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 elegance and charm in this stunning 2017 custom-built home, featuring 5-6 spacio...	5 beds \| 4 baths \| 4,044 sq.ft.	$950,000	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%
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.	$399,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2470 Airbnb ROI: N/A Traditional ROI: 4.8%
15601 Roland View Drive Chester, VA Calling all first time home buyers! Discover comfort, convenience, and charm in this beaut...	3 beds \| 2 baths \| 1,116 sq.ft.	$309,950	Airbnb cash on cash: 1.48% Traditional cash on cash: 4.37% Airbnb Rental Income: $1427 Traditional Rental Income: $1843 Airbnb ROI: 1.48% Traditional ROI: 4.37%
3937 Harrmeadow Lane Chester, VA Welcome to Harrowgate Meadows! Come see this beautifully maintained 3-bedroom, 2-bath home...	3 beds \| 2 baths \| 1,635 sq.ft.	$385,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.74% Airbnb Rental Income: $1427 Traditional Rental Income: $2096 Airbnb ROI: 0.7% Traditional ROI: 3.74%
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%
9601 Varina Road Chester, VA Welcome to this private sanctuary nestled on over 6 peaceful acres, just 15 minutes from R...	4 beds \| 3 baths \| 2,002 sq.ft.	$435,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $2725 Airbnb ROI: N/A Traditional ROI: 4.87%
2804 Mimi Avenue Chester, VA Beautifully Renovated 4-Bedroom Home in Chester Step into this stunningly updated 4-bedroo...	4 beds \| 2 baths \| 1,686 sq.ft.	$322,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.39% Airbnb Rental Income: $null Traditional Rental Income: $2246 Airbnb ROI: N/A Traditional ROI: 5.39%
2420 Old Bermuda Hundred Road Chester, VA Welcome to the home that checks all your boxes! This four bedroom split level is rocking a...	4 beds \| 2 baths \| 2,150 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $2827 Airbnb ROI: N/A Traditional ROI: 6.46%
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.	$369,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 4.41% Airbnb Rental Income: $1427 Traditional Rental Income: $2412 Airbnb ROI: 0.33% Traditional ROI: 4.41%
14413 Eagle Rock Ave Chester, VA Welcome to 14413 Eagle Rock Avenue in Chester! This charming 2-story Colonial offers 3 bed...	3 beds \| 3 baths \| N/A	$350,000	Airbnb cash on cash: 1% Traditional cash on cash: 4.9% Airbnb Rental Income: $1427 Traditional Rental Income: $2283 Airbnb ROI: 1% Traditional ROI: 4.9%
4805 Wellington Farms Dr Chester, VA NEW TO MARKET - Beautifully maintained transitional home in one of Chester's most desirabl...	4 beds \| 3 baths \| N/A	$522,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $3211 Airbnb ROI: N/A Traditional ROI: 4.58%
15116 Alderwood Turn Chester, VA Nestled in a peaceful cul-de-sac, this charming two-story colonial offers the perfect blen...	3 beds \| 3 baths \| 1,886 sq.ft.	$368,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 4.94% Airbnb Rental Income: $1427 Traditional Rental Income: $2385 Airbnb ROI: 0.93% Traditional ROI: 4.94%
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 Welcome to 4608 Stoney Creek Parkway! Nestled in the sought-after Stoney Glen neighborhood...	4 beds \| 3 baths \| 2,096 sq.ft.	$399,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $2418 Airbnb ROI: N/A Traditional ROI: 4.3%
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.	$400,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 4.47% Airbnb Rental Income: $1427 Traditional Rental Income: $2429 Airbnb ROI: 0.66% Traditional ROI: 4.47%
13101 Harrowgate Road Chester, VA Look at the price per square foot this is incredibly priced to sell.One acre with 2500+ sq...	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%
1505 Enon Church Road Chester, VA Newly renovated! Step into effortless living with this beautifully updated, move-in ready ...	5 beds \| 3 baths \| 1,610 sq.ft.	$349,950	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.65% Airbnb Rental Income: $2991 Traditional Rental Income: $2136 Airbnb ROI: 5.16% Traditional ROI: 4.65%
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 the buyer's financing. This lovely 3-bedroom, 2-full-bath ranche...	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 MOVE IN READY, NEW CONSTRUCTION WITH BASEMENT. IMPROVED PRICE and LIMITED TIME $10,000 INC...	5 beds \| 4 baths \| 2,910 sq.ft.	$539,950	Airbnb cash on cash: 2.55% Traditional cash on cash: 4.11% Airbnb Rental Income: $2991 Traditional Rental Income: $3091 Airbnb ROI: 2.55% Traditional ROI: 4.11%
12713 Dell Hill Court Chester, VA Refined elegance meets modern comfort in this stately custom-built home, featuring 4 spaci...	4 beds \| 4 baths \| 3,707 sq.ft.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $3292 Airbnb ROI: N/A Traditional ROI: 1.9%
1906 Mainsail Lane Chester, VA Welcome to beautiful Twin Rivers at Meadowville Landing where landscaping is taken care of...	4 beds \| 3 baths \| 2,664 sq.ft.	$542,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $2831 Airbnb ROI: N/A Traditional ROI: 3.12%
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.	$539,990	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.61% Airbnb Rental Income: $1427 Traditional Rental Income: $2220 Airbnb ROI: 0.19% Traditional ROI: 2.61%
12012 Buckrudy Ter Chester, VA Welcome home to Luxury living in the last section of the Highlands! The Seneca plan offers...	5 beds \| 5 baths \| N/A	$622,685	Airbnb cash on cash: 1.99% Traditional cash on cash: 5.89% Airbnb Rental Income: $2991 Traditional Rental Income: $4573 Airbnb ROI: 1.99% Traditional ROI: 5.89%
4319 Poplar Village Drive Chester, VA MOVE IN READY NEW CONSTRUCTION! SEE NEW PROFESSIONAL PICTURES. The STAFFORD is just over 2...	4 beds \| 3 baths \| 2,516 sq.ft.	$489,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $2827 Airbnb ROI: N/A Traditional ROI: 4.13%
4709 Perdue Street Chester, VA EXCITING NEW PRICE! Nestled in the sought-after Bruce Farms neighborhood of Chester, Virgi...	5 beds \| 6 baths \| 5,620 sq.ft.	$689,500	Airbnb cash on cash: 1.6% Traditional cash on cash: 7.44% Airbnb Rental Income: $2991 Traditional Rental Income: $6058 Airbnb ROI: 1.6% Traditional ROI: 7.44%
12613 Poplar Village Place Chester, VA JUST COMPLETED, MUST SEE MOVE IN READY NEW CONSTRUCTION! See New Professional Pictures! Th...	5 beds \| 3 baths \| 2,624 sq.ft.	$521,911	Airbnb cash on cash: 2.72% Traditional cash on cash: 4.02% Airbnb Rental Income: $2991 Traditional Rental Income: $2938 Airbnb ROI: 2.72% Traditional ROI: 4.02%
3230 Perdue Springs Lane Chester, VA Located in the established Perdue Springs community, this well-maintained three-level town...	3 beds \| 3 baths \| 2,040 sq.ft.	$329,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.27% Airbnb Rental Income: $1427 Traditional Rental Income: $2443 Airbnb ROI: 0.61% Traditional ROI: 5.27%
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%
14831 Harrowgate Road Chester, VA A rare opportunity in the heart of Chester, this charming brick home sits on an expansive ...	3 beds \| 2 baths \| 1,344 sq.ft.	$350,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.25% Airbnb Rental Income: $1427 Traditional Rental Income: $1991 Airbnb ROI: 1.24% Traditional ROI: 4.25%
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.	$418,740	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.58% Airbnb Rental Income: $1427 Traditional Rental Income: $2211 Airbnb ROI: 0.5% Traditional ROI: 3.58%
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%
9517 Fuchsia Drive Chester, VA QUCK MOVE-IN! Introducing the Galen model, offering a modern and spacious open-concept liv...	4 beds \| 3 baths \| 2,798 sq.ft.	$519,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $3024 Airbnb ROI: N/A Traditional ROI: 4.22%
9525 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: 3.86% Airbnb Rental Income: $2991 Traditional Rental Income: $3022 Airbnb ROI: 2.47% Traditional ROI: 3.86%
1937 Enon Station Drive Chester, VA PRICE IMPROVEMENT TO $495,000! Better-than-new 2024 home offering 2,464 sq ft of beautiful...	4 beds \| 3 baths \| 2,464 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2656 Airbnb ROI: N/A Traditional ROI: 4.42%
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%

