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$575,000
4 Beds ⋅ 4 Baths ⋅ 7025912 MLS
Discover the incredible opportunity to own this expansive custom-built home nestled on 2.25 scenic acres in Saint Charles. Built in 1989, this one-of-a-kind property offers over 5000 finished square feet of living space, providing endless possibilities to update, personalize, and create your dream home. Inside, you'll find generous living areas, spacious rooms, and a thoughtful custom design that showcases quality craftsmanship and solid construction. While the home reflects its original style, it presents an exceptional chance for buyers to bring their vision and unlock its full potential. Car enthusiasts, hobbyists, or those needing extra storage will appreciate the impressive 1675 square foot garage, offering abundant space for vehicles, equipment, or workshop needs. Set on a beautiful 2.25-acre lot, the property provides privacy, space to roam, and peaceful surroundings while still being conveniently located in town. With its remarkable size, custom character, and incredible potential, this property is a rare opportunity you won't want to miss.

1397 Soppa Drive, Saint Charles

Listing courtesy of Edina Realty, Inc..

$575,000
4 Beds ⋅ 3 Baths ⋅ 6806417 MLS
Looking for space, privacy, and a top-tier neighborhood? Act fast—this Cobblestone Creek home checks every box! Enjoy peaceful country living just minutes from Winona, with rolling hills, beautiful scenery, and a welcoming community. This 4-bed, 2.5-bath home features an open floor plan, solid-surface countertops, walk-in pantry, and main-floor laundry. A private primary suite offers a walk-in closet and full bath. Downstairs, you’ll find a large family room, two bedrooms, and a bonus room ready for an office, gym, or creative space. Relax outdoors on the covered front porch or back patio and take in the quiet surroundings. A heated 3-car garage tops it off with comfort and storage. Opportunities in Cobblestone Creek don’t wait—book your showing today!

169 Cobblestone Lane, Winona

Listing courtesy of RE/MAX Results.

$560,000
3 Beds ⋅ 2 Baths ⋅ 6825956 MLS
Step into your own private retreat — a cozy home perfectly nestled on 34 breathtaking acres of nature’s finest offerings. A sparkling trout stream and peaceful pond create a serene backdrop for everyday living. Whether you’re an outdoor enthusiast or simply crave privacy, you’ll love the abundant space to explore, hunt, and unwind. Inside, the home welcomes you with comfort and charm, featuring a beautifully updated kitchen remodeled in 2025 with fresh finishes and thoughtful touches. Unwind in the inviting three-season porch — the perfect spot for morning coffee, evening relaxation, or taking in the surrounding views. Outside, a heated 30x40 pole barn offers endless possibilities — ideal for a workshop, storage for recreational gear, or hobby space — ready for year-round use. This is more than a home; it’s a lifestyle of tranquility, recreation, and rural luxury.

20818 Enterprise Valley Drive, Lewiston

Listing courtesy of RE/MAX Results.

$550,000
3 Beds ⋅ 2 Baths ⋅ 7023802 MLS
Discover your own private escape on 89 beautiful acres in Rollingstone, MN. This rare, one-owner property blends peaceful country living with incredible outdoor recreation. The 3-bedroom, 1¾-bath home offers multiple living spaces on the main level and in the finished basement, perfect for relaxing, entertaining, or working from home. Major updates include a new furnace and A/C installed in November 2023 and new 200 AMP service. Step outside to enjoy scenic views from the patio overlooking a small pond, with room to add fish if desired. A 1-car attached garage, additional shed, and 36x30 pole shed provide plenty of storage for vehicles, equipment, and outdoor toys. The land is the true standout—rolling terrain with north- and south-facing slopes, deep draws, and a long ridgeback. A well-established trail system offers easy access throughout the property, making it ideal for hunting, hiking, and recreation.

16191 County Road 25, Rollingstone

Listing courtesy of Richard L. Jacobson Real Estate.

