Winchester, IN homes for sale & real estate

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216 S West St, Winchester, IN 47394
216 S West St, Winchester, IN 47394
216 S West St, Winchester, IN 47394
ABOUT THIS HOME
Winchester, IN Homes for Sale
Welcome to this rejuvenated 2 bedroom, 1 bathroom home in Winchester! This property has been beautifully updated throughout featuring a new kitchen and bathroom, fresh luxury vinyl plank flooring and carpet, and a new central air unit and furnace for year round comfort. Outside, you’ll love the spacious fenced in yard and the attached 2 car garage that offers convenience and plenty of storage space. Don’t miss your chance to own this low maintenance turn key home in a great location!

$139,000

2 beds1 bath1,096 sq ft

216 S West St, Winchester, IN 47394

5,227 sq ft lot • Garage • Very walkable

4803 W 500 N, Winchester, IN 47394
4803 W 500 N, Winchester, IN 47394
4803 W 500 N, Winchester, IN 47394
ABOUT THIS HOME
Winchester, IN Homes for Sale
4803 West 500 North in Winchester, Indiana is a homesteader’s dream nestled on 6.7 scenic acres. This rural property blends comfort, practicality, and outdoor living, making it a perfect fit for those seeking country independence, investment opportunity, or a lifestyle rooted in agriculture and nature. It features a gorgeous 1.5-acre fully stocked pond, ideal for quiet evenings or fishing, paired with a covered shelter house for shaded relaxation and gatherings by the water. The land itself offers ample open, flat space for planting, raising livestock, or future expansion, with established flower beds and gardening plots already in place. Two private wells ensure reliable water access

$334,900

4 beds1 bath1,703 sq ft

4803 W 500 N, Winchester, IN 47394

6.7 acre lot • 2 garage spots • Car-dependent

418 N Main St, Winchester, IN 47394
418 N Main St, Winchester, IN 47394
418 N Main St, Winchester, IN 47394
ABOUT THIS HOME
Winchester, IN Homes for Sale
Welcome to 418 N Main Street! This charming 2-story home offers 3 bedrooms, 1 bathroom and 1,472 sq ft of comfortable living space. Enjoy the inviting covered front porch - perfect for relaxing evenings. Inside, you'll find recent upgrades including: new windows, a high-efficiency furnace, central air and newer appliances, ensuring comfort and energy savings. With spacious rooms and modern updates throughout, this home is move-in ready and priced to sell at $103,900.00!

$103,900

3 beds1 bath1,472 sq ft

418 N Main St, Winchester, IN 47394

6,970 sq ft lot • Somewhat walkable

1492 S Old Hwy 27, Winchester, IN 47394
1492 S Old Hwy 27, Winchester, IN 47394
1492 S Old Hwy 27, Winchester, IN 47394
ABOUT THIS HOME
Winchester, IN Homes for Sale
This 3-bedroom, 1.5-bath home features custom woodwork throughout and a beautifully crafted kitchen with red oak cabinets and custom barstools. Relax on the screened-in front porch or enjoy the meticulously landscaped yard. The large garden area has been enriched with compost for 48 years—ideal for any gardening enthusiast. Outside, you'll find a 25x19 enclosed carport and a 30x18 outbuilding currently leased as a one-bedroom apartment complete with a kitchen, living room, and full bath—offering immediate rental income

$224,900

3 beds1.5 baths1,392 sq ft

1492 S Old Hwy 27, Winchester, IN 47394

1.08 acre lot • 2 garage spots • Car-dependent

1446 Harbours Woodland Ct, Winchester, IN 47394
1446 Harbours Woodland Ct, Winchester, IN 47394
1446 Harbours Woodland Ct, Winchester, IN 47394
ABOUT THIS HOME
Winchester, IN Homes for Sale
Take a look at this beautiful home nestled in a serene neighborhood just outside of Winchester. The main floor features a spacious primary bedroom for added convenience, while two additional bedrooms upstairs provide plenty of room for family or guests. Outside, you’ll love the detached garage and barn—perfect for storage, hobbies, or extra space. Whether you're enjoying the peaceful surroundings or relaxing inside, this home offers the perfect blend of charm, comfort, and functionality.

