Illinois Homes for Sale with a Guest House

• 

  

  

  /42

  $268,000

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft

  750 45th St, New Boston, IL 61272

  I don't just sit by the river-I look out over it. Perched above the Mississippi with approximately 100 feet of beachfront, I give you the riverfront lifestyle you've been dreaming about, with beautiful elevated views and being located outside the mapped flood zone. Step inside and you'll understand why I feel more like a getaway than simply a house. Warm wood ceilings bring that cozy cabin

  Jen Miller RE/MAX Concepts Bettendorf

  750 45th St, New Boston, IL 61272
• 

  

  

  /21

  $299,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,215 Sq Ft

  3944 183rd St, Homewood, IL 60430

  Unique property in Homewood offering exceptional flexibility and charm. The main house features one bedroom, a newly remodeled bathroom, cherry cabinetry, granite countertops, hardwood flooring on the main level, and convenient in-unit laundry. The second-floor loft has new wall-to-wall carpeting and offers versatile space for an office suite, recreation area, guest space, or fun sleeping

  Gina Montalto Baird & Warner

  3944 183rd St, Homewood, IL 60430
• 

  

  

  /50

  $774,900

  $14K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 3,500 Sq Ft

  2S720 Nelson Lake Rd, Batavia, IL 60510

  Escape the ordinary and step into your own private retreat with 5 acres of country charm. Entering you will pass 20 garden plots, 18 fruit trees, trellises of grape vines and your own wild raspberry patch. The green garden shed has a wood burning stove and is partially drywalled just waiting to become a darling she shed. This area is highly landscaped with over 20 varieties of perennials. Stroll

  Jonathan Minerick Homecoin.com

  2S720 Nelson Lake Rd, Batavia, IL 60510
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  /102

  $1,360,000

  $15K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,174 Sq Ft

  112 Brinker Rd, Barrington, IL 60010

  Wonderful estate on over 5 acres private wooded grounds with gates and paved driveway. Great home with updated kitchen and baths. Separate dining room. Elegant design throughout. Cathedral ceiling in living room. Hardwood floor. Recessed lighting. Built-ins. Fireplaces. Master bath features steam and rainfall shower, soaking tub, double sink. Great loft. Skylights. 2 balconies. 2nd floor laundry

  Andrew Shevelev American Real Estate Services

  112 Brinker Rd, Barrington, IL 60010
• 

  

  

  /4

  $70,000

  Pending

  • Studio
  • 2,188 Sq Ft

  1650 S Oak Ave, Freeport, IL 61032

  Sold Before Release. Fantastic investment opportunity! This spacious duplex offers a total of 2,188 square feet of living space, with each unit featuring 2 bedrooms, 1 full bathroom, and convenient in-unit laundry. Both kitchens provide abundant cabinetry and generous workspace, while beautiful woodwork, some hardwood floors, and plentiful storage add to the property's charm and functionality.

  Milena Cojkic Keller Williams Realty Signature

  1650 S Oak Ave, Freeport, IL 61032
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  /41

  $159,900

  • Studio
  • 2,234 Sq Ft

  203 Ogilby Rd, Rockford, IL 61102

  Investor Alert! Turnkey Duplex Ready to Cash Flow! Add this spacious duplex to your portfolio and start putting it to work! Both units offer 2 bedrooms and 1 bath with generous living space and a layout tenants will love. Even better, many of the major improvements have already been taken care of, including new windows, new porches, new siding, newer roof, two new furnaces, two updated electrical

  Kristina Campbell Key Realty, Inc

  203 Ogilby Rd, Rockford, IL 61102
• 

  

  /34

  $449,500

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

  43 Lake Shore Dr, Pana, IL 62557

  VIEW! VIEW! VIEW! Beautiful lakefront property! 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

  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
• 

  

