Woodstock Homes under $750,000

Welcome to Woodstock, Illinois – a charming city nestled in the heart of McHenry County, where history meets modern living. Known for its picturesque downtown, Woodstock is a delightful blend of small-town charm and vibrant community spirit. With its iconic square, featuring historic buildings and quaint shops, residents and visitors alike can enjoy a variety of local eateries, boutiques, and seasonal festivals that bring the community together.

Woodstock is not just about its rich history; it also boasts beautiful parks, scenic walking trails, and ample recreational opportunities, making it an ideal place for families and outdoor enthusiasts. The city’s commitment to preserving green spaces ensures that residents can enjoy nature right at their doorstep. Additionally, Woodstock is conveniently located just a short drive from Chicago, providing easy access to the bustling city while maintaining the tranquility of suburban living.

For those looking to make Woodstock their home, you’ll be pleased to discover a range of stunning properties available for under $750,000. From charming single-family homes with character to modern townhouses with all the amenities, there’s something for everyone. Whether you’re a first-time buyer or looking to upgrade, Woodstock offers diverse housing options that cater to various lifestyles and budgets.

Experience the warmth and community spirit of Woodstock, where you can find your dream home in a city that truly has it all. Embrace the opportunity to live in a place that balances history, nature, and modern conveniences—welcome home!

Newest Woodstock Homes under $750,000

$275,000

3 Beds ⋅ 2 Baths ⋅ 12790775 MLS ⋅ NEW Status

Charm and character of this early 1900s home, where historic appeal meets modern updates! This inviting 3-bedroom, 2-full-bath home offers numerous improvements throughout, including a beautifully updated kitchen, recently updated bathrooms, newer flooring, updated windows, a newer roof, and recently painted exterior. Original hardwood floors in the main living room and dining room add warmth and timeless character, while the bedrooms offer plenty of storage space. The unfinished walkout basement offers additional storage and future possibilities, including a separate unfinished bonus room with potential for a home office, hobby room, or flex space. Step outside from the basement to a cozy screened-in porch, perfect for enjoying a little fresh air. A detached 2-car garage provides additional parking and storage. Conveniently located just steps from the Historic Woodstock Square and Metra train station, you'll enjoy easy access to local shops, restaurants, entertainment, the farmers market, and all the charm that downtown Woodstock has to offer. Don't miss your opportunity to own a piece of Woodstock's history with the modern conveniences you've been looking for!

349 Vine Street, Woodstock

$739,000

3 Beds ⋅ 3 Baths ⋅ 12777101 MLS ⋅ NEW Status

Contemporary 2 story on 5 fenced acres. Located on the Bull Valley riding trail with direct access. Membership required. Gourmet kitchen with Wolf range, large island with prep sink, cherry cabinets and butlers pantry. 2 bedrooms with walk in closets and Jack and Jill bathroom.Walkout basement with roughed plumbing. New roof 2025. Full walkout basement with roughed plumbing for a future bath. Additional storage above the garage.

8702 Mason Hill Road, Woodstock

$429,490

4 Beds ⋅ 3 Baths ⋅ 12795347 MLS ⋅ NEW Status

* SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FALL DELIVERY! * Homesite#0266 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 OCEANSIDE siding with Graystone 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.

3803 Riverwoods Drive, Woodstock

$444,750

4 Beds ⋅ 3 Baths ⋅ 12795288 MLS ⋅ NEW Status

** 3 CAR GARAGE! * SPECIAL INCENTIVES AVAILABLE! * FALL DELIVERY! HOMESITE # 0249 Take in the beauty of the Townsend, a home where sophisticated design and everyday comfort come together seamlessly. This thoughtfully crafted residence features four bedrooms, two full bathrooms, a powder room, and a spacious living room, providing ample space for both relaxation and entertainment. The first floor boasts an airy, open-concept layout, with luxury vinyl plank flooring unifying the kitchen, dining area, and family room. At the heart of the home, the chef-inspired kitchen impresses with sleek quartz countertops, premium stainless-steel appliances, 42"" cabinetry in your choice of finishes, and a large center island perfect for meal prep and gatherings. Upstairs, the owner's suite is a paradise, offering a spacious walk-in closet and a spa-like en-suite bathroom with double sinks and a deluxe shower, creating the perfect space for unwinding. Three additional bedrooms and a full bathroom are located nearby, while a second-floor laundry room adds convenience to everyday living. With its smart design and premium finishes, the Townsend offers a lifestyle that blends comfort, style, and functionality, perfectly suited for the way you live today. Exterior will be ASPEN WHITE color siding with Ripley stone color brick. (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.

3828 Meadowridge Drive, Woodstock

$474,900

4 Beds ⋅ 4 Baths ⋅ 12794927 MLS ⋅ NEW Status

This impressive 4-bedroom, 3.5-bath home offers approximately 3,081 square feet of above-grade living space, plus an additional 2,000 square feet in the partially finished basement, combining generous room sizes with distinctive custom craftsmanship throughout. A highly desirable feature of this home is the convenient main-level layout, offering 3 bedrooms and a full bathroom on the first floor. From the moment you enter, you'll appreciate the beautiful oak flooring, solid oak trim and doors, and elegant oak staircase. The spacious kitchen features granite countertops, oak cabinetry, a center cooking island, breakfast bar, built-in desk, charming bay window, and a generous eat-in area. Two sliding glass doors lead to an expansive deck with a dedicated gas line for grilling, creating a wonderful setting for outdoor entertaining. The stunning family room is a true highlight, featuring a soaring cathedral ceiling finished in knotty tongue-and-groove cedar, a beautiful brick fireplace with an oak mantel, and direct access to the deck. Custom Andersen windows throughout fill the home with natural light. The primary suite offers a spacious walk-in closet and a private bathroom complete with a jetted tub, separate shower, double vanity, and linen closet. All bathrooms feature tile finishes and Kohler fixtures. A generously sized main-level laundry room adds everyday convenience. The partially finished basement offers incredible additional space, featuring a built-in oak wet bar, along with plenty of room for storage, recreation, or future customization. With over 5,000 square feet of combined above-grade and basement space, beautiful custom woodwork, generous entertaining areas, and plenty of possibilities to make it your own, this home is ready for its next chapter. Schedule your showing and discover everything it has to offer!

1341 Portage Lane, 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

$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

2020 Olmstead Drive Unit #2020, Woodstock

$295,000

2 Beds ⋅ 2 Baths ⋅ 12783385 MLS ⋅ ACTIVE 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 ⋅ ACTIVE 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 ⋅ ACTIVE 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 ⋅ ACTIVE 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!

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Woodstock Homes under $750,000

Newest Woodstock Homes under $750,000

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