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Browse All Oswego IL Above $1M Properties for Sale

$1,200,000
7 Beds 6 Baths 12750633 MLS ACTIVE Status
Some homes you see. This one, you feel the moment you step inside. This extraordinary 7-bedroom, 6-bath waterfront estate brings extensive renovations, exceptional craftsmanship, and true resort-style living together on a truly remarkable property. Set along Waubonsie Creek, this expansive home offers incredible flexibility for everyday living, entertaining, multi-generational needs, and guests. The main level has been beautifully transformed with new oak hardwood flooring, fresh paint, updated lighting and plumbing fixtures, and impeccable trim work throughout. At the heart of the home is a completely renovated kitchen, thoughtfully redesigned with wall-to-ceiling custom cabinetry, integrated lighting, quartz countertops, double ovens, and a spacious eat-in area overlooking the pool. Direct access to the screened-in porch creates a seamless connection between indoor and outdoor living. Formal living and dining spaces provide an elegant backdrop for entertaining, while the dramatic two-story family room fills with natural light and centers around a striking masonry fireplace, framing views of the yard and pool beyond. Down the hall, a second fireplace warms the library, creating an inviting retreat for quiet mornings or evening conversation. The first-floor primary suite is a private sanctuary, crowned by soaring coffered, 10-foot ceilings. The completely renovated spa-inspired bath is where the home truly indulges - an oversized walk-in shower, a stand-alone soaking tub, heated floors, and custom tile, sinks, and vanity come together for a retreat that rivals any five-star escape. A custom lower staircase and all-new carpeting further elevate the home's impressive interior. A brand-new mudroom, designed specifically with poolside living in mind, offers direct access to the pool along with custom benches, built-in drawers for pool towels, a new dog wash, new tile and lighting, and an oversized pantry closet. Upstairs, five bedrooms provide exceptional space and versatility, many crowned with soaring vaulted ceilings. One features a private en-suite bath and walk-in closet, while another includes a custom built-in bunk bed, ideal for children, grandkids, or overnight guests. The remaining bedrooms are complemented by a beautifully updated shared full bathroom, including a newly renovated hall bathroom. The walk-out lower level expands the possibilities even further. A separate suite with a bedroom, full closet, and full bath offers outstanding potential for multi-generational living, an in-law arrangement, or extended-stay guests. The spacious recreation area gathers around the home's third masonry fireplace, with abundant storage and a renovated wine room featuring new wine shelving and custom tile. Outside, the property becomes a private oasis with an in-ground pool, large screened-in porch, dog run, waterfront setting, and expansive grounds designed for both relaxation and entertaining. Car enthusiasts will appreciate the home's exceptional five-car garage capacity. The three-car side-load garage features brand-new epoxy flooring, while the walk-out lower level provides an additional two-car tandem garage, creating tremendous flexibility for vehicles, recreational equipment, storage, or workshop space. A turnaround driveway adds everyday convenience. Additional highlights include Pella windows, several new appliances, and extensive updates throughout the home. The village is also installing a new parkway walkway in front of the property that will connect to a larger path system, adding even more appeal for those who enjoy walking, biking, and the outdoors. The home was converted to the new 2" city water in September and sewer in August (with the well kept intact to serve the pool and irrigation needs). This is more than a home. It is a waterfront estate designed for the way you want to live, with exceptional entertaining possibilities, resort-style outdoor living, and thoughtful craftsmanship at every turn. Schedule today

