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
Reliance Rd MIDDLETOWN, VA To Be Built by award winning builder Hepler Homes. The Lincoln Park model boasts over 22...	N/A beds \| N/A baths \| 2,211 sq.ft.	$645,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.67% Airbnb Rental Income: $537 Traditional Rental Income: $1738 Airbnb ROI: -0.79% Traditional ROI: 1.67%
3586 Reliance Rd MIDDLETOWN, VA Tucked away in a peaceful setting, this 3-bedroom, 2-bath home offers the perfect blend of...	3 beds \| 2 baths \| 2,240 sq.ft.	$549,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.62% Airbnb Rental Income: $1171 Traditional Rental Income: $2167 Airbnb ROI: -0.07% Traditional ROI: 2.62%
1115 Chapel Rd MIDDLETOWN, VA 1115 Chapel Rd, MIDDLETOWN, VA 22645 \| Single Family Residential	3 beds \| 2 baths \| 2,969 sq.ft.	$3,100,000	Airbnb cash on cash: -1.57% Traditional cash on cash: -1.13% Airbnb Rental Income: $1171 Traditional Rental Income: $2076 Airbnb ROI: -1.57% Traditional ROI: -1.13%
LOT 31 Comforter Ln MIDDLETOWN, VA LOT 31 Comforter Ln, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.86% Airbnb Rental Income: $537 Traditional Rental Income: $590 Airbnb ROI: -0.26% Traditional ROI: 2.86%
0 Reliance MIDDLETOWN, VA 0 Reliance, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$725,000	Airbnb cash on cash: -1.57% Traditional cash on cash: -1.08% Airbnb Rental Income: $537 Traditional Rental Income: $590 Airbnb ROI: -1.57% Traditional ROI: -1.08%
Veterans - Lot 12 Rd MIDDLETOWN, VA Veterans - Lot 12 Rd, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$549,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -0.85% Airbnb Rental Income: $537 Traditional Rental Income: $590 Airbnb ROI: -1.49% Traditional ROI: -0.85%
145 Dursley Cir MIDDLETOWN, VA ""Ã¢â¬Â¹Welcome to this move-in ready Cedar model in the Villages at Middletown-where mod...	4 beds \| 2 baths \| 1,900 sq.ft.	$465,999	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.38% Airbnb Rental Income: $2074 Traditional Rental Income: $2625 Airbnb ROI: 1.89% Traditional ROI: 4.38%
Tbd Veterans Rd MIDDLETOWN, VA Tbd Veterans Rd, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$1,900,000	Airbnb cash on cash: -1.72% Traditional cash on cash: -1.53% Airbnb Rental Income: $537 Traditional Rental Income: $590 Airbnb ROI: -1.72% Traditional ROI: -1.53%
4 Jackson Pl MIDDLETOWN, VA 4 Jackson Pl, MIDDLETOWN, VA 22645 \| Single Family Residential	6 beds \| 5 baths \| 5,785 sq.ft.	$874,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.07% Airbnb Rental Income: $2503 Traditional Rental Income: $4073 Airbnb ROI: 0.4% Traditional ROI: 3.07%
298 Mcdaniel Ln MIDDLETOWN, VA Privacy, space, and convenience come together in this all-brick ranch on just over 7 acres...	3 beds \| 2 baths \| 2,730 sq.ft.	$639,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.71% Airbnb Rental Income: $1171 Traditional Rental Income: $3212 Airbnb ROI: -0.35% Traditional ROI: 3.71%
154 Dursley Cir MIDDLETOWN, VA Better than new and meticulously maintained, this beautiful 4-bedroom, 2.5-bath home offer...	4 beds \| 2 baths \| 1,680 sq.ft.	$449,900	Airbnb cash on cash: 1.81% Traditional cash on cash: 2.92% Airbnb Rental Income: $2074 Traditional Rental Income: $2008 Airbnb ROI: 1.81% Traditional ROI: 2.92%
0 River Ridge Dr MIDDLETOWN, VA 0 River Ridge Dr, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$385,000	Airbnb cash on cash: -1.36% Traditional cash on cash: -0.43% Airbnb Rental Income: $537 Traditional Rental Income: $593 Airbnb ROI: -1.36% Traditional ROI: -0.43%
7756 CAROLYN Avenue MIDDLETOWN, VA "Come On Over To Carolyn" This 3-bedroom, 2-full bathroom ranch style home is ready for yo...	3 beds \| 2 baths \| 1,139 sq.ft.	$319,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 4.95% Airbnb Rental Income: $1171 Traditional Rental Income: $1998 Airbnb ROI: 0.92% Traditional ROI: 4.95%
461 Veterans Rd MIDDLETOWN, VA Coming Soon! Interior Photos will be uploaded July 9th. First time offered on the market, ...	3 beds \| 3 baths \| 2,784 sq.ft.	$729,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 3.37% Airbnb Rental Income: $1171 Traditional Rental Income: $3258 Airbnb ROI: -0.26% Traditional ROI: 3.37%
171 BIRMINGHAM Drive MIDDLETOWN, VA This home was built in 2023 and well cared for from day one. Several upgrades were made fo...	3 beds \| 2 baths \| 1,332 sq.ft.	$399,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 4.15% Airbnb Rental Income: $1171 Traditional Rental Income: $2211 Airbnb ROI: 0.35% Traditional ROI: 4.15%
228 Mercys Dr MIDDLETOWN, VA PRICED BELOW APPRAISED VALUE!! Nestled on an expansive 6.84-acre lot just minutes from sho...	5 beds \| 5 baths \| 5,672 sq.ft.	$949,999	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.37% Airbnb Rental Income: $2503 Traditional Rental Income: $6105 Airbnb ROI: 0.61% Traditional ROI: 5.37%
7927 Main St MIDDLETOWN, VA An exceptional opportunity to restore and reimagine a historic Main Street property in the...	4 beds \| 2 baths \| 2,512 sq.ft.	$379,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 5.79% Airbnb Rental Income: $2074 Traditional Rental Income: $2622 Airbnb ROI: 2.74% Traditional ROI: 5.79%
209 Mineral St MIDDLETOWN, VA 209 Mineral St, MIDDLETOWN, VA 22645 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.8% Airbnb Rental Income: $537 Traditional Rental Income: $584 Airbnb ROI: -0.26% Traditional ROI: 2.8%
0 Gruver Grade Dr MIDDLETOWN, VA 0 Gruver Grade Dr, MIDDLETOWN, VA 22645 \| Single Family Residential	4 beds \| 3 baths \| 3,086 sq.ft.	$1,350,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.11% Airbnb Rental Income: $2074 Traditional Rental Income: $2510 Airbnb ROI: -0.66% Traditional ROI: 0.11%
2105 Shawn Dr MIDDLETOWN, VA 2105 Shawn Dr, MIDDLETOWN, VA 22645 \| Single Family Residential	3 beds \| 2 baths \| 1,674 sq.ft.	$420,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.65% Airbnb Rental Income: $1171 Traditional Rental Income: $1850 Airbnb ROI: -0.05% Traditional ROI: 2.65%
80 Little Sorrel Dr MIDDLETOWN, VA 80 Little Sorrel Dr, MIDDLETOWN, VA 22645 \| Single Family Residential	6 beds \| 5 baths \| 3,908 sq.ft.	$774,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.73% Airbnb Rental Income: $2503 Traditional Rental Income: $4094 Airbnb ROI: 0.68% Traditional ROI: 3.73%
354 Guard Hill Rd MIDDLETOWN, VA 354 Guard Hill Rd, MIDDLETOWN, VA 22645 \| Single Family Residential	4 beds \| 3 baths \| 2,840 sq.ft.	$825,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.41% Airbnb Rental Income: $2074 Traditional Rental Income: $2571 Airbnb ROI: 0.07% Traditional ROI: 1.41%

