1542 Plainfield Road, Oswego, IL 60543

• 5 beds |
• 5 baths |
• 6,050 sqft

Property 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.

Listing Status:

Active

Data Last Updated:

May 20, 2026 at 10:18PM

Listing Office:

Jameson Sotheby's Intl Realty : 708-337-2385

Listing Agent:

Robert Grilli : 708-337-2385

MLS ID:

12644617

Interior

• General: Cathedral Ceiling(s)Elevator1st Floor BedroomIn-Law Floorplan1st Floor Full BathBuilt-in FeaturesWalk-In Closet(s)BookcasesHistoric/Period MlwkSpecial MillworkWorkshop
• Rooms: Bedroom 5Screened PorchAtticExercise RoomRecreation Room
• Master Bath: WhirlpoolSteam ShowerDouble SinkSoaking Tub
• Appliances: RangeMicrowaveDishwasherHigh End RefrigeratorFreezerWasherDryerDisposalWater Softener Owned
• Dining: Separate
• Laundry: Sink
• Basement: FinishedFull
• Flooring: Hardwood
• A/C: Central AirZoned
• Heating: Natural GasForced AirSteamBaseboardRadiator(s)ZonedRadiant Floor
• Fireplace: Wood BurningGas StarterFireplaces: 2
• Disability Feature: Yes

Exterior

• General: Hot Tub
• Style: Farmhouse
• Other Structures: WorkshopBarn(s)GazeboGreenhousePoultry CoopShed(s)
• Parking: AsphaltOtherGarage Door OpenerYesGarage OwnedDetachedGarageParking spaces: 2

Construction

• Roofing: Asphalt
• Windows: Skylight(s)
• General: 2 StoriesBlock

Location

• HOA Amenities: Horse-Riding AreaGatedStreet Paved0.0Not Applicable
• Originating MLS: mred
• School District: 308
• County: Kendall

Lot

• Zoning: 0335377003
• Fencing: Fenced

Utilities

• Utilities: Circuit Breakers
• Water: Well
• Sewer: Septic Tank

Financial

• Source: mred
• Ownership: Fee Simple