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$279,000

Step into the timeless charm of this vintage home nestled in the heart of historic Old Town Oswego! Just a short walk to downtown shops, restaurants, parks, and local favorites, this home offers character you simply can't recreate. Original hardwood floors lie beneath the carpet in the living room, dining room, and den, waiting to be brought back to life. The spacious kitchen has been updated with oak cabinetry and flooring while maintaining the home's classic appeal. Featuring 3 bedrooms, 2 full bathrooms, a basement with ample storage, and a detached one-car garage, there's plenty of room to make it your own. Enjoy relaxing on the welcoming screened front porch or entertaining on the rear deck and patio. With solid bones, vintage character, and the opportunity to add your own cosmetic touches over time, this is the perfect home for buyers who appreciate classic craftsmanship and want to build equity while preserving its historic charm.

3 Beds ⋅ 2 Baths ⋅ 12701956 MLS ⋅ ACTIVE Status

Step into the timeless charm of this vintage home nestled in the heart of historic Old Town Oswego! Just a short walk to downtown shops, restaurants, parks, and local favorites, this home offers character you simply can't recreate. Original hardwood floors lie beneath the carpet in the living room, dining room, and den, waiting to be brought back to life. The spacious kitchen has been updated with oak cabinetry and flooring while maintaining the home's classic appeal. Featuring 3 bedrooms, 2 full bathrooms, a basement with ample storage, and a detached one-car garage, there's plenty of room to make it your own. Enjoy relaxing on the welcoming screened front porch or entertaining on the rear deck and patio. With solid bones, vintage character, and the opportunity to add your own cosmetic touches over time, this is the perfect home for buyers who appreciate classic craftsmanship and want to build equity while preserving its historic charm.

39 Park Street, Oswego

$1,000,000

Timeless farmhouse charm meets today's modern luxury on 2.27 picturesque acres! Completely transformed through an extensive whole-house renovation, this one-of-a-kind property offers the perfect blend of historic character, thoughtful craftsmanship, and incredible versatility. The heart of the home is a stunning custom kitchen (2022) featuring a massive quartz island, farmhouse sink, custom staggered cabinetry, premium Wolf range, double ovens, stainless steel appliances, and abundant storage designed for everyday living and effortless entertaining. Rich hardwood flooring, fresh paint, updated trim, custom two-panel doors, and soaring 10-foot ceilings throughout much of the main level create a warm, inviting atmosphere. Flexible living spaces provide endless possibilities, including formal living and dining rooms, a private home office, a cozy family room with fireplace, and a light-filled sunroom overlooking the property. The main level also includes beautifully remodeled laundry and powder rooms. Upstairs, the private primary suite offers a spacious walk-in closet and remodeled en-suite bath, while three additional bedrooms share a beautifully renovated hall bath complete with dual vanities, heated floors, illuminated mirrors, an oversized 48-inch shower with built-in seat, and a luxurious soaking tub. Major improvements provide peace of mind, including updated electrical and plumbing, new well (2017), tankless water heater with water filtration system, roof on both the home and barn (2018), waterproofed basement with French drain system, and much more. Outdoor living is equally impressive with a custom covered front porch, expansive brick paver patio, updated deck, mature trees, and beautifully maintained grounds. The approximately 1,400-square-foot two-story barn is an incredible bonus, offering exposed beams, electricity, gas line, water hookup, high-efficiency furnace, lift, and multiple finished and unfinished spaces ideal for a workshop, studio, hobby farm, collector cars, home business, or future expansion. An additional 20x30 garden shed with electricity provides even more flexibility. Located just minutes from the Route 34 shopping corridor, Fox Bend Golf Course, and the restaurants and charm of Downtown Oswego, this exceptional property offers the rare opportunity to enjoy peaceful country living without sacrificing everyday convenience. If you've been dreaming of a beautifully restored farmhouse with room to spread out, entertain, pursue your hobbies, or simply enjoy life on acreage, this is one you won't want to miss.

