114

Woodstock, IL Homes for Sale under $500,000

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  • /18

    $400,000

    Pending
    • 2 Beds
    • 1 Bath
    • 1,392 Sq Ft

    2046 Deep Cut Rd, Woodstock, IL 60098

    Country living with no neighbors (except McHenry County Conservation Land)!! This aluminum sided ranch has a full English basement that is ready for extra living space. The main floor features some hardwood floors in the 2 bedrooms, a brick fireplace in the living room area, a small kitchen area that needs some updating, one bathroom that needs updating, and a family room area off the kitchen.

    Dennis Drake Century 21 Integra

    2046 Deep Cut Rd, Woodstock, IL 60098
  • /51

    $385,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,725 Sq Ft

    1020 Winslow Ave, Woodstock, IL 60098

    This beautifully updated 1,750-square-foot one-story ranch home offers perfect modern living. The spacious three-bedroom layout features a private master suite complete with a beautifully updated master bathroom. Step inside to find fresh interior paint and stunning hardwood flooring stretching through the main living areas. Cozy new carpet adds warmth to all of the bedrooms. The heart of the

    Josh Brown Berkshire Hathaway HomeServices Starck Real Estate

    1020 Winslow Ave, Woodstock, IL 60098
  • /16

    $310,000

    • Land
    • 2.8 Acres
    • $110,714 per Acre

    0 Il rt 47 Route Unit MRD12677518, Woodstock, IL 60098

    These vacant parcels offer exceptional development potential in a high-traffic commercial corridor. Zoned explicitly for general commercial and retail use, lots are ready for immediate construction. It features direct frontage, ensuring maximum visibility and excellent signage opportunities for any future business. All major municipal utilities, including water, sewer, three-phase electricity,

    Josh Brown Berkshire Hathaway HomeServices Starck Real Estate

    0 Il rt 47 Route Unit MRD12677518, Woodstock, IL 60098
  • /30

    $364,800

    Pending
    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    231 Clover Chase Cir, Woodstock, IL 60098

    A beautiful 3 bedroom ranch that has a nice open floor plan with a vaulted ceiling, a gas log fireplace in the living room, an eat in kitchen with a pantry closet, a breakfast bar and loads of cabinet and counter space.The home is also handicapped ready starting with a concrete wheelchair ramp at the front of the home and another ramp in the garage. There is a convenient first floor laundry and

    Peter Klocek Berkshire Hathaway HomeServices Starck Real Estate

    231 Clover Chase Cir, Woodstock, IL 60098
  • /24

    $434,490

    New Construction $55K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft

    1261 Prairie Ridge Trail, Antioch, IL 60002

    **SPECIAL FINANCING OFFERS AVAILABLE! Homesite #0823 Welcome to the Rutherford - a beautifully crafted single-story home that perfectly blends modern design with everyday functionality. Thoughtfully laid out with three spacious bedrooms and two full bathrooms, this open-concept floor plan is designed to promote effortless flow and comfortable living. At the heart of the home, the stylish kitchen

    Bill Flemming HomeSmart Connect LLC

    1261 Prairie Ridge Trail, Antioch, IL 60002
  • /22

    $260,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,405 Sq Ft

    935 Victoria Dr Unit 935, Woodstock, IL 60098

    Welcome to one of the larger available units in Victorian Village! This spacious 3-bedroom, 2 1/2 bathroom two-story condo offers a wonderful combination of comfort, privacy, and scenic surroundings. Enjoy peaceful pond views from nearly every room. The inviting floor plan features a first-floor primary suite, providing convenient one-level living, while the additional bedrooms offer plenty of

    Rick Bellairs Berkshire Hathaway HomeServices Starck Real Estate

    935 Victoria Dr Unit 935, Woodstock, IL 60098
  • /37

    $365,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,152 Sq Ft

    517 Dean St, Woodstock, IL 60098

    This one has it all. A historic home less than half a mile from the Woodstock Square, Woodstock High School, and Dean St Elementary that blends character, space, and a long list of thoughtful updates. Major improvements are already done, with the roof, furnace, central air, water heater, dryer, refrigerator, and carpet all less than three years old. The first floor bedroom features a private bath

