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$249,750
2 Beds ⋅ 2 Baths ⋅ 12553224 MLS ⋅ CLOSED Status
Welcome home to 119 S. Hill St. This 1,088 sq. ft. 2-bedroom 2 bath is a warm and inviting home offering a bright, comfortable feel with an abundance of natural light and large windows throughout. The family room provides a welcoming space around the fireplace with pleasant views, while the eat-in kitchen features ample cabinetry, updated flooring, and stainless steel appliances. The full basement layout lends itself well to a variety of uses, from storage and hobby space to the potential for future finishing and added living space. Recent updates include a washer in (2021), gas dryer in (2022), and a water heater replaced in 2024. Outside, the property sits on a generous lot with plenty of room for outdoor use and entertaining. Conveniently located within walking distance to the charm and energy of Historic Woodstock Square and all that the Historic Square has to offer. Enjoy the local shops, dinning and annual community events or take a stroll to Emricson Park with scenic trails, picnic area, fitness facilities, and aquatic center. Easy access to the Metra Woodstock station (UP-NW line) for commuting and many highways. Bring your ideas and make this your new place to call home.

119 S Hill Street, Woodstock
$300,000
3 Beds ⋅ 1 Baths ⋅ 12558569 MLS ⋅ CLOSED Status
LOVE HISTORIC homes? Want MODERN COMFORT? It is here at 926 TAPPAN Street in WOODSTOCK where VINTAGE CHARM MEETS MODERN RELIABILITY. You will be within a 10-minute STROLL or 3-minute drive to downtown WOODSTOCK SQUARE for dining, shopping and commuter rail, METRA. Now is your chance to own a beautifully MAINTAINED and UPDATED, vintage AMERICAN FOUR-SQUARE TWO-STORY home with exceptional character and ALL MODERN UPDATES including GAS FORCED AIR for HEATING and CENTRAL AIR CONDITIONING. Original 1912 STAINED GLASS WINDOWS anchor the home's timeless appeal, while thoughtful improvements throughout make it truly MOVE-IN READY from electrical to plumbing to lighting & finishes and mechanicals. Set on a NICE SIZED LOT with MATURE TREES and a PARTIALLY FENCED YARD, step onto a FRONT PORCH large enough to rock the day away enjoying your manicured lawn and flowers. Walk into the home where it opens a nice size FOYER leading to an open and spacious living and dining area ideal for everyday living and entertaining. Brazilian cherry HARDWOOD floors and new light fixtures on the main level add to the comfort. The kitchen offers abundant storage with 42" CABINETS, a subway tile BACKSPLASH, and UPDATED STAINLESS STEEL APPLIANCES (2021-25) including a GAS STOVE. Six-panel HARDWOOD DOORS add warmth and continuity throughout, and an UPDATED BATHROOM (2020) is a standout. LAUNDRY including a large SOP/UTILITY SINK round out indoor modern features. Just off the kitchen, enjoy a BACK PORCH with BENCH SEATING to enjoy sun and coffee. Onward to the BACKYARD there is plenty of space to garden, play, or lounge. To round off modern living a 2-CAR GARAGE with EXTENSIVE additional ELECTRIC ideal for hobbies, workshop use, or equipment. Additional highlights include an ASPHALT DRIVEWAY (2017), ROOF and SIDING (2016). There is generous STORAGE in both the BASEMENT and ATTIC. Bonus - do you game or WFH? SUPER FAST INTERNET are ready for you! The home is FULL DRYWALL with UPDATED ELECTRICAL AND PLUMBING (NEW WATER HEATER ~2025) and don't forget -- gas forced-air heat, central air (new furnace and A/C condenser Feb 2026). All of this and IDEALLY located just minutes from the METRA Woodstock station and WOODSTOCK SQUARE. Walk in less than 10 minutes, drive in 3 minutes and you are amongst parks, dining, shopping, entertainment, farmers market, and public transportation! A RARE OPPORTUNITY TO OWN A WELL-CARED FOR HOME WHERE CHARACTER, CONDITION, AND LOCATION ALIGN.

