Illinois Homes for Sale with a Guest House

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  /57

  $575,000

  • 10 Beds
  • 10 Baths
  • 7,449 Sq Ft

  11373 W Us Highway 20, Galena, IL 61036

  Investors change of plans, affords an amazing opportunity for a New Owner of this Galena Historic "Ryan Mansion" - Landmarked and Licensed Small Inn located on the corner of Hwy 20 & Oldenburg Lane in Galena. Inn is under construction with many new improvements completed in the last 2 years. Improvement/Repair List included in Associated Docs. Seller is pricing to sell As-Is with existing

  

  Angela Stodden

  KELLER WILLIAMS REALTY SIGNATURE

  (779) 243-6715

  11373 W Us Highway 20, Galena, IL 61036
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  /56

  $799,900

  • 6 Beds
  • 10 Baths
  • 7,104 Sq Ft

  876 W State St, Jacksonville, IL 62650

  It's time to fall in love & step into a restored 1857 Italianate brick residence where historic craftsmanship and modern comfort meet in a way that feels both grand and livable. With 8,000+ sq ft, the home offers a flexible layout suited to everyday life, including space for multi-generational living, private guest quarters, and work-from-home offices or studio rooms. Multiple living zones create

  

  Lance Merrick

  Keller Williams Pinnacle

  (217) 646-7522

  876 W State St, Jacksonville, IL 62650
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  /15

  $164,500

  • 4 Beds
  • 2.5 Baths
  • 2,262 Sq Ft

  604 W Water St, Pinckneyville, IL 62274

  One of Pinckneyville's few remaining Victorian-era homes, this beautifully updated residence blends timeless character with modern convenience and exceptional versatility. Situated on a unique corner, fully fenced lot, the property includes a separate guest home/home-based business building, formerly a hair salon, offering endless possibilities for a home-based business, guest quarters, or

  

  Shannon Long

  Baird & Warner Fox Valley - Geneva

  (618) 740-6685

  604 W Water St, Pinckneyville, IL 62274
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  /71

  $205,000

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft

  526 Power Plant Rd, Marion, IL 62959

  UNIQUE OPPORTUNITY, MARION, CLOSE TO THE LAKE OF EGYPT. 3-acre wooded property includes a Pole Barn Home and 3 cabins, live in one, rent the others out, would make great short-term rentals. Want to live on the grid, this is your perfect opportunity. You have public water and aerobic septic system, large enough to hook all cabins up to it, currently only pole barn and Cabin 1 are hooked up. The

  

  Linda Cox

  C21 HOUSE OF REALTY, INC. L

  (618) 740-6416

  526 Power Plant Rd, Marion, IL 62959
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  /34

  $739,900

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  2N101 Glen Ellyn Rd, Glendale Heights, IL 60139

  Endless Potential Meets Modern Comfort in This Rare Opportunity! Positioned on nearly an acre of land with prime highway access, this updated 3-bedroom, 2-bath home offers a remarkable combination of residential charm and commercial promise. Nestled in a high-visibility, commercially active area, the property is zoned for both residential and agricultural use-with promising possibilities for

  

  Rafay Qamar

  Real Broker LLC

  (331) 291-8871

  2N101 Glen Ellyn Rd, Glendale Heights, IL 60139
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  /53

  $495,000

  • 15 Beds
  • 13.5 Baths
  • 9,851 Sq Ft

  202 W Poplar St, Harrisburg, IL 62946

  Seller is open to sell, rent or lease. This property was a hotel and can be one again. It could also be used for a variety of other applications from group housing, to offices, to luxury living. You could even build your own family compound for multi family estate. Calling all investors or luxury buyers! This unique property has tons of space with twin mansions & a carriage house all on a single

  

