Real Estate Investment Properties for Sale in Winchester, OH

Looking for investment property in Winchester, OH with high ROI ?

Explore a variety of short-term homes & houses in Winchester, OH. Invest wisely with VRBO & Winchester, OH Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Winchester, OH

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
49 W Sycamore St Winchester, OH R5 - WINCHESTER - 2 parcels totaling 0.8182 acre with a vinyl sided frame home featuring 1...	2 beds \| 1 baths \| 1,374 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.14% Airbnb Rental Income: $null Traditional Rental Income: $1623 Airbnb ROI: N/A Traditional ROI: 8.14%
455 Tom Brown Rd Winchester, OH Nestled in a country setting on Tom Brown Road this brick home offers over 1900 square fee...	3 beds \| 2 baths \| 1,938 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $2239 Airbnb ROI: N/A Traditional ROI: 4.13%
1300 Tri County Rd Winchester, OH Move right into this beautifully updated 3-bedroom, 2-bath brick ranch situated on just ov...	3 beds \| 2 baths \| 1,309 sq.ft.	$264,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $1688 Airbnb ROI: N/A Traditional ROI: 3.84%
44 Rhonda Ln Winchester, OH	3 beds \| 2 baths \| 1,188 sq.ft.	$236,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $1815 Airbnb ROI: N/A Traditional ROI: 5.86%
77 Wildcat Rd Winchester, OH 77 Wildcat Rd, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.91% Airbnb Rental Income: $null Traditional Rental Income: $926 Airbnb ROI: N/A Traditional ROI: -0.91%
6995 Bethlehem Rd Winchester, OH 6995 Bethlehem Rd, Winchester, OH 45697 \| Single Family Residential	3 beds \| 2 baths \| 1,893 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.87% Airbnb Rental Income: $null Traditional Rental Income: $2216 Airbnb ROI: N/A Traditional ROI: 9.87%
371 Silver Ln Winchester, OH Brand New Amish-Built Home on 1.5 Acres! Experience quality craftsmanship and country char...	3 beds \| 2 baths \| N/A	$252,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $2164 Airbnb ROI: N/A Traditional ROI: 6.16%
6939 Eckmansville Rd Winchester, OH 6939 Eckmansville Rd, Winchester, OH 45697 \| Manufactured Home	3 beds \| 1 baths \| 1,056 sq.ft.	$144,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.86% Airbnb Rental Income: $null Traditional Rental Income: $1535 Airbnb ROI: N/A Traditional ROI: 7.86%
880 St Rt 137 Winchester, OH Very well-maintained 3-bedroom, 2-bath home situated on approximately 1.6 acres in the Nor...	3 beds \| 2 baths \| 1,680 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.34% Airbnb Rental Income: $null Traditional Rental Income: $2189 Airbnb ROI: N/A Traditional ROI: 6.34%
10133 Tri County Rd Winchester, OH 10133 Tri County Rd, Winchester, OH 45697 \| Single Family Residential	2 beds \| 2 baths \| 952 sq.ft.	$149,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.61% Airbnb Rental Income: $null Traditional Rental Income: $1543 Airbnb ROI: N/A Traditional ROI: 7.61%
0 Fenton Rd Winchester, OH 0 Fenton Rd, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $961 Airbnb ROI: N/A Traditional ROI: 5.29%
0 Tom Brown Rd Winchester, OH 0 Tom Brown Rd, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$65,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.1% Airbnb Rental Income: $null Traditional Rental Income: $975 Airbnb ROI: N/A Traditional ROI: 11.1%
0 St Rt 247 Winchester, OH 0 247, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$307,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $975 Airbnb ROI: N/A Traditional ROI: 0.51%
0 John Woods Rd Winchester, OH 0 John Woods Rd, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$69,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.21% Airbnb Rental Income: $null Traditional Rental Income: $975 Airbnb ROI: N/A Traditional ROI: 10.21%
100 St Rt 137 Winchester, OH 100 State Route 137, Winchester, OH 45697 \| Single Family Residential	2 beds \| 2 baths \| 826 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $1864 Airbnb ROI: N/A Traditional ROI: 7.28%
139 West St Winchester, OH 139 West St, Winchester, OH 45697 \| Single Family Residential	5 beds \| 2 baths \| 2,720 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.24% Airbnb Rental Income: $null Traditional Rental Income: $2629 Airbnb ROI: N/A Traditional ROI: 8.24%
19804 St Rt 136 Winchester, OH 19804 St Rt 136, Winchester, OH 45697 \| Single Family Residential	4 beds \| 3 baths \| 6,300 sq.ft.	$1,090,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.33% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A Traditional ROI: 0.33%
320 Serendipity Ln Winchester, OH 320 Serendipity Ln, Winchester, OH 45697 \| Other	N/A beds \| N/A baths \| N/A	$89,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $1011 Airbnb ROI: N/A Traditional ROI: 7.92%
5203 Decatur Pike Winchester, OH 5203 Decatur Pike, Winchester, OH 45697 \| Single Family Residential	4 beds \| 2 baths \| 1,176 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $1927 Airbnb ROI: N/A Traditional ROI: 1.91%
70 Lark St Winchester, OH 70 Lark St, Winchester, OH 45697 \| Single Family Residential	3 beds \| 2 baths \| 1,400 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.61% Airbnb Rental Income: $null Traditional Rental Income: $2042 Airbnb ROI: N/A Traditional ROI: 6.61%
10174 Fincastle Winchester Rd Winchester, OH 10174 Fincastle Winchester Rd, Winchester, OH 45697 \| Single Family Residential	2 beds \| 1 baths \| 1,500 sq.ft.	$337,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $1568 Airbnb ROI: N/A Traditional ROI: 2.11%
17217 St Rt 136 Winchester, OH Sold before sent	2 beds \| 2 baths \| 9,747 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $2029 Airbnb ROI: N/A Traditional ROI: 3%
19166 State Route 136 Winchester, OH	3 beds \| 1 baths \| 1,047 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $1621 Airbnb ROI: N/A Traditional ROI: 6.9%
9832 Tri County Highway Winchester, OH Unique barndominium on 10 acres built for the homestead lifestyle you've been dreaming of....	3 beds \| 2 baths \| 1,848 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2463 Airbnb ROI: N/A Traditional ROI: 4.98%
14690 St Rt 136 Winchester, OH Tucked away in the quiet countryside of Cherry Fork, this brand new 2 bedroom, 1 bath home...	2 beds \| 1 baths \| N/A	$169,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.93% Airbnb Rental Income: $null Traditional Rental Income: $1618 Airbnb ROI: N/A Traditional ROI: 6.93%
373 Malibu Winchester, OH Turnkey.Furnished.Income-producing. Welcome to The White Pines, tiny home living at its fi...	2 beds \| 1 baths \| 560 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.5% Airbnb Rental Income: $null Traditional Rental Income: $1487 Airbnb ROI: N/A Traditional ROI: 7.5%
1090 Cherry Fork Road Winchester, OH Country Living Meets Modern Comfort on 10 Scenic Acres Escape to the peace and privacy of ...	3 beds \| 4 baths \| 2,650 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $3441 Airbnb ROI: N/A Traditional ROI: 6.18%
2047 Decatur Pike Winchester, OH Welcome to the peace and quiet of the countryside without giving up the comforts of home. ...	3 beds \| 2 baths \| 1,732 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.13% Airbnb Rental Income: $null Traditional Rental Income: $2253 Airbnb ROI: N/A Traditional ROI: 7.13%
2122 Tri County Road Winchester, OH Whether you're searching for your first home or looking to add to your investment portfoli...	3 beds \| 1 baths \| 960 sq.ft.	$119,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.2% Airbnb Rental Income: $null Traditional Rental Income: $1554 Airbnb ROI: N/A Traditional ROI: 10.2%
100 Maple Ave Winchester, OH Welcome home to this charming 2 bedroom, 1 bath residence nestled in a quiet neighborhood ...	2 beds \| 1 baths \| 1,596 sq.ft.	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.82% Airbnb Rental Income: $null Traditional Rental Income: $1727 Airbnb ROI: N/A Traditional ROI: 10.82%