$550,000
7003921 MLS
Prime 82.95± Acres in Winona County - Trophy Deer & Turkey Habitat - Discover a true whitetail hunter’s paradise just minutes from Winona and La Crescent! This 82.95± acre property offers exceptional deer and turkey hunting opportunities with a history of producing mature bucks and abundant wildlife. A thoughtfully designed trail system winds through the land, giving easy access to all corners of the property while minimizing disturbance to wildlife. Strategically placed established food plots provide year-round nutrition and ideal staging areas, making this tract highly attractive to deer and turkey throughout the seasons. Situated on a quiet dead-end road, this parcel delivers the privacy and seclusion that serious outdoorsmen value, yet remains conveniently located, near city amenities, shopping and dining. The terrain includes a mix of hardwoods, cedars and open areas that create a diverse habitat and excellent cover for game. Whether you’re looking for a weekend hunting retreat, building your dream cabin, or adding to your land portfolio, this Winona County property combines quality habitat, easy access and strong wildlife history - ready for your next season in the woods.

tbd Pine Ridge Drive, Dakota

Listing courtesy of Whitetail Properties Real Estate.

$545,000
3 Beds ⋅ 4 Baths ⋅ 7035191 MLS
Welcome to golf course living at its finest. This beautifully maintained 3-bedroom, 4-bath home sits directly on The Bridges Golf Course, perfectly positioned on the 5th Green and 6th T-Box, offering breathtaking views up and down the fairway. Designed for both everyday comfort and entertaining, the multi-level layout provides space, flow, and flexibility. You’ll love the 2-car garage, plus a dedicated golf cart garage for effortless access to the course—making it easy to enjoy a quick round or sunset drive. The primary suite features custom closet systems, while recent updates including new windows and a new roof add peace of mind. Step outside to immaculate landscaping that frames the home beautifully and enhances the serene golf course setting. One of the standout spaces is the glass-enclosed three-season room, the perfect spot to relax, take in nature, and enjoy sweeping course views throughout the year. Whether you’re hosting gatherings or enjoying quiet mornings overlooking the fairway, this home offers a lifestyle that will make you the envy of friends and family. A rare opportunity to own a move-in-ready home in one of the area’s most desirable golf course locations.

1628 Valley View Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$515,000
4 Beds ⋅ 3 Baths ⋅ 7046051 MLS
Set on 11 acres with breathtaking panoramic views, this completely remodeled 4-bedroom, 3-bath home offers quality craftsmanship and space both inside and out. The home features custom trim, doors, and beautiful woodwork throughout, along with durable LP SmartSide siding. Enjoy the incredible scenery from the covered deck or the spacious concrete patio — perfect for relaxing or entertaining. One of the standout features of this property is the newly built, impressive detached two-story, 1,200 sq. ft. garage. The upper level includes a kitchenette, office space, and a three-quarter bathroom, offering excellent flexibility for guests, a home business, hobby space, or additional living area. This is a rare opportunity to own a beautifully remodeled home on acreage with panoramic views and exceptional extra space.

33128 Hunters Lane, Winona

Listing courtesy of Edina Realty, Inc..

$515,000
4 Beds ⋅ 3 Baths ⋅ 6798704 MLS
Experience the best of riverfront living with this beautifully renovated 4-bedroom, 3-bath home offering panoramic views of the Mississippi River. Nestled on a waterfront lot with its own private dock and covered boat parking, this fully furnished home is move-in ready and packed with upgrades. Inside, you'll find all-new flooring upstairs and down, brand-new interior and exterior doors, and fully updated bathrooms featuring new toilets, vanities, sinks, bathtubs, and showers. The home boasts a new central air system with all new ductwork and forced heat for year-round comfort. Several new windows bring in natural light, highlighting the modern, refreshed design throughout. The open-concept living area leads out to a covered deck overlooking the river—perfect for relaxing or entertaining. Enjoy your evenings soaking in the hot tub, gathering around the fire pit, or taking in the panoramic water views. The fenced yard adds privacy and space for pets or kids to play. Outside, the home has been redone with new soffit, fascia, siding, and seamless gutters. A spacious 2-car attached garage provides convenience and additional storage. With every detail thoughtfully updated and the option to purchase the home fully furnished, all that’s left to do is move in and start enjoying the river life.

25578 Pelican Lane, Winona

Listing courtesy of eXp Realty.

