Woodstock, IL Homes

• 

  

  

  /157

  $27,000,000

  • 11 Beds
  • 15 Baths
  • 12,000 Sq Ft

  Unlisted Address

  Midwest's premier ~490-acre secluded private estate, just 50 miles from Chicago's O'Hare Airport in northern McHenry County, Illinois. A visionary transformation of former farmland, with over 1M cubic yards of earth moved to create rolling hills, dramatic mounds, engineered lakes, restored prairies, mature woodlands, and park-like landscapes. 20K+ planted hardwoods, evergreens, fruit trees, and

  Nicholas Mason Hayden Outdoors LLC

  Unlisted Address
• 

  

  

  /66

  $919,560

  Sold Dec 30, 2025

  16306 Kishwaukee Valley Rd, Woodstock, IL 60098

  • 3 Beds
  • 3 Baths
  • 5,000 Sq Ft
  • Built 1980

  Last Sold Summary

  • 11% Above List Price
  • $184/SF
  • 151 Days On Market

  Current Estimated Value $646,925

  Last Listing Agent Regina Perkins Brokerocity Inc

  16306 Kishwaukee Valley Rd, Woodstock, IL 60098
• 

  

  

  /4

  Est $263,109

  Not Listed For Sale

  1262 Thomas Dr, Woodstock, IL 60098

  • 6 Beds
  • 3 Baths
  • Built 1974

  1262 Thomas Dr, Woodstock, IL 60098

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /20

  $429,180

  New Construction $24K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,063 Sq Ft

  3859 Meadowridge Rd, Woodstock, IL 60098

  SPECIAL FINANCING OFFERS AVAILABLE! READY FOR NOVEMBER DELIVERY! Homesite# 0088. Experience the Meadowlark model, a masterfully designed two-story home combining style and convenience. With four bedrooms, two bathrooms, and a powder room, this home offers the perfect space for modern living. The first floor features a bright, open-concept layout, with a spacious family room, accessible dining

  Bill Flemming HomeSmart Connect LLC

  3859 Meadowridge Rd, Woodstock, IL 60098
• 

  

  

  /6

  $50,000

  Sold Nov 17, 2025

  Lot #18 Oakmont Dr, Woodstock, IL 60098

  • Land
  • 1.47 Acres
  • $34,014 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 976 Days On Market

  Last Listing Agent Stephanie Berry Berkshire Hathaway HomeServices Starck Real Estate

  Lot #18 Oakmont Dr, Woodstock, IL 60098
• 

  

  /34

  Est $407,143

  Not Listed For Sale

  722 Washington St, Woodstock, IL 60098

  • 6 Beds
  • 4 Baths
  • 2,460 Sq Ft
  • Built 1990

  722 Washington St, Woodstock, IL 60098

  Last Sold Summary

  • 2 Days On Market
• 

  

  /19

  $69,900

  • 6 Beds
  • 5 Baths
  • 3,716 Sq Ft

  212 S Tryon St, Wood Stock, IL 60098

  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

  Michael Olszewski Area Wide Realty

  212 S Tryon St, Wood Stock, IL 60098
• 

  

  /26

  $272,000

  Sold Mar 12, 2026

  3165 Shenandoah Ln, Woodstock, IL 60098

  • 3 Beds
  • 2.5 Baths
  • 1,373 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $198/SF
  • 4 Days On Market

  Current Estimated Value $269,973

  Last Listing Agent Bob Panek CENTURY 21 New Heritage

  3165 Shenandoah Ln, Woodstock, IL 60098
• 

  

  /10

  Est $519,572

  Not Listed For Sale

  2301 Mustang Trail, Woodstock, IL 60098

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 2004

  2301 Mustang Trail, Woodstock, IL 60098

  Last Sold Summary

  • 37 Days On Market
• 

  

  /42

  $217,500

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,268 Sq Ft

  2456 Bridgewater Dr, Woodstock, IL 60098

  Welcome to 2456 Bridgewater - a spacious 2-story townhome offering 2 bedrooms, 1.5 bathrooms, and an attached 1-car garage. This home features a functional layout with great natural light and generously sized rooms throughout. The kitchen opens to the dining area. Upstairs, you'll find two spacious bedrooms and a full bath. This property needs TLC and presents a fantastic opportunity to bring

