Browse All Woodstock IL Historical Properties for Sale

3 Beds ⋅ 1 Baths ⋅ 12737727 MLS ⋅ NEW Status

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 oversized detached 2+ car garage provides plenty of room for vehicles, storage, hobbies, and more. Enjoy the generous yard and peaceful setting while still being close to everything Woodstock has to offer. Home needs some TLC and updating, but offers a wonderful opportunity for a buyer ready to add their personal touches. Property is being sold AS-IS.

113 Raffel Road, Woodstock

$365,000

3 Beds ⋅ 3 Baths ⋅ 12726095 MLS ⋅ NEW Status

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 with a zero step shower, offering the potential for multigenerational living. Upstairs, the primary bedroom has its own attached bath and a separate laundry room. Inside, there's room for everyone to spread out, with a massive living room featuring hardwood floors and a wood burning fireplace, plus a separate family room for even more living space. Outside the freshly painted exterior opens to multiple outdoor living spaces, including a covered front porch and a back deck spanning more than 800 square feet. Plenty of room to entertain, relax, and enjoy this incredible location. A truly unique home on one of Woodstock's most iconic streets, just minutes from schools and everything the Square has to offer.

517 Dean Street, Woodstock

$285,500

3 Beds ⋅ 2 Baths ⋅ 12740408 MLS ⋅ NEW Status

Welcome to this charming brick bungalow in Woodstock! 3 bedrooms. 1.5 bath. Harwood floors, an enormous finish attic bedroom. Home offers classic character and comfortable living. The spacious layout provides plenty of space for everyday living and entertaining. Enjoy the convenience of a 2-car garage plus a shed for additional storage. A great opportunity to own a solid brick home! Sold As Is

867 Clay Street, Woodstock

$299,000

3 Beds ⋅ 2 Baths ⋅ 12719690 MLS ⋅ CONTINGENT Status

Welcome to this beautifully refreshed ranch home in a fantastic Woodstock location! Just over a mile from the heart of downtown Woodstock and the Metra station, this home offers easy access to shopping, dining, parks, and nearby schools. Inside, you'll find three bedrooms and one and a half baths, along with brand new flooring throughout and fresh paint that gives the home a clean, inviting feel. The kitchen opens to a spacious three-season room, providing additional living space and a great spot to enjoy views of the backyard. The partially finished basement adds even more versatility with a recreation room, office, roughed-in plumbing for a future bathroom, and a large storage area. Outside, enjoy a generous backyard sitting on just over a quarter acre. Solid, well maintained construction combined with fresh updates makes this a wonderful opportunity to move right in and enjoy all that Woodstock has to offer! The seller is offering a 12 month home warranty.

611 W Kimball Avenue, Woodstock

$475,000

4 Beds ⋅ 3 Baths ⋅ 12723757 MLS ⋅ NEW Status

This home in Walrose Manor offers a private oasis on 2/3 of an acre, but still close to town and conveniences. The updated kitchen provides a fresh, modern space for everyday living and entertaining, while the huge family room with gas fireplace and attached sun room offers plenty of room to gather, relax, and enjoy time together. The formal dining room and living room offer more traditional living spaces as well. The hardwood on the main floor was refinished, plus newer carpet in the family room. Upstairs the generous primary suite offers vaulted ceiling and full bath and walk in closet. Major updates include a new roof, new furnace, and fresh exterior paint, providing peace of mind for years to come. Step outside to your own private backyard retreat featuring an in-ground pool and gazebo, perfect for summer entertaining and relaxing. The pool is equipped with a new heater and filter for added enjoyment and convenience. A wonderful combination of thoughtful updates, generous living space, and outdoor amenities-ready to enjoy!

749 N Sharon Drive, Woodstock

$249,999

3 Beds ⋅ 1 Baths ⋅ 12732625 MLS ⋅ CONTINGENT Status

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 floors and fireplace, an eat-in kitchen, two main-level bedrooms, and a spacious second-floor loft. FULL basement offers great storage and future potential. Big-ticket items already done: NEW roof (2026), NEW gutters (2026), NEW reverse osmosis water filter (2026), NEW microwave, washer, and garbage disposal (2026). Property is being sold as-is. NOTE: 3rd bedroom is loft style upstairs.

822 N Madison Street, Woodstock

$242,000

4 Beds ⋅ 2 Baths ⋅ 12673675 MLS ⋅ CONTINGENT Status

Woodstock

$259,900

4 Beds ⋅ 4 Baths ⋅ 12730404 MLS ⋅ CONTINGENT Status

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 and laminate flooring, updated lighting, and loads of windows that fill both units with natural light. The first-floor unit offers three bedrooms, a white cabinet kitchen complete with updated appliances, large living room and an updated full bath and half bath. The second-floor unit features one bedroom, large living room, nicely sized kitchen and updated bathrooms - one full and one half. Additional features include separate utilities for each unit, washer and dryer hookups in the basement (currently only the 1st floor unit has access to the basement), and a low-maintenance setup where tenants pay all utilities and are responsible for lawn care. Whether you're looking to live in one unit or expand your investment portfolio with a true turn-key property, this is an exceptional opportunity. Conveniently located just minutes from historic Downtown Woodstock Square, shopping, restaurants, schools, parks, and commuter routes. Don't miss your chance to own a versatile income-producing property in one of Woodstock's most desirable locations! Newer price gives you the opportunity to make exterior updates, if needed. Priced to sell!