Real Estate investment in Chester, VA

There are 108 properties for sale in the city of Chester . The median list price in Chester is $427,000 and the average price per square foot is $193. In December 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,613.

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

There are 108 investment properties available for sale in Chester.

In 2025, 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 $2,613.

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.

$950,000

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%

11433 Chester Road

Chester, VA

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

$399,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.8%

Airbnb Rental Income: $null

Traditional Rental Income: $2470

Airbnb ROI: N/A

Traditional ROI: 4.8%

15601 Roland View Drive

Chester, VA

3 beds | 2 baths | 1,116 sq.ft.

$309,950

Airbnb cash on cash: 1.48%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1427

Traditional Rental Income: $1843

Airbnb ROI: 1.48%

Traditional ROI: 4.37%

3937 Harrmeadow Lane

Chester, VA

3 beds | 2 baths | 1,635 sq.ft.

$385,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1427

Traditional Rental Income: $2096

Airbnb ROI: 0.7%

Traditional ROI: 3.74%

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%

9601 Varina Road

Chester, VA

4 beds | 3 baths | 2,002 sq.ft.

$435,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2725

Airbnb ROI: N/A

Traditional ROI: 4.87%

2804 Mimi Avenue

Chester, VA

4 beds | 2 baths | 1,686 sq.ft.

$322,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2246

Airbnb ROI: N/A

Traditional ROI: 5.39%

2420 Old Bermuda Hundred Road

Chester, VA

4 beds | 2 baths | 2,150 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.46%

Airbnb Rental Income: $null

Traditional Rental Income: $2827

Airbnb ROI: N/A