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
3200 Sylvania Place Chester, VA Beautifully Renovated Cape with Country Charm! This stunning home welcomes you with a full...	4 beds \| 2 baths \| 1,512 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $2199 Airbnb ROI: N/A Traditional ROI: 4.73%
1637 Forest Glenn Circle Chester, VA Charming 3-Bedroom Brick Rancher in Prime Enon/Chester Location! Welcome home to this spac...	3 beds \| 3 baths \| 2,225 sq.ft.	$389,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.62% Airbnb Rental Income: $1427 Traditional Rental Income: $2429 Airbnb ROI: 0.71% Traditional ROI: 4.62%
4212 Poplar Village Drive Chester, VA NEW CONSTRUCTION WITH EARLY APRIL DELIVERY! NO HOA! Meet The CORDOVA with CRAFTSMAN elevat...	5 beds \| 4 baths \| 2,970 sq.ft.	$536,822	Airbnb cash on cash: 3.29% Traditional cash on cash: 5.38% Airbnb Rental Income: $2991 Traditional Rental Income: $3356 Airbnb ROI: 3.29% Traditional ROI: 5.38%
12324 Windsor Rd Chester, VA A timeless classic ranch with exceptional space and charm in the heart of Chester! This lo...	5 beds \| 3 baths \| 3,464 sq.ft.	$444,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 5.56% Airbnb Rental Income: $2991 Traditional Rental Income: $3170 Airbnb ROI: 3.51% Traditional ROI: 5.56%
3831 Wood Dale Rd Chester, VA BACK ON THE MARKET DUE TO BUYERS FINANCING FALLING THRU AGAIN. This lovely 3-bedroom, 2-f...	4 beds \| 2 baths \| N/A	$314,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 5.97%
14149 Enon Station Ter Chester, VA This Brand-New Home is Ready Now! Call today to schedule your tour! Welcome to Enon Stati...	3 beds \| 3 baths \| N/A	$434,990	Airbnb cash on cash: 0.37% Traditional cash on cash: 4.9% Airbnb Rental Income: $1427 Traditional Rental Income: $2849 Airbnb ROI: 0.37% Traditional ROI: 4.9%
1509 Enon Church Rd Hopewell, VA This charming ranch-style home in the Forest Glenn neighborhood is ready to welcome its ne...	3 beds \| 1 baths \| 864 sq.ft.	$220,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 5.76% Airbnb Rental Income: $912 Traditional Rental Income: $1666 Airbnb ROI: 0.5% Traditional ROI: 5.76%
10624 Rosies Run Chester, VA HOMESITE SPECIAL - SUMMER MOVE-IN! Time your move perfectly with great summer weather and ...	3 beds \| 2 baths \| 1,567 sq.ft.	$349,990	Airbnb cash on cash: -4.43% Traditional cash on cash: -0.44% Airbnb Rental Income: $1427 Traditional Rental Income: $2315 Airbnb ROI: -4.43% Traditional ROI: -0.44%
10419 Centralia Station Rd Chester, VA Charming 4-Bedroom Home in a Peaceful Suburban Chesterfield Neighborhood Welcome to yo...	4 beds \| 2 baths \| 2,424 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 3.82%
12060 Almer Ln Chester, VA Why wait to build when you can have this now? Located in The Landings at Meadowville-Chest...	3 beds \| 2 baths \| 2,490 sq.ft.	$510,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.05% Airbnb Rental Income: $1427 Traditional Rental Income: $2965 Airbnb ROI: -0.07% Traditional ROI: 4.05%
3219 Castlebury Dr Chester, VA Updates throughout including New Flooring on the main level and new carpet on the second f...	3 beds \| 2 baths \| 1,777 sq.ft.	$379,993	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.77% Airbnb Rental Income: $1427 Traditional Rental Income: $2402 Airbnb ROI: 0.83% Traditional ROI: 4.77%
2820 Euphoria Rd Chester, VA Welcome to 2820 Euphoria Rd in Chester! This classic two-story traditional home offers ove...	4 beds \| 2 baths \| 3,053 sq.ft.	$415,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 4.8% Airbnb Rental Income: $870 Traditional Rental Income: $2728 Airbnb ROI: -0.7% Traditional ROI: 4.8%
5301 Krag Rd Chester, VA Welcome to this beautifully crafted Westley Burton home, where quality and attention to de...	5 beds \| 4 baths \| 3,840 sq.ft.	$519,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 7.72% Airbnb Rental Income: $2991 Traditional Rental Income: $4755 Airbnb ROI: 2.66% Traditional ROI: 7.72%
