Woodstock Real Estate

Welcome to Woodstock, Illinois – a charming city that beautifully blends small-town charm with modern conveniences. Nestled in McHenry County, Woodstock is renowned for its picturesque landscapes, vibrant arts scene, and rich history, making it a perfect place to call home.

Established in the mid-1800s, Woodstock has preserved its historic character while embracing growth and development. The city is perhaps best known for its stunning Victorian architecture, particularly the iconic Woodstock Opera House, which serves as a cultural hub for the community. With a calendar full of events, from art fairs to live performances, residents enjoy a lively atmosphere that fosters creativity and connection.

Nature enthusiasts will appreciate the abundance of parks and outdoor recreational areas that Woodstock has to offer. The scenic Woodstock Square is a delightful spot to relax, shop at local boutiques, or enjoy a meal at one of the many charming restaurants. Additionally, the nearby Chain O’Lakes State Park provides ample opportunities for boating, fishing, and hiking, ensuring that outdoor adventures are just a stone's throw away.

Families will find Woodstock to be an inviting community with excellent schools, safe neighborhoods, and a strong sense of belonging. The city's commitment to preserving its heritage while promoting a progressive environment creates a unique blend that appeals to all ages.

With easy access to major highways and a commuter-friendly Metra train station, Woodstock provides the perfect balance of tranquility and convenience. Explore the enchanting streets of Woodstock and discover why this vibrant city is truly a hidden gem in McHenry County!

Newest Listings in Woodstock

$300,000

3 Beds ⋅ 2 Baths ⋅ 12781485 MLS ⋅ NEW Status

Looking for a charming farmhouse with room for your horses? Situated on more than 2 acres,with A-1 zoning, this property offers country living with plenty of possibilities! A three-stall barn features space for tack, a hay loft and multiple fenced paddocks, making it an ideal setting for horse enthusiasts. Inside, you'll find a spacious family room with a cozy brick fireplace, a roomy kitchen, a separate dining room and a comfortable living room. Upstairs, three generously sized bedrooms provide plenty of space to unwind. Step outside onto the deck and enjoy the peaceful surroundings, mature trees and natural beauty of the property. With so much potential both inside and out, this farmhouse is ready for your vision and personal touches. Bring your tools, your creativity and your dreams of country living!

3017 Country Club Road, Woodstock

$132,000

1 Beds ⋅ 1 Baths ⋅ 12794512 MLS ⋅ NEW Status

Welcome to this inviting one-bedroom condo in Woodstock, located within Woodstock Community Unit School District 200! The open-concept layout offers a comfortable living area with access to a private balcony. The kitchen features ample cabinet and counter space, a breakfast bar, and a pantry closet. The bedroom includes a walk-in closet and convenient access to the full bath. In-unit laundry adds to the ease of everyday living. Relax on your private balcony overlooking beautifully landscaped common areas. Enjoy a convenient location close to shopping, restaurants, parks, golf courses, and major highways! A wonderful opportunity to enjoy comfortable, low-maintenance living in a convenient location!

551 Leah Lane Unit #3C, Woodstock

$299,900

12794405 MLS ⋅ NEW Status

8403 Mason Hill Road, 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

$329,900

3 Beds ⋅ 3 Baths ⋅ 12793015 MLS ⋅ NEW Status

Turnkey and move-in ready! This beautifully maintained 3-bedroom, 2.5-bath raised ranch offers the perfect combination of comfort, style, and convenience. Ideally located just minutes from the historic Woodstock Square and all the shopping, dining, and conveniences along the Route 47 corridor, this home is ready to impress. Recent updates include a BRAND NEW ROOF, NEW DECK, and NEW CARPET AND FLOORNG throughout, giving you peace of mind from day one. The updated kitchen features NEWER STAINLESS STEEL APPLIANCES and ample cabinet space, making it perfect for everyday living and entertaining. Step outside to a fully fenced backyard complete with a storage shed, offering plenty of room for pets, play, or outdoor gatherings. The attached garage includes an oversized storage room that would make an excellent workshop or hobby space. Conveniently located near schools, parks, and all that Woodstock has to offer, this is the one you've been waiting for. PRICED TO SELL- COME AND GET IT!

