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629 N Madison Street, Woodstock
$249,000
2 Beds ⋅ 2 Baths ⋅ 12792996 MLS ⋅ NEW 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

1411 Westwood Trail, Woodstock
$550,000
4 Beds ⋅ 4 Baths ⋅ 12780916 MLS ⋅ PRICE CHANGE Status
Gorgeous custom-built 4-bed/3.5-bath home on a private, wooded 3/4-acre lot with over 4,200 sq ft of living space! This beautiful home has so much to offer, including smart home features like Wi-Fi-enabled smart switches, an Amana smart HVAC system and Alexa voice control. As you enter, you're welcomed by a formal dining room with rich Brazilian cherry hardwood floors that flow throughout the main level. The dining room leads into the spacious family room, complete with a cozy gas fireplace, which opens to the stunning chef's kitchen featuring a large island with breakfast bar, custom maple cabinetry, granite countertops and stainless steel KitchenAid appliances. Just off the kitchen, the first of two spacious heated sunrooms is the perfect spot to unwind and enjoy the peaceful surroundings. A convenient laundry room and half bath complete the main level. Upstairs, the luxurious primary suite offers a private balcony and en-suite bath. Three additional generously sized bedrooms and another full bath complete the second floor. The finished walkout basement provides even more room to spread out, featuring a large recreation/family room with a second fireplace, the second heated sunroom, a wet bar/kitchenette and a separate storage area or workshop. Step outside and enjoy your own private outdoor oasis! With multiple outdoor living spaces, including a screened patio, deck and lower-level brick paver patio, there's plenty of room to entertain, relax or simply take in the peaceful wooded setting. The attached 3.5-car garage is heated and has epoxy flooring. Recent updates include a new 97% efficient Amana smart HVAC system (2024), water heater (2022), basement kitchen appliances (2022) and more. You truly can't beat this home or its location, just minutes from historic Woodstock Square, the commuter train, parks, grocery stores and so much more!

1411 Westwood Trail, Woodstock

15309 Kishwaukee Valley Road, Woodstock
$1,235,000
5 Beds ⋅ 5 Baths ⋅ 12784985 MLS ⋅ PRICE CHANGE Status
***BUYERS*** For a qualified buyer, seller is offering a 2-1 temporary interest rate buydown or a permanent interest rate buydown, subject to buyer qualification, lender approval, and applicable loan program requirements.12-Acre Estate * 5 Bedrooms * 4.1 Baths * 7,279 Sq. Ft. * 8-Car Garage * Custom Kitchen * Near Downtown Woodstock Set amid approximately 12 acres of rolling countryside and mature trees, this custom-built French Provincial estate at 15309 Kishwaukee Valley Rd in Woodstock offers 7,279 square feet of distinctive living space, 5 bedrooms, 4.1 baths, and an 8-car garage. The custom-updated kitchen showcases Thermador and Viking appliances, bespoke cabinetry, and an oversized island with a copper countertop and prep sink. A dramatic great room features soaring vaulted ceilings, a floor-to-ceiling stone fireplace, hardwood flooring, and expansive windows framing the surrounding landscape. The first-floor primary suite offers a private retreat with dual walk-in closets, heated bathroom floors, a Jacuzzi tub, and an oversized walk-in shower. Four additional bedrooms provide versatile accommodations, while the finished walkout lower level features a recreation area, fitness room, full bath, generous storage, and direct access to the lower-level garage. Outdoor living unfolds across an expansive wraparound deck with an outdoor fireplace, a walkout patio, waterfall feature, winding driveway, and landscaped grounds. Approximately 12 acres provide room to explore, with walking paths, an outdoor shed with loft, custom chicken and duck coops, and built-in dog kennels. Additional improvements include a custom-updated front door, fresh interior paint, luxury vinyl plank flooring, LED lighting, a whole-house security system with cameras, and a new water heater. Enjoy the privacy and open setting of country estate living with convenient access to historic downtown Woodstock, local shopping, and dining. A rare opportunity to own a commanding French Provincial estate where grand custom architecture, refined luxury, and extraordinary acreage come together. From the dramatic one of a kind interiors and expansive 8 car garage capacity to the sweeping grounds and distinctive outdoor amenities, this remarkable Woodstock property delivers PRIVACY, LUXURY, and the presence of a true country castle.