731 N Madison Street, Woodstock

$325,000

3 Beds ⋅ 2 Baths ⋅ 12674042 MLS ⋅ CONTINGENT Status

Don't miss this incredible opportunity to own a beautifully updated home full of character and craftsmanship. Start your mornings or unwind in the evenings on the inviting front porch, rebuilt less than two years ago and freshly painted this year. Inside, the living and dining rooms have been completely transformed. Both spaces were taken down to the studs, ceilings were raised, and beautiful beams were added to create a welcoming feel. New electrical, ceiling fans, and custom woodwork showcase the owner's attention to detail throughout the home. The kitchen was completely renovated within the last three years and features granite countertops, custom-built cabinetry, new drywall, updated plumbing, electrical, and shiplap ceilings. Every detail was thoughtfully designed to blend function and style by the owner. The back porch was enclosed, adding valuable living space that includes a convenient half bath and a double-wide sliding door leading to a peaceful deck and backyard. Upstairs, you'll find three bedrooms and a full bath. The bedroom and hallway doors have been refinished, and additional custom woodwork has been added throughout the upper level, enhancing the home's warmth and charm. This home offers a rare combination of modern updates, quality craftsmanship, and timeless character. Close to the downtown area. The owner is offering a credit to finish the Full bath he started and cannot finish due to being out of state. Selling as-is.

902 Wicker Street, Woodstock

$295,000

3 Beds ⋅ 2 Baths ⋅ 12720651 MLS ⋅ ACTIVE Status

This two-unit property offers a two-bedroom, one-bath apartment on the main level and a one-bedroom, one-bath apartment upstairs. Additional features include a two-car garage, a peaceful setting, and a friendly neighborhood. Located just seven minutes from downtown Crystal Lake and 11 minutes from downtown Woodstock, with CRYSTAL LAKE highly rated Prairie Ridge High School.

8320 Prospect Street, Woodstock

$395,000

4 Beds ⋅ 2 Baths ⋅ 12717928 MLS ⋅ CONTINGENT Status

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.

225 Hoy Avenue, Woodstock

$240,000

4 Beds ⋅ 2 Baths ⋅ 12722578 MLS ⋅ PRICE CHANGE Status

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 room to enjoy. This home is in need of repairs and presents an exciting opportunity for buyers looking to renovate, customize, and potentially build equity. Conveniently located just steps from Northwood Middle School and near Metra train access, dining, shopping, historic downtown Woodstock, and more. Bring your ideas and transform this property into the home you've been envisioning!

107 W Melody Lane, Woodstock

$269,900

2 Beds ⋅ 2 Baths ⋅ 12726037 MLS ⋅ CONTINGENT Status

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 looking for room to entertain, create the ultimate backyard oasis, store equipment, pursue hobbies, or simply enjoy your own private setting, this property delivers. This Home is Constructed of durable concrete block with a concrete foundation, this home was built to stand the test of time! Concrete block construction is prized for its exceptional strength, durability & resistance to fire, pests & the elements. Its solid construction helps reduce outside noise while providing excellent thermal mass, which can contribute to more consistent indoor temperatures & improved energy efficiency throughout the seasons. Built with materials rarely found in today's wood-frame construction, this home offers the lasting quality, stability & peace of mind that discerning buyers appreciate. The maintenance-free vinyl siding, vinyl soffits & fascia provide lasting durability with minimal exterior upkeep. Major improvements have already been completed, including a newer 30-year roof (approximately 1 year old), Andersen replacement windows throughout (approximately 3 years old) & high-efficiency furnace. An inviting enclosed porch entry with plank wood walls & a cedar closet creates the perfect blend of character, warmth & functionality. The beautifully remodeled kitchen is sure to delight the home chef, featuring gorgeous custom poplar shaker-style cabinetry with rich wood tones, soft-close doors & drawers, dual Lazy Susan corner cabinets, generous table space & all appliances included. Throughout the home you'll appreciate six-panel solid wood doors, quality wood trim, raised baseboards, spacious room sizes & hardwood flooring beneath the living room & upstairs bedroom carpeting. The inviting four-season room is a true extension of the home, creating the perfect indoor-outdoor connection. Picture yourself relaxing beside the wood-burning fireplace while taking in peaceful views of the changing seasons, from colorful fall evenings to snow-covered winter landscapes. Complete with insulated walls, recessed lighting & a warm wood plank ceiling, it's a space you'll enjoy year-round. Gather in the spacious living room featuring a custom built-ins & entertainment center that stays. Step outside to one of the most impressively constructed decks you'll find, featuring a pergola & reinforced engineering with substantial footings designed to support a hot tub. It's the perfect setting for summer cookouts, outdoor dining, entertaining, or simply unwinding at the end of the day. Car enthusiasts, contractors, hobbyists, landscapers & small business owners will truly appreciate the flexibility & convenience of having an impressive on-site outbuilding. In addition to the detached 2 & 1/2-car garage with loft storage & insulated walls, you'll find a Massive heated workshop that's over one car wide & at least two cars deep, complete with a floor drain, exhaust fan, heater, window air conditioner & 50-amp electrical service. A 20' x 20' carport on a concrete pad & an additional storage shed provide even more versatility for vehicles, equipment, trailers & recreational toys. The full basement offers excellent ceiling height, a 3rd bedroom, 2nd full bath, laundry area with utility sink & reverse osmosis water filtration system. A property offering this combination of a HALF-acre of land, exceptional concrete block construction, extensive updates, abundant garage & outbuilding/workshop space, affordable taxes & a location just minutes from the charm, shopping, dining & year-round events of the Historic Woodstock Square is truly a rare find. One-of-a-kind opportunity!

