Illinois Homes for Sale with a Guest House

/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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/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
/68
$3,175,000
- 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
/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
/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

Jana Pierce Real Broker LLC

5930 S King Dr, Chicago, IL 60637
/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
/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
/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
/99
$1,300,000
- 9 Beds
- 9 Baths
- 15,500 Sq Ft
409 N State St, Franklin Grove, IL 61031

Welcome to a truly rare property - a gorgeous fully renovated 1913 residence paired with two additional custom-built homes, creating a multi-building estate with limitless potential. Thoughtfully restored and professionally updated inside and out, the main house spans over 10,000 square feet across four beautifully finished levels and offers six bedrooms, a library office, generous living spaces,

Linda Feinstein Compass

409 N State St, Franklin Grove, IL 61031
/94
$435,000
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
3881 E Tank Farm Ln, Olney, IL 62450

A Sportsman's paradise near Olney! Escape to your own private retreat on 40 beautiful acres just north of Olney. This unique property features two separate living quarters , making it perfect for multi-generational living, guests, or rental income. The main home, built in 2014, is part of a spacious barndominium measure 72' x 42'.Inside you'll find nearly 1,400 sq. ft. of comfortable living

Rebecca Miller Richland County Realty

3881 E Tank Farm Ln, Olney, IL 62450
/58
$634,900
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
21184 Allentown Rd, Pekin, IL 61554

The impressive 3,000+ sq. ft. outbuilding (built in '22) is the true centerpiece of this unique property—perfect for a business, hobbyist, workshop, or incredible recreational space. Designed with quality in mind, it features heated floors, 8-in. thick insulated steel-lined walls, and a 22-in. insulated ceiling. The building also includes two apartments—a fully finished 600 sq. ft. unit and a

Kristine Kniep RE/MAX Traders Unlimited

21184 Allentown Rd, Pekin, IL 61554
/50
$789,000
- 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
/36
$560,000
- 13 Beds
- 5 Baths
8705 S Saginaw Ave, Chicago, IL 60617

Great opportunity for investors or owner-occupants looking to maximize rental income potential! This unique multi-unit property features a main building with two spacious duplex units plus a separate coach house, offering multiple streams of income. The first duplex combines the main level with the basement and offers 6 bedrooms and 2 bathrooms, providing ample space for large households or

Lorena Ramirez-Carrillo YUB Realty Inc

8705 S Saginaw Ave, Chicago, IL 60617
/17
$315,000
- 2 Beds
- 1 Bath
- 857 Sq Ft
306 S Lincoln St, Elwood, IL 60421

GREAT CASH FLOW INVESTMENT OPPORTUNITY! Single-family home featuring an additional detached second residence on the same parcel. Each home offers 2 bedrooms and 1 bath with separate utilities and individual driveways. One home is currently rented at $1,600/month (month-to-month) providing immediate income, while the second unit is rent-ready and previously rented for $1,800/month. The 103' x 155'

Heather Schmidt AXEN Realty

306 S Lincoln St, Elwood, IL 60421
/56
$225,000
- Studio
- 2,870 Sq Ft
434 16th Ave, Rockford, IL 61104

TURN KEY DUPLEX IN ROCKFORD offering a great investment opportunity! This well-maintained property features two spacious 3-bedroom, 1-bath units. Interior highlights include hardwood floors, updated bathrooms, and freshly painted kitchens. The property also offers a full basement, fenced backyard, storage shed, and a 2-car garage. Conveniently located near schools, dining, and everyday amenities.

Fidel Batres Keller Williams Realty Signature

434 16th Ave, Rockford, IL 61104
/105
$2,150,000
- 5 Beds
- 4.5 Baths
- 4,084 Sq Ft
708 S Rose Farm Rd, Woodstock, IL 60098

20-Acre Equestrian Estate with Updated Farmhouse, Apartment & Professional Facilities. Set on a picturesque hill and surrounded by original stone fencing, this exceptional equestrian property offers the rare combination of a beautifully restored farmhouse and fully equipped professional horse facilities. The 5-bedroom, 4.1-bath home features over 4,000 sq ft of living space with hardwood

Kim Alden Compass

708 S Rose Farm Rd, Woodstock, IL 60098
/20
$45,000
- 3 Beds
- 1.5 Baths
909 W Center St, Fairfield, IL 62837

Conveniently located in town, this 3 bedroom, 1.5 bath home offers great potential. The property includes a carport and solid layout, making it a great opportunity for investors or buyers looking for a home they can update and make their own.

