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
15806 Wind Seeker Ct Chester, VA Welcome to this well-maintained 3-bedroom, 2.5-bath home located on a quiet cul-de-sac in ...	3 beds \| 2 baths \| 1,585 sq.ft.	$375,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.1% Airbnb Rental Income: $1556 Traditional Rental Income: $2160 Airbnb ROI: 1.11% Traditional ROI: 4.1%
11901 Warfield Estates Drive Chester, VA Welcome to 11901 Warfield Estates Drive, where timeless charm meets beautifully updated in...	4 beds \| 3 baths \| 2,014 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $2558 Airbnb ROI: N/A Traditional ROI: 4.54%
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%
4329 Village Creek Dr Chester, VA There are homes buyers like and then there are homes buyers emotionally attach themselves ...	4 beds \| 2 baths \| 2,876 sq.ft.	$449,950	Airbnb cash on cash: 0.04% Traditional cash on cash: 4.26% Airbnb Rental Income: $1568 Traditional Rental Income: $2894 Airbnb ROI: 0.04% Traditional ROI: 4.26%
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%
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: 2.29% Traditional cash on cash: 3.85% Airbnb Rental Income: $1784 Traditional Rental Income: $1767 Airbnb ROI: 2.29% Traditional ROI: 3.85%
4512 Wraywood Ave Chester, VA Charming Brick Rancher with Full Basement and In-Law Suite Potential Welcome home to this ...	4 beds \| 3 baths \| 2,733 sq.ft.	$430,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2755 Airbnb ROI: N/A Traditional ROI: 4.84%
13413 Bradley Bridge Road Chester, VA Meticulously maintained and thoughtfully updated, this exceptional 3-bedroom ranch offers ...	3 beds \| 2 baths \| 2,726 sq.ft.	$550,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.4% Airbnb Rental Income: $1784 Traditional Rental Income: $2292 Airbnb ROI: 0.46% Traditional ROI: 2.4%
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: 2.1% Traditional cash on cash: 4.65% Airbnb Rental Income: $1784 Traditional Rental Income: $2088 Airbnb ROI: 2.1% 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 Back on the market at no fault of sellers. Beautiful 2-story home featuring 4 spacious bed...	4 beds \| 2 baths \| 2,445 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 4.39%
13506 Green Spire Court Chester, VA Quickly back on market, no fault to either party.... Cul-de-sac setting, open main level, ...	4 beds \| 3 baths \| 2,154 sq.ft.	$398,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $2551 Airbnb ROI: N/A Traditional ROI: 4.79%
2937 Abbeydale Ct Chester, VA Welcome to this beautiful four-bedroom home nestled in the heart of Chester! Situated on a...	4 beds \| 2 baths \| 2,392 sq.ft.	$393,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 5.09%
1520 Rustling Cedar Ln Chester, VA Nestled on 2.76 private acres in Henrico County, 1520 Rustling Cedar Lane offers a rare bl...	4 beds \| 3 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: 1.39% Traditional cash on cash: 2.02% Airbnb Rental Income: $1784 Traditional Rental Income: $1596 Airbnb ROI: 1.39% 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%
2720 Osborne Rd Chester, VA Welcome to this charming Cape Cod, where timeless character and modern updates come togeth...	3 beds \| 2 baths \| 1,352 sq.ft.	$339,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.88% Airbnb Rental Income: $1784 Traditional Rental Income: $2262 Airbnb ROI: 1.94% Traditional ROI: 4.88%
11938 Sternwalk Ct Chester, VA Welcome to the charming community of Meadowville Landing! This highly sought after neighbo...	5 beds \| 4 baths \| N/A	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $3454 Airbnb ROI: N/A Traditional ROI: 3.76%
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.	$521,361	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2575 Airbnb ROI: N/A Traditional ROI: 3.26%
4508 Edenton Pl 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 Rd Chester, VA Prime 35.87-Acre Development Opportunity - Heart of Chester, VA! Exceptional opportunity t...	3 beds \| 3 baths \| 2,376 sq.ft.	$1,499,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.56% Airbnb Rental Income: $1784 Traditional Rental Income: $2598 Airbnb ROI: -0.37% Traditional ROI: 0.56%
13624 Thornhill Pl Chester, VA Welcome home to this beautifully updated, move-in-ready residence in the highly desirable ...	4 beds \| 2 baths \| 1,946 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2595 Airbnb ROI: N/A Traditional ROI: 4.31%
2723 Goyne Ter Chester, VA Your Private Oasis Awaits! This impeccably maintained townhome offers the perfect blend of...	2 beds \| 2 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 \| 2,258 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $2350 Airbnb ROI: N/A Traditional ROI: 3.5%
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 Ct Chester, VA Refined elegance meets modern comfort in this stately custom-built home, featuring 4 spaci...	4 beds \| 2 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%
305 Redbird Drive Chester, VA Immaculately maintained and full of character, this GEORGIAN-INSPIRED gem at 305 Redbird D...	5 beds \| 4 baths \| 2,892 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $3243 Airbnb ROI: N/A Traditional ROI: 3.98%
12151 Calgary Loop Chester, VA Experience the Picasso plan, a luxury townhome-style condo with over 2,200 sq ft designed ...	3 beds \| 2 baths \| 2,208 sq.ft.	$389,900	Airbnb cash on cash: -2.3% Traditional cash on cash: 2.13% Airbnb Rental Income: $1919 Traditional Rental Income: $3030 Airbnb ROI: -2.3% Traditional ROI: 2.13%
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 Pl 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: 0.84% Traditional cash on cash: 3.59% Airbnb Rental Income: $1784 Traditional Rental Income: $2431 Airbnb ROI: 0.84% Traditional ROI: 3.59%
4248 Poplar Village Dr Chester, VA UNDER CONSTRUCTION with SUMMER DELIVERY! Meet the Albany, 2963 sq ft, 4 bedrooms, 3.5 bath...	4 beds \| 3 baths \| 2,963 sq.ft.	$574,340	Airbnb cash on cash: N/A Traditional cash on cash: 1.67% Airbnb Rental Income: $null Traditional Rental Income: $1963 Airbnb ROI: N/A Traditional ROI: 1.67%
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 Dr 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 "This home has been lovingly maintained and offers solid bones, spacious rooms, and a fant...	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%
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: -3.53% Traditional cash on cash: -0.44% Airbnb Rental Income: $1784 Traditional Rental Income: $2315 Airbnb ROI: -3.53% 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: 0.99% Traditional cash on cash: 3.17% Airbnb Rental Income: $1784 Traditional Rental Income: $2153 Airbnb ROI: 0.99% 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 \| 2 baths \| 1,567 sq.ft.	$359,990	Airbnb cash on cash: -3.46% Traditional cash on cash: -0.45% Airbnb Rental Income: $1784 Traditional Rental Income: $2315 Airbnb ROI: -3.46% Traditional ROI: -0.45%

