Real Estate Investment Properties for Sale in Upperville, VA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9124 JOHN S MOSBY HIGHWAY UPPERVILLE, VA Charming historic gem in Upperville a rare find! This stunning home sits on a peaceful .63...	4 beds \| 4 baths \| 5,048 sq.ft.	$1,120,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 1.97% Airbnb Rental Income: $4827 Traditional Rental Income: $3792 Airbnb ROI: 2.01% Traditional ROI: 1.97%
Investment Properties for Sale in Other Cities of Virginia
5621 Rolling Hills Drive Dublin , VA Charming Brick Ranch on Spacious Level Lot - Ideal Location Near Radford University & Virg...	3 beds \| 1 baths \| 1,000 sq.ft.	$199,900	Airbnb cash on cash: 8.75% Traditional cash on cash: 5.46% Airbnb Rental Income: $2663 Traditional Rental Income: $1407 Airbnb ROI: 8.75% Traditional ROI: 5.46%
1101 Knights Bridge Lane Virginia Beach , VA Welcome to this charming Traditional Home nestled in an established Virginia Beach neighbo...	4 beds \| 3 baths \| 3,200 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $4057 Airbnb ROI: N/A Traditional ROI: 2.72%
22565 WINDSOR LOCKS SQUARE Ashburn , VA Welcome to this stunning East-facing, brick-front corner 28 foot wide townhouse offering a...	4 beds \| 5 baths \| 3,688 sq.ft.	$895,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.38% Airbnb Rental Income: $4673 Traditional Rental Income: $4612 Airbnb ROI: 2.29% Traditional ROI: 3.38%
22472 CAMBRIDGEPORT SQUARE Ashburn , VA Great location,End unit townhome at Moorefield Station. Fresh Paint, entry-level bedroom w...	4 beds \| 4 baths \| 2,164 sq.ft.	$745,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.3% Airbnb Rental Income: $4673 Traditional Rental Income: $3113 Airbnb ROI: 3.15% Traditional ROI: 2.3%
12000 MARKET STREET #352 Reston , VA A spacious 2-bedroom, 2-bath condominium set within the established Savoy at Reston Town C...	2 beds \| 2 baths \| 1,150 sq.ft.	$499,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.3% Airbnb Rental Income: $3625 Traditional Rental Income: $2602 Airbnb ROI: 3.79% Traditional ROI: 3.3%
420 Faire Chase Chesapeake , VA MOVE IN READY! Lovely two bedroom, 2.5 bath townhome located in the desirable Great Bridge...	2 beds \| 3 baths \| 1,208 sq.ft.	$290,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.5% Airbnb Rental Income: $1757 Traditional Rental Income: $1833 Airbnb ROI: 2.46% Traditional ROI: 4.5%
117 Bute Street Suffolk , VA THIS IS A SHORT SALE, SUBJECT TO THIRD PARTY APPROVAL. PRICE NOT BANK APPROVED. Welcome to...	3 beds \| 1 baths \| 1,000 sq.ft.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.97% Airbnb Rental Income: $null Traditional Rental Income: $1637 Airbnb ROI: N/A Traditional ROI: 6.97%
3433 Willow Breeze Drive Portsmouth , VA Gorgeous three bedroom ranch located in the desirable Churchland area of Portsmouth. This ...	3 beds \| 2 baths \| 1,142 sq.ft.	$334,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.24% Airbnb Rental Income: $1771 Traditional Rental Income: $1723 Airbnb ROI: 1.86% Traditional ROI: 3.24%
124 S Fir Avenue Virginia Beach , VA Welcome to your Virginia Beach gem! This 1,940 sqft beauty has room for it all! With 3 bed...	3 beds \| 3 baths \| 1,940 sq.ft.	$442,500	Airbnb cash on cash: 1.21% Traditional cash on cash: 6% Airbnb Rental Income: $1865 Traditional Rental Income: $3350 Airbnb ROI: 1.21% Traditional ROI: 6%
612 RIVERCREST DR McLean , VA Worldbid auction - October 22nd noon. Qualifying round sealed bids due no later than Octob...	5 beds \| 12 baths \| N/A	$21,950,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -1.55% Airbnb Rental Income: $5533 Traditional Rental Income: $5458 Airbnb ROI: -1.6% Traditional ROI: -1.55%
2109 North Avenue Richmond , VA Fantastic investment opportunity in the exploding Northside section of Richmond! Located m...	6 beds \| 6 baths \| 3,356 sq.ft.	$599,950	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $1762 Airbnb ROI: N/A Traditional ROI: 0.97%
7024 STATENDAM COURT McLean , VA Open SUNDAY afternoon from 1 to 3:15 pm. Owners are willing to work with offers. This bea...	4 beds \| 3 baths \| 2,312 sq.ft.	$1,199,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.3% Airbnb Rental Income: $5759 Traditional Rental Income: $3932 Airbnb ROI: 1.91% Traditional ROI: 1.3%
611 Dunkerry Lane Sandston , VA Welcome home to this stunning brick Colonial, perfectly situated on over an acre in the se...	4 beds \| 3 baths \| 2,184 sq.ft.	$449,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 4.56% Airbnb Rental Income: $4221 Traditional Rental Income: $2788 Airbnb ROI: 5.85% Traditional ROI: 4.56%
4801 Annlyn Drive Sandston , VA Welcome to 4801 Annlyn Drive - a delightful 3-bedroom, 1-bath ranch-style retreat tucked a...	3 beds \| 1 baths \| 1,014 sq.ft.	$240,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 5.71% Airbnb Rental Income: $2833 Traditional Rental Income: $1790 Airbnb ROI: 7.39% Traditional ROI: 5.71%
44004 FLORENCE TERRACE Ashburn , VA Introducing 44004 Florence Terrace, a beautifully maintained 4bed, 3bath townhome nestled ...	4 beds \| 4 baths \| 2,137 sq.ft.	$645,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 3.14% Airbnb Rental Income: $4673 Traditional Rental Income: $3201 Airbnb ROI: 3.98% Traditional ROI: 3.14%