12607 Poplar Village Pl Chester, VA NEW IMPROVED PRICE!! MOVE IN READY, NEW CONSTRUCTION WITH BASEMENT! NO HOA! Meet The ROWLA...	5 beds \| 3 baths \| 2,910 sq.ft.	$524,950	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.28% Airbnb Rental Income: $2991 Traditional Rental Income: $3091 Airbnb ROI: 2.67% Traditional ROI: 4.28%
11325 Vulcan Ln Chester, VA Welcome home to this better than new Move-In Ready - Bramante Floor Plan built in 2024! En...	3 beds \| 2 baths \| 1,595 sq.ft.	$414,950	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.2% Airbnb Rental Income: $1427 Traditional Rental Income: $2136 Airbnb ROI: 0.28% Traditional ROI: 3.2%
2840 Calgary Ln Chester, VA Have you seen the Picasso? This luxury townhome style condo lives like a single-family ho...	3 beds \| 2 baths \| 2,617 sq.ft.	$399,270	Airbnb cash on cash: -3.85% Traditional cash on cash: 1.73% Airbnb Rental Income: $1427 Traditional Rental Income: $3041 Airbnb ROI: -3.85% Traditional ROI: 1.73%
10906 Timonium Dr 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.	$359,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.91% Airbnb Rental Income: $1427 Traditional Rental Income: $1946 Airbnb ROI: 1.11% Traditional ROI: 3.91%
10600 Rosies Run Chester, VA END UNIT - SUMMER MOVE-IN! Time your move perfectly with great summer weather and before t...	3 beds \| 2 baths \| 1,567 sq.ft.	$376,990	Airbnb cash on cash: -4.2% Traditional cash on cash: -0.47% Airbnb Rental Income: $1427 Traditional Rental Income: $2315 Airbnb ROI: -4.2% Traditional ROI: -0.47%
11900 James Overlook Ct Chester, VA PRICED REDUCED! MOTIVATED SELLERS! Welcome to Meadowville Landing! This beautifully appoin...	4 beds \| 3 baths \| 3,184 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3537 Airbnb ROI: N/A Traditional ROI: 3.82%
1801 Galley Pl Chester, VA Welcome to beautiful Twin Rivers at Meadowville Landing where landscaping is taken care of...	3 beds \| 3 baths \| 1,695 sq.ft.	$455,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.39% Airbnb Rental Income: $1427 Traditional Rental Income: $2431 Airbnb ROI: 0.07% Traditional ROI: 3.39%
11416 Claimont Mill Dr Chester, VA Welcome to 11416 Claimont Drive - Built in 2021! Almost brand new! A beautifully maintaine...	3 beds \| 2 baths \| 1,716 sq.ft.	$359,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 4.54% Airbnb Rental Income: $1427 Traditional Rental Income: $2412 Airbnb ROI: 0.37% Traditional ROI: 4.54%
13443 Greenham Ct Chester, VA Located in the highly desirable community of The Village of Long Meadow, is this beautiful...	5 beds \| 2 baths \| 2,140 sq.ft.	$399,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 5.03% Airbnb Rental Income: $4877 Traditional Rental Income: $2688 Airbnb ROI: 8.21% Traditional ROI: 5.03%
1512 Anchor Landing Dr Chester, VA Situated in the beautiful Meadowville Landing neighborhood, this 5 bedroom, 4 bathroom hou...	5 beds \| 4 baths \| 3,925 sq.ft.	$730,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 3.19% Airbnb Rental Income: $2991 Traditional Rental Income: $3566 Airbnb ROI: 1.34% Traditional ROI: 3.19%
12712 Dell Hill Ct Chester, VA Welcome to a truly exceptional, custom-built classic where timeless elegance meets modern ...	4 beds \| 3 baths \| 4,204 sq.ft.	$849,900	Airbnb cash on cash: -1.13% Traditional cash on cash: 1.68% Airbnb Rental Income: $870 Traditional Rental Income: $2757 Airbnb ROI: -1.13% Traditional ROI: 1.68%
12029 Almer Ln Chester, VA Welcome to one of Chesterfield's best kept secrets, The Landings at Meadowville! This prem...	5 beds \| 4 baths \| 4,268 sq.ft.	$695,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.29% Airbnb Rental Income: $2991 Traditional Rental Income: $3483 Airbnb ROI: 1.47% Traditional ROI: 3.29%
