Browse All Woodstock IL 6+ Bedroom Properties for Sale

6 Beds ⋅ 5 Baths ⋅ 12703208 MLS ⋅ ACTIVE Status

Spacious investment opportunity nestled within a charming vintage Victorian home in Historic Woodstock IL. This unique property offers a desirable layout, 3 bedrooms on first floor and 3 bedrooms on second floor. The property includes a 1 car garage and sits on a generously sized lot, offering additional possibilities for outdoor improvements or expansion. With its classic architectural character, this property presents an excellent value-add opportunity for investors or rehabbers looking to restore and enhance its full potential. Property requires work and is being sold in AS IS condition. Room sizes are estimates. No surveys or disclosures will be provided, and taxes will be prorated. Bring your vision and creativity, this is a fantastic chance to transform a historic property into a standout investment. Buyer responsible for any and all building code violations.

212 S Tryon Street, Woodstock

$5,995,000

7 Beds ⋅ 13 Baths ⋅ 12681901 MLS ⋅ ACTIVE Status

Glacier's End Mansion! A Once-in-a-Lifetime Opportunity to Own One of Illinois' Most Extraordinary Private Estates. Welcome to Glacier's End Mansion, an unrivaled move in and turnkey luxury estate encompassing more than 19.3 private acres of impeccably landscaped grounds. Following an extensive, multi-year and multi-million-dollar renovation completed in 2026, this remarkable property is one of the most sophisticated and comprehensively appointed residences ever offered in Illinois. Beyond one of two private gated entrances, a world-class estate unfolds. A private stocked lake, miles of paved trails, creeks, wildlife, a helipad, illuminated roadways, dramatic water features, manicured grounds, and resort-style amenities create an experience rarely found in a private residence. At the heart of the property stands a magnificent limestone and brick mansion offering over 23,000 square feet of refined living space served by two elevators designed to satisfy the most discerning buyer. The estate is handicap friendly, safety and security rivals some of today's most secure environments. A circular, illuminated drive accented by cascading waterfalls and fire features leads to a grand courtyard entrance where soaring ceilings and breathtaking floor-to-ceiling windows frame panoramic views of the lake and resort-style pool complex. Every detail reflects exceptional craftsmanship, including a new custom roof w/ copper accents, more than 200 new custom windows and doors, designer lighting, smart-home integration, 12 independently controlled heating and cooling systems. The estate's outdoor amenities rival those of a luxury resort. Enjoy a spectacular swimming pool w/ pool house featuring rock waterfalls, deck jets, diving board, underwater vacuum system, spa w/ fountain and sport jets, private sand beach, bocce court, basketball court, shooting range, walking and go-cart trails, helipad, expansive recreational grounds designed for both relaxation and entertainment. Inside, elegant formal and casual spaces blend timeless architecture w/modern luxury. The handsome library w/office showcases custom millwork, built-in bookcases, multi person custom desk, fireplace, concealed sliding doors. The grand living and dining rooms flow seamlessly into the breakfast area, gourmet kitchen, butler's pantry. Anchoring the kitchen is an extraordinary center island w/ seating for up to 16 guests, surrounded by extensive custom cabinetry and hidden storage solutions. Dramatic oval & straight overlooks w/ custom glass railings ascend through the home, creating a striking architectural centerpiece. The luxurious primary suite serves as a private retreat, featuring lake and pool views, French doors to a private balcony, dual custom dressing rooms, wet bar, a spa-inspired bath w/ soaking tub, oversized shower. Four additional ensuite bedrooms are arranged around a central private gathering space that enjoys access to multiple balconies, overlooking the grounds, lake, and pool. This space also has a stocked wet-bar w/counterspace, appliances. Two separate guest or staff residences provide exceptional flexibility for extended family, guests, or household personnel. Each separated w/a grand foyer, private access. Additional amenities:13 bathrooms, Multiple storage rooms, Pool House, 4 kitchens, Banquet kitchen, entertaining areas, Massive fitness center, Indoor hot tub,10-15 person sauna, Red light therapy room, Home theater w/ Dolby Atmos surround sound, Wine room, Game rooms, Central entertainment bar, Multiple laundry facilities, commercial-scale laundry room, Security operations center, Communications room, Panic rooms, Extensive mechanical and utility infrastructure, Heated/cooled garage space for approximately 25-30 vehicles, RVs, vehicle museum showroom. Representing an investment estimated to exceed $30 million to replace. Glacier's End Mansion offers an extraordinary opportunity to acquire a truly turnkey estate at a fraction of its replacement cost.