809 Washington Street, Woodstock

$300,000

5 Beds ⋅ 3 Baths ⋅ 12691511 MLS ⋅ ACTIVE Status

Opportunity awaits in this classic home that has been lovingly owned by the same family for over 40 years. While the home is ready for updating, it offers timeless architectural character, quality craftsmanship, and an unbeatable location, all the perfect ingredients to create your dream home. Step inside to discover striking natural-tone staircase millwork, beautiful transoms above the doorways, solid 5-panel wood doors, nearly 9-foot ceilings, built-in cabinetry, and two charming fireplaces (shared chimney has been capped). One of the five bedrooms is on the main level. Outside, enjoy barbecues on the deck overlooking the spacious yard that backs to a school field and playground, providing an open, park-like setting. The property has been maintained without pesticides and features an established collection of perennials and edible gardens, including hostas, strawberries, black raspberries, asparagus, irises, and a composting area. A detached two-car garage with a unique canoe bump-out offers additional storage for outdoor enthusiasts. Newer Roof and A/C in 2026. The location is truly exceptional-just minutes from vibrant downtown events, restaurants, shopping, the Metra station, schools, and the library. Whether you're looking to restore its original beauty or update it with your own style, this home offers incredible potential in one of the area's most desirable neighborhoods. Home is being sold As-is.

370 Lincoln Avenue, Woodstock

$299,900

3 Beds ⋅ 2 Baths ⋅ 12719935 MLS ⋅ CONTINGENT Status

Beautiful curb appeal! This home features 3 nice size bedrooms 1 bathroom with 1 car garage. Large living room with hardwood flooring. Kitchen with table space. Nice size window from kitchen looking to the backyard. You'll find plenty of storage closets around. A full unfinished basement offers loads of possibilities for storage space or the entertainment area. Exterior might be the best part of all. Gigantic backyard, with a nice size deck and gorgeous stoned patio. Yard backs to city lot, enjoy the peace and quiet. Nicely located in the north side of town yet very close to the Historic Woodstock Square for shopping, movies, and restaurants. This beautiful home is ready for you to move in and make it your home, come and see it today!

1109 Wicker Street, Woodstock

$249,000

3 Beds ⋅ 2 Baths ⋅ 12718845 MLS ⋅ CONTINGENT Status

Welcome home to this charming 3-bedroom Cape Cod with plenty of space inside and out! The home features luxury vinyl flooring throughout, six-panel doors, a separate dining room, and a bright sunroom overlooking the backyard. The unfinished full basement includes a bathroom and offers great potential for additional living space, a home gym, or storage. Recent updates include new siding in 2023, a new dishwasher, washer, dryer and central air. Outside, enjoy the large fenced backyard, spacious deck with a covered pergola, and detached 2-car garage.

663 Pleasant Street, Woodstock

$325,000

3 Beds ⋅ 2 Baths ⋅ 12718520 MLS ⋅ CONTINGENT Status

ELEVATOR starts the list of UPDATES and fabulous amenities at this thoughtfully maintained RANCH where comfort, functionality and flexibility come together. Beautiful HARDWOOD FLOORS create a warm, timeless feel throughout the main living spaces, while abundant natural light pours through recently replaced front Bay windows. A rare ELEVATOR and features thoughtfully designed for ACCESSIBLE LIVING, including an accessible bathroom with a ZERO THRESHOLD SHOWER, make everyday living easier while offering a level of convenience that's hard to find. Step outside and discover one of this home's standout features. The FULLY FENCED BACKYARD is a peaceful retreat with mature landscaping, a spacious DECK and a SCREENED PORCH that's perfect for morning coffee, summer dinners, or simply relaxing while enjoying the view. Downstairs, the FULL BASEMENT offers endless possibilities with a dedicated WORKSHOP and an expansive unfinished area that's truly a BLANK CANVAS. Whether you envision a recreation room, home gym, hobby space, additional living area or all of the above, you'll have the room to make it your own. 2nd Bathroom in the Basement is being conveyed in AS-IS condition, as it has not been used recently. Thoughtful improvements throughout the home provide added peace of mind, including RECENTLY REPLACED FRONT WINDOWS, a professionally installed BASEMENT DRAINAGE SYSTEM designed to help keep the lower level dry and UPGRADED ROOF VENTILATION to improve attic airflow and support the longevity of the roofing system. Located on a quiet street just minutes from HISTORIC WOODSTOCK SQUARE, you'll enjoy easy access to locally owned restaurants, coffee shops, boutique shopping, parks, year-round festivals, the WOODSTOCK FARMERS MARKET and the METRA STATION for an easy commute. Whether you're purchasing your FIRST HOME, looking for the ease of ONE LEVEL LIVING, or searching for a home that can comfortably adapt to your needs over time, this property offers the flexibility, thoughtful features, and welcoming setting to make it feel like home from day one.

136 E Kimball Avenue, Woodstock

$339,900

3 Beds ⋅ 1 Baths ⋅ 12711814 MLS ⋅ ACTIVE Status

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 parking! Enjoy an unbeatable location just a short walk to the historic Woodstock Square - home to charming shops, restaurants, the Woodstock Opera House, and year-round community events. Steady rental demand in this sought-after area makes this a smart addition to any portfolio.

616 S Jefferson Street, Woodstock

$999,000

12712899 MLS ⋅ ACTIVE Status

Fully Occupied- Premier Downtown Woodstock Investment Opportunity - 8 Residential Units, Commercial Space, and Vacant Lot with 8.5% CAP Rate. A unique and lucrative investment property in the heart of downtown Woodstock, offering a rare combination of immediate rental income, significant tax incentives, and future development potential. This solid brick, multi-family and commercial building, located just off the historic Woodstock Square and steps from the Metra train station. The property includes eight fully occupied one-bedroom, one-bathroom residential apartments, a leased commercial print shop, and a valuable adjacent vacant lot, providing a diverse and stable income stream. Tenants enjoy the convenience of exterior parking, shared laundry facilities, and a dedicated storage area. Located in TIF district & Enterprise Zone.