926 Tappan Street, Woodstock
$600,000
12558322 MLS ⋅ ACTIVE Status

1212 N Seminary Avenue, Woodstock
$260,000
4 Beds ⋅ 2 Baths ⋅ 12554288 MLS ⋅ CLOSED Status
Very well maintained income producing 2-unit property just a few blocks from the Historical Woodstock Square, close to dining, shopping and the Metra. Each unit has 2 Bedrooms and 1 Bath, separate utilities paid by tenants, including water, gas, electric, garbage service, plus both units have access to basement with separate laundry hookups, separate furnaces, water heaters and electric panels. Tenants take care of lot mowing and snow removal. Each unit has 2 separate private entrances, 2 parking spaces, and use of a private porch area. Smoke & carbon monoxide detectors are in each unit and window blinds are included. Several updates include upgraded electric service, newer doors and flooring, and some new appliances. Roof was a complete tearoff approximately 13 years ago; driveway has been seal coated by owners. One unit approx 1,334 sq.ft.; 2d unit approx. 947 sq. ft. A long term tenant resides who will be vacating before the end of May, 2026. Recently vacated 2nd unit has recently had several repairs and improvements including fresh paint. The building has minimum maintenance and the yearly expenses are taxes and insurance.

726 S Jefferson Street, Woodstock
$599,000
12552826 MLS ⋅ ACTIVE Status
Woodstock Square Mall is prominently located in the heart of downtown Woodstock, immediately adjacent to the city's historic town square. Positioned at the corner of South Johnson and Jackson Streets, the property benefits from exceptional proximity to key civic, cultural, and commercial destinations, including the Woodstock Opera House, McHenry County Courthouse, City Hall, and a well-established mix of local shops, restaurants, and service providers. THIS IS PROPERTY IS ENCOMBERED WITH A GROUND LEASE VALID THRU 2032. Contact listing agent with questions.

110 S Johnson Street, Woodstock
$220,100
4 Beds ⋅ 2 Baths ⋅ 12544095 MLS ⋅ CLOSED Status
Wow-come take a look at this fantastic opportunity to own a two-unit property in Woodstock, just minutes from downtown and close to the train! This versatile property is perfect for a house hack or as an investment and has the potential to be a true cash cow. Each unit features 2 bedrooms and 1 bath, plus there's an awesome two-car garage with a second level that could be used for storage or additional income. An unfinished basement offers even more potential to add value. With its great location and income possibilities, this one won't last-book your showing ASAP!

919 Clay Street, Woodstock
$285,000
6 Beds ⋅ 2 Baths ⋅ 12542345 MLS ⋅ CLOSED Status
Great investment opportunity in the heart of Woodstock. This maintained 2 unit building sits just blocks from the historic Woodstock Square and is minutes from shopping, dining, and the Metra station-an ideal location for commuters and renters alike. Each unit offers 3 bedrooms, and the property is currently occupied by long term tenants, providing immediate and reliable rental income. A solid addition to any investor's portfolio.

922 Tappan Street, Woodstock
$257,000
4 Beds ⋅ 2 Baths ⋅ 12542314 MLS ⋅ CLOSED Status
Unlock the potential of this charming 2 unit property located only a short stroll from the Woodstock Square. Enjoy the convenience of nearby boutiques, restaurants, and the Metra Train, making this an attractive spot for renters. Both units feature 2 comfortable bedrooms and are home to long-term tenants who value the space and location. Whether you're expanding your investment portfolio or stepping into real estate for the first time, this property offers stability and opportunity.

118 W Donovan Avenue, 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
$140,000
2 Beds ⋅ 1 Baths ⋅ 12535555 MLS ⋅ CLOSED Status

551 Mchenry Avenue, Woodstock
$245,000
3 Beds ⋅ 1 Baths ⋅ 12533903 MLS ⋅ CLOSED Status
Charming 3-bedroom cottage-style home offering character and flexibility. This well-maintained property features hardwood floors, a bright living room, and a formal dining area off the kitchen. The kitchen offers ample cabinet space and great potential for future updates. All three bedrooms and a full bathroom are located on the main level, with bedrooms freshly painted. The finished attic provides additional flexible living space. Basement includes a toilet and shower with rough-in already in place. The area is dated but offers a solid starting point for a refreshed lower-level bath. Major updates: new roof and gutters (2022) and updated windows throughout, including the basement. Enjoy a fenced backyard with patio, plus a 2-car garage and extended driveway for ample parking. Conveniently located near the Woodstock Square, Metra station, and local schools.