19802 Dunham Road, Woodstock

$995,000

6 Beds ⋅ 5 Baths ⋅ 12671539 MLS ⋅ ACTIVE Status

Stunning Luxury Estate on 10.12 Acres - A Rare Opportunity - BRAND NEW Driveway!! Experience the perfect blend of elegance, comfort, and country living in this remarkable estate, nestled on over 10 acres of beautifully maintained land. Boasting more than 8,000 square feet of finished living space, this impressive home features 9 spacious bedrooms and 5 full bathrooms-offering an ideal retreat for large families, multigenerational living, or hosting guests in style. Step inside to be welcomed by elegant flooring and a thoughtfully designed layout. The main level includes a private in-law suite and a generously sized laundry room for ultimate convenience. At the heart of the home, the chef's kitchen delights with abundant cabinetry, expansive counter space, high-end stainless steel appliances, and a sun-drenched breakfast area. Relax and unwind in one of two cozy family rooms, each with its own fireplace. The luxurious primary suite is a true sanctuary, featuring a private sitting room, dual walk-in closets, and a spa-inspired en-suite bath with a whirlpool tub, dual vanities, and an oversized shower. The fully finished basement is designed for entertaining, offering a full bar, a billiards room, and two additional bedrooms. Radiant flooring in both the basement and the fully finished 3-car garage ensures year-round comfort. Zoned AG-2, the property allows for horses and livestock, providing a true country lifestyle with modern luxury. Enjoy outdoor living with a brand-new deck, a cozy backyard fire pit, and plenty of space for recreation or future additions. This exceptional estate offers the rare combination of expansive land, luxurious amenities, and a flexible layout to meet your family's needs. Discover your dream home where comfort meets countryside charm.

16512 Nelson Road, Woodstock

$369,000

6 Beds ⋅ 2 Baths ⋅ 12678331 MLS ⋅ CLOSED Status

Really nice 2 flat with 2 car garage. Each unit has 3 bedrooms. Newer roof, siding, windows, kitchens, appliances, furnaces, and water heater. Both units were rented for $1590/ month. Rents were low. Upstairs should be $1800 and downstairs $1700. Upstairs has covered deck and fireplace.

1238-1240 Thomas Drive, Woodstock

$325,000

6 Beds ⋅ 2 Baths ⋅ 12668234 MLS ⋅ CLOSED Status

Excellent investment opportunity or owner-occupant property! This side-by-side duplex features two spacious 3-bedroom units, each offering comfortable living space and practical layouts. Both units have been updated with newer laminate flooring. Each unit has 3 bedrooms and a full bath upstairs. The lower levels include large combined living and dining space, kitchen and laundry room with sink. The walkout lower levels also offer additional flexibility and direct access to separate, fenced backyards-perfect for outdoor enjoyment, pets, or entertaining. Conveniently located in Woodstock with easy access to shopping, dining, parks, and commuter routes. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this duplex is a fantastic opportunity. Rents could be increased. Long term tenants are at below market. Property currently assessed over $365,000. Taxes will be appealed and should be reduced for 2026.

1952-1954 Sheila Street, Woodstock

$27,000,000

11 Beds ⋅ 15 Baths ⋅ 12584038 MLS ⋅ ACTIVE Status

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

$380,000

6 Beds ⋅ 2 Baths ⋅ 12423045 MLS ⋅ CLOSED Status

Side by side 2 flat in a good south side location only a few blocks to schools, the Square, shops, dining, theater and train station. Each side has living room and dining room with newer laminate flooring. Kitchen with pantry closet, oven, refrigerator and dishwasher. Each side has an enclosed porch at the front of the house. Upstairs there are 3 bedrooms and full bath. Each side has its own separate basement for storage and washer and dryer included. The 2 apartments have separate gas forced air heat and water heaters. The roof was replaced in 2017 and windows in 2021 (except enclosed porch). Tenants pay all utilities; gas, electric, sewer, water and garbage. Both apartments have patio and backyard space. One side is currently rented. One side is vacant. You can live in one side and have the other for income or bring in your own tenant and set your own rent. On site parking for 4 cars, 2 cars each apartment. Owner is licensed real estate agent.