$510,000
5 Beds ⋅ 3 Baths ⋅ 7076158 MLS
Welcome to refined ranch-style living with space, comfort, and a setting that’s hard to beat. This beautifully designed 5-bedroom, 3-bath home offers an inviting blend of quality finishes and functional living spaces, all perfectly positioned against a wide-open park backdrop for added privacy and scenic views. Step inside to a bright and open main level where rich wood flooring flows seamlessly through the living room, dining area, and kitchen, all enhanced by an impressive vaulted ceiling that creates an airy, expansive feel throughout the heart of the home. Large windows fill the space with natural light while showcasing the peaceful surroundings beyond. The thoughtfully designed main level includes a spacious primary suite complete with a private ensuite bath and walk-in closet, creating a comfortable personal retreat. Two additional bedrooms and a full bath are also located on the main floor, offering convenience and flexibility for family or guests. The kitchen and dining areas connect effortlessly to the covered deck, providing a perfect extension of the living space outdoors. Whether enjoying morning coffee, summer dinners, or simply relaxing while overlooking the expansive park views, the elevated deck offers year-round enjoyment and exceptional outdoor living. The walkout lower level expands the home’s versatility with luxury vinyl plank flooring throughout, creating a durable and stylish continuation of the living space. Two additional bedrooms, a full bath, and a large bonus area behind glass French doors provides endless possibilities for recreation, fitness, a media room, home office, or even a sixth bedroom! Sliding doors lead directly to the backyard patio, which is already equipped with electrical service ready for a future hot tub, making it easy to create your own private outdoor retreat. With its spacious ranch layout, quality finishes, walkout lower level, vaulted living spaces, and rare park-side setting, this home delivers the perfect balance of style, comfort, and functionality both inside and out.

1213 Whispering Hills Drive, Saint Charles

Listing courtesy of Re/Max Results.

$509,900
4 Beds ⋅ 3 Baths ⋅ 7073748 MLS
Step into comfort, space, and quality craftsmanship in this beautifully maintained ranch-style home located in the desirable Northern Hills neighborhood. Built in 2014, this walkout rambler offers over 3000 finished square feet designed for both everyday living and effortless entertaining. The main floor provides everything you need with an ideal layout featuring two bedrooms, main floor laundry, and stunning wood floors that add warmth and character throughout the living spaces. The spacious kitchen is truly the heart of the home, offering plenty of room for gathering with family and friends while flowing seamlessly into the open-concept living and dining areas. The walkout lower level expands your living space with two additional bedrooms, a second laundry hookup, and plenty of room for entertaining, hobbies, or relaxing. Whether you're looking for multi-generational living flexibility or simply extra convenience, this home is thoughtfully designed to meet a variety of needs. Car enthusiasts, hobbyists, and those needing extra storage will appreciate the impressive finished 910 sq ft three-car garage. Outside, enjoy the peaceful setting and all the benefits of a newer home in one of St. Charles' sought-after neighborhoods. This move-in ready home combines style, function, and room to grow - all in a fantastic location.

502 Northern Hills Trail, Saint Charles

Listing courtesy of Edina Realty, Inc..

$499,000
4 Beds ⋅ 3 Baths ⋅ 6718178 MLS
**New siding (espresso color), downspouts, gutters, and outside lights have just been completed (08/04/2025)** This beautiful 4 bedroom, 3 bath home is picturesque and is located on 10 private acres with nature and trails--and just 10 minutes from Winona. In the backyard, you will find a large 33 foot above ground pool surrounded by expansive decks, ideal for relaxing or entertaining. This home has a spacious 8 x 20 front porch for relaxing. Inside, the home features a massive open-concept kitchen, dining, and living room, anchored by a beautiful fireplace and is bathed in natural sunlight, creating a warm and inviting atmosphere throughout. This home features beautiful oak and maple floors, that were just refinished, and a large private primary suite (over 500 sq ft), and a spacious lower level family room with a custom bar and patio doors to a private patio. This home has a 2 car attached garage as well as a 24 x 24 workshop. The large fenced in yard provides a safe and spacious area for children or pets to play.

