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15309 Kishwaukee Valley Road, Woodstock
$1,235,000
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

708 S Rose Farm Road, Woodstock
$1,990,000
5 Beds ⋅ 5 Baths ⋅ 12763036 MLS ⋅ ACTIVE Status
** Seller Financing Options Now Available - Ask about Options** 20 ACRE LUXURY HOME AND EQUESTRIAN FACILITY - 30 STALLS TOTAL; INDOOR AND OUTDOOR ARENAS AS WELL AS PLENTY OF PASTURES. EVERYTHING IS MOVE-IN-READY! The MAIN BARN was built by Lester, is 3-years NEW and is a white pole building with a black roof and wainscoting. Fully Insulated Walls with radiant floor HEAT and supplemental forced air heat. It features 16 Stalls; all equipped with mattresses, drop down stall fronts and electrical outlets. (6 Stalls are 12x12 with 12x24 run-outs; 10 Stalls are 10x12). Additional amenities include Viewing Room, Tack Rooms (2), Office, Bathroom, Indoor Wash Rack and Blanket Rack. HEATED INDOOR ARENA is 80x135x20 and features fiber footing, angled kickboards, large built-in mounting block. The interior walls are insulated and finished. There are 4 sliding windows for cross ventilation and 6 rows of lights. LARGE OUTDOOR ARENA was built with landscape fabric, limestone base and sand footing. It's finished with beautiful 4-Board Fencing. The separate barn entrance is a circle drive for easy in and out with trucks and trailers. ORIGINAL BARN by the house has been completely renovated. It features 5 Stalls (European Bamboo); 10x12 with swing-out feeders, mattresses and Dutch doors that open to 12x20 runouts. 8 PORTABLE LEAN-TOS WITH 9 OUTDOOR STALLS and storage. PADDOCKS AND PASTURES are constructed with 4-Board Wood Fencing. This lovely 2-Story Farmhouse sits on top of a hill overlooking the rest of the farm. There is original stone fencing around the perimeter of the property. It features 4,000 Sq Ft of finished space with 5 BR & 4.5 BA and has been COMPLETELY RENOVATED. Sellers added a Mud Room, Laundry Room, 1/2 Bath as well as other upgrades that have been finished to the period of the house to be historically correct. Large Formal Foyer with hardwood floors leads you to multiple rooms in the house...Large Kitchen with Eat-At Island is open to the Dining Room. The Kitchen features NEW white cabinets with crown molding, Quartz counters, Stainless Steel Appliances and a farmhouse sink. 4-SEASON ROOM / FAMILY ROOM faces south and has windows on 3 sides which provides maximum sun exposure and a beautiful view overlooking the pastures. LIVING ROOM features a beautiful bay window and a double-sided original stone fireplace that also serves the 1st Floor Bedroom with Full Bath. The 2nd floor features 3 BR & 2 BA; one is a shared Jack & Jill Bath. The Roof-Top-Deck is perfect for relaxing...day or night! The finished living space above the garage has its own separate entrance and includes a Sitting Room, Bedroom & Full Bathroom. It's perfect for the farm employee, Guest Quarters, In-Law or Related-Living Suite. NORTHEAST and NORTHWEST OUTBUILDINGS are primarily used for storage. (These two buildings have not been renovated.) This is your chance to own a historical property from 1815 with modern amenities. GREAT LOCATION: 5 Min to Woodstock for shopping, restaurants and the Metra and 1 Hour or less to 4 different show facilities. Zoned A1; Agriculture. *PLEASE ASK TO SEE THE ADDITIONAL FEATURES SHEET FOR FULL DETAILS * A PROOF OF FUNDS OR PREAPPROVAL LETTER IS REQUIRED AND A 24 HR NOTICE IS NEEDED FOR SHOWINGS TO BE APPROVED.* This property is also for lease: $10,000 for all or $6,000 for the Barn and Pastures.