Real Estate investment in Upperville, VA

There are 1 properties for sale in the city of Upperville . The median list price in Upperville is $1,120,000 and the average price per square foot is $222. In September 2025, the average monthly cash on cash return in Upperville is 2.00%. The average monthly rental income in Upperville is $3,792.

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

There are 1 investment properties available for sale in Upperville.

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

The ROI for Short-Term is higher than the Long-Term in Upperville with average rental income of $4,827.

Your search for investment property begins and ends here

Investment Property for Sale in Upperville, VA

9124 JOHN S MOSBY HIGHWAY

UPPERVILLE, VA

4 beds | 4 baths | 5,048 sq.ft.

$1,120,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $4827

Traditional Rental Income: $3792

Airbnb ROI: 2.01%

Traditional ROI: 1.97%

Investment Properties for Sale in Other Cities of Virginia

Dublin , VA

3 beds | 1 baths | 1,000 sq.ft.

$199,900

Airbnb cash on cash: 8.75%

Traditional cash on cash: 5.46%

Airbnb Rental Income: $2663

Traditional Rental Income: $1407

Airbnb ROI: 8.75%

Traditional ROI: 5.46%

Virginia Beach , VA

4 beds | 3 baths | 3,200 sq.ft.

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 2.72%

Airbnb Rental Income: $null

Traditional Rental Income: $4057

Airbnb ROI: N/A

Traditional ROI: 2.72%

Ashburn , VA

4 beds | 5 baths | 3,688 sq.ft.

$895,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $4673

Traditional Rental Income: $4612

Airbnb ROI: 2.29%

Traditional ROI: 3.38%

Ashburn , VA

4 beds | 4 baths | 2,164 sq.ft.

$745,000

Airbnb cash on cash: 3.15%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $4673

Traditional Rental Income: $3113

Airbnb ROI: 3.15%

Traditional ROI: 2.3%

Reston , VA

2 beds | 2 baths | 1,150 sq.ft.

$499,900

Airbnb cash on cash: 3.79%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $3625

Traditional Rental Income: $2602

Airbnb ROI: 3.79%

Traditional ROI: 3.3%

Chesapeake , VA

2 beds | 3 baths | 1,208 sq.ft.

$290,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1757

Traditional Rental Income: $1833

Airbnb ROI: 2.46%

Traditional ROI: 4.5%

Suffolk , VA

3 beds | 1 baths | 1,000 sq.ft.

$180,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.97%

Airbnb Rental Income: $null

Traditional Rental Income: $1637

Airbnb ROI: N/A

Traditional ROI: 6.97%

Portsmouth , VA

3 beds | 2 baths | 1,142 sq.ft.

$334,900

Airbnb cash on cash: 1.86%

Traditional cash on cash: 3.24%