Real Estate Investment Properties for Sale in Charlestown, IN

Looking for investment property in Charlestown, IN with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1802 Faith Avenue Charlestown, IN Welcome to the Cottage Homes at Southern Commons! Built in 2018, this spacious 4 BR, 2 1/2...	4 beds \| 3 baths \| 2,144 sq.ft.	$304,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.56% Airbnb Rental Income: $null Traditional Rental Income: $2275 Airbnb ROI: N/A Traditional ROI: 5.56%
5503 Sky Ridge Road Charlestown, IN Price Improvement! Offered well below county assessed value. Welcome to this beautifully m...	3 beds \| 3 baths \| 2,657 sq.ft.	$367,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 4.45% Airbnb Rental Income: $1630 Traditional Rental Income: $2299 Airbnb ROI: 1.17% Traditional ROI: 4.45%
8213 Salem Church Road Charlestown, IN APPROVED SHORT SALE - SOLD AS-IS Rustic Elegance Meets Modern Convenience in This Stunning...	4 beds \| 2 baths \| 3,032 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $2379 Airbnb ROI: N/A Traditional ROI: 4.86%
6414 Night Sky Drive Charlestown, IN Welcome to this beautifully maintained 3-bedroom, 2-bath brick ranch in Southern Indiana, ...	3 beds \| 2 baths \| 1,435 sq.ft.	$269,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 4.59% Airbnb Rental Income: $1630 Traditional Rental Income: $1669 Airbnb ROI: 2.63% Traditional ROI: 4.59%
6412 Night Sky Drive Charlestown, IN Well priced 3/2/2 home in Skyline Acres, listed below assessment! The master bedroom large...	3 beds \| 2 baths \| 1,436 sq.ft.	$319,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.23% Airbnb Rental Income: $1630 Traditional Rental Income: $1674 Airbnb ROI: 1.55% Traditional ROI: 3.23%
5715 Ridgefield Drive Charlestown, IN Welcome to your dream home! Once in a lifetime a property like this comes along! This exqu...	4 beds \| 4 baths \| 3,756 sq.ft.	$699,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.77% Airbnb Rental Income: $null Traditional Rental Income: $3605 Airbnb ROI: N/A Traditional ROI: 3.77%
122 Winthrop Avenue Charlestown, IN Beautiful 3 bedroom, 2.5 bath home located in a peaceful park-like setting in Charlestown ...	3 beds \| 3 baths \| 1,440 sq.ft.	$244,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 6.45% Airbnb Rental Income: $1630 Traditional Rental Income: $2021 Airbnb ROI: 2.77% Traditional ROI: 6.45%
7805 Linwood Circle Charlestown, IN Beautifully appointed 4-bedroom, 3 full-bath, 1.5-story patio home with an attached 2-car ...	4 beds \| 3 baths \| 1,926 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $2185 Airbnb ROI: N/A Traditional ROI: 4.47%
211 Talina Drive Charlestown, IN This charming 3-bedroom, 1-bathroom home in the heart of Charlestown offers incredible pot...	3 beds \| 1 baths \| 1,326 sq.ft.	$209,900	Airbnb cash on cash: 3.55% Traditional cash on cash: 4.57% Airbnb Rental Income: $1630 Traditional Rental Income: $1373 Airbnb ROI: 3.55% Traditional ROI: 4.57%
8828 Woodford Drive Charlestown, IN Welcome home to this move-in ready ranch in the highly desirable Woodford Farms! This beau...	3 beds \| 2 baths \| 1,257 sq.ft.	$264,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 4.22% Airbnb Rental Income: $1630 Traditional Rental Income: $1591 Airbnb ROI: 2.54% Traditional ROI: 4.22%
6607 Hibernia Road Charlestown, IN Welcome to your dream home in the peaceful community of Charlestown, Indiana! This beautif...	4 beds \| 2 baths \| 1,486 sq.ft.	$288,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 4.78%
6203 21st Century Drive Charlestown, IN This home received Multiple Offers. Welcome to this beautifully updated 5-bedroom, 3-bath ...	5 beds \| 3 baths \| 3,707 sq.ft.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $2588 Airbnb ROI: N/A Traditional ROI: 3.84%
710 Denham Lane Charlestown, IN Homes was completely renovated 4 years ago. Lower level walkout including third bedroom. S...	3 beds \| 2 baths \| 1,404 sq.ft.	$232,900	Airbnb cash on cash: 2.68% Traditional cash on cash: 1.63% Airbnb Rental Income: $1630 Traditional Rental Income: $939 Airbnb ROI: 2.68% Traditional ROI: 1.63%
