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
2923 Old Greenville Highway Chester, SC New construction! This beautifully crafted Craftsman-style home is almost completed! Locat...	5 beds \| 3 baths \| N/A	$554,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $2532 Airbnb ROI: N/A Traditional ROI: 3.54%
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%
109 Shamrock Drive Chester, SC All brick three bedroom 2 bath home tucked away in Chester. Hardwood floors in dining room...	3 beds \| 2 baths \| 2,267 sq.ft.	$324,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $2137 Airbnb ROI: N/A Traditional ROI: 5.21%
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%
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%
108 Graham Street Chester, SC Spacious corner lot home that has been fully renovated down to the studs! Home is less tha...	2 beds \| 1 baths \| 1,014 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $1064 Airbnb ROI: N/A Traditional ROI: 4.13%
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%
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%
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%
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.	$409,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.23% Airbnb Rental Income: $null Traditional Rental Income: $2591 Airbnb ROI: N/A Traditional ROI: 5.23%
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.	$187,600	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $1425 Airbnb ROI: N/A Traditional ROI: 6.12%
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%
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.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.98% Airbnb Rental Income: $null Traditional Rental Income: $2570 Airbnb ROI: N/A Traditional ROI: 7.98%
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.	$374,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $1635 Airbnb ROI: N/A Traditional ROI: 2.83%
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%
2937 Lakeshore Drive unit: 45 #45 Chester, SC Welcome to Lakeshore Dr, located in the highly sought-after Cherry Hills Subdivision. This...	3 beds \| 2 baths \| 2,453 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $2214 Airbnb ROI: N/A Traditional ROI: 0.97%
518 W White Street Chester, SC Newly renovated home in move-in condition, perfect for a growing family. This home offers ...	3 beds \| 3 baths \| 1,013 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.15% Airbnb Rental Income: $null Traditional Rental Income: $1721 Airbnb ROI: N/A Traditional ROI: 10.15%
560 Roundtree Circle Chester, SC Fully renovated all-brick 3-bedroom, 1-bath home. Features include living room, dining are...	3 beds \| 1 baths \| 1,025 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.37% Airbnb Rental Income: $null Traditional Rental Income: $1398 Airbnb ROI: N/A Traditional ROI: 5.37%
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%
149 Wylie Street Chester, SC Charming Dollhouse-Inspired Starter Home for First-Time Buyer or Invester. Step into this ...	3 beds \| 1 baths \| 1,463 sq.ft.	$209,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $1432 Airbnb ROI: N/A Traditional ROI: 5.19%
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%
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%
823 Great Falls Highway Chester, SC Full of charm, this country-style home sits on over 2 acres and offers many recent improve...	3 beds \| 1 baths \| 1,314 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $1515 Airbnb ROI: N/A Traditional ROI: 4.02%
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%
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%
114 Starnes Street Chester, SC This stunning fully renovated residence is poised to welcome its new owner. The property b...	3 beds \| 1 baths \| 800 sq.ft.	$157,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.66% Airbnb Rental Income: $null Traditional Rental Income: $1332 Airbnb ROI: N/A Traditional ROI: 6.66%
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.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2360 Airbnb ROI: N/A Traditional ROI: 3.93%
912 Pineview Lakes Road Chester, SC This spacious 5-bedroom, 4-bath home offers over 4,000 sq ft of comfortable living space n...	5 beds \| 4 baths \| 4,003 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $3463 Airbnb ROI: N/A Traditional ROI: 5.25%
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.	$324,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $1894 Airbnb ROI: N/A Traditional ROI: 4.33%
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.	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.32% Airbnb Rental Income: $null Traditional Rental Income: $1772 Airbnb ROI: N/A Traditional ROI: 6.32%
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.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.75% Airbnb Rental Income: $null Traditional Rental Income: $1393 Airbnb ROI: N/A Traditional ROI: 6.75%
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%
823 Rabbit Run Chester, SC Welcome home! A charming, nestled home on a private lot of land surrounded by mature trees...	3 beds \| 2 baths \| 1,510 sq.ft.	$299,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $1888 Airbnb ROI: N/A Traditional ROI: 4.96%
535 5th Street Chester, SC Don't miss your chance to snag a home in the growing city of Chester for under $200K! ? Th...	3 beds \| 1 baths \| 1,299 sq.ft.	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.17% Airbnb Rental Income: $null Traditional Rental Income: $1540 Airbnb ROI: N/A Traditional ROI: 8.17%
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%
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%
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.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $2231 Airbnb ROI: N/A Traditional ROI: 3.85%
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.	$228,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.27% Airbnb Rental Income: $null Traditional Rental Income: $1788 Airbnb ROI: N/A Traditional ROI: 6.27%
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 49 properties for sale in the city of Chester . The median list price in Chester is $237,500 and the average price per square foot is $140. In September 2025, the average monthly cash on cash return in Chester is 6.00%. The average monthly rental income in Chester is $1,788.

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

There are 49 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

2923 Old Greenville Highway

Chester, SC

5 beds | 3 baths | N/A

$554,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.54%

Airbnb Rental Income: $null

Traditional Rental Income: $2532

Airbnb ROI: N/A

Traditional ROI: 3.54%

1178 Great Falls Highway

Chester, SC

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

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%

109 Shamrock Drive

Chester, SC

3 beds | 2 baths | 2,267 sq.ft.

$324,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2137

Airbnb ROI: N/A

Traditional ROI: 5.21%

510 Jones Street unit: 6 #6

Chester, SC

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%

324 Ashford Street

Chester, SC

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%

108 Graham Street

Chester, SC

2 beds | 1 baths | 1,014 sq.ft.

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.13%

Airbnb Rental Income: $null

Traditional Rental Income: $1064

Airbnb ROI: N/A

Traditional ROI: 4.13%

146 Saluda Street

Chester, SC

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