Sarnia Street, Winona
$795,000
5 Beds ⋅ 5 Baths ⋅ 7150411 MLS
Commanding one of Winona's most coveted settings, this distinguished 1930 English Tudor blends timeless architectural presence with refined modern comfort. Set on three city lots beside 4 city-owned tennis courts, the residence captures sweeping views of Lake Winona, the Bandshell, Veteran's Park, and Sugarloaf-- an exceptional backdrop for everyday living and elegant entertaining. The all brick exterior showcases intricate masonry, Biesanz stone accents, a classic tile roof, and leaded glass windows that speak to the home's enduring craftsmanship and curb appeal. An automatic underground lawn sprinkling system help maintain the beauty of the landscaping and flower gardens with effortless ease. Inside, 5 bedrooms and 5 bathrooms are complimented by original hardwood floors, 9-foot main level ceilings, beautifully textured plaster walls, crown molding, generous room proportions and abundant storage throughout. Thoughtful updates include a quartz-appointed kitchen, custom tiled bathrooms, and a Biesanz stone upper terrace walk replaced in late fall 2025--enhance the home while preserving its character. With a stone wood-burning fireplace on each level and nearly three decades of meticulous care, this rare Tudor offer a "move-in ready" sanctuary of warmth, stature, and lasting elegance.

51 W Sarnia Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

25098 County Road 9, Winona
$799,000
4 Beds ⋅ 3 Baths ⋅ 7145333 MLS
This beautifully updated home is situated on 9.6 scenic acres, offering the perfect blend of modern comfort, space, and country serenity. The interior has been completely updated/remodeled, featuring four bedrooms, three bathrooms, with all new flooring, paint, trim, and doors throughout. The kitchen has been completely remodeled with new cabinetry, flooring, and beautiful hard-surface countertops, as well as a large 10 x 4 hard surface island. The lower level provides additional living space with a comfortable family room and a versatile flex room, currently being used as a music room. Bathrooms have been updated/remodeled also and a new electrical panel was installed. Major exterior improvements include a brand-new septic system, brand-new siding, roof, gutters, and garage doors, providing peace of mind for years to come. The spacious two-car attached garage offers convenient everyday access, while the additional 36’ x 24’ detached heated garage (with a loft) provides exceptional space for hobbies, projects, storage, or a home business. With extensive updates inside and out and nearly 10 acres of land (with trails), this move-in-ready property offers an incredible opportunity to enjoy modern living with plenty of room to spread out. Located directly across from the Cedar Valley Golf Course, you'll enjoy stunning views and the opportunity to hit the links anytime. Just minutes from both Winona and LaCrosse, this property gives you the best of both worlds -- country living with easy access to city amenities.

25098 County Road 9, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

423 W Mark Street, Winona
$209,999
5 Beds ⋅ 2 Baths ⋅ 7143190 MLS
A rare opportunity with incredible flexibility and income potential! This property offers a unique setup with 4 bedrooms and 1 bathroom throughout the main level and basement, plus a separate upper-level efficiency unit with its own small kitchen, bathroom, and private entrance. The possibilities are truly endless—live comfortably in the main home while renting the upper unit for additional income, create a great setup for multi-generational living, or utilize the property as a full investment. The home currently has a rental certificate, adding even more appeal for investors looking for an income-producing property. Whether you're an owner-occupant looking to offset your housing costs or an investor looking to maximize rental potential, this property offers the flexibility and opportunity to make it your own. Come take a look and see the possibilities!

423 W Mark Street, Winona

Listing courtesy of RE/MAX Advantage Plus.

65 E Broadway Street, Winona
$424,900
4 Beds ⋅ 3 Baths ⋅ 7136924 MLS
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-maintained home offers far more than meets the eye—space, versatility and thoughtful features you truly need to see in person to appreciate.

65 E Broadway Street, Winona

Listing courtesy of Edina Realty, Inc..

689 E Lake Boulevard, Winona
$255,000
3 Beds ⋅ 2 Baths ⋅ 7134711 MLS
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.

689 E Lake Boulevard, Winona

Listing courtesy of Re/Max Results.

351 E Sanborn Street, Winona
$255,000
3 Beds ⋅ 2 Baths ⋅ 7130964 MLS
Welcome to this inviting 3-bedroom, 2-bath home offering a comfortable layout and a convenient location close to parks, schools, downtown, shopping and dining. The spacious front porch provides a welcoming entrance and a great place to relax. The main level features a spacious dining room, eat-in kitchen with ample cabinet space, main-floor bedroom, full bathroom and convenient main-floor laundry, along with a back porch. Upstairs you’ll find two additional bedrooms and a second bathroom. Outside, enjoy a partially fenced yard, large deck and one-car garage. Additional highlights include plenty of storage throughout, forced-air heat, central air and all appliances included. A comfortable home with a functional layout in a convenient Winona location!

351 E Sanborn Street, Winona

Listing courtesy of Edina Realty, Inc..

1103 Gilmore Avenue, Winona
$273,000
3 Beds ⋅ 2 Baths ⋅ 7129104 MLS
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, and this home is one you won't want to miss.

1103 Gilmore Avenue, Winona

Listing courtesy of Pemberton RE.

149 E Lake Boulevard, Winona
$225,000
4 Beds ⋅ 2 Baths ⋅ 7130625 MLS
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!

149 E Lake Boulevard, Winona

Listing courtesy of Keller Williams Premier Realty.

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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