23677 County Road 23, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$494,000
5 Beds ⋅ 4 Baths ⋅ 7089929 MLS
Welcome to 217 Whispering Hills Drive in St. Charles, a beautifully updated home offering the perfect combination of space, comfort, and updates. With 5 bedrooms, 3.5 bathrooms, and a spacious 3-car garage, this property is designed to accommodate both everyday living and entertaining with ease. Set on a beautiful lot in a desirable neighborhood, this home has been thoughtfully refreshed from top to bottom. Recent improvements include a new roof, refinished hardwood floors, all new carpeting, and fresh paint throughout, creating a move-in-ready experience for its next owners. The home's mechanical systems and appliances have also been recently updated, providing peace of mind for years to come. Inside, you'll find generous living spaces, plenty of room for family and guests, and a functional layout that offers flexibility for a variety of lifestyles. Large windows bring in abundant natural light while showcasing views of the surrounding property. Step outside and enjoy the beautifully maintained yard, complete with a greenhouse perfect for gardening enthusiasts or anyone looking to extend their growing season. Whether you're relaxing outdoors, entertaining friends and family, or tending to your garden, this property offers something for everyone. If you've been searching for a spacious, updated home in St. Charles with room to grow both inside and out, 217 Whispering Hills Drive is one you won't want to miss.

217 Whispering Hills Drive, Saint Charles

Listing courtesy of Edina Realty, Inc..

$485,000
6784997 MLS
This is one of the most beautiful properties you will find in southeastern MN. This parcel combines wooded valleys, grassy pastures, natural limestone walls & rock formations, scenic overlooks and features over 2,100 feet of frontage on the headwaters of Pine Creek one of the best trout producing streams in the region. There are 30 acres of highly productive crop ground and 10 acres of grass pasture. The woods are comprised of mostly white oak, hickory, cherry and cedar trees. The terrain is such that it is easy to get around whether it be on foot or ATV. The property extends into both Winona and Fillmore counties. Because of this it qualifies for multiple build sites. It is a very convenient location just 6 miles south of the interstate and only 1 mile off paved roads. 9 miles to Lanesboro, Rushford or Lewiston. 20 miles to Winona and 30 miles to Rochester.

TBD Ponderosa Road, Peterson

Listing courtesy of Weiss Realty LLC.

$483,277
4 Beds ⋅ 3 Baths ⋅ 6769166 MLS
Country living awaits! Do not miss out on this serene home and acreage located on a quiet dead end road on the edge of the bluffs in southern Winona County. This 2000 built 4 bed, 3 bath home has a walk out basement and master suite. The great room features a floor to ceiling wood burning fireplace providing a cozy soft glow and warmth on those cool fall & winter evenings. The spacious yard includes a mature evergreen windbreak on the west side adding both protection and privacy. There are four well maintained & manicured apple trees in the yard. The back deck overlooks a colorful native wild flower prairie which is bustling with songbirds and butterflies. Deer and turkeys frequent the yard. Includes 2 stall attached garage and 32x24 detached garage. Easy commuting to Winona, La Crosse or Rochester being only 4 miles south of I-90. 8 Miles south of Lewiston, 8 miles northwest of Rushford.

32004 Hemmingway Road, Lewiston

Listing courtesy of Weiss Realty LLC.

$461,000
4 Beds ⋅ 3 Baths ⋅ 7003830 MLS
Welcome home to this newer twin home in the sought-after Valley Oaks neighborhood, where comfort, style, and low-maintenance living come together. This spacious home offers 4 bedrooms and 3 full bathrooms, designed with an inviting open-concept layout perfect for everyday living and entertaining. The main level features a cozy gas fireplace, seamless flow between living, dining, and kitchen spaces, and the convenience of main floor laundry. Retreat to the large primary suite, complete with a walk-in closet and a private bath showcasing a double vanity. Step outside to the covered deck with ceiling fan—ideal for relaxing evenings or morning coffee, rain or shine. The finished lower level adds even more living space, including a dedicated theater room perfect for movie nights or game days. Enjoy the ease of association-maintained living with snow removal and lawn care included, giving you more time to enjoy your home and ease of making travel plans.

384 Valley Oaks Drive, Winona

Listing courtesy of Real Broker, LLC..

