Real Estate Investment Properties for Sale in Chesterfield, VA

Looking for investment property in Chesterfield, VA with high ROI ?

Explore a variety of short-term homes & houses in Chesterfield, VA. Invest wisely with VRBO & Chesterfield, 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 Chesterfield, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12605 Long Branch Court Chesterfield, VA THIS UPDATED RANCH BOASTS A FIRST FLOOR OWNERS SUITE WITH WALK IN CLOSET AND GARDEN TUB IN...	3 beds \| 2 baths \| 1,928 sq.ft.	$419,999	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.75% Airbnb Rental Income: $3068 Traditional Rental Income: $2259 Airbnb ROI: 4.03% Traditional ROI: 3.75%
6639 Cyrus Street Chesterfield, VA Welcome home to this beautifully remodeled 4-bedroom, 3 full bath Cape Cod nestled in a cu...	4 beds \| 3 baths \| 1,659 sq.ft.	$340,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 6.07% Airbnb Rental Income: $3781 Traditional Rental Income: $2556 Airbnb ROI: 7.34% Traditional ROI: 6.07%
10750 Trailwood Drive Chesterfield, VA Welcome to Trailwood Drive, a charming and renovated home nestled in the beautiful Quail H...	3 beds \| 3 baths \| 1,506 sq.ft.	$369,950	Airbnb cash on cash: 4.94% Traditional cash on cash: 4.64% Airbnb Rental Income: $3068 Traditional Rental Income: $2262 Airbnb ROI: 4.94% Traditional ROI: 4.64%
3131 Ghent Drive Chesterfield, VA Welcome home to 3131 Ghent Drive-this charming and well-maintained ranch-style home offers...	3 beds \| 2 baths \| 1,412 sq.ft.	$319,950	Airbnb cash on cash: 5.74% Traditional cash on cash: 4.53% Airbnb Rental Income: $3068 Traditional Rental Income: $2003 Airbnb ROI: 5.74% Traditional ROI: 4.53%
4415 Cara Hill Lane Chesterfield, VA Well Maintained & Move-In Ready in Chester! Welcome to this beautifully cared-for 4-bedroo...	4 beds \| 3 baths \| 2,082 sq.ft.	$400,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 4.96% Airbnb Rental Income: $3781 Traditional Rental Income: $2612 Airbnb ROI: 5.89% Traditional ROI: 4.96%
5616 Heatherhill Drive Chesterfield, VA Price Reduced.......Split Level 4 Bedroom, 2 Full baths! Great Location! Large laundry roo...	4 beds \| 2 baths \| 1,688 sq.ft.	$269,999	Airbnb cash on cash: 9.33% Traditional cash on cash: 7.08% Airbnb Rental Income: $3781 Traditional Rental Income: $2389 Airbnb ROI: 9.33% Traditional ROI: 7.08%
5325 Meadoway Road Chesterfield, VA Welcome to 5325 Meadoway Rd. a 3 bedroom, 1.5 baths rancher. Some of the highlights are: -...	3 beds \| 2 baths \| 1,821 sq.ft.	$385,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.8% Airbnb Rental Income: $3068 Traditional Rental Income: $2413 Airbnb ROI: 4.67% Traditional ROI: 4.8%
13830 Crosstimbers Road Chesterfield, VA Welcome to 13830 Crosstimbers Road, a beautifully maintained Colonial in the heart of Bran...	4 beds \| 3 baths \| 1,814 sq.ft.	$399,995	Airbnb cash on cash: 5.92% Traditional cash on cash: 5.26% Airbnb Rental Income: $3781 Traditional Rental Income: $2715 Airbnb ROI: 5.92% Traditional ROI: 5.26%
4337 Brixton Rd Chesterfield, VA Completely renovated and move-in ready! This spacious 4-bedroom, 3-bath home offers over 2...	4 beds \| 3 baths \| N/A	$420,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 5.63% Airbnb Rental Income: $3781 Traditional Rental Income: $2973 Airbnb ROI: 5.6% Traditional ROI: 5.63%
5313 Sandy Ridge Court Chesterfield, VA Better than new in Brown's Bluff at Colony Pointe. Welcome to your only 6 year old home in...	4 beds \| 3 baths \| 1,944 sq.ft.	$437,500	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.52% Airbnb Rental Income: $3781 Traditional Rental Income: $2645 Airbnb ROI: 5.3% Traditional ROI: 4.52%
10426 White Rabbit Road Chesterfield, VA Welcome to 10426 White Rabbit Road in North Chesterfield! Tucked away in the North Settler...	3 beds \| 3 baths \| 1,938 sq.ft.	$409,950	Airbnb cash on cash: 4.24% Traditional cash on cash: 4.68% Airbnb Rental Income: $3068 Traditional Rental Income: $2538 Airbnb ROI: 4.24% Traditional ROI: 4.68%
9165 Chatham Grove Lane Chesterfield, VA This is your chance to own a home in the Fernbrook neighborhood! This beautiful transition...	3 beds \| 3 baths \| 1,996 sq.ft.	$370,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 5.47% Airbnb Rental Income: $3068 Traditional Rental Income: $2631 Airbnb ROI: 4.71% Traditional ROI: 5.47%
