City of Oshkosh Homes with 2 Story Building Style

Welcome to Oshkosh, Wisconsin—a vibrant city nestled on the shores of Lake Winnebago, renowned for its rich history, diverse community, and stunning natural beauty. As the county seat of Winnebago County, Oshkosh boasts a perfect blend of small-town charm and urban convenience, making it an ideal place to call home. Whether you're drawn to the scenic waterfront, the lively downtown scene, or the abundance of parks and recreational activities, Oshkosh has something for everyone.

One of the most captivating aspects of the Oshkosh real estate market is the availability of beautiful two-story homes. These residences offer an elegant and spacious living experience, perfect for families or those who appreciate a bit of extra room. With their classic architectural designs and modern amenities, two-story homes in Oshkosh provide the perfect backdrop for both entertaining guests and enjoying cozy family evenings. Many of these homes feature large living areas, expansive kitchens, and inviting outdoor spaces, allowing you to create lasting memories with loved ones.

Oshkosh is not just about beautiful homes; it’s also a community that thrives on culture and connection. The city hosts numerous events throughout the year, including the famous EAA AirVenture, which attracts aviation enthusiasts from around the globe. With top-notch schools, friendly neighborhoods, and easy access to recreational activities, living in a two-story home in Oshkosh means embracing a lifestyle filled with opportunity and joy.

Discover the charm of Oshkosh and find your dream two-story home today—where comfort, community, and culture come together in perfect harmony!

Newest City of Oshkosh Homes with 2 Story Building Style

$425,000

50330921 MLS ⋅ 5 Beds ⋅ 4 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

FIVE BEDROOMS + A MAIN-FLOOR PRIMARY IN WESTHAVEN GOLF COMMUNITY! This is a floor plan that gives you room to spread out, with 5 bedrooms, 4 full baths and a dedicated home office all above grade. The main level centers around a spacious eat-in kitchen with island, walk-in pantry and plenty of storage, opening to the family room with gas fireplace and patio access. The primary suite is also on the main floor with a large walk-in closet, dual sinks, jetted tub and separate shower. A full bath, office and laundry round out the first floor. Upstairs is where this layout really stands out; four generously sized bedrooms with connecting baths giving everyone their own space. The unfinished basement leaves plenty of room for storage or future finished space.

1325 S WESTHAVEN Drive, Oshkosh, WI 54904

Courtesy of RE/MAX 24/7 Real Estate, LLC

Office: 920-734-0247

$425,000

50330911 MLS ⋅ 3 Beds ⋅ 4 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Beautifully updated with custom touches throughout! The main level shines with hardwood floors, new doors & trim, charming arched doorways and a stunning kitchen with quartz countertops, large island and abundant cabinetry. The living room features a fireplace framed by custom built-ins and plantation shutters. Custom board-and-batten feature walls add character, while the spacious primary suite offers a vaulted ceiling, walk-in closet and dedicated bath with dual sinks and marble countertops. The newly finished lower level adds a large rec room, bar and full bath. Main-floor laundry & pantry, insulated/drywalled garage and a fully fenced backyard with patio, shed and separate garden complete this impressive home! Showings start 8/14

1520 WELLINGTON Drive, Oshkosh, WI 54904

Courtesy of Keller Williams Fox Cities

OFF-D: 920-224-3061

$215,000

50330910 MLS ⋅ 3 Beds ⋅ 1 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Welcome home to this charming three bedroom, one bath two story home! The main level features a comfortable living room, dining room, office or flex room, a spacious kitchen with island, and a full bathroom with convenient main floor laundry. An open staircase leads upstairs to three bedrooms and a finished attic area offering additional living space or storage. Outside, enjoy the partially fenced, spacious yard perfect for relaxing, entertaining, or enjoying the outdoors. A great opportunity to make this home your own!

1215 GRAND Street, Oshkosh, WI 54901

Courtesy of Coldwell Banker Real Estate Group

$199,900

50330774 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

What a great income generating opportunity! This upper duplex is ready for its next owner. This property offers two great units with front and back stairwells, shared basement access with separate laundry hookups, all separate metered water, gas and electric. Tenants are responsible for lawn care and snow removal. Overall two clean units with great rental history. 24 hour notice required for showings. Schedule your showing today!

622 GRAND Street, Oshkosh, WI 54901

Courtesy of Keller Williams Green Bay

PREF: 920-209-5887

$289,900

50330625 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Spacious upper/lower duplex in Oshkosh offering a great opportunity for an owner-occupant or investor. Recent updates include flooring, fresh paint, and an updated bathroom, giving the property a refreshed feel while maintaining plenty of room throughout both units. The lower unit is currently vacant, providing flexibility for a new owner to occupy or select their own tenant. Whether you’re looking to add to your rental portfolio or offset your mortgage with rental income, this duplex offers plenty of potential.

685 FRANKLIN Street, Oshkosh, WI 54901

Courtesy of Real Broker LLC

$184,900

50330661 MLS ⋅ 2 Beds ⋅ 2 Baths ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

This cute home offers a warm welcome with a great location, a beautiful kitchen and spacious bedrooms! Updates sprinkled throughout this one is hard not to look at! The 2 car garage and wide driveway on this home is a bonus! The back porch is made for fall hangouts! New flooring on the main level and hardwood floors upstairs! Main floor laundry hook ups! Fenced in yard and walking distance to downtown oshkosh and Menominee Park. Seller will have someone look at the HVAC to determine whats wrong.

