Jefferson County Homes under $500,000

Welcome to Jefferson County, Wisconsin—a hidden gem nestled in the heart of the Badger State! Known for its picturesque landscapes, friendly communities, and a rich tapestry of history, Jefferson County offers a delightful blend of small-town charm and modern conveniences. With its serene lakes, lush parks, and vibrant downtown areas, it’s no wonder that families, retirees, and young professionals alike are drawn to this enchanting area.

One of the standout features of Jefferson County is its diverse real estate market, particularly for those seeking homes under $500,000. Whether you’re a first-time buyer or looking to downsize, you’ll find an array of options that cater to various tastes and lifestyles. From cozy single-family homes with sprawling yards to contemporary townhouses that offer low-maintenance living, there’s something for everyone in this price range.

Imagine waking up in a charming home surrounded by nature, where you can enjoy morning coffee on your patio while listening to the gentle sounds of birds chirping. Jefferson County boasts excellent schools, a plethora of recreational activities, and a strong sense of community, making it an ideal place to plant your roots.

Additionally, with easy access to major highways, commuting to nearby cities is a breeze, allowing you to enjoy the tranquility of county living without sacrificing convenience. Jefferson County is more than just a place to live; it’s a community where you can thrive, grow, and create lasting memories. Explore the possibilities today and discover your dream home in this vibrant Wisconsin county!

Newest Jefferson County Homes under $500,000

$495,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Situated on a serene 3-acre lot at the end of a dead-end road surrounded by fields, this move-in ready hobby farm is ready for you and your animals! The 80x40 pole shed is complete with water, electricity, box stalls and multiple doors, plus brand-new electric pasture fencing, a chicken coop and a former fieldstone smokehouse to boot! The quintessential farmhouse is brimming with character, extremely well cared for and FULL of updates from mechanicals to flooring to a metal roof! You'll love the convenient main-floor laundry, spacious dining and living areas for entertaining, plus a bright den perfect for a home office. With windows on every side, there's no shortage of natural light, beautiful countryside views and that pleasant cross breeze that truly makes a house feel like home.

N7097 Nielson Lane, Milford

Listing courtesy of Shorewest Realtors, Inc..

$310,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Your NextHome! Welcome to 117 Williams St. This inviting home offers comfortable living with an open concept living area designed for everyday enjoyment and entertaining. Featuring 4 bedrooms and 2 full baths, there is plenty of space to accommodate family, guests, or a home office. Outside, enjoy the benefits of a large lot with a deck that provides the perfect setting for entertaining, relaxing, and enjoying the outdoors. An oversized 2-car detached garage offers abundant space for vehicles, storage, hobbies, or workshop needs. Conveniently located. This property combines a spacious interior, generous outdoor space, and excellent garage capacity--making it a great place to call home.

117 William Street, Watertown

Listing courtesy of NextHome Success-Ft Atkinson.

$310,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

117 William Street, Watertown

Listing courtesy of NextHome Success.

$349,900

3 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

Pride of ownership shines throughout this spotless, move-in-ready, one-owner ranch! Offering 3 bedrooms, 1.5 baths and 1,420 sq. ft., this exceptionally well-maintained home features newer windows, a 2-car attached garage and a brand-new roof installed in August 2026. The full basement offers high ceilings and excellent potential for future finished living space, along with a transferable 10 year basement warranty; documentation is available in MLS attachments. Step outside to enjoy the spacious backyard and brick patio, ideal for relaxing, entertaining or summer gatherings. Conveniently located near schools, local parks and Rotary Park, home to community events, with easy access to downtown. A clean, solid and lovingly cared-for home ready for its next owner! Don't miss this opportunity!

521 W Ryder Street, Jefferson

Listing courtesy of Century 21 Integrity Group - Jefferson.

$215,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Rare opportunity to own 5.49 acres just within the city limits. The current home would need to be significantly remodeled both structurally and cosmetically. Another option is to build a new home. Finding a parcel with 5+ acres within the city limits is difficult to come by.

1334 Boomer Street, Watertown

Listing courtesy of Shorewest Realtors, Inc..