130 Washington Street, Woodstock

$310,000

3 Beds ⋅ 1 Baths ⋅ 12708900 MLS ⋅ CONTINGENT Status

Experience the charm and comfort of this exceptional farmhouse, which boasts quality construction, beautifully restored details, modern efficiencies, and an impressive 1.7 acres of land. You'll fall in love with the exquisite craftsman woodwork and elegant crown molding, along with the rich hardwood flooring that runs throughout. Step into the inviting front entryway and sunroom, creating a warm and welcoming atmosphere for guests. The spacious living room features soaring ceilings and tasteful crown molding, perfect for relaxation and gatherings. The dining room is ideally situated between the kitchen and living room, showcasing arched doorways that contribute to the home's character and charm. Whip up delicious meals in the kitchen, which features original cabinets and a quaint eating nook that doubles as a coffee bar, all while enjoying views of the sprawling backyard. The updated bathroom adds modern touches, and the first-floor bedroom offers versatility as a master bedroom or home office. Upstairs, you'll find two additional bedrooms filled with natural light that highlights the stunning hardwood floors throughout. Your vehicles will be well taken care of in the detached three-car garage, complete with new concrete flooring. This home is equipped with spray foam insulation for energy efficiency, and the roof was replaced in 2024. The basement is also plumbed for a bathroom, adding to the home's potential. If you desire privacy and the allure of farmhouse living, all with the convenience of town nearby, look no further-this is your dream home waiting for you!

824 Washington Street, Woodstock

$215,000

2 Beds ⋅ 1 Baths ⋅ 12702764 MLS ⋅ CONTINGENT Status

Charming Ranch in a Prime Woodstock Location with an Incredible Backyard! This move-in ready 2-bedroom ranch offers the perfect blend of comfort, updates, and an unbeatable location. Hardwood floors flow throughout much of the home. Large windows fill the home with natural light, creating a warm and inviting atmosphere you'll love coming home to. The true standout is the expansive, nearly one-third acre fenced backyard-a rare find this close to downtown. Whether you envision summer barbecues, gardening, a play area for pets or kids, or simply relaxing in your own private outdoor retreat, this yard offers endless possibilities. A detached one-car garage provides additional storage and convenience. Major updates include: New roof, siding, and gutters on the house (2024), new garage siding and gutters (2024), new garage roof (2023), furnace and central air (2018), Washer and dryer (2023). Close to Woodstock's charming Historic Square, where you'll enjoy locally owned shops, restaurants, seasonal events, farmers markets, and year-round community activities. With the Metra train station just minutes away, commuting to Chicago or exploring the surrounding area couldn't be more convenient.

1019 N Madison Street, Woodstock

$175,000

2 Beds ⋅ 2 Baths ⋅ 12704630 MLS ⋅ CONTINGENT Status

Well-maintained 2 bedroom 2 bath second-floor condo in a desirable Woodstock location, just a short walk to the Historic Woodstock Square with its shops, restaurants, entertainment, and Metra station. This bright unit features hardwood floors, a functional galley kitchen, and a private balcony overlooking mature trees-an ideal spot to relax. The pet-friendly association (per deed restrictions) offers convenient on-site laundry in basement and an assigned parking space. Built in 1965, this condo is perfect for first-time buyers, downsizers, or anyone looking for low-maintenance living close to everything Woodstock has to offer.

207 Fremont Street Unit #3, Woodstock

$400,000

2 Beds ⋅ 1 Baths ⋅ 12708078 MLS ⋅ PENDING Status

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. How about the 40x30 steel outbuilding with a concrete floor and 2 overhead doors for your vehicles? There are also several outbuildings for small animals including a 4-6 stall horse barn area and plenty of pasture area ..Lift the overhead door to the barn for easy access to the horse stalls.... This property is being sold AS-IS condition. A quick closing is possible.

2046 Deep Cut Road, Woodstock

$238,000

2 Beds ⋅ 1 Baths ⋅ 12693617 MLS ⋅ CLOSED Status

STOP THE CAR! Nestled on a CHARMING tree-lined street, this SOLID RANCH offers incredible curb appeal, a 2-CAR GARAGE, and MATURE TREES. Step inside to a LARGE Living Room filled with NATURAL LIGHT and enjoy the GREAT FLOW throughout the home. Whether you're starting out, downsizing, or looking for easy FIRST FLOOR LIVING, this RANCH checks all the boxes. The DRY basement provides AMPLE STORAGE and future potential, while the spacious driveway offers plenty of parking. Recent updates include a NEW FURNACE (2026). Located on a QUIET street, yet just a HOP, SKIP, and JUMP to OLSON PARK and all of Woodstock's wonderful amenities!

111 Meadow Avenue, Woodstock

$1,000,000

12689173 MLS ⋅ ACTIVE Status

`Position your business in one of Woodstock's most recognizable downtown buildings, located in the heart of the Historic Woodstock Square. This well-maintained, mixed-use office building offers an exceptional opportunity for professionals seeking a prestigious business address in a thriving downtown district. The historic property is currently undergoing thoughtful renovations and improvements designed to enhance the tenant experience while preserving the building's timeless architectural character. The building is a proven investment, with the entire first floor and third floor fully leased, providing an established professional environment. The second floor features five private office suites available for lease, offering flexible opportunities for individual tenants or businesses looking to occupy multiple offices. One of the offices may also be utilized as an on-site building management office, making the property ideal for an owner-occupant or property management company. Tenants and clients will appreciate the building's outstanding location just a short distance from the Historic Woodstock Square, home to restaurants, coffee shops, boutiques, banks, professional services, and year-round community events. The property also benefits from abundant free public parking surrounding the Square, providing convenient access without the expense of private parking. For commuters, the property is located only a short distance from the Metra Union Pacific Northwest Line, offering direct rail service between Woodstock and downtown Chicago, making it an ideal location for professionals serving clients throughout the region. Establish your business in one of downtown Woodstock's premier office locations, where historic character, modern functionality, and unmatched accessibility come together to create an exceptional workplace. Contact Main Listing Broker S. Lynn Klotz for more details!

