Oswego Homes under $400,000

Welcome to Oswego, Illinois – a charming village that beautifully blends suburban tranquility with vibrant community life. Nestled in Kendall County, Oswego is known for its picturesque landscapes, friendly neighborhoods, and a strong sense of community. With a rich history dating back to the mid-1800s, this delightful town has evolved into a sought-after destination for families, young professionals, and retirees alike.

Oswego boasts an array of amenities that cater to all lifestyles. Enjoy leisurely strolls along the Fox River, explore the scenic parks, or indulge in shopping and dining at local boutiques and eateries. The town is also home to exceptional schools, making it an ideal place for families looking to settle down in a nurturing environment. With a variety of community events and festivals throughout the year, residents find ample opportunities to connect and create lasting memories.

For those seeking their dream home in Oswego, you'll be pleased to discover a diverse selection of properties available for under $400,000. Whether you're looking for a cozy single-family home, a modern townhouse, or a charming vintage property, Oswego has something to suit every taste and budget. The housing market offers great value, allowing first-time buyers and growing families to find their perfect abode without breaking the bank.

With its welcoming atmosphere, excellent amenities, and affordable housing options, Oswego is more than just a place to live – it's a community where you can thrive. Come experience all that Oswego has to offer and discover why so many are proud to call this vibrant village home!

Newest Oswego Homes under $400,000

$285,000

2 Beds ⋅ 2 Baths ⋅ 12771710 MLS ⋅ NEW Status ⋅ Churchill Club BLDG.

Welcome home to this beautiful 2-bedroom, 1.5-bath townhome located in the highly desirable Churchill Club community! Perfectly positioned backing to the community walking path, this home offers extra yard space and added privacy-a wonderful setting to relax and enjoy the outdoors. Step inside to a bright, open-concept layout featuring 9-foot ceilings and large windows that fill the home with natural light. The spacious kitchen offers 42-inch cabinetry and flows seamlessly into the separate dining area-perfect for everyday meals, entertaining friends, or hosting family gatherings. The inviting family room provides plenty of space to unwind while enjoying the bright and airy atmosphere. Upstairs, the spacious primary bedroom features a vaulted ceiling and two separate closets for ample storage along with a full bathroom with generous storage. Down the hall is the second bedroom and a versatile loft area-ideal for a home office, workout space, playroom, or cozy reading nook. Enjoy all that Churchill Club has to offer! This sought-after clubhouse community features multiple pools, parks, tennis and basketball courts, a fitness center, sled hill, miles of walking paths, and more. Plus, enjoy the convenience of being within walking distance of the on-site preschool, elementary school, and junior high. A beautiful home, fantastic amenities, and a welcoming community-all ready for its next owner!

403 Bluegrass Parkway, Oswego

$290,000

3 Beds ⋅ 3 Baths ⋅ 12729821 MLS ⋅ NEW Status

Welcome home to this beautifully maintained 3-bedroom, 2.5-bathroom two-story condo! As an end unit, this home offers added privacy and peaceful views from your patio that backs up to a tree lined setting. The bright, inviting main level features durable laminate flooring and a well-appointed kitchen with stainless steel appliances. Upstairs, you'll find three comfortable bedrooms, including a spacious primary suite with walk in closet. Enjoy the ease of an attached garage and the low-maintenance lifestyle condo living provides. With a desirable layout, great natural views, and plenty of space to call your own, this home is a must-see! Many updated done including: new Carpet 2024, New washer and dryer 2025, new dishwasher 2025, new garage door opener 2024, new nest theromstat 2026, garbage disposal 2021, and roof in 2018.

109 Waterbury Circle Unit #109, Oswego

$375,000

3 Beds ⋅ 3 Baths ⋅ 12778398 MLS ⋅ NEW Status

Welcome to 16 Sherwick Rd, a spacious and inviting 5-bedroom, 3-bathroom home nestled on a quiet street in Oswego, offering an open floor plan, abundant storage, and a peaceful setting surrounded by mature trees. This home offers a versatile layout designed for comfortable everyday living and entertaining. The main level features a bright living room, dining area, and kitchen with an eating area, breakfast bar, center island, and pantry, creating a welcoming space for gatherings. Three bedrooms are conveniently located across the main level, while the basement provides additional living space and two more bedrooms, offering excellent flexibility for guests, a home office, hobbies, you name it! Numerous improvements enhance the home's comfort and appeal. New luxury vinyl plank flooring was installed throughout most of the main level in June 2026. The main bathroom was updated and the main living areas received new paint in June 2026. A 6-foot cedar privacy fence was added in March 2025, creating a private outdoor setting, while all main-level windows were replaced in June 2025 with a transferable warranty to the next owner. Enjoy an exceptional location close to everyday conveniences and recreation. The home is mere minutes to the Civic Center and its pool and is less than a five-minute drive to the community center with indoor pool, golf course, Fox River, and downtown Oswego. Costco and Sam's Club are approximately 10 minutes away. Residents will also appreciate access to highly regarded local schools. This home combines a desirable location, thoughtful updates, flexible living space, and a peaceful neighborhood setting. Schedule your showing today!

