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: 3.08% Traditional cash on cash: 2.24% Airbnb Rental Income: $5396 Traditional Rental Income: $3562 Airbnb ROI: 3.08% Traditional ROI: 2.24%
3802 Seasigh Court Chester, VA MOVE-IN-READY, Renovated 4 Bedrooms, 2 Full Baths, with NEW-NEW-NEW- Quartz Countertop in ...	4 beds \| 2 baths \| 1,601 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2221 Airbnb ROI: N/A Traditional ROI: 4.73%
12703 Kelsey Pointe Ct Chester, VA Custom home, freshly painted on a cul-de-sac with potential IN-LAW SUITE! Formal living an...	4 beds \| 4 baths \| N/A	$529,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $3465 Airbnb ROI: N/A Traditional ROI: 5.04%
11608 Hickory Landing Place Chester, VA Welcome to this beautifully maintained home offering over 4,000 square feet of living spac...	4 beds \| 4 baths \| 4,137 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.98% Airbnb Rental Income: $null Traditional Rental Income: $4221 Airbnb ROI: N/A Traditional ROI: 6.98%
15601 Meridian Avenue Chester, VA Oh, the space you'll have!! This 3-bedroom, 2-bath Tri-Level home sits on .83 acres in the...	3 beds \| 2 baths \| 1,592 sq.ft.	$320,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.48% Airbnb Rental Income: $3022 Traditional Rental Income: $1980 Airbnb ROI: 5.64% Traditional ROI: 4.48%
3219 Castlebury Drive Chester, VA Updates throughout including New Flooring on the main level and new carpet on the second f...	3 beds \| 3 baths \| 1,777 sq.ft.	$369,993	Airbnb cash on cash: 4.71% Traditional cash on cash: 4.92% Airbnb Rental Income: $3022 Traditional Rental Income: $2402 Airbnb ROI: 4.71% Traditional ROI: 4.92%
13920 Sandy Oak Road Chester, VA Back on the market due to NO FAULT of the sellers. Buyers financing fell through- Welcome ...	4 beds \| 3 baths \| 2,200 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $2657 Airbnb ROI: N/A Traditional ROI: 5.25%
1831 Galley Place Chester, VA Welcome to 1831 Galley Place in Twin Rivers at Meadowville Landing. Built in 2021 by Eastw...	4 beds \| 3 baths \| 2,811 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $2869 Airbnb ROI: N/A Traditional ROI: 3.81%
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.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2246 Airbnb ROI: N/A Traditional ROI: 4.91%
3105 Lalonde Drive Chester, VA Don't miss this adorable ranch in the quiet Chester community of Millcreek. Upon entering ...	3 beds \| 2 baths \| 1,200 sq.ft.	$295,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 4.71% Airbnb Rental Income: $3022 Traditional Rental Income: $1886 Airbnb ROI: 6.3% Traditional ROI: 4.71%
3019 Ramsey Drive Chester, VA Price Improvement!!! MOTIVATED SELLER!! Welcome Home to The Villages at Longmeadow! Get re...	3 beds \| 3 baths \| 1,898 sq.ft.	$355,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 5.07% Airbnb Rental Income: $3022 Traditional Rental Income: $2366 Airbnb ROI: 4.96% Traditional ROI: 5.07%
11207 Arbor Green Drive Chester, VA Come fall in love with this beautifully updated brick and vinyl rancher in Arbor Landing! ...	4 beds \| 3 baths \| 2,172 sq.ft.	$419,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $2710 Airbnb ROI: N/A Traditional ROI: 4.89%
10225 Centralia Station Rd Chester, VA Charming Craftsman ranch with upstairs guest suite offering first floor living! Welcome to...	4 beds \| 3 baths \| N/A	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $2563 Airbnb ROI: N/A Traditional ROI: 3.44%
2330 Hubert Lane Chester, VA Welcome to 2330 Hubert Ln. - A beautifully updated 3-bedroom/3-bathroom home on a spacious...	3 beds \| 3 baths \| 2,016 sq.ft.	$419,999	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.49% Airbnb Rental Income: $3022 Traditional Rental Income: $2018 Airbnb ROI: 4.28% Traditional ROI: 3.49%
6114 Walnut Landing Way Chester, VA Newly available in Arbor Landing is this beautiful colonial home located just 1 short walk...	5 beds \| 4 baths \| 2,754 sq.ft.	$500,000	Airbnb cash on cash: 7.21% Traditional cash on cash: 5.92% Airbnb Rental Income: $5396 Traditional Rental Income: $3706 Airbnb ROI: 7.21% Traditional ROI: 5.92%
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: 4.78% Traditional cash on cash: 4.94% Airbnb Rental Income: $3022 Traditional Rental Income: $2385 Airbnb ROI: 4.78% 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: 4.24% Traditional cash on cash: 4.84% Airbnb Rental Income: $3022 Traditional Rental Income: $2551 Airbnb ROI: 4.24% Traditional ROI: 4.84%
4608 Stoney Creek Parkway Chester, VA Bonus: Seller is willing to contribute up to $7,500 toward buyer's closing costs. Welcome ...	4 beds \| 3 baths \| 2,096 sq.ft.	$409,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $2418 Airbnb ROI: N/A Traditional ROI: 4.18%
2403 Bermuda Avenue Chester, VA Welcome to a residence of elegance that is meticulously maintained and located at the end ...	4 beds \| 4 baths \| 4,740 sq.ft.	$1,299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $3772 Airbnb ROI: N/A Traditional ROI: 1.55%
1713 Galley Place Chester, VA This is a to-be built home! The Stanley is a four-bedroom, 3-bath, ranch-style home with a...	4 beds \| 3 baths \| 2,162 sq.ft.	$472,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $2182 Airbnb ROI: N/A Traditional ROI: 3.06%