708 S Rose Farm Road, Woodstock

1120 Dean Street, Woodstock
$349,900
5 Beds ⋅ 3 Baths ⋅ 12770635 MLS ⋅ PRICE CHANGE Status
Rare 5-bedroom, 1.5-story home in a prime Woodstock location-just 2 minutes from the Historic Woodstock Square and 1 minute to the local elementary school! Boasting hardwood floors throughout most of the main areas, this versatile floor plan features 3 main-level bedrooms and 2 upper-level bedrooms. The cozy family room centers around a warm fireplace and connects smoothly to the kitchen and dining spaces. Enjoy ideal indoor-outdoor living with 3 sets of sliding glass doors opening directly to an expansive screened-in porch overlooking the serene backyard. Massive walk-in attic offers incredible potential for future expansion or extra storage, plus a full basement and an attached 2+ car garage. Major peace of mind with extensive recent updates: roof, soffits, fascia, gutters, exterior stain, most windows, furnace, fridge, oven, and dishwasher! All appliances stay, including the garage fridge and chest freezer. Seller is providing a 1-year home warranty for the buyer's complete peace of mind.

1120 Dean Street, Woodstock

3208 S Country Club Road, Woodstock
$899,900
5 Beds ⋅ 2 Baths ⋅ 12762513 MLS ⋅ ACTIVE Status
Step back in time & experience the charm of what once was the Erckfritz Dairy Farm. Original farm Est. in the 1800s & has been held by the same family since 1940. Situated on 17.47 acres/zoned A-1/A-2, property offers a rare combination of historic character, income potential, & endless opportunities for hobby farming, horses, recreation, or future development. Classic 2-stry farmhouse offers apprx 2,066 sq feet of living space featuring 4-5 bdrms, 1 full bath, & 1 half bath. Enjoy morning coffee on the enclosed wraparound porch or evenings watching breathtaking sunsets. Primary bdrm features pvt balcony, perfect for taking in peaceful sunrises overlooking the countryside. Inside, find a lrg eat-in country kitchen w/abundant countertop space for meal prep, SS appliances, spacious DR w/built-in china cabinet, pocket doors, & beautiful original woodwork throughout. Parlor off LR makes an ideal home office, craft rm, or playrm, while flexible bonus rm can easily serve as fifth bdrm, teen retreat, or hobby space. Add'l features include a mudrm w/convenient access to the expansive rear deck. Property includes 3 outbuildings w/metal roofs, including the former 2-story dairy barn (35' x 77.5') that features concrete flrs, horse stall, hay loft, & abundant upper-level storage. Let your imagination run wild w/the potential to transform this structure into a stunning barn dominium, event venue, or gathering space that will have everyone talking for years to come! A lrg 2-story outbuilding (28' x 24') was converted into a chix house, complete with individual "chicken condos," while upper level provides exceptional storage space. Heated 4-car detached garage/workshop (90' x 30') offers concrete floors & ample rm for vehicles, equipment, or business use. Outside, the possibilities truly shine. Imagine a place where memories bloom as beautifully as the spring flowers & every season brings a little more magic to everyday life. Spring & summer brings family & friends together for backyard bbq's, friendly (& sometimes competitive!) baseball games & volleyball matches or game of croquet! Kids will love unforgettable summer pool parties while adults grill hot dogs on the expansive deck & enjoy the sunshine. As evening settles in, roast marshmallows over the fire pit, create gooey s'mores, & sing beloved campfire songs beneath a sky full of stars. With plenty of rm for entertainment, property is the perfect setting for graduation/wedding parties everyone will talk about for years to come! As autumn arrives, rake colorful leaves into giant piles just begging to be jumped into. Turn the barn into a delightfully spooky haunted house, carve jack-o'-lanterns to line the drive, & create a Halloween experience worthy of its own fairy tale. As winter arrives, the property transforms into a snow-covered wonderland! Build snowman & snow forts, enjoy exhilarating snowball battles, & watch children's imaginations come to life in a yard that seems made for magical winter adventures. Outdr enthusiasts will appreciate the shooting range, horseback riding opportunities, & abundant wildlife that regularly visits the property, including deer gracefully roaming the grounds. Your four-legged family members will think they've discovered paradise w/acres of rm to run, explore, chase butterflies & birds, & play to their hearts' content! More than a home, this is a place where traditions begin, milestones celebrated, & every season writes a beautiful new chapter in your family's story. Add'l updates include newer vinyl siding, updated electrical, & roof approx 10 years old. Located in highly sought-after Prairie Ridge High School district, this extraordinary property offers the peace & privacy of country living while remaining conveniently accessible to modern amenities. Whether you're dreaming of a hobby farm, equestrian property, event venue, multi-generational homestead, or simply a private country retreat, this historic farm offers a once-in-a-lifetime opportunity.

