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Experience a lifestyle rarely found in today's market, where luxury, privacy, and everyday comfort come together on approximately 12 breathtaking acres in Woodstock. This custom-built French Provincial estate offers more than 7,200 square feet of thoughtfully designed living space, creating the perfect balance of grand-scale entertaining and relaxed daily living. *** At the heart of the home, the beautifully updated custom kitchen is designed for gathering. Featuring premium Thermador and Viking appliances, handcrafted cabinetry, and an oversized island with a copper countertop and prep sink, it provides both exceptional functionality for serious cooking and an inviting space where family and friends naturally come together. *** The dramatic great room serves as a stunning centerpiece, with soaring vaulted ceilings, rich hardwood flooring, a floor-to-ceiling stone fireplace, and walls of windows that fill the home with natural light while showcasing picturesque views of the surrounding grounds. Whether enjoying a quiet evening by the fire or hosting holiday celebrations, the space offers warmth, comfort, and an unforgettable setting. *** A first-floor primary suite provides the convenience and privacy of main-level living. Designed as a true retreat, it features dual walk-in closets, heated bathroom floors, a Jacuzzi tub, and an oversized walk-in shower, creating a spa-like experience that makes every day feel like a getaway. *** Four additional bedrooms offer flexibility for family members, guests, home offices, or multi-generational living. The finished walkout lower level expands the home's versatility with a recreation area, fitness room, full bath, abundant storage, and direct access to the lower-level garage, creating the perfect space for entertaining, hobbies, wellness, or extended guest accommodations. *** Step outside and discover a property designed to embrace outdoor living. The expansive wraparound deck with its outdoor fireplace invites year-round enjoyment, from morning coffee overlooking the grounds to relaxing evenings beneath the stars. A walkout patio, tranquil waterfall feature, winding driveway, and professionally landscaped surroundings create a peaceful, resort-like atmosphere. *** The approximately 12-acre setting offers endless opportunities to enjoy nature and recreation right outside your door. Walking paths encourage daily exploration, while the outdoor shed with loft, custom chicken and duck coops, and built-in dog kennels provide unique opportunities for hobby farming, animal care, and an active outdoor lifestyle. The acreage delivers a level of freedom, space, and privacy that is increasingly difficult to find. *** Modern updates further enhance peace of mind and convenience, including a custom front entry door, fresh interior paint, luxury vinyl plank flooring, energy-efficient LED lighting, a whole-house security system with cameras, and a newer water heater, allowing you to move in and immediately enjoy all the benefits of estate living. *** Despite its private country setting, the property remains conveniently close to historic downtown Woodstock, where charming shops, dining, entertainment, and community events are just minutes away. You'll enjoy the serenity of rural living without sacrificing everyday conveniences. *** This remarkable estate offers far more than a home. It offers a lifestyle defined by privacy, flexibility, recreation, and luxury. From the grand architecture and one-of-a-kind interior spaces to the expansive acreage, outdoor amenities, and impressive 8-car garage capacity, this extraordinary Woodstock property delivers the rare opportunity to live, entertain, and unwind in your own private countryside retreat. ** Buyer Opportunity: For qualified buyers, seller is offering either a 2-1 temporary interest rate buydown or a permanent buydown, subject to lender approval and loan program requirements, providing the potential for greater affordability and lower monthly payments.

