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Ad #7839978
MLS #12644617
Listing photo

Welcome to the historic Gaylord House & Gardens, a truly

1542 Plainfield Rd, Oswego, Illinois, 60543
$1,150,000
5Beds
5Baths
6,050Sqft
5.240Acres

About this property

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.

Property Features

5 Beds
5 Baths
6,050 Sqft
Built in 1865
5.240 Acres
2 Stories
Open, Garage
Siding: Brick
Asphalt Roof
Has Fireplace
Radiant, Steam, Zoned, Natural Gas, Other (Heating), Radiant Floor, Baseboard, Forced Air
$17,190 / yr property tax
Kendall County

Additional Photos

Additional listing photo 1
Additional listing photo 2
Additional listing photo 3
Additional listing photo 4

Contact Information

Robert Grilli

Jameson Real Estate LLC

312-335-3291

Location

Map
Listing Agent: Robert Grilli 312-335-3291
Broker: Jameson Real Estate LLC 312-335-3291 Listing Site
Copyright © 2026 Midwest Real Estate Data, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BarrierFreeHome.com
Printed Jul 24, 2026

Photo Gallery

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$1,150,000

5
Beds
5
Baths
6,050
Sqft

1542 Plainfield Rd, Oswego, Illinois, 60543

By contacting this agent you agree to these Terms and Conditions.
Home Illinois Oswego
Welcome to the historic Gaylord House & Gardens, a truly - photo 1
Welcome to the historic Gaylord House & Gardens, a truly - photo 2
Welcome to the historic Gaylord House & Gardens, a truly - photo 3
Welcome to the historic Gaylord House & Gardens, a truly - photo 4
Welcome to the historic Gaylord House & Gardens, a truly - photo 5
MLS# 12644617
Home For Sale

Welcome to the historic Gaylord House & Gardens, a truly

$1,150,000

1542 Plainfield Rd, Oswego, Illinois, 60543

5
Beds
5
Baths
6,050
Sqft
5.240
Acres
$1,150,000
1542 Plainfield Rd, Oswego, Illinois, 60543
5 Beds
5 Baths
6,050 Sqft
5.240 Acres

Accessibility Features

Accessible Approach with Ramp
Accessible Elevator Installed
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.
53 days
on BarrierFreeHome.com
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Property Details

HOME DETAILS

5 Beds
5 Baths
6,050 Sqft
Built in 1865
5.240 Acres
2 Stories

EXTERIOR

Open, Garage
Siding: Brick
Asphalt Roof

INTERIOR

Has Fireplace
Radiant, Steam, Zoned, Natural Gas, Other (Heating), Radiant Floor, Baseboard, Forced Air

FINANCIAL & COMMUNITY

$17,190 / yr property tax
Kendall County
See More Details

Location

Map
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Ad Statistics

Ad Number
7839978
Viewed
23 times
Listing Status
Active
Added
Jun 01, 2026
Last Refresh
Jul 24, 2026 07:15:10 PM

Listing Information

Data Source
Midwest Real Estate Data, LLC
Source Property ID
12644617
Listing Agent: Robert Grilli 312-335-3291
Broker: Jameson Real Estate LLC 312-335-3291 Listing Site
Copyright © 2026 Midwest Real Estate Data, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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By proceeding, you authorize Dream Home Network Inc., its service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners), its affiliates, and other real estate professionals that may not be associated with Dream Home Network, to contact you using the contact details you provided, via email, phone call, and text (SMS), including using automated dialing technology and prerecorded and artificial voice, for marketing or advertising purposes, including contacting you about your inquiry and other home-related matters. You understand that your consent to the foregoing is not a condition of any purchase. Message and data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what you are looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at csv@dreamhomenetwork.com.
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SERVICES
Buy Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com MountainHomes.com BeachHouse.com GolfHomes.com
SUBSCRIBE
Receive notifications for new listings
Subscribe
Facebook YouTube

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 Wheelchair-accessible Housing & Universal Design Homes at Barrier Free Home
Part of Dream Home Network, Inc.
Last updated on 2026.07.24
Terms & Policy