415 Dean Street, Woodstock

$760,000

6 Beds ⋅ 5 Baths ⋅ 12397553 MLS ⋅ CLOSED Status

The Details are in the Design. Too many amazing architectural design features to completely list out- reclaimed hardwood throughout, 200 year old Vintage beam for the mantel, mahogany entertainment center cabinets, circa 1880s antique store counter with marble, Tasmanian Green granite, a full dog wash station, 2 laundry rooms for convenience the list goes on and on. 4 bedrooms upstairs with 3 full bathrooms, all en-suite. Owners suite has an semi private step up entrance from the hallway with one of the 5 fireplaces, full finished walkout basement with 2 additional bedrooms and a full bathroom. Media Room with walkout private patio, Workout room, lots of storage. Less than 5 minutes to Metra and the Historic Woodstock Square with nightlife and cute shops. Walking path to elementary school. Surrounded by a wooded area with creek owned by HOA.

1415 Oakview Terrace, Woodstock

$530,000

6 Beds ⋅ 3 Baths ⋅ 12367519 MLS ⋅ CLOSED Status

Great location. This traditional 2 story home is on 6+ acres close to town. It has 6 bedrooms including one on the main floor with full bath. The bedroom on the first floor could also make a good office. The home has hardwood floors. The family room with fireplace opens out to the patio, deck and backyard. The partially finished basement gives you even more living space. For convenience the laundry room is on the main floor. Come see what country living is like. This is an estate sale and being sold as-is.

15909 W South Street Road, Woodstock

$360,000

6 Beds ⋅ 2 Baths ⋅ 12305656 MLS ⋅ CLOSED Status

Great investment opportunity!! Side by side duplex each with 3 beds, 1 bath, attached 1 car garage, 1 extra parking spot each unit, private back patio area. Both sides currently rented. One side has been fully rehabbed last year. The other side has had the same tenant for 30 years. Great location near the courthouse and the Square. Great schools. Excellent opportunity!!!

600-602 St. Johns Road, Woodstock

$400,000

6 Beds ⋅ 4 Baths ⋅ 12282536 MLS ⋅ CLOSED Status

ALL BRICK RANCH Duplex for Sale! Each unit has 3 bedrooms and one full bath, sliding glass doors off the kitchen eating area to small deck plus one car garage with opener and unfinished basement with additional completed full bath. Each unit has updated kitchen and main floor bath. All flooring replaced with luxury vinyl. All new or newer stainless steel appliances including dishwasher, gas stove, refrigerator and built-in microwave and double bin stainless steel sink. Furnace, A/C and hot Water Heater in 722 replaced approximately 2 years ago. Furnace and A/C replaced in 724 in 2024. Unit 724 has fenced yard. Washer and Dryer in each unit are as-is but believed to be in working condition. Garage Heater does not work. All separate utilities. 2460 Total Square Footage. Property being sold as-is.

722-724 Washington Street, Woodstock

$320,000

6 Beds ⋅ 2 Baths ⋅ 12262474 MLS ⋅ CLOSED Status

GREAT opportunity to own a duplex in Woodstock! Each unit has 3 bedrooms, 1 full bath with full size washer & dryer, spacious Living Room and nice size kitchen with separate table space. Large deck off kitchen in upper unit and large yard too! Live in one, rent the other or make it a great investment and rent both for a good cash flow, Both units are currently rented for immediate income and tenants would like to stay. Enjoy 6 panel doors, one car garage for each unit and all utilities are separate. In the past 5 years: Roof, both Hot Water Heaters, both Furnaces and both A/C units replaced. Being sold "As-Is".

1273-1275 Wicker Street, Woodstock

$375,000

6 Beds ⋅ 2 Baths ⋅ 12221731 MLS ⋅ CLOSED Status

Beautifully updated side-by-side duplex featuring 3 bedrooms and 1 bath in each unit, just a short walk from downtown Woodstock. Each unit showcases a modern kitchen with quartz countertops, stainless steel appliances, and brand-new flooring throughout. The main level offers spacious living and dining areas, while the upper level includes a stylishly renovated bathroom and access to a large attic via the primary bedroom's walk-in closet. Full basements provide separate laundry facilities and plenty of storage space. Perfect for investors or those seeking owner-occupied living with rental income potential. Conveniently located near the Square and Metra.

