View 985 S Simpson Drive Winchester, IN MLS# 202613679
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1 of 28
$3,100,000
4.0

Baths

4,500

Sq.Ft.

985 S Simpson Drive

Winchester, IN

View 4990 W 400 N Winchester, IN MLS# 202613330
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1 of 8
$49,900
3

Beds

2.0

Baths

1,344

Sq.Ft.

4990 W 400 N

Winchester, IN

View 516 N Union Street Winchester, IN MLS# 202613411
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1 of 24
$124,900
2

Beds

1.0

Baths

1,049

Sq.Ft.

516 N Union Street

Winchester, IN

The time to sell is now! THE TIME TO SELL IS NOW!
View 242 SE Greenville Avenue Winchester, IN MLS# 202613173
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1 of 35
$199,900
2

Beds

1.1

Baths

1,733

Sq.Ft.

242 SE Greenville Avenue

Winchester, IN

View 603 N Residence Street Winchester, IN MLS# 202613044
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1 of 24
$144,900
3

Beds

1.0

Baths

1,300

Sq.Ft.

603 N Residence Street

Winchester, IN

View 124 Sunset Drive Winchester, IN MLS# 202612418
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1 of 25
$194,900
2

Beds

2.0

Baths

1,220

Sq.Ft.

124 Sunset Drive

Winchester, IN

View 544 N Meridian Street Winchester, IN MLS# 202611172
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1 of 18
$119,900
2

Beds

1.0

Baths

916

Sq.Ft.

544 N Meridian Street

Winchester, IN

View 985 E Washington Street Winchester, IN MLS# 202610569
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1 of 15
$179,900
2

Beds

1.1

Baths

1,541

Sq.Ft.

985 E Washington Street

Winchester, IN

View 215 Best Avenue Winchester, IN MLS# 202610897
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1 of 19
$79,900
3

Beds

2.0

Baths

1,280

Sq.Ft.

215 Best Avenue

Winchester, IN

View 806 S Elm Boulevard Winchester, IN MLS# 202610302
$169,900
3

Beds

2.0

Baths

1,040

Sq.Ft.

806 S Elm Boulevard

Winchester, IN

View 19 Deer Cross Drive Winchester, IN MLS# 202610250
$264,900
2

Beds

2.0

Baths

1,423

Sq.Ft.

19 Deer Cross Drive

Winchester, IN

View 404 E Thompson Street Winchester, IN MLS# 202609024
$189,000
3

Beds

2.0

Baths

1,115

Sq.Ft.

404 E Thompson Street

Winchester, IN

View 1027 S Huntsville Road Winchester, IN MLS# 202608323
$579,900
3

Beds

2.0

Baths

1,575

Sq.Ft.

1027 S Huntsville Road

Winchester, IN

View 5056 W 150 S Winchester, IN MLS# 202608314
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1 of 31
$224,900
3

Beds

2.0

Baths

1,288

Sq.Ft.

5056 W 150 S

Winchester, IN

View 401 George Street Winchester, IN MLS# 202607913
$69,900
2

Beds

1.0

Baths

681

Sq.Ft.

401 George Street

Winchester, IN

View 2620 N 350 E Winchester, IN MLS# 202606955
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1 of 4
$1
Studio

Beds

0.0

Baths

2620 N 350 E

Winchester, IN

View 889 S Huntsville Road Winchester, IN MLS# 202605086
$327,900
3

Beds

2.1

Baths

2,096

Sq.Ft.

889 S Huntsville Road

Winchester, IN

View 4 Crestwood Drive Winchester, IN MLS# 202604949
$224,900
2

Beds

2.0

Baths

1,676

Sq.Ft.

4 Crestwood Drive

Winchester, IN

View 407 Westwood Drive Winchester, IN MLS# 202604116
$134,900
2

Beds

1.0

Baths

806

Sq.Ft.

407 Westwood Drive

Winchester, IN

View 395 Symmes Center Drive Winchester, IN MLS# 202548801
$349,900
1.0

Baths

900

Sq.Ft.

395 Symmes Center Drive

Winchester, IN

About Winchester

Listings in Winchester, IN

38

Estimated median home price

$184,450
Winchester IN Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Indiana real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, IN.

Homes for Sale by Price in Winchester, IN

PriceCount
$0 - 100K8
$100K - 200K16
$200K - 300K6
$300K - 400K5
$400K - 500K0
$500K - 600K1
$600K - 700K0
$700K - 800K0
$800K - 900K0
$900K - 1M1
$1M - Max1

Homes for Sale by Type in Winchester, IN

Property TypeCount
Single Family26
Townhouse0
Condo2
Commercial3
Rental5
Lots and Land7
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/18/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Indiana Regional Multiple Listing Service. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 4/18/2026.