Winchester, IL homes for sale & real estate

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ABOUT THIS HOME
Winchester, IL Homes for Sale
A handyman’s dream, this home has tons of potential! It offers two official bedrooms, but functionally is being used as a three bedroom with the former family room being used as a bedroom. Home also includes a large living room with hardwood floors, eat-in kitchen, full bath and enclosed back entry. An unattached 22×20 garage all on a corner lot measuring approximately 80’x90'. Selling As-Is, inspections welcome.

$59,500

3 beds1 bath1,392 sq ft

33 N Maple St, Winchester, IL 62694

Unattached garage • Eat-in kitchen • Enclosed back entry

ABOUT THIS HOME
Winchester, IL Homes for Sale
Escape to your own private retreat with this 2-story log cabin set on 29 +/- wooded acres. Featuring 3 bedrooms and 2.5 baths, the home boasts an open kitchen and main living area with rustic charm, and plenty of natural light. Enjoy the outdoors from not one, but two massive walk-out decks on both the main and upper levels—perfect for entertaining or simply taking in the serene views. The property offers mature timber, abundant wildlife, and a storage shed, making it an ideal spot for recreation, hunting, or a peaceful getaway. Secluded setting with only one nearby neighbor on a large tract of timber ensures privacy while still being within reach of town.

$399,900

3 beds2.5 baths1,771 sq ft

759 Big Swan Rd, Winchester, IL 62694

Mature timber • 29 wooded acres • Abundant wildlife

ABOUT THIS HOME
Winchester, IL Homes for Sale
Opportunity awaits! Situated on an acre across multiple parcels, this versatile property features a 3-bedroom, 1-bath home, a mobile home, and an oversized block-construction 3-car garage/workshop. Step inside the main home and envision the charm and potential waiting to be brought to life. The spacious gravel driveway provides plenty of room for multiple vehicles, trailers, or equipment. The 1,600 sq ft garage/workshop is a standout feature, perfect for storage, hobbies, or a home-based business. Enjoy the added bonus of a peaceful creek running along the back of the property, bringing a touch of nature to your backyard. Property is being sold AS-IS. Don’t miss this unique opportunit

$75,000

3 beds1 bath1,231 sq ft

55 N Commercial St, Winchester, IL 62694

Peaceful creek • 1 acre lot • 3 garage spots

ABOUT THIS HOME
Winchester, IL Homes for Sale
This 650± sq. ft. home at 111 W Cross Street in Winchester, Illinois, offers efficient, low-maintenance living with two bedrooms, one bathroom, and an open-concept kitchen and living area. Fully remodeled about five years ago, it features updated plumbing, electrical, flooring, and HVAC systems. The water heater and softener are around three years old, and all included appliances are five years old or newer. The small backyard allows space for pets or outdoor seating with minimal upkeep, and a compact metal shed provides extra storage. Street parking is available. Ideal as a starter home, rental, or downsizing option, this property offers practicality and modern reliability. Winchest

$60,000

2 beds1 bath650 sq ft

111 W Cross St, Winchester, IL 62394

Updated electrical • Open-concept kitchen • Small backyard

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ABOUT THIS HOME
Winchester, IL Homes for Sale
Welcome to 17 Windrush, a surprisingly spacious and beautifully updated home offering up to 8 potential bedrooms. The main floor features 3 bedrooms, while the upstairs includes 5 additional bedrooms, three of which have no closets, giving you fantastic flexibility for bedrooms, offices, hobby rooms, or play areas. With 3 full bathrooms, this home is designed to accommodate a crowd with ease. You’ll love the huge living room, perfect for gathering and entertaining, along with a bright loft area that adds even more usable space. The layout provides endless options for large families or anyone needing extra room to spread out. Outside, enjoy a newer fenced-in oversized lot, offering pri

$190,000

5 beds3 baths2,541 sq ft

17 Windrush Dr, Jacksonville, IL 62650

2 garage spots • Built 1973 • Listed 2 days

ABOUT THIS HOME
Winchester, IL Homes for Sale
Secluded on Cedar sits this remodeled ranch with 3 bedrooms and a finished basement! Since 2022 lots of remodeling has happened to the flooring, fixtures, kitchen, bath and more! The kitchen features butcher block counters, nice work space and an eating area. Head to the basement to a large rec room, 4th bedroom (no egress) or office, and half bathroom (could be a full). Outside has a NEW patio and spacious carport with storage shed. All this sitting in Eisenhower school district at an affordable price! Broker owned.

