Winchester, IL homes for sale & real estate

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638 N Main St, Winchester, IL 62694
638 N Main St, Winchester, IL 62694
638 N Main St, Winchester, IL 62694
ABOUT THIS HOME
Winchester, IL Homes for Sale
This modern oasis may sit in the city limits, but has the look and feel of a private country getaway. Almost 3,800 square foot of finished living space. High ceilings and almost 1,200 sq ft work shop - currently an embroidery business, could easily be your pool house. Home has Geothermal, hardwood throughout most of the home, luxury vinyl in most of the rest. Granite counters. Main floor is open floorplan, large master bedroom, bathroom, and walk in closet. So much potential in the upstairs main area. Could be used as gaming area, or playroom. Large bedrooms connected by full Jack and Jill bathroom! Finished basement perfect for the family and egress bedroom. Mudroom/laundry and 1/2 bath is

$434,000

4 beds3.5 baths3,735 sq ft

638 N Main St, Winchester, IL 62694

1.32 acre lot • 3 garage spots • Pool

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510 S Westgate Ave, Jacksonville, IL 62650
510 S Westgate Ave, Jacksonville, IL 62650
510 S Westgate Ave, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
This lovely ranch home is the one you've been waiting for. The main living areas and bedrooms feature updated flooring, and the bathroom has been totally updated with modern touches. The large family room hosts a beautiful brick fireplace. There is plenty of extra storage space in the unfinished basement. Hurry to see this home before it is too late!

$175,000

3 beds1 bath1,642 sq ft

510 S Westgate Ave, Jacksonville, IL 62650

8,970 sq ft lot • Garage • Somewhat walkable

1325 W College Ave, Jacksonville, IL 62650
1325 W College Ave, Jacksonville, IL 62650
1325 W College Ave, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
STORY BOOK 1.5 STORY BUNGALOW. THIS ONE IS CHOCKED FULL OF PERSONALITY. CHARACTER & CHARM - CHICAGO STYLE COVERED PORCH WELCOMES YOU. SAY HELLO TO HANDSOME REFINISHED HW FLOORS - LARGE ENTRY HALL VIEWS THE 22X17 LIVING ROOM W/ A TRADITIONAL FP & A COZY LIGHT-BRIGHT READING SPOT WHERE THIS OWNERS GREEN THUMB SHOWCASES HER FLOURISHING PLANTS - MAIN FLOOR: FORMAL DINING AREA W/ A STATEMENT STAIRCASE ADDING TO THE COTTAGE CHARM - THE KITCHEN LEANS RETRO - A GREAT STEP BACK IN TIME - LOVE THE PLATFORM COUNTERS - WHITE CABINETS - CENTER ISLAND IS NEGOTIABLE - ITS A MUST-IT MAKES THE AREA -TALL CABINETS LINE PART OF THE BACK WALL - TILED COUNTERS & BACKSPLASH - ITS THE HEART OF

$224,900

4 beds2 baths3,090 sq ft

1325 W College Ave, Jacksonville, IL 62650

2 garage spots • Car-dependent

231 N Webster Ave, Jacksonville, IL 62650
231 N Webster Ave, Jacksonville, IL 62650
231 N Webster Ave, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
Welcome to a slice of Jacksonville history. 231 N Webster is a grand 'ol home! Yes, it's charming and yes, it's oozing with character. Built like a home should be built. Full attic for storage or additional square feet and the basement is a very usable and cool space. So many beautiful features. .. hardwood floors, original woodwork, pocket doors, covered front porch. .. .full of memories. Add a nicely updated kitchen, main floor home office, updated baths, updated HVAC (2023), gorgeous covered deck just off the kitchen and you have it all! Wonderful opportunity!

$215,000

3 beds1.5 baths3,080 sq ft

231 N Webster Ave, Jacksonville, IL 62650

0.31 acre lot • 2 garage spots • Car-dependent

3 Ivywood Dr, Jacksonville, IL 62650
3 Ivywood Dr, Jacksonville, IL 62650
3 Ivywood Dr, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
Charming Brick Cape Cod in Coveted West End! Welcome to this attractive 4-bedroom, 2.5-bath home nestled in the quiet and highly sought-after West End neighborhood. Featuring a desirable main floor master suite, this classic brick Cape Cod blends timeless character with modern comfort. The galley-style kitchen comes equipped with appliances and flows seamlessly into the main living area, where updated flooring adds a fresh, contemporary feel. Upstairs you’ll find additional bedrooms and generous attic space—perfect for storage or ready to finish for even more living area. A full unfinished basement offers further potential. With a new HVAC system just months old, this home is mo

$230,000

4 beds2.5 baths1,940 sq ft

3 Ivywood Dr, Jacksonville, IL 62650

0.33 acre lot • 2 garage spots • Car-dependent

506 Sandusky St, Jacksonville, IL 62650
506 Sandusky St, Jacksonville, IL 62650
506 Sandusky St, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
Charming all brick cottage style, updated kitchen and bath, hardwood floors and tile, deep lot, full basement and finished attic. Roof and furnace updated. Large backyard. Partially fenced for pets. Located in Eisenhower School District. Home is sold as is. Inspections welcome.