3208 S Country Club Road, Woodstock

863 Pleasant Street, Woodstock
$404,900
5 Beds ⋅ 3 Baths ⋅ 12772063 MLS ⋅ ACTIVE Status
Welcome home to this beautifully updated 5-bedroom, 3-bathroom raised ranch! This spacious home offers a fantastic layout with stylish updates throughout and plenty of room for everyone. The main level features a bright and inviting living room, formal dining room, and stunning kitchen with popular white cabinetry and a convenient peek-a-boo window overlooking the dining room. Three generously sized bedrooms are also located on the main level. New wood laminate flooring, fresh paint throughout, and new light fixtures give the home a clean, modern feel. All bedrooms are equipped with ceiling fans for added comfort. The finished lower level offers even more living space, including a spacious family room with a beautiful fireplace and built-in shelving, perfect for relaxing or entertaining. A wet bar adds an extra touch of convenience, while two additional bedrooms and a full bathroom make this level ideal for guests, a home office, or extended living arrangements. The oversized 3-car garage is a standout feature, offering plenty of room for vehicles, storage, hobbies, and workshop space. Step outside and enjoy the deck, gorgeous stamped-concrete patio, and nice-sized fenced backyard. House generator as well! With 5 bedrooms, 3 full bathrooms, two levels of finished living space, a huge 3-car garage, and numerous updates, this move-in-ready home has so much to offer!

863 Pleasant Street, Woodstock

526 W South Street, Woodstock
$250,000
5 Beds ⋅ 3 Baths ⋅ 12739289 MLS ⋅ CLOSED Status
You can OWN THIS HOUSE of INCREDIBLE CHARM in this IDEAL LOCATION and with a BEAUTIFUL FLOOR PLAN. Yes, IT NEEDS WORK to BRING IT BACK TO GLORY, but the PRICE IS RIGHT! An amazing 2,736 SQ FT of pure potential, built in 1900. The staircase is gorgeous with two STAINED GLASS windows along the way. The large Living Room is inviting and the separate Dining Room is perfect for a dinner party or game night. FIVE LARGE BEDROOMS! Plenty of storage and a full bath on each level with an additional half bath off the den. The back section of the house was once used as a professional doctor's office - It makes a great FAMILY ROOM with a lovely wall of windows. The two additional back rooms have no closets, but they make great bedrooms. There is an EV charging station at the side of the house by the driveway. This is an AS-IS SALE. Absolutely no repairs will be made by the seller.

526 W South Street, 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

11012 Lucas Road, Woodstock
$699,900
5 Beds ⋅ 4 Baths ⋅ 12730559 MLS ⋅ CONTINGENT Status
Welcome home to this spacious and beautifully maintained two-story retreat in unincorporated Woodstock! This home is offering 5 bedrooms, 3.5 bathrooms, and 2,448 square feet of comfortable living space, sitting on 10 acres! Nestled on a picturesque setting with a private pond, this home combines warmth, charm, and functionality throughout. Enjoy cozy evenings by one of the two wood-burning fireplaces, rich hardwood floors, and the convenience of central vacuum. The stunning primary suite features a balcony along with a private walkout deck - the perfect place to enjoy your morning coffee or unwind at sunset. The walkout basement includes a mother-in-law suite, offering ideal space for guests or extended family. Step outside to enjoy the spacious deck, peaceful views, and added convenience of an electric fence. This home offers the perfect blend of comfort, character, and serene outdoor living.