331 Chestnut Street, Woodstock
$455,000
3 Beds ⋅ 3 Baths ⋅ 12462273 MLS ⋅ CLOSED Status

14006 Sunset Ridge Road, Woodstock
$240,000
2 Beds ⋅ 2 Baths ⋅ 12527710 MLS ⋅ CLOSED Status
Prime investment opportunity with high visibility in the heart of Woodstock! Zoned B-3, this property is 2 units with a possible 3rd unit option including roughed plumbing for a bathroom. Lower level is perfect for commercial and office use with flexible space and half bath, while the spacious residential upper level is a 2 bed, 1 bath flat with a generously sized flex room for extra living. Private driveway and parking lot. Close to shopping, dining, and Metra service.

722 E Calhoun Street, Woodstock
$306,000
3 Beds ⋅ 2 Baths ⋅ 12526982 MLS ⋅ CLOSED Status
Mid-Century Modern Charmer ranch in the Heart of Woodstock! Just 0.6 miles from Historic Woodstock Square, this well-maintained home offers incredible convenience to shopping, dining, festivals, and everyday amenities. Step inside to a light-filled living room featuring hardwood flooring and crown molding. The freshly painted kitchen includes a ceramic tile backsplash and a functional layout. A standout of the home is the spacious three-season sunroom, offering direct access to the expanded patio-an ideal spot to enjoy the outdoors in comfort. The fully fenced backyard feels like a private oasis with fresh landscaping and plenty of space to relax or entertain. An oversized shed with a concrete floor and electricity provides excellent additional storage or hobby space. The lower-level living area adds another comfortable zone to spread out, features a laundry room and abundant storage. Warm, inviting, and close to everything Woodstock has to offer-this home is a must-see!

656 Oak Street, Woodstock
$285,000
3 Beds ⋅ 2 Baths ⋅ 12527322 MLS ⋅ CLOSED Status
(Agent-Owned Property) spacious 3-bedroom, 2-bathroom home offering comfort, character, and location. The main level features two bedrooms and a full bath. Upstairs, an additional living room area provides the perfect flex space-ideal for a home office or cozy sitting room. The lower level includes a third bedroom, a second full bathroom featuring a jacuzzi tub, and another living room with walkout access to the back patio. This charming residence boasts an open floor plan, vaulted beamed ceilings, and a gas fireplace. The kitchen offers ample counter space. The roof was done in 2024, Water heater in 2022. Located just one block from the playground on Dick Tracy Way and directly across from the 20-acre Ryder's Woods Nature Preserve, with beautiful walking trails. Only two blocks from Groundhog Day B&B and just a short distance to the Woodstock Square and Metra station. This property is being sold as-is.

554 Fremont Street, Woodstock
$299,000
4 Beds ⋅ 3 Baths ⋅ 12524673 MLS ⋅ CLOSED Status
Wonderful 2-unit investment opportunity near downtown Woodstock in great location. With 2 separate units this property offers multiple streams of income providing financial flexibility and stability to investors or homeowners looking to minimize their mortgage. This property has been diligently maintained by one family for over 100 years. 4 car garage, full basement with extra bathroom, tons of charm and character with the woodwork and recent updates .Being sold "As-Is".

