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

$319,900

3 Beds ⋅ 3 Baths ⋅ 12799577 MLS ⋅ NEW Status ⋅ Prescott Mill BLDG.

Enjoy effortless living in this stunning, zero-exterior-maintenance townhome located in the prestigious Prescott Mill planned community. Ideally situated within walking distance of schools, parks, and beautiful water views, this thoughtfully designed two-story home offers style, comfort, and exceptional amenities. The impressive Great Room features soaring ceilings, creating an open and inviting atmosphere. The chef's kitchen showcases granite countertops, 42-inch Shaker cabinetry, and custom stainless steel appliances. A charming breakfast nook provides convenient patio access to a beautifully landscaped outdoor retreat, complete with a sitting area and space for grilling. The main level features newer wood-look tile flooring, while the spacious primary bedroom suite offers a private glamour bath with double sinks, granite countertops, and a walk-in shower. An additional second-floor loft provides flexible space for a home office, reading area, or relaxation. Additional improvements include newer HVAC, along with an impressive garage featuring epoxy flooring, heating, and air conditioning, giving it a polished, finished-room appearance. The roof and siding were replaced in 2021. The HOA covers exterior maintenance, including the roof and siding, as well as resealing every other year. Enjoy beautiful lake views and the convenience of maintenance-free living in this desirable community. Owner relocating. Immediate occupancy available upon closing. Easy to show. This exceptional townhome won't last!

333 Devoe Drive, Oswego

$399,900

3 Beds ⋅ 2 Baths ⋅ 12800286 MLS ⋅ NEW Status

Wow, this move-in ready 3-bedroom, 2-full-bath ranch in Oswego is an absolute standout! Nestled on a beautifully landscaped lot surrounded by mature trees for exceptional curb appeal, this home boasts an unbeatable location just minutes from downtown Oswego, the Fox River, local parks, and top-rated schools. Step inside to find a fresh, modern interior complete with crisp paint, hardwood flooring, and soft new carpet throughout. The spacious layout features both an expansive living room and a cozy family room, along with a bright kitchen equipped with abundant cabinetry, sleek quartz countertops, and stainless steel appliances. Three generously sized bedrooms and two full baths offer plenty of room to unwind, while the huge unfinished basement provides endless potential for extra living space, a workshop, or custom finishes. Complete with a 2-car garage plus an additional storage garage for all your tools and toys, this stunning home truly has it all-book your private showing today before it's gone!

53 Cebold Drive, Oswego

$540,000

4 Beds ⋅ 4 Baths ⋅ 12792204 MLS ⋅ NEW Status

The one you've been waiting for in Ashcroft. This 4-bedroom home gives you 3,369 square feet of living space, a full basement, and a layout that actually works for real life. From the moment you walk in, the formal entry welcomes you- with a formal living room and formal dining room right there for entertaining or quiet evenings. The kitchen opens to a dining combo and flows straight into the family room, so the heart of the home stays connected. And with three fireplaces, there's a cozy spot no matter where you land. The primary bedroom is oversized with a tray ceiling- plenty of room for a king set plus a sitting area, and it lives like the retreat it should be. Bathrooms on every level (2 full, 2 half) mean no more running up and down the stairs. There's a mud room to keep the clutter contained, a butler's pantry for extra prep and storage, and the 4-car heated garage is the kind of thing buyers rarely find- park the toys, set up a workshop, or just keep your babies warm all winter. Out back there's a beautiful updated brick patio & new firepit perfect for evenings outside, and the yard is fully fenced with a 6-foot privacy fence. The home has been well maintained, the roof is 6 years old, and HOA dues are low. All of it in Oswego 308 schools. Move-in ready. Come see it.

243 Ashcroft Lane, Oswego

$220,000

12801223 MLS ⋅ NEW Status

Incredible location in the heart of downtown Oswego's business and shopping district. Enjoy the free marketing of 1000's of cars a day at your doorstep! Home has been gutted by the current owner and is ready for updated electric, plumbing, and/or whatever creativity you have in mind! Building has almost 1700 SF of usable space with 2 stories. Easily remodeled for a retail space, office, slot machine cafe, or whatever your entrepreneurial desires require! The true value is the location. Come view this opportunity and let your imagination run wild!