4608 Stoney Creek Pkwy Chester, VA PRICE REDUCED!!!!! Four Bedroom Colonial w/2.5 Baths & attached 2 car garage conveniently ...	4 beds \| 2 baths \| 2,096 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2418 Airbnb ROI: N/A Traditional ROI: 4.37%
12700 Dell Hill Ct Chester, VA Step into effortless elegance in this exquisite 2017 custom-built home, featuring 5-6 spac...	5 beds \| 3 baths \| 4,044 sq.ft.	$949,900	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.24% Airbnb Rental Income: $2991 Traditional Rental Income: $3562 Airbnb ROI: 0.81% Traditional ROI: 2.24%
6524 Bolles Landing Ct Chester, VA Welcome to this nearly brand-new townhome, built in 2023 and perfectly situated as a desir...	3 beds \| 2 baths \| 1,639 sq.ft.	$349,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.16% Airbnb Rental Income: $1427 Traditional Rental Income: $2221 Airbnb ROI: 0.44% Traditional ROI: 4.16%
4401 Village Garden Cir Chester, VA ALL BRICK 1.5 STORY HOME. Owners suite and 2nd bedroom on 1st floor. Walk right in to the ...	3 beds \| 3 baths \| 2,502 sq.ft.	$425,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.71% Airbnb Rental Income: $1427 Traditional Rental Income: $2516 Airbnb ROI: -0.09% Traditional ROI: 3.71%
3420 Osborne Rd Chester, VA Charming Colonial in the Heart of Chester! Welcome to this beautiful brick-front Colonial ...	3 beds \| 3 baths \| 3,270 sq.ft.	$519,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 4.42% Airbnb Rental Income: $1427 Traditional Rental Income: $3088 Airbnb ROI: 0.12% Traditional ROI: 4.42%
10618 Rosies Run Chester, VA SUMMER MOVE-IN! Time your move perfectly with great summer weather and before the school y...	3 beds \| 2 baths \| 1,567 sq.ft.	$356,990	Airbnb cash on cash: -4.38% Traditional cash on cash: -2.04% Airbnb Rental Income: $1427 Traditional Rental Income: $1781 Airbnb ROI: -4.38% Traditional ROI: -2.04%
12225 Twin Rivers Dr Chester, VA Step into luxury with this thoughtfully designed "Oasis" floor plan by HHHunt, with a 2-be...	2 beds \| 2 baths \| 2,041 sq.ft.	$559,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.34% Airbnb Rental Income: $1621 Traditional Rental Income: $1425 Airbnb ROI: -0.16% Traditional ROI: 0.34%
12606 Poplar Village Pl Chester, VA UNDER CONSTRUCTION, LATE APRIL DELIVERY! The STAFFORD is just over 2,500 sq/ft of pure lux...	4 beds \| 2 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%
4313 Poplar Village Dr Chester, VA UNDER CONSTRUCTION WITH EARLY APRIL DELIVERY! NO HOA! Meet The Potomac with a stunning Far...	5 beds \| 3 baths \| 2,624 sq.ft.	$534,733	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.38% Airbnb Rental Income: $2991 Traditional Rental Income: $2841 Airbnb ROI: 3.3% Traditional ROI: 4.38%
4248 Poplar Village Dr Chester, VA To Be Built. The Charles is a charming RANCH style home with 3 bedrooms and 2 baths. This ...	3 beds \| 2 baths \| 1,454 sq.ft.	$409,950	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.72% Airbnb Rental Income: $1427 Traditional Rental Income: $1963 Airbnb ROI: 0.87% Traditional ROI: 3.72%
5501 Buxton Ct Chester, VA WELCOME TO WATERFRONT VIEWS ON A LARGE CUL DE SAC, PARTIALLY WOODED LOT IN THE HEART OF CH...	4 beds \| 3 baths \| 3,446 sq.ft.	$534,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $3265 Airbnb ROI: N/A Traditional ROI: 4.53%
812 Bermuda Hundred Rd 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: 0.77% Traditional cash on cash: 2.02% Airbnb Rental Income: $1427 Traditional Rental Income: $1596 Airbnb ROI: 0.77% Traditional ROI: 2.02%
2620 Calgary Dr Chester, VA NEW FLOOR PLAN DESIGN - THE MONET! This condo at Moore's Lake offers spacious, maintenanc...	3 beds \| 2 baths \| 1,621 sq.ft.	$324,990	Airbnb cash on cash: -4.47% Traditional cash on cash: 2.19% Airbnb Rental Income: $1427 Traditional Rental Income: $3035 Airbnb ROI: -4.47% Traditional ROI: 2.19%

