Real Estate Investment Properties for Sale in Chester, VA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12700 Dell Hill Court Chester, VA Step into effortless elegance in this exquisite 2017 custom-built home, featuring 5-6 spac...	5 beds \| 4 baths \| 4,044 sq.ft.	$949,900	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.24% Airbnb Rental Income: $2991 Traditional Rental Income: $3562 Airbnb ROI: 0.81% Traditional ROI: 2.24%
10401 Hamlin Place Chester, VA Beautiful, charming home sits on a spacious lot that is conveniently located in Chester (C...	3 beds \| 2 baths \| 1,867 sq.ft.	$385,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.02% Airbnb Rental Income: $1427 Traditional Rental Income: $2195 Airbnb ROI: 0.71% Traditional ROI: 4.02%
11433 Chester Road Chester, VA Welcome to this charming all-brick rancher with a fully finished basement, offering space,...	4 beds \| 2 baths \| 1,997 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2470 Airbnb ROI: N/A Traditional ROI: 5.01%
3200 Sylvania Place Chester, VA Beautifully Renovated Cape with Country Charm! This stunning home welcomes you with a full...	4 beds \| 2 baths \| 1,512 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2199 Airbnb ROI: N/A Traditional ROI: 4.73%
16104 Sandwave Road Chester, VA Welcome to 16104 Sandwave Rd located in the heart of Chester. This well-kept home offers p...	3 beds \| 1 baths \| 1,104 sq.ft.	$270,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 4.63% Airbnb Rental Income: $1427 Traditional Rental Income: $1713 Airbnb ROI: 1.83% Traditional ROI: 4.63%
4204 N Cresthill Court Chester, VA Tucked away on a quiet cul-de-sac in Chester's Hidden Valley Estates subdivision, 4204 N. ...	5 beds \| 4 baths \| 3,691 sq.ft.	$450,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 7% Airbnb Rental Income: $2991 Traditional Rental Income: $3801 Airbnb ROI: 3.45% Traditional ROI: 7%
5030 Lippingham Drive Chester, VA Well-maintained and truly move-in ready, this home features fresh interior paint, new carp...	4 beds \| 3 baths \| 2,534 sq.ft.	$484,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2821 Airbnb ROI: N/A Traditional ROI: 4.27%
10419 Centralia Station Road Chester, VA Charming 4-Bedroom Home in a Peaceful Suburban Chesterfield Neighborhood Welcome to yo...	4 beds \| 3 baths \| 2,424 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 3.88%
812 Bermuda Hundred Road Chester, VA Rare 2.31-acre assemblage in Chesterfield's proven Bermuda/Meadowville commercial corridor...	3 beds \| 1 baths \| 1,080 sq.ft.	$510,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.02% Airbnb Rental Income: $1427 Traditional Rental Income: $1596 Airbnb ROI: 0.77% Traditional ROI: 2.02%
11416 Claimont Mill Drive Chester, VA Welcome to 11416 Claimont Drive - Built in 2021! Almost brand new! A beautifully maintaine...	3 beds \| 3 baths \| 1,716 sq.ft.	$359,999	Airbnb cash on cash: 0.37% Traditional cash on cash: 4.54% Airbnb Rental Income: $1427 Traditional Rental Income: $2412 Airbnb ROI: 0.37% Traditional ROI: 4.54%
5620 Ellingshire Dr #41-4 Chester, VA KITCHEN Appliances INCLUDED**! Townes at Iron Mill is the THE ONLY NEW, LOW-MAINTENANCE TO...	3 beds \| 3 baths \| N/A	$393,970	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.84% Airbnb Rental Income: $1427 Traditional Rental Income: $2551 Airbnb ROI: 0.64% Traditional ROI: 4.84%
4608 Stoney Creek Parkway Chester, VA Four Bedroom Colonial with 2.5 Baths and attached 2 car garage conveniently located in wel...	4 beds \| 3 baths \| 2,096 sq.ft.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $2418 Airbnb ROI: N/A Traditional ROI: 4.24%
13225 Old Happy Hill Road Chester, VA Prime 35.87-Acre Development Opportunity - Heart of Chester, VA! Exceptional opportunity t...	3 beds \| 4 baths \| 2,376 sq.ft.	$1,499,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.56% Airbnb Rental Income: $1427 Traditional Rental Income: $2598 Airbnb ROI: -0.59% Traditional ROI: 0.56%