214 Main Street, Woodstock

$222,500

2 Beds ⋅ 1 Baths ⋅ 12689313 MLS ⋅ CLOSED Status

**OFFER DEADLINE JULY 2ND AT 3PM**Opportunity awaits at 658 Pleasant Street! This home is full of potential and ready for your personal touch. Whether you're an investor, rehabber, or buyer looking to build equity, this property offers a fantastic opportunity to make it your own. Recent improvements include a new roof on both the house and detached garage (2026), new garage door (2026), new sump pump (2026), new quartz kitchen countertops (2026), and a new stove (2026). The detached garage provides additional storage and parking, while the home's functional layout offers a great foundation for future updates. Conveniently located just minutes from historic downtown Woodstock, shopping, restaurants, parks, and schools. Bring your ideas and unlock the potential this property has to offer. Being sold as-is.

658 Pleasant Street, Woodstock

$215,000

3 Beds ⋅ 1 Baths ⋅ 12689836 MLS ⋅ CLOSED Status

Charming single-story ranch home perfect for modern living. This beautiful property features three comfortable bedrooms and one well-appointed bathroom. The open layout connects a bright living area to a functional kitchen space. Step outside to find an impressive, spacious backyard ideal for outdoor entertaining, gardening, or relaxing in the sun. The detached two-car garage provides excellent vehicle storage and extra workspace. Located in a friendly, quiet neighborhood close to local amenities, schools, and parks. This move-in ready home offers comfort, convenience, and classic style. Do not miss your chance to own this wonderful piece of real estate.

1415 Walnut Drive, Woodstock

$699,900

5 Beds ⋅ 3 Baths ⋅ 12679135 MLS ⋅ CONTINGENT Status

Imagine The Possibilities - Income Potential, Indoor Storage, Rental Opportunity, Farm Dreams, Or The Ultimate Family Compound. Because TWO Houses Really Are Better Than One! Set On A Sweeping 19.62 Acres Zoned Agricultural (A-1), This Former Dairy Farm Is Move-In Ready To Live, Work AND Play! Perched On The Hill With Country Views In Every Direction, The Property Anchors Around Two Homes. House 1 Is A Character-Rich Farmhouse Brimming With Original Charm: A Vaulted Living Room Anchored By A Floor-To-Ceiling Brick Wood-Burning Fireplace, Original Hardwood Floors, Warm Wood-Plank Ceilings, And Built-In Knotty-Pine Bookshelves, Desk, And A Classic Glass-Paned French Door. The Updated Kitchen Shines With Raised-Panel Wood Cabinetry, Stainless Appliances, Solid-Surface Counters, And A Window Over The Sink Framing Green Country Views. Offering 5 Bedrooms - A First-Floor Primary Plus 4 Bedrooms Up - Generously Sized Rooms, A Full Basement, And A Main-Floor Bath With A Walk-In Closet And Tiled Walk-In Shower, With A Brand-New Tub (credit for installing). House 1 Pairs Farmhouse Soul With Everyday Function. House 2 Is A Comfortable Ranch With A Bright, Open Floor Plan Where The Kitchen - Stainless Appliances, Ample Oak Cabinetry, And A Country-View Window - Flows Into A Spacious Living And Dining Area Filled With Natural Light. It Offers 3 Bedrooms (Including One With A Charming Built-In Knotty-Pine Wardrobe), A Full Bath, And A Full Basement With Finished Bonus Space Below - Ideal For Extended Family, A Tenant, Guest Quarters, Or Rental Income. The OUTBUILDING Of Your Dreams Is A Massive 60 X 160 Barn Built For Serious Use: Soaring Timber-Truss Ceilings, Concrete Floors, Oversized Doors That Swallow Equipment, Trailers, Or An RV, Abundant Lighting, And Even Former Horse Stalls For The Equestrian Buyer. Tucked Inside Is A HEATED Workshop With Overhead Heaters, Work Benches, And A Finished Hangout Space - The Ultimate Hunters' Lodge, Hobby Shop, Or Man Cave. A One-Of-A-Kind Bonus: The Farm's Original Silo Foundation Has Been Repurposed Into A Screened Party Room With Power And Heat, A Vaulted Beamed Ceiling, Cafe Lighting, A Built-In Bar, And Walls Of Windows Overlooking The Woods - Built For Entertaining A Crowd. The Back 10 Acres Are Leased Annually To A Longtime Local Farmer, Providing Built-In Agricultural Use And Income. Recent Updates Include 2021 Roofs And Vinyl Siding. The Property Has A Shared Well Between The Two Homes - Buyers Should Confirm Financing Compliance With Their Lender. So Much To See, So Much To Love In This Rare McHenry County Compound. While Beautifully Maintained, The Property Will Be Sold In As-Is Condition.