  /3

  $325,000

  Pending

  • Studio
  • 3,448 Sq Ft

  7514 N 2nd St, Machesney Park, IL 61115

  **SBR**

  Jodi Stromberg Berkshire Hathaway HomeServices Crosby Starck RE

  7514 N 2nd St, Machesney Park, IL 61115
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  /48

  $600,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,430 Sq Ft

  1687 Barberry Cir, Freeport, IL 61032

  Over 5,400 square feet of beautifully updated living space on a private 1.5+ acre wooded lot offering luxury, space, and value well below replacement cost. Enjoy high-end living in a sought after area surrounded by quality-built homes, with room to entertain, relax, and take in the peaceful natural setting. From the moment you enter, you’ll notice the impressive open staircase, formal dining

  Aubra Palermo RE/MAX Unites

  1687 Barberry Cir, Freeport, IL 61032
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  /116

  $1,200,000

  • 2 Beds
  • 3 Baths
  • 1,553 Sq Ft

  23709 66th Ave N, Port Byron, IL 61275

  Rare opportunity to own an exceptional 15-acre farmstead offering endless possibilities for horse enthusiasts, car collectors, hobby farmers, or anyone seeking the ultimate country lifestyle. Comprised of three parcels, the property features two homes, four outbuildings, farm pond views, hayfield, extensive parking, and hard-surface access throughout. The custom ranch home, built in 1995 by

  Marty Eilers BUY SELL BUILD QC - Real Broker, LLC

  23709 66th Ave N, Port Byron, IL 61275
• 

  

  /48

  $719,999

  $49K PRICE DROP Pending

  • 5 Beds
  • 4 Baths
  • 4,800 Sq Ft

  9375 E County Road 550n, Mattoon, IL 61938

  Experience the perfect blend of modern sophistication and thoughtful, practical living. Nestled on 18.46 private acres in Lafayette Township, perfectly positioned between Charleston and Mattoon, this one-of-a-kind estate offers a rare combination of custom craftsmanship, full ADA accessibility, and flexible living options. The Main Residence was custom-built in 2009 by McQueen Lumber of Oakland

  John Inyart TCI Realty, LLC

  9375 E County Road 550n, Mattoon, IL 61938
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  /38

  $315,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,055 Sq Ft

  16904 E 3130 North Rd, Rossville, IL 60963

  This unique property encompasses 8.5 acres of land that runs along the North Fork/Middle Branch river, featuring a main house with four bedrooms, two full bathrooms, a living room and family room all of which offer picturesque views of trees and wildlife. The primary bathroom has undergone recent renovations. Central air has recently been installed. The roof is newer as well. The remainder of the

  Shannon LaBounty RE/MAX ULTIMATE

  16904 E 3130 North Rd, Rossville, IL 60963
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  /46

  $138,500

  $11K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,080 Sq Ft

  700 Walnut St, Germantown, IL 62245

  Charming and affordable opportunity in the heart of Germantown! This spacious home offers flexible living arrangements. The property includes a finished former garage area with a full kitchen and bathroom, providing additional living space and flexibility for a variety of uses. Perfect for multi-generational living, an in-law suite, a teenager seeking extra privacy.The main home features

  Cassia Ohashi Worth Clark Realty

  700 Walnut St, Germantown, IL 62245
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  /106

  $2,250,000

  • 7 Beds
  • 11 Baths
  • 10,039 Sq Ft

  Unlisted Address

  A RARE OPPORTUNITY TO OWN A 10-ACRE GATED PRIVATE ESTATE OF BREATHTAKING BEAUTY - AN EXCLUSIVE BOTANICAL RETREAT OFFERING A PRESTIGIOUS LIFESTYLE WITH THE EASE OF MAIN FLOOR LIVING. This extraordinary, fully fenced compound offers a seamless blend of luxury, creativity, artistry, and lifestyle. Featuring a large multi-level primary residence and a two-story guesthouse, with a combined total of 5

  Kim Alden Compass

  Unlisted Address
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  /62

  $1,175,000

  • 4 Beds
  • 4 Baths
  • 3,816 Sq Ft

  2287 W Hanover Rd, Hanover, IL 61041

  Take note of one of Jo Daviess County’s premier properties. This stunning rustic contemporary home showcases luxurious finishes, breathtaking panoramic southern views, and unmatched privacy on 43.26± picturesque acres. The property features your own nearly 2-acre stocked pond, rolling countryside, and a rare combination of open land, timber, and income-producing farmland. Tucked away at the end

