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 Luxury, location, and lifestyle converge in your stunning new home on 2923 Old Greenville ...	5 beds \| 3 baths \| 2,580 sq.ft.	$492,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $2532 Airbnb ROI: N/A Traditional ROI: 4.11%
107 Hinton Street Chester, SC Stunning 4-Bedroom Victorian Home in Historic Chester Welcome to 107 Hinton St-a beautiful...	4 beds \| 3 baths \| 3,449 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.92% Airbnb Rental Income: $null Traditional Rental Income: $2570 Airbnb ROI: N/A Traditional ROI: 8.92%
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 Welcome to this beautiful full-brick 3-bedroom, 2 full bath home, nestled on a generous 1....	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%
169 E Lacy Street Chester, SC 3 bedroom/2 bath home located near the heart of downtown Chester, just minutes from shoppi...	3 beds \| 2 baths \| 1,405 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $1827 Airbnb ROI: N/A Traditional ROI: 6.94%
530 Denton Avenue Chester, SC $2000 Seller Paid Closing Costs for the Buyer!! This adorable 3 bed 2 full bath sing...	3 beds \| 2 baths \| 1,191 sq.ft.	$248,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.39% Airbnb Rental Income: $null Traditional Rental Income: $1723 Airbnb ROI: N/A Traditional ROI: 5.39%
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.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $1894 Airbnb ROI: N/A Traditional ROI: 5.05%
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.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.51% Airbnb Rental Income: $null Traditional Rental Income: $1514 Airbnb ROI: N/A Traditional ROI: 6.51%
511 W Elliott Street Chester, SC 2 bedroom home on corner lot with fenced yard. Large eat in kitchen, living room with gas ...	2 beds \| 1 baths \| 1,026 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $1029 Airbnb ROI: N/A Traditional ROI: 4.96%
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%
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%
113 Brawley Street Chester, SC Welcome to 113 Brawley Street. Don't miss your chance to see this completely transformed 1...	3 beds \| 1 baths \| 1,738 sq.ft.	$220,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.56% Airbnb Rental Income: $null Traditional Rental Income: $1609 Airbnb ROI: N/A Traditional ROI: 5.56%
103 Walker Street Chester, SC Move in ready! Beautifully renovated 2 bedroom, 1 bath near the heart of Chester! Stainles...	2 beds \| 1 baths \| 1,028 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $1030 Airbnb ROI: N/A Traditional ROI: 4.16%
556 6th Street Chester, SC MOVE IN READY home with a large yard overlooking JA Cochran Bypass. New flooring and paint...	2 beds \| 1 baths \| 840 sq.ft.	$115,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.35% Airbnb Rental Income: $null Traditional Rental Income: $1196 Airbnb ROI: N/A Traditional ROI: 8.35%
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.	$119,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.09% Airbnb Rental Income: $null Traditional Rental Income: $1464 Airbnb ROI: N/A Traditional ROI: 10.09%
528 6th Street Chester, SC Seller is offering $5,000 toward closing costs or a rate buy-down with a competitive offer...	2 beds \| 2 baths \| 1,025 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.4% Airbnb Rental Income: $null Traditional Rental Income: $1496 Airbnb ROI: N/A Traditional ROI: 6.4%
324 Ashford Street Chester, SC Fall in love with this brand-new home at 324 Ashford Street - the perfect mix of modern st...	3 beds \| 2 baths \| 1,204 sq.ft.	$224,875	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $1682 Airbnb ROI: N/A Traditional ROI: 5.9%
146 Saluda Street Chester, SC Step back in time with this beautifully preserved 1915 historic home, filled with original...	4 beds \| 3 baths \| 2,388 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.35% Airbnb Rental Income: $null Traditional Rental Income: $2802 Airbnb ROI: N/A Traditional ROI: 8.35%
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 \| N/A baths \| N/A	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.45% Airbnb Rental Income: $null Traditional Rental Income: $1992 Airbnb ROI: N/A Traditional ROI: 6.45%
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.	$187,200	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%
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.	$139,998	Airbnb cash on cash: N/A Traditional cash on cash: 7.66% Airbnb Rental Income: $null Traditional Rental Income: $1332 Airbnb ROI: N/A Traditional ROI: 7.66%
126 Sunset Drive Chester, SC Welcome to a beautifully renovated full brick home with modern luxury. This 4 bedroom, 2 b...	4 beds \| 2 baths \| 2,200 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $2360 Airbnb ROI: N/A Traditional ROI: 4.49%
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.	$342,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.14% Airbnb Rental Income: $null Traditional Rental Income: $2152 Airbnb ROI: N/A Traditional ROI: 5.14%
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.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $2115 Airbnb ROI: N/A Traditional ROI: 4.18%
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.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.32% Airbnb Rental Income: $null Traditional Rental Income: $1719 Airbnb ROI: N/A Traditional ROI: 8.32%
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! NO HOA! Great location to schoo...	3 beds \| 3 baths \| 1,909 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $2231 Airbnb ROI: N/A Traditional ROI: 4.28%

Real Estate investment in Chester, SC

There are 71 properties for sale in the city of Chester . The median list price in Chester is $225,888 and the average price per square foot is $143. In December 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 71 investment properties available for sale in Chester.

In 2025, the best neighborhood to buy investment property is 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 | 2,580 sq.ft.

$492,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2532

Airbnb ROI: N/A

Traditional ROI: 4.11%

107 Hinton Street

Chester, SC

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

$249,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2570

Airbnb ROI: N/A

Traditional ROI: 8.92%

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%

169 E Lacy Street

Chester, SC

3 beds | 2 baths | 1,405 sq.ft.

$215,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.94%

Airbnb Rental Income: $null

Traditional Rental Income: $1827

Airbnb ROI: N/A

Traditional ROI: 6.94%

530 Denton Avenue

Chester, SC

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

$248,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.39%

Airbnb Rental Income: $null

Traditional Rental Income: $1723

Airbnb ROI: N/A

Traditional ROI: 5.39%

1239 Carlisle White Road

Chester, SC

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

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.05%

Airbnb Rental Income: $null

Traditional Rental Income: $1894

Airbnb ROI: N/A

Traditional ROI: 5.05%

508 Old York Road

Chester, SC

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

$185,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.51%

Airbnb Rental Income: $null

Traditional Rental Income: $1514

Airbnb ROI: N/A