61 S Madison Street, Oswego

$305,900

2 Beds ⋅ 2 Baths ⋅ 12801130 MLS ⋅ NEW Status

Welcome to Winding Waters, Oswego. A prime location for an unbeatable price. This turn-key ready condo/townhome features modern touches, low maintenance, and easy access to every store and restaurant in the areas. You're going to love the layout of this townhome. On the first floor; Step right into the family room soaked with natural light and Cathedral vaulted ceilings. the open floor concept leads you to the kitchen featuring a beautiful and practical island, and all stainless steel appliances. Conveniently located right off the hallway that leads to the garage is a half bathroom and a mudroom at the entry connecting the garage and first floor. Second floor features the primary suite that connects to the full bathroom and a walk-in closet. Right next to it is the laundry closet with newer Washer and Dryer Machines and a second bedroom. New carpets have been installed. Furnace got an upgraded starter motor and serviced in 2025. AC 2023, Hot Water tank 2016, All new light fixtures, New refrigerator 2024, new roof 2019. Schedule your private tour today and welcome home!

400 Cascade Lane, Oswego

$315,000

2 Beds ⋅ 3 Baths ⋅ 12792228 MLS ⋅ NEW Status ⋅ Prescott Mill BLDG.

Two bedrooms, a spacious loft, 2.5 baths, and an attached heated 2-car garage! This end-unit townhome in Oswego's Prescott Mill offers about 1,500 sq ft, red oak hardwood floors, 9-foot ceilings, and low-maintenance living. Quick close possible! Step inside to abundant natural light, crisp white trim, and a living room that flows into the kitchen, featuring custom Brakur maple cabinetry, stainless steel appliances, a walk-in pantry, recessed lighting, and an eating area. Outside, the concrete patio and adjoining grassy space are ideal for grilling and entertaining, without a sprawling yard to maintain. Upstairs, the spacious loft works as a home office, second living area, workout space, or potential third bedroom. The primary suite features a large walk-in closet and private bath with a double vanity and glass-enclosed shower. A second bedroom, full hall bath, and upstairs laundry complete the level. The association covers lawn care, snow removal, and exterior maintenance, so the heated garage and no shoveling make Illinois winters easy. Cats and dogs are welcome! Prescott Mill offers sidewalks, green space, ponds, walking paths, and a playground, with shopping and dining nearby in Oswego. Served by Southbury Elementary, Murphy Junior High, and Oswego East High School. Schedule your showing today, and you could be settled in before the holidays!

501 Valentine Way, Oswego

$425,000

3 Beds ⋅ 3 Baths ⋅ 12799793 MLS ⋅ NEW Status

Experience the best of Oswego living at 4632 Mclaren Dr! Located in the prestigious Hunt Club community on nearly 1/3 acre, this 2,300 sq. ft. home offers 3 bedrooms, 2.5 baths, and a versatile loft. The main level flows from formal living and dining areas with hardwood floors to a spacious kitchen with 42" cabinets and island seating. Step out to a massive backyard with a patio and fire pit to enjoy those scenic sunsets. The spacious primary suite serves as a private getaway with a soaking tub and separate shower. Additional highlights include a loft perfect for work-from-home needs, spacious additional bedrooms with walk-in closets, an unfinished basement for future equity, and a 2.5-car garage, and a Generac whole-home generator for peace of mind in any storm. The Hunt Club East lifestyle is second to none. Residents enjoy exclusive access to the community clubhouse, a sparkling pool, and a fully equipped fitness center. For those who love the outdoors, miles of scenic walking paths wind through the neighborhood, perfect for morning jogs or evening strolls. Best of all, the highly rated District 308 schools are within easy walking distance, with a prime location minutes from downtown Oswego, retail, and the Fox River. Schedule your showing today!