    Adam Guss Berkshire Hathaway HomeServices Starck Real Estate

    517 Dean St, Woodstock, IL 60098
  • /12

    $339,900

    • 3 Beds
    • 1 Bath

    616 S Jefferson St, Woodstock, IL 60098

    Prime Woodstock Investment Opportunity! This 3-unit property offers a fantastic opportunity for investors or owner-occupants. Each unit features a comfortable 1 bedroom, 1 bath layout, offering privacy and functionality for tenants. Long term tenants in place for two of the units. Roof, windows, furnaces, and water heater have been replaced with in the last 10 years. Two car garage and ample

    Arturo Flores eXp Realty

    616 S Jefferson St, Woodstock, IL 60098
  • /40

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,593 Sq Ft

    1004 Golden Ave, Woodstock, IL 60098

    The look of millions for the cost of much less....That's what you get with this Golden opportunity! The first thing you notice while driving down Golden Avenue is the stunning and massive stone mailbox that mirrors the stonework inside your new kitchen and living space. Once you step inside, you'll notice 20 foot ceilings soaring over the gas fireplace framed in by a beautiful stone wall. This

    Rob Morrison Coldwell Banker Realty

    1004 Golden Ave, Woodstock, IL 60098
  • /4

    $295,000

    • Land
    • 0 Sq Ft

    9999 E Calhoun St, Woodstock, IL 60098

    DEVELOPMENT OPPORTUNITY - Zoned B3, Comprehensive Plan is Neighborhood Commercial. Village would like to see this parcel developed. Utilites are to the property. Many great possible uses such as: Retail, Service, Bank, Convenience Store, Day Care, and even RESIDENTIAL above COMMERCIAL! Additional Info. 8473223566

    Brian Coleman Brian Coleman & Associates,Inc

    9999 E Calhoun St, Woodstock, IL 60098
  • /33

    $299,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    422 Stewart Ave, Woodstock, IL 60098

    Built in 1999, this one skips the fixer-upper phase most of the neighborhood is still working through! Two stories, three bedrooms, second-floor laundry: someone already solved the layout for you! Walk, roll, ride, or cruise to the square or the high school. That's not a commute, that's a breath of fresh air! Inside: space built the way people actually live. Living and dining rooms that flow

    Tyler Lewke Keller Williams Success Realty

    422 Stewart Ave, Woodstock, IL 60098
  • /50

    $494,900

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    1341 Portage Ln, Woodstock, IL 60098

    Looking for more space? This house has the space you need and more; Its many custom features will impress you: oak trim doors throughout. Oak banister & railing to 2nd floor. Oak floors in entry, halls, dining room and eating area. The beautiful and spacious kitchen features oak cabinets, a center cooking island, granite countertops, a breakfast bar, built-in desk, a bay window plus a very

    Leticia Valdivia Apreda Real Estate Services

    1341 Portage Ln, Woodstock, IL 60098
  • /14

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    113 Raffel Rd, Woodstock, IL 60098

    Welcome to 113 Raffel Rd! Set on a beautiful 1.12-acre mature wooded lot, this 3-bedroom, 1-bath home offers plenty of space, privacy, and potential to make it your own. Inside you'll find a large kitchen with pantry, separate dining room, and a spacious, light-filled living room. One bedroom is conveniently located on the main level, with two additional bedrooms just a few steps up. The

    vanessa elliott LPT Realty

    113 Raffel Rd, Woodstock, IL 60098
  • /30

    $245,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft

    2307 Aspen Dr, Woodstock, IL 60098

    Welcome to this impeccably maintained half duplex in Applewood subdivision, where pride of ownership is evident from the moment you step inside. The main level features beautiful Amazon cherry-toned waterproof luxury vinyl plank flooring, with matching LVP flooring continuing throughout the upper level for a cohesive, low-maintenance look. The seller has completed numerous upgrades and recently

    Tyler Lewke Keller Williams Success Realty

    2307 Aspen Dr, Woodstock, IL 60098
  • /37

    $249,999

    • 3 Beds
    • 1 Bath
    • 1,064 Sq Ft

    822 N Madison St, Woodstock, IL 60098

    Charming Cape Cod, maybe even English Countryside Cottage just blocks from the historic Woodstock Square, Metra, and downtown shops and dining! This 3 bedroom, 1 bath home sits on an oversized 50 x 223 fenced lot, nearly all of the quarter acre is backyard space with a detached garage and screened porch as the perfect three-season hangout. Inside you'll find a sun-filled living room with hardwood

