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1542 Plainfield Rd , Oswego, IL 60543
$1,150,000
Est. Payment: $6,170.29/mo
5 Bed
5 Bath
6050 Sqft
5.24 Acres
Status: active | Days on site: 129
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House Description

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.

Highlights

Listed by Alexandra Morgan , 203-721-2238 Jameson Sotheby's Intl Realty , 312-751-0300. Midwest Real Estate Data mls logo

Property Type

Residential

Lot/Acreage
5.24

Year Built

1865

County

Kendall

Area

Oswego

School District

308

Listing ID

12644617

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:5
  • ▪ Bathrooms:5
  • ▪ Full Bathrooms:4
  • ▪ 1/2 Bathrooms:1
Appliances:Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Water Softener Owned, Water-Softener Owned,CO Detectors,Ceiling Fan(s),Sump Pump
Air Cond:Central Air,Zoned
Fireplaces:Wood Burning,Gas Starter
Floor:Hardwood
Below Ground Sq Ft:1561
Basement:Finished,Full
Other:
  • ▪ Additional: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
Water:Well

Exterior Features

Lot:Landscaped,Mature Trees,Pasture
Lot Dimensions:208817
Roof:Asphalt
Others:
  • ▪ Additional:Hot Tub
Sewer:Septic Tank
Parking Features:Asphalt,Garage Door Opener,Yes,Garage Owned,Detached,Garage
Principal Interest
$6,170
Taxes
$1,433

Home Price

$1,150,000

Loan Details

30 yrs
7.08%

Down Payment

20%
$230,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$6,170.29

Principal

Taxes

Principal Taxes HOA Total
Monthly $6,170.29 $1,432.50 $0.00 $7,602.79
Yearly $74,043.50 $17,190.00 $0.00 $91,233.50
Total $2,221,305.12 $515,700.00 $0.00 $2,737,005.12
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Master Chief
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Market insight data is pulled from the same city as the listing being viewed (Oswego, IL).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information submitted to the MRED as of the date listed below. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. 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. IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed by MTP or MRED. The use of the MRED Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.

Based on information submitted to the MLS GRID as of the date listed below. All data is obtained from various sources and may not have been verified by broker or MLS GRID. 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. IDX information is provided exclusively for consumers' personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability. Some listings have been excluded from this website.

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Data last updated: 2026-10-27T06:57:04.000Z

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