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841 S Monroe Street, Waterloo
$645,000
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Enjoy country living with all the conveniences with close proximity to town. This 5.69 acre property offers you just that. From the 1st time you enter the home through either the enclosed front porch or the generous mud room off the kitchen you will feel "cozy!" The large eat-in kitchen & its built-in vintage cupboard is just waiting to be filled with the smells, tastes & sounds of home. Like to entertain?? The formal dining room that opens to the vey large living room with stone fireplace & beamed ceiling is all yours. A great open space for this age home! Speaking of age, HVAC-2 years old, roof, windows and siding all new in the last few months. That's nearly a lifetime of worry free living. 2nd floor walk-in attic for storage & a 17x10 sitting area off the living room give you even more living area. Put your personality into the paint, flooring & a few new fixtures & enjoy the country life! Light up the fireplace, snuggle in & you get to call this great country home....HOME!

841 S Monroe Street, Waterloo

Listing courtesy of The Lang Group.

255 Highland Terrace, Waterloo
$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.

120 Beech Road, Waterloo
$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.

1043 N Monroe Street, Waterloo
$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.

172 Mill Street, Waterloo
$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.

596 Portland Road, Waterloo
$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.

1003 N Monroe Street, Waterloo
$294,500
ACTIVE Status
Consider being the proud owner of a popular local business! This property offers endless possibilities. It's a turnkey coffee cafe or easily converted to whatever your future business goals may be. Located at a high traffic location that is well traveled by commuters. The business is also positioned near local shopping, schools, and sporting events. Sitting on a wonderful 1.65 acre lot that provides so many opportunities for hosting community inspired events and lots of additional parking. Ponder how the huge fenced lot can be utilized to grow your new business. Currently operating as Paradiddle's Cafe since 2019, offering delicious beverage and food options with unique indoor and outdoor seating. The building offers a 23x54 main floor footprint with a large finished lower level.

1003 N Monroe Street, Waterloo

Listing courtesy of Shorewest Realtors, Inc..

5643 Dutch Hollow Road, Waterloo
$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.

5016 Starlight Lane, Waterloo
$74,900
ACTIVE Status
This buildable lot offers a scenic setting in the Driftless Area near Cassville, with rolling terrain, wooded surroundings, and easy access to the Mississippi River. The property provides approximately 3.22 acres, giving you room to build a home or weekend retreat while maintaining a rural setting. A major benefit of the property is access to shared common areas within the subdivision. Owners can utilize wooded common ground with trails and additional space to explore, enjoy nature, and spend time outdoors. The location also provides convenient access to the recreational opportunities found throughout southwestern Wisconsin, including boating, fishing, hiking, hunting, and wildlife viewing. Cassville is nearby for everyday amenities, while the surrounding countryside offers the privacy and scenery that draw people to the Driftless Area.

5016 Starlight Lane, Waterloo

Listing courtesy of Whitetail Properties Real Estate LLC.

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.

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.