$461,000
5 Beds ⋅ 3 Baths ⋅ 6817423 MLS
Welcome to this beautifully maintained 5-bedroom, 3-bath home set in a desired neighborhood. The main floor features an updated kitchen with Cambria countertops, a convenient main-floor laundry, and a very functional, easy-flow layout. Enjoy an inviting front room with a cozy fireplace, perfect for relaxing evenings. The upper level offers three spacious bedrooms and a bright sitting area ideal for reading, play, or a home office. The lower level includes two additional bedrooms, a bathroom, a comfortable family room, and a dedicated shop space, ideal for home projects or hobbies. The property boasts incredible curb appeal and a gorgeous backyard overlooking a pond, with frequent wildlife visitors creating a peaceful, natural setting. Outside, you’ll also find a backyard patio designed for entertaining, along with a newly redone screened-in porch and updated steps leading to the patio. A generous 2-car garage with additional storage completes the package. Move-in ready, thoughtfully updated, and located in a truly welcoming neighborhood - this home has it all.

75 Debi Lei Drive, Winona

Listing courtesy of eXp Realty.

$460,000
5 Beds ⋅ 4 Baths ⋅ 7111047 MLS
Welcome to this beautifully maintained 2.5-story home in a convenient downtown Winona location! Offering 5 bedrooms and 4 bathrooms, this home is filled with timeless character, generous living spaces, and thoughtful updates. Beautiful hardwood floors flow throughout much of the home, while the partially finished basement and finished attic provide incredible flexibility for a family room, home office, guest space, playroom, or hobby area. With room to spread out on every level, there's space for everyone. Step outside to a beautifully landscaped, fenced yard featuring a patio that's perfect for relaxing or entertaining. A detached 2-car garage offers additional storage and convenience. Recent improvements, including a newer roof and furnace, provide added peace of mind. Combining classic charm with modern updates, all in a desirable downtown Winona location close to parks, restaurants, shopping, and more, this home is ready for its next chapter.

316 Franklin Street, Winona

Listing courtesy of Real Broker, LLC..

$460,000
4 Beds ⋅ 2 Baths ⋅ 7065599 MLS
Welcome to this beautifully updated multi-level home in the highly desirable Knopp Valley. Offering 4 bedrooms and 2 bathrooms, the home features a bright and open layout with multiple living spaces designed for comfort and flexibility. A 2-car attached garage completes this exceptional property. Major exterior updates include a new roof, vinyl siding, windows, exterior and interior doors, and a new garage door. The landscaping has been completely refreshed with redesigned flower beds, boardwalks, and a new patio, along with tree removal and clearing of the back woods to enhance the outdoor setting. The 3-season gazebo has been freshly painted and updated, and is wired for a hot tub, creating a versatile outdoor retreat. Inside, every room has been freshly painted, including walls and ceilings, and new luxury vinyl plank flooring and carpet have been installed throughout. The kitchen and both bathrooms have been fully remodeled, complemented by all-new appliances. The living room has been enhanced with additional windows, and the kitchen features an expanded window for added natural light. Additional functional upgrades include new window treatments in every room and the relocation of the washer and dryer to an upper-level bedroom for added convenience.

398 Pleasant Hill Drive, Winona

Listing courtesy of Key Real Estate.

$460,000
4 Beds ⋅ 3 Baths ⋅ 6798227 MLS
This wonderfully scenic hobby farm is ideally located halfway between Winona and Rochester along the South Fork of the Whitewater River just outside of St Charles Minnesota. An extremely rare find, this property includes over 550 ft of stream frontage. The park-like yard features majestic pine trees and brightly colored hard maples along with plenty of room for a huge garden and pasture. This acreage incorporates plethora of outdoor spaces to explore. It is the ideal setting to unwind and find relaxation. The classic style farmhouse has had a number of updates through the years including a newer full height block basement with a walkout door and a cozy sunroom. The 45x30 multi-purpose barn could be used for horses, livestock or just a spot to store the toys. Half mile to hard surface roads, only 1.5 miles from downtown St Charles and only 5 miles south of Whitewater State Park.

11349 Equine Drive, Saint Charles

Listing courtesy of Weiss Realty LLC.

