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
12309 Windsor Road Chester, VA Welcome to 12309 Windsor Road, in the heart of Chester. This lovely home with 9 ft ceiling...	4 beds \| 3 baths \| 2,378 sq.ft.	$485,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $2675 Airbnb ROI: N/A Traditional ROI: 3.92%
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: N/A Traditional cash on cash: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $3562 Airbnb ROI: N/A Traditional ROI: 2.24%
403 Hogans Court Chester, VA Back On Market Due To No Fault Of Sellers!!! Welcome to this exceptional 3-story home loca...	4 beds \| 4 baths \| 3,932 sq.ft.	$669,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3441 Airbnb ROI: N/A Traditional ROI: 3.51%
13909 Highpaige Way Chester, VA Welcome to Stoney Glen West! Tucked away on a quiet cul-de-sac, this beautifully updated 4...	4 beds \| 3 baths \| 2,274 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 4.38%
4613 Crossgate Road Chester, VA Set on an oversized lot in Lora Lynn Heights, 4613 Crossgate Road offers space, charm, and...	3 beds \| 2 baths \| 2,621 sq.ft.	$365,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 3.01% Airbnb Rental Income: $616 Traditional Rental Income: $1781 Airbnb ROI: -1.24% Traditional ROI: 3.01%
11551 Teterling Road Chester, VA Beautiful all brick home with exceptional curb appeal in a highly desirable Chester locati...	4 beds \| 3 baths \| 2,526 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $2800 Airbnb ROI: N/A Traditional ROI: 3.76%
10400 Hamlin Dr Chester, VA Incredibly appointed two-story Traditional style home located in a lovely community with g...	4 beds \| 3 baths \| N/A	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $2857 Airbnb ROI: N/A Traditional ROI: 5.85%
3924 Belspring Road Chester, VA Colonial home in Hidden Valley Estates, 4 generous bedrooms and 2 full bathroom upstairs, ...	4 beds \| 3 baths \| 2,460 sq.ft.	$430,800	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 4.96%
4237 Wells Ridge Court Chester, VA Spacious 2,892 sq ft home offering a functional layout and plenty of room to spread out! T...	4 beds \| 4 baths \| 2,878 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $2755 Airbnb ROI: N/A Traditional ROI: 3.85%
14205 Sonnenburg Drive Chester, VA Welcome to your private retreat in Chester in popular Mistwood Forest! This impeccably mai...	3 beds \| 3 baths \| 1,517 sq.ft.	$329,950	Airbnb cash on cash: -1.02% Traditional cash on cash: 5.17% Airbnb Rental Income: $616 Traditional Rental Income: $2243 Airbnb ROI: -1.02% Traditional ROI: 5.17%
12420 Ivyridge Court Chester, VA Welcome home! This beautiful residence features formal living and dining rooms, along with...	4 beds \| 3 baths \| 2,016 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2522 Airbnb ROI: N/A Traditional ROI: 4.9%
15910 Gary Avenue Chester, VA Professional photos coming 4/10. Nicely Remodeled 4-Bedroom Home with Private Pool & Fence...	4 beds \| 2 baths \| 1,436 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2091 Airbnb ROI: N/A Traditional ROI: 5.27%
14305 Sonnenburg Drive Chester, VA Welcome to 14305 Sonnenburg Drive, a beautifully updated home where quality improvements a...	3 beds \| 3 baths \| 1,641 sq.ft.	$360,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.65% Airbnb Rental Income: $616 Traditional Rental Income: $2195 Airbnb ROI: -0.89% Traditional ROI: 4.65%
10419 Centralia Station Road Chester, VA Back on the market and ready to sell! The seller welcomes strong, reasonable offers. Charm...	4 beds \| 3 baths \| 2,424 sq.ft.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 3.91%
2937 ABBEYDALE Court Chester, VA Welcome to this beautiful four-bedroom home nestled in the heart of Chester! Situated on a...	4 beds \| 3 baths \| 2,392 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $2755 Airbnb ROI: N/A Traditional ROI: 4.88%
1520 Rustling Cedar Lane Chester, VA Nestled on 2.76 private acres in Henrico County, 1520 Rustling Cedar Lane offers a rare bl...	4 beds \| 4 baths \| 2,533 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $3097 Airbnb ROI: N/A Traditional ROI: 2.43%
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: -0.65% Traditional cash on cash: 2.02% Airbnb Rental Income: $616 Traditional Rental Income: $1596 Airbnb ROI: -0.65% Traditional ROI: 2.02%
4005 Somerlane Circle Chester, VA Welcome to 4005 Somerlane Circle in the established Somerset subdivision of Chesterfield C...	3 beds \| 3 baths \| 1,885 sq.ft.	$339,950	Airbnb cash on cash: -1.23% Traditional cash on cash: 4.77% Airbnb Rental Income: $616 Traditional Rental Income: $2241 Airbnb ROI: -1.23% Traditional ROI: 4.77%
4331 Poplar Village Drive Chester, VA Don't miss this MOVE IN READY, NEW CONSTRUCTION. NO HOA! Poplar Village Almost Sold Out! T...	3 beds \| 3 baths \| 2,072 sq.ft.	$449,950	Airbnb cash on cash: -1.29% Traditional cash on cash: 4.5% Airbnb Rental Income: $616 Traditional Rental Income: $2762 Airbnb ROI: -1.29% Traditional ROI: 4.5%
