Real Estate Investment Properties for Sale in Chester, SC

Looking for investment property in Chester, SC with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
107 Hinton Street Chester, SC Step Back in Time in This Beautiful Victorian Home with A Lovely Wraparound Front Porch! P...	4 beds \| 3 baths \| 3,449 sq.ft.	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.19% Airbnb Rental Income: $null Traditional Rental Income: $2570 Airbnb ROI: N/A Traditional ROI: 8.19%
3116 Pilgrim Road Chester, SC Escape to your own peaceful retreat on almost 10 acres! This updated brick home has 3 bedr...	3 beds \| 2 baths \| 1,292 sq.ft.	$372,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $1635 Airbnb ROI: N/A Traditional ROI: 2.85%
569 Great Falls Highway Chester, SC	3 beds \| 2 baths \| 2,440 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 4.65%
530 Denton Avenue Chester, SC This adorable 3 bed 2 full bath single story on just over half an acre (with NO HOA!) is t...	3 beds \| 2 baths \| 1,191 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $1723 Airbnb ROI: N/A Traditional ROI: 5.33%
138 Pinckney Street Chester, SC 3 Bedroom 2 Bath Home in Move in Condition. Entering you will find Spacious open area for ...	3 beds \| 2 baths \| 1,466 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.74% Airbnb Rental Income: $null Traditional Rental Income: $1772 Airbnb ROI: N/A Traditional ROI: 7.74%
1239 Carlisle White Road Chester, SC Discover the perfect blend of peace, privacy, and convenience with this beautifully update...	2 beds \| 2 baths \| 1,497 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.81% Airbnb Rental Income: $null Traditional Rental Income: $1894 Airbnb ROI: N/A Traditional ROI: 4.81%
508 Old York Road Chester, SC Discover true Southern charm in this delightful two-bedroom, one bath home featuring a cla...	2 beds \| 1 baths \| 1,414 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $1514 Airbnb ROI: N/A Traditional ROI: 6.1%
823 Great Falls Highway Chester, SC Full of charm, this move in ready country-style home sits on over 2 acres and offers many ...	3 beds \| 1 baths \| 1,314 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.45% Airbnb Rental Income: $null Traditional Rental Income: $1515 Airbnb ROI: N/A Traditional ROI: 4.45%
1225 Liberty Road Chester, SC This thoughtfully remodeled farmhouse retreat combines modern updates with the charm of co...	2 beds \| 1 baths \| 1,132 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $1089 Airbnb ROI: N/A Traditional ROI: 1.09%
117 Hamilton Street Chester, SC Welcome to this 2023-built 3BR/2BA home offering 1,050 sq ft of modern living space! An op...	3 beds \| 2 baths \| 1,050 sq.ft.	$226,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.32% Airbnb Rental Income: $null Traditional Rental Income: $1788 Airbnb ROI: N/A Traditional ROI: 6.32%
103 Walker Street Chester, SC Perfect opportunity to own a turnkey rental property in a growing area! Beautifully renova...	2 beds \| 1 baths \| 1,028 sq.ft.	$172,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.09% Airbnb Rental Income: $null Traditional Rental Income: $1030 Airbnb ROI: N/A Traditional ROI: 4.09%
1178 Great Falls Highway Chester, SC Starting at $359,900, this custom-built 3-bedroom, 2 full bath home spans 1,563 square fee...	3 beds \| 2 baths \| 1,563 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $1934 Airbnb ROI: N/A Traditional ROI: 4.4%
536 Fourth Street unit: 9 #9 Chester, SC Seller is offering $5000 towards closing costs/buy down points. Almost new two bedroom, tw...	2 beds \| 2 baths \| 1,176 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.06% Airbnb Rental Income: $null Traditional Rental Income: $1612 Airbnb ROI: N/A Traditional ROI: 7.06%
510 Jones Street unit: 6 #6 Chester, SC Proposed New Construction in Chester! This proposed to-be-built 3-bedroom, 2-bath ranch-st...	3 beds \| 2 baths \| 1,200 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.06% Airbnb Rental Income: $null Traditional Rental Income: $1670 Airbnb ROI: N/A Traditional ROI: 6.06%
552 6th Street Chester, SC Tenant occupied. Do not disturb tenants. This newly remodeled home features new luxury vin...	2 beds \| 1 baths \| 840 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $1256 Airbnb ROI: N/A Traditional ROI: 6.68%
533 3rd Street Chester, SC Welcome to 533 3rd Street in Chester, SC! This fully remodeled 3-bedroom, 2-bathroom home ...	3 beds \| 2 baths \| 1,140 sq.ft.	$194,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.84% Airbnb Rental Income: $null Traditional Rental Income: $1599 Airbnb ROI: N/A Traditional ROI: 6.84%
572 2nd Street Chester, SC Charming Newly Remodeled Home on a Spacious Corner Lot Welcome to 572 Second St, a beautif...	2 beds \| 1 baths \| 1,183 sq.ft.	$122,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.86% Airbnb Rental Income: $null Traditional Rental Income: $1464 Airbnb ROI: N/A Traditional ROI: 9.86%
528 6th Street Chester, SC ******OPEN HOUSE SAT SEPT 13TH NOON TO 3PM. ENTER DRAWING FOR A $100 VISA GIFT CARD!**...	2 beds \| 2 baths \| 1,025 sq.ft.	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.2% Airbnb Rental Income: $null Traditional Rental Income: $1496 Airbnb ROI: N/A Traditional ROI: 6.2%
324 Ashford Street Chester, SC BACK ON THE MARKET! BUYER FELL OUT LAST MINUTE! Come see this charming ranch style home in...	3 beds \| 2 baths \| 1,204 sq.ft.	$229,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $1682 Airbnb ROI: N/A Traditional ROI: 5.74%
146 Saluda Street Chester, SC Back on market at no fault of the seller. This breathtaking, all brick, 4BR/2.5 Bath home ...	4 beds \| 3 baths \| 2,388 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.06% Airbnb Rental Income: $null Traditional Rental Income: $2802 Airbnb ROI: N/A Traditional ROI: 8.06%