16 Sherwick Road, Oswego

$144,900

1 Beds ⋅ 1 Baths ⋅ 12775718 MLS ⋅ ACTIVE Status

PRICED TO SELL, NOT A SHORT SALE, GREAT OPPORTUNITY TO OWN YOUR OWN PLACE, NO MORE RENTING, ONE BEDROOM CONDO, NICE LIVING ROOM SPACE W/SLIDE GLASS DOOR, NICE BALCONY TO ENJOY THE OUTSIDE BREEZE.

2000 Light Drive Unit #211, Oswego

172 Presidential Boulevard Unit #172, Oswego

$324,000

3 Beds ⋅ 2 Baths ⋅ 12775742 MLS ⋅ ACTIVE Status

Ready to move in 3 bedroom, 1.5 bath recently upgraded house with wood laminate floors in living and dining area. New carpet, new appliances and new bathrooms and paint.

172 Presidential Boulevard Unit #172, Oswego

$325,000

2 Beds ⋅ 3 Baths ⋅ 12775485 MLS ⋅ ACTIVE Status

READY TO OWN YOUR OWN PROPERTY? COME SEE THIS WONDEFULL TOWNHOME TRULY READY TO MOVE IN, 2 BEDROOM, 2.1 BATH, QUIET CUL-DE-SAC, OPEN VAULTED CEILING, 2 STORY LIVING ROOM WITH A FIREPLACE, VERY NICE KITCHEN, VERY WELL TAKEN CARE OF UNIT. COME SEE IT TODAY.

419 Prairieview Drive, Oswego

$379,990

3 Beds ⋅ 3 Baths ⋅ 12775477 MLS ⋅ ACTIVE Status

Discover yourself at 2277 Barbera Dr., Oswego, Illinois, a beautiful new home in our Sonoma Trails community. This END UNIT townhome is ready for fall move-in! Homesite includes a fully sodded yard that is maintained throughout the year as well as snow removal in the winter. This Norfolk townhome plan offers over 1,500 square feet of living space with 3 bedrooms plus a loft, 2.5 baths, a mudroom and a 2-car garage. As soon as you step inside, you'll be greeted by our open concept living area, featuring luxury vinyl plank throughout the main living areas. The expansive kitchen overlooks the dining and great room areas, making it the ideal space to entertain. Additionally, your kitchen features designer 42-inch cabinetry, a spacious island with quartz countertops, and pantry. Enjoy your large primary bedroom with a walk-in closet and connecting en suite bathroom. The rest of the upper level features a laundry room, secondary bedrooms with a full second bath, and linen closet. You'll find luxury vinyl plank flooring throughout the main level living space, bathrooms, and laundry. All Chicago homes include our America's Smart Home Technology. Exterior and interior Photos are of similar home and model home. Actual home built may vary.

2277 Barbera Drive, Oswego

$355,000

3 Beds ⋅ 3 Baths ⋅ 12768994 MLS ⋅ ACTIVE Status

Wow! This Seasons at Southbury townhome is better than brand new! Enjoy the courtyard view! Just built in 2022, you've got all the goodies that were upgraded such as the wrought iron spindles on the staircase, LVP flooring on the main level, recessed lighting, 42" kitchen cabinets and gleaming quartz counters. Modern smart home features - plus seller has added blinds throughout, new hardware on the cabinets, ceiling fan in the primary and a wash basin in the lower level laundry room! The sunny living room flows right into your oversized kitchen and breakfast room. It features gorgeous rich mocha cabinetry, a hall closet, a pantry closet, all stainless steel appliances and direct access to your spacious balcony! Upstairs, your primary suite is a true retreat with a ceiling fan, an incredible walk in closet and a wonderful en suite with a dual sink vanity, huge shower and private water closet. The 2 additional bedrooms on this level are bright and sunny and have excellent closet space. There is an additional full bathroom on this level! In the lower level, you will find an excellent bonus room for the perfect den or work from home space, tons of additional storage in the closet and under the stairs, and a large mudroom equipped with a wash basin and storage shelves. This home is Wi-Fi certified it boasts Smart Home Automation technology, a wireless touch entry, and a video doorbell. This is such an amenity rich subdivision, you'll never run out of activities to do! You're just a few steps to the gorgeous clubhouse/exercise facilities and pool, tennis courts, walk to the elementary school, stroll for miles on the paved walking paths, enjoy the parks throughout and so much more. This location also features additional guest parking right out back. Walk on up into your new townhome today, it's turn key ready for you!