11012 Lucas Road, Woodstock

370 Lincoln Avenue, Woodstock
$258,000
5 Beds ⋅ 3 Baths ⋅ 12691511 MLS ⋅ CLOSED Status
Opportunity awaits in this classic home that has been lovingly owned by the same family for over 40 years. While the home is ready for updating, it offers timeless architectural character, quality craftsmanship, and an unbeatable location, all the perfect ingredients to create your dream home. Step inside to discover striking natural-tone staircase millwork, beautiful transoms above the doorways, solid 5-panel wood doors, nearly 9-foot ceilings, built-in cabinetry, and two charming fireplaces (shared chimney has been capped). One of the five bedrooms is on the main level. Outside, enjoy barbecues on the deck overlooking the spacious yard that backs to a school field and playground, providing an open, park-like setting. The property has been maintained without pesticides and features an established collection of perennials and edible gardens, including hostas, strawberries, black raspberries, asparagus, irises, and a composting area. A detached two-car garage with a unique canoe bump-out offers additional storage for outdoor enthusiasts. Newer Roof, and A/C in 2026. The location is truly exceptional-just minutes from vibrant downtown events, restaurants, shopping, the Metra station, schools, and the library. Whether you're looking to restore its original beauty or update it with your own style, this home offers incredible potential in one of the area's most desirable neighborhoods. Home is being sold As-is.

370 Lincoln Avenue, Woodstock

2119 Serenity Lane, Woodstock
$449,000
5 Beds ⋅ 3 Baths ⋅ 12711480 MLS ⋅ ACTIVE Status
This beautiful home in The Ponds of Bull Valley has so much to offer its new owner! You'll be delighted by the spacious rooms on the first floor, flowing from one to another. Entertaining is easy as the formal dining room offers space for intimate get togethers, and the kitchen opens to the Family Room, an area where everyone can gather around the fireplace. Upstairs are four spacious bedrooms with large windows allowing for plenty of sunshine, including the large Primary with ensuite bath. There is also another full bath to be shared by the three upstairs bedrooms. Extending the living space, the full finished basement boasts another fireplace and a 5th bedroom with access to a full bathroom. Double French doors provide access to the brick paver patio, where you can enjoy the spacious backyard leading to a large open area maintained by the association. The neighborhood is completed by a playground as well as tennis courts and walking trails. What more could you ask for in a house and its community?! Make an appointment to come see this home as it won't last very long in this competitive market!

2119 Serenity Lane, 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

2701 Woodworth Avenue, Woodstock
$540,000
5 Beds ⋅ 4 Baths ⋅ 12653446 MLS ⋅ CLOSED Status
Welcome to 2701 Woodworth Avenue, an exceptional original-owner residence offering 5 bedrooms, 3.5 baths, a 3-car garage, and beautifully finished living space designed for both everyday comfort and elevated entertaining. Perfectly positioned on a premium corner lot in one of Woodstock's most desirable neighborhoods, this meticulously maintained home showcases quality craftsmanship and thoughtful upgrades throughout. A dramatic two-story entry welcomes you inside, where soaring ceilings, abundant natural light, and elegant finishes create an immediate sense of sophistication. The vaulted living and dining rooms provide an impressive space for hosting, while the open-concept design seamlessly connects the main living areas. The stunning chef's kitchen serves as the heart of the home, featuring custom cabinetry, quartz countertops, a large center island, stainless steel appliances, subway tile backsplash, double wall ovens, and generous workspace ideal for entertaining and everyday living. The kitchen flows effortlessly into the spacious family room highlighted by a beautiful fireplace and custom wood accent wall. Retreat to the expansive primary suite featuring tray ceilings, oversized windows, and a luxurious spa-inspired bath complete with dual vanities, a soaking tub, separate shower, and abundant space to unwind. Four additional bedrooms provide flexibility for family, guests, home offices, or multigenerational living. The professionally finished basement elevates this home to another level, offering a spacious recreation room, custom wet bar, dedicated fitness area, and multiple spaces designed for entertaining, relaxing, and gathering with friends and family. Step outside to discover a truly remarkable backyard oasis. Designed for unforgettable outdoor living, the custom paver patio features extensive hardscaping, a built-in fire pit, seating walls, outdoor dining space, and an impressive covered pavilion that creates the perfect setting for entertaining in every season. The fully fenced yard offers privacy while maintaining an open and inviting feel. Additional highlights include 9-foot ceilings, extensive updates throughout, professional landscaping, exceptional curb appeal, and pride of ownership that is evident at every turn. Located just minutes from schools, shopping, dining, parks, and commuter routes, with the middle school conveniently located just down the street, this rare offering combines luxury, functionality, and lifestyle in one extraordinary package.

