MLS Listings for Sale in Winchester, IL

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ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
Cute bungalow style home in Winchester! Lots of updates in 2010 like wiring, drywall, windows and flooring. Updates to the bathroom and kitchen (appliances included). Large garage. Main floor has GFA/CA and upstairs is BB heat and window air. Roof in 2008. HVAC 2001. Great starter or investment property. Selling AS IS.

$65,000

4 beds1 bath1,343 sq ft

11 N Commercial St, Winchester, IL 62694

Updates to kitchen • Large garage • Roof in 2008

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
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
MLS Listings for Sale in Winchester, IL
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

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
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

$82,000

3 beds1 bath1,231 sq ft

55 N Commercial St, Winchester, IL 62694

Peaceful creek • 1 acre lot • 3 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
If you want to live completely off the grid this country retreat is for you. It's powered by solar and water is hauled from a spring on the property. This 2 bedroom, 1 bath home with a huge 3 car attached garage/shop all on a little over 6 acres can make your dream come true!

$150,000

2 beds1 bath1,744 sq ft

1050 Mcglaughlin Rd, Winchester, IL 62694

Water from spring • Solar powered • Over 6 acres

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NEW 9 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
Absolutely adorable brick home across from the park. This charming 1.5 story, two bedroom, one-bath home is full of character. Enjoy beautiful hardwood floors, a cozy layout, and a deck off the back-perfect for entertaining. Surrounded by flowers and trees, this home feels like your own private garden retreat. The waterproofed basement includes laundry, plenty of windows for natural light, and a walk-up stairs door leading to the backyard. It's also plumbed for a second bathroom, offering very usable space and great potential for expansion. Fantastic location right across from the park-just adorable inside and out!

$135,000

2 beds1 bath1,200 sq ft

310 Woodland Pl, Jacksonville, IL 62650

5,000 sq ft lot • Garage • Car-dependent

COMING SOON

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
Coming Soon. All-brick ranch in desirable west-side location offering approx. 2,500 sq. ft. on the main level. Built by Claude Lemon with quality construction throughout. Traditional floor plan includes formal living and dining rooms, large eat-in kitchen, and family room with fireplace. Oversized primary bedroom features full bath and walk-in closet. Partial basement is partially finished and provides additional space for storage or future expansion. Exterior highlights include mature landscaping, covered front porch, and a spacious rear deck with covered seating area. Well-maintained property with main level laundry, updated HVAC 2021. Roof approx. 2012. New Sliding door in Family room. D

$329,900

3 beds2.5 baths2,790 sq ft

307 Westwinds Dr, Jacksonville, IL 62650

2 garage spots • Car-dependent

COMING SOON

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
COMING SOON - 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

$269,900

3 beds2 baths2,286 sq ft

290 Finley St, Jacksonville, IL 62650

0.37 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
STUNNING STATE ST. STUCCO - HISTORICAL DUNCAN PARK AREA. HOME TRANSCENDS ORDINARY. CURB APPEAL IS "TOWN AND COUNTRY" AT ENTRY THE MAGAZINE WORTHY LOOK BEGINS - IT IS RELAXED SOPHISTICATION - FRESH - CUSTOM - AMAZING - THE LOWER LEVEL HAS BEEN PAINTED IN LIGHTER WHITE TONES -SO IN STYLE - HOME FEATURES CHARACTER & CHARM MIXING BEAUTIFULLY WITH THAT FRESH LIGHT & BRIGHT APPEAL. . 6,000 SQ. FT - SITTING ON 1 ACRE LOT- 3 CAR DETACHED GAR. + A 912 SQ FT SHOP - 20X40 "RESORT LOOK" 20X40 IN GROUND POOL - GRAND ENTRANCE STEPS LEAD FROM THE FAMILY RM TO THE POOL AREA - LED LIGHTED BB COURT- DO I HEAR PICKEL BALL? BACK INSIDE- EXPECTATIONS HI - NO DISAPPOINTMENT

$519,900

5 beds3.5 baths6,000 sq ft

1136 W State St, Jacksonville, IL 62650

1 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
What a find in a great location! This charmer has been very well maintained. It's very cozy, comfortable and clean. Knotty Pine front foyer and sitting room, hardwood floors, large kitchen, good sized rooms and a nice floor plan. HVAC replaced in 2021.

$142,500

2 beds2 baths1,177 sq ft

121 City Pl, Jacksonville, IL 62650

9,350 sq ft lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
MLS Listings for Sale in Winchester, IL
What an opportunity to own a ranch style home on the west end at this price! 3 bedrooms with HARDWOOD floors, FULL basement, 2 car garage, fireplace, 1.5 baths on the main floor and functioning 2nd full in the basement. Roof new approx 2012 and HVAC approx 2015. Cash and conventional buyers come take a look as this is selling AS IS. Don't miss your chance to build some sweat equity!

$159,900

3 beds2.5 baths1,408 sq ft

12 Newland Ln, Jacksonville, IL 62650

9,450 sq ft lot • 2 garage spots • Car-dependent

Property at 1305 W Lafayette Ave, Jacksonville, IL 62650, 3 beds, 2 baths

$119,000

3 beds2 baths1,910 sq ft

1305 W Lafayette Ave, 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

$75,000

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

$285,000

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 1503 Mound Ave, Jacksonville, IL 62650, 4 beds, 3 baths

$320,000

4 beds3 baths2,594 sq ft

1503 Mound Ave, 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

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

$429,000

3 beds3 baths3,566 sq ft

806 Phillips Ferry Rd, Bluffs, IL 62621

Property at 414 Westgate Ave, Jacksonville, IL 62650, 3 beds, 2 baths

$199,000

3 beds2 baths1,738 sq ft

414 Westgate Ave, Jacksonville, IL 62650

Property at 8 Duncan Pl, Jacksonville, IL 62650, 3 beds, 2.5 baths

$239,900

3 beds2.5 baths2,888 sq ft

8 Duncan Pl, Jacksonville, IL 62650

Based on information submitted to the MLS GRID as of Thu Nov 13 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.

MLS Listings for Sale in Winchester

There are currently 5 mls listings for sale in Winchester at a median listing price of $82K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 29 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 3 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Winchester last month. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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62694 homes for sale

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