  Al Lenkaitis

  Four Ways Realty

  (618) 568-4585

  202 W Poplar St, Harrisburg, IL 62946
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  /4

  $40,000

  • Land
  • 0.68 Acre
  • $58,824 per Acre

  218 Madison St, Benton, IL 62812

  Four equal 51' x 145' lots in town that total approximately 0.68 acres. This could be a great place to build your new home and have a nice sized yard, right in town! Located not just a couple of blocks from the Benton town square! All people viewing the property must sign a "Hold Harmless" document due to there being a possible rehab/project home currently on one of the lots. This home could be

  

  Brittany Neal

  VIP Realty

  (618) 681-4447

  218 Madison St, Benton, IL 62812
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  /39

  $600,000

  • 12 Beds
  • 8 Baths

  Unlisted Address

  Prime Washington Park development opportunity offering scale, flexibility, and park-front exposure. Zoned RM-5, this property features an approximately 8,000 sq ft main building plus a coach house with three on-site garage spaces, presenting potential for 6-9 residential units (buyer to verify). The main building is fully gutted and ready for redevelopment, with bright garden-level units and

  

  Rafay Qamar

  Real Broker LLC

  (872) 239-3336

  Unlisted Address
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  /76

  $950,000

  • 5 Beds
  • 5.5 Baths
  • 10,435 Sq Ft

  2716 Spring Creek Rd, Rockford, IL 61107

  Executive Living at its finest! This estate offers so very much space, attention to fine detail and quality finishes that you'll find nothing to be desired! 5 bedrooms including 3 owners-suites, 5.5 bathrooms. An entertainer's dream home, this one is destined to impress! Greet your guests at the butlers station, welcome them into the 20' cathedral-ceilinged kitchen and let them relax on the

  Kevin Horstman Berkshire Hathaway HomeServices Crosby Starck RE

  2716 Spring Creek Rd, Rockford, IL 61107
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  /48

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  9219 E Best Ct, Effingham, IL 62401

  Calling all Lake Sara buyers! This property is located on Lake Sara in Effingham, IL. Lake Sara is a very sought out man made lake that was created in 1957. Spanning of private coves, restaurants, and beautiful homes; just like this property! Built in 2021, this contemporary style home offers 4 bedrooms, 3-1/2 baths, over 2,500 above grade square footage, and finishes that will take your breath

  Alex Steppe RE/MAX Key Advantage

  9219 E Best Ct, Effingham, IL 62401
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  /58

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 5,234 Sq Ft

  204 Country Commons Rd, Trout Valley, IL 60013

  Historic Masterpiece in the Heart of Trout Valley, once owned by John Hertz, is a one-of-a-kind property where heritage meets modern luxury. Nestled in the storied community of Trout Valley, this extraordinary estate blends timeless charm with purposeful design-perfect for living and working from home. Originally built in the 1890s, this mixed-use Residential/Commercial B1 zoned property where

  Michelle Mackey Baird & Warner

  204 Country Commons Rd, Trout Valley, IL 60013
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  /36

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft

  2034 Gittleson Rd, Rochelle, IL 61068

  Ever dream of a country living close to everything you need? This is it! The Classic American Foursquare home boasts a thoughtfully designed floor plan radiating with natural light, creating an inviting ambiance throughout. Secluded Farmette, nestled on 2.24 acres of tranquil beauty with tiny home for added space or pool house. An in-ground pool and versatile barn outbuildings for various uses.

  James Foley Foley Properties Inc

  2034 Gittleson Rd, Rochelle, IL 61068
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  /40

  $899,900

  • 13 Beds
  • 13 Baths

  305 Oregon Ave, West Dundee, IL 60118

  Step right into 1907 with this iconic West Dundee landmark - The Mansion at 305 Oregon Ave - a Tudor Revival masterpiece built for Illinois Iron & Bolt president John F. Fierke and still wrapped in its original ornamental iron fence handcrafted by the very company that built Dundee's industrial legacy. This historic estate has lived many lives: elegant private residence, beloved bed & breakfast,

