Real Estate Investment Properties for Sale in Middletown, CA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
19665 Oat Hill Road Middletown, CA Charming Ranch Home with Expansive Land and Scenic Views! Discover the potential of this 1...	4 beds \| 1 baths \| 1,574 sq.ft.	$779,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.72% Airbnb Rental Income: $1826 Traditional Rental Income: $2861 Airbnb ROI: 0.62% Traditional ROI: 2.72%
21264 Santa Clara Road Middletown, CA MIDDLETOWN CUSTOM HOME - Sophisticated home on private .34 acre lot in prime Middletown lo...	3 beds \| 2 baths \| 2,264 sq.ft.	$575,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 5.34% Airbnb Rental Income: $4446 Traditional Rental Income: $3933 Airbnb ROI: 4.56% Traditional ROI: 5.34%
20511 Santa Barbara Avenue Middletown, CA Charming Country Ranchette Awaits! Welcome to your country retreat, where peaceful...	3 beds \| 2 baths \| 1,890 sq.ft.	$669,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.03% Airbnb Rental Income: $4446 Traditional Rental Income: $3701 Airbnb ROI: 3.73% Traditional ROI: 4.03%
15868 Main Street Middletown, CA This adorable cabin is located right in the heart of Middletown. Close to dining, shopping...	1 beds \| 1 baths \| 576 sq.ft.	$288,888	Airbnb cash on cash: -0.88% Traditional cash on cash: 3.29% Airbnb Rental Income: $485 Traditional Rental Income: $1349 Airbnb ROI: -0.88% Traditional ROI: 3.29%
15625 June Bug Middletown, CA Sprawling across 6.9 beautiful acres in the heart of Lake County, this stunning 4-bedroom,...	4 beds \| 3 baths \| 3,114 sq.ft.	$789,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.53% Airbnb Rental Income: $1826 Traditional Rental Income: $4734 Airbnb ROI: -0.09% Traditional ROI: 4.53%
22550 Shady Grove Road Middletown, CA Looking for acreage? Creek? and lots of privacy ? Here you go . This property is as you...	3 beds \| 1 baths \| 1,734 sq.ft.	$1,340,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 0.75% Airbnb Rental Income: $4446 Traditional Rental Income: $2992 Airbnb ROI: 1.18% Traditional ROI: 0.75%
17205 Black Oak Hill Middletown, CA Welcome to this stunning single-level modern stucco home, perfectly situated on 23.57 acre...	3 beds \| 2 baths \| 2,448 sq.ft.	$1,200,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.34% Airbnb Rental Income: $4446 Traditional Rental Income: $3763 Airbnb ROI: 1.12% Traditional ROI: 1.34%
24019 Hilderbrand Drive Middletown, CA Country Home with additional Thriving Bed & Breakfast Income or Idyllic Family Retreat â...	3 beds \| 2 baths \| 2,490 sq.ft.	$675,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1% Airbnb Rental Income: $4446 Traditional Rental Income: $1985 Airbnb ROI: 3.43% Traditional ROI: 1%

Real Estate investment in Middletown, CA

There are 9 properties for sale in the city of Middletown . The median list price in Middletown is $675,000 and the average price per square foot is $350. In December 2025, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,992.

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

There are 9 investment properties available for sale in Middletown.

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

The ROI for Long-Term is higher than the Short-Term in Middletown with average rental income of $2,992.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CA

19665 Oat Hill Road

Middletown, CA

4 beds | 1 baths | 1,574 sq.ft.

$779,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1826

Traditional Rental Income: $2861

Airbnb ROI: 0.62%

Traditional ROI: 2.72%

21264 Santa Clara Road

Middletown, CA

3 beds | 2 baths | 2,264 sq.ft.

$575,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $4446

Traditional Rental Income: $3933

Airbnb ROI: 4.56%

Traditional ROI: 5.34%

20511 Santa Barbara Avenue

Middletown, CA

3 beds | 2 baths | 1,890 sq.ft.

$669,000

Airbnb cash on cash: 3.73%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $4446

Traditional Rental Income: $3701

Airbnb ROI: 3.73%

Traditional ROI: 4.03%

15868 Main Street

Middletown, CA

1 beds | 1 baths | 576 sq.ft.

$288,888

Airbnb cash on cash: -0.88%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $485

Traditional Rental Income: $1349

Airbnb ROI: -0.88%

Traditional ROI: 3.29%

15625 June Bug

Middletown, CA

4 beds | 3 baths | 3,114 sq.ft.

$789,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1826

Traditional Rental Income: $4734

Airbnb ROI: -0.09%

Traditional ROI: 4.53%

22550 Shady Grove Road

Middletown, CA

3 beds | 1 baths | 1,734 sq.ft.

$1,340,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $4446

Traditional Rental Income: $2992

Airbnb ROI: 1.18%

Traditional ROI: 0.75%

17205 Black Oak Hill

Middletown, CA

3 beds | 2 baths | 2,448 sq.ft.

$1,200,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $4446

Traditional Rental Income: $3763

Airbnb ROI: 1.12%

Traditional ROI: 1.34%

24019 Hilderbrand Drive

Middletown, CA

3 beds | 2 baths | 2,490 sq.ft.

$675,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 1%

Airbnb Rental Income: $4446

Traditional Rental Income: $1985

Airbnb ROI: 3.43%