Illinois Homes for Sale with a Guest House

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  /61

  $1,700,000 Open Sat 12AM - 2PM

  • 6 Beds
  • 6 Baths
  • 3,800 Sq Ft

  2334 W Medill Ave, Chicago, IL 60647

  Prepare to be captivated by this rare 4-story home with a COACH house located on one of Bucktown's most coveted one-way streets and in Pulaski IB district. This Coach home increases your buying power by an est $500,000 with the rental income of $4K/month. This home is anchored by a custom floating staircase designed in Italy and eco-friendly HEATED cork flooring. The home's design seamlessly

  

  Jennifer Evans Piet

  @properties Christie's International Real Estate

  (872) 253-4482

  2334 W Medill Ave, Chicago, IL 60647
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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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  /62

  $635,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 4,145 Sq Ft

  724 Schwarz Rd, Edwardsville, IL 62025

  Gorgeous UPDATED ALL BRICK 4BR home nestled on private 1.16 acre lot in the heart of Edwardsville complete w/pool PLUS Guest house! You will love all the outdoor space for entertaining: circle drive, covered patio, private 18'x36' pool, outdoor shower & expansive pool deck. Guest/Pool House w/kitchen, bath, laundry, LR, wood ceiling & LVP flooring. Natural light floods Main house: LR w/gas FP &

  

  Janet Urbanek

  Coldwell Banker Brown Realtors

  (618) 627-5755

  724 Schwarz Rd, Edwardsville, IL 62025
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  /99

  $485,000

  • 5 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  1341 Schleeper Ln, Golden Eagle, IL 62036

  One-of-a-Kind Country Estate in the Rolling Hills of Calhoun County, Illinois. If you’ve been searching for breathtaking views, space to roam, and a property built with intention and quality — this is it.Nestled in the heart of Calhoun County, this former operating farm offers a rare combination of a custom-built primary home, a second residence, and an impressive lineup of functional

  

  Cyndi Borrowman

  Market Pro Realty, Inc

  (618) 787-1767

  1341 Schleeper Ln, Golden Eagle, IL 62036
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  /50

  $700,000

  • 4 Beds
  • 3.5 Baths
  • 2,820 Sq Ft

  14103 Westwood Trail, Woodstock, IL 60098

  Tastefully updated sprawling ranch set on a private and picturesque 2.5-acre homesite with a separate guest house-an exceptional and rarely available opportunity. From the moment you enter, you'll appreciate the thoughtful floor plan, crown molding, and quality craftsmanship throughout. The welcoming foyer opens to a formal living room with a focal-point fireplace and direct access to the formal

  

  Elizabeth Goodchild

  Realty of America

  (779) 244-6768

  14103 Westwood Trail, Woodstock, IL 60098
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  /3

  $67,500

  • Studio
  • 1,416 Sq Ft

  807 W Pleasant St, Freeport, IL 61032

  2-Unit Multifamily Property – Tenants Responsible for Utilities! An Excellent Investment Opportunity! This duplex presents a reliable source of rental income with significant potential for growth. Both units are equipped with central air conditioning, and tenants are responsible for all utility payments, ensuring a hassle-free investment experience. Unit 1: A spacious 3-bedroom, 1-bathroom unit

  

  Tracy Shuman

  Re/Max Professional Advantage

  (779) 223-5539

  807 W Pleasant St, Freeport, IL 61032
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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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  /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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  /57

  $555,000

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

  11373 W Us Highway 20, Galena, IL 61036

  Reduced - Make your offer today! Investors change of plans, affords an amazing opportunity for a New Owner of this Galena Historic "Ryan Mansion" - Landmarked and Potential for Small Inn or Bed & Breakfast hat's located on the corner of Hwy 20 & Oldenburg Lane in Galena. Home is under construction with many new improvements completed in the last 2 years. Improvement/Repair List included in

  

  Angela Stodden

  KELLER WILLIAMS REALTY SIGNATURE

  (779) 243-6715

  11373 W Us Highway 20, Galena, IL 61036
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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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  /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

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,616 Sq Ft

  202 Country Club Dr, McHenry, IL 60050

  Welcome to your sprawling riverfront estate on the Fox River! Situated on a premier .86-acre lot, this 4-bedroom, 3.1-bathroom home offers over 2,600 square feet of thoughtfully designed living space, with every detail carefully considered and recently updated. The heart of the home features a unique dual-sided gas starter/wood-burning fireplace that serves both the kitchen and the living room,

  Patricia Smarto Lakes Realty Group

  202 Country Club Dr, McHenry, IL 60050
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  /31

  $254,000 Open Sat 3:30PM - 5:30PM

  • 8 Beds
  • 3 Baths

  5756 S Princeton Ave, Chicago, IL 60621

  Attention Investors! Discover an incredible opportunity for investors and owner-occupants in this versatile multi-unit property. Featuring two spacious units plus a nonconforming basement AND a coach house unlocks a ton of income potential. Units 1 and 2 offer 3 bedrooms and 1 bathroom, ideal for owner-occupants, investors, or those exploring short-term rental opportunities. Both units feature