8101 Darebin Place Chesterfield, VA Welcome to this stunning 4-bed, 2.5-bath newer-build craftsman that checks every box! Styl...	4 beds \| 3 baths \| 2,895 sq.ft.	$515,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 4.42% Airbnb Rental Income: $3781 Traditional Rental Income: $3042 Airbnb ROI: 4.25% Traditional ROI: 4.42%
19501 Walker Avenue Chesterfield, VA Welcome Home to 19501 Walker Ave. This home is an amazing opportunity for home ownership o...	3 beds \| 2 baths \| 1,080 sq.ft.	$209,000	Airbnb cash on cash: 9.65% Traditional cash on cash: 6.85% Airbnb Rental Income: $3068 Traditional Rental Income: $1814 Airbnb ROI: 9.65% Traditional ROI: 6.85%
16731 Amherst Oak Lane Chesterfield, VA BACK ON THE MARKET - NO FAULT OF THE SELLER!! Motivated Seller offers up to $8000 toward b...	4 beds \| 3 baths \| 1,751 sq.ft.	$345,000	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.12% Airbnb Rental Income: $3781 Traditional Rental Income: $2321 Airbnb ROI: 7.1% Traditional ROI: 5.12%
7000 Autumn Point Drive Chesterfield, VA Welcome to this beautifully maintained 2-story single-family home, ideally located in the ...	3 beds \| 3 baths \| 1,800 sq.ft.	$380,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.99% Airbnb Rental Income: $3068 Traditional Rental Income: $2137 Airbnb ROI: 4.63% Traditional ROI: 3.99%
7705 Offshore Drive Chesterfield, VA Step inside to this adorable 2-story cottage! Perfectly nestled in the highly sought-after...	3 beds \| 2 baths \| 1,334 sq.ft.	$324,950	Airbnb cash on cash: 5.74% Traditional cash on cash: 4.24% Airbnb Rental Income: $3068 Traditional Rental Income: $1907 Airbnb ROI: 5.74% Traditional ROI: 4.24%
3800 Grizzard Dr Chesterfield, VA Welcome home to this charming and move-in ready ranch at 3800 Grizzard Drive. Tucked away ...	3 beds \| 1 baths \| N/A	$299,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 3.98% Airbnb Rental Income: $3068 Traditional Rental Income: $1688 Airbnb ROI: 6.39% Traditional ROI: 3.98%
2217 Courthouse Road Chesterfield, VA Lovely 3 bedroom, 1.5 bath, classic brick rancher conveniently located on Courthouse Road....	3 beds \| 2 baths \| 1,425 sq.ft.	$309,900	Airbnb cash on cash: 6.1% Traditional cash on cash: 5.13% Airbnb Rental Income: $3068 Traditional Rental Income: $2086 Airbnb ROI: 6.1% Traditional ROI: 5.13%
149 N Courthouse Road Chesterfield, VA PROPERTY HAS COMMERCIAL POTENTIAL. OVER 4 ACRES ON COURTHOUSE ROAD. OLDER HOME NEEDS FULL ...	2 beds \| 1 baths \| 1,080 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $1398 Airbnb ROI: N/A Traditional ROI: 2.79%
4241 Daniels Street Chesterfield, VA 4241 Daniels Street in Chester Va. will be perfect you and your family!! This home offers ...	3 beds \| 3 baths \| 2,055 sq.ft.	$369,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 5.08% Airbnb Rental Income: $3068 Traditional Rental Income: $2484 Airbnb ROI: 4.75% Traditional ROI: 5.08%
10306 Lifford Lane Chesterfield, VA Welcome Home! Enter the oversized Great Room with bay window and LVP flooring! Open to the...	4 beds \| 2 baths \| 1,380 sq.ft.	$319,950	Airbnb cash on cash: 7.76% Traditional cash on cash: 4.83% Airbnb Rental Income: $3781 Traditional Rental Income: $2079 Airbnb ROI: 7.76% Traditional ROI: 4.83%
6784 Arbor Meadows Drive Chesterfield, VA Welcome Home! Step into charm and comfort as you enter the formal dining room, where rich ...	4 beds \| 4 baths \| 2,408 sq.ft.	$429,950	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.85% Airbnb Rental Income: $3781 Traditional Rental Income: $2790 Airbnb ROI: 5.28% Traditional ROI: 4.85%
10700 Trailwood Drive Chesterfield, VA Welcome to 10700 Trailwood Drive-a stately all-brick saltbox home nestled on a beautifully...	4 beds \| 3 baths \| 1,899 sq.ft.	$389,999	Airbnb cash on cash: 6.13% Traditional cash on cash: 5.08% Airbnb Rental Income: $3781 Traditional Rental Income: $2578 Airbnb ROI: 6.13% Traditional ROI: 5.08%
15631 Corte Castle Terrace Chesterfield, VA Welcome to 15631 Corte Castle Terrace. Located in a quiet, desirable neighborhood with acc...	4 beds \| 3 baths \| 2,043 sq.ft.	$449,995	Airbnb cash on cash: 5.02% Traditional cash on cash: 4.04% Airbnb Rental Income: $3781 Traditional Rental Income: $2550 Airbnb ROI: 5.02% Traditional ROI: 4.04%
11221 Rabbit Ridge Road Chesterfield, VA Welcome to the perfect blend of charm, comfort, and modern living. This beautifully renova...	5 beds \| 4 baths \| 3,489 sq.ft.	$675,000	Airbnb cash on cash: 9.92% Traditional cash on cash: 3.86% Airbnb Rental Income: $9136 Traditional Rental Income: $3606 Airbnb ROI: 9.92% Traditional ROI: 3.86%
