Quick Oswego IL MLS Search

Browse All Oswego IL Above $1M Properties for Sale

$1,295,000
4 Beds 5 Baths 12694808 MLS CONTINGENT 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

$1,000,000
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

$1,100,000
4 Beds 5 Baths 12692205 MLS ACTIVE Status
Attention nature lovers, beautiful 5 bedroom, 4.1 bath home with finished lookout basement and oversized 3 car garage nestled among a wooded back drop of mature trees and open space that offers both tranquility and privacy. This home boasts of its many upgrades including hardwood floors, custom ceilings, beams, trim and moldings. As you enter the home you are immediately greeted by a 2 story foyer with a unique chandelier, formal dining room with bump out for a hutch, spacious living room, 1st floor office, mud room with sink, freezer and 4 built in cubbies ,2 story family room with gas log fireplace, gourmet kitchen with 9 ft island w/granite countertops, walk in pantry with custom glass door, artisan hand crafted tiles, double oven, convection /air fryer/ microwave ,cook top and mini beverage fridge, spacious primary suite with sitting room that overlooks the woods, luxury bath with heated bubble tub, separate rain shower with wall jets, huge walk-in closet and secondary walk-in closet, additional bedrooms are all generously sized and bedroom 4 has a private bath, double French doors to a second floor bonus room, the deep pour, lookout basement features a full bath that adjoins a 5th bedroom as well as an open rec room with luxury plank vinyl flooring throughout, High eff furnace, humidifier, active radon system, water softener, hardwater filter, reverse osmosis and sulfur treatment system and more! Additional lot 45 is also available. This home will not disappoint and is ready for immediate occupancy!

7206 Fitkins Drive, Oswego

$1,099,000
5 Beds 4 Baths 12684348 MLS PRICE CHANGE 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

$1,395,000
5 Beds 6 Baths 12679849 MLS CONTINGENT Status
**Unrivaled Value. Ultimate Privacy. Unmatched Space.** Why compromise on acreage and square footage when you can have it all in Oswego? Step into refined elegance with this exceptional custom estate, set behind a private gate in prestigious Grove Estates. In Oswego, your money simply goes further-giving you the kind of sprawling, ultra-luxury compound that would cost millions more closer to the city. Since purchasing, the owner has dramatically expanded this estate, capitalizing on Oswego's generous lot sizes by adding **1.5+ additional acres across two cleared lots**. The entire massive property is now enclosed with high-end wrought iron fencing and features a newly added custom brick-paver side driveway with an oversized roundabout. Inside, the home balances grand scale with everyday comfort, featuring fresh paint throughout and a brand-new custom dog bath in the main-floor utility room. ### **Estate Highlights:** * **Unbelievable Acreage:** A massive, fully fenced private lot with two patios, dramatic uplighting, mature trees, and endless room to breathe. * **Architectural Grandeur:** Striking brick & stone exterior, a welcoming courtyard, and soaring interior spaces featuring crown molding, coffered ceilings, and wainscoting. * **Soaring Two-Story Family Room:** Framed by floor-to-ceiling windows and a dramatic stone fireplace. * **A True Chef's Kitchen:** Premium Brakur cabinetry, top-tier Wolf & Sub-Zero appliances, a massive 9-foot island, and granite finishes. * **Palatial Primary Suite:** Your own private wing complete with a sitting room, wet bar, dual-sided fireplace, spa-inspired bath, and a boutique-style walk-in closet. * **Finished Entertainer's Basement:** Complete with a private home theater, massive rec room, guest suite, full bath, and fireplace. * **Top-Tier Education:** Located in the highly acclaimed Oswego School District. --- **The Oswego Advantage:** Get the sprawling land, custom square footage, and high-end privacy you deserve, without the restrictive price tag of other luxury enclaves. This is luxury, privacy, and lifestyle-scaled up.

4779 Lees Court, 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

$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

$1,385,000
5 Beds 7 Baths 12540088 MLS ACTIVE Status
Nestled on a picturesque 3-acre wooded lot, 53 Abbeyfeale offers the perfect blend of luxury, space, and country living. This remarkable custom-built property welcomes chickens, making it an ideal haven for those who love animals and the outdoors. Boasting over 7,000 square feet of finished living space, this home features a huge wrap-around deck-perfect for entertaining or simply enjoying the tranquil natural surroundings. The home has been freshly painted both inside and out, providing a bright and inviting atmosphere throughout. This estate offers five spacious bedrooms and seven bathrooms-five full and two half baths. The first-floor primary suite provides comfort and privacy, while four of the bedrooms each have their own dedicated full bathroom. 4 fireplaces add warmth and comfort throughout the colder months. An additional fifth bedroom is located on the second floor. The home is adorned with tray ceilings featuring indirect lighting, cathedral ceilings, and beautiful Brazilian cherry hardwood floors. The open layout creates a seamless flow between living areas, enhancing both everyday living and entertaining. The gourmet kitchen includes a breakfast room, marble floors with granite inserts, huge Island with double sinks and is designed to delight any culinary enthusiast. With four separate heating and cooling zones, the home ensures comfort in every season. The finished walk-out basement expands the living space further, offering a full wet bar and a complete second kitchen-ideal for gatherings or extended family stays. Enjoy movie nights in the dedicated theater room, which features three rows of theater seating. A spacious game room provides opportunities for fun and relaxation. The basement also includes a full bathroom with a steam shower for a spa-like experience. Step outside to the enclosed gazebo, thoughtfully designed with retractable hurricane shutters, offering a peaceful retreat in any weather. The huge 3 car heated garage has 12-foot ceilings and a dedicated furnace with a car lift allowing extra storage for additional cars. Inground sprinkler, system, CertainTeed Carriage House 40-year shingles comprise the roof. Fantastic Oswego School district 308, enjoy the country life but just minutes to shopping and dining. Call for your private showing today!

53 Abbeyfeale Drive, 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

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Above $1 Million Oswego Real Estate

Our website features the best real estate search for above $1 million 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. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!