  Brittany Strale Redfin Corporation

  5756 S Princeton Ave, Chicago, IL 60621
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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 - Algonquin

  305 Oregon Ave, West Dundee, IL 60118
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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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  /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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  /32

  $92,000

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  134 E Washington St, Rushville, IL 62681

  134 E. Washington St. Rushville, IL This charming 3-bedroom, 1-bath home perfectly balances small-town convenience with a quiet residential feel. Located just half a block from the vibrant city square, you are steps away from City Hall, the Post Office, and an array of local shopping and dining. The Main Living Area Step onto the cute covered front porch and into a welcoming vestibule that opens

  Lacey Cunningham Legacy Land Co LLC

  134 E Washington St, Rushville, IL 62681
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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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  /82

  $359,000

  • 3 Beds
  • 2 Baths
  • 2,860 Sq Ft

  9313 W Parks School Rd, Princeville, IL 61559

  Welcome home to your private retreat nestled on 4.62 wooded acres, offering the perfect blend of nature, comfort, and versatility. Step inside to an open-concept great room featuring a vaulted ceiling, stunning floor-to-ceiling windows, and a gas log fireplace that creates a warm, welcoming focal point. Natural light pours in providing breathtaking views of the surrounding landscape. Enjoy

  Kim Ely RE/MAX Traders Unlimited

  

  9313 W Parks School Rd, Princeville, IL 61559
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  /36

  $650,000

  • 6 Beds
  • 3 Baths
  • 2,800 Sq Ft

  3306 W Le Moyne St, Chicago, IL 60651

  Darling brick farm house, originally built in 1888 before the first World Fair. This property is for EVERYONE- those who want new construction and those who love historic charm. The location, just a block west to Humboldt Park, IS on the brink of becoming THE MOST POPULAR spot in CHITOWN! Enjoy 197.26 acres of Humboldt Park with baseball fields, miles of running, ponds, field houses, and tamale

  Elizabeth Amidon Jameson Sotheby's Intl Realty

  3306 W Le Moyne St, Chicago, IL 60651
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  /48

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  7634 N 1st St, Altamont, IL 62411

  You Are Seeing Doubles on this Country property in Altamont IL! Check this out: there are 2 houses, 2 barns, and 2.33 acres, all for ONE price! Located in Altamont Schools! Enter this property to the remodeled 1910 Farmhouse, complete with 3 bedrooms and 2 baths. Featuring tin ceilings, hardwood and LVT flooring, tin and wood plank walls, a Master Suite with walk-in closet and its own bath, all

  Brian Henning Full Circle Realty

  7634 N 1st St, Altamont, IL 62411
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  /75

  $349,000

  • 3 Beds
  • 5 Baths
  • 2,554 Sq Ft

  535 E Main St, Du Quoin, IL 62832

  Welcome this spacious two-story home with 3 bedrooms and 5 bathrooms, with all bedrooms conveniently located on the upper level for added privacy. Step inside to find beautiful hardwood floors throughout and a functional layout designed for everyday living. The kitchen features a pantry/storage area and provides direct access to the outdoor deck-perfect for entertaining or enjoying your morning

  Robert Davenport RE/MAX REALTY CENTRAL

  535 E Main St, Du Quoin, IL 62832
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  /35

  $1,650,000

  • 9 Beds
  • 4 Baths

  1908 S Loomis St, Chicago, IL 60608

  A rare and exceptional opportunity to own a classic brick Chicago four-flat with an additional detached three-unit coach house. The main building features four units including a 3 bed/1 bath on the first floor, a 2 bed/1 bath on the second floor, plus two street-level units offering a 1 bed/1 bath and a 2 bed/1 bath. The rear coach house adds even more value with two 2 bed/1 bath units on the

  Cesar Juarez Redfin Corporation

  1908 S Loomis St, Chicago, IL 60608
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  /59

  $749,900

  • 4 Beds
  • 3.5 Baths
  • 2,329 Sq Ft

  526 Shiloh Rd, Cobden, IL 62920

  Where every day feels like a getaway, nestled on just under 46.73 acres in the heart of Southern Illinois along the Shawnee Hills Wine Trail, this stunning country retreat offers the perfect blend of privacy, craftsmanship, and natural beauty. Built in 2013 and inspired by renowned architect Ross Chapin, the main home features 3 bedrooms, 2.5 baths, and an open-concept design filled with natural

