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
Perkins Mill Rd Dillwyn, VA Perkins Mill Rd, Dillwyn, VA 23901 \| Other	N/A beds \| N/A baths \| N/A	$574,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.03% Airbnb Rental Income: $null Traditional Rental Income: $512 Airbnb ROI: N/A Traditional ROI: -1.03%
1971 Mount Rush Hwy Dillwyn, VA Well maintained Brick Ranch with unfinished terrace level for future expansion or storage....	3 beds \| 1 baths \| 1,325 sq.ft.	$140,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $1284 Airbnb ROI: N/A Traditional ROI: 7.28%
3286 Ranson Rd Dillwyn, VA Spacious, open, inviting, and just for you! On a mostly wooded lot you'll find a 1500 sq f...	3 beds \| 2 baths \| 1,508 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $1933 Airbnb ROI: N/A Traditional ROI: 3.95%
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.	$1,490,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $3108 Airbnb ROI: N/A Traditional ROI: 0.97%
594 Community Road Dillwyn, VA Ready for its new owner!! Discover modern comfort in this beautifully crafted 3-bedroom, 2...	3 beds \| 2 baths \| 1,620 sq.ft.	$349,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $1921 Airbnb ROI: N/A Traditional ROI: 4.53%
TBD S Constitution Rte Dillwyn, VA elcome to your dream home, nestled in the heart of Buckingham County! This beautifully des...	3 beds \| 2 baths \| 1,358 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.38% Airbnb Rental Income: $null Traditional Rental Income: $2095 Airbnb ROI: N/A Traditional ROI: -0.38%
1024 Back Mountain Rd 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.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2932 Airbnb ROI: N/A Traditional ROI: 3.03%
74 Conner St Dillwyn, VA Spacious home, large shop, and garden space on corner lot in Dillwyn, VA. Over 2200 sq ft,...	4 beds \| 2 baths \| 2,204 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.83% Airbnb Rental Income: $null Traditional Rental Income: $2285 Airbnb ROI: N/A Traditional ROI: 5.83%
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 \| N/A	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.3% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 2.3%
1002 Main St Dillwyn, VA Unique opportunity to live and work in the heart of Dillwyn, VA. This beautifully renovate...	4 beds \| 2 baths \| 3,452 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.19% Airbnb Rental Income: $null Traditional Rental Income: $1302 Airbnb ROI: N/A Traditional ROI: 1.19%
3814 S Constitution Rte Dillwyn, VA 3814 S Constitution Rte, Dillwyn, VA 23936 \| Single Family Residential	3 beds \| 1 baths \| 1,536 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.85% Airbnb Rental Income: $null Traditional Rental Income: $1461 Airbnb ROI: N/A Traditional ROI: 0.85%
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.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.72% Airbnb Rental Income: $null Traditional Rental Income: $807 Airbnb ROI: N/A Traditional ROI: 0.72%
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.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $2143 Airbnb ROI: N/A Traditional ROI: 5.07%
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.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $2082 Airbnb ROI: N/A Traditional ROI: 4.88%
Physic Spg Dillwyn, VA Physic Spg, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.28% Airbnb Rental Income: $null Traditional Rental Income: $512 Airbnb ROI: N/A Traditional ROI: 8.28%
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%
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: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $832 Airbnb ROI: N/A Traditional ROI: 2.08%
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: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $832 Airbnb ROI: N/A Traditional ROI: 2.53%
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%
2B Sanders Creek Rd Dillwyn, VA 2B Sanders Creek 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%
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 \| 1,024 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.63% Airbnb Rental Income: $null Traditional Rental Income: $1747 Airbnb ROI: N/A Traditional ROI: 7.63%
7139 Andersonville Rd Dillwyn, VA 3.5 Acres \| Unrestricted Land \| Large Garage Opportunity meets flexibility with this 3-be...	3 beds \| 2 baths \| 924 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.81% Airbnb Rental Income: $null Traditional Rental Income: $1889 Airbnb ROI: N/A Traditional ROI: 11.81%
S Constitution Route Dillwyn, VA OPEN-CONCEPT 3-BEDROOM, 2-BATH HOME ON 5 PRIVATE ACRES IN BUCKINGHAM COUNTY! This Laurel C...	3 beds \| 2 baths \| 1,358 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $1867 Airbnb ROI: N/A Traditional ROI: 4.02%
3271 Rosney Dillwyn, VA Welcome to this first-time-offered, solid brick three bedroom two bath home full of timele...	3 beds \| 2 baths \| N/A	$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%
41 SEAYS DR Dillwyn, VA Spacious Manor Home On Almost 4 Acres In Historic Dillwyn VA!! The Main House Features 5 B...	5 beds \| 3 baths \| 3,396 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $3105 Airbnb ROI: N/A Traditional ROI: 6.22%
41 Seays Dillwyn, VA Spacious Manor Home On Almost 4 Acres In Historic Dillwyn VA!! The Main House Features 5 B...	5 beds \| 3 baths \| 2,596 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $2998 Airbnb ROI: N/A Traditional ROI: 5.94%
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: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $1284 Airbnb ROI: N/A Traditional ROI: 1.89%
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	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.19% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: -0.19%
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	$119,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 2.48%
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%
1.4 Ac Physic Spring Rd Dillwyn, VA 1.4 Ac Physic Spring Rd, Dillwyn, VA 23936 \| Other	N/A beds \| N/A baths \| N/A	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.15% Airbnb Rental Income: $null Traditional Rental Income: $590 Airbnb ROI: N/A Traditional ROI: 10.15%
63 Wood Yard Road Dillwyn, VA OPEN-CONCEPT 3-BEDROOM, 2-BATH HOME ON 3 PRIVATE ACRES IN BUCKINGHAM COUNTY! This Laurel C...	3 beds \| 2 baths \| 1,358 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 4.07%
392 Rock Creek Lane Dillwyn, VA Charming 3-bedroom cape nestled in the country on 7 beautiful acres! This home features an...	3 beds \| 3 baths \| 1,456 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $1920 Airbnb ROI: N/A Traditional ROI: 4.66%

