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.
Property Details
Price:
$1,150,000
MLS #:
MRD12644617
Status:
Active
Beds:
5
Baths:
5
Type:
Single Family
Neighborhood:
oswego
Listed Date:
May 20, 2026
Finished Sq Ft:
6,050
Year Built:
1865
See this Listing
Schools
School District:
308
Interior
Appliances
Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Water Softener Owned
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1561
Cooling
Central Air, Zoned
Fireplaces Total
2
Flooring
Hardwood
Heating
Natural Gas, Forced Air, Steam, Baseboard, Radiator(s), Zoned, Radiant Floor
Interior Features
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
Laundry Features
Sink
Exterior
Accessibility Features
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)
Architectural Style
Farmhouse
Community Features
Gated, Street Paved
Construction Materials
Brick
Exterior Features
Hot Tub
Fencing
Fenced
Garage Spaces
2.5
Lot Features
Landscaped, Mature Trees, Pasture
Other Structures
Workshop, Barn(s), Outbuilding, Poultry Coop, Shed(s)
Parking Features
Asphalt, Other, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
25
Parking Total
2.5
Patio And Porch Features
Deck, Screened
Roof
Asphalt
Window Features
Skylight(s)
Financial
HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2025
Taxes
$17,190
Map
Community
- Address1542 Plainfield Road Oswego IL
- CityOswego
- CountyKendall
- Zip Code60543
Market Summary
Current real estate data for Single Family in Oswego as of Oct 04, 2026
256
Single Family Listed
57
Avg DOM
227
Avg $ / SqFt
$521,004
Avg List Price
Property Summary
- 1542 Plainfield Road Oswego IL is a Single Family for sale in Oswego, IL, 60543. It is listed for $1,150,000 and features 5 beds, 5 baths, and has approximately 6,050 square feet of living space, and was originally constructed in 1865. The current price per square foot is $190. The average price per square foot for Single Family listings in Oswego is $227. The average listing price for Single Family in Oswego is $521,004.
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Copyright 2026. All rights reserved.
1542 Plainfield Road
Oswego, IL