  Presley Barnett COLDWELL BANKER J D THOMPSON

  526 Shiloh Rd, Cobden, IL 62920
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  /40

  $3,950,000

  • 5 Beds
  • 6 Baths
  • 9,200 Sq Ft

  1352 N La Salle Dr, Chicago, IL 60610

  Best value! Stately, sophisticated, and truly one of a kind - this oversized 33 x 149 ft estate sits in the heart of prime Old Town, offering the scale and presence rarely found this close to both Old Town and the Gold Coast. Originally restored and thoughtfully reimagined in 2016, the home seamlessly blends historic architecture with modern livability. Most recently refreshed by Brianne Bishop

  Julie Harron Jameson Sotheby's Intl Realty

  1352 N La Salle Dr, Chicago, IL 60610
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  /50

  $495,000

  • 5 Beds
  • 3 Baths
  • 3,024 Sq Ft

  401 E Prairie St, Odell, IL 60460

  Absolutely Beautiful! This Fabulous-Southern Architecture style 5-Bedroom, 3-Bathroom Mansion-Estate situated on almost 3-Acres is incredible! The Two-Three Story Home which has over 4,000 sq. Ft. of living space, was a former Illinois State Senators Home and has a Coach house, mini-coach house and filled with impeccable Quality, millwork and Detail thru out! From the moment you drive-up, the

  James Skorupa Coldwell Banker Real Estate Group

  401 E Prairie St, Odell, IL 60460
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  /54

  $275,000

  • Studio
  • 2,086 Sq Ft

  515 N 6th St, Rochelle, IL 61068

  GREAT INVESTMENT OPPORTUNITY. 3 RENTED UNITS TOTAL. MAIN 2 STORY- UNIT 1 FEATURES LIVING ROOM, DINING ROOM, KITCHEN, FULL BATH, FFL, AND 2 BEDROOMS. CENTRAL AIR, STOVE, RANGE HOOD, REFRIGERATOR, WASHER & DRYER. UNIT 2 FEATURES LIVING ROOM, KITCHEN, FULL BATH AND 1 BR. WINDOW AC, STOVE, RANGE HOOD, & REFRIGERATOR. EXTERIOR ENTRANCE TO BASEMENT. UNIT 1 TENANT USES BASEMENT. THIS BUILDING IS ALLUM.

  Kimberly Cooley Berkshire Hathaway HomeServices Starck RE

  515 N 6th St, Rochelle, IL 61068
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  /44

  $409,873

  • 6 Beds
  • 3.5 Baths
  • 2,652 Sq Ft

  1708 N Center St, Crest Hill, IL 60403

  If you have a large or extended family and want to live close to one another, this rare opportunity offers two separate homes on one lot that you simply must see! The front home is a ranch with basement beautifully remodeled by the current owners in 2018/2019. Its truly eye-catching interior features vaulted ceilings with exposed beams, a modern kitchen with white cabinetry, granite countertops,

  Thomas Domasik RE/MAX 10 in the Park

  1708 N Center St, Crest Hill, IL 60403
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  /18

  $95,000

  • Studio
  • 1,484 Sq Ft

  801 N Winnebago St, Rockford, IL 61103

  Great investment opportunity in a prime Rockford location! This spacious duplex offers 1,484 sq ft per unit, first floor unit has 1 bedroom second floor unit has 2 bedrooms. Property needs some TLC but is packed with potential and sweat equity for the savvy investor. Perfect for someone looking to start or grow their portfolio - or live in one unit while renting out the other for added income.

  Fidel Batres Keller Williams Realty Signature

  801 N Winnebago St, Rockford, IL 61103
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  /97

  $1,350,000

  • 4 Beds
  • 6 Baths
  • 5,143 Sq Ft

  41W219 Forest Ln, Elburn, IL 60119

  Set at the end of a quiet street and surrounded by 6.81 acres of lush, wooded landscape, this extraordinary 5,000+ square foot soft contemporary residence is a true architectural statement-designed to bring the outdoors in and elevate everyday living. From the moment you arrive, the home's design and layout make a lasting impression. Soaring beamed ceilings and expansive walls of windows create

  Joyce Courtney The HomeCourt Real Estate

  41W219 Forest Ln, Elburn, IL 60119
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  /52

  $890,000

  • 4 Beds
  • 3 Baths
  • 2,969 Sq Ft

  12719 234th Ave, Trevor, WI 53179

  Stunning property on nearly 1/2 acre with 100 feet of footage on Cross Lake! This 4-BR, 3-bath home has been meticulously updated throughout. Incredible lake views with expansive windows throughout the great room, a large deck and upper balcony. Enjoy direct lake access with your private boat slip for boating, fishing, kayaking & swimming. Newer hot tub and large patio with firepit and outdoor

  Melissa Nelson Redfin Corporation

  12719 234th Ave, Trevor, WI 53179
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  /68

