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
700 Dove Path Lane Chester, VA Welcome to this Beautiful maintained home is truly move-in ready. Inside, you'll find hard...	4 beds \| 3 baths \| 2,382 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $2819 Airbnb ROI: N/A Traditional ROI: 4.96%
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.	$412,800	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 5.21%
5112 Beachmere Court Chester, VA Welcome home to the perfect blend of luxury, comfort, and thoughtful design. This beautifu...	4 beds \| 3 baths \| 2,810 sq.ft.	$510,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.76% Airbnb Rental Income: $null Traditional Rental Income: $3222 Airbnb ROI: N/A Traditional ROI: 4.76%
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: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $3733 Airbnb ROI: N/A Traditional ROI: 5.94%
2436 Old Bermuda Hundred Road Chester, VA Welcome to easy one-level living in Bermuda Place! This brick-and-vinyl ranch saves its be...	3 beds \| 2 baths \| 1,040 sq.ft.	$319,950	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.85% Airbnb Rental Income: $903 Traditional Rental Income: $1767 Airbnb ROI: -0.15% Traditional ROI: 3.85%
13401 Greenham Court Chester, VA Opportunity, location, and value come together in this inviting 3-bedroom, 2.5-bath home. ...	3 beds \| 3 baths \| 1,728 sq.ft.	$329,950	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.65% Airbnb Rental Income: $903 Traditional Rental Income: $2088 Airbnb ROI: -0.27% Traditional ROI: 4.65%
518 Greymont Lane Chester, VA Agent Remarks: Welcome to 518 Greymont Lane, a beautifully maintained custom home that...	4 beds \| 3 baths \| 2,776 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $2880 Airbnb ROI: N/A Traditional ROI: 3.87%
12337 Villas Dr Chester, VA Beautiful 2-story home featuring 4 spacious bedrooms and fresh paint throughout! This move...	4 beds \| 3 baths \| N/A	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 4.33%
3809 N Light Drive Chester, VA Welcome to 3908 N. Light Drive in the heart of Chester! This updated cape home is convenie...	4 beds \| 2 baths \| 1,440 sq.ft.	$324,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $2102 Airbnb ROI: N/A Traditional ROI: 4.78%
13506 Green Spire Court Chester, VA Cul-de-sac setting, open main level, and everyday convenience near major commuter routes. ...	4 beds \| 3 baths \| 2,154 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $2551 Airbnb ROI: N/A Traditional ROI: 4.49%
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.	$401,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 4.98%
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.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $3097 Airbnb ROI: N/A Traditional ROI: 2.88%
9749 Hoke Brady Road Chester, VA Exceptionally unique in every way, this custom home checks all the boxes. Walk to the Rive...	4 beds \| 4 baths \| 3,600 sq.ft.	$969,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.47% Airbnb Rental Income: $null Traditional Rental Income: $2991 Airbnb ROI: N/A Traditional ROI: 1.47%
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: -0.15% Traditional cash on cash: 2.02% Airbnb Rental Income: $903 Traditional Rental Income: $1596 Airbnb ROI: -0.15% Traditional ROI: 2.02%
4537 Wellington Farms Dr Chester, VA BRING YOUR OFFERS NOW...PRICED BELOW 2026 ASSESSMENT!!! This stunning all-brick home offer...	4 beds \| 4 baths \| N/A	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $3384 Airbnb ROI: N/A Traditional ROI: 3.85%
5431 W Hundred Road Chester, VA Welcome to 5431 W. Hundred Rd. - a beautifully renovated retreat sitting on a full acre of...	2 beds \| 1 baths \| 864 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.62% Airbnb Rental Income: $null Traditional Rental Income: $1401 Airbnb ROI: N/A Traditional ROI: 3.62%
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%
1731 Galley Place Chester, VA Welcome to 1731 in Twin Rivers, one of Chester's most desirable James River waterfront com...	3 beds \| 2 baths \| 1,712 sq.ft.	$460,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.42% Airbnb Rental Income: $903 Traditional Rental Income: $2524 Airbnb ROI: -1.14% Traditional ROI: 3.42%
4508 Edenton Place Chester, VA Tucked away in a quiet pocket of Chester's Greenbriar neighborhood, this thoughtfully upda...	4 beds \| 2 baths \| 1,788 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.71% Airbnb Rental Income: $null Traditional Rental Income: $2468 Airbnb ROI: N/A Traditional ROI: 4.71%
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: -0.9% Traditional cash on cash: 0.56% Airbnb Rental Income: $903 Traditional Rental Income: $2598 Airbnb ROI: -0.9% Traditional ROI: 0.56%
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.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $1795 Airbnb ROI: N/A Traditional ROI: 3.93%