4 Beds ⋅ 3 Baths ⋅ 12699328 MLS ⋅ ACTIVE Status

Timeless farmhouse charm meets today's modern luxury on 2.27 picturesque acres! Completely transformed through an extensive whole-house renovation, this one-of-a-kind property offers the perfect blend of historic character, thoughtful craftsmanship, and incredible versatility. The heart of the home is a stunning custom kitchen (2022) featuring a massive quartz island, farmhouse sink, custom staggered cabinetry, premium Wolf range, double ovens, stainless steel appliances, and abundant storage designed for everyday living and effortless entertaining. Rich hardwood flooring, fresh paint, updated trim, custom two-panel doors, and soaring 10-foot ceilings throughout much of the main level create a warm, inviting atmosphere. Flexible living spaces provide endless possibilities, including formal living and dining rooms, a private home office, a cozy family room with fireplace, and a light-filled sunroom overlooking the property. The main level also includes beautifully remodeled laundry and powder rooms. Upstairs, the private primary suite offers a spacious walk-in closet and remodeled en-suite bath, while three additional bedrooms share a beautifully renovated hall bath complete with dual vanities, heated floors, illuminated mirrors, an oversized 48-inch shower with built-in seat, and a luxurious soaking tub. Major improvements provide peace of mind, including updated electrical and plumbing, new well (2017), tankless water heater with water filtration system, roof on both the home and barn (2018), waterproofed basement with French drain system, and much more. Outdoor living is equally impressive with a custom covered front porch, expansive brick paver patio, updated deck, mature trees, and beautifully maintained grounds. The approximately 1,400-square-foot two-story barn is an incredible bonus, offering exposed beams, electricity, gas line, water hookup, high-efficiency furnace, lift, and multiple finished and unfinished spaces ideal for a workshop, studio, hobby farm, collector cars, home business, or future expansion. An additional 20x30 garden shed with electricity provides even more flexibility. Located just minutes from the Route 34 shopping corridor, Fox Bend Golf Course, and the restaurants and charm of Downtown Oswego, this exceptional property offers the rare opportunity to enjoy peaceful country living without sacrificing everyday convenience. If you've been dreaming of a beautifully restored farmhouse with room to spread out, entertain, pursue your hobbies, or simply enjoy life on acreage, this is one you won't want to miss.

3614 Wolf Road, Oswego

$1,100,000

Welcome to Oakberry Farm, a rare 8.5-acre private country estate tucked among mature hardwoods and rolling woodlands just minutes from Oswego, Plainfield, and Naperville. Rich in history, character, and natural beauty, this remarkable property offers two homes, multiple outbuildings, private walking trails, and a setting that feels worlds away from the everyday.~~~The centerpiece of the estate is a beautifully renovated Victorian farmhouse featuring 5 bedrooms, 2 bathrooms, and 3,038 square feet. Timeless architectural details, soaring ceilings, original character, and extensive updates combine to create a home that is both elegant and inviting.~~~A separate Cottage offers an additional 1,662 square feet with 2 bedrooms and 1 bathroom, creating exceptional flexibility for multi-generational living, guests, a private home office, caretaker quarters, or potential rental opportunities.~~~The property also includes a heated and insulated Art Studio with concrete floors and electricity, detached 3-car garage, greenhouse, garden shed, and two historic barn structures that contribute to the property's unique charm and story. A picturesque two-story timber-frame barn stands as a reminder of the property's agricultural roots and creates a stunning focal point within the landscape, while a charming former stable building, affectionately known as "The Museum," further enhances the estate's historic appeal.~~~Towering oak, walnut, maple, and other mature hardwood trees surround the property, while private trails wind through the woods creating an extraordinary backdrop for daily life. Agricultural zoning offers flexibility for future use while preserving the property's rural character.~~~Properties of this caliber and versatility rarely become available. Whether you're seeking a private retreat, multi-generational estate, or simply a one-of-a-kind property with unmatched character and setting, Oakberry Farm presents an exceptional opportunity.

