1542 Plainfield Road — Oswego, IL 60543
Active
Oswego, IL 60543

1542 Plainfield Road

$1,150,000
5 beds · 5 baths · 6,050 sqft
Listed at $1,150,000 13 days on market $17,190/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$1,150,000
List price
6,050
Square feet
5
Bedrooms
4 full / 1 half
Bathrooms
1865
Year built
5.24 ac
Lot size
2.5
Garage spaces
$17,190
Annual taxes
Farmhouse
Style
13
Days on market
04Features
Heating
Natural GasForced AirSteamBaseboardRadiator(s)ZonedRadiant Floor
Cooling
Central AirZoned
Appliances
RangeMicrowaveDishwasherHigh End RefrigeratorFreezerWasherDryerDisposalWater Softener Owned
Parking
AsphaltOtherGarage Door OpenerGarage OwnedDetachedGarage
Construction
Brick
Equipment
Water-Softener OwnedCO DetectorsCeiling Fan(s)Sump Pump
Sewer
Septic Tank
05Neighborhood
  • Nothing surfaced nearby in our maps data.
  • Nothing surfaced nearby in our maps data.
  • Ashgate Park 0.8 mi
  • Timber Wood Park 1.0 mi
  • Community Park at Grande Park 1.3 mi
  • Silverleaf Park 1.4 mi
  • Nothing surfaced nearby in our maps data.
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

May 20, 2026
Listed for saleThis listing
Jameson Sotheby's Intl Realty
$1,150,000
Apr 24, 2025
Sold
john greene, Realtor · 12 days on market
$867,500
May 26, 2017
Sold
HOUSE 2 HOME REALTY · 63 days on market
$93,800
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

Real answers about this home — pricing, schools, what to ask, anything.

08See it for yourself

Stand in the kitchen.
See the light at 4pm.

Photos can only do so much. Pick a time — we'll meet you at the door.

Connect with Ewelina, Anna, or Nadeem — real people on our team, no call centers.
09Similar homes
Listed by Jameson Sotheby's Intl Realty · Robert Grilli
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12644617
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