2701 Woodworth Avenue, 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

863 Pleasant Street, Woodstock
$270,000
5 Beds ⋅ 3 Baths ⋅ 12624264 MLS ⋅ CLOSED Status
This bi-level home offers genuine potential in Woodstock. With five bedrooms and three bathrooms, the layout provides flexibility for residents, remote workers, or investors exploring rental opportunities. The structure and lot size create a solid foundation for buyers ready to personalize the space. Positioned in an established area, this property presents an opportunity to build equity through thoughtful updates. The multi-level design maximizes usable space, and the bedroom-and-bath configuration supports diverse living arrangements. Whether you're seeking a long-term owner-occupied home or evaluating investment potential, the bones are here to work with. Schedule your showing today and explore what this property can become with your vision

863 Pleasant Street, Woodstock

4218 Billingsgate Lane, Woodstock
$655,000
5 Beds ⋅ 5 Baths ⋅ 12620458 MLS ⋅ CLOSED Status
If you are looking for perfection then your search is over !!! This amazing 5 Br / 5 bath home has been completely redone and is ready for all your new memories. This beautiful Kitchen offers upgraded Maple Cabs, under cabinet lighting and custom back splash. Sliding doors lead to a huge 40 x 14 deck that looks over your amazing well groomed 3 acre lot .The living room has custom built entertainment center, hardwood floor & crown molding. The dining room has hardwood floor, crown molding, chair-rail and an atrium door leading to a beautiful sun room w/cathedral ceilings & access to the deck and back yard. The family room has Brick fireplace w/ gas starter, hardwood floors. The 1st floor bedroom has custom built-ins, hardwood floor, and can serve as a perfect guest bedroom, office or den w/access to the adjacent full bath. Other features of the home are 2nd floor laundry, MBR bath w/ whirlpool tub, separate shower & double bowl sinks. A finished basement w/Rec room, bonus/playroom, bath LV flooring in the finished area. Tons of closets, extra storage plus a work room most dream of. If that's not enough a GREAT 36x24 barn that offers 2 horse stalls, large open area that can be used for man/lady cave, or the hobby farm you always dreamed of .. included are 2 stall (10x8) horse barn, w/3/4 concrete floor, water & elect. It truly doesn't get better than this!! This is your chance to have your dream home and your piece of paradise.. RARE AND THIS WONT LAST !!

4218 Billingsgate Lane, Woodstock

937 Wicker Street, Woodstock
$343,000
5 Beds ⋅ 2 Baths ⋅ 12622078 MLS ⋅ CLOSED Status
Well-maintained 5-bedroom, 1.5 bath home set on a spacious 0.35-acre lot with a large, fully fenced backyard-perfect for entertaining, pets, or relaxing in your own private outdoor space. The yard features mature trees, plenty of green space, and an above-ground pool ready for summer enjoyment. The home offers a functional and flexible layout with two bedrooms and a full bath conveniently located on the main floor. Upstairs includes three additional bedrooms and a half bath, providing ample space. Inside, you'll find hardwood floors throughout and a bright, comfortable living area. The enclosed porch creates a great transition space between the home and the attached 2-car garage-ideal for most seasons. Additional highlights include a full basement offering excellent storage or future finishing potential, plus major exterior updates with roof and siding both under 10 years old. With its generous lot, practical layout, and inviting outdoor space, this property is a great opportunity to own a move-in-ready home with room to grow!

937 Wicker Street, Woodstock

301 Tanager Drive, Woodstock
$424,500
5 Beds ⋅ 4 Baths ⋅ 12596561 MLS ⋅ CLOSED Status
Are you looking for 5 bedrooms? This home features 5 bedroooms, 3 1/2 bathrooms, a finished basement and a pool. What more can you ask for. Garage space? Yes, we have it 20 X 40 which equates to a tandem 4 car garage! The living room has wood burning fireplace with a gas starter. The finished basement has a "Heat N Glo" gas fireplace. In 2005 an addition was added to the home adding the additional bed rooms along with a bonus room (which can be a tv room, playroom or nursery) and attic staired attic access. The master bedroom features a master bath with a soaker tub, separate shower and a newer vanity. In the kitchen there is room for a table, counter seating and an island. In the summer enjoy the above ground pool and pool (17 X 9) pool deck or the lovely gardens. The basement is finished and features the laundry room, pantry closet, additional storage and a kitchen with beautiful cabinetry! Ceramic tile floors and a full bathroom. There is so much more to this home, come see it!