Real Estate investment in Dillwyn, VA

There are 39 properties for sale in the city of Dillwyn . The median list price in Dillwyn is $325,000 and the average price per square foot is $91. In May 2026, the average monthly cash on cash return in Dillwyn is 4.00%. The average monthly rental income in Dillwyn is $1,284.

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

There are 39 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

Perkins Mill Rd

Dillwyn, VA

N/A beds | N/A baths | N/A

$574,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.03%

Airbnb Rental Income: $null

Traditional Rental Income: $512

Airbnb ROI: N/A

Traditional ROI: -1.03%

1971 Mount Rush Hwy

Dillwyn, VA

3 beds | 1 baths | 1,325 sq.ft.

$140,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1284

Airbnb ROI: N/A

Traditional ROI: 7.28%

3286 Ranson Rd

Dillwyn, VA

3 beds | 2 baths | 1,508 sq.ft.

$339,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.95%

Airbnb Rental Income: $null

Traditional Rental Income: $1933

Airbnb ROI: N/A

Traditional ROI: 3.95%

1353 Banton Shop Rd

Dillwyn, VA

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

$1,490,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.97%

Airbnb Rental Income: $null

Traditional Rental Income: $3108

Airbnb ROI: N/A

Traditional ROI: 0.97%

594 Community Road

Dillwyn, VA

3 beds | 2 baths | 1,620 sq.ft.

$349,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.53%

Airbnb Rental Income: $null

Traditional Rental Income: $1921

Airbnb ROI: N/A

Traditional ROI: 4.53%

TBD S Constitution Rte

Dillwyn, VA

3 beds | 2 baths | 1,358 sq.ft.

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: -0.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2095

Airbnb ROI: N/A

Traditional ROI: -0.38%

1024 Back Mountain Rd

Dillwyn, VA

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

$715,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.03%

Airbnb Rental Income: $null

Traditional Rental Income: $2932

Airbnb ROI: N/A

Traditional ROI: 3.03%

74 Conner St

Dillwyn, VA

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

$329,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2285

Airbnb ROI: N/A