Real Estate Investment Properties for Sale in Middletown, VA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
215 THOMAS DRIVE MIDDLETOWN, VA Now is your chance to call this all-brick custom-built cape cod home sitting on 2 partiall...	3 beds \| 3 baths \| 2,410 sq.ft.	$525,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 3.83% Airbnb Rental Income: $3347 Traditional Rental Income: $2658 Airbnb ROI: 3.71% Traditional ROI: 3.83%
2239 SIXTH STREET MIDDLETOWN, VA Have you been looking for the perfect sophisticated and elegant historic home? Do you want...	4 beds \| 3 baths \| 3,255 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $2573 Airbnb ROI: N/A Traditional ROI: 2.44%
627 CHIMNEY CIRCLE MIDDLETOWN, VA This home is the perfect combination of Subdivision and privacy close to downtown Middleto...	4 beds \| 3 baths \| 4,115 sq.ft.	$699,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 3.35%
180 NEWELL DRIVE MIDDLETOWN, VA Stunning Executive Home Perfect for Entertaining!! Welcome to this luxurious 5-bedroom, 5...	5 beds \| 6 baths \| 6,239 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $5616 Airbnb ROI: N/A Traditional ROI: 3.41%
374 BOYERS MILL LANE MIDDLETOWN, VA Nestled on a sprawling 5-acre lot, this exquisite log home embodies the perfect blend of r...	3 beds \| 2 baths \| 2,338 sq.ft.	$650,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.17% Airbnb Rental Income: $3347 Traditional Rental Income: $2798 Airbnb ROI: 2.84% Traditional ROI: 3.17%
115 RELIANCE WOODS DRIVE MIDDLETOWN, VA This exceptional home offers the perfect blend of privacy and convenience, nestled on a be...	4 beds \| 3 baths \| 3,120 sq.ft.	$774,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 2.61%
1449 RELIANCE ROAD MIDDLETOWN, VA Circa 1885 home from yesteryear needs some TLC to shine again. This property will likely b...	3 beds \| 2 baths \| 2,704 sq.ft.	$399,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 4.71% Airbnb Rental Income: $3347 Traditional Rental Income: $2374 Airbnb ROI: 5.32% Traditional ROI: 4.71%
131 BIRMINGHAM DR MIDDLETOWN, VA It's Time to Rediscover the Shenandoah Valley again, here between the Blue Ridge Mountains...	4 beds \| 3 baths \| N/A	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 4.12%

Real Estate investment in Middletown, VA

There are 8 properties for sale in the city of Middletown . The median list price in Middletown is $674,950 and the average price per square foot is $195. In September 2025, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,728.

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

There are 8 investment properties available for sale in Middletown.

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

The ROI for Short-Term is higher than the Long-Term in Middletown with average rental income of $3,347.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, VA

215 THOMAS DRIVE

MIDDLETOWN, VA

3 beds | 3 baths | 2,410 sq.ft.

$525,000

Airbnb cash on cash: 3.71%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $3347

Traditional Rental Income: $2658

Airbnb ROI: 3.71%

Traditional ROI: 3.83%

2239 SIXTH STREET

MIDDLETOWN, VA

4 beds | 3 baths | 3,255 sq.ft.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2573

Airbnb ROI: N/A

Traditional ROI: 2.44%

627 CHIMNEY CIRCLE

MIDDLETOWN, VA

4 beds | 3 baths | 4,115 sq.ft.

$699,990

Airbnb cash on cash: N/A

Traditional cash on cash: 3.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2975

Airbnb ROI: N/A

Traditional ROI: 3.35%

180 NEWELL DRIVE

MIDDLETOWN, VA

5 beds | 6 baths | 6,239 sq.ft.

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.41%

Airbnb Rental Income: $null

Traditional Rental Income: $5616

Airbnb ROI: N/A

Traditional ROI: 3.41%

374 BOYERS MILL LANE

MIDDLETOWN, VA

3 beds | 2 baths | 2,338 sq.ft.

$650,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $3347

Traditional Rental Income: $2798

Airbnb ROI: 2.84%

Traditional ROI: 3.17%

115 RELIANCE WOODS DRIVE

MIDDLETOWN, VA

4 beds | 3 baths | 3,120 sq.ft.

$774,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3036

Airbnb ROI: N/A

Traditional ROI: 2.61%

1449 RELIANCE ROAD

MIDDLETOWN, VA

3 beds | 2 baths | 2,704 sq.ft.

$399,000

Airbnb cash on cash: 5.32%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $3347

Traditional Rental Income: $2374

Airbnb ROI: 5.32%

Traditional ROI: 4.71%

131 BIRMINGHAM DR

MIDDLETOWN, VA

4 beds | 3 baths | N/A

$440,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2337

Airbnb ROI: N/A