Real Estate investment in Chester, VA

There are 147 properties for sale in the city of Chester . The median list price in Chester is $379,719 and the average price per square foot is $175. In August 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,506.

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

There are 147 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 $2,506.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VA

15806 Wind Seeker Ct

Chester, VA

3 beds | 2 baths | 1,585 sq.ft.

$375,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $1556

Traditional Rental Income: $2160

Airbnb ROI: 1.11%

Traditional ROI: 4.1%

11901 Warfield Estates Drive

Chester, VA

4 beds | 3 baths | 2,014 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.54%

Airbnb Rental Income: $null

Traditional Rental Income: $2558

Airbnb ROI: N/A

Traditional ROI: 4.54%

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%

4329 Village Creek Dr

Chester, VA

4 beds | 2 baths | 2,876 sq.ft.

$449,950

Airbnb cash on cash: 0.04%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $1568

Traditional Rental Income: $2894

Airbnb ROI: 0.04%

Traditional ROI: 4.26%

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%

2436 Old Bermuda Hundred Road

Chester, VA

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

$319,950

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1784

Traditional Rental Income: $1767

Airbnb ROI: 2.29%

Traditional ROI: 3.85%

4512 Wraywood Ave

Chester, VA

4 beds | 3 baths | 2,733 sq.ft.

$430,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2755

Airbnb ROI: N/A