Crawford County Homes under $500,000

Welcome to Crawford County, Wisconsin – a hidden gem nestled in the heart of the Driftless Region. Known for its stunning landscapes, charming small towns, and a rich tapestry of outdoor activities, Crawford County offers a unique blend of rural charm and modern conveniences. With the Mississippi River tracing its western edge, residents enjoy breathtaking views, abundant wildlife, and endless opportunities for fishing, boating, and hiking in the surrounding natural beauty.

For those looking to plant roots in this picturesque county, Crawford County boasts a diverse range of homes available for under $500,000. Whether you're a first-time homebuyer, a growing family, or seeking a peaceful retreat, you'll find a variety of options that cater to your needs. From cozy single-family homes in quaint towns like Prairie du Chien and Seneca to charming farmhouses with sprawling yards, the real estate market here is as diverse as its landscape.

Imagine waking up to the sounds of nature, sipping coffee on your porch while watching the sunrise over the bluffs. Many properties feature modern amenities while retaining that classic Wisconsin charm. With a strong sense of community, excellent schools, and a plethora of local events and festivals, Crawford County is not just a place to live; it’s a place to thrive.

Explore your options today and discover the perfect home in Crawford County, where the beauty of nature meets the warmth of community – all at an affordable price. Your dream home awaits!

Newest Crawford County Homes under $500,000

$179,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Attention Investment Entrepreneurs: This charming home features a new remodeled kitchen and bathroom in 2022, along with some updated electrical, plumbing and ductwork. Whether you're searching for your first home, a rental property, or an Airbnb investment, this property offers exceptional flexibility. The main level features a bedroom, an open-concept kitchen and living area and convenient main-floor laundry. Enclosed back porch provides extra space, while the inviting front porch adds even more functional living area. Upstairs offers two walk-through bedrooms. Exterior updates include new windows, siding, and roof in 2017. Additional features include forced-air furnace, city water/sewer and high-speed internet. Alley access and a generous backyard with plenty of room for entertaining, play, or extra parking for boats & campers. Some photos have been virtually staged with furnishings.Only blocks from St. Feriole beach area & boat landing.

619 N Michigan Street, Prairie Du Chien

Listing courtesy of RE/MAX Gold.

$229,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

4 bedroom ranch home on a large corner lot. This one has a lot to offer! Full basement, garage, fenced in yard, all appliances included and much more. This property has a large lot, 100x100! Fully fenced in yard, and has a section that you can keep your furry friend and another area for gardening and entertaining. Large 2 stall garage adds lots of storage space with extra parking. The 4 bedroom home has 3 bedrooms on the main level with a full bathroom and another bedroom downstairs and full bath. There is a 5th non-conforming bedroom in the basement and a large laundry room. Extra space in the basement for a gaming area, office, storage whatever you need. On the main level there is a great room in addition to the living room, offering lots of extra room for everyone to spread out! Some photos have been virtually staged with furniture for you to see the possibilities.

404 E Broadway Street, Prairie Du Chien

Listing courtesy of RE/MAX Gold.

$369,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status

Beautiful park like setting... Be enchanted as your drive up the wooded private driveway... 1.66 acres with views of the western country side.. If you want privacy this is it... 4 bedrooms, 3 bathrooms with a master suite with a whirlpool bath and separate shower.. Large open family room/kitchen dining area. A lovely living room and a shop utility room in lower level.. The tuck under 2 car garage and a detached garage for all your garden tools, mowers and toys.. Sellers require 24 hour notice to show .... Closing must co-inside with Sellers securing suitable housing.

37809 Maple Lane, Bridgeport

Listing courtesy of RE/MAX Gold.

$240,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Tucked away on 6 peaceful acres, this rustic 2-bedroom, 1-bath cabin is all about simple living and quiet mornings. You?ll find plenty of space for hobbies and storage with a 48?x40? pole shed, plus a 1,024 sq ft barn/workshop complete with a loft for all the extras you can?t quite part with. Out back, enjoy a screened-in sitting area where you can relax and take in the peaceful sounds of nature. There?s also a handy woodshed for keeping things stocked and ready. The property includes a holding tank, a private well, and a large water tank beside the pole shed that once helped collect rainwater from the roof to keep the lower garden happy. If you?re looking for a calm place to slow down with plenty of privacy, here it is!

11341 Columbus Drive, Freeman

Listing courtesy of Century 21 Affiliated.

$242,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Charming 4-square farmhouse offering character, updates, and potential for additional living space! This 3-bed, 1-bath home features a 2+ car garage connected by an added breezeway, a fenced yard, and included playset. Located on the outskirts of Eastman in a desirable setting off the highway on a .39 acre lot, it offers a rural feel with the benefits of village living. The large, open basement includes 2 additional laundry hookups and potential for more living space. An upstairs den could potentially become a 2nd bathroom or small bedroom. The spacious main-level laundry room offers pantry or storage potential. Updates include flooring, furnace, A/C, and water heater within 2 years; upstairs windows were replaced approximately 4 years ago. Additional improvements include a rebuilt basement wall, poured concrete patio, and new front-entry concrete. Covered front porch with composite decking adds curb appeal. Come take a look! *Note: Taxes will be determined due to parcel split.