Real Estate investment in Winchester, OH

There are 30 properties for sale in the city of Winchester . The median list price in Winchester is $106,936 and the average price per square foot is $49. In October 2026, the average monthly cash on cash return in Winchester is 7.00%. The average monthly rental income in Winchester is $1,744.

Winchester, OH Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 30 investment properties available for sale in Winchester.

In 2026, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, OH

49 W Sycamore St

Winchester, OH

2 beds | 1 baths | 1,374 sq.ft.

$149,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.14%

Airbnb Rental Income: $null

Traditional Rental Income: $1623

Airbnb ROI: N/A

Traditional ROI: 8.14%

455 Tom Brown Rd

Winchester, OH

3 beds | 2 baths | 1,938 sq.ft.

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2239

Airbnb ROI: N/A

Traditional ROI: 4.13%

1300 Tri County Rd

Winchester, OH

3 beds | 2 baths | 1,309 sq.ft.

$264,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $1688

Airbnb ROI: N/A

Traditional ROI: 3.84%

44 Rhonda Ln

Winchester, OH

3 beds | 2 baths | 1,188 sq.ft.

$236,500

Airbnb cash on cash: N/A

Traditional cash on cash: 5.86%

Airbnb Rental Income: $null

Traditional Rental Income: $1815

Airbnb ROI: N/A

Traditional ROI: 5.86%

77 Wildcat Rd

Winchester, OH

N/A beds | N/A baths | N/A

$545,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.91%

Airbnb Rental Income: $null

Traditional Rental Income: $926

Airbnb ROI: N/A

Traditional ROI: -0.91%

6995 Bethlehem Rd

Winchester, OH

3 beds | 2 baths | 1,893 sq.ft.

$179,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2216

Airbnb ROI: N/A

Traditional ROI: 9.87%

371 Silver Ln

Winchester, OH

3 beds | 2 baths | N/A

$252,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.16%

Airbnb Rental Income: $null

Traditional Rental Income: $2164

Airbnb ROI: N/A

Traditional ROI: 6.16%

6939 Eckmansville Rd

Winchester, OH

3 beds | 1 baths | 1,056 sq.ft.

$144,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.86%

Airbnb Rental Income: $null

Traditional Rental Income: $1535

Airbnb ROI: N/A