912 Clay Street, Woodstock
$215,000
2 Beds ⋅ 2 Baths ⋅ 12518131 MLS ⋅ CLOSED Status

Woodstock
$205,000
2 Beds ⋅ 1 Baths ⋅ 12519356 MLS ⋅ CLOSED Status
Don't miss out on this incredible opportunity - the best in its price range! This well-maintained two-bedroom, one-bathroom cottage home is situated on a beautiful stretch of Walnut Drive, just 1.4 miles from the charming Woodstock Square. The home sits on a great lot and features a spacious 1.5 car garage, perfect for extra storage. This property is move-in ready and requires no additional work. Improvements include a new GE fridge, new 40 gallon water heater, updated GE oven with 5 burners, new red cedar back door threshold, and an updated bathroom with beautiful tile. Fiber has been run to the unit from i3, or cable internet is available. The heating and air conditioning system is also newer and the established annual peonies in the front are beautiful in the late spring! The property is perfect for a new home buyer, or an investor looking for a sought after unit.

1536 Walnut Drive, Woodstock
$252,000
2 Beds ⋅ 1 Baths ⋅ 12520930 MLS ⋅ CLOSED Status
Clean and fresh ranch home with large garage and full basement. New paint, carpet and refinished hardwood floors, fenced yard, whole house fan, new composite decking in 2024, newer siding, windows, furnace, A/C and even a back-up generator. All appliances are included.

417 Stewart Avenue, Woodstock
$173,000
2 Beds ⋅ 2 Baths ⋅ 12518821 MLS ⋅ CLOSED Status
Discover the perfect opportunity for both new and seasoned investors with this well-maintained, income-producing 2-unit property just a short walk from the lovely Woodstock Square. Compact in size but big on value, this rare 2-unit property offers reliable rental potential with minimal upkeep required. Each unit features a practical, efficient layout with bright living spaces, updated flooring, and move-in-ready finishes. Tenants will appreciate the comfort and convenience, while owners benefit from low operating costs and strong rental demand. The property includes parking and a garage for each unit, a tidy backyard, and enough recent updates ensure hassle-free ownership from day one. Whether you're looking to expand your portfolio or start your investment journey, this turnkey property is ready to deliver consistent returns.

139 E Todd Avenue, Woodstock
$174,000
1 Beds ⋅ 1 Baths ⋅ 12517377 MLS ⋅ CLOSED Status

Woodstock
$225,000
3 Beds ⋅ 1 Baths ⋅ 12516642 MLS ⋅ CLOSED Status
Welcome to this well-maintained 3-bedroom ranch home nestled in a quiet, established neighborhood. This inviting property offers a bright and functional layout in a desirable location. The open living room has hardwood floors. The bedrooms have updated flooring. Fresh paint and new windows add to the move-in-ready appeal. A full unfinished basement provides ample storage. There is also an attached garage for convenience. Located just minutes from the historic Woodstock Square, shopping, schools, and Metra train station, this home combines small-town charm with everyday practicality - a wonderful opportunity.

125 Arthur Drive, Woodstock
$290,000
4 Beds ⋅ 2 Baths ⋅ 12499355 MLS ⋅ CLOSED Status
STEP BACK IN TIME WITH THIS DELIGHTFUL 4 BEDROOM 1.5 BATH VINTAGE GEM, PERFECTLY NESTLED WALKING DISTANCE TO THE WOODSTOCK SQUARE. GREETED BY A WELCOMING FRONT PORCH, YOU WILL ENTER INTO A SPACIOUS LIVING ROOM THAT FLOWS INTO A FORMAL DINING ROOM AND WELL EQUIPED KITCHEN-IDEAL FOR EVERY DAY LIVING AND ENTERTAINING. INSIDE, THE REFINISHED HARDWOOD FLOORS GLEAM WITH A TIMELESS APPEAL, COMPLEMENTED BY ORIGINAL STAINED GLASS WINDOWS THAT INFUSE THE SPACE WITH CHARACTER AND NATURAL LIGHT. MODERN UPDATES ENSURE PEACE OF MIND: A 3 YEAR NEW ELECTRICAL PANEL WHICH YOU CAN ALSO CHARGE YOUR CAR FROM, A ONE YEAR NEW ROOF WITH A TRANSFERABLE WARRANTY, AND A NEW REFRIGERATOR. UPSTAIRS, FOUR COZY BEDROOMS OFFER AMPLE SPACE FOR FAMILY OR GUESTS. OUTSIDE, A LOVELY TIERED BACKYARD PERFECT FOR OUTDOOR GATHERINGS WITH A FENCED YARD. THIS HOME BLENDS VINTAGE CHARM WITH THOUGHTFUL UPGRADES. MAKE IT YOURS TODAY. **PROPERTY HAS RADON MITIGATION SYSTEM**EVERYTHING IS IN WORKING ORDER AS-IS PLEASE