15309 Kishwaukee Valley Road, Woodstock

1000 Dakota Drive, Woodstock
$475,000
3 Beds ⋅ 3 Baths ⋅ 12780714 MLS ⋅ CLOSED Status
Welcome to 1000 Dakota Drive, A Stunning Custom-built quality construction Ranch Home offering almost 4,000 square feet of living space, situated on over a half-acre in the highly sought-after Dakota Ridge subdivision. With nearly 2,000 square feet on each level, this exceptional home offers an impressive combination of space, quality & functionality.Exquisite, move-in-ready home, professionally painted in a sophisticated neutral palette. The original owner was a landscape architect & the professionally designed, master-planned grounds are truly extraordinary, creating a private outdoor oasis. The brick & cedar exterior welcomes you with a charming 17x21 brick paver front porch. Designed for everyday living, this home is equally a dream for entertaining. An elegant foyer with crown molding, formal living & dining rooms offer timeless elegance & versatile spaces for gatherings, intimate entertaining & memorable occasions. French doors lead to the first-floor office, while gleaming solid hardwood flooring flows into the dramatic cathedral-ceiling family room, where a beautiful stone fireplace is framed by a wall of windows filling the space with natural light. The fireplace features gas logs, was originally wood-burning & can be converted back. Imagine cozy evenings by the fire while enjoying picturesque views of the expansive backyard. The open-concept kitchen is truly the heart of the home, featuring a vast center island, abundant cabinetry, generous countertop space, recessed lighting & pantry storage-a chef's delight perfect for everyday meal prep & large holiday gatherings. 3 generously sized bedrooms include a luxurious primary suite with vaulted ceiling, large walk-in closet & deluxe en-suite bath featuring a jetted tub, walk-in shower & double-bowl vanity-a true sanctuary of comfort & privacy. The 1st-floor office with French doors & closet offers flexibility as a home office or potential 4th bedroom. 1st-floor laundry adds everyday convenience. The full basement is a remarkable extension of the home, featuring a deep-dig design with high ceilings, partially finished living area & a 3rd full bath, additional storage & an incredible dedicated dream shop/workshop area with extensive electrical service, outlets & exhaust fan system. The finished areas offer possibilities for a recreation room, theater/media area, hobbies, games, exercise room & more. This versatile lower level gives everyone room to spread out & can evolve with your needs for years to come. Sump pumps with interior drain tile & a Watchdog battery backup provide added peace of mind along with the whole house generator! Step outside to the spectacular backyard, where the professionally landscaped grounds are a true showstopper. The expansive 700-square-foot maintenance-free Trex deck, approximately 29x32, is perfect for sunset cocktails, morning coffee, entertaining large gatherings & enjoying the serene surroundings. It features a retractable electric awning for shade, natural gas line for your grill & 3 raised garden beds with a buried water line for convenient watering. The concrete driveway includes an extended side drive for easy vehicle turnaround.The oversized 29x20 3-car garage offers tremendous functionality with a brand-new epoxy floor, whole-house fan, additional electrical service/outlets & included air compressor. Additional quality & convenience features include nine-foot ceilings, six-panel doors, ceiling fans throughout, oversized Leaf Guard gutter/downspout system, whole-house generator, ADT security system, power-vent water heater, April Aire whole-house humidifier & Lennox furnace & central air approximately 3-5 years old. Located on the peaceful edge of town while still minutes from historic Woodstock Square, Emricson Park, Woodstock Water Works Park, shopping, schools & the Metra train. A truly exceptional home offering quality construction, extraordinary grounds, incredible workshop space & a setting you will be proud to call your own!

