Oswego Real Estate

Welcome to Oswego, Illinois – a charming village nestled in the heart of Kendall County. Known for its picturesque landscapes and vibrant community spirit, Oswego offers a perfect blend of suburban tranquility and urban convenience. Just a stone’s throw from the hustle and bustle of Chicago, this delightful town provides residents with easy access to big-city amenities while maintaining its small-town charm.

Oswego boasts a rich history, with roots dating back to the 1830s. Today, it is a thriving community with a population of over 36,000 residents who take pride in their hometown. The village is adorned with beautiful parks, scenic riverfronts, and a variety of recreational facilities that cater to families and outdoor enthusiasts alike. The Fox River, which winds through the area, offers opportunities for fishing, kayaking, and leisurely strolls along its banks.

Education is a cornerstone of the Oswego community, with top-rated schools that prioritize student success and development. The Oswego Community Unit School District is known for its commitment to academic excellence, making it an attractive destination for families looking to settle down.

Culturally rich, Oswego hosts numerous events throughout the year, including the popular Oswego East and West High School Homecoming parades, summer concert series, and the annual PrairieFest, which celebrates the unique heritage of the village.

With its welcoming atmosphere, vibrant local businesses, and a strong sense of community, Oswego is not just a place to live; it’s a place to thrive. Whether you’re looking for a new home or simply exploring, Oswego invites you to discover all that it has to offer!

Newest Listings in Oswego

$587,805

4 Beds ⋅ 3 Baths ⋅ 12761438 MLS ⋅ NEW Status

3 CAR GARAGE - BRICK FRONT OPTION! * READY FOR FALL DELIVERY! SPECIAL INCENTIVES AVAILABLE Homesite #0105 Introducing the Brooklyn model-a thoughtfully designed two-story home that seamlessly blends elegance with everyday functionality. This spacious layout offers four well-appointed bedrooms, two and a half bathrooms, and a private study, making it ideal for both family living and professional needs. A formal dining room near the entrance sets the tone for gatherings, while the adjacent study offers a quiet space for work or creativity. At the heart of the home is an expansive kitchen featuring an oversized center island, premium cabinetry, and sleek countertops. This stylish culinary space flows effortlessly into the breakfast nook and the casual family room, creating a welcoming open-concept layout that's perfect for entertaining and day-to-day comfort. Upstairs, the owner's suite is a peaceful retreat with two generous walk-in closets and a spacious en-suite bathroom. Three additional bedrooms and a second-floor laundry room add both flexibility and convenience, making the Brooklyn an exceptional choice for modern living. Exterior will be OCEANSIDE color siding with Old Lafayette color brick. (pic for reference ONLY) *Photos are not this actual home* Discover Reserve at Hummel Trails, a vibrant master-planned community offering brand-new homes in Oswego, Illinois-where modern living meets everyday convenience and natural beauty. Designed with lifestyle in mind, this inviting neighborhood features a scenic pond and community park, creating the perfect setting for relaxing evenings, outdoor play, and gathering with friends and family. Ideally located just minutes from the bustling Route 59 corridor in Naperville, Illinois, residents enjoy quick access to top-tier shopping, dining, and entertainment. Everyday errands and weekend plans are effortless with nearby destinations like Whole Foods Market, Amazon Fresh, LA Fitness, and Costco. Families benefit from highly regarded Oswego Community Unit School District 308, with convenient access to Southbury Elementary, Traughber Junior High, and Oswego East High School. For outdoor enthusiasts, Wolf's Crossing Community Park is just moments away, offering playgrounds, a splash pad, fitness areas, and open green space for year-round recreation. At Reserve at Hummel Trails, you're not just buying a new home-you're stepping into a connected, amenity-rich community designed to elevate your everyday life."

200 Gentian Court, Oswego

$350,000

3 Beds ⋅ 2 Baths ⋅ 12747765 MLS ⋅ NEW Status

Welcome to this lovely 3 bedroom 2 full bath 2 car attached garage ranch home in Oswego! This home has been meticulously maintained and well cared for. Many updates including newer architectural roof, newer vinyl siding and some aluminum as well, insulated garage door w/EDO, high quality aluminum pull down stairs in garage, updated bathrooms, updated 100 amp electric, newer A/C, furnace, humidifier and water heater, freshly painted interior, new lighting and some new flooring, more! The kitchen is enormous with an island, a huge pantry hosting ample storage, appliance package, etc. Generous room sizes throughout the home as well. All of this close to churches, Oswego Dist 308 schools, shopping, golf, entertainment, lower taxes, no HOA and so much more! Quick close possibly, too! Make this your new home today!

319 Boulder Hill Pass, Oswego

$1,350,000

3 Beds ⋅ 2 Baths ⋅ 12756443 MLS ⋅ NEW Status

1451 Johnson Road, Oswego

$259,900

2 Beds ⋅ 2 Baths ⋅ 12760508 MLS ⋅ NEW Status

Welcome to 233 W Washington St, a charming 2-bedroom, 1.5-bath single-family home in Oswego featuring a versatile loft and several recent updates. With new flooring and fresh interior paint, this home offers a bright, refreshed feel and is ready for its next owner. The additional loft space provides valuable flexibility and can be used as a home office, reading area, playroom, or whatever best fits your lifestyle. The comfortable layout and inviting spaces make this an excellent opportunity for first-time homebuyers looking for a home they can make their own.