118 Clark Road Charlestown, IN Our cozy cottage, The Emma, is located in the historic Pleasant Ridge welcomes you with th...	3 beds \| 2 baths \| 1,099 sq.ft.	$229,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.02% Airbnb Rental Income: $1630 Traditional Rental Income: $1777 Airbnb ROI: 2.23% Traditional ROI: 5.02%
8138 Farming Way Charlestown, IN Welcome to this beautifully designed home in the desirable Heritage Place subdivision in C...	3 beds \| 3 baths \| 2,040 sq.ft.	$389,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.64% Airbnb Rental Income: $1630 Traditional Rental Income: $2304 Airbnb ROI: 0.53% Traditional ROI: 3.64%
5211 N Hampton Court lot: #1517 Charlestown, IN OPEN SUN 2-4 PM! Discover practical elegance in this corner townhome within the HAWTHORN G...	3 beds \| 3 baths \| 1,960 sq.ft.	$299,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 6.2% Airbnb Rental Income: $1630 Traditional Rental Income: $2202 Airbnb ROI: 2.54% Traditional ROI: 6.2%
6254 Kamer Court Charlestown, IN Welcome to this beautifully maintained 4-bedroom, 3-bath home nestled in the heart of Hawt...	4 beds \| 3 baths \| 2,361 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $2255 Airbnb ROI: N/A Traditional ROI: 4.17%
6407 Sunset Loop Charlestown, IN WELCOME to this BEAUTIFUL 2 story home in the desirable ASHLEY SPRINGS SUBDIVISION! This 4...	4 beds \| 3 baths \| 2,268 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $2202 Airbnb ROI: N/A Traditional ROI: 4.28%
8303 Zachary Drive Charlestown, IN Welcome to this beautifully maintained ranch home in the desirable Woods of Tunnel Mill su...	4 beds \| 2 baths \| 2,213 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $1750 Airbnb ROI: N/A Traditional ROI: 3.05%
6309 Horizon Way Charlestown, IN Welcome home to this beautifully updated 3 bedroom, 2 bathroom all brick ranch! Offering 1...	3 beds \| 2 baths \| 1,363 sq.ft.	$275,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.64% Airbnb Rental Income: $1630 Traditional Rental Income: $1520 Airbnb ROI: 2.29% Traditional ROI: 3.64%
7136 Independence Way Charlestown, IN Welcome to 7136 Independence Way in Charlestown! This spacious and meticulously maintained...	5 beds \| 3 baths \| 3,493 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.96% Airbnb Rental Income: $null Traditional Rental Income: $2480 Airbnb ROI: N/A Traditional ROI: 2.96%
252 River Road W Charlestown, IN Wake up to the water in this beautifully positioned riverfront home in Charlestown! This 3...	3 beds \| 2 baths \| 2,268 sq.ft.	$699,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 2.39% Airbnb Rental Income: $1630 Traditional Rental Income: $2410 Airbnb ROI: 0.49% Traditional ROI: 2.39%
8426 Aberdeen Lane Charlestown, IN Welcome to this beautifully refreshed Cape Cod, offering classic charm, modern updates, an...	3 beds \| 4 baths \| 2,785 sq.ft.	$312,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 7.07% Airbnb Rental Income: $1630 Traditional Rental Income: $2736 Airbnb ROI: 1.73% Traditional ROI: 7.07%
8002 Shady View Drive Charlestown, IN WELCOME HOME to RESORT-STYLE LIVING in one of Charlestown's most sought-after neighborhood...	4 beds \| 3 baths \| 3,412 sq.ft.	$534,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.2% Airbnb Rental Income: $null Traditional Rental Income: $2640 Airbnb ROI: N/A Traditional ROI: 3.2%
3039 Hawks Landing Drive lot: 223 Charlestown, IN BUILD TO PROVIDE $10,000 TOWARDS CLOSING COSTS & PREPAIDS AT CLOSING! USDA ELIGIBLE* SELF-...	4 beds \| 3 baths \| 2,610 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $2511 Airbnb ROI: N/A Traditional ROI: 4.68%
6413 Sunset Loop Charlestown, IN Welcome home to this stunning all-brick ranch in the desirable Ashley Springs neighborhood...	3 beds \| 2 baths \| 1,665 sq.ft.	$289,900	Airbnb cash on cash: 1.93% Traditional cash on cash: 4.76% Airbnb Rental Income: $1630 Traditional Rental Income: $1940 Airbnb ROI: 1.93% Traditional ROI: 4.76%
8611 Burdette Drive Charlestown, IN Brick Home on a SPACIOUS lot! Welcoming living room anchored by a cozy fireplace, and an e...	3 beds \| 3 baths \| 2,800 sq.ft.	$325,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 6.02% Airbnb Rental Income: $1630 Traditional Rental Income: $2435 Airbnb ROI: 1.88% Traditional ROI: 6.02%