1000 Dakota Drive, Woodstock

688 W South Street, Woodstock
$950,000
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

1004 Golden Avenue, Woodstock
$475,000
3 Beds ⋅ 3 Baths ⋅ 12734802 MLS ⋅ PENDING Status
The look of millions for the cost of much less....That's what you get with this Golden opportunity! The first thing you notice while driving down Golden Avenue is the stunning and massive stone mailbox that mirrors the stonework inside your new kitchen and living space. Once you step inside, you'll notice 20 foot ceilings soaring over the gas fireplace framed in by a beautiful stone wall. This open concept is flooded with natural light and grandeur, and only the start of your magnificent home. The kitchen is the center of every home, and this one doesn't hold back. It's next-level. A massive 12' x 6' quartz island with built-in wireless phone charge, a grand 36-inch stove with a dramatic stone surround, and top-of-the-line appliances are available that would make any chef jealous. Towering above it all, two breathtaking crystal chandeliers that tie in perfectly with the crystal accents found throughout the home, adding an extra level of elegance. And because ambiance matters, in-ceiling speakers seamlessly connect to the 85-inch TV, making movie nights and dinner parties feel like a cinematic experience. Of course, every dinner party needs a cocktail for the occasion, which is why when you enter the hallway you find a sleek and elegant dry-bar. Further down the hallway you'll find that luxury is everywhere. Both full bathrooms are decked out in floor-to-ceiling marble with opulent gold accents, while the master bath features a two-person shower. The grand arches throughout tie everything together in breathtaking harmony, mirroring the striking kitchen design. Okay, but what about the floors? Hardwood. Rich natural solid hardwood flooring flows throughout the first floor, complementing the timeless wainscoting that adds depth and character to every room. Did you notice the floor in the kitchen? That trap door leads down into a whopping 1500 square foot open space basement. Your desire for the perfect entertaining area is just a pool table and a flat screen TV away. Space still for the arcade game or perhaps a wet bar overlooking a foosball table. The basement has a bathroom and ceiling lighting throughout, it is ready to become whatever your heart desires! Just think big! This home looks and feels like a million dollar home, yet it is nestled comfortably on the edge of downtown. Items considered personal property are available for purchase. Don't miss this Golden opportunity to live in this breathtaking beauty.

1004 Golden Avenue, Woodstock

446 Borden Street Unit #446, Woodstock
$239,900
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

1360 Infanta Court, Woodstock
$545,000
5 Beds ⋅ 5 Baths ⋅ 12730098 MLS ⋅ CLOSED Status
Nestled on a quiet cul-de-sac in the sought-after Dominion Heights neighborhood, this custom East-facing home sits on over 1.5 acres adjacent to Yonder Prairie Conservation, offering breathtaking year-round views, exceptional privacy, and abundant wildlife. Featuring 5 bedrooms, 3 full baths, 2 half baths, and a fully finished walkout basement, this home is filled with natural light and designed for both comfortable everyday living and entertaining. There is only 1 refrigerator in the kitchen, that is to stay. The main level offers a private office, spacious kitchen with walk-in pantry, built-in buffet, wet bar, dining room, and a dramatic family room with vaulted ceilings and a cozy wood-burning fireplace. Upstairs, you'll find 3 bedrooms, including an expansive primary suite with a private balcony overlooking the conservation area, a walk-in closet, and a spa-like bath with separate vanities, whirlpool tub with skylight, and separate shower. The two additional upstairs bedrooms share a convenient Jack-and-Jill bathroom with separate vanity areas. Outdoor living is equally impressive with a large deck, brick paver patio, mature trees, and spectacular views in every season. The fully finished walkout basement with high ceilings is ideal for multigenerational living, offering 2 additional bedrooms, a full bath, a private garage entrance, and a spacious family room with a gas fireplace, perfect for movies, gaming, fitness, or a second living area. Additional highlights include city water and sewer, no HOA fees, newer roof, newer main furnace, new A/C, and a new water heater. This beautifully maintained home offers the perfect combination of space, flexibility, modern updates, and an unmatched natural setting.