$450,000
2 Beds ⋅ 2 Baths ⋅ 7129433 MLS
Sold before print. Beautifully updated 2-bedroom, 2-bathroom townhome located on a quiet private drive just steps from Lake Winona and close to parks, trails, and local amenities. Inside you'll find stunning floors, a spacious layout, and a gas fireplace that creates a warm, inviting atmosphere. Complete remodel in 2023 including stunning kitchen and both bathrooms The main living spaces feature abundant natural light and custom built-ins that add character and function. Attached 2-car garage with epoxy flooring adds convenience, while updates throughout the home make it move-in ready. This property combines comfort, style, and location - an excellent opportunity to enjoy townhome living near Lake Winona.

100 Candlewood Drive, Winona

Listing courtesy of Gerrard-Hoeschler.

$450,000
4 Beds ⋅ 2 Baths ⋅ 7131239 MLS
Just steps from Lake Winona and minutes from downtown, this beautifully maintained 4-bedroom, 2-bath Victorian-era home offers the perfect combination of character, space, and peace of mind. Recent updates include a new roof, furnace, water heater, and flooring, while original woodwork and architectural details preserve the timeless character of the home. Additional highlights include a 3-car heated garage, large yard, sunroom, and spacious rooms filled with natural light. The main level features a generous kitchen with stainless steel appliances, granite countertops, and plenty of space for gathering. The large living room offers room to relax or entertain, while the sunroom provides a bright, versatile space with convenient access to the backyard and driveway. Beautiful original woodwork and a graceful staircase add warmth and character throughout the home. Upstairs, four comfortable bedrooms provide plenty of space for family, guests, or a home office. The multi-room basement adds valuable flexibility with space for an office or playroom, laundry, and abundant storage. Outside, the large yard is ideal for entertaining, outdoor dining, gardening, or simply enjoying the sunshine. The impressive 3-car heated garage provides exceptional space for vehicles, storage, hobbies, or creating an additional gathering space. With major mechanical updates already completed, buyers can enjoy the character of a classic Victorian without sacrificing the conveniences of modern living. Located near Lake Winona, downtown, shopping, dining, parks, schools, and recreation, this home offers an exceptional combination of location, updates, character, and space. Refrigerator in the basement will be staying with the home.

669 Main Street, Winona

Listing courtesy of Real Broker, LLC..

$450,000
4 Beds ⋅ 2 Baths ⋅ 7094852 MLS
Just minutes from Winona, this beautiful home sits on 1 acre, offering the perfect combination of privacy, space, and breathtaking Mississippi River views. Enjoy room to play, garden, entertain, or simply relax and take in the peaceful surroundings from your backyard. Inside, the open-concept floor plan features an updated kitchen, pantry, and stunning windows that fill the home with natural light while showcasing the beauty of every season. With 4 bedrooms, 2 updated bathrooms, and a 2-car garage, there's plenty of space for everyone. The lower level offers a laundry area, office, and a versatile bonus room that could serve as a theater room, playroom, workout space, hobby room, or whatever best fits your lifestyle. This is a rare opportunity to enjoy country-style living with convenience, comfort, and incredible views just minutes from town.

39109 Karen Court, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$450,000
5 Beds ⋅ 3 Baths ⋅ 6811277 MLS
Beautifully maintained 5-bedroom, 3-bath home in desirable Whispering Hills neighborhood (Saint Charles, MN). Meticulously cared for, this home offers beautiful landscaping and an extensive backyard for gardening, yard-games and more. An enclosed deck (13'2"x9'10" & not accounted for in the home's square footage) with separate non-enclosed grilling deck space provides extended use during the year. The home features main-floor living along with a generously sized lower level family room. The large backyard is perfect for future gardening or play-space for children. This home is ready to move into and add your own personal touches. RECENT UPDATES Include: Water Heater (2025); Kitchen and Bathroom counters, faucets, mirrors & toilets (2025); Gutter Screens (2023); New Roof (2022); Furnace & A/C (2019); Landscaping updates (2012).

325 Whispering Hills Drive, Saint Charles

Listing courtesy of Edina Realty, Inc..

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