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.
Active
$1,150,000
1542 Plainfield Rd, Oswego, IL 60543
5beds
6,050sqft
Single Family Residence
Built in 1865
5.24 Acres Lot
$-- Zestimate®
$190/sqft
$-- HOA
What's special
Chicken barnTwo wood burning fireplacesOriginal woodworkThoughtful livabilityFinished atticPrivate elevatorStunning architectural details
- 32 days |
- 1,641 |
- 119 |
Zillow last checked:
Listing updated:
Listed by:
Robert Grilli (708)337-2385,
Jameson Sotheby's Intl Realty,
Alexandra Morgan 203-721-2238,
Jameson Sotheby's Intl Realty
Source: MRED as distributed by MLS GRID,MLS#: 12644617
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Bedroom 5, Screened Porch, Attic, Exercise Room, Recreation Room
Primary bedroom
- Features: Flooring (Hardwood), Bathroom (Full)
- Level: Second
- Area: 340 Square Feet
- Dimensions: 17X20
Bedroom 2
- Features: Flooring (Hardwood)
- Level: Second
- Area: 256 Square Feet
- Dimensions: 16X16
Bedroom 3
- Features: Flooring (Hardwood)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 12X13
Bedroom 4
- Features: Flooring (Hardwood)
- Level: Second
- Area: 168 Square Feet
- Dimensions: 12X14
Bedroom 5
- Features: Flooring (Hardwood)
- Level: Main
- Area: 256 Square Feet
- Dimensions: 16X16
Other
- Level: Third
- Area: 1190 Square Feet
- Dimensions: 35X34
Dining room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 336 Square Feet
- Dimensions: 24X14
Exercise room
- Features: Flooring (Ceramic Tile)
- Level: Basement
- Area: 414 Square Feet
- Dimensions: 18X23
Family room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 675 Square Feet
- Dimensions: 27X25
Kitchen
- Features: Kitchen (Eating Area-Breakfast Bar, Pantry-Walk-in), Flooring (Hardwood)
- Level: Main
- Area: 221 Square Feet
- Dimensions: 13X17
Laundry
- Features: Flooring (Ceramic Tile)
- Level: Basement
- Area: 70 Square Feet
- Dimensions: 7X10
Living room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 360 Square Feet
- Dimensions: 18X20
Other
- Features: Flooring (Ceramic Tile)
- Level: Basement
- Area: 399 Square Feet
- Dimensions: 21X19
Screened porch
- Level: Main
- Area: 348 Square Feet
- Dimensions: 29X12
Heating
- Natural Gas, Forced Air, Steam, Baseboard, Radiator(s), Zoned, Radiant Floor
Cooling
- Central Air, Zoned
Appliances
- Included: Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Water Softener Owned
- Laundry: Sink
Features
- 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
- Flooring: Hardwood
- Windows: Skylight(s)
- Basement: Finished,Full
- Attic: Finished
- Number of fireplaces: 2
- Fireplace features: Wood Burning, Gas Starter, Family Room, Living Room
Interior area
- Total structure area: 1,561
- Total interior livable area: 6,050 sqft
- Finished area below ground: 1,561
Property
Parking
- Total spaces: 2.5
- Parking features: Asphalt, Other, Garage Door Opener, Yes, Garage Owned, Detached, Garage
- Garage spaces: 2.5
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Door Width 32 Inches or More, Hall Width 36 Inches or More, Stair Lift, Grab Bars Throughout, Roll-In Shower, Wheelchair Accessible, Wheelchair Ramp(s), Disability Access
Features
- Stories: 2
- Patio & porch: Deck, Screened
- Has spa: Yes
- Spa features: Outdoor Hot Tub
- Fencing: Fenced
Lot
- Size: 5.24 Acres
- Features: Landscaped, Mature Trees, Pasture
Details
- Additional structures: Workshop, Barn(s), Outbuilding, Poultry Coop, Shed(s)
- Parcel number: 0335377003
- Special conditions: None
- Other equipment: Water-Softener Owned, Ceiling Fan(s), Sump Pump
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Farmhouse
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Block