1360 Infanta Court, Woodstock

1020 Winslow Avenue, Woodstock
$392,000
3 Beds ⋅ 2 Baths ⋅ 12724682 MLS ⋅ CLOSED Status
This beautifully updated 1,750-square-foot one-story ranch home offers perfect modern living. The spacious three-bedroom layout features a private master suite complete with a beautifully updated master bathroom. Step inside to find fresh interior paint and stunning hardwood flooring stretching through the main living areas. Cozy new carpet adds warmth to all of the bedrooms. The heart of the home shines with a updated kitchen boasting sleek new countertops. Both bathrooms have been modernized with stylish, fixtures. Brand-new window blinds are installed throughout the home, offering immediate privacy and light control. Every detail has been meticulously refreshed, meaning you can move right in without the stress of remodeling. Combining classic ranch-style charm with entirely new finishes, this turnkey property is ready to welcome you home.

1020 Winslow Avenue, Woodstock

107 W Melody Lane, Woodstock
$225,000
4 Beds ⋅ 2 Baths ⋅ 12722578 MLS ⋅ CLOSED Status
Opportunity awaits in this 4-bedroom, 1.5-bath split-level home in historic Woodstock! Offering an abundance of potential, this property is ready for your vision and personal touches. The spacious floor plan features four generously sized bedrooms, a large living room that opens into the kitchen. Additional highlights include an attached 2-car garage and a fully fenced backyard with plenty of room to enjoy. This home is in need of repairs and presents an exciting opportunity for buyers looking to renovate, customize, and potentially build equity. Conveniently located just steps from Northwood Middle School and near Metra train access, dining, shopping, historic downtown Woodstock, and more. Bring your ideas and transform this property into the home you've been envisioning!

107 W Melody Lane, Woodstock

704 N Rose Farm Road, Woodstock
$715,000
4 Beds ⋅ 5 Baths ⋅ 12713168 MLS ⋅ CLOSED Status
**MULTIPLE OFFERS**Welcome home to this exceptional ranch estate offering year-round enjoyment on 2.31 private acres. Designed for both everyday living and unforgettable entertaining, this fully renovated home combines luxury, comfort, and incredible outdoor amenities. Step inside to discover beautiful herringbone hardwood floors and an open-concept layout featuring a spacious family room with a cozy gas fireplace. The chef's kitchen is the heart of the home, showcasing a massive center island, premium appliances including a Bosch dishwasher, drawer microwave, and 36-inch range, plus a walk-in pantry with abundant storage. The main level offers four bedrooms and two-and-a-half baths, including a private primary suite with a walk-in shower, double vanity, and walk-in closet. Convenient main-floor laundry and an oversized heated attached garage add to the home's functionality. The finished lower level provides additional living space with a fifth bedroom or office, a full bath featuring a large shower, a wet bar, a large storage room, and a walk-in wine room that could also serve as a humidor. Outside, you'll find a true backyard retreat. Enjoy the stamped concrete patio, outdoor kitchen with a brand new built-in grill, two fire pits, hot tub, versatile sports court, and a pool house Cabana complete with a bathroom, outdoor shower, and walk up wet bar. The impressive 12-foot-deep pool features both a diving board and slide, all surrounded by a roughly 60-foot privacy wall of evergreens. Additional recent improvements include a whole-home water softener, private dedicated well, winterized cabana line sets, new pool heater, wireless pool control system, and a radon mitigation system to name a few. The property is unincorporated and lot size allows for up to three horses, with the option to construct stables, an outbuilding for your hobbies and enjoyment. Rear neighboring land is zoned agricultural, providing added privacy and open views. With low property taxes, exceptional indoor and outdoor living spaces, and endless opportunities for recreation and entertaining, this property truly has it all. Don't miss your chance to make this extraordinary home your own.