1637 Forest Glenn Circle Chester, VA Charming 3-Bedroom Brick Rancher in Prime Enon/Chester Location! Welcome home to this spac...	3 beds \| 3 baths \| 2,225 sq.ft.	$389,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.62% Airbnb Rental Income: $1427 Traditional Rental Income: $2429 Airbnb ROI: 0.71% Traditional ROI: 4.62%
12655 GREEN GARDEN Way Chester, VA Searching for the right place to call home in an established neighborhood where folks wave...	4 beds \| 3 baths \| 2,716 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $3132 Airbnb ROI: N/A Traditional ROI: 5.02%
13101 Harrowgate Road Chester, VA Back on the market!! This home has just had a brand new roof put on to go with the rest of...	4 beds \| 3 baths \| 2,525 sq.ft.	$409,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.66% Airbnb Rental Income: $null Traditional Rental Income: $3283 Airbnb ROI: N/A Traditional ROI: 6.66%
10906 Timonium Drive Chester, VA Contemporary 3-Bed, 3-Bath 1447 sq ft Home with Modern Renovations in Chester's Mineola Su...	3 beds \| 3 baths \| 1,447 sq.ft.	$359,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.91% Airbnb Rental Income: $1427 Traditional Rental Income: $1946 Airbnb ROI: 1.11% Traditional ROI: 3.91%
4119 White Cir Chester, VA Meet the Hudson in Wellspring - designed to fit the way you live, even when the way you li...	4 beds \| 3 baths \| N/A	$516,620	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $2839 Airbnb ROI: N/A Traditional ROI: 3.87%
4300 Poplar Village Drive Chester, VA A popular plan among buyers, The Belvedere is for anyone looking for main level living hom...	3 beds \| 2 baths \| 2,000 sq.ft.	$482,420	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.34% Airbnb Rental Income: $1427 Traditional Rental Income: $2430 Airbnb ROI: 0.17% Traditional ROI: 3.34%
3831 Wood Dale Rd Chester, VA BACK ON THE MARKET DUE TO FINANCING. This lovely 3-bedroom, 2-full-bath rancher boasts an...	4 beds \| 2 baths \| N/A	$314,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 5.97%
12607 Poplar Village Place Chester, VA NEW IMPROVED PRICE!! MOVE IN READY, NEW CONSTRUCTION WITH BASEMENT! NO HOA! Meet The ROWLA...	5 beds \| 4 baths \| 2,910 sq.ft.	$524,950	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.28% Airbnb Rental Income: $2991 Traditional Rental Income: $3091 Airbnb ROI: 2.67% Traditional ROI: 4.28%
1792 Outrigger Drive Chester, VA MOVE-IN READY! The Wescott is a three-bedroom, three-and-a-half bath, ranch-style home wit...	3 beds \| 4 baths \| 2,648 sq.ft.	$529,990	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.67% Airbnb Rental Income: $1427 Traditional Rental Income: $2220 Airbnb ROI: 0.21% Traditional ROI: 2.67%
3913 Terjo Lane Chester, VA This house is move in ready with lots of recent upgrades. Hardiplank siding exterior. Many...	4 beds \| 2 baths \| 2,158 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $2420 Airbnb ROI: N/A Traditional ROI: 5.21%
11975 Quay Street Chester, VA Fully renovated 4 bedroom, 3 full bathroom home offering 2,066 sq ft of modern living in t...	4 beds \| 3 baths \| 2,066 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2674 Airbnb ROI: N/A Traditional ROI: 5.4%
4103 Kings Gate Road Chester, VA This spacious and freshly updated 5-bedroom, 3-bath home gives you a ton of value for the ...	5 beds \| 3 baths \| 2,707 sq.ft.	$415,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 5.46% Airbnb Rental Income: $2991 Traditional Rental Income: $2950 Airbnb ROI: 3.8% Traditional ROI: 5.46%
9524 Fuchsia Drive Chester, VA MOVE-IN READY! The 1333 sq ft Essex model offers a spacious open-concept living space, ide...	3 beds \| 3 baths \| 1,333 sq.ft.	$399,990	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.83% Airbnb Rental Income: $1427 Traditional Rental Income: $2211 Airbnb ROI: 0.61% Traditional ROI: 3.83%
9513 Fuchsia Drive Chester, VA QUICK MOVE-IN! Welcome to the Hayden model, offering a modern open-concept living space de...	5 beds \| 3 baths \| 2,974 sq.ft.	$552,740	Airbnb cash on cash: 2.47% Traditional cash on cash: 4.02% Airbnb Rental Income: $2991 Traditional Rental Income: $3106 Airbnb ROI: 2.47% Traditional ROI: 4.02%
