Browse All Oswego IL Historical Properties for Sale

3 Beds ⋅ 2 Baths ⋅ 12743059 MLS ⋅ ACTIVE 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

$375,000

12738206 MLS ⋅ ACTIVE Status

High-Visibility Downtown Oswego Location! Outstanding positioning at the corner corridor of Route 34 and Washington St. Exceptional foot traffic and vehicle exposure in the heart of downtown Oswego's retail and business district. The updated main level features a reception/waiting area, a conference room, half bath, and full kitchen with storage room. The full basement features a concrete encased bomb shelter! Plus storage and a bathroom in the basement. The 2nd floor features 3 offices/bedrooms and 1 full bathroom. Dedicated off-street parking. Ideal setup for professional services, boutique retail, studio, or private office space. Ample municipal parking nearby and close proximity to popular dining and community events. Move-in ready canvas to establish or grow your business in Kendall County. This property is within TIF 5 Main & Washington and could be eligible for facade grant money for exterior improvements through Oswego's Economic Incent. Award. Located in the Downtown Oswego Historic District-eligible for Federal and Illinois Historic Rehabilitation Tax Credits for qualified income-producing/commercial updates (application reqd). Current tenant is month to month and willing to stay. Each of the 3 rooms upstairs and main level conference room could be rented separately with a shared reception/waiting area. EM payable via certified funds to Coldwell Banker Real Estate Group.

6 E Washington Street, Oswego

$319,990

3 Beds ⋅ 1 Baths ⋅ 12718102 MLS ⋅ CONTINGENT Status

Nestled quietly on over half an acre of tree-lined land along Mill Road in unincorporated Oswego, the Parker House has been part of the local landscape since approximately 1836. Known by name among area historians, this home carries nearly two centuries of stories within its walls. Inside, the warmth of hardwood floors greets you as you move through a thoughtfully preserved floor plan. The family room and separate dining room combine to create a relaxing space. In the formal living room, a wood-burning stone fireplace anchors the heart of the home. The kitchen opens naturally into a sun-drenched breakfast room - a serene spot for morning coffee, afternoon reading, or simply watching the seasons change through the windows. Three bedrooms, each with hardwood flooring, carry the same quiet charm that makes this home feel inviting. Outside, mature trees, established landscaping, and a partially fenced lot create a private, peaceful setting that feels a world away - yet you're just a short walk from the Fox River and Downtown Oswego where bike and walking paths that wind through town. For those who need space to work or create, the detached 3+ car garage offers additional space to pursue these passions. The Parker House was built at a time when homes were crafted to last - and nearly 200 years later, that's exactly what it has done... solid, sturdy, and lovingly maintained, this is construction that today's new builds simply don't replicate. As with most historic homes featuring limestone foundations, occasional seepage during heavy rain is not uncommon. If you've ever dreamed of owning a piece of local history, a home with a genuine soul - come see it for yourself.

4810 Mill Road, Oswego

$360,000

2 Beds ⋅ 1 Baths ⋅ 12737349 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

$327,000

3 Beds ⋅ 2 Baths ⋅ 12734087 MLS ⋅ ACTIVE Status

PRICE REDUCTION!! Plus! a $7,000 driveway allowance in the form of "Cash back at closing." Don't miss your opportunity to own this 3-bedroom, 2-bathroom ranch nestled on a beautiful .76-acre corner lot in unincorporated Oswego with no HOA! Come in with an open mind and your personal touches! Cherished by the same family for decades, this home is in need of some updating a little TLC, but offers great bones, a solid layout, and plenty of opportunity to make it your own. Inside, you'll find three generously sized bedrooms, including a spacious primary bedroom, along with a comfortable living room and an inviting eat-in kitchen. The wood burning fireplace brings warmth and charm to the living area. The full unfinished basement provides an abundance of additional space for storage, a workshop, recreation, or future finishing possibilities. Recent updates include a new roof and HVAC system that are both under 10 years old, offering valuable peace of mind, as well as a whole home water conditioning system valued at over $6,000. While the home is in great condition, it is ready for some cosmetic updates, giving the next owner the opportunity to bring their own style and vision to this well-established property. Step outside and enjoy the privacy this expansive lot provides. Mature trees and established shrubs create a beautiful natural backdrop and a peaceful buffer around the backyard. The outdoor space is truly special, featuring a spacious brick paver patio with a built-in fireplace-perfect for entertaining, relaxing, or enjoying evenings around the fire. A charming, operating mini pond adds another unique touch to the backyard setting. If you're looking for space, privacy, and the freedom of an unincorporated location with no HOA, this Oswego ranch is full of possibilities and ready for its next chapter.

