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.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $2275 Airbnb ROI: N/A Traditional ROI: 5.44%
5503 Sky Ridge Road Charlestown, IN Seller is offering $6,000 toward buyer's closing costs with an acceptable offer! Welcome t...	3 beds \| 3 baths \| 2,657 sq.ft.	$399,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 3.95% Airbnb Rental Income: $646 Traditional Rental Income: $2299 Airbnb ROI: -1.26% Traditional ROI: 3.95%
6303 Caleigh Drive Charlestown, IN Welcome home to this beautifully maintained 3 bedroom, 2 bath brick residence located in t...	3 beds \| 2 baths \| 1,471 sq.ft.	$281,400	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.95% Airbnb Rental Income: $646 Traditional Rental Income: $1645 Airbnb ROI: -0.94% Traditional ROI: 3.95%
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.	$275,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 4.49% Airbnb Rental Income: $646 Traditional Rental Income: $1669 Airbnb ROI: -0.6% Traditional ROI: 4.49%
6412 Night Sky Drive Charlestown, IN Come see this 3/2/2 home in Skyline Acres. The master bedroom can fit a king size bed, has...	3 beds \| 2 baths \| 1,436 sq.ft.	$334,900	Airbnb cash on cash: -1.17% Traditional cash on cash: 3.04% Airbnb Rental Income: $646 Traditional Rental Income: $1674 Airbnb ROI: -1.17% Traditional ROI: 3.04%
7808 Linwood Cir Charlestown, IN Welcome home to this beautifully maintained garden home designed for comfort, convenience,...	3 beds \| 2 baths \| 1,504 sq.ft.	$299,900	Airbnb cash on cash: -1.52% Traditional cash on cash: 3.49% Airbnb Rental Income: $646 Traditional Rental Income: $1765 Airbnb ROI: -1.52% Traditional ROI: 3.49%
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.	$774,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.32% Airbnb Rental Income: $null Traditional Rental Income: $3605 Airbnb ROI: N/A Traditional ROI: 3.32%
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: -0.57% Traditional cash on cash: 4.57% Airbnb Rental Income: $646 Traditional Rental Income: $1373 Airbnb ROI: -0.57% Traditional ROI: 4.57%
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: 4.94% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 4.94%
8526 Brock Road Charlestown, IN Take this opportunity to welcome your family home! Property features a beautifully maintai...	3 beds \| 3 baths \| 2,066 sq.ft.	$325,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.59% Airbnb Rental Income: $646 Traditional Rental Income: $1932 Airbnb ROI: -0.59% Traditional ROI: 4.59%
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: -1.54% Traditional cash on cash: 5.02% Airbnb Rental Income: $646 Traditional Rental Income: $1777 Airbnb ROI: -1.54% Traditional ROI: 5.02%
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.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $2202 Airbnb ROI: N/A Traditional ROI: 4.01%
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.	$749,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.17% Airbnb Rental Income: $646 Traditional Rental Income: $2410 Airbnb ROI: -0.78% Traditional ROI: 2.17%
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: -1.06% Traditional cash on cash: 7.07% Airbnb Rental Income: $646 Traditional Rental Income: $2736 Airbnb ROI: -1.06% Traditional ROI: 7.07%
6552 Ashley Springs Court Charlestown, IN One of the LARGEST LOTS in Ashley Springs! Tucked near the back of a quiet cul-de-sac on ....	4 beds \| 3 baths \| 2,255 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $2386 Airbnb ROI: N/A Traditional ROI: 3.71%
8002 Shady View Drive Charlestown, IN WELCOME HOME to resort-style living in one of Charlestown's most desirable neighborhoods. ...	4 beds \| 3 baths \| 3,412 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2640 Airbnb ROI: N/A Traditional ROI: 3.16%
3039 Hawks Landing Drive lot: 223 Charlestown, IN Open Sundays 2 to 4 p.m. Step into the Sterling II Plan, a beautifully crafted split-bedro...	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%
5022 - LOT 145 Hidden Springs Drive Charlestown, IN Premier Homes proudly presents the "Diamond" A floorplan - a thoughtfully designed 3-bedro...	3 beds \| 3 baths \| 1,667 sq.ft.	$259,900	Airbnb cash on cash: -0.89% Traditional cash on cash: 5.92% Airbnb Rental Income: $646 Traditional Rental Income: $2021 Airbnb ROI: -0.89% Traditional ROI: 5.92%
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: -1.19% Traditional cash on cash: 3.35% Airbnb Rental Income: $646 Traditional Rental Income: $2121 Airbnb ROI: -1.19% Traditional ROI: 3.35%
5203 N Hampton Court lot: #1513 Charlestown, IN Discover practical elegance in this corner townhome within the HAWTHORN GLEN COMMUNITY. Fe...	3 beds \| 3 baths \| 1,960 sq.ft.	$309,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 5.88% Airbnb Rental Income: $646 Traditional Rental Income: $2225 Airbnb ROI: -0.55% Traditional ROI: 5.88%