9549 Fuchsia Drive Chester, VA Welcome to the Penwell, a beautifully designed 2,159 sq ft home offering a modern and spac...	3 beds \| 3 baths \| 2,159 sq.ft.	$458,990	Airbnb cash on cash: 0.3% Traditional cash on cash: 4.22% Airbnb Rental Income: $1427 Traditional Rental Income: $2687 Airbnb ROI: 0.3% Traditional ROI: 4.22%
11709 Boyd Rd Chester, VA Charming Brick Home with Full Basement on Nearly ÃÂ¾ Acres! Welcome to this beautifully m...	5 beds \| 3 baths \| N/A	$399,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 6.52% Airbnb Rental Income: $2991 Traditional Rental Income: $3170 Airbnb ROI: 4.2% Traditional ROI: 6.52%
14149 Enon Station Ter Chester, VA This Brand-New Home is Ready Now! Call today to schedule your tour! Welcome to Enon Stati...	3 beds \| 3 baths \| N/A	$434,990	Airbnb cash on cash: 0.41% Traditional cash on cash: 4.95% Airbnb Rental Income: $1427 Traditional Rental Income: $2849 Airbnb ROI: 0.41% Traditional ROI: 4.95%
15908 Tri Gate Road Chester, VA Welcome home to this charming Cottage Style home in the up-and-coming neighborhood of Some...	3 beds \| 2 baths \| 1,350 sq.ft.	$295,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.71% Airbnb Rental Income: $1427 Traditional Rental Income: $1892 Airbnb ROI: 1.5% Traditional ROI: 4.71%
13525 Thornsett Lane Chester, VA Why wait for New when you can have this updated home now! One of the best floor plans in t...	5 beds \| 4 baths \| 2,796 sq.ft.	$489,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.9% Airbnb Rental Income: $2991 Traditional Rental Income: $3117 Airbnb ROI: 3.12% Traditional ROI: 4.9%
9521 Fuchsia Drive Chester, VA Welcome to the Penwell, a beautifully designed home offering a modern and spacious open-co...	3 beds \| 3 baths \| 2,526 sq.ft.	$516,740	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.75% Airbnb Rental Income: $1427 Traditional Rental Income: $2782 Airbnb ROI: 0.06% Traditional ROI: 3.75%
4242 Poplar Village Drive Chester, VA Welcome Home! As you walk in through the large covered stoop, you come across your spaciou...	4 beds \| 3 baths \| 2,072 sq.ft.	$452,129	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $2627 Airbnb ROI: N/A Traditional ROI: 4.17%
9529 Fuchsia Drive Chester, VA Introducing the Galen model, offering a modern and spacious open-concept living space perf...	4 beds \| 3 baths \| 2,798 sq.ft.	$540,740	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $3011 Airbnb ROI: N/A Traditional ROI: 3.96%
9533 Fuchsia Drive Chester, VA Welcome to the Penwell, a beautifully designed home offering a modern and spacious open-co...	3 beds \| 3 baths \| 2,558 sq.ft.	$516,990	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.76% Airbnb Rental Income: $1427 Traditional Rental Income: $2785 Airbnb ROI: 0.06% Traditional ROI: 3.76%
712 Dove Path Lane Chester, VA BACK ON THE MARKET DUE TO NO FAULT OF THE SELLER! Buyer changed plans 2 days before closin...	4 beds \| 4 baths \| 2,470 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $3003 Airbnb ROI: N/A Traditional ROI: 5.25%
9536 Fuchsia Drive Chester, VA Welcome to the Hayden model, offering a modern open-concept living space designed for both...	5 beds \| 3 baths \| 2,511 sq.ft.	$503,990	Airbnb cash on cash: 2.88% Traditional cash on cash: 4.13% Airbnb Rental Income: $2991 Traditional Rental Income: $2895 Airbnb ROI: 2.88% Traditional ROI: 4.13%
4401 Village Garden Circle Chester, VA ALL BRICK 1.5 STORY HOME. Owners suite and 2nd bedroom on 1st floor. Walk right in to the ...	3 beds \| 3 baths \| 2,502 sq.ft.	$425,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.2% Airbnb Rental Income: $1427 Traditional Rental Income: $2516 Airbnb ROI: 0.4% Traditional ROI: 4.2%
9537 Fuchsia Drive Chester, VA Welcome to the Hayden model, offering a modern open-concept living space designed for both...	5 beds \| 3 baths \| 2,974 sq.ft.	$566,990	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.85% Airbnb Rental Income: $2991 Traditional Rental Income: $3091 Airbnb ROI: 2.36% Traditional ROI: 3.85%

