Real Estate Investments for Sale in Winchester, IN With High ROI

Are you looking for a vacation rental in Winchester, IN? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

Explore a variety of short-term homes & houses in Winchester, IN. Invest wisely with VRBO & Winchester, IN 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, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
635 E 225 N Winchester, IN Take a look at this beautiful 3 bedroom 2 bathroom home!! This home has been recently remo...	3 beds \| 2 baths \| 2,027 sq.ft.	$354,900	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.21% Airbnb Rental Income: $3305 Traditional Rental Income: $1925 Airbnb ROI: 6.13% Traditional ROI: 4.21%
942 E Short Street Winchester, IN Check out this charming 2 bed, 1 bath home in Winchester! This home has baseboard heating,...	2 beds \| 1 baths \| 1,006 sq.ft.	$134,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 9.47% Airbnb Rental Income: $1597 Traditional Rental Income: $1529 Airbnb ROI: 6.48% Traditional ROI: 9.47%
411 Westwood Drive Winchester, IN Welcome to your dream home in Winchester! This spacious 2 bedroom, 2 bathroom gem sits pro...	2 beds \| 2 baths \| 1,486 sq.ft.	$199,900	Airbnb cash on cash: 4.11% Traditional cash on cash: 7.08% Airbnb Rental Income: $1597 Traditional Rental Income: $1706 Airbnb ROI: 4.11% Traditional ROI: 7.08%
Investment Properties for Sale in Other Cities of Indiana
2473 Renck Court Lawrenceburg , IN Private Wooded Home nestled on a Cul de sac! This 3/4 Bed & 4 bath home offers over 2800 s...	3 beds \| 4 baths \| 2,748 sq.ft.	$399,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.51% Airbnb Rental Income: $1806 Traditional Rental Income: $2357 Airbnb ROI: 1.73% Traditional ROI: 4.51%
5934 Pine Bluff Drive Avon , IN This home features a grand open layout on the main floor, with a spacious great room seaml...	4 beds \| 3 baths \| 3,989 sq.ft.	$425,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.64% Airbnb Rental Income: $2448 Traditional Rental Income: $2673 Airbnb ROI: 2.57% Traditional ROI: 4.64%
9276 E Parke Place Rockville , IN Turn-Key 4 Bedroom, 2 Full Bath, Walk-out Basement, Amish Built, locally harvested Timber ...	4 beds \| 2 baths \| 2,408 sq.ft.	$480,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.78% Airbnb Rental Income: $null Traditional Rental Income: $2391 Airbnb ROI: N/A Traditional ROI: 3.78%
5625 Gateway E Drive Whitestown , IN Highly Desirable Ranch Home in Clark Meadows at Anson This move-in ready, single-level ra...	3 beds \| 3 baths \| 2,336 sq.ft.	$405,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 2.89% Airbnb Rental Income: $2808 Traditional Rental Income: $1956 Airbnb ROI: 3.41% Traditional ROI: 2.89%
13310 Ravenswood Boulevard Fort Wayne , IN This stunning home is ready for its new owner. Featuring the primary suite on the main flo...	4 beds \| 3 baths \| 2,413 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.23% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 5.23%
3442 N Valleyview Drive Bloomington , IN This property has been a great investment property for years, but could be investment or o...	3 beds \| 2 baths \| 884 sq.ft.	$250,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 2.76% Airbnb Rental Income: $1756 Traditional Rental Income: $1329 Airbnb ROI: 2.53% Traditional ROI: 2.76%
3377 S Crafters Court Bloomington , IN This beautiful four-bedroom, three-bathroom ranch-style home features a finished basement ...	4 beds \| 3 baths \| 3,256 sq.ft.	$437,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 4.55% Airbnb Rental Income: $3214 Traditional Rental Income: $2751 Airbnb ROI: 3.91% Traditional ROI: 4.55%
708 S Main Street Kendallville , IN Immediate possession! Check out this 2-story home in town with 5 bedrooms and 2 full baths...	5 beds \| 2 baths \| 2,273 sq.ft.	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.64% Airbnb Rental Income: $null Traditional Rental Income: $1704 Airbnb ROI: N/A Traditional ROI: 5.64%
7 Ashwood Circle Brownsburg , IN Wow! Move-in Ready Ranch in Beautiful Ashwood! Award Winning Brownsburg Schools! Newer HVA...	3 beds \| 2 baths \| 1,024 sq.ft.	$250,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 4.5% Airbnb Rental Income: $2858 Traditional Rental Income: $1478 Airbnb ROI: 7.53% Traditional ROI: 4.5%
1010 Rotherham Lane Beech Grove , IN Move in ready one level home in ESTABLISHED neighborhood. Home offers HUGE entry with vaul...	3 beds \| 2 baths \| 1,397 sq.ft.	$249,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 5.74% Airbnb Rental Income: $2546 Traditional Rental Income: $1826 Airbnb ROI: 6.2% Traditional ROI: 5.74%
2 W Old Ridge Road Hobart , IN FOR THE GARAGE ENTHUSIAST! 3 plus car garage with heat and air 200 amp air compressor, ki...	2 beds \| 2 baths \| 1,116 sq.ft.	$215,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 4.07% Airbnb Rental Income: $1886 Traditional Rental Income: $1284 Airbnb ROI: 4.56% Traditional ROI: 4.07%
1205 Meadow Lark Boulevard Warsaw , IN Many updates in this 3 bedroom, 1.5 bath home in Melody Acres. Over 1700 square feet all ...	3 beds \| 2 baths \| 1,720 sq.ft.	$245,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 7.64% Airbnb Rental Income: $2515 Traditional Rental Income: $2206 Airbnb ROI: 6.35% Traditional ROI: 7.64%
1011 N Noble Street Greenfield , IN Space abounds in this 2,000 square foot, 4 bedroom ranch in Greenfield! Explore this home ...	4 beds \| 2 baths \| 2,069 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.75% Airbnb Rental Income: $null Traditional Rental Income: $2372 Airbnb ROI: N/A Traditional ROI: 7.75%
1607 S Willow Bend Drive La Porte , IN Nestled in one of the most sought-after neighborhoods in LaPorte, this newly remodeled hom...	4 beds \| 3 baths \| 2,518 sq.ft.	$469,900	Airbnb cash on cash: 8.29% Traditional cash on cash: 5.06% Airbnb Rental Income: $5577 Traditional Rental Income: $3039 Airbnb ROI: 8.29% Traditional ROI: 5.06%