5205 N Hampton Court lot: #1514 Charlestown, IN SELF-GUIDED TOURS AVAILABLE ON-SITE! Discover practical elegance in this corner townhome w...	3 beds \| 3 baths \| 1,960 sq.ft.	$309,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 6.03% Airbnb Rental Income: $646 Traditional Rental Income: $2225 Airbnb ROI: -0.4% Traditional ROI: 6.03%
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.	$319,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 5.68% Airbnb Rental Income: $646 Traditional Rental Income: $2230 Airbnb ROI: -0.57% Traditional ROI: 5.68%
7994 Kismet Drive Charlestown, IN Get ready for an incredible property in a prime location of Charlestown, Indiana! This hom...	4 beds \| 3 baths \| 2,343 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $2428 Airbnb ROI: N/A Traditional ROI: 6.04%
6010 Heaven Hill Drive Charlestown, IN Welcome to this stunning Alliance Plan home, situated on a quiet cul-de-sac and over half ...	4 beds \| 3 baths \| 2,448 sq.ft.	$528,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $2526 Airbnb ROI: N/A Traditional ROI: 3.07%
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.	$378,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.95% Airbnb Rental Income: $null Traditional Rental Income: $2629 Airbnb ROI: N/A Traditional ROI: 5.95%
339 Bohart Lane Charlestown, IN This charming home offers 3 bedrooms and 1 full bathroom, featuring a spacious living room...	3 beds \| 1 baths \| 1,080 sq.ft.	$212,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.54% Airbnb Rental Income: $646 Traditional Rental Income: $1340 Airbnb ROI: -0.37% Traditional ROI: 4.54%
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.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 4.37%
4214 - LOT 218 Round Rock Boulevard Charlestown, IN Premier Homes presents The "Gem" floor plan is a 3 bed/2 bath, split bedroom, ranch-style ...	3 beds \| 2 baths \| 1,345 sq.ft.	$263,900	Airbnb cash on cash: -0.91% Traditional cash on cash: 4.73% Airbnb Rental Income: $646 Traditional Rental Income: $1752 Airbnb ROI: -0.91% Traditional ROI: 4.73%
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.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2409 Airbnb ROI: N/A Traditional ROI: 3.93%
5126 - LOT 136 Boulder Springs Boulevard Charlestown, IN Premier Homes presents the "Pearl" floor plan, a 1.5-story, 3 bed / 2.5 bath home that fea...	3 beds \| 3 baths \| 1,721 sq.ft.	$269,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.78% Airbnb Rental Income: $646 Traditional Rental Income: $2057 Airbnb ROI: -0.93% Traditional ROI: 5.78%
4210 - LOT 102 Round Rock Boulevard Charlestown, IN Premier Homes presents the ideal "Pearl" floor plan is a 1.5 story, 3 bed / 2.5 bath home ...	3 beds \| 3 baths \| 1,721 sq.ft.	$269,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.99% Airbnb Rental Income: $646 Traditional Rental Income: $2110 Airbnb ROI: -0.93% Traditional ROI: 5.99%
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: -1.08% Traditional cash on cash: 3.7% Airbnb Rental Income: $646 Traditional Rental Income: $1808 Airbnb ROI: -1.08% 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.	$375,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 4.13% Airbnb Rental Income: $646 Traditional Rental Income: $2216 Airbnb ROI: -1.18% Traditional ROI: 4.13%
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: -0.76% Traditional cash on cash: 3.72% Airbnb Rental Income: $646 Traditional Rental Income: $1862 Airbnb ROI: -0.76% Traditional ROI: 3.72%
7204 Stirling Drive #551 Charlestown, IN Builder is offering a $10,000 Buyer Incentive to use towards closing costs, interest rate ...	4 beds \| 3 baths \| 2,264 sq.ft.	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 3.1%
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: -1.28% Traditional cash on cash: 3.14% Airbnb Rental Income: $646 Traditional Rental Income: $2106 Airbnb ROI: -1.28% Traditional ROI: 3.14%
5501 Sky Ridge Road Charlestown, IN Here's a RARE opportunity to be one of only 6 homes in the neighborhood with EXCLUSIVE lak...	4 beds \| 3 baths \| 2,347 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $2258 Airbnb ROI: N/A Traditional ROI: 4.02%
7646 Melrose Lane #548 Charlestown, IN $10,000 BUYER INCENTIVE on this brand new home! You can use the $10,000 towards any allowa...	4 beds \| 3 baths \| 2,264 sq.ft.	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $2354 Airbnb ROI: N/A Traditional ROI: 3.09%
7306 Westhill Court lot: 494 Charlestown, IN BUILDER WILL PROVIDE UP TO $5,000 TOWARDS BUYERS CLOSING COST WITH PREFERRED LENDER ESTI...	4 beds \| 3 baths \| 2,530 sq.ft.	$494,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $2450 Airbnb ROI: N/A Traditional ROI: 3.25%
5014 Bolton Drive lot: 1616 Charlestown, IN Step into the Sterling II Plan, a beautifully crafted split-bedroom ranch that showcases e...	4 beds \| 3 baths \| 2,430 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2471 Airbnb ROI: N/A Traditional ROI: 3.93%