Ethan Keyser Keys Real Estate

909 W Center St, Fairfield, IL 62837
/63
$6,250,000
- 7 Beds
- 9 Baths
- 7,383 Sq Ft
1650 Green Bay Rd, Lake Bluff, IL 60044

On the market for the first time in nearly 50 years, the historic Phelps Kelley House is one of Lake Bluff's most significant estate properties. Designed in 1927 by noted Chicago architect Ambrose Cramer, a protege of David Adler, this Tudor Revival masterpiece was originally part of the historic "Stonebridge" estate. The 9.35-acre property is elegantly situated at the end of a long, private,

Annie Lenzke Coldwell Banker Realty

1650 Green Bay Rd, Lake Bluff, IL 60044
/31
$1,200,000
- 8 Beds
- 10 Baths
- 11,108 Sq Ft
3736 S Michigan Ave, Chicago, IL 60653

A mansion in Bronzeville, built in the 19th century for a leading grain dealer and later used as a Black-owned hospital, is on the market for the first time in three decades, sold by a woman who has carefully restored many of its ornate historical finishes.Take a look back into the 19th century with this architectural masterpiece. Located in Chicago's historic Bronzeville neighborhood, this

Michael Giliano Compass

3736 S Michigan Ave, Chicago, IL 60653
/83
$995,000
- 4 Beds
- 1.5 Baths
- 1,959 Sq Ft
4917 Wayside Dr, McHenry, IL 60051

Tucked away on a quiet country road, this expansive 4917 Wayside property in McHenry offers the space and flexibility so many people are looking for. Set on large, fully fenced acreage, it features a comfortable all-brick ranch-style home surrounded by open land, barns, sheds, storage and multiple paddocks--perfect for those who want room to spread out, work and keep animals or live the

Amy Foote Compass

4917 Wayside Dr, McHenry, IL 60051
/48
$899,900
- 4 Beds
- 6 Baths
- 5,549 Sq Ft
15792 E Seven Oaks Cir, Effingham, IL 62401

1 of a Kind: 7.48ac Estate complete with 3600+sq. ft. home with full finished walkout lower level with full kitchen that takes you to the inground pool (heated, saltwater, fiberglass pool from W.E.T.) surrounded by large concrete patio, and pavilion overlooking 7+acres of trees and pasture. Back pasture suitable for horses, ATVs, play area, etc. Inside you'll find the Great Room with large

Kelly Butts KB Appraisals & Realty

15792 E Seven Oaks Cir, Effingham, IL 62401
/14
$5,900,000
- 6 Beds
- 9 Baths
- 6,500 Sq Ft
395 Greenleaf Ave, Glencoe, IL 60022

Impeccable showcase all brick home with separate coachhouse on .8 acre beautiful property located on of the finest streets in East Glencoe. Featured in House Beautiful magazine, the main house has been elegantly renovated to include Parisian tile, an expanded kitchen, and all new bathrooms. Gourmet kitchen with double thick Quartize counters, high end stainless steel appliances, and butlers

Margie Brooks Baird & Warner

395 Greenleaf Ave, Glencoe, IL 60022
/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
/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
/4
$175,000
- Studio
- 2,905 Sq Ft
4708 Forest Hills Rd, Loves Park, IL 61111

Unique 2-family property on one lot featuring an all-brick front home plus a separate back home attached to the garage. The front residence offers 3 bedrooms and 2 bathrooms, a spacious kitchen, dining room, office, and a bright living room with fireplace and hardwood flooring. The back home includes 2 bedrooms, 1 bathroom, living room, and kitchen. Fully occupied with long-term tenants in place.

Olga Kampmeier Keller Williams Realty Signature

4708 Forest Hills Rd, Loves Park, IL 61111
/46
$319,900
- 4 Beds
- 3 Baths
- 1,825 Sq Ft
1416 6th St, Orion, IL 61273

Welcome to this exceptional brick ranch in Orion, where timeless craftsmanship meets thoughtful modern updates. Impeccably maintained and move-in ready, this expansive home offers 4 bedrooms, 3 full bathrooms, and a truly remarkable 3-car garage with fully finished living quarters... it keeps going! All cabinets (in both kitchens) along with the vanities are all custom Amish cabinets. An

Ted Leuck Ruhl&Ruhl REALTORS Moline

1416 6th St, Orion, IL 61273
/24
$219,000
- 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
/71
$2,500,000
- 5 Beds
- 4.5 Baths
- 7,823 Sq Ft
23 W County Line Rd, Barrington, IL 60010