517 Bunker Street, Woodstock
$360,000
3 Beds ⋅ 2 Baths ⋅ 12511242 MLS ⋅ CLOSED Status
Schedule your showing and call the movers, that's all you need to do, because the rest has already been done! Rare, nearly 1 acre lot within walking distance to the block! Be prepared to be impressed with this stunning 2 story home from 1870! The current owners have done a remarkable job with adding modern flare while maintaining the original charm. The kitchen has been given a modern facelift including SS appliances, farm sink, granite countertops and a commercial range/oven and hood vent. Enjoy cooking while engaging with others with the open kitchen floor plan. The large island seats approximately four people, while the eat in dining room provides additional space for a formal dining experience or to seat additional guests. The family room is a real vibe-you are engulfed with an unexplainable feeing of peace and warmth. Perhaps its the grounding of the oak hardwood floors or the original custom built-ins....maybe its the warmth of the wood burning fireplace and its gorgeous fireplace surround. Regardless, you will enjoy this space and the abundance of natural light it provides. The main floor master is completed with a full bathroom, laundry room(with heated floors) and screened porch that overlooks a magical park like backyard. Move upstairs where you will find the primary bedroom with more original and custom built ins and fireplace that will keep you warm during the cold midwest winters! The 2nd level is completed with a 2nd remodeled bathroom and a 2nd and 3rd bedroom! Move outside, where you will enjoy a true backyard paradise! This home sits on approx .71 acres and is across from Dean Elementary school. Newer roof, siding and most of the windows have been replaces! to shopping and dining. Dont let this rare opportunity pass you by as this house has only exchanged less than a handful of times in the last 155 years!

615 Dean Street, Woodstock
$298,000
4 Beds ⋅ 2 Baths ⋅ 12509498 MLS ⋅ CLOSED Status

320 W Donovan Avenue, Woodstock
$239,000
5 Beds ⋅ 2 Baths ⋅ 12507974 MLS ⋅ CLOSED Status
This home has classic architectural details. Light and bright sunroom addition with windows galore and a vaulted wood ceiling. First floor bedroom with full bath. There is a temporary wall that could be taken down to bring back the full front wrap around porch. The parlor and dining room ceilings feature ornate ceiling medallions/roses. The kitchen has table space with a built in bench with storage. This vintage home is waiting for your creative touch to restore its natural beauty and timeless character. Ideally located near the charming Woodstock Square, METRA, dining and shopping.

514 Washington Street, Woodstock
$275,000
4 Beds ⋅ 2 Baths ⋅ 12483383 MLS ⋅ CLOSED Status
Large home,(4-6 bedrooms possible depending upon reconfiguration) just blocks south of Woodstock's historic Square, on an extra-wide and deep lot with mature trees surrounding the house. The property has been a duplex for many years and can continue as such with over $2,000 in monthly income, or it is perfect for the buyer wanting to gain equity greatly by returning this Victorian to its original single-family splendor (suggested plans in the house that show possible floor plans based on the original layout). The downstairs ceiling height is 9 feet. So much space, plus a full walkout basement to the deep backyard, where a large cement patio is ready for the BBQ grill and fire pit. The basement has a high ceiling and can be finished to be used for additional living space. Several stained glass windows and leaded-cut windows, original woodwork, architectural roofing, tandem furnaces, water heaters, AC, and updated electrical service in two panels provide many circuits with room for more circuits. The upstairs bathroom has a separate bonus room that can be used as an office, playroom, or storage area. A metal shed in the backyard provides storage for yard and garden tools. Find your Woodstock dream and build immediate equity with your improvements, or claim your income from high-demand rentals. Because the home is currently configured as a duplex, a new owner could live in one half while rehabbing the other, or rent one unit while converting the other half. Sold "as is"(The home is realtor-owned).

