Browse All Oswego IL Historical Properties for Sale

3 Beds ⋅ 2 Baths ⋅ 12707187 MLS ⋅ CONTINGENT Status

History and modern comfort come together beautifully at 453 Main Street in Oswego. Built in 1902 by four master builders, this one-of-a-kind home is rich in character and timeless craftsmanship while offering today's most sought-after updates. Situated on nearly an acre, this property provides a peaceful retreat with mature trees and privacy, all within walking distance to charming downtown Oswego, where you'll enjoy local shops, restaurants, parks, and community events. From the moment you arrive, you'll be welcomed by the inviting front porch, complete with a natural gas sconce, making it the perfect place to enjoy your morning coffee or unwind in the evening. Inside, you'll immediately appreciate the stunning original oak trim, beautiful woodwork, and the restored living room fireplace that create warmth and historic elegance throughout the home. The fully updated gourmet kitchen is designed for both everyday living and entertaining, featuring KitchenAid stainless steel appliances, a farmhouse sink, pot filler faucet, abundant cabinetry, and generous counter space that will delight any home chef. The spacious primary suite serves as a private retreat, complete with its own balcony overlooking the expansive backyard-an ideal spot to relax and take in the peaceful surroundings. The finished basement offers additional living space with a welcoming family room featuring a wet bar and wine refrigerator, perfect for entertaining family and friends. Step outside and discover your own private oasis. Follow the path beyond the insulated two-car garage to a secluded wooded area with a fire pit, creating the perfect setting for evening gatherings, roasting marshmallows, or simply enjoying the stars. The garage has been thoughtfully upgraded with raised rafters for additional storage, electrical service, newer windows, two service doors, and new garage doors installed in 2022. This meticulously maintained home has seen numerous recent improvements, including a new roof (2018), fully remodeled upstairs hall bathroom (2019), restored living room fireplace (2020), new water softener (2021), new hot water heater (2021), new bedroom carpeting (2021), new basement flooring (2022), new fence (2022), and new garage doors (2022). This is a rare opportunity to own a truly historic home that perfectly blends timeless craftsmanship, modern amenities, and an exceptional location. Homes with this much character, land, and convenience rarely become available. Schedule your private showing today and experience everything this remarkable property has to offer.

453 Main Street, Oswego

$349,900

2 Beds ⋅ 1 Baths ⋅ 12697357 MLS ⋅ CONTINGENT Status

If you've been waiting for an affordable home with space, updates, and an unbeatable location, your search ends here! This charming Oswego ranch sits on an impressive .41-acre lot and offers the perfect combination of comfortable living, practical updates, and future potential. Inside, you'll find 2 spacious bedrooms, 1 full bath, and an inviting layout designed for easy everyday living. The attached 2-car garage provides convenience year-round, while the partially finished full basement adds valuable flexible space that can easily adapt to your lifestyle. Whether you envision updating the current family room, adding a media space, home office, workshop, or guest area, the basement gives you room to make it your own. Major mechanical improvements add tremendous value and peace of mind, including an HVAC system installed in 2018, new water heater in 2023, and a new sump pump in 2026. These significant updates allow you to move in with confidence knowing many of the home's essential systems have already been addressed. Outside you will enjoy the enclosed porch, the oversized lot offers endless opportunities to create your own backyard oasis. Host summer barbecues, add gardens, build a play area, or simply enjoy the extra elbow room that's becoming increasingly difficult to find. With no HOA restrictions, you'll enjoy the freedom to personalize your property to fit your lifestyle. The home also features a private well and septic system, providing additional independence and long-term value. Ideally located near I-88, shopping, restaurants, parks, this home delivers convenience without sacrificing the quiet charm of suburban living. Whether you're buying your first home, downsizing, or looking for a smart investment, this well-maintained ranch is ready for its next chapter-and yours.

