Real Estate Investment Properties for Sale in Dillwyn, VA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1353 BANTON SHOP RD Dillwyn, VA Nestled in the heart of nature, this exceptional 119-acre estate offers over a mile of Sla...	4 beds \| 3 baths \| 2,887 sq.ft.	$1,390,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $3108 Airbnb ROI: N/A Traditional ROI: 1.11%
3359 S Constitution Route Dillwyn, VA Discover 3 +/- acres offering a duplex and a singlewide home - ideal for owner-occupiers, ...	N/A beds \| N/A baths \| 1,524 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $1922 Airbnb ROI: N/A Traditional ROI: 7.43%
1024 Back Mountain Road Dillwyn, VA Tucked away on 21 private acres in Dillwyn with creek frontage, this home offers a life th...	3 beds \| 3 baths \| 2,928 sq.ft.	$680,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2932 Airbnb ROI: N/A Traditional ROI: 3.24%
74 Conner St Dillwyn, VA Price Reduced ! Spacious home, Large shop, and garden space on corner lot in Dillwyn, VA. ...	4 beds \| 2 baths \| 2,204 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.26% Airbnb Rental Income: $null Traditional Rental Income: $2285 Airbnb ROI: N/A Traditional ROI: 6.26%
3814 S Constitution Dillwyn, VA 43 ac farm of open and nicely wooded property with timber value. Great location not far fr...	3 beds \| 2 baths \| 1,536 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.63% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 2.63%
3814 S Constitution Rte Dillwyn, VA 3814 S Constitution Rte, Dillwyn, VA 23936 \| Single Family Residential	3 beds \| 1 baths \| 1,536 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $1461 Airbnb ROI: N/A Traditional ROI: 1.11%
0 N James Madison Hwy Dillwyn, VA 0 N James Madison Hwy, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $517 Airbnb ROI: N/A Traditional ROI: 2.56%
221 Brickyard Dr Dillwyn, VA 221 Brickyard Dr, Dillwyn, VA 23936 \| Multi Family	N/A beds \| N/A baths \| 50,000 sq.ft.	$4,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.64% Airbnb Rental Income: $null Traditional Rental Income: $807 Airbnb ROI: N/A Traditional ROI: -1.64%
N James Madison Hwy Dillwyn, VA N James Madison Hwy, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $807 Airbnb ROI: N/A Traditional ROI: 0.94%
Allen Rosen Rd Dillwyn, VA Allen Rosen Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$274,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $807 Airbnb ROI: N/A Traditional ROI: 0.94%
3331 S CONSTITUTION RTE Dillwyn, VA Location, Location! Welcome to this delightful ranch home, nestled on a generous and l...	3 beds \| 2 baths \| 1,956 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $2143 Airbnb ROI: N/A Traditional ROI: 5.62%
3331 S Constitution Dillwyn, VA Location, Location! Welcome to this delightful ranch home, nestled on a generous and l...	3 beds \| 2 baths \| 1,956 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.42% Airbnb Rental Income: $null Traditional Rental Income: $2082 Airbnb ROI: N/A Traditional ROI: 5.42%
Buckingham Centre Dr Dillwyn, VA Buckingham Centre Dr, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.38% Airbnb Rental Income: $null Traditional Rental Income: $563 Airbnb ROI: N/A Traditional ROI: -0.38%
State Hwy. 15 (tract: Tonguequarter) Dillwyn, VA State Hwy. 15 (tract: Tonguequarter), Buckingham, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.29% Airbnb Rental Income: $null Traditional Rental Income: $797 Airbnb ROI: N/A Traditional ROI: -0.29%
1237 Main St Dillwyn, VA 1237 Main St, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 0.8%
1236 Main St Dillwyn, VA 1236 Main St, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 0.8%
1 Maple Bridge Rd Dillwyn, VA 1 Maple Bridge Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 1.11%
3B Maple Bridge Rd Dillwyn, VA 3B Maple Bridge Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 3.35%
3A Maple Bridge Rd Dillwyn, VA 3A Maple Bridge Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$129,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 2.19%
169 OLD DARBYTOWN RD Dillwyn, VA Charming Country Living on Nearly an Acre in Dillwyn, VA Welcome to peaceful country livi...	3 beds \| 2 baths \| N/A	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.32% Airbnb Rental Income: $null Traditional Rental Income: $1747 Airbnb ROI: N/A Traditional ROI: 8.32%
3271 Rosney Dillwyn, VA Welcome to this first-time-offered, solid brick three bedroom two bath home full of timele...	3 beds \| 2 baths \| 1,935 sq.ft.	$342,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $1746 Airbnb ROI: N/A Traditional ROI: 3.84%
3271 Rosney Rd Dillwyn, VA 3271 Rosney Rd, Dillwyn, VA 23936 \| Single Family Residential	3 beds \| 2 baths \| 1,935 sq.ft.	$342,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.18% Airbnb Rental Income: $null Traditional Rental Income: $1699 Airbnb ROI: N/A Traditional ROI: 3.18%
116.32 Acres Gilliam Mill Rd Dillwyn, VA 116.32 Acres Gilliam Mill Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$299,950	Airbnb cash on cash: N/A Traditional cash on cash: -0.05% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: -0.05%
20 South Constitution Dillwyn, VA 20 South Constitution, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 1.46%
0 Sanders Creek Rd Dillwyn, VA 0 Sanders Creek Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$112,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.77% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 2.77%
0.73 Ac James Madison Hwy N Dillwyn, VA 0.73 Ac James Madison Hwy N, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 3.31%
2026 BANTON SHOP RD Dillwyn, VA Welcome home to this spacious 4-bedroom, 2-bath residence nestled on approximately 6 beaut...	4 beds \| 2 baths \| 1,725 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 5.09%
2664 S Constitution Route Dillwyn, VA New Construction by Rock River Homes. Estimated completion July 2026! This Laurel Creek fl...	3 beds \| 2 baths \| 1,358 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $1724 Airbnb ROI: N/A Traditional ROI: 3.76%
89 Johnson Station Rd Dillwyn, VA 89 Johnson Station Rd, Dillwyn, VA 23936 \| Single Family Residential	3 beds \| 2 baths \| 1,690 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $1548 Airbnb ROI: N/A Traditional ROI: 2.95%
3897 Gravel Hill Rd Dillwyn, VA 3897 Gravel Hill Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$35,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.45% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 11.45%
Bell Road (tract: Moore North) Dillwyn, VA Bell Road (tract: Moore North), Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$1,781,262	Airbnb cash on cash: N/A Traditional cash on cash: -1.51% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: -1.51%
XX N James Madison Hwy Dillwyn, VA XX N James Madison Hwy, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.01% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: -1.01%
28 Hunters Lane Dillwyn, VA .Charming Remodeled Cape Cod on a Beautiful Acre Lot!Welcome home to this beautifully remo...	4 beds \| 2 baths \| 1,440 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.78% Airbnb Rental Income: $null Traditional Rental Income: $1956 Airbnb ROI: N/A Traditional ROI: 5.78%
1487 Spencer Road Dillwyn, VA Solidly built and designed for practical country living, this custom bungalow sits at the ...	2 beds \| 1 baths \| 800 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $1541 Airbnb ROI: N/A Traditional ROI: 4.16%
1451 Dixie Hill Road Dillwyn, VA Welcome to 1451 Dixie Hill Road, where country living meets modern comfort on an incredibl...	3 beds \| 1 baths \| 1,512 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $1548 Airbnb ROI: N/A Traditional ROI: 1.7%
9 Ac Childress Rd Dillwyn, VA 9 Ac Childress Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$57,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.78% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 6.78%
0 Chellowe Rd Dillwyn, VA 0 Chellowe Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$499,950	Airbnb cash on cash: N/A Traditional cash on cash: -0.75% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: -0.75%
Slate River Mill Rd Dillwyn, VA	N/A beds \| N/A baths \| N/A	$90,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 3.83%
9 Ac Childress Dillwyn, VA 9 Ac Childress, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$57,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.78% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 6.78%
3286 Ranson Rd Dillwyn, VA Spacious, open, inviting, and just for you! You'll find Like New 1500 sq foot home with me...	3 beds \| 2 baths \| 1,508 sq.ft.	$334,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $1933 Airbnb ROI: N/A Traditional ROI: 4.03%