229-231 Mchenry Avenue, Woodstock

$640,000

6 Beds ⋅ 5 Baths ⋅ 12201346 MLS ⋅ CLOSED Status

Rare opportunity to move into the Bull Valley Country Club at an affordable price! A beautiful, private neighborhood of custom homes on spacious lots, with no HOA fees! Located just minutes to downtown Woodstock Historic Square, train, farmer's markets, 10 minutes to Crystal Lake and 20 minutes to Randall Road shopping! Move in now and update over time as you wish, while building equity among million+ dollar homes. Sellers had exciting plans for complete renovations, but it's time to move again! Several big ticket items have been updated, including an $80,000 architectural shingle roof, limestone washed exterior, newer multi zoned HVAC, refinished hardwood floors, modernized SS appliances, custom window shades, professional landscaping and more! If you are drawn to a quiet acre sized property, come take a look at this peaceful setting tucked into a private bend of Bobolink Circle. With 5/6 bedrooms (1st floor bedroom is currently the Den), 5 baths, an enormous 44' x 22' heated garage with volume ceilings and 3 car drive in capacity, and finished walk out basement, this home can meet your needs now and well into the future. The first floor offers in-law or WFH accommodations with a handsome Den/BR5 and nearby full bath. Spacious gourmet kitchen with granite counters, upgraded SS appliances and open family room feature a rear 2nd floor staircase for your daily convenience! Formal Living and Dining Rooms offer flexibility as you choose to use them. The second floor offers a sprawling master suite with dual walk in closets, sitting room ideal for exercise or study, spa like bath with dual vanities and a walk-in roman multi-spray shower! 3 additional generously sized bedrooms, each with an adjacent bath! The finished basement offers room for additional expansion with two large unfinished storage rooms, full bath, rec room and 6th bedroom! If you love outdoor living space, the multi tier deck, flagstone patio, and 1 acre yard will cater to all your backyard needs. This is the chance to move up that you've been waiting for!

1548 Bobolink Circle, Woodstock

$307,000

6 Beds ⋅ 3 Baths ⋅ 12130210 MLS ⋅ CLOSED Status

Welcome Home! This property offers 6 bedrooms, 2.5 bathrooms, and a 2-car garage. This property can be used as a Duplex.

347 Washington Street, Woodstock

$430,000

6 Beds ⋅ 4 Baths ⋅ 11993601 MLS ⋅ CLOSED Status

Step into this stunning brick home nestled in a charming neighborhood of Woodstock, and be ready to fall in love! As you enter, you'll be greeted by the beautiful two-story family room, complete with a striking fireplace framed by floor-to-ceiling windows. The seamless flow leads you to the inviting eat-in kitchen, boasting granite counters, stainless steel appliances, and ample cabinetry, including a convenient pantry. The main level primary suite is a sanctuary of luxury, featuring a tray ceiling, two walk-in closets, and a spa-like bath with a whirlpool tub, separate shower, and dual vanities. On the other side of the home lies a versatile space perfect for an in-law arrangement or home office, complete with a full bath. Entertaining is a breeze with the separate dining room, while the main level laundry room adds practicality to everyday living. Upstairs, discover a fantastic great room offering endless possibilities for leisure and recreation. Two bedrooms, one with an attached hall bath featuring a dual sink vanity and separate shower/water closet, complete the upper level. Descend to the full walkout basement and be amazed by the vastness of this home! The expansive rec room is ideal for gatherings, boasting laminate flooring, recessed lighting, and a movie screen, with easy access to the paver patio. Two additional bedrooms, another full bath with walk-in shower, and abundant storage round out the basement. Special features include: hardwood floors throughout the main level with a custom inlay in the foyer, a freshly painted deck overlooking the lush half-acre yard, and a three-car garage. Updates such as a new furnace - '19, a/c - '21, fridge '23 and roof - '16 provide peace of mind. Situated just minutes from the historic Woodstock Square, Emricson Park, and Woodstock Water Works, this home offers both elegance and practicality. Seller is conveying the property as-is and prefers a closing at the end of May. Don't miss the opportunity to make this exquisite residence your own!

951 Dakota Drive, Woodstock

$370,000

6 Beds ⋅ 4 Baths ⋅ 12004914 MLS ⋅ CLOSED Status

Well maintained townhouse style duplex with 5 car garage. Live in 1 unit and rent out the other. Brand new roof just installed, furnaces and central air units only 4 years old. Paved drive. Tenants are month to month. Well below market rents, units should rent for $1600/month plus extra income from garages.