  Garrett Hillary KELLER WILLIAMS REALTY SIGNATURE

  2287 W Hanover Rd, Hanover, IL 61041
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  /33

  $365,000

  $27K PRICE DROP Pending

  • 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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  /72

  $325,000

  • 7 Beds
  • 5 Baths
  • 6,366 Sq Ft

  Unlisted Address

  Truly One of a Kind! This stunning Victorian home offers a rare combination of charm, versatility, and space. Spanning three levels with a separate coach house, the property can be used as a spacious single-family residence with related living or as a four-unit rental investment. Each level features its own kitchen, living room, bathroom, and bedrooms, providing private, fully functional living

  Dondi Maricle Berkshire Hathaway HomeServices Speckman Realty

  Unlisted Address
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  /47

  $460,000

  $5K PRICE DROP Pending

  • Studio
  • 3,690 Sq Ft

  820 Cottage Grove Ave, Rockford, IL 61103

  Well-maintained four-unit property offering strong rental potential. Each apartment features 2 bedrooms, 1 full bath, a comfortable living room, and an eat-in kitchen with stove and refrigerator included. Two units also offer in-unit laundry hookups for added convenience. Tenants enjoy separate utilities and air conditioning. A detached four-car garage provides added parking and storage

  Aimee Leon Gambino Realtors

  820 Cottage Grove Ave, Rockford, IL 61103
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  /56

  $559,000

  Pending

  • 8 Beds
  • 4 Baths

  433 E 91st Place, Chicago, IL 60619

  Well-maintained 4-unit corner investment property located in the prime Chatham area, offering strong rental income and excellent investment potential. The building is fully tenant-occupied with security deposits and month to month leases, including several long-term tenants. Tenants pay all utilities, including heat, electricity, and cooking gas. Each apartment features a spacious layout, high

  Diana Varva Century 21 Circle

  433 E 91st Place, Chicago, IL 60619
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  /63

  $375,000

  • 4 Beds
  • 3.5 Baths
  • 2,376 Sq Ft

  601 Fair Park Dr, Oregon, IL 61061

  Just Steps from Fairground Park — Spacious, Flexible, and Full of Possibilities! Welcome to this beautiful 2,976-square-foot home featuring 4 bedrooms, 3½ bathrooms, and a 3-car garage, with plenty of room for family, guests, and entertaining. The inviting main level offers a comfortable family living room, spacious kitchen and eating area, plus a separate dining room—creating an ideal layout for

  Lora Gilbert DICKERSON & NIEMAN

  601 Fair Park Dr, Oregon, IL 61061
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  /76

  $750,000

  • 5 Beds
  • 3 Baths
  • 2,500 Sq Ft

  1961 Miner St, Des Plaines, IL 60016

  Wonderfully set up in a very large lot in a very desirable location. It's the developers and Investors dream Land. Front Home offers 4 BR, 2 BTH, with a Fire place. Good size Dining are and a kitchen with Breakfast area and a large commercial grade 4 car garage and on the top of the garage, there is one Bedroom, huge 25x22 living and dining with a Fire place, and a nice kitchen with custom

  Krupavaram Pudi Dome Realty, Inc

  1961 Miner St, Des Plaines, IL 60016
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  /62

  $1,495,000

  $80K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,819 Sq Ft

  3464 Old Mill Rd, Highland Park, IL 60035

  Expanded and renovated in 2008, this two-story prairie-style executive home offers over 9,000 square feet of finished living area across three levels, all easily accessible by a centrally located elevator or stairs, and is situated on over an acre of wooded property along a quiet, private road in Highland Park. The home offers exceptional flexibility with spaces ideal for a variety of lifestyles,

  Kelly Ipjian Exit Strategy Realty

  3464 Old Mill Rd, Highland Park, IL 60035
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  /55

  $494,900

  • 8 Beds
  • 4 Baths
  • 2,075 Sq Ft

  111 E Main St, Grafton, IL 62037

  Discover an exceptional turnkey investment opportunity in the heart of historic Grafton. Currently operating as a successful short-term guest house with four separate guest units. Character, comfort, outdoor entertainment and water views. With multiple income producing accommodations, this property is ideally suited to live in one and rent the others! The rear entry 2 car garage with manual