5 Beds ⋅ 5 Baths ⋅ 12795954 MLS ⋅ NEW Status

Experience a lifestyle rarely found in today's market, where luxury, privacy, and everyday comfort come together on approximately 12 breathtaking acres in Woodstock. This custom-built French Provincial estate offers more than 7,200 square feet of thoughtfully designed living space, creating the perfect balance of grand-scale entertaining and relaxed daily living. *** At the heart of the home, the beautifully updated custom kitchen is designed for gathering. Featuring premium Thermador and Viking appliances, handcrafted cabinetry, and an oversized island with a copper countertop and prep sink, it provides both exceptional functionality for serious cooking and an inviting space where family and friends naturally come together. *** The dramatic great room serves as a stunning centerpiece, with soaring vaulted ceilings, rich hardwood flooring, a floor-to-ceiling stone fireplace, and walls of windows that fill the home with natural light while showcasing picturesque views of the surrounding grounds. Whether enjoying a quiet evening by the fire or hosting holiday celebrations, the space offers warmth, comfort, and an unforgettable setting. *** A first-floor primary suite provides the convenience and privacy of main-level living. Designed as a true retreat, it features dual walk-in closets, heated bathroom floors, a Jacuzzi tub, and an oversized walk-in shower, creating a spa-like experience that makes every day feel like a getaway. *** Four additional bedrooms offer flexibility for family members, guests, home offices, or multi-generational living. The finished walkout lower level expands the home's versatility with a recreation area, fitness room, full bath, abundant storage, and direct access to the lower-level garage, creating the perfect space for entertaining, hobbies, wellness, or extended guest accommodations. *** Step outside and discover a property designed to embrace outdoor living. The expansive wraparound deck with its outdoor fireplace invites year-round enjoyment, from morning coffee overlooking the grounds to relaxing evenings beneath the stars. A walkout patio, tranquil waterfall feature, winding driveway, and professionally landscaped surroundings create a peaceful, resort-like atmosphere. *** The approximately 12-acre setting offers endless opportunities to enjoy nature and recreation right outside your door. Walking paths encourage daily exploration, while the outdoor shed with loft, custom chicken and duck coops, and built-in dog kennels provide unique opportunities for hobby farming, animal care, and an active outdoor lifestyle. The acreage delivers a level of freedom, space, and privacy that is increasingly difficult to find. *** Modern updates further enhance peace of mind and convenience, including a custom front entry door, fresh interior paint, luxury vinyl plank flooring, energy-efficient LED lighting, a whole-house security system with cameras, and a newer water heater, allowing you to move in and immediately enjoy all the benefits of estate living. *** Despite its private country setting, the property remains conveniently close to historic downtown Woodstock, where charming shops, dining, entertainment, and community events are just minutes away. You'll enjoy the serenity of rural living without sacrificing everyday conveniences. *** This remarkable estate offers far more than a home. It offers a lifestyle defined by privacy, flexibility, recreation, and luxury. From the grand architecture and one-of-a-kind interior spaces to the expansive acreage, outdoor amenities, and impressive 8-car garage capacity, this extraordinary Woodstock property delivers the rare opportunity to live, entertain, and unwind in your own private countryside retreat. ** Buyer Opportunity: For qualified buyers, seller is offering either a 2-1 temporary interest rate buydown or a permanent buydown, subject to lender approval and loan program requirements, providing the potential for greater affordability and lower monthly payments.

15309 Kishwaukee Valley Road, Woodstock

$249,000

Charming turn-of-the-century home built in 1900, ideally located just .5 miles from the historic Woodstock Square and .4 miles from the Metra station. This 2-bedroom, 1.5-bath home features a spacious living room and large dining room, offering plenty of room to entertain. An alcove off the living room is perfect for a home office, reading nook, or creative space. Flexible rooms and versatile spaces allow you to tailor the home to your lifestyle and needs. Original hardwood floors, currently painted, offer the potential to restore their natural beauty and add to the home's historic charm. Storage is plentiful throughout, including a walk-in attic tucked behind a secret door in the upstairs bathroom. Enjoy enclosed front and back porches, a fabulous deck with pergola overlooking the backyard and mature trees, and a detached 1.5-car garage. Conveniently located near Woodstock's unique shops, restaurants, local events, and commuter rail, this home offers character, possibilities, and a convenient location close to downtown. Sold as is.