4325 Poplar Village Dr Chester, VA Welcome to 4325 Poplar Village Dr in Poplar Village! This beautiful 4-bedroom, 2-bath ranc...	4 beds \| 2 baths \| N/A	$517,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $2350 Airbnb ROI: N/A Traditional ROI: 3.44%
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%
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.	$949,950	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $3292 Airbnb ROI: N/A Traditional ROI: 1.98%
9537 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.	$579,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $3091 Airbnb ROI: N/A Traditional ROI: 3.72%
1801 Galley Place Chester, VA Welcome to Twin Rivers at Meadowville Landing-where resort-style living meets low-maintena...	3 beds \| 3 baths \| 1,695 sq.ft.	$439,900	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.59% Airbnb Rental Income: $903 Traditional Rental Income: $2431 Airbnb ROI: -0.94% Traditional ROI: 3.59%
4248 Poplar Village Drive Chester, VA UNDER CONSTRUCTION with SUMMER DELIVERY! Meet the Albany, 2963 sq ft, 4 bedrooms, 3.5 bath...	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 THIS BEAUTIFUL 3446 SQFT HOME IN LAKEWOOD FARMS BOASTS A NEW 15 SEER CARRIER DUAL FUEL HVA...	4 beds \| 3 baths \| 3,446 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $3265 Airbnb ROI: N/A Traditional ROI: 4.92%
4313 Poplar Village Drive Chester, VA NEW PHOTOS: See inside the MOVE IN READY Potomac Farmhouse! Welcome to your dream home! Th...	5 beds \| 3 baths \| 2,624 sq.ft.	$534,733	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $2841 Airbnb ROI: N/A Traditional ROI: 4.38%
5301 Krag Road Chester, VA Welcome to this beautifully crafted Westley Burton home, where quality and attention to de...	5 beds \| 5 baths \| 3,840 sq.ft.	$499,950	Airbnb cash on cash: N/A Traditional cash on cash: 8.04% Airbnb Rental Income: $null Traditional Rental Income: $4755 Airbnb ROI: N/A Traditional ROI: 8.04%
11900 James Overlook Court Chester, VA Rare opportunity in Chesterfield County! This beautifully designed 4-bedroom home offers T...	4 beds \| 4 baths \| 3,184 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $3537 Airbnb ROI: N/A Traditional ROI: 3.97%
12606 Poplar Village Place Chester, VA NEW PICTURES! MOVE IN READY NEW CONSTRUCTION! The STAFFORD is just over 2,500 sq/ft of pur...	4 beds \| 3 baths \| 2,505 sq.ft.	$524,119	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $2826 Airbnb ROI: N/A Traditional ROI: 4.46%
10624 Rosies Run Chester, VA HOMESITE SPECIAL - SUMMER MOVE-IN! Time your move perfectly with great summer weather and ...	3 beds \| 3 baths \| N/A	$349,990	Airbnb cash on cash: -5.76% Traditional cash on cash: -0.44% Airbnb Rental Income: $903 Traditional Rental Income: $2315 Airbnb ROI: -5.76% Traditional ROI: -0.44%
9556 Fuchsia Drive Chester, VA The Essex model offers a spacious open-concept living space, ideal for modern living and e...	3 beds \| 3 baths \| 1,333 sq.ft.	$419,990	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.17% Airbnb Rental Income: $903 Traditional Rental Income: $2153 Airbnb ROI: -0.87% Traditional ROI: 3.17%
10642 Pink Lily Ln Chester, VA MOST PRIVATE LOCATION IN THE COMMUNITY! Your home backs up to trees, offering tons of priv...	3 beds \| 3 baths \| N/A	$359,990	Airbnb cash on cash: -5.63% Traditional cash on cash: -0.45% Airbnb Rental Income: $903 Traditional Rental Income: $2315 Airbnb ROI: -5.63% Traditional ROI: -0.45%
16111 Happy Hill Road Chester, VA REDUCED 5K.....Rural Living at it's Best! Make this 3 Bedroom 2 Bath Rancher Your Own* Sit...	3 beds \| 2 baths \| 1,300 sq.ft.	$294,900	Airbnb cash on cash: 0.01% Traditional cash on cash: 4.38% Airbnb Rental Income: $903 Traditional Rental Income: $1777 Airbnb ROI: 0.01% Traditional ROI: 4.38%
9553 Fuchsia Drive Chester, VA Introducing the Galen model, offering a modern and spacious open-concept living space perf...	4 beds \| 3 baths \| 2,340 sq.ft.	$471,740	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2086 Airbnb ROI: N/A Traditional ROI: 2.47%
10612 Rosies Run Chester, VA SPECIAL PRICING - SUMMER MOVE-IN! Time your move perfectly with great summer weather and b...	3 beds \| 3 baths \| N/A	$349,990	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.49% Airbnb Rental Income: $903 Traditional Rental Income: $2330 Airbnb ROI: -0.89% Traditional ROI: 4.49%
1713 Mainsail Ln Chester, VA Welcome to 1713 Mainsail Ln in Twin Rivers, a James River front community offering an exce...	3 beds \| 3 baths \| N/A	$449,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 3.19% Airbnb Rental Income: $903 Traditional Rental Income: $2390 Airbnb ROI: -1.16% Traditional ROI: 3.19%
10637 Pink Lily Ln Chester, VA SUMMER MOVE-IN! Time your move perfectly with great summer weather and before the school y...	3 beds \| 3 baths \| N/A	$349,990	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.46% Airbnb Rental Income: $903 Traditional Rental Income: $2323 Airbnb ROI: -0.89% Traditional ROI: 4.46%