Real Estate investment in Dillwyn, VA

There are 43 properties for sale in the city of Dillwyn . The median list price in Dillwyn is $192,000 and the average price per square foot is $60. In July 2026, the average monthly cash on cash return in Dillwyn is 3.00%. The average monthly rental income in Dillwyn is $807.

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

There are 43 investment properties available for sale in Dillwyn.

The ROI for Short-Term is higher than the Long-Term in Dillwyn with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Dillwyn, VA

1353 BANTON SHOP RD

Dillwyn, VA

4 beds | 3 baths | 2,887 sq.ft.

$1,390,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.11%

Airbnb Rental Income: $null

Traditional Rental Income: $3108

Airbnb ROI: N/A

Traditional ROI: 1.11%

3359 S Constitution Route

Dillwyn, VA

N/A beds | N/A baths | 1,524 sq.ft.

$215,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.43%

Airbnb Rental Income: $null

Traditional Rental Income: $1922

Airbnb ROI: N/A

Traditional ROI: 7.43%

1024 Back Mountain Road

Dillwyn, VA

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

$680,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2932

Airbnb ROI: N/A

Traditional ROI: 3.24%

74 Conner St

Dillwyn, VA

4 beds | 2 baths | 2,204 sq.ft.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2285

Airbnb ROI: N/A

Traditional ROI: 6.26%

3814 S Constitution

Dillwyn, VA

3 beds | 2 baths | 1,536 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.63%

Airbnb Rental Income: $null

Traditional Rental Income: $1900

Airbnb ROI: N/A

Traditional ROI: 2.63%

3814 S Constitution Rte

Dillwyn, VA

3 beds | 1 baths | 1,536 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.11%

Airbnb Rental Income: $null

Traditional Rental Income: $1461

Airbnb ROI: N/A

Traditional ROI: 1.11%

0 N James Madison Hwy

Dillwyn, VA

N/A beds | N/A baths | 0 sq.ft.

$99,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $517

Airbnb ROI: N/A

Traditional ROI: 2.56%

221 Brickyard Dr

Dillwyn, VA

N/A beds | N/A baths | 50,000 sq.ft.

$4,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.64%

Airbnb Rental Income: $null

Traditional Rental Income: $807

Airbnb ROI: N/A