47 Pasadena Drive, Oswego

$449,999

3 Beds ⋅ 2 Baths ⋅ 12706835 MLS ⋅ CONTINGENT Status

WELCOME HOME TO YOUR PRIVATE RANCH OASIS! The curb appeal as you approach your new home is unmatched with gorgeous landscaping, over an acre of land and a peaceful backyard retreat! The front porch has beautiful brick columns and space to sit with your morning coffee. As you enter, you are invited by gleaming hardwood floors into the living room with a gas fireplace. The eat in kitchen overlooks the back patio and expansive yard. The thoughtful design provides a built-in table with storage cabinets! Stainless steel appliances, granite counters and a tile backsplash add to the design. A pantry closet provides plenty of food/appliance storage. The primary suite includes two closets, a walk-in shower and separate water closet. Two additional bedrooms and a full bath round out the living space. The wrought iron spindles and brick accent wall invite you to the basement living area which includes an add on fireplace and built in shelving. A large storage area that houses all of the mechanicals provides space for all your totes! The laundry/mud room is right off the garage and has built in cabinets with a sink. The oversized 3+ car garage has high ceilings and great possibilities for a work bench area or an additional hang out area to watch sporting events! Out back enjoy the patio that includes a pergola and auto awning. Sit, relax and enjoy the view in your private oasis! Feel like you are living in the country but hop in your car and get to the store or interstate in minutes! DON'T MISS YOUR OPPORTUNITY TO OWN THIS BEAUTY!! A whole home renovation was completed in 2016, completely changing the footprint and layout of the home. Roof, siding, windows, AC/Furnace were all replaced in 2016. Sump pump and water heater new in 2025, fridge in 2024. The home is on well/septic and also has a whole house fan. A storage shed is also included. Home is being sold AS IS.

32 E Rickard Drive, Oswego

$279,000

3 Beds ⋅ 2 Baths ⋅ 12701956 MLS ⋅ ACTIVE Status

Step into the timeless charm of this vintage home nestled in the heart of historic Old Town Oswego! Just a short walk to downtown shops, restaurants, parks, and local favorites, this home offers character you simply can't recreate. Original hardwood floors lie beneath the carpet in the living room, dining room, and den, waiting to be brought back to life. The spacious kitchen has been updated with oak cabinetry and flooring while maintaining the home's classic appeal. Featuring 3 bedrooms, 2 full bathrooms, a basement with ample storage, and a detached one-car garage, there's plenty of room to make it your own. Enjoy relaxing on the welcoming screened front porch or entertaining on the rear deck and patio. With solid bones, vintage character, and the opportunity to add your own cosmetic touches over time, this is the perfect home for buyers who appreciate classic craftsmanship and want to build equity while preserving its historic charm.

39 Park Street, Oswego

$1,000,000

4 Beds ⋅ 3 Baths ⋅ 12699328 MLS ⋅ ACTIVE Status

Timeless farmhouse charm meets today's modern luxury on 2.27 picturesque acres! Completely transformed through an extensive whole-house renovation, this one-of-a-kind property offers the perfect blend of historic character, thoughtful craftsmanship, and incredible versatility. The heart of the home is a stunning custom kitchen (2022) featuring a massive quartz island, farmhouse sink, custom staggered cabinetry, premium Wolf range, double ovens, stainless steel appliances, and abundant storage designed for everyday living and effortless entertaining. Rich hardwood flooring, fresh paint, updated trim, custom two-panel doors, and soaring 10-foot ceilings throughout much of the main level create a warm, inviting atmosphere. Flexible living spaces provide endless possibilities, including formal living and dining rooms, a private home office, a cozy family room with fireplace, and a light-filled sunroom overlooking the property. The main level also includes beautifully remodeled laundry and powder rooms. Upstairs, the private primary suite offers a spacious walk-in closet and remodeled en-suite bath, while three additional bedrooms share a beautifully renovated hall bath complete with dual vanities, heated floors, illuminated mirrors, an oversized 48-inch shower with built-in seat, and a luxurious soaking tub. Major improvements provide peace of mind, including updated electrical and plumbing, new well (2017), tankless water heater with water filtration system, roof on both the home and barn (2018), waterproofed basement with French drain system, and much more. Outdoor living is equally impressive with a custom covered front porch, expansive brick paver patio, updated deck, mature trees, and beautifully maintained grounds. The approximately 1,400-square-foot two-story barn is an incredible bonus, offering exposed beams, electricity, gas line, water hookup, high-efficiency furnace, lift, and multiple finished and unfinished spaces ideal for a workshop, studio, hobby farm, collector cars, home business, or future expansion. An additional 20x30 garden shed with electricity provides even more flexibility. Located just minutes from the Route 34 shopping corridor, Fox Bend Golf Course, and the restaurants and charm of Downtown Oswego, this exceptional property offers the rare opportunity to enjoy peaceful country living without sacrificing everyday convenience. If you've been dreaming of a beautifully restored farmhouse with room to spread out, entertain, pursue your hobbies, or simply enjoy life on acreage, this is one you won't want to miss.

