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

separator

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%
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%
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%
12137 Perdue Springs Loop Chester, VA Welcome to 12137 Perdue Springs Loop, a charming and contemporary townhouse built in 2020,...	3 beds \| 3 baths \| 1,360 sq.ft.	$287,500	Airbnb cash on cash: 5.94% Traditional cash on cash: 4.8% Airbnb Rental Income: $3022 Traditional Rental Income: $2021 Airbnb ROI: 5.94% Traditional ROI: 4.8%
3709 Stardown Court Chester, VA *New and Improved Price!!*Don't miss this gorgeous home!! This home has been remodeled...	4 beds \| 2 baths \| 2,188 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.82% Airbnb Rental Income: $null Traditional Rental Income: $2411 Airbnb ROI: N/A Traditional ROI: 5.82%
11555 Claimont Mill Drive Chester, VA Come enjoy your new home in the heart of Chester. This Townhouse is an end unit and has pl...	3 beds \| 3 baths \| 1,864 sq.ft.	$350,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 4.04% Airbnb Rental Income: $3022 Traditional Rental Income: $2226 Airbnb ROI: 4.35% Traditional ROI: 4.04%
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.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $2246 Airbnb ROI: N/A Traditional ROI: 5.24%
3005 Cicero Parkway Chester, VA Welcome to your newly renovated tri-level home in Chester! Step inside to discover a brigh...	4 beds \| 2 baths \| 1,624 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2214 Airbnb ROI: N/A Traditional ROI: 4.61%
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%
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%
4066 Tanner Slip Cir Chester, VA Welcome home to 4066 Tanner Slip Circle located in the neighborhood of Harrowgate Place. S...	4 beds \| 3 baths \| N/A	$369,950	Airbnb cash on cash: N/A Traditional cash on cash: 5.13% Airbnb Rental Income: $null Traditional Rental Income: $2489 Airbnb ROI: N/A Traditional ROI: 5.13%
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 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%
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%
13101 Harrowgate Road Chester, VA The seller just improved the price again. The price has been lowered to 419k. They are als...	4 beds \| 3 baths \| 2,525 sq.ft.	$419,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.48% Airbnb Rental Income: $null Traditional Rental Income: $3283 Airbnb ROI: N/A Traditional ROI: 6.48%
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.	$369,900	Airbnb cash on cash: 4.88% Traditional cash on cash: 3.78% Airbnb Rental Income: $3022 Traditional Rental Income: $1946 Airbnb ROI: 4.88% Traditional ROI: 3.78%
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 the buyer's financing. This lovely 3-bedroom, 2-full-bath ranche...	3 beds \| 2 baths \| N/A	$314,900	Airbnb cash on cash: 5.78% Traditional cash on cash: 5.97% Airbnb Rental Income: $3022 Traditional Rental Income: $2385 Airbnb ROI: 5.78% 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: 6.52% Traditional cash on cash: 4.11% Airbnb Rental Income: $5396 Traditional Rental Income: $3091 Airbnb ROI: 6.52% 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%
12100 Ganesh Lane Chester, VA Luxury Live Auction! List price is based on opening bid. Seller will accept offers prior t...	4 beds \| 5 baths \| 6,085 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $5544 Airbnb ROI: N/A Traditional ROI: 3.98%
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 \| 2,020 sq.ft.	$543,940	Airbnb cash on cash: 2.8% Traditional cash on cash: 2.58% Airbnb Rental Income: $3022 Traditional Rental Income: $2220 Airbnb ROI: 2.8% Traditional ROI: 2.58%
4218 Poplar Village Drive Chester, VA PRICE IMPROVEMENT! NEW CONSTRUCTION! Estimated OCTOBER completion! The ROWLAND is an intri...	3 beds \| 3 baths \| 1,870 sq.ft.	$432,450	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.87% Airbnb Rental Income: $3022 Traditional Rental Income: $2407 Airbnb ROI: 3.68% Traditional ROI: 3.87%
12612 Poplar Village Place Chester, VA Meet The Cordova- the 5+ bedroom home you have been looking for. Upon entry, a flex room o...	5 beds \| 3 baths \| 2,599 sq.ft.	$465,304	Airbnb cash on cash: 7.84% Traditional cash on cash: 4.62% Airbnb Rental Income: $5396 Traditional Rental Income: $2902 Airbnb ROI: 7.84% Traditional ROI: 4.62%
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: 5.44% Traditional cash on cash: 5.89% Airbnb Rental Income: $5396 Traditional Rental Income: $4573 Airbnb ROI: 5.44% Traditional ROI: 5.89%
4319 Poplar Village Drive Chester, VA PRICE IMPROVEMENT - New Construction - 30 day close. The STAFFORD is just over 2,500 sq/ft...	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%
12189 Calgary Loop Chester, VA THIS IS AN END HOME - READY AUGUST 2025! Welcome to Moore's Lake - Garage Condos in Cheste...	3 beds \| 3 baths \| N/A	$359,990	Airbnb cash on cash: 4.8% Traditional cash on cash: 6.36% Airbnb Rental Income: $3022 Traditional Rental Income: $2857 Airbnb ROI: 4.8% Traditional ROI: 6.36%
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: 4.72% Traditional cash on cash: 7.44% Airbnb Rental Income: $5396 Traditional Rental Income: $6058 Airbnb ROI: 4.72% Traditional ROI: 7.44%
3000 Perdue Springs Lane Chester, VA Welcome to this bright and beautifully refreshed 3-story end unit townhouse featuring 3 sp...	3 beds \| 3 baths \| 1,920 sq.ft.	$309,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 5.15% Airbnb Rental Income: $3022 Traditional Rental Income: $2288 Airbnb ROI: 5.29% Traditional ROI: 5.15%
4201 Poplar Village Drive Chester, VA Welcome Home! As you walk in through the large covered stoop, you come across your spaciou...	3 beds \| 3 baths \| 2,072 sq.ft.	$475,122	Airbnb cash on cash: 3.19% Traditional cash on cash: 3.62% Airbnb Rental Income: $3022 Traditional Rental Income: $2518 Airbnb ROI: 3.19% Traditional ROI: 3.62%
12613 Poplar Village Place Chester, VA PRICE IMPROVEMENT - New Construction - 30 day close! The POTOMAC is just over 2,600 sq/ft ...	5 beds \| 3 baths \| 2,624 sq.ft.	$521,911	Airbnb cash on cash: 6.82% Traditional cash on cash: 4.02% Airbnb Rental Income: $5396 Traditional Rental Income: $2938 Airbnb ROI: 6.82% Traditional ROI: 4.02%
13308 Bermuda Place Drive Chester, VA Welcome to this beautiful 2 story Dutch Colonial with split entry situated on the edge of ...	3 beds \| 2 baths \| 1,964 sq.ft.	$330,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 5.27% Airbnb Rental Income: $3022 Traditional Rental Income: $2239 Airbnb ROI: 5.56% Traditional ROI: 5.27%
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.	$332,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 5.22% Airbnb Rental Income: $3022 Traditional Rental Income: $2443 Airbnb ROI: 4.85% Traditional ROI: 5.22%
13637 Laketree Drive Chester, VA This tastefully remodeled 5-bedroom, 2.5-bathroom home in the heart of Chester is the perf...	5 beds \| 3 baths \| 2,567 sq.ft.	$399,500	Airbnb cash on cash: 9.31% Traditional cash on cash: 5.26% Airbnb Rental Income: $5396 Traditional Rental Income: $2791 Airbnb ROI: 9.31% Traditional ROI: 5.26%
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%