704 N Rose Farm Road, Woodstock

1019 N Madison Street, Woodstock
$215,000
2 Beds ⋅ 1 Baths ⋅ 12702764 MLS ⋅ CLOSED Status
Charming Ranch in a Prime Woodstock Location with an Incredible Backyard! This move-in ready 2-bedroom ranch offers the perfect blend of comfort, updates, and an unbeatable location. Hardwood floors flow throughout much of the home. Large windows fill the home with natural light, creating a warm and inviting atmosphere you'll love coming home to. The true standout is the expansive, nearly one-third acre fenced backyard-a rare find this close to downtown. Whether you envision summer barbecues, gardening, a play area for pets or kids, or simply relaxing in your own private outdoor retreat, this yard offers endless possibilities. A detached one-car garage provides additional storage and convenience. Major updates include: New roof, siding, and gutters on the house (2024), new garage siding and gutters (2024), new garage roof (2023), furnace and central air (2018), Washer and dryer (2023). Close to Woodstock's charming Historic Square, where you'll enjoy locally owned shops, restaurants, seasonal events, farmers markets, and year-round community activities. With the Metra train station just minutes away, commuting to Chicago or exploring the surrounding area couldn't be more convenient.

1019 N Madison Street, Woodstock

18918 Bunker Hill Road, Woodstock
$700,000
5 Beds ⋅ 3 Baths ⋅ 12679135 MLS ⋅ CLOSED Status
Imagine The Possibilities - Income Potential, Indoor Storage, Rental Opportunity, Farm Dreams, Or The Ultimate Family Compound. Because TWO Houses Really Are Better Than One! Set On A Sweeping 19.62 Acres Zoned Agricultural (A-1), This Former Dairy Farm Is Move-In Ready To Live, Work AND Play! Perched On The Hill With Country Views In Every Direction, The Property Anchors Around Two Homes. House 1 Is A Character-Rich Farmhouse Brimming With Original Charm: A Vaulted Living Room Anchored By A Floor-To-Ceiling Brick Wood-Burning Fireplace, Original Hardwood Floors, Warm Wood-Plank Ceilings, And Built-In Knotty-Pine Bookshelves, Desk, And A Classic Glass-Paned French Door. The Updated Kitchen Shines With Raised-Panel Wood Cabinetry, Stainless Appliances, Solid-Surface Counters, And A Window Over The Sink Framing Green Country Views. Offering 5 Bedrooms - A First-Floor Primary Plus 4 Bedrooms Up - Generously Sized Rooms, A Full Basement, And A Main-Floor Bath With A Walk-In Closet And Tiled Walk-In Shower, With A Brand-New Tub (credit for installing). House 1 Pairs Farmhouse Soul With Everyday Function. House 2 Is A Comfortable Ranch With A Bright, Open Floor Plan Where The Kitchen - Stainless Appliances, Ample Oak Cabinetry, And A Country-View Window - Flows Into A Spacious Living And Dining Area Filled With Natural Light. It Offers 3 Bedrooms (Including One With A Charming Built-In Knotty-Pine Wardrobe), A Full Bath, And A Full Basement With Finished Bonus Space Below - Ideal For Extended Family, A Tenant, Guest Quarters, Or Rental Income. The OUTBUILDING Of Your Dreams Is A Massive 60 X 160 Barn Built For Serious Use: Soaring Timber-Truss Ceilings, Concrete Floors, Oversized Doors That Swallow Equipment, Trailers, Or An RV, Abundant Lighting, And Even Former Horse Stalls For The Equestrian Buyer. Tucked Inside Is A HEATED Workshop With Overhead Heaters, Work Benches, And A Finished Hangout Space - The Ultimate Hunters' Lodge, Hobby Shop, Or Man Cave. A One-Of-A-Kind Bonus: The Farm's Original Silo Foundation Has Been Repurposed Into A Screened Party Room With Power And Heat, A Vaulted Beamed Ceiling, Cafe Lighting, A Built-In Bar, And Walls Of Windows Overlooking The Woods - Built For Entertaining A Crowd. The Back 10 Acres Are Leased Annually To A Longtime Local Farmer, Providing Built-In Agricultural Use And Income. Recent Updates Include 2021 Roofs And Vinyl Siding. The Property Has A Shared Well Between The Two Homes - Buyers Should Confirm Financing Compliance With Their Lender. So Much To See, So Much To Love In This Rare McHenry County Compound. While Beautifully Maintained, The Property Will Be Sold In As-Is Condition.

