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$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

$1,100,000
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

$1,139,528
11919763 MLS ACTIVE Status
Ready to build your Business on Orchard Road in Fast Growing Oswego. There are 1 to 3 Retail Lots available on the East side of Orchard Road and north of the Lewis Stoplight. Redwood Apartments are being built as we speak behind this location as well as all the way to the north to Mill Road. This is for Lots 1, 2 & 3. ALL THREE LOTS. Please note you will have to put in your own access road. There are three Retail Lots available Price is $8.00psf ( PER SQUARE FOOT) Lot 3 is 1.18 or 51,400sf x $8.00psf = $411,206.40; Lot 2 is 1.33 acres or 57,934 sf x $8.00 = $463,478.40.00; Lot 1 is .76 acre or 33,105sf x $8.00psf = $264,844.00.00. All Three Lots for $1,139,528.00. There is a stub road coming off or Lewis, that means lot 1 & 2 do not have direct access and will need access from lot 3. At $8.00 per square foot this is a great deal for Retail on Orchard Road.

123 Orchard Road, Oswego



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