    Craig Fallico Baird & Warner

    822 N Madison St, Woodstock, IL 60098
  • /26

    $422,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,193 Sq Ft

    Starling Plan at Riverwoods - Single Family, Woodstock, IL 60098

    This two-story home provides modern comfort and ample room to grow. Upon entry is a flex space well-suited for hosting guests, followed by a spacious open layout for seamless living and relaxing. Separate from the downstairs main living area, the second level hosts all four bedrooms to provide great personal space and privacy. The sprawling owner’s suite is a serene haven with a full-sized

    Lennar Builder
    4258 Meadowridge Road St Unit 36950471, Woodstock, IL 60098
  • /21

    $399,490

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,063 Sq Ft

    3822 Meadowridge Rd, Woodstock, IL 60098

    The first level of this two-story home is host to communal spaces, including a flex space off the foyer and an open floorplan shared among the family room, dining room and kitchen. A loft and three bedrooms can be found upstairs, two of which feature walk-in closets.

    Lennar Builder
    3822 Meadowridge Rd, Woodstock, IL 60098
  • /49

    $465,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,662 Sq Ft

    101 Nuthatch Dr, Woodstock, IL 60098

    COMPLETELY TURN-KEY HOME IN RARELY AVAILABLE VICTORIAN COUNTRY SUBDIVISION * NEARLY 2,700 SQ FT OF FINISHED LIVING SPACE * 4 BEDROOMS, 2.5 BATHS WITH OVERSIZED BONUS ROOM * TASTEFULLY RENOVATED WITH THE PERFECT MIX OF TRADITIONAL & MODERN * EVERY SQUARE INCH OF THIS CHARMING HOME HAS BEEN METICULOUSLY REFINISHED INSIDE & OUT * NEW RED OAK HARDWOOD FLOORS ON MAIN FLOOR * FRESHLY PAINTED TOP TO

    Valentino Ranallo CENTURY 21 New Heritage West

    101 Nuthatch Dr, Woodstock, IL 60098
  • /21

    $479,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft

    Brighton Plan at Clublands of Antioch - Horizon Series, Woodstock, IL 60098

    This new single-story home optimizes space and prioritizes ease of living. Arranged at the back of the home is an open-concept layout, featuring a convenient kitchen center island overlooking the living and dining areas. Nearby is the cozy owner’s suite with a private bathroom and spacious walk-in closet, while two bedrooms are located down the hall. An unfinished basement provides room to expand.

    Lennar Builder
    2303 Scenic Dr Unit 37604108, Woodstock, IL 60098
  • /37

    $269,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,125 Sq Ft

    809 Washington St, Woodstock, IL 60098

    RARE OPPORTUNITY! Welcome to 809 Washington Street, a solidly built, meticulously maintained 3-Bedroom, 2-Full-bath Ranch Home with a Full Basement, loaded with features that are becoming increasingly difficult to find. Situated on an expansive HALF-acre lot with a true double-lot feel, this property offers an incredible amount of outdoor space rarely available in this location. Whether you're

    Tammy Parzygnat Home Solutions Real Estate

    809 Washington St, Woodstock, IL 60098
  • /14

    $224,900

    $15K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,125 Sq Ft

    110 N Seminary Ave, Woodstock, IL 60098

    Now Offered at a New Price! This inviting Woodstock home combines classic charm with a convenient location just minutes from the Historic Woodstock Square, Metra, schools, parks, dining, and shopping. Featuring 3 bedrooms, a full basement, and ample parking, this property offers exceptional value for buyers looking to personalize a home in an established neighborhood. Don't miss your

    Christopher Lobrillo Grandview Realty, LLC

    110 N Seminary Ave, Woodstock, IL 60098
  • /31

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,914 Sq Ft

    1400 Savanna Ln, Woodstock, IL 60098

    Distinctive architectural charm meets modern comfort in this brick ranch home! Inviting arched stone entry opens up to warm Brazilian Cherry floors and 11' ceilings. Striking custom millwork with dramatic interior archways add warmth and character. The open-concept layout centers around a impressive floor-to-ceiling stone fireplace with gas logs that connects seamlessly to the dining area and

    Kim McCallister Kruse Berkshire Hathaway HomeServices Starck Real Estate

    1400 Savanna Ln, Woodstock, IL 60098
  • /3

    $331,990

    New Construction $40K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,780 Sq Ft

    4111 Meadowridge Rd, Woodstock, IL 60098

    **HOMESITE # 7002 * SPECIAL INCENTIVES AVAILABLE! FALL DELIVERY! Introducing the Marianne, a newly designed two-story duplex that seamlessly blends comfort and elegance. This model offers three spacious bedrooms, two full baths, a half bath, complete with a two-car garage for added convenience. The first floor features the great room, the focal point of the home, effortlessly flowing into the