  Katherine Vences RE/MAX Mi Casa

  2456 Bridgewater Dr, Woodstock, IL 60098
• 

  

  /43

  $230,000

  Sold Jun 30, 2025

  1077 Castleshire Dr Unit 1077, Woodstock, IL 60098

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft
  • Built 2000

  Last Sold Summary

  • $194/SF
  • 10 Days On Market

  Current Estimated Value $231,742

  Last Listing Agent Karen Streelman eXp Realty

  1077 Castleshire Dr Unit 1077, Woodstock, IL 60098
• 

  

  /58

  Est $637,932

  Not Listed For Sale

  616 Indian Trace, Woodstock, IL 60098

  • 4 Beds
  • 4.5 Baths
  • 3,220 Sq Ft
  • Built 2007

  616 Indian Trace, Woodstock, IL 60098

  Last Sold Summary

  • 13 Days On Market
• 

  

  /30

  $890,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 6,280 Sq Ft

  1546 Bobolink Cir, Woodstock, IL 60098

  Elegant custom home with all the extras...including an elevator and extended family quarters. Large, true gourmet kitchen, built-ins, coffered ceilings, plantation shutters, 4 fireplaces and hardwood flooring. New carpeting and fresh interior neutral paint. Enjoy the first floor primary bedroom with sliding doors onto the private deck and backyard. Two first floor offices, heated floors in the

  Sue Perdue Baird & Warner

  1546 Bobolink Cir, Woodstock, IL 60098
• 

  

  /22

  $392,000

  Sold Apr 17, 2026

  2732 Woodworth Ave, Woodstock, IL 60098

  • 3 Beds
  • 4 Baths
  • 1,988 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $197/SF
  • 69 Days On Market

  Current Estimated Value $399,479

  Last Listing Agent Katlyn Draftz Keller Williams Success Realty

  2732 Woodworth Ave, Woodstock, IL 60098
• 

  

  /22

  Est $268,728

  Not Listed For Sale

  701 Washington St, Woodstock, IL 60098

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft
  • Built 2005

  701 Washington St, Woodstock, IL 60098

  Last Sold Summary

  • 2 Days On Market
• 

  

  /3

  $836,000

  • 4 Beds
  • 2 Baths

  16212 Nelson Rd, Woodstock, IL 60098

  Fantastic opportunity in desirable Woodstock location! This house has great potential! SOLD AS IS, SIGHT UNSEEN. DO NOT DISTURB OCCUPANTS. BEDROOM AND BATHROOM COUNT IS APPROXIMATE. BUYER WILL HAVE NO ACCESS. OCCUPANTS SHOULD NOT BE CONTACTED. ROOM COUNT AND SIZES UNKNOWN. LOT SIZE APPROXIMATE. SELLER AND LISTING BROKER HAVE NOT BEEN INSIDE THE HOME.

  Patti Furman Coldwell Banker Realty

  16212 Nelson Rd, Woodstock, IL 60098
• 

  

  /4

  $443,110

  Sold Apr 16, 2026

  3920 Riverwoods Dr, Woodstock, IL 60098

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 6% Below List Price
  • $226/SF
  • 74 Days On Market

  Lennar Riverwoods - Single Family

  3920 Riverwoods Dr, Woodstock, IL 60098
• 

  

  /18

  Est $225,715

  Not Listed For Sale

  1400 Oakleaf Ln, Woodstock, IL 60098

  • 2 Beds
  • 1.5 Baths
  • 1,366 Sq Ft
  • Built 1989

  1400 Oakleaf Ln, Woodstock, IL 60098

  Last Sold Summary

  • 37 Days On Market
• 

  /2

  $49,000

  • Land
  • 2.59 Acres
  • $18,919 per Acre

  11100 Mcconnell Rd, Woodstock, IL 60098

  About half of property is buildable, balance has water feature. Some mature trees.

  Gary Lechner Hometown Realty, Ltd.