  Wendi Mielke Market Pro Realty, Inc

  111 E Main St, Grafton, IL 62037
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  /87

  $950,000

  $200K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,635 Sq Ft

  4601 Kimberly Lake Ln, Swansea, IL 62226

  An extraordinary private country estate where luxury, recreation, and nature exist in perfect harmony. Nestled on approximately 5.2 acres along the banks of Kimberly Lake, this one-of-a-kind estate was completely renovated in 2020 and offers an exceptional lifestyle just minutes from shopping, dining, hospitals, and interstate access. The beautifully remodeled main residence offers over 3,600 sq

  Summer Penet Nettwork Global

  4601 Kimberly Lake Ln, Swansea, IL 62226
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  /61

  $1,750,000

  $250K PRICE DROP

  • 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
• 

  

  /87

  $399,900

  Pending

  • 5 Beds
  • 2 Baths
  • 2,963 Sq Ft

  30319 Brookville Rd, Lanark, IL 61046

  Located in eastern Carroll County, this unique rural property offers a rare opportunity to own two homes on one property, creating a variety of possibilities for extended family living, guest accommodations, rental potential, or a private country retreat. Surrounded by the rolling hills and picturesque countryside that make this area of northwestern Illinois so desirable, the property combines

  Todd Henry Whitetail Properties Real Estate LLC

  30319 Brookville Rd, Lanark, IL 61046
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  /68

  $729,000

  $40K PRICE DROP Pending

  • 5 Beds
  • 5 Baths
  • 4,532 Sq Ft

  11620 E Charles Rd, Mount Carroll, IL 61053

  Discover a truly one-of-a-kind custom modern country estate set on 20 scenic acres in picturesque Jo Daviess County. Originally commissioned in the early 1970s as a private architect-designed residence, the home was carefully integrated into the surrounding wooded landscape and remains a rare example of sophisticated Midwest modern residential design. This expansive ranch residence offers over

  ERIC ANDERSON CHOICE REALTY OF GALENA

  11620 E Charles Rd, Mount Carroll, IL 61053
• 

  

  /46

  $469,990

  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
• 

  

  /46

  $90,000

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft

  229 N Milton Ave Unit 1, Springfield, IL 62702

  Opportunity, versatility, and space all come together at 229 Milton! This 2 bedroom, 2 bath brick ranch offers a full basement, an oversized 2 car garage, and an ultra-deep, fully fenced lot with an additional detached studio/dwelling that opens the door to a variety of possibilities. The detached studio would make an excellent rental opportunity, guest space, home office, or creative workspace,

  Logan Frazier The Real Estate Group, Inc.

  

  229 N Milton Ave Unit 1, Springfield, IL 62702
• 

  

  /72

  $590,000

  • 6 Beds
  • 4 Baths
  • 5,000 Sq Ft

  1333 Ottawa Ave, Ottawa, IL 61350

  ONE-OF-A-KIND HISTORIC HOME WITH GUEST HOUSE. Step into a remarkable piece of history with this stately John Nash home, listed on the Historic Register. Rich in architectural character and offering incredible versatility, the main residence and separate guest house together feature 6 bedrooms, 5 bathrooms and 3 kitchens-creating endless possibilities for extended family, guests, private living

  Theresa Poundstone Coldwell Banker Real Estate Group

  1333 Ottawa Ave, Ottawa, IL 61350
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  /88

  $595,000

  $90K PRICE DROP

  • 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
• 

  

  /53

  $624,900

  Pending

  • 5 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2038 N 43rd Rd, Leland, IL 60531

  3 Acre Horse Property! Country Living at it's finest. This property has two homes. The main house is a 5 Bedroom 2 Bath home. Major updates include. New roof was redone in 2025 including a tear off. New furnace and a/c replaced in 2023. Water heater in 2025. Also a 2nd furnace for the mudroom and master bedroom. These rooms were included in the addition in 2003. This addition also included the

  George Kleinprinz Swanson Real Estate

  2038 N 43rd Rd, Leland, IL 60531
• 

  

  /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
• 

  