18918 Bunker Hill Road, Woodstock

16512 Nelson Road, Woodstock
$995,000
6 Beds ⋅ 5 Baths ⋅ 12671539 MLS ⋅ CONTINGENT Status
Stunning Luxury Estate on 10.12 Acres - A Rare Opportunity - BRAND NEW Driveway!! Experience the perfect blend of elegance, comfort, and country living in this remarkable estate, nestled on over 10 acres of beautifully maintained land. Boasting more than 8,000 square feet of finished living space, this impressive home features 9 spacious bedrooms and 5 full bathrooms-offering an ideal retreat for large families, multigenerational living, or hosting guests in style. Step inside to be welcomed by elegant flooring and a thoughtfully designed layout. The main level includes a private in-law suite and a generously sized laundry room for ultimate convenience. At the heart of the home, the chef's kitchen delights with abundant cabinetry, expansive counter space, high-end stainless steel appliances, and a sun-drenched breakfast area. Relax and unwind in one of two cozy family rooms, each with its own fireplace. The luxurious primary suite is a true sanctuary, featuring a private sitting room, dual walk-in closets, and a spa-inspired en-suite bath with a whirlpool tub, dual vanities, and an oversized shower. The fully finished basement is designed for entertaining, offering a full bar, a billiards room, and two additional bedrooms. Radiant flooring in both the basement and the fully finished 3-car garage ensures year-round comfort. Zoned AG-2, the property allows for horses and livestock, providing a true country lifestyle with modern luxury. Enjoy outdoor living with a brand-new deck, a cozy backyard fire pit, and plenty of space for recreation or future additions. This exceptional estate offers the rare combination of expansive land, luxurious amenities, and a flexible layout to meet your family's needs. Discover your dream home where comfort meets countryside charm.

16512 Nelson Road, Woodstock

14914 W South Street Road, Woodstock
$260,000
3 Beds ⋅ 1 Baths ⋅ 12663690 MLS ⋅ CLOSED Status
Highest and Best Due by 5pm on 6/4/26 - Nestled on a SPACIOUS COUNTRY LOT just MINUTES FROM TOWN, AND ZONED A1! This charming RANCH offers peaceful surroundings with neighboring pasture views, LOCAL WILDLIFE, and a quiet setting that feels like an escape from the everyday. Inside, you'll find comfortable living spaces, a functional layout, patio access, and a flexible laundry/mudroom area that adds extra convenience and storage. In 2013, the home underwent EXTENSIVE UPDATES, including electrical, plumbing, HVAC, windows, doors, and exterior wall reconstruction with added foam insulation for efficiency and comfort. A NEW Roof and a NEW Well in 2025, giving buyers peace of mind with many major improvements already completed.

14914 W South Street Road, Woodstock

14401 Trinity Court, Woodstock
$590,000
5 Beds ⋅ 3 Baths ⋅ 12657688 MLS ⋅ CLOSED Status
Welcome to this gorgeous 2-story Farmhouse Colonial nestled on a beautifully landscaped 1/2-acre lot in the highly sought-after Westwood Lakes Estates Subdivision with gorgeous views of the Yonder Prairie Nature Preserve and just a short 5-minute drive to the charm and character of Woodstock's Historic Downtown. From the moment you step inside, you'll be captivated by the quaint front porch, soaring 9-foot ceilings, freshly painted modern designer-inspired color palette, elegant arched doorways, refinished Brazilian Cherry Floors, designer light fixtures, and upgrade base/crown molding that add architectural charm throughout. The sensational open-concept layout is perfect for both everyday living and effortless entertaining! At the heart of the home is the stunning island kitchen, featuring rich custom birch cabinetry, newer upgraded appliances, abundant counter space, and seamless flow into the spacious eating area and inviting spacious Family Room with cozy fireplace and custom built in cabinets. Whether hosting gatherings or enjoying quiet mornings, this kitchen truly delivers both beauty and function. Additional features include first floor Den with custom floor to ceiling bookshelves-ideal for home office or quiet reading space. One of the home's standout features is the sensational Sunroom showcasing a dramatic wood-vaulted ceiling and walls of windows that bring the outdoors in and featuring panoramic views of gorgeous yard. Step outside to the spacious wood deck and beautifully designed paver patio-ideal for Summer barbecues, evening gatherings, and outdoor entertaining in your private backyard retreat. Upstairs, the spacious primary suite offers a luxurious escape Primary Bedroom Suite with walk-in closet and full Bath. Generously sized secondary bedrooms and a versatile Bonus Room (optional 5th BR) provide flexible space for a home office, playroom, media room, or guest suite. Additional highlights include a 3-car garage and a lookout English Basement with 9' ceilings and rough-in for additional bath-ready for your custom finishing touches. Ideal for future Rec Room, Home Theater, Gym, and added Entertaining Space. Located near parks, award-winning schools, and all the vibrant amenities of downtown Woodstock-including quaint local shops, popular restaurants, the renowned Woodstock Opera House, and year-round community events-this home offers the perfect blend of peaceful suburban living and small-town charm. Added features include newer Roof, Furnace-2018, 200A Elec. Panel, and excellent closet/storage space. A rare opportunity to own a truly exceptional home in an unbeatable location! Not Just a House... Your Next Home!