7 Beds ⋅ 3 Baths ⋅ 12682754 MLS ⋅ ACTIVE Status

Welcome to Oakberry Farm, a rare 8.5-acre private country estate tucked among mature hardwoods and rolling woodlands just minutes from Oswego, Plainfield, and Naperville. Rich in history, character, and natural beauty, this remarkable property offers two homes, multiple outbuildings, private walking trails, and a setting that feels worlds away from the everyday.~~~The centerpiece of the estate is a beautifully renovated Victorian farmhouse featuring 5 bedrooms, 2 bathrooms, and 3,038 square feet. Timeless architectural details, soaring ceilings, original character, and extensive updates combine to create a home that is both elegant and inviting.~~~A separate Cottage offers an additional 1,662 square feet with 2 bedrooms and 1 bathroom, creating exceptional flexibility for multi-generational living, guests, a private home office, caretaker quarters, or potential rental opportunities.~~~The property also includes a heated and insulated Art Studio with concrete floors and electricity, detached 3-car garage, greenhouse, garden shed, and two historic barn structures that contribute to the property's unique charm and story. A picturesque two-story timber-frame barn stands as a reminder of the property's agricultural roots and creates a stunning focal point within the landscape, while a charming former stable building, affectionately known as "The Museum," further enhances the estate's historic appeal.~~~Towering oak, walnut, maple, and other mature hardwood trees surround the property, while private trails wind through the woods creating an extraordinary backdrop for daily life. Agricultural zoning offers flexibility for future use while preserving the property's rural character.~~~Properties of this caliber and versatility rarely become available. Whether you're seeking a private retreat, multi-generational estate, or simply a one-of-a-kind property with unmatched character and setting, Oakberry Farm presents an exceptional opportunity.

7479 Grove Road, Oswego

$399,000

Discover a rare Fox Riverfront home for sale in Oswego, Illinois! Situated on a 1.05-acre lot directly across from the Fox River and Veterans Serenity Park, this property offers stunning year-round water views and immediate access to the Fox River Trail right outside your front door. Perfect for biking, jogging, or scenic walks, this location combines outdoor recreation with small-town charm. This 2-bedroom, 1-bath home offers 1,200 sq. ft. of living space filled with natural light. The inviting living room features warm wood-accent walls, a bay window overlooking the park and river, and an open layout that flows into the dining space-ideal for entertaining. The bright kitchen has vaulted ceilings, tile flooring, and plenty of potential for customization. A full basement provides additional storage or expansion space. Car lovers, mechanics, and hobbyists will appreciate the oversized 3-car garage with an extra-high overhead door, perfect for storing boats, RVs, and other outdoor toys. A storage shed is also included. The spacious deck is ideal for morning coffee, weekend BBQs, and watching the sunset over the water. Located just minutes from downtown Oswego's shops, restaurants, and community events, this property offers both tranquility and convenience. Whether you're seeking a single-family home with river views, a vacation home in Oswego, or a prime redevelopment lot in Kendall County, 34 N Adams St is a one-of-a-kind opportunity.

2 Beds ⋅ 1 Baths ⋅ 12669255 MLS ⋅ ACTIVE Status

Discover a rare Fox Riverfront home for sale in Oswego, Illinois! Situated on a 1.05-acre lot directly across from the Fox River and Veterans Serenity Park, this property offers stunning year-round water views and immediate access to the Fox River Trail right outside your front door. Perfect for biking, jogging, or scenic walks, this location combines outdoor recreation with small-town charm. This 2-bedroom, 1-bath home offers 1,200 sq. ft. of living space filled with natural light. The inviting living room features warm wood-accent walls, a bay window overlooking the park and river, and an open layout that flows into the dining space-ideal for entertaining. The bright kitchen has vaulted ceilings, tile flooring, and plenty of potential for customization. A full basement provides additional storage or expansion space. Car lovers, mechanics, and hobbyists will appreciate the oversized 3-car garage with an extra-high overhead door, perfect for storing boats, RVs, and other outdoor toys. A storage shed is also included. The spacious deck is ideal for morning coffee, weekend BBQs, and watching the sunset over the water. Located just minutes from downtown Oswego's shops, restaurants, and community events, this property offers both tranquility and convenience. Whether you're seeking a single-family home with river views, a vacation home in Oswego, or a prime redevelopment lot in Kendall County, 34 N Adams St is a one-of-a-kind opportunity.

34 N Adams Street, Oswego

$1,150,000

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.

5 Beds ⋅ 5 Baths ⋅ 12644617 MLS ⋅ ACTIVE Status

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.

1542 Plainfield Road, Oswego