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Detached Single · Oswego, IL
$1,150,000
5 beds · 4.5 baths · 6,050 sqft
1542 Plainfield Road, Oswego, IL, 60543
A brick-and-mortar place to make your own — room to make it home.
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What’s special

Central air2.5-car garage5.24-acre lotIn-unit laundry
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.
— the listing agent’s description

The home

5 beds
4.5 baths
6,050 sqft
Built in 1865
5.24-acre lot
2.5-car garage
Detached Single
Farmhouse

What it’ll cost

$190 / sqft
$17,190 taxes / yr
No HOA
13 days on dwello

Estimated monthly payment

$7,883/mo
Principal & interest$6,115
Property taxes$1,433
Homeowners insurance$335
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Tour this home

In person, on your schedule — a dwello agent meets you there.
WED
Jun 3
THU
Jun 4
FRI
Jun 5
SAT
Jun 6
11:00 am
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13 days on dwello
Price history
Listed for sale
May 20, 2026
$1,150,000
Earlier records
Sold
Apr 24, 2025
$867,500
Sold
May 26, 2017
$93,800
From MLS records — independently verify.
Property taxes
2025
Annual tax bill (MLS)
$17,190/yr
From county records — verify with the assessor.

Features

Central AirZonedNatural GasForced AirSteamBaseboardRadiator(s)Radiant FloorBrick
Neighborhood
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MLS listing dataMRED
Listed by Robert Grilli · Jameson Sotheby's Intl Realty
Listing last updated Jun 2, 2026 · data refreshed from the MLS Jun 17, 2026, 6:22 PM CT
Based on information submitted to the MLS GRID as of Jun 17, 2026, 6:22 PM CT. Listing data © MRED LLC, distributed by MLS GRID — deemed reliable but not guaranteed; independently verify. Anything shown below this point is not MLS listing data.
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