12601 Poplar Village Place Chester, VA The Stafford by Shurm Homes offers over 2,400 square feet of beautifully designed living s...	4 beds \| 3 baths \| 2,503 sq.ft.	$518,247	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2575 Airbnb ROI: N/A Traditional ROI: 3.29%
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: -1.19% Traditional cash on cash: 4.84% Airbnb Rental Income: $616 Traditional Rental Income: $2551 Airbnb ROI: -1.19% Traditional ROI: 4.84%
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: -1.07% Traditional cash on cash: 0.56% Airbnb Rental Income: $616 Traditional Rental Income: $2598 Airbnb ROI: -1.07% Traditional ROI: 0.56%
13101 Harrowgate Road Chester, VA *Back on the market at no fault of the seller* Step into a home where comfort meets mo...	4 beds \| 3 baths \| 2,525 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.34% Airbnb Rental Income: $null Traditional Rental Income: $3283 Airbnb ROI: N/A Traditional ROI: 7.34%
2723 Goyne Terrace Chester, VA Your Private Oasis Awaits! This impeccably maintained townhome offers the perfect blend of...	2 beds \| 3 baths \| 1,320 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.77% Airbnb Rental Income: $null Traditional Rental Income: $1795 Airbnb ROI: N/A Traditional ROI: 3.77%
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: -0.89% Traditional cash on cash: 3.91% Airbnb Rental Income: $616 Traditional Rental Income: $1946 Airbnb ROI: -0.89% 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: -1.32% Traditional cash on cash: 3.34% Airbnb Rental Income: $616 Traditional Rental Income: $2430 Airbnb ROI: -1.32% Traditional ROI: 3.34%
13110 Bluemont Road Chester, VA Elegant and thoughtfully designed, this 2,956 sq. ft. 4-bedroom, 2.5-bath home in the esta...	4 beds \| 3 baths \| 2,956 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $3035 Airbnb ROI: N/A Traditional ROI: 4.59%
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%
1404 Enon Church Road Chester, VA Beautifully renovated 3-bedroom, 2.5-bath home offering modern updates and move-in-ready c...	3 beds \| 3 baths \| 1,549 sq.ft.	$340,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 5.35% Airbnb Rental Income: $616 Traditional Rental Income: $2327 Airbnb ROI: -0.92% Traditional ROI: 5.35%
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: -1.54% Traditional cash on cash: 3.55% Airbnb Rental Income: $616 Traditional Rental Income: $2782 Airbnb ROI: -1.54% Traditional ROI: 3.55%
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: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $3011 Airbnb ROI: N/A Traditional ROI: 3.76%
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: -1.54% Traditional cash on cash: 3.55% Airbnb Rental Income: $616 Traditional Rental Income: $2785 Airbnb ROI: -1.54% Traditional ROI: 3.55%
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: -1.79% Traditional cash on cash: 3.71% Airbnb Rental Income: $616 Traditional Rental Income: $2516 Airbnb ROI: -1.79% Traditional ROI: 3.71%
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: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $3091 Airbnb ROI: N/A Traditional ROI: 3.85%
1801 Galley Pl Chester, VA Maintenance-free living in highly sought-after Twin Rivers at Meadowville Landing! Landsca...	3 beds \| 3 baths \| N/A	$455,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 3.44% Airbnb Rental Income: $616 Traditional Rental Income: $2431 Airbnb ROI: -1.5% Traditional ROI: 3.44%
12618 Poplar Village Place Chester, VA The Craftsman Charles is a charming ranch style home now available in the highly desirable...	3 beds \| 2 baths \| 1,232 sq.ft.	$428,626	Airbnb cash on cash: -1.24% Traditional cash on cash: 3.03% Airbnb Rental Income: $616 Traditional Rental Income: $2040 Airbnb ROI: -1.24% Traditional ROI: 3.03%
4248 Poplar Village Drive Chester, VA Construction Starting Soon. Limited Time to SELECT INTERIOR COLORS AND FINISHES! FINAL LOT...	4 beds \| 4 baths \| 2,963 sq.ft.	$571,612	Airbnb cash on cash: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $1963 Airbnb ROI: N/A Traditional ROI: 1.69%
5501 Buxton Court Chester, VA RECENT PRICE IMPROVEMENT!NEW 15 SEER CARRIER DUAL FUEL HVAC SYSTEM JUST INSTALLED WITH 10 ...	4 beds \| 3 baths \| 3,446 sq.ft.	$524,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $3265 Airbnb ROI: N/A Traditional ROI: 4.63%
11325 Vulcan Ln Chester, VA Enjoy one-level living in Womack Green, in the heart of Chester, with maintenance free liv...	3 beds \| 2 baths \| N/A	$399,950	Airbnb cash on cash: -1.48% Traditional cash on cash: 3.35% Airbnb Rental Income: $616 Traditional Rental Income: $2136 Airbnb ROI: -1.48% Traditional ROI: 3.35%

