Oshkosh Homes under $500,000

Welcome to Oshkosh, Wisconsin – a vibrant city nestled along the picturesque shores of Lake Winnebago in Winnebago County. Known for its rich history and thriving community spirit, Oshkosh offers a unique blend of small-town charm and modern conveniences. With a population of around 66,000 residents, this city is famed for its annual events, including the EAA AirVenture, which attracts aviation enthusiasts from all over the globe.

Oshkosh is not just about its festivals and stunning lakeside views; it’s also a fantastic place to call home. The real estate market here is diverse and inviting, particularly for those seeking homes under $500,000. Whether you’re a first-time buyer, a growing family, or looking to downsize, Oshkosh has a variety of options to fit your needs. From charming historic homes with character to modern builds featuring the latest amenities, the housing landscape is as dynamic as the city itself.

Living in Oshkosh means enjoying access to excellent schools, beautiful parks, and a plethora of recreational activities, including boating, hiking, and biking along scenic trails. The downtown area boasts a delightful mix of local shops, restaurants, and cultural attractions, making it easy to immerse yourself in the community.

With affordable housing options and a welcoming atmosphere, Oshkosh is truly a hidden gem in Wisconsin. Explore the possibilities of making this vibrant city your new home, where you can enjoy a fulfilling lifestyle without breaking the bank. Your dream home awaits in Oshkosh!

Newest Oshkosh Homes under $500,000

$189,900

50333715 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Great investment opportunity located near the UW–Oshkosh campus! This duplex features a spacious 3–4 bedroom upper unit and a 2-bedroom lower unit, offering excellent rental potential in a convenient location. The lower unit is currently rented, providing immediate rental income for the next owner. All utilities are separately metered. Whether you're looking to expand your rental portfolio or occupy one unit while generating income from the other, this property offers plenty of potential in a strong rental area.

1108 CHERRY Street, Oshkosh, WI 54901

Courtesy of Expert Real Estate Partners, LLC

PREF: 920-573-1317

$349,900

50333692 MLS ⋅ 3 Beds ⋅ 3 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Welcome to this spacious and versatile ranch-style home, offering much more room than its exterior suggests. The main level features three bedrooms, including a generous primary bedroom with two walk-in closets. You’ll also find a spacious great room, a separate living room, a large kitchen, and the convenience of first-floor laundry. The expansive basement provides additional flexible space, while the tandem garage extends two cars deep and offers plenty of room for vehicles and storage. Outside, enjoy a fenced backyard, patio, and additional storage shed. Located in a beautiful neighborhood near parks and schools, this inviting home is a must-see.

135 N MEADOW Street, Oshkosh, WI 54902

Courtesy of First Weber Oshkosh

OFF-D: 920-379-6573

$189,900

50333701 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Investor alert! 4BR/2R up-down duplex close to downtown. Each unit 2BR/1BA. Lower unit features updated fixtures+receptacles & central AC, updated flooring ('24), a spacious LR & double doors to main bedroom. Kitchen w/ newer appliances ('24) & bonus dining space. Upper unit w/ HW floor in living rm & BR's. Freshly painted both units ('24). 1-stall garage & parking for at least 4 cars.

327 W 16TH Avenue, Oshkosh, WI 54902

Courtesy of Dallaire Realty

Office: 920-569-0827

$240,000

50333699 MLS ⋅ 3 Beds ⋅ 2 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Mid-century ranch w/ character features awaits your TLC & finishing touches! This 3BR/2BA home greets w/ lannon stone exterior & original paneled front door. Large LR has a pass-thru w/ hi-top seating in the dining area w/ picture window overlooking the fenced yard. Primary BR w/ sliding door access to back yard & dual-access en-suite w/ tiled shower. Beds 2 & 3 enjoy classic oak HW flooring. 2nd full bath completes the 1st floor. LL adds 600+sqft composed of a rec-room w/ built-ins & workshop or office w/ unfinished floor. 2-stall attached garage. This unique value-property won't last long, book your showing today! Property to be sold "as is". Please be advised that all offers are due by 9:00 AM on October 5, 2026. Offers will be presented to the sellers later that evening.

1530 W 7TH Avenue, Oshkosh, WI 54902

Courtesy of Dallaire Realty

Office: 920-569-0827

$135,000

50333671 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Welcome home to this charming 3-bedroom, 1-bath ranch conveniently located near the university and downtown. This home offers comfortable single-level living with a functional layout and plenty of potential to make it your own. Three bedrooms provide flexibility for guests or a home office. Enjoy easy access to shopping, dining, entertainment and all that the downtown area has to offer. Whether you’re looking for a new home, looking to downsize or searching for an investment opportunity, this well-located ranch is one you’ll want to see! Rented at $1250/month.

810 MCKINLEY Street, Oshkosh, WI 54901

Courtesy of Beiser Realty, LLC

Office: 920-582-4011

$429,900

50333678 MLS ⋅ 3 Beds ⋅ 2 Baths ⋅ ACTIVE-NO OFFER Status ⋅ Town of Algoma Municipality

Come home. Home in the quiet, tucked away, highly desirable Olde Apple Acres neighborhood that, designed without sidewalks to maintain and without streetlights, gives a peaceful country essence but is conveniently close to Oakwood School, Jones Park, healthcare, shopping, groceries, and really all you need. A 2010 construction ranch with Energy Star features has a layout that feels right - Main floor laundry room, a sweet landing space perfect for jackets, snow pants, boots etc, a tucked away primary suite with walk-in shower and walk-in closet, a living room with vaulted ceilings and a cozy fireplace for those upcoming chilly fall nights, and a wide open unfinished basement with endless possibilities. Generous 3-car garage. Lower Town of Algoma property taxes. Schedule your showing today!