4520 Douglas Road, Oswego

$349,900

2 Beds ⋅ 1 Baths ⋅ 12697357 MLS ⋅ PENDING 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

$265,000

3 Beds ⋅ 2 Baths ⋅ 12701956 MLS ⋅ CONTINGENT 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

$950,000

4 Beds ⋅ 3 Baths ⋅ 12699328 MLS ⋅ ACTIVE Status

ENDLESS OPPORTUNITIES on 2.27 acres in Oswego! This beautifully renovated farmhouse combines character with modern updates & tons of usable space! House with over 3100 SF PLUS 1400+ SF barn, & 600 SF shed with electricity. Create your own backyard oasis by adding a pool, hot tub, or cold plunge adjacent to the large wood deck, paver patio with pergola and built-in firepit. The barn could be used for a workshop, car collection, gardening, hobbies, or home business or storage. Or create a bonus rec room/guest space in the barn which already has water, electric & heat! The farmhouse is ready for move in! Many renovation projects since 2016, the custom kitchen was completely gutted and remodeled in 2022 featuring a massive quartz island/breakfast bar, custom cabinetry wrapped around the perimeter with farmhouse sink, stainless steel appliances including a Wolf range & double ovens. Hardwood flooring, fresh paint, white trim throughout much of the home, custom two-panel doors and mostly 10-foot ceilings enhance the main level. Flexible living spaces include formal living and dining rooms, a private office, inviting family room with fireplace and sunroom overlooking the property. The main level also features remodeled powder room & laundry rooms, refreshed staircase & upstairs hallway with distinctive tin ceiling and millwork details. Upstairs, the private primary suite features a large closet and en-suite bath. Three additional bedrooms are complemented by a beautifully remodeled hall bath with dual vanities, 48-inch shower with seat, deep soaking tub, heated floors and lighted mirrors. The clean, unfinished basement has been painted, sealed and waterproofed with a perimeter French drain and offers radiant heat and excellent storage. Additional improvements include updated electrical and plumbing, new well (2017), tankless water heater and water filtration system, furnace and A/C (2013), and new roofs on both the house and barn (2018). The barn spans over two levels with exposed beams, electricity, gas line, water hookup, high-efficiency furnace, lift, a partially finished main-level bonus room. Outside, enjoy 2.27 picturesque acres with mature trees, custom covered front porch with recessed lighting and cedar posts, and a widened asphalt driveway. All of this is conveniently located near the Route 34/Douglas shopping corridor, Fox Bend Golf Course and vibrant Downtown Oswego.

3614 Wolf Road, Oswego

$598,000

2 Beds ⋅ 3 Baths ⋅ 12688017 MLS ⋅ ACTIVE Status

PRICE REDUCTION! Plus, a $20,000 Roof Allowance in the form of "Cash Back at Closing" upon a successful transaction by December 31st, 2026. Beautiful park-like 3.75 acre (+/- to be determined by boundary survey) 3 bedroom 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.***CALL DIRECTLY FOR APPOINTMENT***

6274 Us Highway 34 Highway, Oswego

$1,100,000

7 Beds ⋅ 3 Baths ⋅ 12682754 MLS ⋅ PENDING Status

Home is under contract. 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

$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 ⋅ CONTINGENT 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

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