3614 Wolf Road, Oswego

$669,900

4 Beds ⋅ 3 Baths ⋅ 12699457 MLS ⋅ CONTINGENT Status

Welcome home to this beautifully updated ranch situated on an oversized corner lot, offering the ease of main-floor living with custom finishes throughout. Just a short walk to the Fox River, this move-in-ready home combines comfort, quality, and an exceptional location. Inside, you'll find 4 bedrooms, 2.5 bathrooms, beautiful hardwood floors, solid 6-panel oak doors, and rich oak trim throughout, showcasing timeless craftsmanship. Major updates provide peace of mind, including a new roof (2025), furnace and A/C replaced within the last five years, and a whole-house water filtration system with a new pressure tank for the private well installed just two years ago. The newly finished basement expands your living space, making it perfect for entertaining, a recreation room, or a home gym. Utilize all of your basement space with the massive concrete crawlspace! Step outside to enjoy the spacious deck overlooking the backyard, complete with a brick fire pit that's ideal for relaxing evenings with family and friends. Need extra storage or workspace? In addition to the attached two-car heated garage, you'll appreciate the detached two-car garage in the backyard-perfect for hobbies, vehicles, or additional storage. From top to bottom, this meticulously maintained home is truly move-in ready and waiting for its next owners!

28 S Cherry Drive, Oswego

$285,000

3 Beds ⋅ 2 Baths ⋅ 12677963 MLS ⋅ CONTINGENT Status

Welcome to 8 Dolphin Court in unincorporated Oswego! Located on a quiet cul-de-sac and connected to city water and sewer, this well-maintained ranch may be just what you are looking for. Approximately 1,092 square feet, this home features 3 bedrooms, 1 full bath and 1 half bath off the primary bedroom, a spacious living room, and an updated kitchen with stainless steel appliances and a separate eating area. Durable flooring runs throughout much of the home, creating a cohesive and low-maintenance living space. The oversized laundry and mudroom provides additional storage and everyday functionality, while the attached 2-car garage offers plenty of room for vehicles, tools, and hobbies. Outside, enjoy the fully fenced backyard, complete with a storage shed and plenty of room for pets, play, gardening, or entertaining. Situated on a generous .257-acre lot, you'll appreciate having space to spread out while still being close to shopping, dining, parks, and schools. Located within Oswego School District 308, this move-in ready home is an excellent opportunity for first-time buyers, downsizers, or anyone seeking affordable single-level living with lower unincorporated taxes.

8 Dolphin Court, Oswego

$639,000

2 Beds ⋅ 3 Baths ⋅ 12688017 MLS ⋅ ACTIVE Status

Beautiful park-like 3.75 acre (+/- to be determined by boundary survey) ranch style home with oversized 2 car attached garage, and additional 1 car detached garage currently used as shop with its own loft and additional room for equipment. Oversized Master bedroom with oversized walk in closet and full bathroom. All appliances included in eat-in kitchen. Formal dining room and large mudroom on 1st floor. Mudroom has not only garage entry, but additional exterior door leading to brick courtyard at rear of house. Full finished basement with office, family room & kitchenette, laundry room including washer & dryer and 3rd bedroom with bathroom. Home has 2 fireplaces. Wood burning fireplace in original living room, and gas fireplace in large 1st floor Great Room. Two decks accessible through Great Room lead you to large portion of area, in fenced back yard. Home has ample storage found throughout the house. All Window treatments stay. Listing agent must accompany all showings and 24 hour notice requested. Pre-Approval needed, prior to scheduling a showing. 24 hours advance notice requested for showings.No sign on property.***NO LOCK BOX***Listing agent must be present. ***CALL DIRECTLY FOR APPOINTMENT***