847-849 Rhodes Street, Woodstock

$460,000

6 Beds ⋅ 3 Baths ⋅ 11997431 MLS ⋅ CLOSED Status

12218 Cooney Drive, Woodstock

$556,000

8 Beds ⋅ 6 Baths ⋅ 11976950 MLS ⋅ CLOSED Status

Calling all Investors, this is a FIND! Built in 1989, this vinyl-sided, four-unit rental building features large apartments, each with a one car attached garage and laundry hook ups, three with unfinished basements. 2nd floor unit has sliding glass doors to balcony from Family Room and Primary Bedroom. The roof and many other items replaced in past 10 years. One unit remodeled a couple years ago with new flooring, paint, etc. Great income generating property. All units are rented, 3 of 4 leases expire Dec 2024, other expires June 2024. One receives 75% of rent through McHenry County Housing Authority. All utilities paid by tenants. Listing agent must accompany, 24 notice required for showings, tenants working from home.

760-766 Pleasant Street, Woodstock

$930,000

6 Beds ⋅ 6 Baths ⋅ 11957560 MLS ⋅ CLOSED Status

You MUST see this gorgeous, unique, custom home on the most serene 9.23 acre lot w/ natural swimming pond! You are welcomed to this stately home w/ the winding, light-lined driveway leads up to the house & continue on to the front door on the beautiful paver walkway surrounded by professional landscaping. Inside you will find ample space to elegantly entertain in the chef's kitchen w/ huge island, high-end SS appliances, granite counters, 2 eat-in areas & formal dining room. Cozy up by one of two wood burning fireplaces or relax in the great room with incredible views of the pond & the serene setting! The main level also has a formal living room, sitting room & handicap accessible bedroom & full bathroom w/ hardwood floors throughout. On the second floor, the primary bedroom is an entire wing of privacy & amenities: featuring newer hardwood floors (2021), a bonus room (office/nursery/workout room), 2 WIC's w/ organizers, electric/blackout shades & Full 5-piece en-suite bathroom w/ jetted tub & spa-esque shower. 2nd level features 4 additional bedrooms w/ WIC's & 2 full bathrooms. Belly up to the bar in the finished basement rec room w/ projector screen & half bath. The house has newer roof (2021), newer hot water heater (2021), UV water filtration (2021) & softener, multiple zones for air & heating, baseboard heating for moist hot air, forced air conditioning (3 newer units 2021). Heated 4+ car garage w/ drains in each bay & electric car charging station connected to house through the large 1st floor laundry/mudroom w/ newer washer & dryer (2023). Natural swimming pond maintained by plants & nature sits just beyond your back door w/ many outdoor patio, entertainment areas. Beyond the garage is a paved basketball court/RV storage area or build site for outbuilding. Yard is rolling & wooded w/ trails leading to the lake (access to lake available w/ optional HOA). Best of both worlds w/ country setting but minutes away from the Historic Woodstock Square, shopping, Metra & RT47.

3111 Alden Road, Woodstock

$445,000

6 Beds ⋅ 4 Baths ⋅ 11934564 MLS ⋅ CLOSED Status

1004 Wintu Court, Woodstock

$224,900

6 Beds ⋅ 3 Baths ⋅ 11874671 MLS ⋅ CLOSED Status

Fully rented side by side 2 flat. 4 bed/2 bath and 2 bed/1 bath. Long term tenants would like to stay. 2 bedroom is month to month. 4 bedroom is Section 8 with majority of rent paid by Housing Authority. Owner pays water and garbage. Tenants pay gas and electric. Both sides have central air. Each side has one garage bay. Property needs work and is being sold as-is.

1262 Thomas Drive, Woodstock

$2,350,000

7 Beds ⋅ 12 Baths ⋅ 11863851 MLS ⋅ CLOSED Status

Glaciers End Estate, sophisticated, sleek, stunning. Noteworthy grand masterpiece of extraordinary quality construction & design. 20 wooded rolling acres, winding paved trails, stocked pond, waterfall and pool. Resort style living at it's finest. Perfect for corporate events. All in suite bedrooms+2nd living quarters. Well appointed European gourmet kitchen complemented by 3 additional kitchens. Two elevators. Helipad option. One of a kind property!

19802 Dunham Road, Woodstock

$390,000

6 Beds ⋅ 5 Baths ⋅ 11792545 MLS ⋅ CLOSED Status

416 Clay Street, Woodstock

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