Winona County MN Homes under $500,000

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 includes 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. A spacious yard

Chad Garteski

Welcome to 718 Main St! Perfectly located near the lake, this home offers beautiful views of the soccer fields and Lake Park. Relax and take in the scenery from the upper deck or enjoy the shaded comfort of the awning attached to the garage. Currently rental certified as an owner-occupied duplex, this property provides flexibility—use it as a single-family home, maintain an in-law suite, or take

Laura Slavey Keller Williams Premier Realty

Welcome to one of Winona’s best-kept secrets! Nestled into the bluff, this side-by-side twin home offers one-level living with breathtaking views and ultimate privacy—yet you're still in town. The main floor features an updated kitchen with Cambria countertops and newer appliances, a spacious primary suite with abundant closet space, and two maintenance-free decks overlooking mature trees and

Angela Thompson Coldwell Banker River Valley, REALTORS

Nestled on nearly half an acre spanning two parcels, this standout property offers the space you’ve been craving right in the heart of Saint Charles. With 3 bedrooms and 2 bathrooms, this home delivers comfort, function, and character around every corner.The main-floor primary bedroom and main-floor laundry make daily living a breeze, while the updated kitchen is the true heart of the

Camille Hanson Counselor Realty of Rochester

One of the most striking and memorable properties in the Winona area, this architecturally designed 3-bedroom, 2 bath, 2 stall garage home sits on 5 wooded acres with sweeping views of bluffs and rolling hills. It offers exceptional privacy, clean lines, and walls of windows that bring the outdoors in. Every room feels connected to nature, with thoughtful design and generous living spaces

Alex Mayer eXp Realty

Enjoy comfort and convenience in this beautifully maintained home featuring a 3-stall heated garage with a 8-foot door, perfect for large vehicles or extra storage. Inside, you'll find wider hall and doorways and custom cabinets and doors that add both accessibility and character. Recent updates include a newer roof, carpet, refrigerator, stove, air conditioning, water heater, and gabage disposal

Laurie Mangen Keller Williams Premier Realty

Welcome to your dream home nestled just outside Winona, a residence that seamlessly blends spacious living with luxurious amenities. This stunning 4-bedroom, 3-bathroom home is designed to provide comfort, versatility, and a vibrant setting for both family life and entertaining guests.This home comes with a host of recent updates, including a brand-new roof in 2024 for your peace of mind.

Cherie Burke Keller Williams Premier Realty

Beautiful ranch home overlooking Lake Onalaska and the Mississippi River Valley. 3 bedrooms, 1 bathroom, 2 car attached garage and an additional 2 car detached garage with room for a workshop. Beautiful views in every direction. Large living room with a bay of windows that allows for an abundance of natural light to flow in. Cozy 3 seasons room overlooks the backyard and breathtaking views. Lower

Angela Wilson Gerrard-Hoeschler, REALTORS

**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

Sonja Kunce Coldwell Banker River Valley, REALTORS