2 Beds ⋅ 2 Baths ⋅ 12792996 MLS ⋅ ACTIVE Status

Charming turn-of-the-century home built in 1900, ideally located just .5 miles from the historic Woodstock Square and .4 miles from the Metra station. This 2-bedroom, 1.5-bath home features a spacious living room and large dining room, offering plenty of room to entertain. An alcove off the living room is perfect for a home office, reading nook, or creative space. Flexible rooms and versatile spaces allow you to tailor the home to your lifestyle and needs. Original hardwood floors, currently painted, offer the potential to restore their natural beauty and add to the home's historic charm. Storage is plentiful throughout, including a walk-in attic tucked behind a secret door in the upstairs bathroom. Enjoy enclosed front and back porches, a fabulous deck with pergola overlooking the backyard and mature trees, and a detached 1.5-car garage. Conveniently located near Woodstock's unique shops, restaurants, local events, and commuter rail, this home offers character, possibilities, and a convenient location close to downtown. Sold as is.

629 N Madison Street, Woodstock

$950,000

You won't find another property quite like this. Start with a 100-year-old farmhouse, then thoughtfully blend its character with a 21st-century expansion and renovation. Add an in-ground pool, a two-story barn with a party room, and nearly an acre of beautifully landscaped grounds-all conveniently located in town, close to schools and the historic Woodstock Square. The home offers approximately 3,700 square feet of living space, with generously sized rooms throughout. The spacious living room is anchored by a cozy fireplace, while the large dining room is ready for everything from family dinners to the grandest of feasts. The kitchen is designed for gathering, with a substantial island and breakfast bar. The family room provides even more space for entertaining or relaxing and features a second fireplace. Upstairs, you'll find four generously sized bedrooms. The primary suite features a vaulted ceiling, walk-in closet, and private bath. The second floor also includes a convenient laundry room and a screened porch-perfect for relaxing on warm summer evenings. The finished basement adds a game room for even more living and entertaining space. The home features zoned heating and air conditioning and Andersen windows. The roof is just three years old, and the exterior was painted last year. But that's only the beginning. Outside, the 20' x 40' saltwater pool is an incredible centerpiece, featuring an 8.5-foot depth, diving board, slide, and spacious patio surround. The farm's original chicken coop has been transformed into a charming pool house. The two-story barn adds even more versatility, with newer siding and roof, a three-car garage on the ground level, and a fun, inviting party room upstairs-an ideal space for entertaining friends and family. The beautifully landscaped grounds have been featured in several local garden walks, adding to the property's unique charm and appeal. You are only steps from Woodstock's biggest park with walking trails, pickle ball courts, sledding hill and more. This description only scratches the surface. From its historic roots and thoughtful updates to the pool, barn, expansive grounds, and exceptional entertaining spaces, this is a truly one-of-a-kind property you'll want to call home.

4 Beds ⋅ 5 Baths ⋅ 12714786 MLS ⋅ ACTIVE Status

You won't find another property quite like this. Start with a 100-year-old farmhouse, then thoughtfully blend its character with a 21st-century expansion and renovation. Add an in-ground pool, a two-story barn with a party room, and nearly an acre of beautifully landscaped grounds-all conveniently located in town, close to schools and the historic Woodstock Square. The home offers approximately 3,700 square feet of living space, with generously sized rooms throughout. The spacious living room is anchored by a cozy fireplace, while the large dining room is ready for everything from family dinners to the grandest of feasts. The kitchen is designed for gathering, with a substantial island and breakfast bar. The family room provides even more space for entertaining or relaxing and features a second fireplace. Upstairs, you'll find four generously sized bedrooms. The primary suite features a vaulted ceiling, walk-in closet, and private bath. The second floor also includes a convenient laundry room and a screened porch-perfect for relaxing on warm summer evenings. The finished basement adds a game room for even more living and entertaining space. The home features zoned heating and air conditioning and Andersen windows. The roof is just three years old, and the exterior was painted last year. But that's only the beginning. Outside, the 20' x 40' saltwater pool is an incredible centerpiece, featuring an 8.5-foot depth, diving board, slide, and spacious patio surround. The farm's original chicken coop has been transformed into a charming pool house. The two-story barn adds even more versatility, with newer siding and roof, a three-car garage on the ground level, and a fun, inviting party room upstairs-an ideal space for entertaining friends and family. The beautifully landscaped grounds have been featured in several local garden walks, adding to the property's unique charm and appeal. You are only steps from Woodstock's biggest park with walking trails, pickle ball courts, sledding hill and more. This description only scratches the surface. From its historic roots and thoughtful updates to the pool, barn, expansive grounds, and exceptional entertaining spaces, this is a truly one-of-a-kind property you'll want to call home.