  Hilda Jones Baird & Warner Real Estate - A

  305 Oregon Ave, West Dundee, IL 60118
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  /82

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft

  295 Panthers Den Rd, Makanda, IL 62958

  Welcome to Rocky Comfort Cabins, a fully operational short term rental business with a strong brand, loyal repeat guests, and proven income since 2013. Located in Makanda, IL, this turnkey property offers peaceful seclusion with easy access to area amenities. Three unique cabins include one French colonial style design and two “hobbit-style” builds, each with private hot tubs, fire pits,

  Jesse Klingler Trophy Properties & Auction

  295 Panthers Den Rd, Makanda, IL 62958
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  /55

  $3,445,000

  • 6 Beds
  • 5.5 Baths
  • 12,175 Sq Ft

  8508 Illinois 120, Woodstock, IL 60098

  Extraordinary 12,000+ SQ FT Country Estate, including Guest House, on 34+ acres (combination of woods, wetlands & open area)....NONE OTHER LIKE IT (view the 2.5 minute virtual tour for a great overview)....Geared toward family entertainment....Magnificent water views of the private pond and neighboring water features....Full renovation (to the "studs") of both the Main house & Guest house

  Chris Bartnick Berkshire Hathaway HomeServices Starck Real Estate

  8508 Illinois 120, Woodstock, IL 60098
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  /61

  $6,700,000

  • 6 Beds
  • 8 Baths
  • 8,947 Sq Ft

  Unlisted Address

  Featured as one of the Top Spotlight Homes on the Hinsdale Center of the Arts 2010 Oak Brook Home Tour: this one is unlike any you have seen. Although secluded behind the gates of an acre lot, people recognize this home with its stone exterior and abundance of windows as an architectural masterpiece on this iconic Oak Brook corner of York and Canterberry, which welcomes local cyclists to rest on

  Diana Ivas Berkshire Hathaway HomeServices Chicago

  Unlisted Address
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  /107

  $2,295,000

  • 6 Beds
  • 4.5 Baths
  • 3,586 Sq Ft

  2150 W Monroe St, Chicago, IL 60612

  Here's your chance to own this fully renovated-1885 Victorian/Edwardian Style Mini-Mansion-with a separate coach house that includes a 3 car garage with separate apartment above. This full-gut renovation was completed in 2024, as seen on one of HGTV's renovation programs, as main house boasts 6 bedrooms and 3.5 baths, multiple fireplaces, mahogany and red oak floors, custom designer lighting and

  Mike Santore Keller Williams Thrive

  2150 W Monroe St, Chicago, IL 60612
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  /39

  $114,900

  • Studio
  • 2,205 Sq Ft

  408 N West Ave, Freeport, IL 61032

  Looking for an investment property, look no further. This up down duplex with each unit featuring 2 bedrooms and 1 bath with separate utilities. The basement has amply storage and washer and dryer hookup for each unit. In the rear there is a garage with one area for parking and the rest for storage so the tenant can keep all there outdoor maintenance items in. Make this one make money for you

  Ashley Heilman Welcome Home NW Illinois, Inc.

  408 N West Ave, Freeport, IL 61032
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  /71

  $1,899,900

  • 5 Beds
  • 5 Baths
  • 6,986 Sq Ft

  11 Moate Ln, Barrington, IL 60010

  Experience Refined Country Living In This Extraordinary Luxury Equestrian Estate On 5 Lush Acres. Step Inside And Discover This One Of A Kind Estate With Over 6,000 Sqft Of Living Space With Soaring Ceilings, Expansive Living Areas And High-End Finishes Throughout. Gourmet Eat-In Kitchen With Marble Counters, Large Island, Thermador/Subzero Appliances, And Ample Counter/Cabinet Space Makes This

  Reid Anderson Real Broker, LLC

  11 Moate Ln, Barrington, IL 60010
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  /14

  $667,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft

  7842 Landon Ln, Roscoe, IL 61073

  True 5 bedroom 2 story, features: Large main floor bedroom /w private bathroom, 4 more very spacious bedrooms upstairs, Open floor plan featuring kitchen with big island 7' 6" long, walk-in pantry and stainless appliances. Other features: 2 stairways to upstairs, 3 1/2 car finished garage, main floor laundry, popular "cubbies", open 2 story tall entry foyer, beautiful 18 x 14 covered deck,