$165,000

3 beds1 bath1,704 sq ft

1446 Harbours Woodland Ct, Winchester, IN 47394

9,583 sq ft lot • Garage • Car-dependent

Property at 170 Sunset Dr, Winchester, IN 47394, 2 beds, 2 baths

$184,900

2 beds2 baths1,220 sq ft

170 Sunset Dr, Winchester, IN 47394

Property at 176 Sunset Dr, Winchester, IN 47394, 2 beds, 2 baths

$194,900

2 beds2 baths1,220 sq ft

176 Sunset Dr, Winchester, IN 47394

Property at 544 N Main St, Winchester, IN 47394, 5 beds, 2 baths

$238,000

5 beds2 baths2,349 sq ft

544 N Main St, Winchester, IN 47394

Property at 619 Richmond St, Winchester, IN 47394, 4 beds, 1.5 baths

$149,900

4 beds1.5 baths1,520 sq ft

619 Richmond St, Winchester, IN 47394

Property at 300 S Evans St, IN 47382, 3 beds, 1 bath

$190,000

3 beds1 bath1,746 sq ft

300 S Evans St

$190,000

3 beds1 bath— sq ft

300 S Evans St, Saratoga, IN 47382

(937) 548-4663

Property at 1041 S Huntsville Rd, Winchester, IN 47394, 3 beds, 2.5 baths

$395,000

3 beds2.5 baths1,568 sq ft

1041 S Huntsville Rd, Winchester, IN 47394

Property at 619 Residence St, Winchester, IN 47394, 3 beds, 1 bath

$69,900

3 beds1 bath1,840 sq ft

619 Residence St, Winchester, IN 47394

Property at 627 S Main St, Winchester, IN 47394, 2 beds, 1 bath

$149,900

2 beds1 bath1,636 sq ft

627 S Main St, Winchester, IN 47394

Property at 1430 E Union City Pike, Winchester, IN 47394, 3 beds, 2 baths

$307,000

3 beds2 baths2,090 sq ft

1430 E Union City Pike, Winchester, IN 47394

(937) 548-5750

Property at 2105 N 100 W, Winchester, IN 47394, 4 beds, 2 baths

$399,900

4 beds2 baths1,344 sq ft

2105 N 100 W, Winchester, IN 47394

Property at 326 S Meridian St, Winchester, IN 47394, 2 beds, 2 baths

$149,000

2 beds2 baths1,764 sq ft

326 S Meridian St, Winchester, IN 47394

Property at 521 E Short St, Winchester, IN 47394, 4 beds, 2 baths

$179,900

4 beds2 baths1,507 sq ft

521 E Short St, Winchester, IN 47394

Property at 439 S Meridian St, Winchester, IN 47394, 3 beds, 2 baths

$89,900

3 beds2 baths2,256 sq ft

439 S Meridian St, Winchester, IN 47394

Property at 516 N Meridian St, Winchester, IN 47394, 4 beds, 1 bath

$87,000

4 beds1 bath1,886 sq ft

516 N Meridian St, Winchester, IN 47394

Property at 919 Waterview St, Winchester, IN 47394, 3 beds, 2.5 baths

$269,900

3 beds2.5 baths1,642 sq ft

919 Waterview St, Winchester, IN 47394

Property at 924 Waterview St, Winchester, IN 47394, 3 beds, 2.5 baths

$299,900

3 beds2.5 baths2,093 sq ft

924 Waterview St, Winchester, IN 47394

Property at Multiple Adresses, Winchester, IN 47394, 8 beds, 3 baths

$249,900

8 beds3 baths4,906 sq ft

Multiple Adresses, Winchester, IN 47394

Property at 803 S Beeson Dr, Winchester, IN 47394, 2 beds, 1 bath

$64,900

2 beds1 bath1,674 sq ft

803 S Beeson Dr, Winchester, IN 47394

Property at 220 N Main St, Winchester, IN 47394, 2 beds, 2.5 baths

$64,900

2 beds2.5 baths3,960 sq ft

220 N Main St, Winchester, IN 47394

Property at 78 S Amanda Dr, Winchester, IN 47394, 2 beds, 1 bath

$48,000

2 beds1 bath910 sq ft

78 S Amanda Dr, Winchester, IN 47394

Property at 418 N Union St, Winchester, IN 47394

$25,250

— beds— baths— sq ft

418 N Union St, Winchester, IN 47394

Property at 307 E Main St, Saratoga, IN 47382

$9,900

— beds— baths— sq ft

307 E Main St, Saratoga, IN 47382

Property at 1033 S Huntsville Rd, Winchester, IN 47394

$35,000

— beds— baths— sq ft

1033 S Huntsville Rd, Winchester, IN 47394

Property at TBD S 300 E, Winchester, IN 47394

$339,675

— beds— baths— sq ft

TBD S 300 E, Winchester, IN 47394

Property at TBD Symmes Center Dr. Lot #3, Winchester, IN 47394

$349,900

— beds— baths— sq ft

TBD Symmes Center Dr. Lot #3, Winchester, IN 47394

Property at Lot 5 Huntsville Rd, Winchester, IN 47394

$32,000

— beds— baths— sq ft

Lot 5 Huntsville Rd, Winchester, IN 47394

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Based on information submitted to the MLS GRID as of Thu Jul 31 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, IN

Cities

Zip Codes

47390 homes for sale
$174,000
47394 homes for sale
$184,900

Winchester, IN real estate trends

$74.2K

Sale price

-41.1%
since last year

$73

Sale $/sq ft

-30.3%
since last year

Under list price

6.9%

Days on market

6.5

Down payment

—

Total homes sold

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The information is being provided by Dayton Area Board of Realtors MLS. Information deemed reliable but not guaranteed. Information is provided for the consumer's personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2025 Dayton Area Board of Realtors MLS. All Rights Reserved.

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