$109,000

3 beds1 bath864 sq ft

506 Sandusky St, Jacksonville, IL 62650

0.3 acre lot • Car-dependent

904 E Roodhouse Rd, Roodhouse, IL 62082-4116
904 E Roodhouse Rd, Roodhouse, IL 62082-4116
904 E Roodhouse Rd, Roodhouse, IL 62082-4116
ABOUT THIS HOME
Winchester, IL Homes for Sale
Discover the perfect blend of comfort, space, and rural charm with this all-electric country home on 12 scenic acres. Featuring 4 spacious bedrooms and 3 full bathrooms, this home offers ample room for family and guests with thoughtful details throughout. Enjoy peaceful mornings on the welcoming front porch overlooking the countryside. Inside, the cozy living room with fireplace flows into a kitchen with plenty of counter space and a formal dining room—ideal for gatherings. Two living areas provide flexible space to relax or entertain. Step outside to the large back deck or the walk-out basement patio, perfect for enjoying views or grilling. The expansive walk-out basement offers endl

$519,000

4 beds3 baths4,284 sq ft

904 E Roodhouse Rd, Roodhouse, IL 62082-4116

12 acre lot • 2 garage spots • Car-dependent

Property at 1249 W State St, Jacksonville, IL 62650, 5 beds, 4 baths

$444,000

5 beds4 baths5,451 sq ft

1249 W State St, Jacksonville, IL 62650

Property at 101 Cottage Ln, Murrayville, IL 62668, 3 beds, 1.5 baths

$67,500

3 beds1.5 baths1,512 sq ft

101 Cottage Ln, Murrayville, IL 62668

Property at 8 Westfair Dr, Jacksonville, IL 62650, 5 beds, 2 baths

$184,000

5 beds2 baths2,064 sq ft

8 Westfair Dr, Jacksonville, IL 62650

Property at 115 Jackson St, Winchester, IL 62694, 2 beds, 1 bath

$34,900

2 beds1 bath2,259 sq ft

115 Jackson St, Winchester, IL 62694

Property at 18 Jacobs Ln, Jacksonville, IL 62650, 4 beds, 4.5 baths

$449,900

4 beds4.5 baths8,140 sq ft

18 Jacobs Ln, Jacksonville, IL 62650

Property at 238 E Prairie St, Roodhouse, IL 62082, 4 beds, 2 baths

$142,500

4 beds2 baths3,160 sq ft

238 E Prairie St, Roodhouse, IL 62082

Property at 1752 Duncan Rd, Murrayville, IL 62668, 4 beds, 2.5 baths

$350,000

4 beds2.5 baths1,879 sq ft

1752 Duncan Rd, Murrayville, IL 62668

Property at 0 Bridge Is, Pearl, IL 62361

$45,000

0 beds— baths— sq ft

0 Bridge Is, Pearl, IL 62361

Property at 510 Westwinds Dr, Jacksonville, IL 62650

$32,900

— beds— baths— sq ft

510 Westwinds Dr, Jacksonville, IL 62650

Property at County HWY 10 0, Pearl, IL 62361

$1,818,000

— beds— baths— sq ft

County HWY 10 0, Pearl, IL 62361

Property at 801 NW 1200 St, Hillview, IL 62650

$2,022,600

— beds— baths— sq ft

801 NW 1200 St, Hillview, IL 62650

Property at 72 Applebee Farms Dr, Jacksonville, IL 62650

$34,900

— beds— baths— sq ft

72 Applebee Farms Dr, Jacksonville, IL 62650

Property at 70 Applebee Farms Dr, Jacksonville, IL 62650

$34,900

— beds— baths— sq ft

70 Applebee Farms Dr, Jacksonville, IL 62650

Property at 68 Applebee Farms Dr, Jacksonville, IL 62650

$34,900

— beds— baths— sq ft

68 Applebee Farms Dr, Jacksonville, IL 62650

Based on information submitted to the MLS GRID as of Tue Jul 15 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

Pearl homes for sale
South Jacksonville homes for sale
$167,500
Griggsville homes for sale
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Jacksonville homes for sale
$159,900

Winchester, IL real estate trends

$74.9K

Sale price

$39

Sale $/sq ft

Over list price

Days on market

Down payment

—

Total homes sold

See more Winchester, IL market insights

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