  Douglas Page Re/Max Property Source

  7842 Landon Ln, Roscoe, IL 61073
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  /49

  $349,900

  • 2 Beds
  • 4 Baths
  • 1,510 Sq Ft

  445 S Ellis St, Bensenville, IL 60106

  One-of-a-kind property with its own separate in-law suite nestled just minutes from O'Hare International Airport and less than half a mile from major thoroughfares like Route 83, this home offers quick access to downtown Chicago, nearby suburbs, and everything in between - all while tucked away in a quiet residential setting. The main home features a comfortable 1 bedroom and 2 full bathrooms,

  Jacob Pikowski Better Homes & Gardens Real Estate

  445 S Ellis St, Bensenville, IL 60106
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  /32

  $449,500

  • 3 Beds
  • 2 Baths
  • 1,818 Sq Ft

  43 Lake Shore Dr, Pana, IL 62557

  VIEW! VIEW! VIEW! Welcome to your year-round oasis with 2 homes on Pana Lake in Oakland Ridge subdivision. 3 bedroom, 2 bath ranch style home with a walk out basement and 2.5 car attached garage. Enjoy the beautiful views on both decks. Also has a detached garage with a 3 bedroom, 2.5 bath apartment ideal for multi-generational living, guests, or mother-in-law quarters!

  Carol Spracklen Carol & Company

  43 Lake Shore Dr, Pana, IL 62557
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  /86

  $1,800,000

  • Land
  • 126 Acres
  • $14,286 per Acre

  520 Deerfield Rd, Raccoon Township, IL 62893

  Country Paradise on 126 Acres - Perfect for Equestrian, Livestock, and Outdoor Enthusiasts Discover your dream country retreat on this expansive 126-acre property, ideally suited for livestock, hunting, and outdoor living. This sanctuary offers a harmonious blend of lush timber and open pasture, with extensive fencing perfect for horses and cattle. Artesuan spring that runs year round providing

  JAMES SWARTZLANDER MIDWEST FARM & LAND

  520 Deerfield Rd, Raccoon Township, IL 62893
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  /50

  $6,250,000

  • 5 Beds
  • 9 Baths
  • 7,280 Sq Ft

  788 E Woodland Rd, Lake Forest, IL 60045

  A Quintessential Lake Forest Manor with Storied Legacy and Timeless Elegance. Perched on 2.5 acres along Lake Road, this iconic Lake Forest estate offers a rare blend of architectural pedigree, historical significance, and modern refinement. Originally designed in 1907 by renowned architect Howard Van Doren Shaw for Helen Poole Thompson, the home stands as a testament to early 20th-century

  Marina Carney Compass

  788 E Woodland Rd, Lake Forest, IL 60045
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  /33

  $350,000

  • 4 Beds
  • 3 Baths
  • 1,662 Sq Ft

  1046 State 32 Hwy, Sullivan, IL 61951

  Fully Renovated Ranch Near Lake Shelbyville!Located just outside of town and less than a mile from Lake Shelbyville and Sullivan Marina, this beautifully updated 3-bedroom, 2-bath ranch includes an additional 1-bedroom, 1-bath guest house. It offers the perfect blend of modern comfort and peaceful country living. The main home features a completely renovated interior with an open-concept

  Jennifer Underwood THATS A WRAP REALTY

  1046 State 32 Hwy, Sullivan, IL 61951
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  /35

  $207,500

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  793 County Road 635 E, Wayne City, IL 62895

  Rural Property on 2 Acres with Versatile Outbuilding Enjoy peaceful country living with this well-maintained 4-bedroom home situated on 2 acres, just minutes from small-town amenities. The home features a spacious living room with hardwood flooring, a kitchen equipped with stainless appliances, and an adjoining dining area perfect for gatherings. The master bedroom offers a private bathroom

  Lisa McKinney C21 All Pro Real Estate

  793 County Road 635 E, Wayne City, IL 62895
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  /6

  $12,000

  • Land
  • 0 Acre

  1011 Newton Ave, Johnston City, IL 62951

  50X151 lot size right in town of Johnson City. There is a inhabitable home on the property. Has electric and water on property, could make a great building sight!