19105 Braebrook Drive Chesterfield, VA Welcome to 19105 Braebrook! This charming ranch home is ready for new owners. Step inside ...	3 beds \| 1 baths \| 1,056 sq.ft.	$240,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 5.3% Airbnb Rental Income: $3068 Traditional Rental Income: $1701 Airbnb ROI: 8.24% Traditional ROI: 5.3%
2000 Lindell Road Chesterfield, VA Welcome to 2000 Lindell Road! This beautiful colonial offers everything you could want and...	4 beds \| 3 baths \| 2,482 sq.ft.	$475,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.23% Airbnb Rental Income: $3781 Traditional Rental Income: $2755 Airbnb ROI: 4.69% Traditional ROI: 4.23%
14718 Cobbs Point Drive Chesterfield, VA Improved Price*Say hello to this move in ready home located in Cobbs Point. This beaut...	4 beds \| 3 baths \| 2,076 sq.ft.	$374,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 5.01% Airbnb Rental Income: $3781 Traditional Rental Income: $2485 Airbnb ROI: 6.37% Traditional ROI: 5.01%
12618 Capernwray Terrace Chesterfield, VA Located in The Highlands community, this wonderful property sits on 2.7 private acres at t...	4 beds \| 5 baths \| 3,607 sq.ft.	$799,900	Airbnb cash on cash: 2.04% Traditional cash on cash: 4.13% Airbnb Rental Income: $3781 Traditional Rental Income: $4519 Airbnb ROI: 2.04% Traditional ROI: 4.13%
13625 Brandy Oaks Rd Chesterfield, VA Welcome to your dream home! This stunning 4-bedroom, 2.5-bathroom residence boasts a spaci...	4 beds \| 3 baths \| N/A	$585,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 3.01% Airbnb Rental Income: $3781 Traditional Rental Income: $2764 Airbnb ROI: 3.37% Traditional ROI: 3.01%
9507 Dunroming Road Chesterfield, VA Welcome to this beautifully maintained Colonial-style home located in the heart of Chester...	4 beds \| 3 baths \| 2,069 sq.ft.	$420,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 4.53% Airbnb Rental Income: $3781 Traditional Rental Income: $2582 Airbnb ROI: 5.5% Traditional ROI: 4.53%
4020 Ambergrove Ave Chesterfield, VA Nestled in the rolling hills of Chesterfield County is a small, idyllic community known as...	3 beds \| 3 baths \| N/A	$544,360	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.57% Airbnb Rental Income: $3068 Traditional Rental Income: $2328 Airbnb ROI: 2.65% Traditional ROI: 2.57%
18805 Pine Grove Avenue Chesterfield, VA Charming 3-bedroom, 2-bath ranch-style home in South Chesterfield. This single-level home ...	3 beds \| 2 baths \| 1,092 sq.ft.	$315,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 4.43% Airbnb Rental Income: $3068 Traditional Rental Income: $1897 Airbnb ROI: 6.02% Traditional ROI: 4.43%
5324 Sandy Ridge Court Chesterfield, VA Fantastic 4 Bedroom 2.5 Bathroom with attached garage home in Highly Desired part of Chest...	4 beds \| 3 baths \| 2,144 sq.ft.	$449,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.14% Airbnb Rental Income: $3781 Traditional Rental Income: $2580 Airbnb ROI: 5.05% Traditional ROI: 4.14%
11219 Parrish Creek Lane Chesterfield, VA Welcome to 11219 Parrish Creek Lane...nestled on a quiet cul-de-sac in the Clay Pointe nei...	4 beds \| 3 baths \| 1,800 sq.ft.	$400,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.69% Airbnb Rental Income: $3781 Traditional Rental Income: $2508 Airbnb ROI: 5.9% Traditional ROI: 4.69%
5700 Koufax Dr Chesterfield, VA Welcome home to 5700 Koufax in Chesterfield! This charming Cape Cod is ready to welcome it...	3 beds \| 3 baths \| N/A	$337,999	Airbnb cash on cash: 5.44% Traditional cash on cash: 6.2% Airbnb Rental Income: $3068 Traditional Rental Income: $2609 Airbnb ROI: 5.44% Traditional ROI: 6.2%
8603 Boones Bluff Mews Chesterfield, VA This fantastic Cape Cod has the outdoor feel of being secluded in the woods yet inside is ...	3 beds \| 2 baths \| 1,540 sq.ft.	$365,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 4.6% Airbnb Rental Income: $3068 Traditional Rental Income: $2271 Airbnb ROI: 4.89% Traditional ROI: 4.6%
615 Pumpkin Pl Chesterfield, VA Welcome home to 615 Pumpkin Pl., in Harvest Glen. This three bedroom home was built by Eag...	3 beds \| 2 baths \| N/A	$469,950	Airbnb cash on cash: 3.36% Traditional cash on cash: 2.71% Airbnb Rental Income: $3068 Traditional Rental Income: $2082 Airbnb ROI: 3.36% Traditional ROI: 2.71%
5500 Jessup Road Chesterfield, VA This two-bedroom bungalow featuring a spacious, private yard, plus a detached garage and w...	2 beds \| 1 baths \| 950 sq.ft.	$140,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.4% Airbnb Rental Income: $null Traditional Rental Income: $1642 Airbnb ROI: N/A Traditional ROI: 9.4%