3663 Wolf Road, Oswego

$1,295,000
4 Beds 5 Baths 12694808 MLS PENDING Status
The ULTIMATE INDOOR SPORTS COMPLEX! Whether you're sinking three-pointers, hosting pickleball tournaments, practicing volleyball, flipping through gymnastics routines, rolling out yoga mats, or scoring a goal, this incredible 1600 sq ft indoor sports court (with sound absorbing panels) is unlike anything you've seen! Rain, snow, or scorching summer heat-it doesn't matter. The game is always on! Add the adjoining weight room, and every workout, practice, celebration, and family gathering happens right at home. And when the final buzzer sounds... it's time to make a splash outdoors! Centered around a spectacular 16' x 37' fiberglass saltwater pool with custom tile patio, automatic cover, and an easy-care chlorine-generating system, this outdoor space was designed for making family memories! This one-acre property with 22-zone irrigation system makes every day feel like a vacation! The sports court & pool may steal the spotlight...but the attached luxury home will steal your heart! Built in 2021, this one-of-a-kind custom estate blends modern luxury with thoughtful design at every turn. The breathtaking two-story family room features 20-foot ceilings, a dramatic floor-to-ceiling fireplace, and walls of windows that flood the home with natural light. A large interior picture window offers a direct view of the sports court, so you'll never miss the action. The chef's kitchen is as beautiful as it is functional, showcasing high-end JennAir appliances, a large center island, and everyone's favorite feature-a hidden walk-in pantry! The adjacent dining room is perfect for everything from casual family dinners to holiday gatherings, while the private office, custom plantation shutters throughout, elegant wide baseboards, and an oversized mudroom elevate everyday living. Upstairs you'll find four spacious bedrooms, including a primary suite with a tray ceiling and an large walk-in closet. The second bedroom also features its own walk-in closet, while the third bedroom offers the privacy of an attached ensuite bath. An enormous linen closet provides exceptional storage, and the thoughtfully designed laundry room is a dream with abundant cabinetry, built-in pull-out laundry hampers, two full-size washer/dryer combinations, plus a convenient pedestal washer that's perfect for small loads, delicates, or athletic wear. The finished basement level keeps the fun going with the incredible indoor sports court, adjoining weight room, ample storage closet, spacious recreation room, full bar (with gas and plumbing), an additional bedroom, and a full bathroom with direct access to the pool-perfect for rinsing off after a swim. Additional highlights include a four-car garage, dual HVAC, smart home technology for the thermostat and appliances, and a timeless Hardie Board and brick exterior designed for lasting beauty. Located in prestigious Henneberry Woods, surrounded by custom homes, scenic ponds, and walking trails, this is more than a luxury home - it's a lifestyle that's nearly impossible to duplicate. Train. Play. Splash. Repeat. Welcome home. (Ask your Realtor for the Video House Tour!)

4720 Waa Kee Sha Drive, Oswego

$1,099,000
5 Beds 4 Baths 12684348 MLS ACTIVE Status
Welcome to 14 Abbeyfeale Drive, an extraordinary executive estate nestled on 2.2 beautifully landscaped acres in one of Oswego's most prestigious settings. Offering over-the-top quality, exceptional craftsmanship, and luxurious amenities throughout, this stunning move-in-ready residence features 5 bedrooms, a private office, 4 full bathrooms, a deep-pour finished basement, and an oversized 4-car garage. From the moment you enter, the grand two-story foyer with its elegant chandelier sets the tone for the sophistication found throughout the home. Rich premium walnut hardwood flooring spans the main level, complemented by solid wood paneled doors, custom millwork, and detailed trim surrounding every door and window. Picturesque windows adorned with plantation shutters flood the home with natural light while showcasing breathtaking views of the surrounding property. Designed for both everyday living and entertaining, the custom chef's kitchen is a true showpiece featuring high-end finishes, abundant workspace, and a large center island complete with a prep sink. The adjacent family room offers built-in shelving, a grand fireplace, and spectacular views of the backyard oasis. The thoughtfully designed main level includes a first-floor bedroom and full bathroom, ideal for guests or multi-generational living. Two separate staircases lead to the second floor, including a discreet secondary staircase equipped with a chairlift for added accessibility. Upstairs, you'll find four generously sized bedrooms, including a luxurious primary suite that serves as a private retreat. The owner's suite features a cozy fireplace sitting area, spacious walk-in closet, and spa-inspired bathroom with heated floors. Every bathroom in the home, except the basement bath, offers the comfort of heated flooring. One secondary bedroom also provides convenient access to additional attic storage. The finished deep-pour basement expands the living space with a dedicated theater room, large office or potential guest suite, full bathroom, recreation area, television lounge, expansive utility room, and an oversized storage room with built-in shelving. Step outside and discover your own private resort. The meticulously maintained grounds feature professional landscaping, a paver patio with fire pit, expansive wood deck, outdoor speaker system, and a dedicated area to practice your golf swing. Sports enthusiasts will appreciate the private pickleball court, while the expansive yard offers endless opportunities for recreation and relaxation. With oversized bedrooms, exceptional attention to detail, premium finishes, and an unmatched blend of luxury and functionality, 14 Abbeyfeale Drive presents a rare opportunity to own one of Oswego's finest executive homes.