Real Estate investment in Chester, VA

There are 142 properties for sale in the city of Chester . The median list price in Chester is $415,000 and the average price per square foot is $190. In March 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,564.

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

There are 142 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 $2,564.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VA

3200 Sylvania Place

Chester, VA

4 beds | 2 baths | 1,512 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2199

Airbnb ROI: N/A

Traditional ROI: 4.73%

1637 Forest Glenn Circle

Chester, VA

3 beds | 3 baths | 2,225 sq.ft.

$389,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1427

Traditional Rental Income: $2429

Airbnb ROI: 0.71%

Traditional ROI: 4.62%

4212 Poplar Village Drive

Chester, VA

5 beds | 4 baths | 2,970 sq.ft.

$536,822

Airbnb cash on cash: 3.29%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $2991

Traditional Rental Income: $3356

Airbnb ROI: 3.29%

Traditional ROI: 5.38%

12324 Windsor Rd

Chester, VA

5 beds | 3 baths | 3,464 sq.ft.

$444,000

Airbnb cash on cash: 3.51%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $2991

Traditional Rental Income: $3170

Airbnb ROI: 3.51%

Traditional ROI: 5.56%

3831 Wood Dale Rd

Chester, VA

4 beds | 2 baths | N/A

$314,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A

Traditional ROI: 5.97%

14149 Enon Station Ter

Chester, VA

3 beds | 3 baths | N/A

$434,990

Airbnb cash on cash: 0.37%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1427

Traditional Rental Income: $2849

Airbnb ROI: 0.37%

Traditional ROI: 4.9%

1509 Enon Church Rd

Hopewell, VA

3 beds | 1 baths | 864 sq.ft.

$220,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 5.76%

Airbnb Rental Income: $912

Traditional Rental Income: $1666

Airbnb ROI: 0.5%

Traditional ROI: 5.76%

10624 Rosies Run

Chester, VA

3 beds | 2 baths | 1,567 sq.ft.

$349,990

Airbnb cash on cash: -4.43%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $1427

Traditional Rental Income: $2315

Airbnb ROI: -4.43%