Welcome to Shamrock Farm, an exquisite 13.4-acre equestrian estate in the heart of Barrington Hills, where luxury living meets world-class equestrian facilities. Whether an owner or trainer, this is a horse enthusiasts dream and offers unparalleled amenities, breathtaking views, all in a prime location. The stunning main residence showcases classic Antebellum architecture & is a masterpiece of

Dean Tubekis Coldwell Banker Realty

23 W County Line Rd, Barrington, IL 60010
/44
$969,000 Open Sat 11AM - 1PM
- 4 Beds
- 5 Baths
- 3,500 Sq Ft
629 N Lincoln Ave, Geneva, IL 60134

Completely remodeled to the highest standards, this home is a stunning example of modern luxury. This property offers a prime location just a few blocks from everything downtown Geneva has to offer. Nestled on a quiet street, the home combines privacy with convenience, providing easy access to local amenities and attractions including being just moments away from the Chicago commuter train,

Cory Jones eXp Realty - St. Charles

629 N Lincoln Ave, Geneva, IL 60134
/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
/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
/17
$45,000
- 2 Beds
- 1 Bath
- 920 Sq Ft
1020 N Laurel St, Fairfield, IL 62837

This 2 bedroom, 1 bath home offering 920± sq ft of living space. Features include a carport and new appliances. A great opportunity for a buyer looking to personalize and make it their own.

Ethan Keyser Keys Real Estate

1020 N Laurel St, Fairfield, IL 62837
/33
$340,000
- 4 Beds
- 3 Baths
- 1,662 Sq Ft
1046 State 32 Hwy, Sullivan, IL 61951

Fully Renovated Ranch Near Lake Shelbyville! ***This versatile property offers not only comfortable living but also excellent income potential*** Whether you’re looking to offset your mortgage or invest in a steady revenue stream, this property provides a great opportunity to generate additional income while enjoying the benefits of homeownership.Located just outside of town and less than a

Jennifer Underwood THATS A WRAP REALTY

1046 State 32 Hwy, Sullivan, IL 61951
/73
$2,750,000
- 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
/39
$1,150,000
- Land
- 9.6 Acres
- $119,792 per Acre
330 S Barrington Rd, Barrington, IL 60010

If every day you could be presented with the opportunity to live your best life shoreside, would you take it? it's irresistible and something so radically different while set within the confines of solitude. Short of 10 acres this property offers the magical holistic healing approach with the calming sounds of water passing under the bridge from one pond to another. A sprawling ranch overshadows

Rob Morrison Coldwell Banker Realty

330 S Barrington Rd, Barrington, IL 60010
/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
/18
$425,000
- Studio
- 4,162 Sq Ft
129 N 2nd St, Rockford, IL 61107

Exceptional opportunity to own a classic brick multifamily in heart of downtown Rockford where walkability, character, and investment potential come together. Charming building offers four spacious one-bedroom units featuring tall ceilings and large windows allowing lots of natural light, hardwood floors, remodeled kitchens and fresh updates throughout. The basement is in the process of being

Christine Smith Real Broker, LLC

129 N 2nd St, Rockford, IL 61107
/49
$1,800,000
- 5 Beds
- 4.5 Baths
2845 W Division St, Chicago, IL 60622

Stunning, massive graystone with a 2-unit coach house overlooking Humboldt Park. The main house was meticulously rehabbed and features fantastic quality and custom vintage inspired details throughout. Huge rooms with large bay windows, 4 separate living spaces, 5 bedrooms and 4.1 bathrooms with abundant storage. The facade is stunning, with ornate limestone details and huge windows looking into

Lucas Blahnik @properties Christie's International Real Estate

2845 W Division St, Chicago, IL 60622
/66
$1,125,000
- 3 Beds
- 2.5 Baths
- 2,507 Sq Ft
5382 Guilford Rd, Rockford, IL 61107

Welcome to an extraordinary opportunity nestled behind private gates at 5382 Guilford Rd in Rockford. This remarkable agricultural property offers 4.23 acres and is the perfect blend of country serenity and modern convenience, all within reach of urban amenities. The main residence features 3 spacious bedrooms and 2.5 bathrooms, providing comfortable living quarters for the discerning buyer

John & Diane Dowd DICKERSON & NIEMAN

5382 Guilford Rd, Rockford, IL 61107

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Illinois Homes for Sale with a Guest House

Real Estate & Homes for Sale in Illinois