831 WINNEBAGO Avenue, Oshkosh, WI 54901

Courtesy of RE/MAX 24/7 Real Estate, LLC

Office: 920-734-0247

$240,000

50330652 MLS ⋅ ACTIVE-OFFER NO BUMP Status ⋅ City of Oshkosh Municipality

Beautiful brick American Four Square with Italianate influence, filled with timeless character and versatility. The main residence features a large kitchen with a brand-new KitchenAid appliance suite, gorgeous split staircase, spacious primary bedroom, 2-car attached garage, and charming architectural details. The main level is dedicated to living and entertaining, with 3 bedrooms and a full bath upstairs. Technically a duplex, the private second unit is located above the garage and separated by staircase. Ideal as a primary residence with mother-in-law suite, guest quarters, extended living space, or income-producing rental. So many possibilities!

303 E PARKWAY Avenue, Oshkosh, WI 54901

Courtesy of First Weber Oshkosh

PREF: 920-379-7873

$194,900

50330590 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Excellent turnkey investment opportunity with this fully occupied duplex generating $2,400 in gross monthly rental income! Both units are well maintained, with the main floor unit featuring a beautifully remodeled bathroom and additional updates throughout. Tenants will appreciate the large side yard and detached 2-car garage, providing ample outdoor space and convenient parking. This income-producing property offers immediate cash flow from day one, making it an excellent addition to any investment portfolio. Conveniently located with strong rental appeal, this is a rare opportunity to purchase a fully leased duplex with updates already completed and stable rental income in place.

1213 GRAND Street, Oshkosh, WI 54901

Courtesy of Coldwell Banker Real Estate Group

$249,900

50330586 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Exceptional investment opportunity with this fully turnkey remodeled triplex offering immediate income potential! All three units have been remodeled, allowing the next owner to lease at current market rents from day one. Recent improvements include 3 brand-new water heaters (Spring 2026) and a new furnace (Spring 2026) for added peace of mind. Property offers parking space for up to 4 vehicles, a common-area coin-operated laundry, and separate gas, water, and electric meters for each unit, helping minimize landlord utility expenses. Conveniently located near UW-Oshkosh, this is a rare turnkey investment ready to generate income immediately.

840 JACKSON Street, Oshkosh, WI 54901

Courtesy of Coldwell Banker Real Estate Group

$174,900

50330496 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Discover the possibilities with this well-positioned Oshkosh duplex! Ideal for investors or buyers seeking income potential, each unit offers 2 bedrooms, 1 full bath, separate entrances, and in-unit laundry. The lower unit is leased at $750/month through 1/31/2027, while the upper unit rents for $750/month on a month-to-month basis. Numerous seller updates over the years. Conveniently located near schools, parks, dining, and everyday amenities, with off-street parking and a detached garage adding extra convenience. Property is being sold AS-IS; FHA/VA financing may present challenges, so buyers should verify property eligibility with their lender prior to submitting an offer. Allow sufficient notice for tenant-occupied showings.

843 W 9TH Avenue, Oshkosh, WI 54902

Courtesy of Keller Williams Fox Cities

PREF: 920-312-7391

$259,900

50330448 MLS ⋅ 4 Beds ⋅ 2 Baths ⋅ ACTIVE-OFFER NO BUMP Status ⋅ City of Oshkosh Municipality

Brimming w/ character and charm, plus ideally located between the University of Wisconsin Oshkosh and vibrant Downtown Oshkosh - this home is something you will want to see! Welcoming front sitting porch sets the tone, while original hardwood floors, freshly painted interior, and classic architectural details create warmth throughout. Home offers generously sized bedrooms and two baths w/ plenty of space to live, work from home, or entertain. Outside, enjoy a private fenced backyard perfect for play, pets, or outdoor gatherings. A wonderful opportunity to own a home in a convenient, walkable location close to campus, restaurants, shopping, and more!

238 W IRVING Avenue, Oshkosh, WI 54901

Courtesy of First Weber Oshkosh

CELL: 920-203-3047

$235,000

50330420 MLS ⋅ ACTIVE-NO OFFER Status ⋅ City of Oshkosh Municipality

Don't miss this excellent investment opportunity just minutes from the University of Wisconsin–Oshkosh. This well-maintained duplex is ideal for investors looking to generate rental income or owner-occupants who want to live in one unit while renting the other. The upper unit boasts 3 bedrooms, 1 bathroom, a spacious living area, a bright kitchen with tons of cabinets and enclosed porch. The lower unit includes 2 bedrooms, 1 bathroom, a comfortable living room and functional kitchen with tons of cabinets and an enclosed porch (this unit is occupied through March 2027) Located in a desirable area close to UW Oshkosh, shopping, restaurants, parks, and public transportation.

687 CENTRAL Street, Oshkosh, WI 54901

Courtesy of First Weber Oshkosh

PREF: 920-527-1018

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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.