Real Estate investment in Chester, VA

There are 111 properties for sale in the city of Chester . The median list price in Chester is $432,720 and the average price per square foot is $184. In October 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,686.

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

There are 111 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%

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%

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%

12137 Perdue Springs Loop

Chester, VA

3 beds | 3 baths | 1,360 sq.ft.

$287,500

Airbnb cash on cash: 5.94%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $3022

Traditional Rental Income: $2021

Airbnb ROI: 5.94%

Traditional ROI: 4.8%

3709 Stardown Court

Chester, VA

4 beds | 2 baths | 2,188 sq.ft.

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.82%

Airbnb Rental Income: $null

Traditional Rental Income: $2411

Airbnb ROI: N/A

Traditional ROI: 5.82%

11555 Claimont Mill Drive

Chester, VA

3 beds | 3 baths | 1,864 sq.ft.

$350,000

Airbnb cash on cash: 4.35%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $3022

Traditional Rental Income: $2226

Airbnb ROI: 4.35%

Traditional ROI: 4.04%

2804 Mimi Avenue

Chester, VA

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

$330,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2246

Airbnb ROI: N/A

Traditional ROI: 5.24%

3005 Cicero Parkway

Chester, VA

4 beds | 2 baths | 1,624 sq.ft.

$360,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2214

Airbnb ROI: N/A