Real Estate investment in Chester, VA

There are 109 properties for sale in the city of Chester . The median list price in Chester is $456,000 and the average price per square foot is $185. In April 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,687.

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

There are 109 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 $2,687.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VA

12309 Windsor Road

Chester, VA

4 beds | 3 baths | 2,378 sq.ft.

$485,950

Airbnb cash on cash: N/A

Traditional cash on cash: 3.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2675

Airbnb ROI: N/A

Traditional ROI: 3.92%

12700 Dell Hill Court

Chester, VA

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

$949,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.24%

Airbnb Rental Income: $null

Traditional Rental Income: $3562

Airbnb ROI: N/A

Traditional ROI: 2.24%

403 Hogans Court

Chester, VA

4 beds | 4 baths | 3,932 sq.ft.

$669,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $3441

Airbnb ROI: N/A

Traditional ROI: 3.51%

13909 Highpaige Way

Chester, VA

4 beds | 3 baths | 2,274 sq.ft.

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2718

Airbnb ROI: N/A

Traditional ROI: 4.38%

4613 Crossgate Road

Chester, VA

3 beds | 2 baths | 2,621 sq.ft.

$365,000

Airbnb cash on cash: -1.24%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $616

Traditional Rental Income: $1781

Airbnb ROI: -1.24%

Traditional ROI: 3.01%

11551 Teterling Road

Chester, VA

4 beds | 3 baths | 2,526 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.76%

Airbnb Rental Income: $null

Traditional Rental Income: $2800

Airbnb ROI: N/A

Traditional ROI: 3.76%

10400 Hamlin Dr

Chester, VA

4 beds | 3 baths | N/A

$385,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2857

Airbnb ROI: N/A

Traditional ROI: 5.85%

3924 Belspring Road

Chester, VA

4 beds | 3 baths | 2,460 sq.ft.

$430,800

Airbnb cash on cash: N/A

Traditional cash on cash: 4.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2785

Airbnb ROI: N/A