57927 Baer Court, Eastman

Listing courtesy of Jon Miles Real Estate.

$345,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Located in Eastman, this move-in-ready property impresses with complete exterior and interior updates. Enjoy effortless living with new siding, new windows on both levels, upgraded electrical service, updated plumbing (cast iron replaced with PVC), new furnace, AC unit and water heater, and radon mitigation system. Inside, the light-filled layout features fresh flooring, an updated kitchen, modernized bathrooms, and the convenience of main-floor laundry. The finished basement offers versatile secondary space for a rec room, gym, or entertainment area, along with a bedroom and bath. Walk-out basement. Easy access to the deck through sliding glass doors in the main floor bedrooms. Step outside into your personal backyard paradise! The beautifully landscaped grounds feature an established garden, productive fruit trees, and a soothing koi pond?creating a peaceful retreat right in your own yard. Workshop, garden shed with storage below. All the work's been done! Just move in and enjoy!

108 Shanghai Ridge Road, Eastman

Listing courtesy of Keller Williams Legacy Group.

$245,000

4 Beds ⋅ 4.5 Baths ⋅ ACTIVE Status

Historic Charm with Mississippi River Views! This distinctive three-story home features 4 bedrooms, 4.5 baths, beautiful original woodwork, classic architectural details, and abundant natural light. Enjoy river views from the bright sunroom, plus a dedicated office and ample storage. The walkout lower level with private entrance offers flexible potential for additional living space, storage, or a home-based business. Classic features include a clawfoot tub and tiled shower, while the kitchen offers durable solid-surface countertops. New roof installed September 2026. A rare opportunity to own a piece of local history with incredible Mississippi River views.

148 1/2 Main Street, Ferryville

Listing courtesy of Riverstone Real Estate Services LLC.

$259,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Turn-of-the-century home with historic charm alongside modern comfort. Brazilian riverbed granite countertops in the kitchen, soaring ceilings, hardwood floors, and detailed woodwork, built-in floor to ceiling bookshelves, tall baseboards, front picture window, some windows are leaded glass, spacious bedrooms. Large front porch with a swing that overlooks the mature flower garden. Cement patio off the back porch. Newer detached 2 car garage.

409 S Wacouta Avenue, Prairie Du Chien

Listing courtesy of LPT Realty.

$415,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Escape to your own furnished cabin retreat on 11+ private acres just minutes from the Mississippi River. This inviting 3-bedroom getaway blends rustic charm with modern comfort, featuring an open living/dining area, spacious loft bedroom, main-floor bedroom, and a fully finished lower level perfect for guests. Step onto the back deck to soak in wooded views and unwind in the hot tub, or gather on the walk-out patio for grilling and summer evenings outdoors. Located on a quiet dead-end road with access to miles of UTV trails, this property offers endless recreation. Rush Creek State Natural Area is nearby, providing thousands of acres for hiking, hunting, fishing, and exploring. With strong short-term rental performance and a turnkey setup, this cabin is ideal as a personal retreat, income-producing investment, or both.

65835 Chandler Road, Freeman

Listing courtesy of Wisconsin Land and Homes LLC.

$249,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Enjoy the best of country living and riverfront recreation with this beautifully maintained 2-bedroom, 1-bath home located just outside the Village of Steuben. Built in 2023, this home offers new construction, new appliances, and the convenience of being sold fully furnished?making it an excellent option for a vacation getaway, investment property, or full-time residence. Situated on 2.35 acres, the property offers access to the scenic Kickapoo River, providing plenty of opportunities for fishing, kayaking, canoeing, and enjoying the outdoors. The home itself is not located in the floodplain, offering added peace of mind while still allowing you to enjoy the benefits of riverfront access. With its newer construction and spacious acreage, this property is ready to enjoy from day one. A great opportunity for those looking for a low-maintenance retreat, income-producing property, or a place to call home.

50244 Highway 179, Steuben

Listing courtesy of Century 21 Affiliated.

$31,500

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Property Selling at Online Auction! List price is starting bid. Property is in floodplain. Property selling as is. See documents for details of sale and information. Bidding starts October 6th, 2026 and End October 27th, 2026. See bidding and terms to bid at www.kramersales.com

114 Main Street, Gays Mills

Listing courtesy of Kramer Real Estate & Auction L.

$35,500

4 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

113 Main Street, Gays Mills

Listing courtesy of Kramer Real Estate & Auction L.

Start Your Search

Copyright 2026 WIREX Multiple Listing Service. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.