558 Barbary Lane, Woodstock

$429,000

4 Beds ⋅ 3 Baths ⋅ 12792589 MLS ⋅ NEW Status

Beautiful 4 bed, 2.5 bath home with a 3-car attached garage that sits at the end of a cul-de-sac and has sought after waterfront views overlooking a large pond. The main level features hardwood floors, fresh paint and carpet throughout, a spacious family room with fireplace, formal living and dining areas, a dedicated home office, and a large kitchen with center island, stainless steel appliances, and breakfast area overlooking the pond. Upstairs offers four bedrooms with new carpet, including a spacious primary suite with an en suite bathroom and walk-in closet, plus convenient second-floor laundry. This home is not only in the sought-after Sonata subdivision, but on one of the best lots as well. Don't miss this rare opportunity to call this property home!

831 Bach Court, Woodstock

2020 Olmstead Drive Unit #2020, Woodstock

$295,000

2 Beds ⋅ 2 Baths ⋅ 12783385 MLS ⋅ NEW Status

Welcome to this highly desirable Canterbury ranch-style quad unit in the sought-after Maples on Olmstead community! Offering the ease and convenience of single-level living, this spacious 2-bedroom home features a versatile den that could easily serve as a 3rd bedroom, home office, or additional living space. The inviting open floor plan showcases beautiful vinyl wood flooring throughout, a cozy gas-log fireplace, and a gorgeous sunroom filled with natural light-an ideal space to relax or entertain. Enjoy the convenience of an in-unit laundry room, spacious 2-car garage, and open green space at the front entrance of the home. Updates and improvements include a newer furnace and central air conditioning (approximately 2 years old), roof (2021), water heater (approximately 5 years old), dishwasher (2022), dryer (2023) and refrigerator (2024). All appliances are included! Association fees cover exterior building maintenance, landscaping, and snow removal, making everyday living that much easier. Beautiful clubhouse available for residences that includes exercise room, pool table, library and kitchen for additional entertaining needs. Whether you're looking to downsize or simply enjoy the comfort of ranch-style living, this home offers a wonderful combination of space, functionality, and low-maintenance living in a desirable community.

2020 Olmstead Drive Unit #2020, Woodstock

$400,000

2 Beds ⋅ 2 Baths ⋅ 12781684 MLS ⋅ NEW Status

STUNNING, LOCATION and FLOOR PLAN all the things you are looking for. This beautiful ranch style townhome is in excellent condition. Nestled in the Villas of Bull Valley this home gives you a peaceful community with maintenance free living. 9' ceilings, stunning gas fireplace, plantain shutters, brand new hardwood flooring throughout, full basement plumbed for additional bath are just a few of the amenities. The open floor plan offers a split two bedroom and additional office. Custom kitchen has upgraded stainless steel appliances, custom lighting, island, abundant 42' cabinets for storage and closet pantry. The finished garage has epoxy flooring. Truly a turn key home that allows you immediate occupancy for the holidays.

