Real Estate Investment Properties for Sale in Hillsboro, VA

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
36944 Charles Town Pike HILLSBORO, VA Located in the charming town of Hillsboro, this home provides the benefit of walkability i...	3 beds \| 2 baths \| 1,824 sq.ft.	$674,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 1.56% Airbnb Rental Income: $2507 Traditional Rental Income: $2056 Airbnb ROI: 1.32% Traditional ROI: 1.56%
13471 Sagle Rd HILLSBORO, VA Mountain views, open pastures, and 10 beautiful acres create the perfect Western Loudoun r...	4 beds \| 4 baths \| 3,590 sq.ft.	$1,320,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.2% Airbnb Rental Income: $2285 Traditional Rental Income: $3586 Airbnb ROI: -0.33% Traditional ROI: 1.2%
13855 Paris Breeze Pl HILLSBORO, VA Welcome to elegant, turnkey 13855 Paris Breeze Pl, your exclusive, private happy place. Cr...	3 beds \| 2 baths \| 2,166 sq.ft.	$1,115,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.37% Airbnb Rental Income: $2507 Traditional Rental Income: $2172 Airbnb ROI: 0.1% Traditional ROI: 0.37%
37275 Charles Town Pike HILLSBORO, VA THE MANN HOUSE - A RARE OPPORTUNITY ON 12 ACRES The Mann House is a 1740 log and stone est...	3 beds \| 2 baths \| 2,058 sq.ft.	$999,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.65% Airbnb Rental Income: $2507 Traditional Rental Income: $2115 Airbnb ROI: 0.42% Traditional ROI: 0.65%
14001 Harpers Ferry Rd HILLSBORO, VA 14001 Harpers Ferry Rd, HILLSBORO, VA 20132 \| Single Family Residential	5 beds \| 3 baths \| 8,612 sq.ft.	$7,500,000	Airbnb cash on cash: -1.38% Traditional cash on cash: -1.02% Airbnb Rental Income: $3940 Traditional Rental Income: $5627 Airbnb ROI: -1.38% Traditional ROI: -1.02%
37517 Bernardini Ct #21 HILLSBORO, VA 37517 Bernardini Ct #21, HILLSBORO, VA 20132 \| Single Family Residential	5 beds \| 5 baths \| 6,000 sq.ft.	$1,799,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.61% Airbnb Rental Income: $3940 Traditional Rental Income: $4258 Airbnb ROI: -0.08% Traditional ROI: 0.61%
11337 Russell Rd HILLSBORO, VA PRICE REDUCTION!! APPRAISAL REPORT CAME BACK AT 800K. MOTIVATED SELLER. COME CHECK IT OT. ...	4 beds \| 5 baths \| 2,928 sq.ft.	$779,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.34% Airbnb Rental Income: $2285 Traditional Rental Income: $3780 Airbnb ROI: 0.5% Traditional ROI: 3.34%
36660 HESKETT Lane HILLSBORO, VA Gorgeous homes in an idyllic setting - Welcome to The Ridges! 1-2 acre Home sites in the W...	4 beds \| 5 baths \| 5,200 sq.ft.	$1,595,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.02% Airbnb Rental Income: $2285 Traditional Rental Income: $2862 Airbnb ROI: -0.79% Traditional ROI: -0.02%
Stony Point Rd HILLSBORO, VA	N/A beds \| N/A baths \| 3,453 sq.ft.	$350,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.18% Airbnb Rental Income: $413 Traditional Rental Income: $748 Airbnb ROI: -1.62% Traditional ROI: 0.18%
35987 Birch Hollow Ln HILLSBORO, VA Welcome to Birch Hollow, a quiet culdesac community surrounded by open common areas, a sce...	5 beds \| 4 baths \| 6,155 sq.ft.	$1,099,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.77% Airbnb Rental Income: $3940 Traditional Rental Income: $4863 Airbnb ROI: 1.04% Traditional ROI: 2.77%
14963 Creek Point Ct HILLSBORO, VA Owners offering $10,000 closing cost credit with acceptable contract offer! Welcome home t...	4 beds \| 4 baths \| 5,356 sq.ft.	$1,299,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.55% Airbnb Rental Income: $2285 Traditional Rental Income: $2992 Airbnb ROI: -0.51% Traditional ROI: 0.55%
15375 Ashbury Overlook Ln HILLSBORO, VA 15375 Ashbury Overlook Ln, HILLSBORO, VA 20132 \| Other	N/A beds \| N/A baths \| N/A	$169,900	Airbnb cash on cash: -1.43% Traditional cash on cash: 1.78% Airbnb Rental Income: $413 Traditional Rental Income: $675 Airbnb ROI: -1.43% Traditional ROI: 1.78%
36660 Heskett HILLSBORO, VA Gorgeous homes in an idyllic setting - Welcome to The Ridges! 1-2 acre Home sites in the W...	4 beds \| 3 baths \| 4,100 sq.ft.	$1,405,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.03% Airbnb Rental Income: $2285 Traditional Rental Income: $2534 Airbnb ROI: -0.66% Traditional ROI: -0.03%
14550 Purcellville Rd HILLSBORO, VA NEW PRICE - Reduced $100K! Exceptional value for this one-of-a-kind 10.44-acre property in...	4 beds \| 2 baths \| 5,680 sq.ft.	$1,495,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.48% Airbnb Rental Income: $2285 Traditional Rental Income: $2856 Airbnb ROI: -0.34% Traditional ROI: 0.48%
37151 Branchriver HILLSBORO, VA Historic charm with modern updates! A century old and beautifully maintained, this Loudoun...	4 beds \| 3 baths \| 2,018 sq.ft.	$699,999	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.24% Airbnb Rental Income: $2285 Traditional Rental Income: $3410 Airbnb ROI: 0.71% Traditional ROI: 3.24%
37813 Baker Mill Rd HILLSBORO, VA A unique opportunity to own a beautiful move-in ready custom home on 10+ acres located les...	4 beds \| 4 baths \| 7,753 sq.ft.	$2,899,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.87% Airbnb Rental Income: $2285 Traditional Rental Income: $6272 Airbnb ROI: -0.83% Traditional ROI: 0.87%
38149 John Wolford Rd HILLSBORO, VA A Rare Estate Opportunity in the Heart of Western Loudoun's Wine Country Welcome to a one-...	5 beds \| 4 baths \| 6,537 sq.ft.	$2,100,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.95% Airbnb Rental Income: $3940 Traditional Rental Income: $5096 Airbnb ROI: -0.08% Traditional ROI: 0.95%
14127 Harpers Ferry Rd HILLSBORO, VA OPEN SUNDAY, 7/12 FROM 1-4PM - Set on 3+ acres just outside the historic village of Hillsb...	3 beds \| 2 baths \| 3,272 sq.ft.	$1,195,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.56% Airbnb Rental Income: $2507 Traditional Rental Income: $2388 Airbnb ROI: 0.12% Traditional ROI: 0.56%
16081 Purcellville Rd HILLSBORO, VA 16081 Purcellville Rd, HILLSBORO, VA 20132 \| Single Family Residential	4 beds \| 4 baths \| 4,081 sq.ft.	$1,799,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.14% Airbnb Rental Income: $2285 Traditional Rental Income: $2897 Airbnb ROI: -0.84% Traditional ROI: -0.14%
37860 Charles Town Pike HILLSBORO, VA 37860 Charles Town Pike, HILLSBORO, VA 20132 \| Single Family Residential	4 beds \| 2 baths \| 1,760 sq.ft.	$879,999	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.75% Airbnb Rental Income: $2285 Traditional Rental Income: $2193 Airbnb ROI: 0.17% Traditional ROI: 0.75%
13732 Harpers Ferry Rd HILLSBORO, VA 13732 Harpers Ferry Rd, HILLSBORO, VA 20132 \| Single Family Residential	5 beds \| 4 baths \| 4,417 sq.ft.	$1,250,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.67% Airbnb Rental Income: $3940 Traditional Rental Income: $2981 Airbnb ROI: 0.77% Traditional ROI: 0.67%
34971 Charles Town Pike HILLSBORO, VA 34971 Charles Town Pike, HILLSBORO, VA 20132 \| Single Family Residential	3 beds \| 3 baths \| 3,583 sq.ft.	$1,150,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0% Airbnb Rental Income: $2507 Traditional Rental Income: $2033 Airbnb ROI: -0.12% Traditional ROI: 0%