Real Estate investment in Chester, VA

There are 88 properties for sale in the city of Chester . The median list price in Chester is $418,120 and the average price per square foot is $196. In January 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,516.

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

There are 88 investment properties available for sale in Chester.

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

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $2,516.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VA

12700 Dell Hill Court

Chester, VA

5 beds | 4 baths | 4,044 sq.ft.

$949,900

Airbnb cash on cash: 0.81%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $2991

Traditional Rental Income: $3562

Airbnb ROI: 0.81%

Traditional ROI: 2.24%

10401 Hamlin Place

Chester, VA

3 beds | 2 baths | 1,867 sq.ft.

$385,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $1427

Traditional Rental Income: $2195

Airbnb ROI: 0.71%

Traditional ROI: 4.02%

11433 Chester Road

Chester, VA

4 beds | 2 baths | 1,997 sq.ft.

$385,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2470

Airbnb ROI: N/A

Traditional ROI: 5.01%

3200 Sylvania Place

Chester, VA

4 beds | 2 baths | 1,512 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2199

Airbnb ROI: N/A

Traditional ROI: 4.73%

16104 Sandwave Road

Chester, VA

3 beds | 1 baths | 1,104 sq.ft.

$270,000

Airbnb cash on cash: 1.83%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $1427

Traditional Rental Income: $1713

Airbnb ROI: 1.83%

Traditional ROI: 4.63%

4204 N Cresthill Court

Chester, VA

5 beds | 4 baths | 3,691 sq.ft.

$450,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 7%

Airbnb Rental Income: $2991

Traditional Rental Income: $3801

Airbnb ROI: 3.45%

Traditional ROI: 7%

5030 Lippingham Drive

Chester, VA

4 beds | 3 baths | 2,534 sq.ft.

$484,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.27%

Airbnb Rental Income: $null

Traditional Rental Income: $2821

Airbnb ROI: N/A

Traditional ROI: 4.27%

10419 Centralia Station Road

Chester, VA

4 beds | 3 baths | 2,424 sq.ft.

$499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.88%

Airbnb Rental Income: $null

Traditional Rental Income: $2718

Airbnb ROI: N/A