1542 Plainfield Rd Oswego, IL 60543
South Oswego NeighborhoodEstimated payment $7,742/month
Highlights
- Barn
- Gated Community
- Landscaped Professionally
- Spa
- 5.24 Acre Lot
- Mature Trees
About 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.
Listing Agent
Jameson Sotheby's Intl Realty Brokerage Phone: (708) 337-2385 License #475179692 Listed on: 05/20/2026
Co-Listing Agent
Jameson Sotheby's Intl Realty Brokerage Phone: (708) 337-2385 License #475211546
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $17,190
Year Built
- Built in 1865
Lot Details
- 5.24 Acre Lot
- Poultry Coop
- Fenced
- Landscaped Professionally
- Paved or Partially Paved Lot
- Mature Trees
Parking
- 2.5 Car Detached Garage
- Parking Available
- Garage Door Opener
- Driveway
- Parking Included in Price
Home Design
- Farmhouse Style Home
- Brick Exterior Construction
- Block Foundation
- Asphalt Roof
Interior Spaces
- 6,050 Sq Ft Home
- 2-Story Property
- Elevator
- Built-In Features
- Bookcases
- Historic or Period Millwork
- Cathedral Ceiling
- Ceiling Fan
- Skylights
- Wood Burning Fireplace
- Fireplace With Gas Starter
- Family Room with Fireplace
- 2 Fireplaces
- Living Room with Fireplace
- Formal Dining Room
- Recreation Room
- Workshop
- Screened Porch
- Home Gym
- Finished Attic
- Carbon Monoxide Detectors
Kitchen
- Range
- Microwave
- High End Refrigerator
- Freezer
- Dishwasher
- Disposal
Flooring
- Wood
- Radiant Floor
Bedrooms and Bathrooms
- 5 Bedrooms
- 5 Potential Bedrooms
- Main Floor Bedroom
- Walk-In Closet
- In-Law or Guest Suite
- Bathroom on Main Level
- Dual Sinks
- Whirlpool Bathtub
- Steam Shower
Laundry
- Laundry Room
- Dryer
- Washer
- Sink Near Laundry
Finished Basement
- Basement Fills Entire Space Under The House
- Sump Pump
- Finished Basement Bathroom
Accessible Home Design
- Roll-in Shower
- Grab Bars
- Halls are 36 inches wide or more
- Wheelchair Access
- Accessibility Features
- Stair Lift
- Doors are 32 inches wide or more
- Wheelchair Ramps
Outdoor Features
- Spa
- Deck
- Screened Patio
- Shed
- Outbuilding
Farming
- Barn
- Pasture
Utilities
- Forced Air Zoned Heating and Cooling System
- Radiator
- Baseboard Heating
- Heating System Uses Steam
- Heating System Uses Natural Gas
- Well
- Water Softener is Owned
- Septic Tank
Community Details
- Gated Community
Listing and Financial Details
- Homeowner Tax Exemptions
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $18,993 | $231,333 | $49,973 | $181,360 |
| 2024 | $18,993 | $239,943 | $43,836 | $196,107 |
| 2023 | $17,581 | $208,646 | $38,118 | $170,528 |
| 2022 | $17,322 | $194,996 | $35,624 | $159,372 |
| 2021 | $16,225 | $182,239 | $33,293 | $148,946 |
| 2020 | $15,893 | $176,931 | $32,323 | $144,608 |
| 2019 | $15,314 | $168,105 | $32,323 | $135,782 |
| 2018 | $15,743 | $167,169 | $32,143 | $135,026 |
| 2017 | $15,625 | $160,740 | $30,907 | $129,833 |
| 2016 | $14,997 | $152,360 | $29,296 | $123,064 |
| 2015 | $14,666 | $142,392 | $27,379 | $115,013 |
| 2014 | -- | $136,915 | $26,326 | $110,589 |
| 2013 | -- | $138,298 | $26,592 | $111,706 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 08/18/2026 08/18/26 | For Sale | $1,150,000 | 0.0% | $190 / Sq Ft | |
| 08/04/2026 08/04/26 | Off Market | $1,150,000 | -- | -- | |
| 05/20/2026 05/20/26 | For Sale | $1,150,000 | +32.6% | $190 / Sq Ft | |
| 04/24/2025 04/24/25 | Sold | $867,500 | -3.6% | $173 / Sq Ft | View Prior Sale |
| 03/24/2025 03/24/25 | Pending | -- | -- | -- | |
| 03/13/2025 03/13/25 | For Sale | $900,000 | +12.6% | $180 / Sq Ft | |
| 03/25/2024 03/25/24 | Sold | $799,000 | 0.0% | $160 / Sq Ft | View Prior Sale |
| 01/24/2024 01/24/24 | Pending | -- | -- | -- | |
| 12/18/2023 12/18/23 | For Sale | $799,000 | -- | $160 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $867,500 | Fidelity National Title | |
| Warranty Deed | $799,000 | None Listed On Document | |
| Warranty Deed | $286,500 | Fidelity National Title Co | |
| Warranty Deed | -- | Attorney | |
| Deed | $660,000 | First American Title | |
| Interfamily Deed Transfer | -- | Attorney | |
| Quit Claim Deed | -- | None Available | |
| Deed | $280,000 | -- | |
| Deed | $192,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $422,500 | New Conventional | |
| Previous Owner | $639,200 | New Conventional | |
| Previous Owner | $363,000 | New Conventional | |
| Previous Owner | $502,000 | Commercial | |
| Previous Owner | $260,000 | New Conventional | |
| Previous Owner | $340,000 | New Conventional | |
| Previous Owner | $380,000 | Unknown | |
| Previous Owner | $250,000 | Unknown | |
| Previous Owner | $100,000 | Credit Line Revolving |
Source: Midwest Real Estate Data (MRED)
MLS Number: 12644617
APN: 03-35-377-003
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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. Some IDX listings have been excluded from this website.
Listings courtesy of Midwest Real Estate Data (MRED) as distributed by MLS GRID.
Based on information submitted to the MLS GRID
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Ask me questions while you tour the home.