8124 Farming Way Charlestown, IN Come Tour The Manchester Plan at Heritage Place! This stunning 3 bedroom, 2 bathroom home ...	3 beds \| 2 baths \| 1,854 sq.ft.	$415,900	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.35% Airbnb Rental Income: $1630 Traditional Rental Income: $2121 Airbnb ROI: 0.91% Traditional ROI: 3.35%
5203 N Hampton Court lot: #1513 Charlestown, IN SELF-GUIDED TOURS AVAILABLE! Discover practical elegance in this corner townhome within th...	3 beds \| 3 baths \| 1,960 sq.ft.	$299,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 6.11% Airbnb Rental Income: $1630 Traditional Rental Income: $2225 Airbnb ROI: 2.37% Traditional ROI: 6.11%
5205 N Hampton Court lot: #1514 Charlestown, IN Discover practical elegance in this corner townhome within the HAWTHORN GLEN COMMUNITY. Fe...	3 beds \| 3 baths \| 1,960 sq.ft.	$299,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 6.26% Airbnb Rental Income: $1630 Traditional Rental Income: $2225 Airbnb ROI: 2.52% Traditional ROI: 6.26%
5207 N Hampton Court lot: #1515 Charlestown, IN SELF-GUIDED TOURS AVAILABLE ON-SITE.Discover practical elegance in this corner townhome wi...	3 beds \| 3 baths \| 1,960 sq.ft.	$309,900	Airbnb cash on cash: 2.26% Traditional cash on cash: 5.89% Airbnb Rental Income: $1630 Traditional Rental Income: $2230 Airbnb ROI: 2.26% Traditional ROI: 5.89%
5805 Ray's (6SV) Court Charlestown, IN New Construction! SYCAMORE VILLAGE is located off HWY 403 on Juniper Ridge Drive. The "Gen...	4 beds \| 4 baths \| 2,320 sq.ft.	$384,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.84% Airbnb Rental Income: $null Traditional Rental Income: $2629 Airbnb ROI: N/A Traditional ROI: 5.84%
8222 Crescent Cove Charlestown, IN Trendy new Jensen plan by Fischer Homes in beautiful Silvercreek Meadows, where limited ho...	4 beds \| 3 baths \| 2,790 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.76% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 4.76%
5021 Bolton Drive lot: 1601 Charlestown, IN BUILDER WILL PROVIDE UP TO $5,000 TOWARDS BUYERS CLOSING COST WITH PREFERRED LENDER Back...	4 beds \| 3 baths \| 2,280 sq.ft.	$392,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2409 Airbnb ROI: N/A Traditional ROI: 4.32%
5120 - LOT 122 Boulder Springs Boulevard Charlestown, IN Premier Homes presents the lovely "Gem" floor plan, a 3 bed/2 bath, split bedroom, ranch-s...	3 beds \| 2 baths \| 1,410 sq.ft.	$324,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.7% Airbnb Rental Income: $1630 Traditional Rental Income: $1808 Airbnb ROI: 1.61% Traditional ROI: 3.7%
8112 Harmony Way Charlestown, IN New construction by Fischer Homes in the beautiful Silvercreek Meadows community,, where l...	3 beds \| 3 baths \| 1,991 sq.ft.	$349,900	Airbnb cash on cash: 1.36% Traditional cash on cash: 4.55% Airbnb Rental Income: $1630 Traditional Rental Income: $2216 Airbnb ROI: 1.36% Traditional ROI: 4.55%
5411 Mansfield Way Charlestown, IN Donât miss this great ranch home located in the desirable Hawthorne Glen subdivision! Th...	3 beds \| 2 baths \| 1,633 sq.ft.	$359,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 3.72% Airbnb Rental Income: $1630 Traditional Rental Income: $1862 Airbnb ROI: 1.67% Traditional ROI: 3.72%
7204 Stirling Drive #551 Charlestown, IN The Valor floor plan by Schuler Homes has 4 BR, 3 FULL BA, and a 3 CAR GARAGE! Open floor ...	4 beds \| 3 baths \| 2,264 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 3.3%
6216 Pleasant Run #935 Charlestown, IN Introducing The Maddie - the newest floorplan from Land-Mill, where thoughtful design meet...	3 beds \| 2 baths \| 1,941 sq.ft.	$425,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.14% Airbnb Rental Income: $1630 Traditional Rental Income: $2106 Airbnb ROI: 0.78% Traditional ROI: 3.14%
7646 Melrose Lane #548 Charlestown, IN This home is Move-In Ready! Desirable Valor floor plan by Schuler Homes has 4 Bedrooms, 3 ...	4 beds \| 3 baths \| 2,264 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $2354 Airbnb ROI: N/A Traditional ROI: 3.41%

