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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
17040 Edgewood Way Middletown, CA 17040 Edgewood Way, Middletown, CA 95426 \| Single Family Residential	2 beds \| 1 baths \| 872 sq.ft.	$197,400	Airbnb cash on cash: -0.11% Traditional cash on cash: 8.18% Airbnb Rental Income: $708 Traditional Rental Income: $1955 Airbnb ROI: -0.11% Traditional ROI: 8.18%
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: 0.37% Traditional cash on cash: 2.72% Airbnb Rental Income: $1611 Traditional Rental Income: $2861 Airbnb ROI: 0.37% 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: -0.94% Traditional cash on cash: 3.29% Airbnb Rental Income: $467 Traditional Rental Income: $1349 Airbnb ROI: -0.94% Traditional ROI: 3.29%
21425 Valley Oak Drive Middletown, CA Custom-built 3 bed, 2.5 bath home in Middletownâs most desirable neighborhood. Owned sol...	3 beds \| 2 baths \| 2,050 sq.ft.	$529,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 5.68% Airbnb Rental Income: $4446 Traditional Rental Income: $3770 Airbnb ROI: 5.17% Traditional ROI: 5.68%
14986 Western Mine Road Middletown, CA Welcome to your peaceful escape just 1/2 mile from Hwy 29. This private 3bedroom 2 bath o...	3 beds \| 2 baths \| 1,404 sq.ft.	$629,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.13% Airbnb Rental Income: $4446 Traditional Rental Income: $2992 Airbnb ROI: 4.03% Traditional ROI: 3.13%
17205 Black Oak Hill Middletown, CA Modern single-level stucco home set on 23.57 acres with oak trees and meadow views. The op...	3 beds \| 2 baths \| 2,448 sq.ft.	$1,169,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 1.4% Airbnb Rental Income: $4446 Traditional Rental Income: $3763 Airbnb ROI: 1.18% Traditional ROI: 1.4%
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%
11081 Van Dorn Reservoir Road Middletown, CA Welcome to this unique creek-side home in Anderson Springs! Iconic architectural design m...	3 beds \| 2 baths \| 2,475 sq.ft.	$785,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.56% Airbnb Rental Income: $4446 Traditional Rental Income: $3996 Airbnb ROI: 2.9% Traditional ROI: 3.56%
21060 Santa Clara Middletown, CA PRIVATE OASIS IN MIDDLETOWN -The home features an open, sweeping floor plan with vaulted c...	3 beds \| 2 baths \| 1,760 sq.ft.	$575,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 3.78% Airbnb Rental Income: $4446 Traditional Rental Income: $3207 Airbnb ROI: 4.36% Traditional ROI: 3.78%
20102 Jaclyn Dr Middletown, CA	N/A beds \| N/A baths \| 0 sq.ft.	$499,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.6% Airbnb Rental Income: $761 Traditional Rental Income: $1193 Airbnb ROI: -1% Traditional ROI: 0.6%
17010 State Highway 175 Middletown, CA 17010 State Highway 175, Middletown, CA 95461 \| Single Family Residential	2 beds \| 2 baths \| 1,000 sq.ft.	$209,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 10.3% Airbnb Rental Income: $708 Traditional Rental Income: $2482 Airbnb ROI: -0.2% Traditional ROI: 10.3%
19760 Jaclyn Dr Middletown, CA 19760 Jaclyn Dr, Middletown, CA 95461 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 4.84% Airbnb Rental Income: $761 Traditional Rental Income: $1193 Airbnb ROI: 0.36% Traditional ROI: 4.84%

Real Estate investment in Middletown, CA

There are 14 properties for sale in the city of Middletown . The median list price in Middletown is $402,500 and the average price per square foot is $240. In February 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,603.

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

There are 14 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 $761.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, CA

17040 Edgewood Way

Middletown, CA

2 beds | 1 baths | 872 sq.ft.

$197,400

Airbnb cash on cash: -0.11%

Traditional cash on cash: 8.18%

Airbnb Rental Income: $708

Traditional Rental Income: $1955

Airbnb ROI: -0.11%

Traditional ROI: 8.18%

19665 Oat Hill Road

Middletown, CA

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

$779,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1611

Traditional Rental Income: $2861

Airbnb ROI: 0.37%

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: -0.94%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $467

Traditional Rental Income: $1349

Airbnb ROI: -0.94%

Traditional ROI: 3.29%

21425 Valley Oak Drive

Middletown, CA

3 beds | 2 baths | 2,050 sq.ft.

$529,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $4446

Traditional Rental Income: $3770

Airbnb ROI: 5.17%

Traditional ROI: 5.68%

14986 Western Mine Road

Middletown, CA

3 beds | 2 baths | 1,404 sq.ft.

$629,000

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $4446

Traditional Rental Income: $2992

Airbnb ROI: 4.03%

Traditional ROI: 3.13%

17205 Black Oak Hill

Middletown, CA

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

$1,169,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $4446

Traditional Rental Income: $3763

Airbnb ROI: 1.18%