$157,500

3 beds1.5 baths1,708 sq ft

1835 Cedar St, Jacksonville, IL 62650

New patio • Remodeled ranch • Large rec room

ABOUT THIS HOME
Winchester, IL Homes for Sale
Step inside this charming 2-bedroom home. Loaded with warm wood floors that were recently refinished. Art Deco style metal cabinets with electric stove/oven included. Spacious formal dining room will accommodate large furniture. Front living room has a wood burning fireplace. Two bedrooms and a full bath are located at the East side of the home. Off the kitchen you can access a floored attic or the full unfinished basement with cold storage space, a drive through or double car tuck under garage. Gas furnace and hot water heater. Selling cash or conventional loan only. Seller will make no further repairs. Buyer may have inspections.

$45,000

2 beds1 bath1,271 sq ft

13960 State Hwy 100, Pearl, IL 62361

Cold storage space • Wood floors • Floored attic

ABOUT THIS HOME
Winchester, IL Homes for Sale
If you are looking for an open floor plan ranch in Grant's Meadow. .. .. look no further! This 3 bedroom 2.5 bathroom home will surely meet all your needs with a NEW HVAC in 2024, NEW roof in 2023, garage recently insulated heated and cooled and a large storage shed added! The screened back porch will surely be enjoyed with morning coffee and sunrises. The full unfinished basement has an egress window and ready for expansion! Main floor laundry, gas fireplace and a recently painted exterior make this home MOVE IN READY! Solar panels added in 2024 for energy efficiency and buyer will assume the lease at $136/mo with no increase. Come take a look!

$245,000

3 beds2.5 baths1,484 sq ft

22 Appomatox Ave, Jacksonville, IL 62650

Screened back porch • New hvac • New roof

ABOUT THIS HOME
Winchester, IL Homes for Sale
Affordable and full of potential, this 2-bedroom, 1-bath home sits on a spacious double corner lot in Roodhouse, IL. The layout includes a large mudroom at the back of the home, offering extra storage and everyday convenience. Outside, you'll find a detached garage and an additional detached carport, providing plenty of covered parking or workspace options. The property also includes a trailer on the lot. Inside, the home features fresh paint and new carpet throughout, giving you a clean slate to make it your own. This property could make a great first-time home buyer opportunity or a comfortable option for someone looking to downsize while still enjoying a generous outdoor space. Come take

$60,000

2 beds1 bath950 sq ft

338 W Rowe St, Roodhouse, IL 62082

0.42 acre lot • Garage • Built 1901

ABOUT THIS HOME
Winchester, IL Homes for Sale
A CHARMING 2 STORY ON FRIENDLY FINLEY - THIS ONE CHECKS ALL THE BOXES. BRICK AND STONE - STORY BOOK STREET - HANSEL N GRAETELL CURB APPEAL -CHARACTER - CHARM - EXPECTAIONS HIGH. .. FOLLOW THE STEPS TO THE ARCHED FRONT DOOR - OPEN UP TO GLISTENING HARDWOOD FLOORS-CROWN MOLDINGS-FRENCH DOORS-ARCHED DOOR OPENINGS & A BRICK FIREPLACE -THAT EXPECTED IN OUR 1930'S CHARMING HOMES ON FINLEY - WHAT IS NOT EXPECTED IS THE RENOVATED KITCHEN AND MASTER BATH. THE KITCHEN IS LIGHT BRIGHT MEDIUM WHITE - CUSTOM DESIGNED TASTEFULLY - UPDATED STAINLESS APPLAINCES (NEWER $3,000 FREFIGERATOR) KITCHEN IS OPEN TO THE INFORMAL DINING AREA AND VEIWS FINLEY STREET WITH ALL ITS MATURE TREES - A SITE TO BEHOLD

