Winchester, IL homes for sale & real estate

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ABOUT THIS HOME
Winchester, IL Homes for Sale
Character, charm, and all the right updates — this 4-bed, 2-bath home in the heart of Winchester, IL checks every box. Nestled in a welcoming small town where neighbors still know your name, this home offers the best of both worlds — timeless character and modern peace of mind. Approximately 2,000 sq. ft. features gorgeous original woodwork, built-ins, and sun-filled rooms. Major systems updated 2016–2018 (roof, wiring, plumbing & floors), new water heater (2024), stainless kitchen with new double oven (2026) and dishwasher (2025), and two refreshed full baths — one with a jetted tub. Outside: above-ground pool with newer pump included, entertaining patio, matu

$134,900

4 beds2 baths2,080 sq ft

200 S Main St, Winchester, IL 62694

New water heater • Sun-filled rooms • Stainless kitchen

ABOUT THIS HOME
Winchester, IL Homes for Sale
Unique & charming describe this one of a kind 3 bedroom home with an open, airy floor plan. Windows along the entire front of house allow natural light throughout the house. The kitchen offers counter space with seating on the opposite side while open to the living room. The master bedroom has space for a small sitting area and opens into an ensuite bathroom with a custom tile shower, with a built-in bench as well as a walk-in closet. The home features built-in shelving; an 18 foot dark grain, wood ceiling in the living room (and 2 bedrooms) with a ceiling fan; gorgeous open staircase; recessed ceilings & stain glass inserts add interesting, attractive additions to rooms. The cu

$129,900

3 beds2 baths1,808 sq ft

204 S Main St, Winchester, IL 62694

Built in bench • Open airy floor plan • Built in shelving

ABOUT THIS HOME
Winchester, IL Homes for Sale
Auction Listing: This is an attractive collection of five adjoining land tracts totaling 187.05± acres in Western Scott County, Illinois approximately 1.0± mile East of where I-72 and Route 100 intersect. Each tract is affordably-sized, each offering unique benefits to future owners. Whether you're looking for an entirely tillable tract of farmland, pastureland, woodland, or some combination of all, at least one of these tracts has something for you! Farmland doesn't change hands on the open market very often in this area, so don't miss this opportunity! All tracts are open for the 2027 crop season. The farms will sell in the Buyer's Choice format. Live In-Person & Onlin

Unknown

Land187.05 acres (lot)

Mcglaughlin Rd, Winchester, IL 62694

Income-producing • Pastureland

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ABOUT THIS HOME
Winchester, IL Homes for Sale
THIS CUTE COTTAGE ON FAIRVEIW TERRACE WILL STEAL YOUR HEART! CHOCKED FULL OF CHARACTER AND CHARM IT SCREAMS WITH PERSONALITY -THE LOT IS CLOSE TO . 05 ACRE - A RARE FIND IN THE MIDDLE OF TOWN-THIS CHARMING COTTAGE IS NESTLED IN A FOREST OF GORGEOUS TRESS, SHRUBS, FLOWERS, STONE WALK WAYS, TRELLISES, ARBORS-ITS ENCHANTING. THE DIFFERENCE IS ALWAYS IN THE DETAILS - OWNED BY THE FAYE / POWERS FAMILY THEY CONTRACTED CLARK WAGNER AND TODD OLSON TO RENOVATE - THEY DID AN OUTSTANDING JOB. MODERNIZING BUT KEEPING IN THE VEIN OF THE ORIGINAL HOME. .THE KITCHEN W/ CRAFTSMAN STYLE CABINETS & SOLID SURFACE COUNTERS IS AMAZING +IT IS OPEN TO A FAMILY ROOM-FEATURING A VAULTED CEILING W/ AN ARCHI

$237,500

2 beds2 baths1,865 sq ft

2 Fairview Ct, Jacksonville, IL 62650

Stone walk ways • Close to 05 acre • Vaulted ceiling

ABOUT THIS HOME
Winchester, IL Homes for Sale
WELCOME TO THE HIGHLY REGARDED APPLEBEE FARMS COMMUNITY! #24 WADSWORTH IS OFFICIALLY ACTIVE. FLORIDA INFLUENCED RANCH - THIS CLASSIC RANCH OWNS "CURB APPEAL" THE INTENTIONAL GABLED ROOF LINES ADD DRAMA - STEP IN - SITE LINES FROM THE IMPRESSIVE MARBLE ENTRY FOYER GO STRAIGHT TO THE WALL OF WINDOWS & SLIDING PELLA DOORS THAT OFER PRICELESS VIEWS OF K'S CREEK GOLF COURSE - OH THE FUN OF LIVING AT APPLEBEES ON THE GOLF COURSE! YOU MUST GRAB A GOLF CART AND HEAD OVER TO THE 9 WHOLE COURSE OR MAKE YOUR RESERVATION FOR DRINKS OR DINNER - ITS A RARE OPPORTUNITY FOR SURE! WHAT ABOUT THE HOUSE? IT'S GREAT - CUSTOM 1996 BUILT HOME FEATURES 2200 SQ FT ON THE MAIN + 800 FINISHED IN T

$399,900

4 beds3 baths3,000 sq ft

24 Wadsworth Dr, Jacksonville, IL 62650

0.33 acre lot • 3 garage spots • Built 2003

ABOUT THIS HOME
Winchester, IL Homes for Sale
Nice corner lot. One level living. Detached garage. Home needs some updates.