Real Estate investment in Chester, VA

There are 103 properties for sale in the city of Chester . The median list price in Chester is $379,800 and the average price per square foot is $169. In June 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,524.

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

There are 103 investment properties available for sale in Chester.

In 2026, 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 $903.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VA

700 Dove Path Lane

Chester, VA

4 beds | 3 baths | 2,382 sq.ft.

$430,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2819

Airbnb ROI: N/A

Traditional ROI: 4.96%

3924 Belspring Road

Chester, VA

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

$412,800

Airbnb cash on cash: N/A

Traditional cash on cash: 5.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2785

Airbnb ROI: N/A

Traditional ROI: 5.21%

5112 Beachmere Court

Chester, VA

4 beds | 3 baths | 2,810 sq.ft.

$510,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.76%

Airbnb Rental Income: $null

Traditional Rental Income: $3222

Airbnb ROI: N/A

Traditional ROI: 4.76%

4237 Wells Ridge Court

Chester, VA

4 beds | 4 baths | 2,878 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.94%

Airbnb Rental Income: $null

Traditional Rental Income: $3733

Airbnb ROI: N/A

Traditional ROI: 5.94%

2436 Old Bermuda Hundred Road

Chester, VA

3 beds | 2 baths | 1,040 sq.ft.

$319,950

Airbnb cash on cash: -0.15%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $903

Traditional Rental Income: $1767

Airbnb ROI: -0.15%

Traditional ROI: 3.85%

13401 Greenham Court

Chester, VA

3 beds | 3 baths | 1,728 sq.ft.

$329,950

Airbnb cash on cash: -0.27%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $903

Traditional Rental Income: $2088

Airbnb ROI: -0.27%

Traditional ROI: 4.65%

518 Greymont Lane

Chester, VA

4 beds | 3 baths | 2,776 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2880

Airbnb ROI: N/A

Traditional ROI: 3.87%

12337 Villas Dr

Chester, VA

4 beds | 3 baths | N/A

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2754

Airbnb ROI: N/A