Waterloo Homes under $500,000

Welcome to Waterloo, Wisconsin, a charming city that perfectly blends small-town warmth with modern conveniences. Nestled in the heart of Jefferson County, Waterloo is known for its rich history, friendly community, and picturesque landscapes. With a population of just over 3,000 residents, this vibrant city offers a peaceful lifestyle while being just a stone's throw away from larger urban centers like Madison and Milwaukee.

Waterloo boasts a variety of recreational opportunities, including scenic parks, walking trails, and the serene waters of the Crawfish River. The local community is active and engaged, hosting seasonal events that bring residents together, from farmers' markets to summer festivals. With excellent schools and a strong sense of community, it’s no wonder families are drawn to this welcoming environment.

For homebuyers looking for affordability without sacrificing quality, Waterloo presents an impressive selection of homes under $500,000. Whether you’re searching for a charming bungalow, a spacious family home, or a cozy cottage, the real estate market here has something to suit every taste and budget. These homes often feature modern amenities, beautiful yards, and easy access to local parks and schools, making them ideal for first-time buyers, families, or those looking to downsize.

With its unique blend of rural charm and urban accessibility, Waterloo, WI, is a hidden gem for homebuyers seeking a community-focused lifestyle. Discover your dream home in this delightful city, where affordable living meets a rich tapestry of community and culture. Welcome home to Waterloo!

Newest Waterloo Homes under $500,000

$485,000

ACTIVE Status

Great opportunity to own. Whether you are first time or downsizing, live in half and let the other half pay part of your mortgage. This duplex is on a street with only 6 other buildings and offers great living at a great price. First time offered on the market and a great way to begin home ownership. 3 other duplexes are also for sale some with good solid tenants. One of the other duplexes has one side open so you can move in and start building equity right away. Need space for parents and want to them to be close...you just found the solution. This particular duplex is vacant on both sides and one side is move in ready. A little paint and maybe carpet and the other side is also ready to go too. All duplexes have had new roofs in spring of 2026 and this half of the duplex has been fully renovated this last year with flooring, cabinets and appliances-move in ready. Ask agent for availability of other duplexes.

255 Highland Terrace, Waterloo

Listing courtesy of The Lang Group.

$469,900

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status

ENDLESS POSSIBILITIES! This multi-level, 5 bedroom home provides many options. Need a mother-in-law suite or separate living area? Home office with a separate entrance? Work-from-home offices? Craft room? Exercise room? This is a classic, quality home with hardwood floors , solid wood doors, and many other great finishes. Enjoy the fenced in backyard on the Maunesha River. Come and see the house...it may fit your family or business needs perfectly.

500 Riverside Drive, Waterloo

Listing courtesy of Stark Company, REALTORS.

$339,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Bring your tools, ideas and vision! This classic farmhouse on approximately 4 acres offers a rare opportunity to create your own homestead while enjoying the conveniences of city living. This is a project property that needs a hands-on owner ready to tackle repairs, maintenance and updating throughout. Outside, you'll find wooded acreage, a large established garden area, grapevines, multiple outbuildings and lean-tos, plus plenty of room for hobbies, storage and outdoor projects. The garage features overhead doors on both the front and rear for convenient drive-through access. Enjoy a country-like setting while being just down the road from the school and minutes from downtown. Municipal water and sewer add to the convenience. If you're ready to roll up your sleeves and make a property your own, this could be the opportunity you've been looking for!

1043 N Monroe Street, Waterloo

Listing courtesy of Blackdeer Investment Group.

$295,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status

SHOWINGS START 9/19/26. Watch the seasons change over the Waterloo Wildlife area (4000 acre DNR property) which is your backdrop for this 4-bedroom, 1-bath, sturdy farmhouse on .8 acre lot. Great for entertaining. The living room is huge - make a spot for a home office, or additional dining space, or a reading corner, in addition to the seating area! The eat-in kitchen has room to work without bumping into anyone! Create the ambience that best suits your lifestyle! Convenient main-level laundry and full bath. 4x5 rear porch leads to side yard and is a great spot for kicking off those shoes after yard work. Stairs and upper level have exposed wood floors - refinish to your liking with paint or stain, or add carpeting! Perhaps you could add another bathroom upstairs? 2 smaller bedrooms share the hallway closet. Extra-large 2.5-car detached garage has its own electrical panel, making it a great space for your hobbies! Joint driveway has 1/3 shared upkeep costs.