Real Estate investment in Winchester, IN

There are 3 properties for sale in the city of Winchester . The median list price in Winchester is $162,450 and the average price per square foot is $108. In October 2024, the average monthly cash on cash return in Winchester is 9.00%. The average monthly rental income in Winchester is $1,836.

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

There are 3 investment properties available for sale in Winchester.

In 2024, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $1,836.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, IN

635 E 225 N

Winchester, IN

3 beds | 2 baths | 2,027 sq.ft.

$354,900

Airbnb cash on cash: 6.13%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3305

Traditional Rental Income: $1925

Airbnb ROI: 6.13%

Traditional ROI: 4.21%

942 E Short Street

Winchester, IN

2 beds | 1 baths | 1,006 sq.ft.

$134,900

Airbnb cash on cash: 6.48%

Traditional cash on cash: 9.47%

Airbnb Rental Income: $1597

Traditional Rental Income: $1529

Airbnb ROI: 6.48%

Traditional ROI: 9.47%

411 Westwood Drive

Winchester, IN

2 beds | 2 baths | 1,486 sq.ft.

$199,900

Airbnb cash on cash: 4.11%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1597

Traditional Rental Income: $1706

Airbnb ROI: 4.11%

Traditional ROI: 7.08%

Investment Properties for Sale in Other Cities of Indiana

Lawrenceburg , IN

3 beds | 4 baths | 2,748 sq.ft.

$399,900

Airbnb cash on cash: 1.73%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1806

Traditional Rental Income: $2357

Airbnb ROI: 1.73%

Traditional ROI: 4.51%

Avon , IN

4 beds | 3 baths | 3,989 sq.ft.

$425,000

Airbnb cash on cash: 2.57%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2448

Traditional Rental Income: $2673

Airbnb ROI: 2.57%

Traditional ROI: 4.64%

Rockville , IN

4 beds | 2 baths | 2,408 sq.ft.

$480,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2391

Airbnb ROI: N/A

Traditional ROI: 3.78%

Whitestown , IN

3 beds | 3 baths | 2,336 sq.ft.

$405,000

Airbnb cash on cash: 3.41%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $2808

Traditional Rental Income: $1956

Airbnb ROI: 3.41%

Traditional ROI: 2.89%

Fort Wayne , IN

4 beds | 3 baths | 2,413 sq.ft.

$369,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.23%

Airbnb Rental Income: $null

Traditional Rental Income: $2555

Airbnb ROI: N/A

Traditional ROI: 5.23%

Bloomington , IN

3 beds | 2 baths | 884 sq.ft.

$250,000