  11100 Mcconnell Rd, Woodstock, IL 60098
• 

  /2

  $910,000

  Sold Feb 26, 2026

  17515 Deep Cut Rd, Woodstock, IL 60098

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Below List Price
  • $303/SF
  • 4 Days On Market

  Current Estimated Value $905,431

  Last Listing Agent Elise Livingston RE/MAX Plaza

  17515 Deep Cut Rd, Woodstock, IL 60098
• 

  

  /13

  Est $300,883

  Not Listed For Sale

  2010 Joseph St, Woodstock, IL 60098

  • 3 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Built 1990

  2010 Joseph St, Woodstock, IL 60098

  Last Sold Summary

  • 4 Days On Market
• 

  

  /12

  $254,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,765 Sq Ft

  863 Pleasant St, Woodstock, IL 60098

  This bi-level home offers genuine potential in Woodstock. With five bedrooms and three bathrooms, the layout provides flexibility for residents, remote workers, or investors exploring rental opportunities. The structure and lot size create a solid foundation for buyers ready to personalize the space. Positioned in an established area, this property presents an opportunity to build equity through

  Frank DeNovi Compass

  863 Pleasant St, Woodstock, IL 60098
• 

  

  /25

  $375,000

  Sold Jul 30, 2025

  411 N Madison St, Woodstock, IL 60098

  • 4 Beds
  • 2 Baths
  • Built 1890

  Last Sold Summary

  • 6% Below List Price
  • 15 Days On Market

  Current Estimated Value $374,675

  Last Listing Agent Socorro Sanchez 103 Realty LLC

  411 N Madison St, Woodstock, IL 60098
• 

  

  /29

  Est $252,152

  Not Listed For Sale

  219 Hoy Ave, Woodstock, IL 60098

  • 3 Beds
  • 1.5 Baths
  • 1,294 Sq Ft
  • Built 1900

  219 Hoy Ave, Woodstock, IL 60098

  Last Sold Summary

  • 1 Day On Market
• 

  

  /11

  $270,000

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft

  266 Hutchins Ct, Woodstock, IL 60098

  Rare opportunity to own a historic property located at the former site of the Emerson Typewriter Co. Upscale, stylish and modern design with historic charm. Dramatic vaulted ceilings with timber beams. Vintage exposed brick, private entrance, solid knotty pine doors, end unit with additional windows. Walk to Woodstock Square and train.

  Frank Zizzo Baird & Warner

  266 Hutchins Ct, Woodstock, IL 60098
• 

  

  /31

  $353,000

  Sold Feb 20, 2026

  9221 Dirkshire Dr, Woodstock, IL 60098

  • 4 Beds
  • 3.5 Baths
  • 3,218 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $110/SF
  • 63 Days On Market

  Current Estimated Value $411,038

  Last Listing Agent Carrie DuMelle Weichert Realtors - Tovar Prop

  9221 Dirkshire Dr, Woodstock, IL 60098
• 

  

  /11

  Est $303,542

  Not Listed For Sale

  1818 Woodside Dr, Woodstock, IL 60098

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 2009

  1818 Woodside Dr, Woodstock, IL 60098

  Last Sold Summary

  • 2 Days On Market
• 

  

  /30

  $2,400,000

  • Land
  • 60.64 Acres
  • $39,578 per Acre

  10015 Il Route 120, Woodstock, IL 60098

  Situated at a pivotal bend of IL 120 north of historic Woodstock, this 60.64-acre site with ~3,700 ft roadway frontage invites vision for commercial space, residential subdivision, mixed use community, or multi-family development. Currently zoned agricultural with homestead and several outbuildings, the acreage has been conceptually configured into 8 parcels: five 5 acres parcels, one 8 acre

  Emily Smith Berkshire Hathaway HomeServices Starck Real Estate

  10015 Il Route 120, Woodstock, IL 60098
• 

  

  /13

  $315,000

  Sold Jun 30, 2025

  1817 Yasgur Dr, Woodstock, IL 60098

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $214/SF
  • 69 Days On Market

  Current Estimated Value $313,900

  Last Listing Agent Richard Toepper Keller Williams Success Realty

  1817 Yasgur Dr, Woodstock, IL 60098
• 

  