403 Shadow Court, Oswego

$345,000

3 Beds ⋅ 3 Baths ⋅ 12773366 MLS ⋅ ACTIVE Status

Stylish, smart and thoughtfully designed for the way you live - this Prescott Mills tri-level offers the space, updates and low-maintenance lifestyle you've been looking for. Offering over 1,700 square feet, 3 bedrooms, 2.5 bathrooms and a low HOA, this townhouse delivers an ideal blend of comfort and convenience in one of Oswego's sought-after communities. Inside, the main level immediately feels warm and inviting with beautiful hardwood floors and an updated kitchen designed to balance style with everyday function. Trend-forward gray cabinetry, granite countertops, and black stainless steel appliances create a polished space that's equally suited to morning coffee or entertaining friends. With granite countertops carried through the bathrooms, the home offers a consistent level of thoughtful updating throughout. Upstairs is where you'll find your private retreat. Brand new carpet extends throughout all three bedrooms, including an oversized primary suite featuring a generous walk-in closet and private ensuite bath with dual sinks. Two additional bedrooms provide flexibility for family, guests or a dedicated workspace. The lower level adds even more versatility with wood-look Italian tile and a spacious flex room ready to adapt to your lifestyle - think cozy family room, home office, hobby studio or playroom. And the details behind the walls are just as appealing. The home is hardwired for internet and equipped with smart switches and a smart thermostat, making everyday living a little more connected and convenient. In the heated garage, an overhead storage rack system provides valuable organization without sacrificing parking or floor space. Outside, the setting is equally inviting. Step into the quiet common courtyard or follow the connecting walking paths toward serene pond views. Townsend Park is right within the subdivision, while shopping, dining, recreation and everyday conveniences are all close by. Located within Oswego School District 308, this is a home that makes an especially compelling first step into homeownership - with the space to grow, the updates to enjoy, and the low-maintenance lifestyle to make it easy. Opportunities to find this combination of space, smart features, peaceful surroundings, and a low HOA don't come along every day. Come see how naturally this one fits your lifestyle.

234 Devoe Drive, Oswego

$348,500

2 Beds ⋅ 3 Baths ⋅ 12771031 MLS ⋅ ACTIVE Status

Spacious, end unit and light-filled townhome offering versatile living space in Oswego! The main level features an open and airy layout with soaring vaulted ceilings, abundant natural light and a spacious primary bedroom conveniently located on the main floor. The kitchen features warm wood cabinetry, stainless-steel appliances, tile backsplash, ample counter space and hardwood flooring, with easy flow into the living and dining areas. Enjoy additional outdoor living space on the private balcony. The lower level offers a second bedroom, full bath and a generously sized family room providing excellent flexibility-the family room could potentially be enclosed with drywall and a door to create an additional private room, home office or flex space. Extra sized two car attached garage and ample storage add everyday convenience. A spacious and flexible floor plan with plenty of possibilities-come see everything this Oswego townhome has to offer!

250 Devoe Drive, Oswego

$363,990

3 Beds ⋅ 3 Baths ⋅ 12770841 MLS ⋅ ACTIVE Status

Discover yourself at 2256 Bodega Dr., Oswego, Illinois, a beautiful new home in our Sonoma Trails community. This END UNIT townhome will be ready for a fall move-in! Homesite includes a fully sodded yard that is maintained throughout the year as well as snow removal in the winter. This Norfolk townhome plan offers over 1,500 square feet of living space with 3 bedrooms plus a loft, 2.5 baths, a mudroom and a 2-car garage. As soon as you step inside, you'll be greeted by our open concept living area, featuring luxury vinyl plank throughout the main living areas. The expansive kitchen overlooks the dining and great room areas, making it the ideal space to entertain. Additionally, your kitchen features designer 42-inch cabinetry, a spacious island with quartz countertops, and pantry. Enjoy your large primary bedroom with a walk-in closet and connecting en suite bathroom. The rest of the upper level features a laundry room, secondary bedrooms with a full second bath, and linen closet. You'll find luxury vinyl plank flooring throughout the main level living space, bathrooms, and laundry. All Chicago homes include our America's Smart Home Technology. Interior Photos are of similar home and model home. Actual home built may vary.

2256 Bodega Road, Oswego

$318,000

3 Beds ⋅ 3 Baths ⋅ 12768232 MLS ⋅ ACTIVE Status

Welcome to this spacious 3-bedroom townhome in Oswego's Townes of Blackberry Knoll, offering multiple levels of living space plus a full English basement. A private entrance opens to a spacious interior featuring upgraded luxury flooring and a bright, functional main level. The kitchen is equipped with LG stainless-steel appliances and flows into the dining area, where sliding doors provide access to the concrete patio. A convenient main-floor laundry room also offers additional pantry and storage space. Upstairs, a versatile loft complements three generously sized bedrooms. The oversized primary suite features a cathedral ceiling, large walk-in closet, and private bath with double-sink vanity, separate soaking tub, and separate shower. The full English basement provides substantial additional space for storage, recreation, a home office, or future possibilities. An attached 2-car garage adds everyday convenience. Located within Oswego Community Unit School District 308 and just minutes from shopping, dining, groceries, medical facilities, and other everyday amenities. With abundant space, numerous recent interior updates, and a flexible floor plan, this home is ready for its next owner.

321 Grape Vine Trail, Oswego

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