18918 Bunker Hill Road, Woodstock

$545,000

3 Beds ⋅ 2 Baths ⋅ 12687756 MLS ⋅ CONTINGENT Status

Beautifully updated 3 Bedroom, 2 Bath Ranch Farmhouse with a 2 car garage, barn and paddock area on almost 12 acres! Conveniently located just East of Woodstock this property features a completely renovated home overlooking the rolling hills of Bull Valley. The foyer leads you into the living room with fresh paint, new flooring, new light fixtures and tons of windows for natural light. There are 3 bedrooms with new flooring, fresh paint and ceiling fans. The first-floor bathroom has been completely redone with new flooring, standup shower, new toilet, lighting and vanity. The kitchen has beautiful views of the country. There is also a full walkup attic that could be easily finished off into additional living space. Downstairs you will find a large family room with fresh carpet, an office with tons of closet storage and another completely updated bathroom. The basement bathroom has a brand new corner shower, toilet, flooring, lighting and vanity. There is also a large laundry room, utility room and storage room. Outside you will find a good sized 2 car garage and a Barn. The barn has 1 stall and is perfect for animals, horses, or storage. The barn has electric, an overhead door in the front and in the back and a large hay loft as well. There is also a smaller well house/shed great for storage or turn it into a chicken shed. The paddock area is fenced with 3 rail vinyl fencing. There are about 10 tillable acres that could be rented out. All this plus a freshly sealed asphalt driveway with side apron parking. **There is a cell tower on the property. All cell tower interest is retained by the seller** The cell tower is in the very corner of the property and has a separate driveway. Verizon will reimburse for a portion of the taxes every year. That currently will be reimbursed yearly to the new owner/buyer.

10105 Il Route 120, Woodstock

$549,900

4 Beds ⋅ 2 Baths ⋅ 12682862 MLS ⋅ CLOSED Status

Experience the beauty and tranquility of rural living, 5 minutes from town, with this one of a kind vintage property. This 1847 farmhouse blends historic charm and modern comforts with exposed bricks, hand hewn wood posts and vintage architectural millwork. The bright kitchen has freshly painted kitchen cabinets, high end appliances and a new honed granite island. In addition to the kitchen adjacent dining room, the first floor features a formal living space with fireplace, a large den, an office with vaulted wood ceilings and a windowed sun room that overlooks the 3 acre property. The first floor bath is huge with marble subway tile, a full tub/shower combo and tons of storage. The second floor feature 4 freshly painted bedrooms, an updated bath with shower and a good sized storage room, as well as a drop down attic. The 3 car garage features paneled walls, with new expoxy flooring. The additional 3 car work space has also been updated with epoxy flooring and added heat for winter projects. Additional garden shed for all of your yard tools. A Gated, raised bed garden and perennial beds add vintage charm to the A-1 zoned , 3 acre property. Don't miss the opportunity to make this vintage charmer your own!

11516 Country Club Road, Woodstock

$399,000

4 Beds ⋅ 2 Baths ⋅ 12652329 MLS ⋅ CONTINGENT Status

Welcome to the ROBERT BEATTY HOUSE. Located at 354 S. Madison Street just a short walk to the the Woodstock Square, known for it's amazing farmers market, boutique shopping, tons of dining, and the movie Groundhog Day! This Victorian home will not disappoint. It has been amazingly maintained, and has so much character! Beautifully restored (2020), wrap-around front porch, And just wait 'til you see all the original woodwork, and stained glass windows. You will be greeted by a Stunning Oak staircase, a lovely foyer, good size formal living room, leading to a large open dining room, with cozy seating area. Main level also boasts a bedroom, that could easily be used as an office, with a full bath close by! Spacious second floor sitting room, plus an unfinished attic, with great potential for future expansion. 3 bedrooms and full hall bathroom on second floor. Just steps away from the house is a huge 3 car garage with second story storage. Tons of additional storage in cellar as well. Deep lot with large, gorgeous backyard. Sellers have also just had a lot of painting updated, inside and out, as well as had furnace and a/c inspected, and put a new thermostat in! Excellent location near Woodstock square, schools, parks, and Metra.

354 S Madison Street, Woodstock

$280,000

4 Beds ⋅ 2 Baths ⋅ 12672206 MLS ⋅ CLOSED Status

This beautifully remodeled Victorian brings all the charm you want with the updates you need. From the moment you step onto the enclosed and heated front porch, this home feels warm, welcoming, and ready for its next chapter. Inside, you'll find updated bathrooms, a refreshed kitchen with a center island, peninsula with breakfast bar, raised panel oak cabinetry, engineered hardwood flooring, double sink, lazy susan cabinet, and great everyday functionality throughout. The home also features a full basement, replaced energy efficient windows throughout, and plenty of space to live, gather, and settle in with ease. Outside, the fenced yard is a true highlight, offering room to relax, entertain, garden, play, or let pets enjoy the space. The large garage adds even more convenience for parking, storage, hobbies, or workshop needs. All of this is tucked in a location close to everything Woodstock has to offer, including the Square, shops, restaurants, parks, schools, and the Metra. Updated, charming, convenient, and move-in ready, this home makes it easy to picture yourself settling in and loving where you live.

421 Center Street, Woodstock

$203,500

2 Beds ⋅ 1 Baths ⋅ 12669235 MLS ⋅ ACTIVE Status

Cozy Two bedroom home with a two car garage. New paint, flooring, cabinets and appliances. Great starter home. New driveway has been installed.

524 Amsterdam Street, Woodstock

$224,900

3 Beds ⋅ 1 Baths ⋅ 12669112 MLS ⋅ CONTINGENT Status

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 chance-schedule your showing today!

110 N Seminary Avenue, Woodstock

$260,000

3 Beds ⋅ 1 Baths ⋅ 12663690 MLS ⋅ CLOSED Status

Highest and Best Due by 5pm on 6/4/26 - Nestled on a SPACIOUS COUNTRY LOT just MINUTES FROM TOWN, AND ZONED A1! This charming RANCH offers peaceful surroundings with neighboring pasture views, LOCAL WILDLIFE, and a quiet setting that feels like an escape from the everyday. Inside, you'll find comfortable living spaces, a functional layout, patio access, and a flexible laundry/mudroom area that adds extra convenience and storage. In 2013, the home underwent EXTENSIVE UPDATES, including electrical, plumbing, HVAC, windows, doors, and exterior wall reconstruction with added foam insulation for efficiency and comfort. A NEW Roof and a NEW Well in 2025, giving buyers peace of mind with many major improvements already completed.

