1542 Plainfield Road
Oswego, IL, 60543 $ 1,150,000
Bedrooms5 Baths4.1 Sq 6,050 Monthly Estimate*
$ 7,261
for $1,150,000 with 5 bedrooms and 4 full baths, 1 half bath. This 6,050 square foot home was built in 1865 on a lot size of 5.24.
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.
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FeaturesGeneralLiving Area 6050
Sewer Septic Tank
Heating Natural Gas Forced Air Steam Baseboard Radiator(s) Zoned Radiant Floor
Cooling Central Air Zoned
Possession Closing
Roof Asphalt
Appliances Range Microwave Dishwasher High End Refrigerator Freezer Washer Dryer Disposal Water Softener Owned
HOA Fee 0
Garage Spaces 2.5
Association Fee Includes None
Architectural Style Farmhouse
Construction Materials Brick
Year Built 1865
Electric Circuit Breakers
Township Oswego
Tax Year 2025
Ownership Fee Simple
Community Features Gated Street Paved
Accessibility Door Width 32 Inches or More Hall Width 36 Inches or More Stair Lift Grab Bars Throughout Roll-In Shower Wheelchair Accessible Wheelchair Ramp(s)
Assoc Fee Paid Per Not Applicable
County Kendall
New Construction N
Property Type Residential Detached Single
Other Structures Workshop Barn(s) Outbuilding Poultry Coop Shed(s)
Total Rooms 12
Full Baths 4
Status Active
Directions From W Lockport St (IL-126) R on Ridge Rd (CR-22) L on Plainfield Rd
City Oswego
High School District 308
MLS Area Oswego
Tax Annual Amount 17190
Additional Parcels Y/N N
Standard Status Active
Middle/Junior School District 308
Elementary School District 308
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InteriorInterior Amenities Cathedral Ceiling(s) Elevator 1st Floor Bedroom In-Law Floorplan 1st Floor Full Bath Built-in Features Walk-In Closet(s) Bookcases Historic/Period Mlwk Special Millwork Workshop
Basement Finished Full
Flooring Hardwood
Total Fireplaces 2
Fireplace Features Wood Burning Gas Starter
Half Baths 1
Laundry Features Sink
Total Bedrooms 5
Below Grade Finished Area 1561
Room Type Bedroom 5 Screened Porch Attic Exercise Room Recreation Room
Total Baths 5
Bedrooms Possible 5
Bathroom Whirlpool Steam Shower Double Sink Soaking Tub
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ExteriorExterior Amenities Hot Tub
Parking Features Asphalt Other Garage Door Opener Yes Garage Owned Detached Garage
Lot Features Landscaped Mature Trees Pasture
Water Source Well
Total Parking 2.5
Foundation Details Block
Lot Dimensions 208817
Lot Size Acres 5.24
Waterfront Y/N N
Other Equipment Water-Softener Owned CO Detectors Ceiling Fan(s) Sump Pump
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* Excluded FeaturesList ByJameson Sotheby's Intl RealtyBroker
realty.bobbyg@gmail.com; realty.bobbyg@gmail.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $7,261
- Monthly Property Taxes
- $1,433
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Oswego, IL
Average List Price $570,606
Percent of Sale Price 50%
About Oswego, IL 31,545 Population
130% Since 2002
$ 94,639 Median Income
36.59 Median Age
44% Households with Children
Trends Information provided by ATTOM Data Solutions.
566318 Elementary School
567529 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 5/20/2026 | $1,150,000 | | Listed Price |