4632 Mclaren Drive, Oswego

$599,900

5 Beds ⋅ 4 Baths ⋅ 12797206 MLS ⋅ NEW Status

YES... You CAN have it all! Welcome to 705 Wilmore Drive, located in the highly sought-after Churchill Club community of Oswego! This beautifully updated Spectacular Bid model offers 5-6 bedrooms, 3.5 bathrooms, a 3-car deep garage, and an impressive 4,593 square feet of finished living space, including the fully finished drop dead gorgeous basement. With thoughtful upgrades, spacious living areas, and exceptional neighborhood amenities, this home offers the perfect combination of comfort, style, and convenience! The main level welcomes you with hardwood flooring, 9-foot ceilings, formal living and dining rooms, and a beautifully remodeled gourmet kitchen featuring 50-inch upper maple cabinetry, a 9-foot pantry cabinet, soft-close cabinetry, granite countertops, updated lighting, and 2025 stainless steel appliances. The oversized waterfall granite island provides additional prep space, storage, and seating, while the adjoining breakfast area and butler's pantry with wine refrigerator make entertaining effortless. The dramatic two-story great room features a wood-burning fireplace with gas starter, abundant natural light, and access to the backyard. A versatile main-level bedroom or private office with double-door entry adds flexibility. Upstairs, the spacious primary suite features vaulted ceilings, an impressive 12x12 walk-in closet, and a private bath with dual granite vanities, soaking tub, separate shower, and ceramic tile. Three additional bedrooms, including two with access to the charming front balcony, a full hall bath, convenient second-floor laundry room, and an open loft overlooking the great room complete the upper level. The fully finished basement expands your entertaining and living possibilities with luxury vinyl plank flooring, a spacious recreation room, wet bar with two wine refrigerators, cabinetry, shelving, and bar seating. A sixth bedroom with an egress window, full bathroom, flexible bonus room, and additional storage provide plenty of space for guests, recreation, hobbies, or multigenerational living. Additional highlights include a finished 3-car tandem garage with built-in storage, two 50-gallon water heaters, a sump pump with battery backup, and beautiful exterior improvements completed in 2025, including a new front walkway, stamped concrete patio with stained and sealed finish, and refreshed front facade. LIVING IN CHURCHILL CLUB IS LIKE HAVING A RESORT RIGHT IN YOUR OWN NEIGHBORHOOD! Residents enjoy an impressive 10,000-square-foot clubhouse with fitness center and gathering spaces, a junior Olympic-size swimming pool with waterslides, children's tot pool, splash pad, pickleball, tennis, volleyball and basketball courts, and miles of scenic walking and biking trails winding along ponds and prairie preserve areas. Three schools are conveniently located right within the community: Churchill Elementary, Plank Junior High, and Brokaw Early Learning Center. Oswego East High School is approximately one mile away! LOCATION, LOCATION, LOCATION! Churchill Club offers outstanding access to shopping, dining, parks, and everyday conveniences along the Route 34 and Douglas Road corridors. Ideally situated approximately 5 miles west of Naperville and 48 miles west of downtown Chicago, with convenient access to I-88, I-55, and Metra commuter rail service in both Aurora and Naperville, this location offers an exceptional balance of suburban living and regional connectivity. Experience the space, upgrades, lifestyle, and convenience that make Churchill Club one of Oswego's most desirable communities. Welcome home to 705 Wilmore Drive!

705 Wilmore Drive, Oswego

$615,990

5 Beds ⋅ 3 Baths ⋅ 12800281 MLS ⋅ NEW Status

5 BEDROOM IN LAW SUITE * BRICK FRONT ELEVATION! SPECIAL FINANCING AVAILABLE! Homesite #0099 READY FOR DELIVERY! Discover the Raleigh, a home expertly planned to combine style and everyday comfort. This spacious layout offers five bedrooms, three bathrooms, and a dedicated study to suit your lifestyle. The main level features a seamless flow between the family room, kitchen, and breakfast room, creating an open and inviting space perfect for both relaxing and entertaining. The chef-inspired kitchen boasts stainless steel appliances, sleek 42" cabinetry, elegant quartz countertops, and a large island that serves as both a functional workspace and gathering spot. The owner's suite, located upstairs, is a true retreat featuring a walk-in closet and a spa-like en-suite bathroom with dual sinks and a deluxe shower. Three additional bedrooms share a full bathroom, and the main-level laundry room adds ease to your daily routine. An Open to Below lookout from the second level creates a dramatic and airy connection to the other rooms below, enhancing the home's spacious feel. A standard three-car garage provides ample parking and storage. Exterior will be ASPEN WHITE color siding with Graystone color brick. (pic for reference ONLY) *Photos are not this actual home* Welcome to Hudson Pointe II, a beautifully designed master-planned community offering brand-new homes in the heart of Oswego, Illinois. Perfectly blending comfort, convenience, and natural beauty, this neighborhood is ideal for families and individuals seeking a balanced lifestyle. Right within the community, residents can enjoy a well-maintained park for leisurely play and gatherings, as well as a serene pond that enhances the peaceful atmosphere of Hudson Pointe II. Just 10 minutes from the Naperville Route 59 corridor, Hudson Pointe II places premier shopping, dining, and entertainment within easy reach. Access top destinations like Whole Foods, Amazon Fresh Market, LA Fitness, and Costco, along with a variety of local restaurants and entertainment spots. Families will appreciate the top-rated Oswego School District 308, with students attending Southbury Elementary, Murphy Junior High, and Oswego East High School-all conveniently located within a 10-minute drive. Outdoor enthusiasts will love the close proximity to Wolf's Crossing Community Park, offering an array of recreational features including playgrounds, an outdoor fitness area, a splash pad, and more-perfect for year-round family fun. At Hudson Pointe II, you're not just buying a home-you're joining a thoughtfully planned community where modern living meets natural charm and everyday convenience.