688 W South Street, Woodstock

$74,900

BUILD THE HOME OF YOUR DREAMS. 3.297 ACRES MINUTES FROM DOWNTOWN WOODSTOCK AND THE WISCONSIN BORDER. THE BACK 1.297 ACRES IS IN A FLOOD PLAIN HOWEVER PER MCHENRY COUNTY ZONING/WETLANDS DIVISION THAT PORTION (BEYOND THE BERM) IS LOCATED IN A 100 YEAR FLOOD ZONE WITH THE CHANCE OF FLOODING AT ONLY ONE PER CENT NO FLOOD INSURANCE IS REQUIRED TO BUILD A HOME ON THE PROPERTY AND WITH APPROVAL ACREAGE BEYOND THE BERM ALLOWS FOR A STRUCTURE SUCH AS A POLE BARN. HORSES ALLOWED. LOT 15 ON THE LEFT. SURVEY UNDER ADDITIONAL INFORMATION AS WELL AS SOIL TEST FROM 2019 AND AN UPDATED SOIL TEST FROM 2025.....READY TO BE BUILT ON

12768393 MLS ⋅ ACTIVE Status

BUILD THE HOME OF YOUR DREAMS. 3.297 ACRES MINUTES FROM DOWNTOWN WOODSTOCK AND THE WISCONSIN BORDER. THE BACK 1.297 ACRES IS IN A FLOOD PLAIN HOWEVER PER MCHENRY COUNTY ZONING/WETLANDS DIVISION THAT PORTION (BEYOND THE BERM) IS LOCATED IN A 100 YEAR FLOOD ZONE WITH THE CHANCE OF FLOODING AT ONLY ONE PER CENT NO FLOOD INSURANCE IS REQUIRED TO BUILD A HOME ON THE PROPERTY AND WITH APPROVAL ACREAGE BEYOND THE BERM ALLOWS FOR A STRUCTURE SUCH AS A POLE BARN. HORSES ALLOWED. LOT 15 ON THE LEFT. SURVEY UNDER ADDITIONAL INFORMATION AS WELL AS SOIL TEST FROM 2019 AND AN UPDATED SOIL TEST FROM 2025.....READY TO BE BUILT ON

1408 Savannah Lane, Woodstock

$279,000

Estate sale being sold As-Is but house is in very good condition

3 Beds ⋅ 1 Baths ⋅ 12750605 MLS ⋅ PRICE CHANGE Status

Estate sale being sold As-Is but house is in very good condition

139 W Melody Lane, Woodstock

$150,000

Build Your Dream Home! Fantastic opportunity to own 5.43 acres of vacant land offering plenty of space and endless possibilities. Enjoy the privacy and peaceful surroundings of a spacious homesite. With over five acres, there is ample room to create the property you've been envisioning-whether that includes a custom home, expansive yard, outdoor entertaining areas, or additional space to enjoy. A great opportunity for anyone looking for acreage and the freedom to make it their own. Bring your plans and imagine the possibilities!

