Woodstock Homes under $400,000

Welcome to Woodstock, Illinois—a charming city nestled in the heart of McHenry County, where small-town charm meets modern convenience. Known for its vibrant downtown area, historic architecture, and a strong sense of community, Woodstock is the perfect place for families, young professionals, and retirees alike to call home. With its picturesque parks, local shops, and delicious dining options, residents enjoy a lifestyle that seamlessly blends leisure and activity.

One of the standout features of Woodstock is its commitment to preserving history while embracing progress. The iconic Woodstock Square, with its beautifully restored Victorian buildings, serves as a hub for cultural events, seasonal festivals, and a lively farmers' market. The city’s rich artistic scene is also highlighted by the Woodstock Opera House, where you can catch a variety of performances throughout the year.

For those seeking their dream home, Woodstock offers a fantastic selection of properties under $400,000. Whether you’re looking for a cozy single-family home, a charming townhouse, or a spacious condo, there are options to suit every taste and budget. These homes often feature modern amenities, well-maintained yards, and access to excellent schools, making them ideal for families looking to settle down.

With its friendly atmosphere, excellent recreational opportunities, and a strong sense of community, Woodstock, Illinois, is a hidden gem that offers an exceptional quality of life. Discover your perfect home in this delightful city today and become part of a community that truly feels like family!

Newest Woodstock Homes under $400,000

$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

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

$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

$357,990

3 Beds ⋅ 3 Baths ⋅ 12789982 MLS ⋅ ACTIVE Status ⋅ Riverwoods BLDG.

AVAILABLE SPRING 2027! SPECIAL FINANCING OFFERS AVAILABLE! Homesite #4201 Step inside and explore the Charlotte, a highly sought-after two-story duplex featuring three bedrooms and 2.5 baths. The first floor showcases an open-floor plan, creating a sense of spaciousness and unity that seamlessly blends entertainment and everyday comfort. It's easy to see why the kitchen is considered the heart of this home-complete with stainless steel appliances, and a stunning oversized quartz island, this space leaves nothing to be desired. Better still, the kitchen flows effortlessly into a generous great room and dining area, making it ideal for hosting gatherings and special events. Upstairs, retreat to the luxurious owner's suite, offering a spacious walk-in closet and a spa-inspired bath. Two more generously sized bedrooms, an additional bathroom, and a convenient laundry room round out the upper level. High-end finishes include luxury vinyl plank flooring, sleek quartz countertops, and elegant decorative railings, all enhancing the home's aesthetic appeal. 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.

Woodstock

$389,000

3 Beds ⋅ 3 Baths ⋅ 12789375 MLS ⋅ ACTIVE Status

Welcome to this modern, move-in-ready home in the desirable Apple Creek subdivision of Woodstock, perfectly situated on a beautiful corner lot with a fenced backyard. The comfortable floor plan features a formal living room and dining room, while the open kitchen flows into an impressive two-story family room highlighted by a brick fireplace. Upstairs you'll find three bedrooms plus a versatile loft. The primary suite features a vaulted ceiling, sitting room, and private bath with double vanity, whirlpool tub, and separate shower. The home has been freshly painted and features brand-new carpet throughout the first floor, stairs, and upstairs landing. Additional improvements include a new roof and siding in 2021, furnace replaced in 2017, newer water heater, vinyl windows, sump pump and flood control. The full basement offers additional flexible living or recreation space and is already roughed in for a future bathroom. Enjoy the fenced backyard, neighborhood ponds, nearby community park, and schools located within the Apple Creek community. Approximately 1.5 miles from historic Woodstock Square and the Woodstock Metra station, with a convenient south Woodstock location for commuters. A great combination of updates, location, and neighborhood amenities, ready for its next owner!

193 Bloomfield Drive, Woodstock

$399,900

3 Beds ⋅ 4 Baths ⋅ 12787397 MLS ⋅ ACTIVE Status

Welcome Home to 10306 Saddlebred Trail! This ranch-style home is situated on approximately 1.03 acres and features 4 bedrooms/2.2 bathrooms and an attached 2 car garage! Property is Sold AS-IS. Equal Housing Opportunity.

10306 Saddlebred Trail, Woodstock

$290,000

4 Beds ⋅ 2 Baths ⋅ 12770520 MLS ⋅ ACTIVE Status

Welcome home to this charming Cape Cod perfectly situated on a beautiful, tree-lined street just blocks from the vibrant Woodstock Square. Boasting classic architectural character like an arched doorway leading into the cozy family room with a wood-burning fireplace, this home offers warm and inviting living spaces throughout. Inside, you will find 4 spacious bedrooms-including 2 convenient main-floor bedrooms and 2 upstairs-along with 2 full bathrooms. Original hardwood floors sit beneath the first-floor carpet, waiting to be showcased! The layout includes a large eat-in kitchen ideal for casual dining, plentiful storage solutions throughout, and a finished basement providing great additional living or recreational space. Step outside from the family room onto your private side balcony, or relax on the deck in the fully fenced yard. Close to the Metra, parks and shopping. Selling AS-IS.

804 Roosevelt Road, Woodstock

$137,500

1 Beds ⋅ 1 Baths ⋅ 12783458 MLS ⋅ ACTIVE 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

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Woodstock Homes under $400,000

Newest Woodstock Homes under $400,000

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