  /17

  $84,500

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  134 N Douglas Ave, Belleville, IL 62220

  SELLER SAYS BRING OFFER. Fantastic Opportunity to live in main home and have 1 bedroom rental in rear. Home has 3 large bedrooms and 1 full and 1 3/4 bath with main level laundry. Needs cosmetics but home has some updates throughout. Rear home is 1 bed and 3/4 bath with living room and kitchen. Would be great additional income. ( 600 to 650 per month) Huge corner lot in a historical neighborhood

  Carlee Stanley eXp Realty

  134 N Douglas Ave, Belleville, IL 62220
• 

  

  /53

  $699,000

  Pending

  • 6 Beds
  • 3.5 Baths
  • 4,103 Sq Ft

  6A6 Hampton Ct, Apple River, IL 61001

  Welcome to this exceptional, meticulously maintained lake home with many recent updates offering privacy and a transferable boat dock (6-6-8) just beyond the home via a short private path. Nestled on two beautifully landscaped lots totaling 1.32 acres and bordered on the rear and side by 7.98 acres of green space, this remarkable property provides an unparalleled setting. Flexible floor plan

  Michelle Bass DC Rise Real Estate

  6A6 Hampton Ct, Apple River, IL 61001
• 

  

  /33

  $269,900

  Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,081 Sq Ft

  619 Thomas St, Edwardsville, IL 62025

  Coming Soon! OPEN HOUSE Saturday, August 29th, 11 am. - 1 pm. 619 Thomas Street has so much to offer! This property includes an updated single family home PLUS guest house! The main house features 3 bedrooms & 2 baths, with 1491 Sq Ft. Includes spacious living room, laundry room, eat in kitchen with tile backsplash & stainless steel appliances. Large primary bedroom has walk in closet, 3/4

  Lacey and Brent Dore RE/MAX Signature Properties

  619 Thomas St, Edwardsville, IL 62025
• 

  

  /78

  $2,295,000

  • 4 Beds
  • 4.5 Baths
  • 6,440 Sq Ft

  373 W County Line Rd, Barrington, IL 60010

  A truly exceptional Barrington Hills estate where architectural heritage, extraordinary gardens and timeless country living come together. The main residence features 4 bedrooms, 4.1 bathrooms and 5 fireplaces, complemented by a charming 1-bedroom guest home offering approximately 800 sq ft of additional living space. Set on nearly 6 extensively landscaped acres and surrounded by conservation on

  John Morrison @properties Christie's International Real Estate

  373 W County Line Rd, Barrington, IL 60010
• 

  

  /25

  $259,000

  $11K PRICE DROP

  • Studio
  • 3,024 Sq Ft

  411 E Sycamore St, Elizabeth, IL 61028

  REDUCED! Discover an exceptional investment opportunity or owner-occupied duplex offering generous living space, versatile layouts, and excellent income potential. Unit 413 features an expansive 2,016 square feet with 3 bedrooms and 2 full bathrooms. This spacious home includes a welcoming main level featuring 2 bedrooms, 1 bathroom, and living room, dining area and kitchen plus a finished lower

  Justin Bauer JIM SULLIVAN REALTY

  411 E Sycamore St, Elizabeth, IL 61028
• 

  

  /93

  $1,199,990

  $300K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,733 Sq Ft

  2373 Geddes Rd, Rockford, IL 61103

  PERTINENT FACTS: OPPORTUNITY TO OWN RARE, 11.5 (MOL) ACRES WITH ITS 2.5 ACRE STOCKED POND, W/3 BDRM, 2.5 BTH MAIN HOUSE, 2 BDRM, 1 BTH RENTAL HOUSE, 1 BDRM, 1 BTH CARETAKERS UNIT AND 2.5 ACRE PRIVATE, FERTILE, STOCKED POND!!! PARK-LIKE, PICTURESQUE setting great for water activities, camping, fishing, picnicking...come enjoy a hammock between the trees, WATCH STARS FROM THE WATERSIDE GAZEBO....

  Andrew Kordash Berkshire Hathaway HomeService

  2373 Geddes Rd, Rockford, IL 61103

Showing Results 41 - 80, Page 2 of 5