Real Estate investment in Middletown, VA

There are 29 properties for sale in the city of Middletown . The median list price in Middletown is $438,737 and the average price per square foot is $242. In July 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,210.

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

There are 29 investment properties available for sale in Middletown.

In 2026, 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 $1,171.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, VA

Reliance Rd

MIDDLETOWN, VA

N/A beds | N/A baths | 2,211 sq.ft.

$645,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $537

Traditional Rental Income: $1738

Airbnb ROI: -0.79%

Traditional ROI: 1.67%

3586 Reliance Rd

MIDDLETOWN, VA

3 beds | 2 baths | 2,240 sq.ft.

$549,900

Airbnb cash on cash: -0.07%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $1171

Traditional Rental Income: $2167

Airbnb ROI: -0.07%

Traditional ROI: 2.62%

1115 Chapel Rd

MIDDLETOWN, VA

3 beds | 2 baths | 2,969 sq.ft.

$3,100,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: -1.13%

Airbnb Rental Income: $1171

Traditional Rental Income: $2076

Airbnb ROI: -1.57%

Traditional ROI: -1.13%

LOT 31 Comforter Ln

MIDDLETOWN, VA

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

$110,000

Airbnb cash on cash: -0.26%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $537

Traditional Rental Income: $590

Airbnb ROI: -0.26%

Traditional ROI: 2.86%

0 Reliance

MIDDLETOWN, VA

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

$725,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: -1.08%

Airbnb Rental Income: $537

Traditional Rental Income: $590

Airbnb ROI: -1.57%

Traditional ROI: -1.08%

Veterans - Lot 12 Rd

MIDDLETOWN, VA

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

$549,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $537

Traditional Rental Income: $590

Airbnb ROI: -1.49%

Traditional ROI: -0.85%

145 Dursley Cir

MIDDLETOWN, VA

4 beds | 2 baths | 1,900 sq.ft.

$465,999

Airbnb cash on cash: 1.89%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $2074

Traditional Rental Income: $2625

Airbnb ROI: 1.89%

Traditional ROI: 4.38%

Tbd Veterans Rd

MIDDLETOWN, VA

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

$1,900,000

Airbnb cash on cash: -1.72%

Traditional cash on cash: -1.53%

Airbnb Rental Income: $537

Traditional Rental Income: $590

Airbnb ROI: -1.72%