12741697 MLS ⋅ ACTIVE Status

Build Your Dream Home! Fantastic opportunity to own 5.43 acres of vacant land offering plenty of space and endless possibilities. Enjoy the privacy and peaceful surroundings of a spacious homesite. With over five acres, there is ample room to create the property you've been envisioning-whether that includes a custom home, expansive yard, outdoor entertaining areas, or additional space to enjoy. A great opportunity for anyone looking for acreage and the freedom to make it their own. Bring your plans and imagine the possibilities!

14411 Windsor Court, Woodstock

$239,900

Welcome to easy living in Prairie Pointe! This charming Aster model end-unit townhome offers over 1,650 square feet of finished living space, including the beautifully finished basement. Unit offers 2 bedrooms, 2.1 bathrooms, a private entrance, and the perfect blend of comfort, convenience, and low-maintenance living. Start your day sitting on the welcoming front porch, enjoying the fresh air and sipping your morning coffee, or unwind in the evening while taking in the peaceful neighborhood surroundings. Step inside and you'll love the inviting open-concept floor plan, designed to keep everyone connected whether you're hosting holiday celebrations, game-day gatherings, or a cozy night in. The spacious kitchen is ready for your favorite recipes with a pantry closet, abundant 42" cabinet storage, generous countertop space, and a breakfast bar where family and friends can pull up a seat and chat while meals are prepared. Upstairs, the oversized primary bedroom provides a peaceful retreat with enough room to add a comfy chair and create your own private reading nook or home office area. The spacious second bedroom and well-appointed shared full bathroom round out the sleeping quarters, offering comfortable accommodations for family members, guests, or flexible use as a hobby room or workspace. Need extra space? The finished basement with a full bathroom opens the door to endless possibilities. Create the ultimate recreation room, game room, playroom, home office, fitness area, or guest space. Whatever your lifestyle needs, this flexible lower level is ready to adapt. The attached one-car garage not only provides additional storage but also offers the convenience of protected access during inclement weather, with an easy path to the kitchen that makes unloading groceries simple and efficient. Best of all, the HOA handles exterior maintenance, lawn care, and snow removal, so weekends can be spent enjoying life instead of tackling chores. Enjoy being just minutes from some of Woodstock's most popular destinations. Spend weekends exploring Emricson Park, featuring walking trails, playgrounds, sports courts, disc golf, ponds, picnic areas, and the Woodstock Water Works aquatic center. Take a short drive to the Historic Woodstock Square, famous as the filming location for Groundhog Day. The Square is filled with charming boutiques, local restaurants, cafes, seasonal festivals, farmers markets, and community events throughout the year. Enjoy live entertainment and cultural events at the beautifully restored Woodstock Opera House, one of the area's most treasured landmarks, or explore the nearby Old Courthouse Center and other historic attractions. Move in, relax, and start enjoying the carefree lifestyle you've been looking for in this wonderful Prairie Pointe townhome!