$75,000

2 beds1.5 baths1,286 sq ft

328 S Pearl St, Bluffs, IL 62621

One level living • Corner lot • Detached garage

ABOUT THIS HOME
Winchester, IL Homes for Sale
Who needs 4 beds at an affordable price? Check this out. West end, Eisenhower School, 1 level. Nice back yard. Ready for a new owner.

$141,000

4 beds1.5 baths1,104 sq ft

9 Harmony Dr, Jacksonville, IL 62650

Back yard • 1 level • Eisenhower school

FLOOR PLAN

ABOUT THIS HOME
Winchester, IL Homes for Sale
Situated on the edge of town, this spacious ranch-style home offers comfortable living with plenty of room to gather, relax and enjoy the country life! Step outside and this property features a 6-stall horse barn, riding arena, pasture, and multiple outbuildings set up for horse owners, hobby farmers or anyone needing extra space for animals, toys, equipment or recreation! Sitting on approx 3.85 acres this home features a versatile floor plan with 3 living spaces, 4 large bedrooms, 2.5 bathrooms, a mud room and large laundry room. The owners suite boasts a large walk in closet and lavish bathroom with soaking tub and walk in shower. If you are looking to spread out without losing the conven

$435,000

4 beds2.5 baths2,932 sq ft

2390 Mound Rd, Jacksonville, IL 62650

Pasture • Riding arena • 3.85 acres

ABOUT THIS HOME
Winchester, IL Homes for Sale
Sharp 3 bed ranch on a quiet, West-end street. Updates including roof '24, sump pump, replacement windows. Solid 6 panel interior wood doors. Oversized garage - 48' deep! Generous sized back yard with storage shed. Eisenhower school district.

$159,000

3 beds1 bath960 sq ft

1862 Plum St, Jacksonville, IL 62650

Sump pump • Storage shed • Oversized garage

Property at 320 N State St, Roodhouse, IL 62082, 2 beds, 1 bath

$179,000

2 beds1 bath876 sq ft

320 N State St, Roodhouse, IL 62082

Property at 1423 W Lafayette Ave, Jacksonville, IL 62650, 3 beds, 2.5 baths

$167,900

3 beds2.5 baths1,827 sq ft

1423 W Lafayette Ave, Jacksonville, IL 62650

Property at 126 W Briggs Ave, Roodhouse, IL 62082, 2 beds, 1.5 baths

$121,000

2 beds1.5 baths968 sq ft

126 W Briggs Ave, Roodhouse, IL 62082

Property at 301 3rd St, Manchester, IL 62663, 1 bed, 1 bath

$84,900

1 bed1 bath515 sq ft

301 3rd St, Manchester, IL 62663

Property at 1915 Plum St, Jacksonville, IL 62650, 3 beds, 2 baths

$160,000

3 beds2 baths1,600 sq ft

1915 Plum St, Jacksonville, IL 62650

Property at 338 W Rowe St, Roodhouse, IL 62082, 2 beds, 1 bath

$50,000

2 beds1 bath950 sq ft

338 W Rowe St, Roodhouse, IL 62082

Property at 3 Forest Hill Dr, Jacksonville, IL 62650, 4 beds, 2.5 baths

$375,000

4 beds2.5 baths3,439 sq ft

3 Forest Hill Dr, Jacksonville, IL 62650

Property at 1144 500 E, Hillview, IL 62050, 1 bath

$82,000

Studio1 bath410 sq ft

1144 500 E, Hillview, IL 62050

Property at 312 Westwinds Dr, Jacksonville, IL 62650, 4 beds, 2.5 baths

$389,900

4 beds2.5 baths2,566 sq ft

312 Westwinds Dr, Jacksonville, IL 62650

Property at 806 Phillips Ferry Rd, Bluffs, IL 62621, 3 beds, 3 baths

$389,500

3 beds3 baths3,566 sq ft

806 Phillips Ferry Rd, Bluffs, IL 62621

Property at Merritt Blacktop Rd, Merritt, IL 62650

Unknown

Land141.25 acres (lot)

Merritt Blacktop Rd, Merritt, IL 62650

Based on information submitted to the MLS GRID as of Wed Aug 26 2026. 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
$99,500
South Jacksonville homes for sale
$147,450
Meredosia homes for sale
$169,900
Pittsfield homes for sale
$199,450
Roodhouse homes for sale
$121,000
Jacksonville homes for sale
$160,000

Zip Codes

62694 homes for sale
$129,900

Winchester, IL real estate trends

$64.9K

Sale price

-13.4%
since last year

$56

Sale $/sq ft

+43.6%
since last year

Under list price

1.8%

Days on market

Down payment

—

Total homes sold

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