113 Saluda Street Chester, SC Newly remodeled duplex is ready for you to occupy or rent! Each unit has 2 bedrooms, 1 bat...	4 beds \| 2 baths \| 1,778 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.31% Airbnb Rental Income: $null Traditional Rental Income: $1992 Airbnb ROI: N/A Traditional ROI: 6.31%
132 Loomis Street Chester, SC Motivated Seller! Affordable 2-Bedroom Home - Ideal for First-Time Buyers or Investors Don...	2 beds \| 1 baths \| 608 sq.ft.	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 7% Airbnb Rental Income: $null Traditional Rental Income: $1204 Airbnb ROI: N/A Traditional ROI: 7%
999 Halseville Road Chester, SC Old farmhouse located on 12 acres, known as the Colvin-Fant-Durham Farm Complex in rural C...	3 beds \| 3 baths \| 3,600 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $2186 Airbnb ROI: N/A Traditional ROI: 1.97%
555 Pryor Street Chester, SC Newly Renovated & Move-In Ready! Welcome to this beautifully updated home featuring 10FT. ...	2 beds \| 2 baths \| 971 sq.ft.	$172,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $1409 Airbnb ROI: N/A Traditional ROI: 6.68%
556 Roundtree Circle Chester, SC New Paint and Flooring make this 3 Bedroom Brick Ranch shine. There is a new concrete driv...	3 beds \| 1 baths \| 1,025 sq.ft.	$187,400	Airbnb cash on cash: N/A Traditional cash on cash: 6.13% Airbnb Rental Income: $null Traditional Rental Income: $1425 Airbnb ROI: N/A Traditional ROI: 6.13%
1177 Craigbrow Circle Chester, SC Welcome to this charming 1963 retreat in a desired neighborhood! The property is spacious,...	3 beds \| 2 baths \| 1,356 sq.ft.	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $1732 Airbnb ROI: N/A Traditional ROI: 4.54%
814 Severance Drive Chester, SC This unique property is the one you have been waiting for. The home offers 4 bedroom and 3...	4 beds \| 3 baths \| 2,207 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.37% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 5.37%
1154 Stringfellow Road Chester, SC Charming Renovated 3-Bedroom Home on 1.8 Acres Discover comfort and charm in this beautifu...	3 beds \| 1 baths \| 1,025 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $1399 Airbnb ROI: N/A Traditional ROI: 4.21%
39 E White Street Chester, SC This home is priced like rent - but you get to own it!!! Beautifully renovated 2-bedroom, ...	2 beds \| 2 baths \| 1,244 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.63% Airbnb Rental Income: $null Traditional Rental Income: $1631 Airbnb ROI: N/A Traditional ROI: 7.63%
679 Fairforest Road Chester, SC Opportunity in the heart of Chester, S.C. This private 4.89-acre retreat offers the perfec...	5 beds \| 4 baths \| 2,322 sq.ft.	$419,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A Traditional ROI: 5.67%
515 Gage Street Chester, SC Discover this beautifully refreshed 2-bedroom, 1-bath residence, thoughtfully updated. Enj...	2 beds \| 1 baths \| 1,177 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.16% Airbnb Rental Income: $null Traditional Rental Income: $1420 Airbnb ROI: N/A Traditional ROI: 7.16%
114 Starnes Street Chester, SC PRICE REDUCTION AND MOTIVATED SELLER!! This stunning fully renovated residence is poised t...	3 beds \| 1 baths \| 800 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.35% Airbnb Rental Income: $null Traditional Rental Income: $1332 Airbnb ROI: N/A Traditional ROI: 7.35%
126 Sunset Drive Chester, SC You will find a beautiful full brick home with all the upgrades and features you could pos...	4 beds \| 2 baths \| 2,200 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2360 Airbnb ROI: N/A Traditional ROI: 4.33%
510 Gage Street unit: 2 Blk B #2 Blk B Chester, SC Charming 2-bedroom, 1-bath home with the benefit of low county taxes! The inviting living ...	2 beds \| 1 baths \| 1,051 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.99% Airbnb Rental Income: $null Traditional Rental Income: $1393 Airbnb ROI: N/A Traditional ROI: 6.99%
976 Peden Bridge Road Chester, SC Welcome to this charming 1950s country rambler, thoughtfully renovated and remodeled. This...	3 beds \| 2 baths \| 1,844 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2152 Airbnb ROI: N/A Traditional ROI: 5.01%
912 Redwood Lane Chester, SC This home showcases a timeless brick exterior that is stately and low-maintenance, the sol...	3 beds \| 2 baths \| 1,858 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.05% Airbnb Rental Income: $null Traditional Rental Income: $2115 Airbnb ROI: N/A Traditional ROI: 4.05%
713 Meadowbrook Road Chester, SC The cutest home in need of a makeover! Wonderful opportunities for a remodel. Home has a s...	3 beds \| 2 baths \| 1,325 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.89% Airbnb Rental Income: $null Traditional Rental Income: $1719 Airbnb ROI: N/A Traditional ROI: 7.89%
115 W Lacy Street Chester, SC ELIGIBLE FOR 100% FINANCING! Ask how! 5 Bedroom, 3 bath, fully renovated in 2023, just...	5 beds \| 3 baths \| 2,724 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.04% Airbnb Rental Income: $null Traditional Rental Income: $2853 Airbnb ROI: N/A Traditional ROI: 8.04%
531 Ashford Road Chester, SC NEW CONSTRUCTION home on 3+/- Acres in Chester County, SC! Beautiful home with 3-bedrooms,...	3 beds \| 3 baths \| 1,909 sq.ft.	$459,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $2231 Airbnb ROI: N/A Traditional ROI: 3.95%
2843 Lakeshore Drive Chester, SC Welcome to the Cherry Hills subdivision! This 4-bedroom, 2.5-bath home at 2843 Lakeshore D...	4 beds \| 3 baths \| 2,660 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $2516 Airbnb ROI: N/A Traditional ROI: 1.71%