14914 W South Street Road, Woodstock

$235,000

2 Beds ⋅ 1 Baths ⋅ 12663527 MLS ⋅ CLOSED Status

Multiple Offers Received, Highest and Best by Wednesday June 3, 2:00 pm. Charming ranch home in a highly desirable location close to downtown, the historic Square, shopping, restaurants, and the train station. This updated home combines classic character with modern improvements, making it truly move-in ready. Step inside to find updates throughout the entire home, including updated windows, stylish mission-style interior doors, an updated bathroom, and hardwood flooring throughout approximately three-quarters of the home. The bright and inviting floor plan offers comfortable living spaces filled with natural light and timeless charm. The updated kitchen is sure to impress with granite countertops, stainless steel appliances, ample cabinetry, and plenty of workspace for meal preparation and entertaining. Whether you're hosting guests or enjoying a quiet evening at home, this kitchen is both functional and attractive. Outside, you'll find an extra-large fully fenced backyard that provides endless opportunities for outdoor enjoyment. Gather around the firepit with family and friends, create your dream garden, or simply relax in your own private outdoor retreat. The spacious yard offers plenty of room for pets, play, and entertaining. Additional features include a full basement offering abundant storage space and potential for future finishing. The home's convenient location provides easy access to commuter routes, shopping, dining, parks, and community events, making it an ideal place to call home. Don't miss this opportunity to own a beautifully updated home with character, charm, and an unbeatable location. Please note: FHA and VA financing are not available due to the seller's length of ownership.

615 Park Street, Woodstock

$310,000

4 Beds ⋅ 2 Baths ⋅ 12652285 MLS ⋅ CLOSED Status

Welcome home...This lovely 4 bedroom, 2 bath has it all! With it's beautiful real hardwood floors, on the main floor, and it's spacious living room, and kitchen/dining combo...this home is just about perfect! The kitchen boasts plenty of cabinet and counter space, and the door off the kitchen leads to the upper deck overlooking this beautiful,large, fenced in yard. Both baths have been renovated, the upstairs bath has a brand new tub/shower!!! This home also has newer windows, and a beautiful new front door!!! Walkout lower level has new carpeting,and a large family room, cozy bedroom, office space, and a huge laundry room, plus tons of storage and 2nd bath. This extra large lot offers tons of privacy, beauty, and serenity! Walking distance to all schools!

101 W Melody Lane, Woodstock

$399,000

5 Beds ⋅ 4 Baths ⋅ 12660242 MLS ⋅ PENDING Status

645 E Calhoun Street, Woodstock

$195,000

3 Beds ⋅ 2 Baths ⋅ 12659971 MLS ⋅ ACTIVE Status

PROPERTY SOLD "AS IS" WITHOUT REPAIR, Listing Broker & Seller assume no responsibility & make no guarantees/warranties or representations as to the availability or accuracy of the property information, photographs or other information depicted/described herein.. CASH & CONVENTIONAL OFFERS

327 Burbank Avenue, Woodstock

$243,500

4 Beds ⋅ 2 Baths ⋅ 12645782 MLS ⋅ CLOSED Status

645 Pleasant Street, Woodstock

$270,000

2 Beds ⋅ 2 Baths ⋅ 12640398 MLS ⋅ CLOSED Status

Absolutely beautiful remodeled home! New floors , new painting, new kitchen, new appliances, new refrigerator with water/ice maker new faucets and vanities in both bathrooms, new washer and dryer, New electric , new plumbing . All work was done by licensed professionals with city permits and all inspections passed from City of Woodstock. Full finished basement with full bath. Basement has two rooms which could be used as offices, city doesn't qualify those rooms as bedrooms. Large wooden deck and huge backyard with mature trees at the property line for privacy. Currently street parking (Woodstock rules apply). However, Seller can build driveway or offer credit to Buyer at closing.Contractor and price available. Seller will give $150 credit to Buyer at closing to buy microwave of their choice. One of owners is licensed Realtor

147 S Hill Street, Woodstock

$264,000

5 Beds ⋅ 2 Baths ⋅ 12634912 MLS ⋅ CLOSED Status

Looking for your next investment? This two-unit property checks all the boxes! The main unit offers 3 bedrooms, 1 bath, and a nicely updated kitchen with granite countertops. Upstairs, you'll find a 2 bedroom, 1 bath unit ready for rental income. The upstairs unit has a small balcony to enjoy your morning coffee. The oversized lot with mature trees creates the perfect setting for outdoor entertaining and bonfire nights. With a new roof in 2025 and newer furnaces, this property is ready to go! Convenient location near train, stores, entertainment, restaurants and everything else that the charming Woodstock Square offers. Don't miss this great investment! Sold as-is.

612 Oak Street, Woodstock

$340,000

3 Beds ⋅ 2 Baths ⋅ 12624135 MLS ⋅ CLOSED Status

801 S Jefferson Street, Woodstock

$205,000

3 Beds ⋅ 1 Baths ⋅ 12631878 MLS ⋅ CLOSED Status

Great value on this 3-bedroom, 1-bath home offering ranch style living with plenty of potential. Ideal for first-time buyers or investors looking for an affordable opportunity to own or expand their portfolio. Great size living room with hardwood flooring throughout living room and bedrooms, kitchen has table space and plenty of counter space as well. Ceramic flooring in the kitchen. Attached 1 car garage. Enjoy a nice-sized backyard with plenty of space for outdoor activities, pets, or entertaining this coming summer. Situated on the north side of town and within walking distance to schools. Selling As is.