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1865
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Features: Gated, Street Paved
- Security: Carbon Monoxide Detector(s)
HOA
- Services included: None
Location
- Region: Oswego
Financial & listing details
- Price per square foot: $190/sqft
- Tax assessed value: $719,829
- Annual tax amount: $17,190
- Date on market: 5/22/2026
- Ownership: Fee Simple
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/22/2026 | Listed for sale | $1,150,000+32.6%$190/sqft |
Source:  MRED as distributed by MLS GRID #12644617 Report a problem | ||
| 4/24/2025 | Sold | $867,500-3.6%$143/sqft |
Source: MRED as distributed by MLS GRID #12308894 Report a problem | ||
| 3/24/2025 | Contingent | $900,000$149/sqft |
Source: MRED as distributed by MLS GRID #12308894 Report a problem | ||
| 3/13/2025 | Listed for sale | $900,000+12.6%$149/sqft |
Source: MRED as distributed by MLS GRID #12308894 Report a problem | ||
| 3/25/2024 | Sold | $799,000$132/sqft |
Source: MRED as distributed by MLS GRID #11948760 Report a problem | ||
| 3/14/2024 | Pending sale | $799,000$132/sqft |
Source: MRED as distributed by MLS GRID #11948760 Report a problem | ||
| 1/25/2024 | Contingent | $799,000$132/sqft |
Source: MRED as distributed by MLS GRID #11948760 Report a problem | ||
| 12/18/2023 | Listed for sale | $799,000+178.9%$132/sqft |
Source: MRED as distributed by MLS GRID #11948760 Report a problem | ||
| 7/1/2021 | Sold | $286,500-56.6%$47/sqft |
Source: Public Record Report a problem | ||
| 12/6/2018 | Sold | $660,000-13.2%$109/sqft |
Source: Public Record Report a problem | ||
| 9/27/2018 | Pending sale | $760,000$126/sqft |
Source: 4 Sale Realty Advantage #09995361 Report a problem | ||
| 8/17/2018 | Price change | $760,000-1.9%$126/sqft |
Source: 4 Sale Realty Advantage #09995361 Report a problem | ||
| 7/18/2018 | Price change | $775,000-2.5%$128/sqft |
Source: 4 Sale Realty Advantage #09995361 Report a problem | ||
| 6/23/2018 | Price change | $795,000-9.1%$131/sqft |
Source: 4 Sale Realty Advantage #09995361 Report a problem | ||
| 6/6/2018 | Price change | $875,000-2.2%$145/sqft |
Source: Owner Report a problem | ||
| 5/7/2018 | Listed for sale | $895,000$148/sqft |
Source: Owner Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $18,993 +5.6% | $239,943 +15% |
| 2023 | $17,983 +3.8% | $208,646 +7% |
| 2022 | $17,322 +6.8% | $194,996 +7% |
| 2021 | $16,225 +2.1% | $182,239 +3% |
| 2020 | $15,893 +0.2% | $176,931 +5.3% |
| 2019 | $15,862 | $168,105 +0.6% |
| 2018 | $15,862 +1.5% | $167,169 +4% |
| 2017 | $15,625 +4.2% | $160,740 +5.5% |
| 2016 | $14,997 +2.3% | $152,360 +7% |
| 2015 | $14,666 | $142,392 +4% |
| 2014 | $14,666 | $136,915 -1% |
| 2013 | -- | $138,298 -3% |
| 2012 | -- | $142,634 -8% |
| 2011 | -- | $155,037 -5% |
| 2010 | -- | $163,197 -2% |
| 2009 | -- | $166,567 +7.3% |
| 2008 | -- | $155,289 +21.1% |
| 2007 | -- | $128,260 |
| 2006 | $9,068 | $128,260 +6.7% |
| 2005 | -- | $120,206 +7.1% |
| 2004 | $8,092 +11.5% | $112,196 +4.1% |
| 2003 | $7,255 | $107,742 +8.5% |
| 2002 | $7,255 +5.8% | $99,301 +2.9% |
| 2001 | $6,859 +2.9% | $96,502 +5.5% |
| 2000 | $6,667 | $91,471 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 60543
Nearby schools
GreatSchools rating
- 8/10Grande Park Elementary SchoolGrades: K-5Distance: 0.9 mi
- 7/10Murphy Junior High SchoolGrades: 6-8Distance: 0.9 mi
- 9/10Oswego East High SchoolGrades: 9-12Distance: 4.4 mi
Schools provided by the listing agent
- District: 308
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Illinois
- Kendall County
- Oswego
- 60543
- 1542 Plainfield Rd
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