516 Fridley Avenue, Oswego

$315,000

3 Beds ⋅ 3 Baths ⋅ 12796270 MLS ⋅ NEW Status ⋅ Winding Waters BLDG.

Welcome home to this spacious, move-in-ready 3-bedroom, 2.5-bath townhome, offering a perfect blend of comfort, style, and convenience. The impressive 9-foot vaulted ceilings create an open, airy atmosphere. The flooring was updated in 2023, and the furnace and air conditioning system were replaced in 2019 and have been professionally serviced annually. Ideally located near top-rated schools, shopping, restaurants, grocery stores, and major highways, this home offers the perfect combination of comfortable living and everyday convenience. Don't miss the opportunity to make this beautiful townhome your own!

239 Grays Drive, Oswego

$529,990

4 Beds ⋅ 3 Baths ⋅ 12799568 MLS ⋅ NEW Status

Discover yourself at 2318 Hirsch Rd. Oswego, Illinois, a beautiful new home situated on a FULLY SODDED AND LANDSCAPED YARD, located in our amenity filled Sonoma Trails community. This home will be ready for a winter move-in! The Henley floorplan offers 2,600 square feet of living space with 4 bedrooms Plus LOFT, 2.5 baths, flex room, 9ft ceilings on first floor and a full basement. Entertaining will be easy in this open-concept kitchen family room and dining layout with a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close doors and drawers. Additionally, the kitchen features a walk-in pantry, modern stainless-steel appliances, sparkling quartz countertops, and easy-to-maintain luxury vinyl plank flooring throughout the first floor! Finishing off the main floor you will have an XL Mud room and storage closet. Heading up the beautiful wrought iron staircase you will find More flexible space is awaiting in the 2nd floor loft offering unlimited potential to suit your needs. Enjoy your private getaway with your large primary bedroom and en suite bathroom with a raised height dual sink, quartz top vanity, walk-in-shower with clear glass shower door. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath and a linen closet complete the second floor. All Chicago homes include our America's Smart Home Technology. Exterior/interior photos of similar home, actual home as built may vary.

2318 Hirsch Road, Oswego

$399,990

3 Beds ⋅ 3 Baths ⋅ 12799551 MLS ⋅ NEW Status

Welcome to 2475 Barbera Dr. in the amenity-rich Sonoma Trails community of Oswego, IL. Available for winter delivery, this beautifully designed Haven floorplan offers over 1,500 square feet of thoughtfully planned living space with 3 bedrooms, 2.5 baths, and a 2-car garage. This home will feature a fully sodded yard and included landscaping package for added curb appeal. Inside, the open-concept great room and kitchen create an inviting space for everyday living and effortless entertaining. The kitchen showcases 42" designer cabinetry, quartz countertops, and a convenient pantry. Upstairs, you will find a private primary suite situated on its own side of the second floor, complete with a deluxe bath featuring a raised dual quartz vanity and spacious walk-in closet. Two additional bedrooms, a full hall bath, linen closet, and convenient second-floor walk-in laundry room complete the upper level. All Chicago homes include America's Smart Home Technology. Exterior/interior photos are of a similar home; actual home as built may vary.

2475 Barbera Drive, Oswego

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Oswego Real Estate

Newest Listings in Oswego

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