    Bill Flemming HomeSmart Connect LLC

    4111 Meadowridge Rd, Woodstock, IL 60098
  • /30

    $240,000

    $10K PRICE DROP Pending
    • 4 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    107 W Melody Ln, Woodstock, IL 60098

    Opportunity awaits in this 4-bedroom, 1.5-bath split-level home in historic Woodstock! Offering an abundance of potential, this property is ready for your vision and personal touches. The spacious floor plan features four generously sized bedrooms, a large living room that opens into the kitchen. Additional highlights include an attached 2-car garage and a fully fenced backyard with plenty of

    Chrissy Newbold RE/MAX Connections II

    107 W Melody Ln, Woodstock, IL 60098
  • /34

    $379,900

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    558 Barbary Ln, Woodstock, IL 60098

    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

    Paul Dimmick Keller Williams Success Realty

    558 Barbary Ln, Woodstock, IL 60098
  • /21

    $356,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,853 Sq Ft

    2334 Heartwood Ln, Woodstock, IL 60098

    This new two-story home is host to an inviting open-concept layout on the first floor to maximize interior space, with a nearby patio offering seamless outdoor entertainment and leisure. Three bedrooms can be found upstairs, including the luxurious owner’s suite at the back of the home, offering access to a spa-inspired bathroom and walk-in closet.

    Lennar Builder
    2334 Heartwood Ln, Woodstock, IL 60098
  • /30

    $242,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,872 Sq Ft

    Unlisted Address

    Opportunities like this don't come around often in historic Woodstock. Tucked away just a stone's throw from the heart of downtown, this classic American Foursquare is a time capsule of craftsmanship waiting for its next chapter. From the moment you step inside, the original woodwork and rich hardwood floors tell a story of a bygone era, offering a solid foundation for your creative vision. The

    Jose Rey Compass

    Unlisted Address
  • /2

    $339,990

    New Construction Pending
    • 2 Beds
    • 2 Baths
    • 1,512 Sq Ft

    2342 Heartwood Ln, Woodstock, IL 60098

    Bill Flemming HomeSmart Connect LLC

    2342 Heartwood Ln, Woodstock, IL 60098
  • /21

    $416,990

    New Construction $51K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    3823 Meadowridge Rd, Woodstock, IL 60098

    The first level of this two-story home is host to communal spaces, including a flex space off the foyer and an open floorplan shared among the family room, dining room and kitchen. A loft and three bedrooms can be found upstairs, two of which feature walk-in closets.

    Lennar Builder
    3823 Meadowridge Rd, Woodstock, IL 60098
  • /18

    $487,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,955 Sq Ft

    Sonoma Plan at Clublands of Antioch - Andare Series, Woodstock, IL 60098

    This single-story home provides a smart layout with the convenience of everything you need on one level. A flexible study is located near the entry which could also be used as a formal living or dining room. In the heart of the home is an open layout that connects the kitchen with center island effortlessly to the dining room and family room. There are three bedrooms in total including the large

    Lennar Builder
    2303 Scenic Dr Unit 37604119, Woodstock, IL 60098
  • /35

    $259,900

    Pending
    • 4 Beds
    • 4 Baths

    731 N Madison St, Woodstock, IL 60098

    Turn-key investment opportunity or ideal owner-occupied 2-flat in a prime Woodstock location! The first-floor unit is currently in the process of moving out, creating an outstanding opportunity for an owner-occupant to move right in while generating immediate rental income from the occupied second-floor unit. This maintained property has been updated over the years, white trim and doors, hardwood

    Paul Ambrogio Berkshire Hathaway HomeServices Starck Real Estate

    731 N Madison St, Woodstock, IL 60098
  • /31

    $375,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,461 Sq Ft

    Unlisted Address

    Beautiful 2 story home tucked away in a quiet neighborhood surrounded by nature, custom homes and a playground. Large windows throughout the home bring in ample sunshine and the gorgeous views. Only minutes to the historic Woodstock Square featuring farmers market, events, quaint shops, dining and more. Don't Miss Out!!!