6274 Us Highway 34 Highway, Oswego

$375,000

3 Beds ⋅ 2 Baths ⋅ 12647475 MLS ⋅ CONTINGENT Status

RARE FULL BRICK RANCH IN DOWNTOWN OSWEGO WITH FINISHED BASEMENT, DETACHED FLEX SPACE WITH 240-AMP ELECTRIC, COVERED OUTDOOR LIVING AREA, NO HOA, AND NUMEROUS RECENT IMPROVEMENTS! Welcome to 425 Douglas Street, a beautifully maintained and thoughtfully updated home located on a mature tree-lined street in one of Oswego's most desirable established neighborhoods. Combining solid full-brick and cinder block construction, functional living spaces, extensive updates, and an exceptional location near Downtown Oswego, this home presents a rare opportunity that is increasingly difficult to find. Exterior improvements include updated concrete driveway, sidewalks, patio areas, and walkways completed in 2022, plus a newer rear fence section for added privacy. Inside, refinished hardwood flooring extends throughout the living room, dining room, and all bedrooms, while built-in hallway storage preserves the home's original charm and functionality. Large windows fill the home with natural light, and the living and dining areas provide comfortable spaces for everyday living and entertaining. The galley-style kitchen features original cabinetry enhanced with updated hardware, a newer sink, and durable countertops. The remodeled main-level bathroom offers modern finishes and an easy-access shower. Three main-level bedrooms provide flexibility for guests, home office space, hobbies, or family living. The finished basement significantly expands the home's living area with a spacious recreation room featuring a gas fireplace, built-in bar area, additional finished space for hobbies, fitness, storage, or workspace needs, plus a convenient bathroom adjacent to the laundry area. Major updates include a new water heater (2026), roof and gutters (2024), central air conditioning (2023), and furnace evaporator coils (2024). Outdoor living is equally impressive with a covered concrete patio perfect for relaxing, grilling, dining, and entertaining. One of the property's most unique features is the approximately 20' x 10' detached flex space equipped with 240-amp electrical service and two fans, offering exceptional versatility for hobbies, projects, creative pursuits, exercise equipment, storage, or workspace needs. Additional highlights include an attached garage with refinished concrete floor, epoxy-coated basement floors, mature landscaping, extensive concrete improvements that assist with drainage and accessibility, gas furnace, gas fireplace, and the freedom of living without HOA restrictions. Enjoy convenient access to Downtown Oswego's restaurants, coffee shops, boutiques, seasonal festivals, parks, local events, and community gathering spaces. Outdoor enthusiasts will appreciate nearby access to the Fox River, Fox River Trail, and regional bike path system. The home is served by the highly regarded Oswego School District 308. Residents enjoy convenient access to shopping, dining, grocery stores, healthcare services, fitness centers, and entertainment throughout Oswego, Yorkville, and Aurora. Commuters will appreciate easy access to Route 34, Route 30, Orchard Road, Route 71, Interstate 88, and the Aurora Transportation Center Metra Station. Properties offering full brick and cinder block construction, refinished hardwood floors, finished basement with fireplace and bar, major mechanical updates, covered outdoor living space, dedicated detached flex space, no HOA, and a walkable Downtown Oswego location are increasingly rare. Whether you're searching for a full brick ranch, a home near the Fox River and trails, a property in District 308, or a home offering flexible bonus space and exceptional value, 425 Douglas Street delivers a rare combination of durability, character, functionality, updates, and location.

425 Douglas Street, Oswego

$1,100,000

7 Beds ⋅ 3 Baths ⋅ 12682754 MLS ⋅ ACTIVE Status

Welcome to Oakberry Farm, a rare 8.5-acre private country estate tucked among mature hardwoods and rolling woodlands just minutes from Oswego, Plainfield, and Naperville. Rich in history, character, and natural beauty, this remarkable property offers two homes, multiple outbuildings, private walking trails, and a setting that feels worlds away from the everyday.~~~The centerpiece of the estate is a beautifully renovated Victorian farmhouse featuring 5 bedrooms, 2 bathrooms, and 3,038 square feet. Timeless architectural details, soaring ceilings, original character, and extensive updates combine to create a home that is both elegant and inviting.~~~A separate Cottage offers an additional 1,662 square feet with 2 bedrooms and 1 bathroom, creating exceptional flexibility for multi-generational living, guests, a private home office, caretaker quarters, or potential rental opportunities.~~~The property also includes a heated and insulated Art Studio with concrete floors and electricity, detached 3-car garage, greenhouse, garden shed, and two historic barn structures that contribute to the property's unique charm and story. A picturesque two-story timber-frame barn stands as a reminder of the property's agricultural roots and creates a stunning focal point within the landscape, while a charming former stable building, affectionately known as "The Museum," further enhances the estate's historic appeal.~~~Towering oak, walnut, maple, and other mature hardwood trees surround the property, while private trails wind through the woods creating an extraordinary backdrop for daily life. Agricultural zoning offers flexibility for future use while preserving the property's rural character.~~~Properties of this caliber and versatility rarely become available. Whether you're seeking a private retreat, multi-generational estate, or simply a one-of-a-kind property with unmatched character and setting, Oakberry Farm presents an exceptional opportunity.

7479 Grove Road, Oswego

$399,000

2 Beds ⋅ 1 Baths ⋅ 12669255 MLS ⋅ ACTIVE Status

Discover a rare Fox Riverfront home for sale in Oswego, Illinois! Situated on a 1.05-acre lot directly across from the Fox River and Veterans Serenity Park, this property offers stunning year-round water views and immediate access to the Fox River Trail right outside your front door. Perfect for biking, jogging, or scenic walks, this location combines outdoor recreation with small-town charm. This 2-bedroom, 1-bath home offers 1,200 sq. ft. of living space filled with natural light. The inviting living room features warm wood-accent walls, a bay window overlooking the park and river, and an open layout that flows into the dining space-ideal for entertaining. The bright kitchen has vaulted ceilings, tile flooring, and plenty of potential for customization. A full basement provides additional storage or expansion space. Car lovers, mechanics, and hobbyists will appreciate the oversized 3-car garage with an extra-high overhead door, perfect for storing boats, RVs, and other outdoor toys. A storage shed is also included. The spacious deck is ideal for morning coffee, weekend BBQs, and watching the sunset over the water. Located just minutes from downtown Oswego's shops, restaurants, and community events, this property offers both tranquility and convenience. Whether you're seeking a single-family home with river views, a vacation home in Oswego, or a prime redevelopment lot in Kendall County, 34 N Adams St is a one-of-a-kind opportunity.