14 Abbeyfeale Drive, 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
12659374 MLS ACTIVE Status
Rare opportunity to acquire a long-term, single-tenant NNN dental office investment located in Oswego's rapidly growing commercial corridor. Positioned on a 1.37 Acre site with high visibility, this all-brick medical asset consists of 3,950 SF of finished dental office space plus an additional 1,950 SF unfinished lower level, totaling approximately 6,000 SF. The 3,950 SF main level was purpose built for efficient patient flow and includes a spacious reception area with vaulted ceilings, 8 operatories with rear delivery and nitrous oxide lines, training/conference room, Dr's Office, lab space, sterilization room, x-ray room, 2 restrooms, and a staff break room. The property has long been occupied by Kendall Pointe Dental, operating under D1 Support, LLC, an affiliated practice within the DecisionOne Dental Partners network. DecisionOne Dental Partners is a growing regional dental support organization with a substantial Illinois footprint, providing investors exposure to an established healthcare operator within the defensive medical office sector. Tenant has been in place since 2016 and recently executed a 5-year lease extension through September 30, 2031, providing investors with reliable cash flow and long-term occupancy stability. Lease structure provides a favorable expense profile with tenant responsibility for real estate taxes, utilities, janitorial, landscaping, snow removal, refuse, HVAC servicing, and interior maintenance obligations. Building has been very well maintained, benefiting from significant recent capital improvements including a new roof installed in 2024 and mechanical system replacements completed in 2023. Positioned near major commuter corridors including US Route 30 and US Route 34, the property benefits from strong suburban demographics, established residential density, and continued population growth throughout Kendall County. Healthcare real estate continues to demonstrate long-term resiliency, making this offering an attractive opportunity for private investors, 1031 exchange buyers, and medical office investors seeking stable tenancy and reduced management intensity.

1991 Wiesbrook 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

$1,499,000
5 Beds 4 Baths 12526887 MLS ACTIVE Status
Private 14.4-Acre Creekfront Estate | 4,800+ Sq Ft | Designed for Living, Creating & Expanding! Welcome to 1502 Cherry Rd - a one-of-a-kind estate where privacy, space, and luxury converge on over 14 pristine acres in Oswego, IL. Designed for those who demand the extraordinary, this stunning ranch offers a lifestyle rarely found at any price. Step inside and discover a thoughtfully designed floor plan centered around two main-level master suites - ideal for multigenerational living, long-term guests, or a private owner's retreat. The Finished Room Over Garage (FROG) adds even more versatility, whether you envision a home office, media room, playroom, or additional guest suite. The property's crown jewel is its unmatched garage and storage infrastructure. A 4-car attached garage paired with a massive pole barn delivers the kind of space that car collectors, hobbyists, equipment owners, and entrepreneurs dream about. Bring your classics, your toys, your tools - there is room for all of it. Outdoors, over 14 acres of picturesque land surround you with room to roam, entertain, or simply breathe. The estate's natural setting provides the seclusion of country living while remaining just minutes from everyday conveniences in Oswego and a short drive to the greater Chicagoland area. Additional highlights include a thoughtful ranch layout, generous living spaces, and a character and quality that must be experienced in person to be fully appreciated. This is not just a home - it is a private retreat built for a buyer who has earned the best. Schedule your private showing today.

1502 Cherry Road, Oswego

$1,999,900
12491440 MLS ACTIVE Status
You need to check out this incredibly rare property that does not become available too often. 14.5 acres located right on the Fox River near Downtown Oswego, with its own private lake. This property has over 700' of river frontage! Amenities on this expansive property include: huge wrapping driveway that allows for extensive privacy off the main road, basketball court, playground, private lake, river frontage, 2 large sheds that can be upgraded/renovated to more livable spaces (currently just used as storage), and the best part is a massive free-standing 12,000 sq ft building equipped with elevator/full commerical kitchen (appliances/hood system/commercial dishwashing station all included)/massive event space and separate large dining space/12 dorm rooms with 4 bunk beds in each room sleeping 8 comfortably per room/laundry room/designated office spaces/designated AV room/6 bathrooms/plenty of storage/tons of furniture, supplies, dishes, cookware, tables, chairs, ect. The property also has RV hook-ups. This property has pleasant surprises around every corner, that you simply need to check out for yourself. It was being used as a spiritual retreat, but the possibilities are honestly endless for what you can do with such a unique lot: summer camp, RV park, spiritual retreat, spa retreat, tree/plant nursery, senior care facility, get a simple re-zoning and building a beautiful waterfront estate; my personal favorite idea would be to turn this into a stunning wedding reception venue since it already has the commerical kitchen for catering, large space for ceremony, dining space, dance floor, bathrooms...all of it is ready to go! Call listing agent to schedule a showing.

1626 State Route 31, Oswego

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