    Julie Dahl Real 1 Realty

    Unlisted Address
  • /26

    $260,000

    • 5 Beds
    • 2.5 Baths
    • 2,736 Sq Ft

    526 W South St, Woodstock, IL 60098

    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. Roof is less than 2 years old. The staircase is gorgeous with two STAINED GLASS windows along the way. The large Living Room is inviting and the separate Dining Room is

    Elise Livingston RE/MAX Plaza

    526 W South St, Woodstock, IL 60098
  • /32

    $395,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,008 Sq Ft

    225 Hoy Ave, Woodstock, IL 60098

    The charm of Woodstock. This vintage home is only a few blocks to the Woodstock Square, train station and schools. Relax on the covered front porch or on the patio in the big private fenced backyard. Step inside and you'll appreciate the warmth of the original wood trim. It's not all old though. The kitchen was renovated in 2022, a major addition in 2021 and new furnace and A/C in 2020.

    Rick Bellairs Berkshire Hathaway HomeServices Starck Real Estate

    225 Hoy Ave, Woodstock, IL 60098
  • /14

    $461,135

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,382 Sq Ft

    3804 Meadowridge Rd, Woodstock, IL 60098

    The entryway leads to the first level of this new two-story home, where a versatile living room can be found off the foyer while the family room, dining room and kitchen share an open-concept design for seamless everyday living. Upstairs, four bedrooms provide enough space for a growing family.

    Lennar Builder
    3804 Meadowridge Rd, Woodstock, IL 60098
  • /21

    $249,900

    Pending
    • 3 Beds
    • 1 Bath
    • 1,047 Sq Ft

    1410 Thomas Dr, Woodstock, IL 60098

    Multiple Offers Received, highest and best called for by Noon Monday August 24th. Welcome to this beautifully updated 3-bedroom, 1-bath home featuring an inviting open floor plan designed for comfortable living and effortless entertaining. Professionally painted throughout, the home offers a fresh, clean, move-in-ready feel with modern updates and thoughtful features. The spacious living and

    Sheila Thomas RE/MAX Plaza

    1410 Thomas Dr, Woodstock, IL 60098
  • /30

    $420,000

    Pending
    • 3 Beds
    • 4 Baths
    • 2,048 Sq Ft

    14214 Perkins Rd, Woodstock, IL 60098

    Yes it is round! Step inside and check out all that it has to offer. Spacious rooms, tons of natural light, walk out basement, parking for 4, radiant heat in basement and garage, wrap around deck, storage shed, a perfect acre.... ready for you. Roof and gutters replaced in 2025, well pump and HVAC 3 yrs old, Storage shed. Home being sold as-is, stove is not working. Located a short distance to

    Becky Kirchner RE/MAX Plaza

    14214 Perkins Rd, Woodstock, IL 60098
  • /4

    $495,000

    • Land
    • 4.1 Acres
    • $120,732 per Acre

    LOT 7 Dillard Ct, Woodstock, IL 60098

    4.10 ACRES. FULLY IMPROVED PARK, POSSIBLE RAIL SERVICE IN REAR OF PROPERTY, READY TO BUILD SITES, ACROSS FROM BULL VALLEY 18 HOLE GOLF COURSE. CHOICE LOTS AVAILABLE. $2.75 ****** LOW MCHENRY COUNTY REAL ESTATE TAXES. MANY TAX-SAVING INCENTIVES ARE OFFERED BY THE CITY OF WOODSTOCK COMMUNITY DEVELOPMENT DEPARTMENT. CONTACT COMMUNITY DEVELOPMENT DIRECTOR JESSICA ERICKSON.

    Michael Bischoff Baird & Warner

    LOT 7 Dillard Ct, Woodstock, IL 60098
  • /24

    $479,250

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    3841 Meadowridge Dr, Woodstock, IL 60098

    ** 3 CAR GARAGE! * SPECIAL INCENTIVES AVAILABLE! * AUGUST DELIVERY! HOMESITE # 0091 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

    Bill Flemming HomeSmart Connect LLC

    3841 Meadowridge Dr, Woodstock, IL 60098
  • /27

    $454,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,607 Sq Ft

    Wren Plan at Riverwoods - Single Family, Woodstock, IL 60098

    The family room, kitchen and dining room can be found on the first level of this new two-story home, arranged in a convenient and contemporary open floorplan. On the same level are a study and flex space to provide additional space that the whole household can enjoy. All four bedrooms are located upstairs, each with a walk-in closet. An unfinished basement allows for more room to expand.

    Lennar Builder
    4258 Meadowridge Road St Unit 36950024, Woodstock, IL 60098

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