  $3,275,000

  • 6 Beds
  • 5.5 Baths
  • 7,700 Sq Ft

  2855 Sheridan Place, Evanston, IL 60201

  Step into a piece of history with this beautifully updated and expanded early 20th-century home, seamlessly blending timeless elegance with contemporary comforts. Nestled on a rare .70 acre lot, this northeast Evanston residence offers the perfect blend of classic luxury and modern charm. Built in 1911 for Swedish Ambassador Oscar Haugen, and designed by architect Augustus Nyden, this landmark

  Stephanie Poulakidas Compass

  2855 Sheridan Place, Evanston, IL 60201
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  /47

  $2,295,000

  • 6 Beds
  • 7 Baths
  • 10,000 Sq Ft

  1850 N Mulford Rd, Rockford, IL 61107

  A rare opportunity to own the historic Reuben Aldeen Estate - offered for the first time in 30 years. Set on 11.36 picturesque acres, this lovingly maintained property includes two homes and an additional 2 acre buildable lot, all sold together as one extraordinary offering. The primary residence, built in 1945, spans approximately 10,000 square feet of interior living space yet maintains an

  Kipp Blackburn RE/MAX Premier Luxury Collection

  1850 N Mulford Rd, Rockford, IL 61107
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  /39

  $575,000

  • 12 Beds
  • 8 Baths

  5930 S King Dr, Chicago, IL 60637

  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

  5930 S King Dr, Chicago, IL 60637
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  /4

  $200,000

  • Studio
  • 2,622 Sq Ft

  2234 11th Ave, Rockford, IL 61104

  Ready money maker. Separate utilities. Two car garage shared. Pictures representative of prior to tenant move in.

  KENNETH REDEKER Keller Williams Realty Signature

  2234 11th Ave, Rockford, IL 61104
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  /4

  $175,000

  • Studio
  • 2,268 Sq Ft

  1022 15th St, Rockford, IL 61104

  Opportunity Knocks with this solid all brick 2 unit complete with tenants! Each unit has a kitchen, living room, separate dining room, two bedrooms and one bath. Wood flooring throughout most of the unit living space. One unit had some updates 2 years ago. Tenants each have access to a garage stall and the basement. Tenants pay electric and gas bills. 48 Hour Show Notice. Property sold "As Is."

  Mary Maxted Keller Williams Realty Signature

  1022 15th St, Rockford, IL 61104
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  /36

  $635,000

  • 6 Beds
  • 4 Baths
  • 4,668 Sq Ft

  701 Viking Dr, Batavia, IL 60510

  Rare opportunity to own this unique Batavia property. It offers the perfect blend of comfortable living and income potential with two attached residences on a spacious corner lot.The main home is a well-maintained raised ranch featuring 4 bedrooms and 3 full bathrooms. The updated kitchen opens to a large eating area, creating an inviting space for everyday living with an adjacent 3-season room

  Heather Prowell Baird & Warner Fox Valley - Geneva

  701 Viking Dr, Batavia, IL 60510
• 

  

  /11

  $109,900

  • Studio
  • 1,874 Sq Ft

  302 E Prospect Terrace, Freeport, IL 61032

  Great investment opportunity! This well-maintained duplex features a 2 bed/1 bath unit on the first floor and a 1 bed/1 bath unit on the second floor. Perfect for investors or owner-occupants looking to live in one unit and rent the other. Recent updates include new siding and updated gutters (2022). Roof is in good condition. Don’t miss your chance to make this property yours today!

  Viridiana Duran Realty of America, LLC

  302 E Prospect Terrace, Freeport, IL 61032
• 

  

  /19

  $200,000

  • Studio
  • 2,560 Sq Ft

  404-406 E Prospect Terrace, Freeport, IL 61032

  Stop Renting. Start Owning! Unique homeownership opportunity designed for renters ready to make the move to owning. Two-story duplex featuring 2 bedrooms and 1 bathroom in each unit. The main floor unit offers a spacious living room and separate dining room with hardwood flooring, plus a kitchen with new vinyl plank flooring and main floor laundry hookups. The upper unit features a light-filled

  Olga Kampmeier Keller Williams Realty Signature

  404-406 E Prospect Terrace, Freeport, IL 61032
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  /90

  $2,545,000

  • 5 Beds
  • 7 Baths
  • 5,010 Sq Ft

  1308 N Wright St, Naperville, IL 60563

  Luxury without compromise-where elegant design, craftsmanship, and modern living converge. Experience elevated living in this remarkable estate, set on a beautifully landscaped .67-acre lot just minutes from vibrant Downtown Naperville. Built and designed by award-winning luxury builder Siena Custom Home Builders in collaboration with CVG Architects, this one-of-a-kind residence captures the

  Kim Preusch @properties Christies International Real Estate

  1308 N Wright St, Naperville, IL 60563

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