Real Estate investment in Charlestown, IN

There are 98 properties for sale in the city of Charlestown . The median list price in Charlestown is $229,862 and the average price per square foot is $94. In July 2026, the average monthly cash on cash return in Charlestown is 4.00%. The average monthly rental income in Charlestown is $2,221.

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

There are 98 investment properties available for sale in Charlestown.

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

The ROI for Long-Term is higher than the Short-Term in Charlestown with average rental income of $2,221.

Your search for investment property begins and ends here

Investment Property for Sale in Charlestown, IN

1802 Faith Avenue

Charlestown, IN

4 beds | 3 baths | 2,144 sq.ft.

$304,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2275

Airbnb ROI: N/A

Traditional ROI: 5.56%

5503 Sky Ridge Road

Charlestown, IN

3 beds | 3 baths | 2,657 sq.ft.

$367,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 4.45%

Airbnb Rental Income: $1630

Traditional Rental Income: $2299

Airbnb ROI: 1.17%

Traditional ROI: 4.45%

8213 Salem Church Road

Charlestown, IN

4 beds | 2 baths | 3,032 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2379

Airbnb ROI: N/A

Traditional ROI: 4.86%

6414 Night Sky Drive

Charlestown, IN

3 beds | 2 baths | 1,435 sq.ft.

$269,900

Airbnb cash on cash: 2.63%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $1630

Traditional Rental Income: $1669

Airbnb ROI: 2.63%

Traditional ROI: 4.59%

6412 Night Sky Drive

Charlestown, IN

3 beds | 2 baths | 1,436 sq.ft.

$319,900

Airbnb cash on cash: 1.55%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $1630

Traditional Rental Income: $1674

Airbnb ROI: 1.55%

Traditional ROI: 3.23%

5715 Ridgefield Drive

Charlestown, IN

4 beds | 4 baths | 3,756 sq.ft.

$699,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.77%

Airbnb Rental Income: $null

Traditional Rental Income: $3605

Airbnb ROI: N/A

Traditional ROI: 3.77%

122 Winthrop Avenue

Charlestown, IN

3 beds | 3 baths | 1,440 sq.ft.

$244,900

Airbnb cash on cash: 2.77%

Traditional cash on cash: 6.45%

Airbnb Rental Income: $1630

Traditional Rental Income: $2021

Airbnb ROI: 2.77%

Traditional ROI: 6.45%

7805 Linwood Circle

Charlestown, IN

4 beds | 3 baths | 1,926 sq.ft.

$345,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2185

Airbnb ROI: N/A