1542 Plainfield Rd

Oswego, IL 60543

$1,150,000
Price
5
Beds
6,050 Sq. Ft.
$190 / Sq. Ft.
6,050
Sq. Ft.
$190
per Sq. Ft.
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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....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.
  1. Listed by Robert Grilli • Jameson Sotheby's Intl Realty
    P: (708)-337-2385 realty.bobbyg@gmail.com; realty.bobbyg@gmail.com
  2. Listed by Alexandra Morgan • Jameson Sotheby's Intl Realty
    P: (203)-721-2238 C: (203)-721-2238 amorgan@jamesonsir.com

Property Details for 1542 Plainfield Road

Area
Oswego
Township
Oswego
Ownership
Fee Simple
Num Of Garage Spaces
2.5
Num Of Parking Spaces
2.5
Parking Included in Price
Yes
Air Conditioning Type
Central Air, Zoned
Num of Interior Fireplaces
2
LISTING UPDATED: 06/01/2026 08:30 PM

Property Details for 1542 Plainfield Road

StatusActive
MLS #12644617
Days on Market21
Taxes$17,190 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeDetached Single / 2 Stories
Year Built1865
Lot Size5.24 AC / 228,254 SF
CountyKendall County
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Location

Listing Courtesy of Jameson Sotheby's Intl Realty
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Building Information for 1542 Plainfield Road

Stories-Year Built1865Building Size-Lot Size5.24 AC / 228,254 SF

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$7,163 per month

30 year fixed, 6.36% Interest

Principal and Interest

$5,731

Property Taxes

$1,433

HOA Dues

$0

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Property Information for 1542 Plainfield Road

General Information
School Information
  • Elementary School District: 308
  • High School District: 308
  • Middle Or Junior School District: 308
Addtl Parking Information
  • Parking Details: Asphalt, Other, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location and General Information
  • Front Exposure: North
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee: No
  • Master Association Fee Frequency: Not Required
  • Additional Parcels: No
Property Information
Interior Features
  • Interior Property 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
  • Num Of Rooms: 12
  • Bedrooms Total: 5
  • Bedrooms (Below Grade): 0
  • Community Features: Gated, Street Paved
  • Attic: Finished
  • Bath Amenities: Whirlpool,Steam Shower,Double Sink,Soaking Tub
  • Fireplace Features: Wood Burning, Gas Starter
  • Basement Type: Finished, Full
  • Bedrooms Possible: 5
  • Air Conditioning: Central Air, Zoned
  • Electric: Circuit Breakers
  • Flooring: Hardwood
  • Basement Sq Ft: 1561
  • Dining Room: Separate
  • Basement Bathrooms: Yes
  • Fireplace Location: Family Room,Living Room
  • Room Type: Bedroom 5, Screened Porch, Attic, Exercise Room, Recreation Room
  • Num of Baths: 4.1
Exterior Features
  • Fencing: Fenced
  • Patio And Porch Features: Deck, Screened
  • Type: 2 Stories
Utilities / Equipment
  • Sewer: Septic Tank
  • Water: Well
  • Appliances: Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Water Softener Owned
  • Other Equipment: Water-Softener Owned, CO Detectors, Ceiling Fan(s), Sump Pump
Property/Lot Information
  • Exterior Property Features: Hot Tub
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: No
  • Built Before 1978: Yes
  • Age: 100+ Years
  • Type Detached: 2 Stories
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 1561
  • Total Finished and Unfin Sq Ft: 1561
  • Lot Description: Landscaped Professionally, Mature Trees, Pasture
  • Lot Size: 5.0-5.99 Acres
  • Lot Dimensions: 208817
  • Other Structures: Workshop, Barn(s), Outbuilding, Poultry Coop, Shed(s)
  • Waterfront: No
  • Disability Access and/or Equipped: Yes
  • Exterior Building Type: Brick
  • Construction: Brick
  • Roof Type: Asphalt
  • Foundation Details: Block
  • General Information: School Bus Service
  • 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)
  • Below Grade Finished Area: 1561.0
  • Living Area Source: Plans
  • Assessor Square Footage: 4215
Property and Assessments
  • Public Document Count: 3
  • Document Date: 2026-05-18T21:47:49
  • Photos Count: 64
  • Rural: N
  • OpenHouse Count: 0
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Room Information
Master Bedroom Information
  • Master Bedroom Level: Second
  • Room Type: Master Bedroom
  • Master Bedroom Bath: Full
  • Master Bedroom Dimensions: 17X20
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 16X16
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 12X13
Bedroom #4 Information
  • 4th Bedroom Level: Second
  • Room Type: Bedroom 4
  • Bedroom #4 Room Dimensions: 12X14
Bedroom #5 Information
  • 5th Bedroom Level: Main
  • Room Type: Bedroom 5
  • Bedroom #5 Room Dimensions: 16X16
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 24X14
Family Room Information
  • Family Room Level: Main
  • RoomType_FR: Family Room
  • Family Room Dimensions: 27X25
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 13X17
Laundry Information
  • Laundry Level: Basement
  • Room Type: Laundry
  • Laundry Dimensions: 7X10
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 18X20
Exercise Room Information
  • Room Level: Basement
  • Room Type: Exercise Room
  • Dimensions: 18X23
Recreation Rm Information
  • Room Level: Basement
  • Room Type: Recreation Rm
  • Dimensions: 21X19
Attic Room Information
  • Room Level: Third
  • Room Type: Attic
  • Dimensions: 35X34
Screened Porch Information
  • Room Level: Main
  • Room Type: Screened Porch
  • Dimensions: 29X12