Real Estate investment in Charlestown, IN

There are 110 properties for sale in the city of Charlestown . The median list price in Charlestown is $399,450 and the average price per square foot is $168. In May 2026, the average monthly cash on cash return in Charlestown is 4.00%. The average monthly rental income in Charlestown is $2,202.

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

There are 110 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 $2,202.

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.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2275

Airbnb ROI: N/A

Traditional ROI: 5.44%

5503 Sky Ridge Road

Charlestown, IN

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

$399,000

Airbnb cash on cash: -1.26%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $646

Traditional Rental Income: $2299

Airbnb ROI: -1.26%

Traditional ROI: 3.95%

6303 Caleigh Drive

Charlestown, IN

3 beds | 2 baths | 1,471 sq.ft.

$281,400

Airbnb cash on cash: -0.94%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $646

Traditional Rental Income: $1645

Airbnb ROI: -0.94%

Traditional ROI: 3.95%

6414 Night Sky Drive

Charlestown, IN

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

$275,000

Airbnb cash on cash: -0.6%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $646

Traditional Rental Income: $1669

Airbnb ROI: -0.6%

Traditional ROI: 4.49%

6412 Night Sky Drive

Charlestown, IN

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

$334,900

Airbnb cash on cash: -1.17%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $646

Traditional Rental Income: $1674

Airbnb ROI: -1.17%

Traditional ROI: 3.04%

7808 Linwood Cir

Charlestown, IN

3 beds | 2 baths | 1,504 sq.ft.

$299,900

Airbnb cash on cash: -1.52%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $646

Traditional Rental Income: $1765

Airbnb ROI: -1.52%

Traditional ROI: 3.49%

5715 Ridgefield Drive

Charlestown, IN

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

$774,950

Airbnb cash on cash: N/A

Traditional cash on cash: 3.32%

Airbnb Rental Income: $null

Traditional Rental Income: $3605

Airbnb ROI: N/A

Traditional ROI: 3.32%

211 Talina Drive

Charlestown, IN

3 beds | 1 baths | 1,326 sq.ft.

$209,900

Airbnb cash on cash: -0.57%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $646

Traditional Rental Income: $1373

Airbnb ROI: -0.57%