1806 Outrigger Drive Chester, VA This is a to-be built home! The Avery is a three-bedroom, two-bath, ranch-style home with ...	3 beds \| 2 baths \| 1,738 sq.ft.	$500,080	Airbnb cash on cash: 3.13% Traditional cash on cash: 2.94% Airbnb Rental Income: $3022 Traditional Rental Income: $2241 Airbnb ROI: 3.13% Traditional ROI: 2.94%
4900 Wellington Farms Drive Chester, VA MOTIVATED SELLER !! SPACIOUS & RECENTLY RENOVATED! Step into nearly 5,000 square feet of e...	5 beds \| 4 baths \| 4,908 sq.ft.	$729,999	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.44% Airbnb Rental Income: $5396 Traditional Rental Income: $3589 Airbnb ROI: 4.5% Traditional ROI: 3.44%
3818 Belspring Road Chester, VA MOVE-IN READY!! The Caldwell features 3 bedrooms, 2.5 baths, and a side-load garage. As yo...	3 beds \| 3 baths \| 2,071 sq.ft.	$539,990	Airbnb cash on cash: 2.57% Traditional cash on cash: 3.01% Airbnb Rental Income: $3022 Traditional Rental Income: $2551 Airbnb ROI: 2.57% Traditional ROI: 3.01%
13101 Harrowgate Road Chester, VA The seller just made it easier to say yes to this address!!! Price just imporved by 10k!! ...	4 beds \| 3 baths \| 2,525 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $3283 Airbnb ROI: N/A Traditional ROI: 6.14%
1812 Outrigger Drive Chester, VA This is a to-be built home! The Avery is a four-bedroom and three-bath home with durable E...	4 beds \| 3 baths \| 1,829 sq.ft.	$495,890	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $2167 Airbnb ROI: N/A Traditional ROI: 2.81%
4200 Poplar Village Drive Chester, VA PRICE IMPROVEMENT! MOVE IN READY NEW CONSTRUCTION! NO HOA! Offering $10,000 toward Closing...	3 beds \| 2 baths \| 1,232 sq.ft.	$339,950	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.02% Airbnb Rental Income: $3022 Traditional Rental Income: $1964 Airbnb ROI: 5.16% Traditional ROI: 4.02%
9191 Osborne Turnpike Chester, VA Stunning New Craftsman-style home To Be Built on 3.613 acres in the serene Cedar Tree line...	4 beds \| 4 baths \| 3,268 sq.ft.	$820,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 3.29%
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: 3.12% Traditional cash on cash: 3.34% Airbnb Rental Income: $3022 Traditional Rental Income: $2430 Airbnb ROI: 3.12% Traditional ROI: 3.34%
3831 Wood Dale Rd Chester, VA Back on the market due to buyer's financing. This lovely 3 bedroom, 2-full-bath rancher bo...	3 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 5.76% Airbnb Rental Income: $3022 Traditional Rental Income: $2385 Airbnb ROI: 5.57% Traditional ROI: 5.76%
4018 White Creek Ct Chester, VA THIS IS A SPEC! New construction without the wait! This BRAND NEW York floorplan WITH FIN...	5 beds \| 4 baths \| N/A	$639,990	Airbnb cash on cash: 6% Traditional cash on cash: 4.53% Airbnb Rental Income: $5396 Traditional Rental Income: $3431 Airbnb ROI: 6% Traditional ROI: 4.53%
14313 Woodleigh Dr Chester, VA Looking for a spacious home with primary bedrooms upstairs AND downstairs? That's just p...	5 beds \| 4 baths \| N/A	$509,950	Airbnb cash on cash: 7.08% Traditional cash on cash: 5.41% Airbnb Rental Income: $5396 Traditional Rental Income: $3515 Airbnb ROI: 7.08% Traditional ROI: 5.41%
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.	$549,950	Airbnb cash on cash: 6.37% Traditional cash on cash: 4% Airbnb Rental Income: $5396 Traditional Rental Income: $3091 Airbnb ROI: 6.37% Traditional ROI: 4%
12145 Calgary Loop Chester, VA QUICK MOVE-IN!! The Matisse condo at Moore's Lake offers spacious, maintenance free living...	3 beds \| 3 baths \| N/A	$329,990	Airbnb cash on cash: 5.4% Traditional cash on cash: 7.04% Airbnb Rental Income: $3022 Traditional Rental Income: $2840 Airbnb ROI: 5.4% Traditional ROI: 7.04%
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%
1806 Galley Place Chester, VA This is a to-be built home! The Avery is a three-bedroom, two-bath home with an open floor...	3 beds \| 2 baths \| 1,829 sq.ft.	$462,210	Airbnb cash on cash: 3.46% Traditional cash on cash: 3.35% Airbnb Rental Income: $3022 Traditional Rental Income: $2284 Airbnb ROI: 3.46% Traditional ROI: 3.35%
4236 Poplar Village Drive Chester, VA One of our BRAND NEW floorplans, the Albany offers starts just shy of 3000 sq ft, so you h...	4 beds \| 3 baths \| 2,924 sq.ft.	$532,009	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $3160 Airbnb ROI: N/A Traditional ROI: 4.33%
4318 Poplar Village Drive Chester, VA Welcome to The Ellwood- an ideal first floor primary home that does not skip out on square...	4 beds \| 3 baths \| 2,061 sq.ft.	$492,469	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $2580 Airbnb ROI: N/A Traditional ROI: 3.56%
1906 Mainsail Lane Chester, VA Welcome to beautiful Twin Rivers at Meadowville Landing. Re-launched listing with new pric...	4 beds \| 3 baths \| 2,664 sq.ft.	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $2831 Airbnb ROI: N/A Traditional ROI: 3.1%
4312 Poplar Village Drive Chester, VA One of our BRAND NEW floorplans, the Stafford offers flexible space so that you can person...	4 beds \| 3 baths \| 2,503 sq.ft.	$469,885	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $2892 Airbnb ROI: N/A Traditional ROI: 4.53%