2 Beds ⋅ 3 Baths ⋅ 12729145 MLS ⋅ ACTIVE Status ⋅ Prairie Pointe BLDG.

Welcome to easy living in Prairie Pointe! This charming Aster model end-unit townhome offers over 1,650 square feet of finished living space, including the beautifully finished basement. Unit offers 2 bedrooms, 2.1 bathrooms, a private entrance, and the perfect blend of comfort, convenience, and low-maintenance living. Start your day sitting on the welcoming front porch, enjoying the fresh air and sipping your morning coffee, or unwind in the evening while taking in the peaceful neighborhood surroundings. Step inside and you'll love the inviting open-concept floor plan, designed to keep everyone connected whether you're hosting holiday celebrations, game-day gatherings, or a cozy night in. The spacious kitchen is ready for your favorite recipes with a pantry closet, abundant 42" cabinet storage, generous countertop space, and a breakfast bar where family and friends can pull up a seat and chat while meals are prepared. Upstairs, the oversized primary bedroom provides a peaceful retreat with enough room to add a comfy chair and create your own private reading nook or home office area. The spacious second bedroom and well-appointed shared full bathroom round out the sleeping quarters, offering comfortable accommodations for family members, guests, or flexible use as a hobby room or workspace. Need extra space? The finished basement with a full bathroom opens the door to endless possibilities. Create the ultimate recreation room, game room, playroom, home office, fitness area, or guest space. Whatever your lifestyle needs, this flexible lower level is ready to adapt. The attached one-car garage not only provides additional storage but also offers the convenience of protected access during inclement weather, with an easy path to the kitchen that makes unloading groceries simple and efficient. Best of all, the HOA handles exterior maintenance, lawn care, and snow removal, so weekends can be spent enjoying life instead of tackling chores. Enjoy being just minutes from some of Woodstock's most popular destinations. Spend weekends exploring Emricson Park, featuring walking trails, playgrounds, sports courts, disc golf, ponds, picnic areas, and the Woodstock Water Works aquatic center. Take a short drive to the Historic Woodstock Square, famous as the filming location for Groundhog Day. The Square is filled with charming boutiques, local restaurants, cafes, seasonal festivals, farmers markets, and community events throughout the year. Enjoy live entertainment and cultural events at the beautifully restored Woodstock Opera House, one of the area's most treasured landmarks, or explore the nearby Old Courthouse Center and other historic attractions. Move in, relax, and start enjoying the carefree lifestyle you've been looking for in this wonderful Prairie Pointe townhome!

446 Borden Street Unit #446, Woodstock

$70,000

Build your dream home on this tree lined lot at this premium location! 2+ Acre Cul-de-sac lot waiting for you. Contact listing office for covenants and restrictions. Minimum square feet for residence is 2,200 and maximum square feet for outbuildings is 1,500. One additional 1.94 acre lot available - ADJACENT TO THIS PROPERTY.

12642884 MLS ⋅ ACTIVE Status

Build your dream home on this tree lined lot at this premium location! 2+ Acre Cul-de-sac lot waiting for you. Contact listing office for covenants and restrictions. Minimum square feet for residence is 2,200 and maximum square feet for outbuildings is 1,500. One additional 1.94 acre lot available - ADJACENT TO THIS PROPERTY.

809 Indian, Woodstock

$70,000

Build your dream home on this tree lined lot at this premium location! 1.9 Acre Cul-de-sac lot waiting for you. Contact listing office for covenants and restrictions. Minimum square feet for residence is 2,200 and maximum square feet for outbuildings is 1,500. One additional 2.09 acre lot available - ADJACENT TO THIS PROPERTY.

12642886 MLS ⋅ ACTIVE Status

Build your dream home on this tree lined lot at this premium location! 1.9 Acre Cul-de-sac lot waiting for you. Contact listing office for covenants and restrictions. Minimum square feet for residence is 2,200 and maximum square feet for outbuildings is 1,500. One additional 2.09 acre lot available - ADJACENT TO THIS PROPERTY.

810 Indian, Woodstock

$600,000

THIS PARCEL IS BEING SOLD IN COMBINATION WITH THE 3 ACRE PARCEL DIRECTLY TO THE NORTH. Pin (13-06-301-003) FOR A TOTAL OF 10 CONTIGUOUS ACRES. DIRECTLY ACROSS THE STREET FROM EMRICSON 60 ACRE OUTDOOR PARK AND RETREAT. JUST MINUTES FROM DOWNTOWN, METRA, AND WOODSTOCK SQUARE.

12530055 MLS ⋅ ACTIVE Status

THIS PARCEL IS BEING SOLD IN COMBINATION WITH THE 3 ACRE PARCEL DIRECTLY TO THE NORTH. Pin (13-06-301-003) FOR A TOTAL OF 10 CONTIGUOUS ACRES. DIRECTLY ACROSS THE STREET FROM EMRICSON 60 ACRE OUTDOOR PARK AND RETREAT. JUST MINUTES FROM DOWNTOWN, METRA, AND WOODSTOCK SQUARE.

13902 Kishwaukee Valley Road, Woodstock

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