Property History for 1542 Plainfield Road

DateEvent & SourcePriceAppreciation
May 20, 2026

Listed (Active)

MRED #12644617

$1,150,000—
Apr 24, 2025

Sold

MRED #12308894

$867,500—
Apr 16, 2025

Sold (Public Record)

Public Record #1557203949

$867,500

+7.8% / yr

DateEvent & SourcePrice
05/20/2026

Listed (Active)

MRED #12644617

$1,150,000
04/24/2025

Sold

MRED #12308894

$867,500
04/16/2025

Sold (Public Record)

Public Record #1557203949

$867,500

+7.8% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 1542 Plainfield Road

Taxable ValueLand$49,973Additions$223,562Total$273,535
Tax Record2025$17,191 ($1,433 / month)
Home Facts
Beds4Total Finished SqFt4,215 SqFtAbove Grade Finished SqFt4,215 SqFtStories2Lot Size209,001 SqFtStyleSingle Family ResidenceYear Built1865ZoningR-3 SUCountyKENDALLAPN03-35-377-003

Schools near 1542 Plainfield Road

This home is within Oswego Community Unit School District 308.
Rating
School
Type
Grades
Distance
Hunt Club Elementary School
Public - K to 5
Murphy Junior High School
Public - 6 to 8
Oswego East High School
Public - 9 to 12
Goal - Granting Opportunities For Alternative Livi
Public - 6 to 12
Rating
School
Distance
Hunt Club Elementary School
PublicK to 5

Murphy Junior High School
Public6 to 8

Oswego East High School
Public9 to 12

Goal - Granting Opportunities For Alternative Livi
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1542 Plainfield Road, Oswego, IL 60543

1542 Plainfield Road is a single family home for sale in Oswego, IL 60543. This property was listed for sale on May 20, 2026 by Jameson Sotheby's Intl Realty, it's currently listed at $1,150,000. It has been on the market for a total of 21 days and was last sold on April 24, 2025. This listing's school district is Oswego Community Unit School District 308. Nearby schools include Hunt Club Elementary School, Murphy Junior High School and Oswego East High School. 1542 Plainfield Road is a 5-bed, 5-bath, 6,050 sqft single family home built in 1865.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Jameson Sotheby's Intl Realty

Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 06/01/2026 08:30 PM. 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.