3875 DUCHESS Lane, Oshkosh, WI 54904

Courtesy of Roots Real Estate LLC

dave@rootsrealestatellc.com

$160,000

50333675 MLS ⋅ 4 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Welcome to this 4-bedroom, 1-bath home offering plenty of space in a convenient location close to the university and downtown. The flexible floor plan provides room for bedrooms, a home office or additional living space to fit your needs. Enjoy easy access to local restaurants, shopping, entertainment, campus activities and everything downtown has to offer. Whether you’re looking for your first home, need a little more room or are searching for a property in a great location, this home offers plenty of possibilities. Come take a look and imagine making it your own! Home is rented at $1800/month.

731 SCOTT Avenue, Oshkosh, WI 54901

Courtesy of Beiser Realty, LLC

Office: 920-582-4011

$170,000

50333670 MLS ⋅ 4 Beds ⋅ 2 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Welcome to this spacious 4-bedroom, 1.5-bath two-story home conveniently located near the university and downtown. Fresh updates throughout include new LVP flooring, carpet and paint, giving the home a clean, refreshed feel. With plenty of room to spread out, the functional layout offers comfortable living spaces and four bedrooms with flexibility for guests, a home office or hobbies. The two-story design provides separation between living and sleeping areas, while the additional half bath adds everyday convenience. Just minutes from campus, downtown shopping, dining, entertainment and other local amenities. Whether you're looking for a place to call home or an investment opportunity, this property offers space, updates and a convenient location. Home is rented at $1700/month.

826 MCKINLEY Street, Oshkosh, WI 54901

Courtesy of Beiser Realty, LLC

Office: 920-582-4011

$125,000

50333665 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Enjoy convenient one-level living in this 3-bedroom, 1-bath ranch located close to the university and downtown. The ranch-style layout offers a practical floor plan with all three bedrooms and the full bath on the main level. With easy access to campus, downtown shopping, dining and local amenities, this home puts you close to everything while offering the simplicity of single-story living. Whether you’re looking for a place to call home or an investment opportunity, this property offers plenty of possibilities. Schedule your showing today! Rented for $925/month.

814 MCKINLEY Street, Oshkosh, WI 54901

Courtesy of Beiser Realty, LLC

Office: 920-582-4011

$155,000

50333662 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Great investment opportunity near the university and downtown! This upper/lower duplex offers two separate one-bedroom units, making it a great option for an investor or owner-occupant. The lower unit has been refreshed with new LVP flooring and fresh paint, creating a clean, updated living space. Each unit features one bedroom with its own living area, kitchen and bath. Conveniently located close to the university, downtown, shopping, dining and other local amenities. Whether you’re looking to add to your rental portfolio or live in one unit while renting the other, this duplex offers plenty of possibilities in a convenient location.

813 CHERRY Street, Oshkosh, WI 54901

Courtesy of Beiser Realty, LLC

Office: 920-582-4011

1757 MARICOPA Drive Unit C, Oshkosh, WI 54904

$165,000

50333656 MLS ⋅ 2 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Offered fully furnished with a full appliance package for an easy transition into simpler condo living. This updated Oshkosh condo offers comfortable living with a full appliance package and a detached one car garage. Previously used as a rental, the condo offers options for personal enjoyment or potential rental use (subject to condo rules). Looking for an easier move? The seller is willing to sell the unit fully furnished, making this an appealing opportunity to settle in with less effort. Updates, everyday convenience, and furnishing flexibility come together in one inviting package. Easy access to Westhaven Golf Course, shopping, EAA, Aurora & Ascension hospitals, YMCA and highways.

1757 MARICOPA Drive Unit C, Oshkosh, WI 54904

Courtesy of First Weber, Inc.

$207,500

50333647 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Warm, inviting + full of character, this Oshkosh home has charming features throughout. Hardwood floors, rich original woodwork + built-ins give the home a true classic feel, while the living & dining areas flow naturally together. The kitchen offers plenty of cabinetry + comes complete with appliances. Two first-floor bedrooms provide flexibility, while upstairs you’ll find a spacious third bedroom + additional flex space. The sunny enclosed front porch is the perfect spot to kick back & relax. Out back, enjoy a fenced yard with room for the dog, a garden or nights around the fire pit. Add a detached garage + convenient city location, and you’ve got a home with plenty to love. Home has a Shared Driveway.

935 W 8TH Avenue, Oshkosh, WI 54902

Courtesy of LPT Realty

OFF-D: 920-810-5151

Start Your Search

Information received from other 3rd parties: All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Neither listing broker nor Century 21 Ace Realty nor RANW MLS shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless.

Last updated .

Information provided exclusively for consumers' personal, non-commercial use, not to be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

IDX Data Source: RANW MLS

Listings courtesy of RANW MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.