  Allison Gerner MCCOLLUM REAL ESTATE

  1011 Newton Ave, Johnston City, IL 62951
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  /46

  $2,200,000 Open Sat 10:30AM - 12:30PM

  • 6 Beds
  • 4.5 Baths
  • 4,544 Sq Ft

  726 Lincoln St, Evanston, IL 60201

  Perfectly positioned on a premier tree-lined street in sought-after Northeast Evanston, just steps from Evanston's stunning lakefront beaches, Central Street shops, downtown Evanston, public transportation, and Northwestern University, This impeccable home offers timeless elegance, modern luxury, and an extraordinary private coach house. This 6 bedroom, 4.1-bath home with two-car garage showcases

  Alice Berger @properties Christie's International Real Estate

  726 Lincoln St, Evanston, IL 60201
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  /33

  $392,000

  • Studio
  • 3,544 Sq Ft

  3786 Sage Dr, Rockford, IL 61114

  Ranch-style duplex! Each unit offers 2 bedrooms, 2 bathrooms, a 2-car garage, and a partially finished basement with laundry, full bath, and outside egress. Units have separate utilities and are both rented, providing strong income potential or the option to live in one unit and rent the other. Conveniently located near Riverside Boulevard, shopping, dining, Costco, and I-90 access.

  Aimee Leon Gambino Realtors

  3786 Sage Dr, Rockford, IL 61114
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  /28

  $240,000 Pre-Foreclosure

  • 8 Beds
  • 4 Baths

  12402 S Green St, Calumet Park, IL 60827

  A unique investment opportunity featuring a 3-building package with 4 total units: a 2-flat with a partially finished basement; a single-family bungalow (includes the house on the corner with the address of 12400 S Green), and a coach house in the rear. Each unit includes 2 bedrooms and 1 bath, currently rented below market value, offering plenty of potential for increased income. SOLD AS-IS!

  Leah Marable Baird & Warner

  12402 S Green St, Calumet Park, IL 60827
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  /24

  $229,000

  • 3 Beds
  • 1.5 Baths
  • 1,341 Sq Ft

  1535 & 1535 1/2 S 5th Ave, Kankakee, IL 60901

  Great opportunity to own a spacious and renovated Main Home AND updated secondary home out back! All of this on an almost half acre lot in sought-after, South-Westside neighborhood within walking distance to parks and the Kankakee river. Main Home features 3 bedrooms and 1.5 bathrooms and has had lots of updates: NEW ROOF (2025), new windows, new flooring, updated electrical, updated kitchen, new

  Kelly Winterroth McColly Bennett Real Estate

  1535 & 1535 1/2 S 5th Ave, Kankakee, IL 60901
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  /19

  $45,000

  • Land
  • 1.17 Acres
  • $38,462 per Acre

  798 Airport Rd, Metropolis, IL 62960

  Approx. 1.17-acre lot with 4 trailers on the property that are not currently livable and will need a lot of work. Property has hookups for each individual trailer that includes 4 separate meters for electricity, county water on the property, and a septic system that runs into a lagoon. Investment opportunity in a great location.