  /49

  Est $588,617

  Not Listed For Sale

  11201 Dorham Ln, Woodstock, IL 60098

  • 3 Beds
  • 3 Baths
  • 2,817 Sq Ft
  • Built 2003

  11201 Dorham Ln, Woodstock, IL 60098

  Last Sold Summary

  • 121 Days On Market
• 

  

  /46

  $399,900

  Pending

  • 4 Beds
  • 2.5 Baths

  602 Hickory Rd, Woodstock, IL 60098

  Experience refined ranch-style living in this beautifully maintained home, ideally situated on an expansive corner lot in Woodstock. Thoughtfully designed for both comfort and functionality, the home offers a seamless blend of open-concept living and flexible spaces suited for today's lifestyle. The main level is highlighted by warm hardwood flooring, multiple living areas, a dedicated dining

  Keith Brand Berkshire Hathaway HomeServices Chicago

  602 Hickory Rd, Woodstock, IL 60098
• 

  

  /18

  $396,600

  Sold Jan 28, 2026

  3839 Riverwoods Dr, Woodstock, IL 60098

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $218/SF
  • 58 Days On Market

  Lennar Riverwoods - Single Family

  3839 Riverwoods Dr, Woodstock, IL 60098
• 

  

  /10

  Est $177,271

  Not Listed For Sale

  1129 Greenwood Cir Unit 6B, Woodstock, IL 60098

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1992

  1129 Greenwood Cir Unit 6B, Woodstock, IL 60098

  Last Sold Summary

  • 45 Days On Market
• 

  

  /19

  $164,900

  • 2 Beds
  • 1 Bath
  • 801 Sq Ft

  501 Leah Ln Unit 1A, Woodstock, IL 60098

  Spacious & rare two bedroom condo on the first floor in a very well maintained complex. Newer engineered wood throught the whole unit. The well designed layout features a large living room that opens to patio & seperates the bedrooms. This great condo comes with one private parking garage & two parking space outside. located few minutes from shopping, dinning, and parks.

  Hank Fatoorehchi Realty Executives Advance

  501 Leah Ln Unit 1A, Woodstock, IL 60098
• 

  

  /31

  $500,000

  Sold Dec 01, 2025

  8104 Mason Hill Rd, Woodstock, IL 60098

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Below List Price
  • $236/SF
  • 20 Days On Market

  Current Estimated Value $491,474

  Last Listing Agent Richard Toepper Keller Williams Success Realty

  8104 Mason Hill Rd, Woodstock, IL 60098
• 

  

  /27

  Est $836,026

  Not Listed For Sale

  1613 Bull Valley Dr, Woodstock, IL 60098

  • 5 Beds
  • 5 Baths
  • 4,670 Sq Ft
  • Built 2006

  1613 Bull Valley Dr, Woodstock, IL 60098

  Last Sold Summary

  • 77 Days On Market
• 

  

  /34

  $565,000

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

  10105 Il Route 120, Woodstock, IL 60098

  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

  Laura Lanz RE/MAX Plaza

  10105 Il Route 120, Woodstock, IL 60098
• 

  

  /20

  $295,000

  Sold Feb 09, 2026

  4244 Meadowridge Rd, Woodstock, IL 60098

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $166/SF
  • 46 Days On Market

  Last Listing Agent Bill Flemming HomeSmart Connect LLC

  4244 Meadowridge Rd, Woodstock, IL 60098
• 

  

  /8

  Est $240,758

  Not Listed For Sale

  3520 Castle Rd, Woodstock, IL 60098

  • 3 Beds
  • 1.5 Baths
  • 976 Sq Ft
  • Built 1952

  3520 Castle Rd, Woodstock, IL 60098

  Last Sold Summary

  • 2 Days On Market
• 

  

  /4

  $295,000

  • Land
  • 0 Sq Ft

  9999 E Calhoun St, Woodstock, IL 60098

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

  Brian Coleman Brian Coleman & Associates,Inc

  9999 E Calhoun St, Woodstock, IL 60098

Showing Results 201 - 240, Page 6 of 18