Oswego Real Estate Search

Oswego Properties between $1,000,000 and $1,500,000 for Sale

Our website features the best real estate search for between $1,000,000 and $1,500,000 properties available in Oswego and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Oswego Properties between $1,000,000 and $1,500,000 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

$1,099,000
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

$1,150,000
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

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