$315,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

3 Bedroom 1 Bath Ranch with fenced in yard recently updated with New Roof 2026, New Furnace 2022 Main Garage Door 2026, gate 2026, newer windows 2023, bath remodel 2021 and partial kitchen remodel plus large patio 2023 for you to enjoy all seasons. And interior freshly painted. Hardwood floors, tile in kitchen.

210 N Monroe Street, Watertown

Listing courtesy of Century 21 Endeavor.

$474,900

4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Distinguished by like-new craftsmanship and an enviable setting opposite a picturesque golf course and driving range, this 4-bedroom, 2.5-bathroom residence elevates everyday living. The welcoming foyer reveals a generous great room and sophisticated kitchen appointed with an expansive island, pantry and spacious dinette ready for memorable gatherings. Luxury vinyl plank flooring lends polished continuity throughout the main level, where laundry and a powder room enhance convenience. Upstairs, the serene primary suite indulges with a double vanity, private bath and walk-in closet. An oversized two-car garage accommodates vehicles and recreation gear, while the basement, featuring an egress window and bathroom plumbing, invites future expansion. Tour this exceptional home and make it yours!

781 S Dewey Avenue, Jefferson

Listing courtesy of Victory Realty Elite.

$319,000

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Welcome to this spacious 3BD/2.5BA home in a quiet Fort Atkinson neighborhood! With just over 2,000 sq ft, the main level features a bright eat-in kitchen, pantry closet, a formal dining room, and a large living room filled with natural light. The primary bedroom connects to the half bath, two more bedrooms and an updated full bath complete the main level. Downstairs, another full bath and a sizable rec room with a fireplace, built-in cabinets, projector and screen- great for entertaining or relaxing nights. The attached 2.5-car garage has additional storage or workshop space, while the fenced backyard, patio, and mature trees create privacy to enjoy evenings outside. Conveniently located near schools, shopping, and easy access to Hwy 26. Move-in ready, and waiting for its new owner!

724 Cloute Street, Fort Atkinson

Listing courtesy of EXP Realty, LLC.

$319,000

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

724 Cloute Street, Fort Atkinson

Listing courtesy of eXp Realty.

$384,900

4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Some homes just feel right, and this one is ready to welcome you. Tucked into a quiet, well-kept neighborhood, this 4-bedroom home offers the space, updates, and outdoor living you've been looking for. A NEW ROOF, FURNACE, and CENTRAL AIR add peace of mind, while the open kitchen, dining, and living areas create an easy flow for everyday life & entertaining. 3 bedrooms are on the main level, including a spacious primary suite with an ensuite bath. Out back, the 3-season room steals the show with its stamped-concrete floor flowing directly to a stamped-concrete patio. Your own spot for morning coffee, summer evenings, and weekend gatherings. Finished lower level (can also be used as a 4th bedroom), attached 2-car garage, and a spacious yard complete this home.

600 Brookstone Way, Watertown

Listing courtesy of Roots Realty, LLC.

$264,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Charming 3-bedroom ranch in Jefferson, set on a large corner lot with mature trees for privacy. The expansive living room features a natural fireplace and hardwood floors that continue into all three bedrooms. Large windows fill the home with light, and the kitchen offers plenty of cabinet space. Enjoy a private patio outside and a versatile lower-level bonus room--perfect for a theater, gym, or game room.Major updates include a new roof, renovated bathroom, retaining wall, concrete sidewalk, waterproofed basement, water heater, and basement windows. Move-in ready--come see it for yourself!

604 N Main Street, Jefferson

Listing courtesy of Lannon Stone Realty LLC.

$329,900

3 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

WELL-MAINTAINED PROPERTY WITH RECENT UPGRADES NOW AVAILABLE! New furnace, AC, and water softener! Walk inside and fall in love with the open concept living/dining/kitchen area. This property boasts 3 bedrooms and a den, perfect for a variety of needs! The lower level also features a family room, providing two living spaces! This property won't last long on the market, schedule your private showing today!

310 S Concord Avenue, Watertown

Listing courtesy of Realty Executives Platinum.

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.