301 Tanager Drive, Woodstock

2741 Haydn Street, Woodstock
$455,000
5 Beds ⋅ 3 Baths ⋅ 12575526 MLS ⋅ CLOSED Status
Welcome to 2741 Haydn St., Woodstock - a spacious and beautifully designed two-story home offering 3,344 sq. ft. of comfortable living space! This impressive 5-bedroom, 2.5-bath home features a bright open floor concept perfect for modern living and entertaining. The main level showcases a generous living area that flows seamlessly into the kitchen, complete with stainless steel appliances, a breakfast bar, and a separate eating area - ideal for gatherings of any size. Upstairs, you'll find all five spacious bedrooms plus a versatile loft area, providing flexible space for a home office, playroom, or additional lounge area. The massive primary suite is a true retreat, featuring a private bath with a separate shower and soaking tub. The full unfinished basement offers endless possibilities for future finishing or abundant storage space. Step outside to enjoy the expansive yard - perfect for outdoor entertaining, gardening, or relaxing evenings at home. A 2-car garage provides added convenience and additional storage. With its thoughtful layout, spacious bedrooms, and room to grow, this home is ready to meet your needs. Schedule your private showing today!.

2741 Haydn Street, Woodstock

419 Dean Street, Woodstock
$390,000
5 Beds ⋅ 2 Baths ⋅ 12536404 MLS ⋅ CLOSED Status
Step into timeless charm with this beautifully maintained 1910 farmhouse, where historic character meets modern convenience. Original woodwork and lead glass windows grace the interiors, highlighting the craftsmanship of a bygone era, while five generous bedrooms (4 with walk in closets!) and two full baths provide ample space for family and guests. The remodeled kitchen and baths blend style and functionality, complemented by newer windows (2015 first floor and 2021 second), sewer line, and roof for worry-free living. Outdoor spaces invite relaxation and entertaining, with covered front and back porches and a stamped concrete patio perfect for gatherings. Watch sunsets from your front porch swing! A heated two-car garage adds year-round comfort and practicality. This home is a rare opportunity to enjoy classic farmhouse appeal with thoughtful updates designed for today's lifestyle. This one won't last - make it first on your list before its gone!

419 Dean Street, Woodstock

2441 Haydn Street, Woodstock
$427,000
5 Beds ⋅ 4 Baths ⋅ 12494631 MLS ⋅ CLOSED Status
Welcome to 2441 Haydn Street, a home that offers space, comfort, and an unbeatable location in one of Woodstock's most convenient neighborhoods. With a PARK-LIKE YARD, an OVERSIZED LOT, and the neighborhood PARK ACROSS THE STREET, this property delivers the everyday lifestyle so many buyers are searching for. Inside, this home features an impressive amount of usable living space - perfect for families, multi-purpose living, work-from-home setups, or anyone who needs rooms that flex with life. All FIVE bedrooms are located upstairs, paired with three full bathrooms on the second level, making mornings and routines seamless for everyone. Need a sixth bedroom? A potential first-floor bedroom offers even more flexibility for guests, in-laws, or an office. This home makes everyday living and entertaining a breeze. From the kitchen to the family room to the backyard, everything connects effortlessly. And speaking of the backyard - it's truly something special. The HUGE lot gives you a park-like setting of your own, complete with a beautiful patio and a cozy fire pit, perfect for barbecues, summer nights, and fall s'mores under the stars. Additional highlights include: * 3.5 bathrooms * First-floor laundry * Versatile rooms ideal for offices, playrooms, crafting, gaming, extended closets, or storage * 3-car garage with generous parking and storage * New roof (2021) * New hot water heater (2026) * Fresh paint throughout Located minutes from top-rated schools, walking trails, parks, and just a hop, skip, and a jump from the Woodstock Square, this home provides incredible convenience in a community setting people love. Enjoy the ease of being close to town while still having the privacy and space of an oversized suburban lot.