233 W Washington Street, Oswego

$1,350,000

3 Beds ⋅ 2 Baths ⋅ 12756395 MLS ⋅ NEW Status

1451 Johnson Road, Oswego

$733,085

4 Beds ⋅ 3 Baths ⋅ 12760316 MLS ⋅ NEW Status

*Below Market Interest Rate Available for Qualified Buyers* Welcome to 103 Arnold Avenue, a stunning new construction home that combines style, space, and modern comfort in the heart of Oswego, IL. This impressive 4-bedroom, 2.5-bathroom residence spans 3,145 square feet, offering abundant space across 2 stories for everything from everyday relaxation to memorable gatherings. Step inside to a welcoming ambiance filled with natural light, and you'll be immediately captivated by the thoughtful design and upscale finishes throughout. At the heart of the home is a chef's dream kitchen, outfitted with GE stainless steel appliances, a butler's pantry, and designed to make cooking a joy, whether it's for daily meals or special occasions. The open layout connects seamlessly to spacious living areas, making entertaining as effortless as it is enjoyable. Finishing the first floor in a separate home office. Each bedroom offers a private retreat, providing ample space to unwind and recharge. The bathrooms bring a touch of luxury to daily routines with their elegant design, creating a tranquil escape right at home. Rounding out this home is a full basement. Located in a vibrant Oswego neighborhood, this home provides easy access to top amenities, parks, schools, and more, balancing peaceful suburban life with urban conveniences. *Photos are of a model home, not subject home* Broker must be present at clients' first visit to any community. Lot 159

103 Arnold Avenue, Oswego

$650,000

12758886 MLS ⋅ NEW Status

0000 Johnson Road, Oswego

$695,000

4 Beds ⋅ 4 Baths ⋅ 12652938 MLS ⋅ NEW Status

Located within the sought-after custom home community of Deerpath Trails, this exceptional home offers an impressive combination of space, functionality, and fine finishes. A four-car garage provides ample parking and storage, while the deep-pour basement offers an additional full bedroom and an abundance of unfinished space ready to be customized to suit your needs. The open-concept main level features an array of beautiful details, including wainscoting in the dining room and crown molding throughout the split-entry living and dining areas. Tucked away at the back of the first floor, the spacious den/office provides a quiet and private workspace. The expansive kitchen is designed for both everyday living and entertaining, featuring a large eating area, oversized island, and abundant cabinetry and storage. Glass sliding doors lead directly to the freshly stained deck and granite patio, creating an easy transition between indoor and outdoor living. The kitchen also connects seamlessly to the dining room through a fully appointed butler's pantry. A generous laundry and mudroom offers exceptional functionality with extensive storage and space for keeping everyday essentials organized. Upstairs, you'll find three full bathrooms along with a versatile bonus room-perfect for movie nights, cheering on your favorite sports team, a playroom, or settling in for a good binge-watch. The spacious primary suite features a comfortable sitting area, while the luxurious primary bath offers dual sinks and an ample walk-in closet. With its generous living spaces, thoughtful layout, extensive storage, and room to customize, this Deerpath Trails home offers an exceptional opportunity to make a truly special property your own. New roof in 2019 and so much more. For a full list, see Additional Information.

402 Deerfield Drive, Oswego

$440,000

4 Beds ⋅ 3 Baths ⋅ 12758347 MLS ⋅ NEW Status

Discover the potential in this spacious 4-bedroom, 2.5-bath home in the heart of Oswego, offering generous living spaces, a functional floor plan, and several major recent updates. A welcoming two-story foyer sets the tone as you enter, while large windows throughout fill the home with an abundance of natural light. The thoughtfully designed layout provides plenty of space for everyday living, entertaining, and working from home. Fresh interior paint and brand-new carpeting create a clean, neutral foundation, while still offering the next owner the opportunity to add their own style and personal touches. The partially finished basement adds valuable additional living space and features a dry bar-perfect for a recreation room, home office, fitness area, playroom, or game-day gatherings. Step outside to a generously sized backyard offering endless possibilities for outdoor entertaining, gardening, play, or simply relaxing and enjoying the outdoors. Major recent improvements add even more value, including a brand-new roof (August 2026), new water heater (July 2026), new air conditioner, and whole-home interior paint (Spring 2026), plus new carpet (summer 2026). Conveniently located near parks, walking trails, shopping, dining, and Oswego-area schools, this home offers the ideal combination of space, location, recent improvements, and opportunity. Whether you're looking for room to grow or a home you can personalize over time, this property is ready for its next chapter.

418 Terrace Lane, Oswego

$379,900

3 Beds ⋅ 3 Baths ⋅ 12756226 MLS ⋅ NEW Status

Custom-Built Ranch Near Downtown Oswego Welcome home to this unique custom-built ranch featuring over 1,800 square feet on the main level plus a full basement! Designed with comfort, entertaining, and privacy in mind, this spacious home offers an inviting open floor plan and plenty of room to grow. The large family room features vaulted ceilings and a cozy fireplace, creating the perfect space to relax on chilly evenings. The generously sized dining room provides plenty of space for hosting large family gatherings and holiday meals. Just off the dining room, the spacious kitchen offers convenient access to the outdoors through sliding doors that lead to a large concrete patio-ideal for summer entertaining. The primary suite is generously sized and includes a walk-in closet and private full bath. Two additional bedrooms are located at the opposite end of the home, providing added privacy for family members or guests. The spacious full basement features an extra-deep pour for higher ceilings and is partially finished with a versatile bonus room that could be used as a home office, hobby room, exercise space, or whatever fits your lifestyle. A full basement bathroom adds even more functionality. Step outside to the large 24' x 30' detached garage and fully fenced yard, perfect for pets, recreation, and outdoor enjoyment. Location is hard to beat! Enjoy being close to Downtown Oswego, with its shopping, restaurants, schools, bike paths, river walk, community events, and festivals.

464 S Madison Street, Oswego

$295,000

12756548 MLS ⋅ PRICE CHANGE Status

52 N Adams Street, Oswego

$525,000

4 Beds ⋅ 3 Baths ⋅ 12755392 MLS ⋅ NEW Status

12 N Adams Street, Oswego

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