Real Estate investment in Chester, VA

There are 120 properties for sale in the city of Chester . The median list price in Chester is $439,000 and the average price per square foot is $183. In September 2025, the average monthly cash on cash return in Chester is 5.00%. The average monthly rental income in Chester is $2,657.

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

There are 120 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 $3,022.

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: 3.08%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $5396

Traditional Rental Income: $3562

Airbnb ROI: 3.08%

Traditional ROI: 2.24%

3802 Seasigh Court

Chester, VA

4 beds | 2 baths | 1,601 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2221

Airbnb ROI: N/A

Traditional ROI: 4.73%

12703 Kelsey Pointe Ct

Chester, VA

4 beds | 4 baths | N/A

$529,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3465

Airbnb ROI: N/A

Traditional ROI: 5.04%

11608 Hickory Landing Place

Chester, VA

4 beds | 4 baths | 4,137 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.98%

Airbnb Rental Income: $null

Traditional Rental Income: $4221

Airbnb ROI: N/A

Traditional ROI: 6.98%

15601 Meridian Avenue

Chester, VA

3 beds | 2 baths | 1,592 sq.ft.

$320,000

Airbnb cash on cash: 5.64%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $3022

Traditional Rental Income: $1980

Airbnb ROI: 5.64%

Traditional ROI: 4.48%

3219 Castlebury Drive

Chester, VA

3 beds | 3 baths | 1,777 sq.ft.

$369,993

Airbnb cash on cash: 4.71%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $3022

Traditional Rental Income: $2402

Airbnb ROI: 4.71%

Traditional ROI: 4.92%

13920 Sandy Oak Road

Chester, VA

4 beds | 3 baths | 2,200 sq.ft.

$389,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.25%

Airbnb Rental Income: $null

Traditional Rental Income: $2657

Airbnb ROI: N/A

Traditional ROI: 5.25%

1831 Galley Place

Chester, VA

4 beds | 3 baths | 2,811 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2869

Airbnb ROI: N/A