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

There are 22 investment properties available for sale in Hillsboro.

In 2026, the best neighborhood to buy investment property is HILLSBORO.

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

Your search for investment property begins and ends here

Investment Property for Sale in Hillsboro, VA

36944 Charles Town Pike

HILLSBORO, VA

3 beds | 2 baths | 1,824 sq.ft.

$674,900

Airbnb cash on cash: 1.32%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $2507

Traditional Rental Income: $2056

Airbnb ROI: 1.32%

Traditional ROI: 1.56%

13471 Sagle Rd

HILLSBORO, VA

4 beds | 4 baths | 3,590 sq.ft.

$1,320,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $2285

Traditional Rental Income: $3586

Airbnb ROI: -0.33%

Traditional ROI: 1.2%

13855 Paris Breeze Pl

HILLSBORO, VA

3 beds | 2 baths | 2,166 sq.ft.

$1,115,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $2507

Traditional Rental Income: $2172

Airbnb ROI: 0.1%

Traditional ROI: 0.37%

37275 Charles Town Pike

HILLSBORO, VA

3 beds | 2 baths | 2,058 sq.ft.

$999,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 0.65%

Airbnb Rental Income: $2507

Traditional Rental Income: $2115

Airbnb ROI: 0.42%

Traditional ROI: 0.65%

14001 Harpers Ferry Rd

HILLSBORO, VA

5 beds | 3 baths | 8,612 sq.ft.

$7,500,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: -1.02%

Airbnb Rental Income: $3940

Traditional Rental Income: $5627

Airbnb ROI: -1.38%

Traditional ROI: -1.02%

37517 Bernardini Ct #21

HILLSBORO, VA

5 beds | 5 baths | 6,000 sq.ft.

$1,799,900

Airbnb cash on cash: -0.08%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $3940

Traditional Rental Income: $4258

Airbnb ROI: -0.08%

Traditional ROI: 0.61%

11337 Russell Rd

HILLSBORO, VA

4 beds | 5 baths | 2,928 sq.ft.

$779,900

Airbnb cash on cash: 0.5%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $2285

Traditional Rental Income: $3780

Airbnb ROI: 0.5%

Traditional ROI: 3.34%

36660 HESKETT Lane

HILLSBORO, VA

4 beds | 5 baths | 5,200 sq.ft.

$1,595,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $2285

Traditional Rental Income: $2862

Airbnb ROI: -0.79%