$269,900

3 beds2 baths2,286 sq ft

290 Finley St, Jacksonville, IL 62650

0.37 acre lot • 2 garage spots • Built 1931

Property at 307 Westwinds Dr, Jacksonville, IL 62650, 3 beds, 2.5 baths

$323,000

3 beds2.5 baths2,790 sq ft

307 Westwinds Dr, Jacksonville, IL 62650

Property at 310 Woodland Pl, Jacksonville, IL 62650, 2 beds, 1 bath

$135,000

2 beds1 bath1,200 sq ft

310 Woodland Pl, Jacksonville, IL 62650

Property at 1136 W State St, Jacksonville, IL 62650, 5 beds, 3.5 baths

$519,900

5 beds3.5 baths6,000 sq ft

1136 W State St, Jacksonville, IL 62650

Property at 121 City Pl, Jacksonville, IL 62650, 2 beds, 2 baths

$137,500

2 beds2 baths1,177 sq ft

121 City Pl, Jacksonville, IL 62650

Property at 12 Newland Ln, Jacksonville, IL 62650, 3 beds, 2.5 baths

$154,900

3 beds2.5 baths1,408 sq ft

12 Newland Ln, Jacksonville, IL 62650

Property at 400 Massey Ln, Jacksonville, IL 62650, 4 beds, 2.5 baths

$204,900

4 beds2.5 baths1,846 sq ft

400 Massey Ln, Jacksonville, IL 62650

Property at 207 Mound Pl, Jacksonville, IL 62650, 3 beds, 1 bath

$135,000

3 beds1 bath1,388 sq ft

207 Mound Pl, Jacksonville, IL 62650

Property at 1924 Cedar St, Jacksonville, IL 62650, 3 beds, 2 baths

$216,500

3 beds2 baths1,924 sq ft

1924 Cedar St, Jacksonville, IL 62650

Property at 220 E North St, Roodhouse, IL 62082, 3 beds, 1 bath

$70,000

3 beds1 bath1,262 sq ft

220 E North St, Roodhouse, IL 62082

Property at 33 Windrush Dr, Jacksonville, IL 62650, 3 beds, 2 baths

$139,900

3 beds2 baths1,404 sq ft

33 Windrush Dr, Jacksonville, IL 62650

Property at 304 Carobeth Cir, Jacksonville, IL 62650, 4 beds, 2 baths

$425,000

4 beds2 baths2,738 sq ft

304 Carobeth Cir, Jacksonville, IL 62650

Property at 1640 Old Highway 67, Chapin, IL 62628, 3 beds, 2 baths

$279,900

3 beds2 baths5,140 sq ft

1640 Old Highway 67, Chapin, IL 62628

Property at 1835 Mound Rd, Jacksonville, IL 62650, 4 beds, 3 baths

$439,900

4 beds3 baths2,528 sq ft

1835 Mound Rd, Jacksonville, IL 62650

Property at 1401 Hoagland Blvd, Jacksonville, IL 62650, 3 beds, 1 bath

$90,000

3 beds1 bath882 sq ft

1401 Hoagland Blvd, Jacksonville, IL 62650

Based on information submitted to the MLS GRID as of Mon Nov 24 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Winchester, IL

Cities

White Hall homes for sale
$74,750
South Jacksonville homes for sale
$142,400
Meredosia homes for sale
Pittsfield homes for sale
$175,000
Chapin homes for sale
$63,500
Roodhouse homes for sale
$70,000
Jacksonville homes for sale
$152,400

Zip Codes

62694 homes for sale
$67,500

Winchester, IL real estate trends

$82K

Sale price

$66

Sale $/sq ft

Under list price

9.9%

Days on market

Down payment

—

Total homes sold

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