2441 Haydn Street, Woodstock

339 Meadowsedge Drive, Woodstock
$430,000
5 Beds ⋅ 4 Baths ⋅ 12500588 MLS ⋅ CLOSED Status
Discover your dream home in the heart of Apple Creek Estates, a stunning 2-story residence lovingly maintained by its original owners. Recent updates include a NEW roof and gutters, fresh paint throughout the home, and NEW granite countertops and sink in the kitchen. This expansive 5-bedroom, 3.1-bathroom home is freshly painted and has new granite countertops in the kitchen. The home offers versatile living spaces, including a first-floor bedroom with an attached full bathroom, perfect as a guest suite or private home office. The breathtaking 2-story family room is flooded with natural light, creating a warm and inviting atmosphere, while the large kitchen is a delight with ample cabinetry and counter space. Elegant hardwood flooring flows throughout, adding timeless sophistication. Upstairs, the primary bedroom is a true retreat, featuring a massive walk-in closet and a luxurious ensuite bathroom with double sinks, a separate shower, and a relaxing soaker tub. Convenience is key with a spacious second-floor laundry room. The full unfinished basement awaits your creative vision, whether you envision a home theater, gym, or additional living space. Ideally located near the park and within walking distance to Prairiewood Elementary and Creekside Middle Schools, this home perfectly blends style, functionality, and an unbeatable location. Don't miss the chance to make this Apple Creek Estates gem your forever home!

339 Meadowsedge Drive, Woodstock

1721 Yasgur Drive, Woodstock
$315,000
5 Beds ⋅ 3 Baths ⋅ 12500424 MLS ⋅ CLOSED Status
Large 5 bed 2 1/2 bath home in the Sweetwater subdivision!! Spacious Open floor plan with huge living room, large Kitchen with center island, 42" cabinets and spacious pantry. Main floor Flex room, perfect space for office or Den! 5 Bedrooms all on the 2nd floor, 2nd floor loft was converted to 5th bedroom (no closet), convenient 2nd floor laundry room, large Primary Bedroom Suite with spacious walk-in closet. Seller started renovation project of expanding primary bedroom's full bath, great potential for added space! Full unfinished basement perfect for future living space if needed!! Large, fenced yard with 27'x16' deck with pergola, separate fenced side yard for dog run, 100-gallon pond with waterfall, home to 4 large Giant Goldfish, 2 Koi and a handful of red tail minnows!! House does need work, price reflects condition... great opportunity for sweat equity! Property being sold As-Is.

1721 Yasgur Drive, Woodstock

324 N Madison Street, Woodstock
$250,000
5 Beds ⋅ 1 Baths ⋅ 12490881 MLS ⋅ CLOSED Status
Step back in time with this beautifully preserved piece of Woodstock history! Built in 1902, this 5-bedroom, 1-bath home is among the earliest in town and proudly holds historical status. The residence showcases timeless craftsmanship with original woodwork, hardwood floors, pocket doors, built-in cabinetry, and a striking tin ceiling. Modern comforts include a newer furnace, A/C, and water heater. Relax on the inviting front porch with its stunning street-facing windows, or enjoy outdoor living on the spacious deck overlooking the large lot. Plenty of closet space and potential to add an additional bath and laundry upstairs. Ideally located near the charming Woodstock Square, METRA, dining, and shopping!

324 N Madison Street, Woodstock

12915 Pleasant Valley Road, Woodstock
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 12466861 MLS ⋅ CLOSED Status
Beautiful custom home where quality is evident in every detail. 7.49 acre natural woodlands and prairie grass estate located just east of MCCD Pleasant Valley Recreation Area. Huge front porch offers warm welcome to the extraordinary quality & detail in this 3700sqft 5 bed 3 bath GreatRoom style open plan home, a huge sundrenched white island kitchen with 3 ovens features soap stone counters, the adjacent gathering room enjoys a custom woodburning stone fireplace and offers access to the vaulted screen porch and sunny party deck. 2 additional flex rooms, a large dining room and convenient full bath, laundry and large mudroom all on the main floor. 4 beds up, full unfinished basement with full bath rough, huge bonus room over the 3 car garage has private access. The original timber frame barn has been exactingly restored with new concrete foundation & floor, steel siding & roof along with new windows for the next hundred plus years! Enormous organic garden plot and trails through acres of pristine naturalized woodland and native prairie plantings which offers significant property tax savings annually through the state's Conservation Stewardship Program. Generac backup generator and owned solar panels for safety, security and savings! This beautiful home is truly move-in ready.

12915 Pleasant Valley Road, Woodstock



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