14401 Trinity Court, Woodstock

713 Carlisle Drive, Woodstock
$245,000
2 Beds ⋅ 2 Baths ⋅ 12652611 MLS ⋅ CLOSED Status
Welcome to this lovely two story townhome with a full basement, located in a quiet neighborhood on the north side of town. The open concept first floor has brand new carpeting and fresh paint, creating a bright space for entertaining friends and family or relaxing after a long day. A concrete patio and and rear yard offer additional space to enjoy. Upstairs, you'll find two bedrooms and a full bath as well as a small loft area, perfect for curling up with a cup of coffee or a good book. Located a few blocks from Olson Park, where you can advantage of the playground, baseball fields, basketball courts, and tennis courts. Just a short drive to the train station and downtown Woodstock square, making it convenient for work, restaurants, and shopping. New high efficiency furnace (12/2025), new water heater (2026), roof replaced 2020.

713 Carlisle Drive, Woodstock

15214 Shamrock Lane, Woodstock
$710,000
3 Beds ⋅ 4 Baths ⋅ 12617521 MLS ⋅ CLOSED Status
Peace and quiet await in this custom-built home offering more than 4,000 square feet of living space on a private 5-acre wooded setting just minutes from town. Step inside and appreciate the flowing open floor plan designed for both everyday living and entertaining. At the heart of the home is the stunning great room featuring vaulted ceilings with handcrafted beams and a wall of windows overlooking your own private natural retreat. The spacious kitchen includes solid-surface countertops, under-cabinet lighting, a large island with ample prep space and a full walk-in pantry. The formal dining room is ideal for gatherings, while the cozy sunroom provides the perfect place to relax and opens to one of the brick patios. The expansive primary suite features a gas fireplace, private balcony and walk-in closet with built-in cabinetry. The luxurious bath includes a large whirlpool tub accented by a custom stained-glass window. A main-floor office with built-in cabinetry, along with a mudroom featuring laundry and a full walk-in closet, complete the first floor. The walkout lower level with 9-foot ceilings offers a spacious family room with fireplace and patio access. There are guest bedrooms along with a flexible craft or project room, and display cases for collections. A separate staircase leads directly from the basement storage room to the attached 3-car garage. Outside, the paver brick driveway enhances the home's curb appeal. With no HOA restrictions, you have the freedom to clear land, add walking trails through the woods, or simply enjoy the peaceful natural surroundings. Zoned A-1, agriculture. Animals are allowed. This property is truly your private oasis.

