Oshkosh Homes with 2 Story Building Style

Welcome to Oshkosh, Wisconsin—a charming city nestled in the heart of Winnebago County, where vibrant community spirit meets stunning natural beauty. Known for its rich history and thriving cultural scene, Oshkosh is a place where you can truly feel at home. The city is beautifully positioned along the shores of Lake Winnebago, offering residents picturesque views and a plethora of outdoor activities, from boating and fishing to hiking and biking along scenic trails.

As you explore this delightful city, you'll discover a variety of architectural styles that reflect its historical roots and modern growth. One of the standout features of Oshkosh’s real estate market is the abundance of stunning two-story homes. These properties not only provide ample living space but also exude a sense of elegance and charm that many families seek. With spacious layouts, high ceilings, and inviting outdoor spaces, two-story homes in Oshkosh are perfect for those looking to create lasting memories with loved ones.

The two-story homes in Oshkosh often boast beautiful craftsmanship, blending traditional and contemporary designs. Many of these residences are situated in friendly neighborhoods, close to parks, schools, and local amenities, making them ideal for families and professionals alike. Whether you’re looking for a cozy family abode or a stylish retreat, Oshkosh's two-story homes offer a unique opportunity to experience the warmth and vibrancy of this wonderful city.

Come and discover the charm of Oshkosh—where your dream home awaits!

Newest Oshkosh Homes with 2 Story Building Style

$499,900

50331033 MLS ⋅ 3 Beds ⋅ 2 Baths ⋅ ACTIVE-OFFER NO BUMP Status ⋅ Town of Clayton Municipality

Just appraised at $510,000! Offered at $499,900, this beautiful property offers 5 wooded acres with space, privacy, and room to enjoy the outdoors. The home features 3 bedrooms plus a versatile loft, hardwood floors, first-floor laundry, and a spacious primary suite with private bath and large closet with attic access. Cozy pellet stove in the living room. LL 14x12 finished room (jus add flooring). Enjoy the deck overlooking the gorgeous, wooded setting. Attached 2-car garage plus an additional 2-car detached garage, complete with an EV plug-in. Roof 2011; furnace, A/C, water heater, and water softener all less than 10 years old. A rare opportunity to own a spacious home on a stunning 5-acre parcel!

7364 JENSEN Road, Oshkosh, WI 54904

Courtesy of Resource One Realty, LLC

OFF-D: 920-309-0550

$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

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.