596 Portland Road, Waterloo

Listing courtesy of Century 21 Affiliated.

$175,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Bring your ideas and make this property your own! Offering 3 bedrooms plus a bonus room, this home provides flexible space and plenty of potential for the right buyer. Step outside to a deck with space to relax or entertain, plus room to potentially add a garage. The property is ready for updates and improvements, making it a great opportunity for an investor, renovator, or buyer looking to build equity and add their own touches. Bring your vision and see the possibilities!

339 Taylor Street, Waterloo

Listing courtesy of EXP Realty, LLC.

$225,000

1 Beds ⋅ 0.5 Baths ⋅ ACTIVE Status

Beautiful location on just over 11 acres with additional common areas with access to Grant River for fishing, atv and hiking trails. The property has a cabin with electricity, shed (12x10) and a screened in porch (24X10) that is peaceful and absolutely amazing! Beautiful yard that is often frequented by deer, turkey, rabbits, squirrels, birds, and more. Cabin has a loft for bedroom, environmental toilet (no running water, pumps used for water) mini fridge, microwave, window ac, electric heat, and kitchen supplies, Comes fully furnished. Amazing hunting opportunity right out your back yard! Make this your sanctuary to make awesome memories, hunting camp, family vacation, or build your dream home! Realtor is partial owner

5643 Dutch Hollow Road, Waterloo

Listing courtesy of Tim Slack Auction & Realty, LLC-Lancaster.

$180,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status

2 story 4+bedroom with 24x34-2 car detached garage/shop with additional storage room on 1.76 wooded acres. Property sits on a bench with a view overlooking the river, boat landing & campground. Make this your next home away from home, rental or permeant lifestyle(relaxed). Seller is still doing work on property for it had been used as a rental.-More pictures to come/update.

4918 County Rd N Road, Waterloo

Listing courtesy of Tim Slack Auction & Realty, LLC-Lancaster.

$299,000

3 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

Relocation gives you the chance to finish what current and prior owners started! Huge kitchen w/solid-surface countertops & a convenient island. New stairs to UL, updated baths, new carpet in primary BR/UL hall. Detached 3+ car garage w/ metal roof, extra pressed gravel parking space. Primary bedroom on ML & 1/2 bath, 2 beds/full bath UL. Corner lot, just down the street from Waterloo Firemen's Park (60 acres of nature w/ walking paths, sports fields, concerts in the park, disc golf, weddings and local festivals). The park also has the 1911 C.W. Parker Carousel, the oldest active baseball field and the pavilion. Other recent updates: screen door to deck, water softener, dishwasher, primary bedroom paint & door (new window will be left behind for new owner to install). New smoke detectors and extinguishers. Added a new section of gutter to roofline on deck side of house, and over garage pedestrian door.

172 Mill Street, Waterloo

Listing courtesy of Century 21 Affiliated.

$302,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Meticulously maintained country home sitting on almost 1 acre of land. Many updates have been done in the last couple of years to make this move-in ready. A third room could be used as a bedroom but is non-conforming. A spacious yard allows for many activities, and the large (48x30) shed provides you with storage galore. The heated shop is spray foamed and has water. The large 14' door makes storing your large and small toys a cinch. If water recreation is your thing, you are just a short distance from the Mississippi River for fun in the sun. Set in the rolling hills of Grant County, this property gives you a taste of peaceful country living.

8295 Highway 133, Waterloo

Listing courtesy of River Ridge Realty SW LLC.

$434,500

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Welcome Home to this spacious 5 BR, 2 bath Ranch with beautiful country views, boasting a brand new roof, on the house & garage, plus all new siding on the South side of the home. This well-maintained home offers a perfect blend of comfortable living space, quality craftsmanship, & endless potential all in one .45 acre property. As you step inside you are greeted with gleaming oak hardwood floors that span the main level, adding warmth & timeless appeal. Gather around the cozy wood-burning fireplace, a perfect focal point for relaxing or entertaining. Enjoy outdoor living with two generous 12x12 decks that are ideal for outdoor entertaining. The LL features 3 finished Bedrooms, 1 full bath, & an En-Suite bath all plumbed, & ready for your finishes. The 3-car heated garage is a rare bonus, perfect for hobbyists, bonus office area, & plenty of extra storage. Looking to make it your own? Bring your imagination, and creative carpentry skills, and make this home your haven.

120 Beech Road, Waterloo

Listing courtesy of RE/MAX Community Realty.

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