15214 Shamrock Lane, Woodstock

980 Dakota Drive, Woodstock
$607,000
4 Beds ⋅ 5 Baths ⋅ 12605762 MLS ⋅ CLOSED Status
Architectural Excellence awaits at 980 Dakota Drive in Woodstock! This inspired masterpiece nestled between rolling countryside and historic downtown charm offers a Premier Location & Lifestyle. Signature Interiors welcome you with a dramatic two story entry and wrap around balcony, 4 bedrooms, 3 full and 2 half baths. The spacious kitchen is designed with sleek granite countertops, center island, custom cabinetry, and substantial pantry. Main-Level design is elevated with natural slate and maple hardwood flooring and executive home office with a private fireplace. The spacious living room is an Entertainer's Dream, with custom built-ins, surround-sound, and wine bar with dedicated refrigerator. Second floor living is accented by a sun drenched vaulted atrium room with beautiful south facing views and spectacular sunsets. The Primary Suite is a sanctuary complete with vaulted ceilings, a private sitting area and balcony with serene vistas of the wooded yard and private pond. The Luxury Bath with Jacuzzi soaking tub, oversized walk-in shower, and dual vanities flows into an Expansive Dressing Room featuring direct, convenient access to the upper-level laundry. A Junior Suite provides a private balcony and bath amenities. Walk-Out Lower Level is finished with a full wet bar and recreation areas leading outdoors to a sprawling patio showcasing a striking three-story stone fireplace. The thoughtfully landscaped 1.12 acres features a 2,200-sq-ft fenced garden with custom pergola, a private pond and mature trees. Car or toy enthusiasts will love the expansive garage equipped with a professional mechanic's lift, accommodating up to 4 vehicles. Recent Updates include New Roof (2021) New Driveway (2023) Furnace, AC and tankless water heater (2025). Located within the Award-Winning D200 School district, Emricson Park (1 Mile) with access to paved nature trails, pickleball, tennis, volleyball, disc golf, and the Woodstock Water Works aquatic center and 5 miles to the Bull Valley Golf Club and Woodstock Country Club. Easy access to the Historic Woodstock Square, Metra, boutique dining, and the world-renowned Woodstock Opera House.

980 Dakota Drive, Woodstock

720 Serene Trail, Woodstock
$350,000
2 Beds ⋅ 3 Baths ⋅ 12633255 MLS ⋅ CLOSED Status ⋅ Serenity Creek BLDG.
Tucked away on the West Side of Town, this is active adult (55+) living in a private cul-de-sac community. If you are looking for quiet and peacefulness, this 1/2 duplex, with BRICK exterior and a view of Conservation is the Serenity you might be hoping for! Reschke Quality built and handsomely appointed this "no-step" home offers ADA design for ease AND mobility. Features such as 36" and 48" wide doorways; elevated electrical outlets; built-in nightlights; raised height outlets; roll-out pantry shelves; drawer style dishwasher and a Chair Lift to the English Lower Level. All Serenity Creek units were built with solid construction and extra details such as Pella Pro-Line wood casement windows for energy efficiency and ease of operation. Solid 6-panel oak doors and full oak trim throughout. The full FINISHED basement with a 9' ceiling offers tremendous additional living space and another FULL Bath! NEW Roof in 2026 and 2023 Air Conditioning, 2016 Water Heater. This is a 55+ community - only 1 occupant is required to meet the requirement. Just a hop, skip to Emricson Park and amenities!

720 Serene Trail, Woodstock

920 N Madison Street, Woodstock
$240,000
3 Beds ⋅ 1 Baths ⋅ 12622097 MLS ⋅ CLOSED Status
Charming all-brick 3-bedroom, 1-bath home full of character! The main level features two comfortable bedrooms, a full bathroom, a welcoming living room, and a spacious dining room highlighted by beautiful built-in corner cabinets-perfect for showcasing your favorite pieces. The kitchen is conveniently located just off the dining room, making entertaining easy. Upstairs, you'll find a private third bedroom along with an expansive bonus room-ideal for a home office, playroom, or creative space. Outside, enjoy a generous backyard with plenty of room for summer gatherings, BBQs, and outdoor fun. A detached 2.5-car garage adds even more value, offering ample space for parking, storage, or hobbies. This home blends classic charm with functional living-don't miss the opportunity to make it yours! home is being sold as-is. all in home appliances stay.

920 N Madison Street, Woodstock



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