34 N Adams Street, Oswego

$1,150,000

5 Beds ⋅ 5 Baths ⋅ 12644617 MLS ⋅ ACTIVE Status

Welcome to the historic Gaylord House & Gardens, a truly extraordinary estate where timeless character, modern comfort, and endless possibilities come together on just over 5 picturesque acres. Originally built in 1865, this property is rich in local history and offers a rare opportunity to own a one-of-a-kind country retreat with unmatched charm, ample acreage, and exceptional special use potential. Every detail of this remarkable home showcases timeless craftsmanship and thoughtful livability. With 5 bedrooms and 4.5 bathrooms, the home offers a generous and well balanced layout designed to accommodate comfortable living and entertaining. Original woodwork, hardwood flooring, and stunning architectural details have been beautifully preserved throughout. Multiple living spaces create a warm and inviting atmosphere, highlighted by two wood burning fireplaces, a finished attic, walkout basement, private elevator, wine cellar, and screened in patio. A thoughtfully integrated 2008 addition expands the home while honoring its original character and architectural integrity. The vintage 1901 piano located in the dining room is also included with the sale, adding yet another touch of timeless elegance. Outside, the scenic grounds are surrounded by mature trees, open green space, and protective security fencing that lines the property, offering both beauty and privacy while creating an ideal setting for pets and children. The property features a large barn ideal for gatherings or events, a chicken barn, two workshops, a machine shed, and two spacious pastures, making it perfectly suited for horses, hobby farming, entertaining, or recreational use. Electric service is available to all exterior structures. Whether you are envisioning a private estate, boutique event venue, bed and breakfast, or peaceful countryside homestead, this property offers incredible potential. The property is zoned R3 SU, offering additional flexibility and opportunity for a variety of uses. Known as the Gaylord House & Gardens, this exceptional property combines historic significance with the serenity of country living while remaining conveniently close to shopping, dining, and everyday amenities. The opportunity to own an estate of this caliber and one of Kendall County's most distinctive landmark properties is truly once in a lifetime. Experience the beauty, presence and endless potential by scheduling your private showing today.

1542 Plainfield Road, Oswego

$579,000

3 Beds ⋅ 3 Baths ⋅ 12634234 MLS ⋅ PRICE CHANGE Status

Take a look at this amazing property, 2.6 acres on the Fox River in Oswego property features two homes. 1st ranch 3 bedrooms with a walkout basement, second Ranch 3 bedrooms overlooking the Fox River. These two homes can work perfectly for families that would like to keep their in-laws, moms, and dads close to them. Property offers 34X40 Pole building Room to grow let the kids outside they can run all day long with your own personal park right on the rivers Plenty of fishing Let the kid skip stones across the river all day long, Property features a small pond down by the river. Plenty of room for friends and families camp out by the river bonfires Country life it gets no better. Minutes from downtown Oswego offers school bus pickup for the Kids. Close all the shopping restaurants that the area has to offer. This is an estate sale property being sold as is This is private property will be shown by appointment only

2110 A-B State Route 31 Route, Oswego

$429,900

5 Beds ⋅ 3 Baths ⋅ 12613328 MLS ⋅ PENDING Status

Welcome to this fantastic 5-bedroom, 2.5-bathroom home in highly sought-after Oswego, offering an exceptional layout designed for modern living. Step inside and discover a spacious and inviting floor plan perfect for families of all sizes. Upstairs, you'll find four generously sized bedrooms, each providing ample space and natural light. These versatile rooms offer the perfect environment for a dedicated home office, e-learning stations, or simply comfortable private retreats. Great loft area that can be used an extra office space, reading nook, you name it. The true highlight of this property extends outdoors to the large, private yard - an ideal setting for entertaining, gardening, or simply enjoying the beautiful Illinois seasons. Located in a desirable Oswego neighborhood, this home offers convenience to local amenities, schools, and parks. Don't miss the opportunity to make this versatile and spacious property your new home!

206 Washington Street, Oswego

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