1306 Boulder Court, Woodstock

$449,990

4 Beds ⋅ 3 Baths ⋅ 12790974 MLS ⋅ NEW Status

3 CAR GARAGE * SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FALL DELIVERY! Homesite#244 Discover the Wren, a thoughtfully designed two-story home that blends modern comfort with everyday functionality. This layout features four spacious bedrooms, two full bathrooms, and a convenient study on the main floor. The open-concept design connects the kitchen, dining area, and family room, creating a seamless flow that's ideal for both relaxed living and entertaining. Luxury vinyl plank flooring extends throughout this main living space, adding warmth and durability. A charming, covered porch creates a warm and welcoming entry, setting the tone for what's inside. The kitchen is well-appointed with a large center island, quartz countertops, stainless steel appliances, and ample cabinetry for storage and organization. A versatile flex room on the first floor adds extra space for a home office, playroom, or quiet retreat-tailored to fit your lifestyle. Upstairs, the private owner's suite offers a generous walk-in closet, and an en-suite bathroom designed for comfort. Three additional bedrooms and a full bathroom provide flexible options for family, guests, or hobbies. A second-floor laundry room adds convenience, while a two-car garage and thoughtful interior design details enhance daily living. The Wren delivers a smart, stylish layout designed to support the rhythms of modern life. Exterior will be slate Aspen White siding with Old World Ledge - Coastal Brown color stone. (pic for reference ONLY). There is currently no active SSA at this community. *Photos are not this actual home* At the heart of a warm, welcoming community, this thoughtfully designed neighborhood offers the perfect blend of modern living and historic charm. Surrounded by peaceful streets and open green spaces, residents can enjoy walkable pathways, cozy cul-de-sacs, and the comfort of a tight-knit atmosphere. Just minutes away, downtown Woodstock invites you to explore its vibrant mix of antique shops, local dining favorites, and year-round community events. Steeped in rich history and hometown pride, the area buzzes with activity - from seasonal farmers' markets and summer concerts in the square to art fairs and holiday parades. Nature lovers and active families will appreciate the abundance of nearby parks and recreation centers, offering everything from playgrounds to walking trails. Whether you're grabbing coffee in a charming local cafe or enjoying a weekend stroll through beautiful green spaces, Woodstock offers something for everyone - with a lifestyle that feels both timeless and modern.

3800 Meadowridge Road, Woodstock

$175,000

2 Beds ⋅ 2 Baths ⋅ 12790517 MLS ⋅ NEW Status ⋅ Greenwood Circle BLDG.

Easy Living in a Great Woodstock Location! Welcome to this well-maintained 2-bedroom, 1.5-bath condo offering comfort, convenience, and a location close to everything! Step inside to a spacious and inviting living room featuring newer vinyl plank flooring that flows throughout the main level. With plenty of room to relax and unwind, this comfortable living space is perfect for quiet evenings at home or entertaining guests. A conveniently located utility closet houses the newer water heater and furnace. The fully equipped kitchen opens to the dining area, creating a welcoming space for everyday meals and gathering with friends. Just off the dining area, a sliding glass door leads to a private patio, perfect for summer grilling, outdoor dining, or simply enjoying a little fresh air. A convenient half bath and easy access to the attached 1.5-car garage complete the main level. Upstairs, you'll find a generously sized primary bedroom with ample closet space, along with a spacious second bedroom offering flexibility for guests, a home office, or additional living needs. A full bathroom and the convenience of second-floor laundry make everyday living that much easier! Location, location, location! Just minutes from charming downtown Woodstock, shopping, dining, schools, and convenient access to Route 47, this condo puts everyday necessities within easy reach. Whether you're purchasing your first home, looking to downsize, or simply seeking the ease of condo living, this well-cared-for home offers a wonderful opportunity to make it your own. Comfortable, convenient, and easy to maintain - welcome home!

Woodstock

$199,900

5 Beds ⋅ 2 Baths ⋅ 12786068 MLS ⋅ NEW Status

Opportunity is knocking! Calling all investors and rehabbers to this unique property. This 2 flat in downtown Woodstock is just waiting for some fresh ideas. Some of the work has been started.The electric and duct work for the furnace was done in 2017. Some drywall, wiring and plumbing has been completed as well. The lower level features living room, dining room, kitchen ,2 bedrooms and a newer bathroom. Upstairs there are 7 rooms (3 bedrooms) plus a walkup attic. A 2 car detached garage is also included. New forced air furnace 2018. This property is being sold as is.

422 E Jackson Street, Woodstock

$279,900

4 Beds ⋅ 2 Baths ⋅ 12783920 MLS ⋅ NEW Status

Welcome Home! This cozy home offers comfortable living space, a functional layout, and a convenient location. The main level features 3 bedrooms with hardwood flooring, a living room with hardwood floors, and a kitchen with table space. The finished walkout basement provides additional living space, including a primary bedroom, full bathroom, a family room, and a laundry room. Enjoy the beautifully maintained landscaping and fenced backyard, perfect for outdoor relaxation. An attached 1-car garage adds everyday convenience. Conveniently located near schools, shopping, restaurants, entertainment, the Metra station, and more, this home offers comfort and accessibility. Don't miss this great opportunity!

1746 Walnut Drive, Woodstock

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Woodstock Real Estate

Newest Listings in Woodstock

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