Real Estate investment in Chester, SC

There are 59 properties for sale in the city of Chester . The median list price in Chester is $237,000 and the average price per square foot is $148. In October 2025, the average monthly cash on cash return in Chester is 6.00%. The average monthly rental income in Chester is $1,737.

Chester, SC Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 59 investment properties available for sale in Chester.

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

Your search for investment property begins and ends here

Investment Property for Sale in Chester, SC

107 Hinton Street

Chester, SC

4 beds | 3 baths | 3,449 sq.ft.

$269,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2570

Airbnb ROI: N/A

Traditional ROI: 8.19%

3116 Pilgrim Road

Chester, SC

3 beds | 2 baths | 1,292 sq.ft.

$372,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.85%

Airbnb Rental Income: $null

Traditional Rental Income: $1635

Airbnb ROI: N/A

Traditional ROI: 2.85%

569 Great Falls Highway

Chester, SC

3 beds | 2 baths | 2,440 sq.ft.

$374,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2281

Airbnb ROI: N/A

Traditional ROI: 4.65%

530 Denton Avenue

Chester, SC

3 beds | 2 baths | 1,191 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $1723

Airbnb ROI: N/A

Traditional ROI: 5.33%

138 Pinckney Street

Chester, SC

3 beds | 2 baths | 1,466 sq.ft.

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.74%

Airbnb Rental Income: $null

Traditional Rental Income: $1772

Airbnb ROI: N/A

Traditional ROI: 7.74%

1239 Carlisle White Road

Chester, SC

2 beds | 2 baths | 1,497 sq.ft.

$299,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.81%

Airbnb Rental Income: $null

Traditional Rental Income: $1894

Airbnb ROI: N/A

Traditional ROI: 4.81%

508 Old York Road

Chester, SC

2 beds | 1 baths | 1,414 sq.ft.

$195,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.1%

Airbnb Rental Income: $null

Traditional Rental Income: $1514

Airbnb ROI: N/A

Traditional ROI: 6.1%

823 Great Falls Highway

Chester, SC

3 beds | 1 baths | 1,314 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.45%

Airbnb Rental Income: $null

Traditional Rental Income: $1515

Airbnb ROI: N/A