124 E Melody Lane, Woodstock

$296,000

3 Beds ⋅ 3 Baths ⋅ 12558120 MLS ⋅ CLOSED Status

This grand home with a classic wraparound porch is in a prime location close to the Square, schools, and the train station. Inside, you'll appreciate hardwood floors and artistic trim. The inviting parlor showcases one of the home's original beveled glass windows. French doors lead into the formal dining room. The kitchen features vintage built-in cupboards. This home has a flexible floor plan. The main floor includes a bedroom or office. Upstairs, you'll find bedrooms plus a spacious sitting room that could easily be converted into an additional bedroom. A bonus room provides even more potential-ideal for a bedroom, office, or hobby space. There is a full bath on both the first and second floors. Laundry is conveniently located on the main floor. Additional features include a full basement and a two-car attached garage. The home needs TLC and is being sold as-is. The raised bed gardens are a treat, featuring your own herb garden, pollinator gardens, plus rhubarb, asparagus, elderberry, and a cascade of flowers throughout the season. Motivated Seller. Quick closing possible.

319 W South Street, Woodstock

$240,000

3 Beds ⋅ 1 Baths ⋅ 12622097 MLS ⋅ CLOSED Status

Charming all-brick 3-bedroom, 1-bath home full of character! The main level features two comfortable bedrooms, a full bathroom, a welcoming living room, and a spacious dining room highlighted by beautiful built-in corner cabinets-perfect for showcasing your favorite pieces. The kitchen is conveniently located just off the dining room, making entertaining easy. Upstairs, you'll find a private third bedroom along with an expansive bonus room-ideal for a home office, playroom, or creative space. Outside, enjoy a generous backyard with plenty of room for summer gatherings, BBQs, and outdoor fun. A detached 2.5-car garage adds even more value, offering ample space for parking, storage, or hobbies. This home blends classic charm with functional living-don't miss the opportunity to make it yours! home is being sold as-is. all in home appliances stay.

920 N Madison Street, Woodstock

$315,500

2 Beds ⋅ 2 Baths ⋅ 12626501 MLS ⋅ CLOSED Status

This beautifully maintained 2-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience in a friendly, inviting neighborhood. Ideally located just minutes from Woodstock High School, with Emricson Park practically at your doorstep and Woodstock's Historic Downtown Square only a short drive away, you'll love the accessibility to everything this area has to offer. Situated on a prime corner lot, the home features a fully fenced backyard-perfect for pets, play, or outdoor entertaining. Inside, you'll find hardwood floors and tile throughout the main level. Two main-floor bedrooms and a bright sunroom create a cozy yet functional layout. Downstairs, the finished lower level offers incredible versatility with a spacious recreation room, a stylish new bathroom, and an office that can easily double as a third bedroom. The basement bar is a standout feature, ready to host game days and gatherings. Complete with a 2-car garage, this home checks all the boxes for comfortable living and entertaining. Please note that all offers must be submitted by Sunday at 4:00 PM. The seller is requesting each party's highest and best offer.

1118 Blakely Street, Woodstock

$375,000

3 Beds ⋅ 3 Baths ⋅ 12622749 MLS ⋅ CLOSED Status

400 Becking Avenue, Woodstock

$343,000

5 Beds ⋅ 2 Baths ⋅ 12622078 MLS ⋅ CLOSED Status

Well-maintained 5-bedroom, 1.5 bath home set on a spacious 0.35-acre lot with a large, fully fenced backyard-perfect for entertaining, pets, or relaxing in your own private outdoor space. The yard features mature trees, plenty of green space, and an above-ground pool ready for summer enjoyment. The home offers a functional and flexible layout with two bedrooms and a full bath conveniently located on the main floor. Upstairs includes three additional bedrooms and a half bath, providing ample space. Inside, you'll find hardwood floors throughout and a bright, comfortable living area. The enclosed porch creates a great transition space between the home and the attached 2-car garage-ideal for most seasons. Additional highlights include a full basement offering excellent storage or future finishing potential, plus major exterior updates with roof and siding both under 10 years old. With its generous lot, practical layout, and inviting outdoor space, this property is a great opportunity to own a move-in-ready home with room to grow!

937 Wicker Street, Woodstock

$675,000

3 Beds ⋅ 2 Baths ⋅ 12619655 MLS ⋅ CLOSED Status

Beautifully updated 3 Bedroom, 2 Bath Ranch Farmhouse with a 2 car garage, barn and paddock area on almost 12 acres! Conveniently located just East of Woodstock this property features a completely renovated home overlooking the rolling hills of Bull Valley. The foyer leads you into the living room with fresh paint, new flooring, new light fixtures and tons of windows for natural light. There are 3 bedrooms with new flooring, fresh paint and ceiling fans. The first-floor bathroom has been completely redone with new flooring, standup shower, new toilet, lighting and vanity. The kitchen has beautiful views of the country. There is also a full walkup attic that could be easily finished off into additional living space. Downstairs you will find a large family room with fresh carpet, an office with tons of closet storage and another completely updated bathroom. The basement bathroom has a brand new corner shower, toilet, flooring, lighting and vanity. There is also a large laundry room, utility room and storage room. Outside you will find a good sized 2 car garage and a Barn. The barn has 1 stall and is perfect for animals, horses, or storage. The barn has electric, an overhead door in the front and in the back and a large hay loft as well. There is also a smaller well house/shed great for storage or turn it into a chicken shed. The paddock area is fenced with 3 rail vinyl fencing. There are about 10 tillable acres that could be rented out. Finally, there is a cell tower in the very corner of the property. That lease will be transferred to the new owner and with it $1280/mo that easily covers the taxes and then some. All this plus an freshly sealed asphalt driveway with side apron parking.

10105 Il Route 120, Woodstock

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