City of Oshkosh Homes under $500,000

Welcome to Oshkosh, Wisconsin – a vibrant city nestled in the heart of Winnebago County, where charm meets opportunity. Known for its rich history and picturesque landscapes, Oshkosh offers a unique blend of small-town warmth and urban amenities, making it an ideal place to call home.

Oshkosh is renowned for its beautiful waterfront along Lake Winnebago, providing residents with stunning views and a plethora of recreational activities. From boating and fishing to walking trails and parks, outdoor enthusiasts will find plenty to explore. The city also boasts a thriving arts scene, with galleries, theaters, and cultural events that celebrate the community's creative spirit.

For those seeking to settle down in Oshkosh, the real estate market offers an inviting array of homes priced under $500,000. Whether you're a first-time buyer, a growing family, or looking to downsize, you'll discover a diverse selection of properties that cater to various lifestyles and preferences. From charming historic homes with character to modern builds featuring contemporary amenities, there's something for everyone.

Families will appreciate the highly-rated schools and safe neighborhoods, while young professionals will enjoy the vibrant downtown area filled with shops, restaurants, and entertainment options. With its friendly community atmosphere and an abundance of local events, Oshkosh truly embodies the essence of Wisconsin living.

Explore Oshkosh today and find the perfect home for you in this delightful city, where every corner has a story to tell and a community ready to welcome you with open arms!

Newest City of Oshkosh Homes under $500,000

$209,900

50333803 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

South side charmer that is located one block from South Park. 3 bedroom, 1 bath home with a main floor bedroom and full bath. 1 car garage and a screened front porch.

1422 OHIO Street, Oshkosh, WI 54902

Courtesy of First Weber Oshkosh

OFF-D: 920-233-4184

$209,900

50333801 MLS ⋅ 2 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Affordable and adorable 2 BR brick home in an incredible location nestled in cul de sac and walking distance from beach, zoo, parks and more! This home has everything you need starting with spacious living room, dining area, laminate flooring throughout. Cute kitchen has plenty of cabinetry/counter space. BRs are spacious boasting large/multiple closets. Your favorite place to relax will be the 3 season room! LL offers partially finished basement with RR. Opportunity to finished attic space! Outside - enjoy patio, fully fenced yard, and attached 1 car garage! Per seller - larger updates include: windows, roof, siding and more. 48 hour binding.

413 STEVENS Court, Oshkosh, WI 54901

Courtesy of Coldwell Banker Real Estate Group

$229,900

50333784 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Wonderful move-in ready ranch style home conveniently located near schools. Light streams in through the bay window in the living room making it warm and inviting. Entertaining and relaxing is easy out on the deck and the fenced-in backyard. The unfinished basement is awaiting your vison. Seller updates include furnace and C/A installed in 2024. Seller requests 24 hour response time on offers. Showings start 10/8.

111 N MEADOW Street, Oshkosh, WI 54902

Courtesy of LPT Realty

OFF-D: 920-810-5151

$350,000

50333762 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Rare opportunity to own a well maintained duplex offering a private, condo-like feel in each unit. Both units feature separate entrances, private garage space, in-unit laundry, and their own outdoor living areas with a patio and deck. The property has been updated throughout, including a new water heater in 2026, luxury vinyl plank flooring in the upper unit, and stainless steel appliances. A spacious backyard provides additional room to enjoy the outdoors, all while being within walking distance of Winnebago County Park. With a strong rental history the property offers flexibility for a future owner. Ideal for an owner occupant looking to live in one unit while renting the other, or an investor seeking a turnkey addition to their portfolio. Leases are currently month-to-month.

60 KOPE Avenue, Oshkosh, WI 54901

Courtesy of Acre Realty, Ltd.

OFF-D: 920-840-1355

$395,000

50333760 MLS ⋅ 4 Beds ⋅ 3 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Set in one of Oshkosh’s most desirable west-side locations, this inviting ranch offers an exceptional blend of comfort, style, & serene natural surroundings. At the heart of the home is a stunning kitchen. A welcoming sunroom provides a peaceful place to enjoy your morning coffee or take in the beauty of the seasons. The main living spaces are warm & inviting, with both a living room & spacious family room featuring a gas fireplace. The generously sized bedrooms provide comfort & flexibility, while the partially finished lower level adds even more possibilities with a bar area, additional living space, & versatile flex room. Beautiful Sawyer Creek runs along the rear lot line, creating a picturesque natural backdrop and attracting an abundance of wildlife. New roof-2025.

151 GRACELAND Drive, Oshkosh, WI 54904

Courtesy of First Weber Oshkosh

PREF: 920-527-1018

246 WYLDEWOOD Drive Unit E, Oshkosh, WI 54904

$274,900

50333731 MLS ⋅ 2 Beds ⋅ 2 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Move right in w/ no hassle living!! This one owner, and rare end unit condo is ready for you!! This home features 2 nicely sized bedrooms, 2 bathrooms, a large living room w/ gas fireplace, large kitchen with breakfast bar, sunroom, first floor laundry and a primary bedroom ensuite. There is a huge full basement w/ all the storage you could need. The basement has egress and stubbed for a 3rd bathroom for future finishing. Find comfort in the attached 2 car garage with direct access to the home. Out back is a green space and a private deck for relaxation. Low monthly condo fee includes all the luxuries you want-Basic cable, lawn care, snow removal, and grounds keeping. New Roof & Gutters! Close conveniences like health care/shopping are available. Some photos virtually staged.

246 WYLDEWOOD Drive Unit E, Oshkosh, WI 54904

Courtesy of Expert Real Estate Partners, LLC

PREF: 920-442-1100

$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

$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

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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.