Real Estate investment in Chesterfield, VA

There are 316 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $429,975 and the average price per square foot is $190. In September 2025, the average monthly cash on cash return in Chesterfield is 4.00%. The average monthly rental income in Chesterfield is $2,583.

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

There are 316 investment properties available for sale in Chesterfield.

In 2025, the best neighborhood to buy investment property is Chesterfield.

The ROI for Short-Term is higher than the Long-Term in Chesterfield with average rental income of $3,781.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, VA

12605 Long Branch Court

Chesterfield, VA

3 beds | 2 baths | 1,928 sq.ft.

$419,999

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $3068

Traditional Rental Income: $2259

Airbnb ROI: 4.03%

Traditional ROI: 3.75%

6639 Cyrus Street

Chesterfield, VA

4 beds | 3 baths | 1,659 sq.ft.

$340,000

Airbnb cash on cash: 7.34%

Traditional cash on cash: 6.07%

Airbnb Rental Income: $3781

Traditional Rental Income: $2556

Airbnb ROI: 7.34%

Traditional ROI: 6.07%

10750 Trailwood Drive

Chesterfield, VA

3 beds | 3 baths | 1,506 sq.ft.

$369,950

Airbnb cash on cash: 4.94%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $3068

Traditional Rental Income: $2262

Airbnb ROI: 4.94%

Traditional ROI: 4.64%

3131 Ghent Drive

Chesterfield, VA

3 beds | 2 baths | 1,412 sq.ft.

$319,950

Airbnb cash on cash: 5.74%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3068

Traditional Rental Income: $2003

Airbnb ROI: 5.74%

Traditional ROI: 4.53%

4415 Cara Hill Lane

Chesterfield, VA

4 beds | 3 baths | 2,082 sq.ft.

$400,000

Airbnb cash on cash: 5.89%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $3781

Traditional Rental Income: $2612

Airbnb ROI: 5.89%

Traditional ROI: 4.96%

5616 Heatherhill Drive

Chesterfield, VA

4 beds | 2 baths | 1,688 sq.ft.

$269,999

Airbnb cash on cash: 9.33%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $3781

Traditional Rental Income: $2389

Airbnb ROI: 9.33%

Traditional ROI: 7.08%

5325 Meadoway Road

Chesterfield, VA

3 beds | 2 baths | 1,821 sq.ft.

$385,000

Airbnb cash on cash: 4.67%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $3068

Traditional Rental Income: $2413

Airbnb ROI: 4.67%

Traditional ROI: 4.8%

13830 Crosstimbers Road

Chesterfield, VA

4 beds | 3 baths | 1,814 sq.ft.

$399,995

Airbnb cash on cash: 5.92%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $3781

Traditional Rental Income: $2715

Airbnb ROI: 5.92%