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
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%
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%
12600 Inverness Drive Chester, VA Tucked away on a quiet cul-de-sac, this beautifully maintained brick home offers timeless ...	3 beds \| 3 baths \| 2,803 sq.ft.	$585,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.96% Airbnb Rental Income: $528 Traditional Rental Income: $2679 Airbnb ROI: -1.49% Traditional ROI: 2.96%
11542 Chester Station Dr Chester, VA Welcome to this thoughtfully renovated retreat offers the perfect blend of modern luxury, ...	2 beds \| 2 baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.48% Airbnb Rental Income: $null Traditional Rental Income: $1763 Airbnb ROI: N/A Traditional ROI: 3.48%
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.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2819 Airbnb ROI: N/A Traditional ROI: 4.77%
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: -1.46% Traditional cash on cash: 4.8% Airbnb Rental Income: $528 Traditional Rental Income: $2394 Airbnb ROI: -1.46% Traditional ROI: 4.8%
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.	$415,800	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 5.17%
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%
14510 Alberta Court Chester, VA Discover the timeless charm of this stunning 3000 square foot French Provincial home, perf...	4 beds \| 4 baths \| 3,008 sq.ft.	$553,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $3366 Airbnb ROI: N/A Traditional ROI: 4.53%
13601 Ramblewood Drive Chester, VA Charming Cape Cod situated on nearly 3/4 of an acre offering space, privacy, and exterior ...	3 beds \| 2 baths \| 1,344 sq.ft.	$319,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 4.09% Airbnb Rental Income: $528 Traditional Rental Income: $1813 Airbnb ROI: -1.12% Traditional ROI: 4.09%
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%
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	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 4.22%
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.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 4.72%
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%
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: -0.8% Traditional cash on cash: 2.02% Airbnb Rental Income: $528 Traditional Rental Income: $1596 Airbnb ROI: -0.8% Traditional ROI: 2.02%
10460 Shumark Dr Chester, VA Welcome to 10460 Shumark Drive, a charming home where thoughtful design and inviting outdo...	3 beds \| 3 baths \| N/A	$399,900	Airbnb cash on cash: -1.32% Traditional cash on cash: 4.17% Airbnb Rental Income: $528 Traditional Rental Income: $2311 Airbnb ROI: -1.32% Traditional ROI: 4.17%
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%
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: -1.46% Traditional cash on cash: 4.5% Airbnb Rental Income: $528 Traditional Rental Income: $2762 Airbnb ROI: -1.46% 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%
1731 Galley Place Chester, VA Remarks: Welcome to 1731, a like-new home in Twin Rivers, one of Chester's most sought-aft...	3 beds \| 2 baths \| 1,712 sq.ft.	$475,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 3.28% Airbnb Rental Income: $528 Traditional Rental Income: $2524 Airbnb ROI: -1.84% Traditional ROI: 3.28%
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: -1.39% Traditional cash on cash: 4.84% Airbnb Rental Income: $528 Traditional Rental Income: $2551 Airbnb ROI: -1.39% 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: -1.12% Traditional cash on cash: 0.56% Airbnb Rental Income: $528 Traditional Rental Income: $2598 Airbnb ROI: -1.12% 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.	$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%
14101 Ramsey Ct Chester, VA ""NEED A TURNKEY HOME...THIS IS THE ONE!!! NEW DIMENSIONAL ROOF - 2024 NEW HVAC (gas fu...	5 beds \| 3 baths \| N/A	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $2774 Airbnb ROI: N/A Traditional ROI: 5.25%
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%
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.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3035 Airbnb ROI: N/A Traditional ROI: 4.64%
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%
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: -1.69% Traditional cash on cash: 3.55% Airbnb Rental Income: $528 Traditional Rental Income: $2785 Airbnb ROI: -1.69% Traditional ROI: 3.55%
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 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: -1.7% Traditional cash on cash: 3.59% Airbnb Rental Income: $528 Traditional Rental Income: $2431 Airbnb ROI: -1.7% Traditional ROI: 3.59%
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.	$430,640	Airbnb cash on cash: -1.42% Traditional cash on cash: 3.01% Airbnb Rental Income: $528 Traditional Rental Income: $2040 Airbnb ROI: -1.42% Traditional ROI: 3.01%
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%
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.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.72% Airbnb Rental Income: $null Traditional Rental Income: $4755 Airbnb ROI: N/A Traditional ROI: 7.72%
10631 Rosies Run Chester, VA SUMMER MOVE-IN! Start your summer the right way with this brand-new END UNIT home availabl...	3 beds \| 3 baths \| N/A	$368,990	Airbnb cash on cash: -1.36% Traditional cash on cash: 4.76% Airbnb Rental Income: $528 Traditional Rental Income: $2370 Airbnb ROI: -1.36% Traditional ROI: 4.76%
10613 Rosies Run Chester, VA SUMMER MOVE-IN! Start your summer the right way with this brand-new home available at Wrex...	3 beds \| 3 baths \| N/A	$346,990	Airbnb cash on cash: -1.33% Traditional cash on cash: 5.17% Airbnb Rental Income: $528 Traditional Rental Income: $2370 Airbnb ROI: -1.33% Traditional ROI: 5.17%

Real Estate investment in Chester, VA

There are 117 properties for sale in the city of Chester . The median list price in Chester is $424,975 and the average price per square foot is $181. In May 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,551.

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

There are 117 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 $2,551.

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%

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%

12600 Inverness Drive

Chester, VA

3 beds | 3 baths | 2,803 sq.ft.

$585,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $528

Traditional Rental Income: $2679

Airbnb ROI: -1.49%

Traditional ROI: 2.96%

11542 Chester Station Dr

Chester, VA

2 beds | 2 baths | N/A

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.48%

Airbnb Rental Income: $null

Traditional Rental Income: $1763

Airbnb ROI: N/A

Traditional ROI: 3.48%

700 Dove Path Lane

Chester, VA

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

$445,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.77%

Airbnb Rental Income: $null

Traditional Rental Income: $2819

Airbnb ROI: N/A

Traditional ROI: 4.77%

4613 Crossgate Road

Chester, VA

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

$365,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $528

Traditional Rental Income: $2394

Airbnb ROI: -1.46%

Traditional ROI: 4.8%

3924 Belspring Road

Chester, VA

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

$415,800

Airbnb cash on cash: N/A

Traditional cash on cash: 5.17%

Airbnb Rental Income: $null

Traditional Rental Income: $2785

Airbnb ROI: N/A