601 S Jefferson Street, Woodstock
$338,000
3 Beds ⋅ 2 Baths ⋅ 12505410 MLS ⋅ CLOSED Status
Tucked away on a quiet street in one of the area's most beloved towns sits a home full of heart and character. It's vintage where it counts, updated where it matters, and overflowing with warmth. The kind of home that instantly feels right - close to everything yet perfectly peaceful. Welcome to 389 Lincoln Ave in the wonderful historic town of Woodstock. This home is as charming as the day is long and has much to be desired. With its more open floor plan on the main level, vintage wood floors throughout, and woodwork for days, this home strikes the perfect balance of classic and updated. The living room is warm and inviting, featuring built-in bookshelves, true hardwood floors, and beautiful craftsmanship that gives the space a timeless feel. The open family and dining room layout creates the perfect flow for entertaining - whether you're hosting friends or enjoying a quiet evening at home. The antique collector's kitchen is a true standout, filled with vintage, repurposed pieces that come together to create a one-of-a-kind space you'll instantly fall in love with. Recent updates include new siding (2021), front-loading washer & dryer (2019), water heater (2019), and a flagstone patio (2021). There's so much more to see and experience - this home is sure to impress and stand out from the rest. Just steps from the historic Woodstock Square, where the iconic 1889 Opera House still hosts live performances and where farmers' markets, parades, and local festivals fill the streets each season. Back in 1910, Woodstock earned the nickname "Typewriter City", when the Emerson Typewriter Company produced machines here that were shipped all around the world. Today, the same square continues to be the heart of the community - vibrant, walkable, and filled with timeless charm. Commuters will love being so close to the Woodstock Metra Station, located right by the square. The Union Pacific Northwest Line runs directly to downtown Chicago's Ogilvie Transportation Center, offering an easy and convenient option for travel to the city.

389 Lincoln Avenue, Woodstock
$159,900
2 Beds ⋅ 1 Baths ⋅ 12502566 MLS ⋅ CLOSED Status
This spacious 2-bedroom plus bonus room, 1-bath home offers a spacious layout and endless possibilities in one of Woodstock's most inviting neighborhoods. Step inside to find a functional floor plan with generous room sizes and a versatile bonus room that can serve as an office, guest room, or hobby space. Enjoy abundant natural light throughout the living and dining rooms with beautiful hardwood floors, along with a full unfinished basement ready for your personal touch or additional living space. Expansion possibilities with large attic space. Set on a generous lot with a detached garage and a sunroom overlooking the backyard, this home offers plenty of room to enjoy both indoors and out. Located just minutes from historic Woodstock Square, the Metra station, schools, parks, and local shopping, this property combines small-town charm with everyday convenience. Whether you're a homeowner looking to customize your next space or an investor searching for a great opportunity in a growing community, 908 Bunker St delivers great value and location. Home is being sold As-Is.

908 Bunker Street, Woodstock
$248,000
3 Beds ⋅ 2 Baths ⋅ 12502194 MLS ⋅ CLOSED Status
This thoughtfully updated home offers the perfect blend of comfort, style, and functionality for today's family. Step inside and you'll immediately notice the gleaming hardwood floors that flow throughout the home, creating a warm and inviting atmosphere. The kitchen has been refreshed with brand-new stainless steel appliances, including a refrigerator, oven, and dishwasher - ready for your first family meal. The primary bedroom suite serves as a relaxing retreat, featuring a beautifully updated bathroom with modern tile, a sleek vanity, and elegant fixtures. Every detail feels fresh, bright, and move-in ready. Downstairs, the spacious full basement provides endless possibilities - whether you need a playroom, home gym, workshop, or extra storage, this clean and freshly finished space can easily adapt to your family's needs. With its modern updates, quality finishes, and warm character, this home is ready to welcome its next owners. Don't miss the chance to make it yours - schedule a showing today!

1409 N Seminary Avenue, Woodstock



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