  Cole Vickers Farmer & Co. Real Estate

  798 Airport Rd, Metropolis, IL 62960
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  /67

  $475,000

  • Studio
  • 4,180 Sq Ft

  522 S State St, Belvidere, IL 61008

  Turnkey mixed-use investment in the heart of Downtown Belvidere. This property offers immediate cash flow with an established main-level bar, featuring a full kitchen, 5 slot machines, and 3 pool tables. The second level houses five fully equipped residential lofts (stove/fridge/microwave included), all occupied by long-term tenants. Well-maintained with Central A/C throughout. Situated near the

  Fidel Batres Keller Williams Realty Signature

  522 S State St, Belvidere, IL 61008
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  /73

  $3,495,000

  • 4 Beds
  • 6 Baths
  • 4,225 Sq Ft

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
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  /40

  $215,000

  • 4 Beds
  • 3 Baths
  • 1,734 Sq Ft

  420 N High St, Galena, IL 61036

  High on history, high on views, high on charm! Step back in time with all the modern comforts in this newly renovated 1800s miner’s cottage. Where historic charm meets flexible living space and serene privacy, all just steps from downtown Galena. Set on three wooded city lots, this remarkable property offers the perfect blend of privacy and convenience, with daily deer sightings and a tranquil,

  Elizabeth Robinson Epique Realty

  420 N High St, Galena, IL 61036
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  /61

  $1,995,900

  • 4 Beds
  • 4.5 Baths
  • 14,900 Sq Ft

  2003 W Hanover Rd, Hanover, IL 61041

  Being offered for the first time on it's own 8.6 acre parcel, this is a generational opportunity to own one of the most iconic properties in the greater Galena area-The Rocky Waters Estate Vineyard and Winery. This nearly 15,000 square foot structure has served as the focal point of Rocky Waters operation since it's opening and has served as the wine making facility, the tasting room, the office,

  BRANDON BEYER JIM SULLIVAN REALTY

  2003 W Hanover Rd, Hanover, IL 61041
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  /46

  $468,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,836 Sq Ft

  COVENTRY Plan at Ivanhoe, Manhattan, IL 60442

  Introducing the Coventry floor plan featured at the Ivanhoe community in Manhattan, IL. This two-story, open concept home provides modern functionality with 4 large bedrooms, 2.5 baths, a bonus loft space for an added second floor living area with the option to include a guest room and full bath on the main level. The Coventry plan features a staircase situated away from the foyer for convenience

  D.R. Horton Builder

  15011 W Yorkshire St Unit 36206034, Manhattan, IL 60442
• 

  

  /75

  $685,000

  • 10 Beds
  • 8.5 Baths
  • 5,638 Sq Ft

  116 W Prospect Ave, Ottawa, IL 61350

  Welcome to the Cora J. Pope Home, one of Ottawa's most recognizable historic landmarks and a rare opportunity for anyone seeking a luxury Airbnb, boutique inn, or bed-and-breakfast property. Built in 1902 by Milton and Cora Pickens Pope, this Victorian masterpiece has been lovingly restored to its original grandeur while thoughtfully updated for modern comfort. Perched on a scenic bluff

  George Shanley Coldwell Banker Real Estate Group

  116 W Prospect Ave, Ottawa, IL 61350
• 

  

  /99

  $1,500,000

  • 9 Beds
  • 9 Baths
  • 15,000 Sq Ft

  409 N State St, Franklin Grove, IL 61031

  Welcome to Lincoln Way Stay, this property is a completely private, all-inclusive accommodation designed to make you feel transported to a world of luxury. Following eight and half fabulous years of welcoming countless guests, brides and grooms, and gatherings of all shapes and sizes, the property is presently utilized as a short-term guest lodging, but could also be perfect as private residences

  Linda Feinstein Compass

  409 N State St, Franklin Grove, IL 61031
• 

  

  /92

  $8,495,000

  • 6 Beds
  • 9 Baths
  • 12,000 Sq Ft

  5021 Minkler Rd, Yorkville, IL 60560

  Welcome to the Minkler Estate - a property unlike any other in Chicagoland. Surrounded by beautiful wildflowers, dense woods, and secluded prairie, this extraordinary 36-acre countryside haven offers the perfect blend of privacy, sophistication, and natural beauty. At the heart of the estate lies a stately 10,000+ sq ft English manor, meticulously renovated from the ground up to combine modern

  Michael Lafido LPT Realty

  5021 Minkler Rd, Yorkville, IL 60560

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