Real Estate Investment Properties for Sale in Essex, CT

Looking for investment property in Essex, CT with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
11 N Main Street Essex, CT Welcome to the reimagined John Miner House on North Main Street in the charming Connecticu...	4 beds \| 4 baths \| 3,036 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.78% Airbnb Rental Income: $null Traditional Rental Income: $7050 Airbnb ROI: N/A Traditional ROI: 3.78%
9 Essex Hills Drive Essex, CT Exquisitely updated & remodeled Essex home on the cusp of South Cove with easterly views. ...	4 beds \| 3 baths \| 2,676 sq.ft.	$1,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $3874 Airbnb ROI: N/A Traditional ROI: 0.73%
33 Deep River Road Essex, CT Incredible investment opportunity. Mixed use/flex space including two existing apartments....	4 beds \| 6 baths \| 7,309 sq.ft.	$829,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.59% Airbnb Rental Income: $null Traditional Rental Income: $7525 Airbnb ROI: N/A Traditional ROI: 7.59%
22 Ebony Lane Essex, CT Welcome to this beautifully maintained Colonial at 22 Ebony Lane in Ivoryton, offering a t...	4 beds \| 3 baths \| 2,550 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.83% Airbnb Rental Income: $null Traditional Rental Income: $4199 Airbnb ROI: N/A Traditional ROI: 4.83%
134 River Road Essex, CT Commanding one of the highest and most breathtaking viewpoints in Essex, Eagles Peak offer...	5 beds \| 8 baths \| 7,405 sq.ft.	$2,495,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 2.05% Airbnb Rental Income: $2910 Traditional Rental Income: $9907 Airbnb ROI: -1.26% Traditional ROI: 2.05%
56 S Main Street Essex, CT Essex Village antique gem. A lovely and updated antique with overflowing charm and full of...	2 beds \| 3 baths \| 2,106 sq.ft.	$874,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.3% Airbnb Rental Income: $1944 Traditional Rental Income: $3551 Airbnb ROI: -0.3% Traditional ROI: 2.3%
45 Main Street Essex, CT The Parker Bull House, circa 1754 located in Ivoryton overlooking the Falls River, this st...	3 beds \| 3 baths \| 2,456 sq.ft.	$799,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.4% Airbnb Rental Income: $1435 Traditional Rental Income: $2612 Airbnb ROI: -0.75% Traditional ROI: 1.4%
108 Westbrook Road Essex, CT Amazing custom built Nantucket style Cape situated on sprawling grounds, terraced high abo...	4 beds \| 5 baths \| 5,610 sq.ft.	$1,895,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $7770 Airbnb ROI: N/A Traditional ROI: 2.47%
101 N Main Street Essex, CT Nestled in the heart of Essex Village along one of its most picturesque streets, this icon...	4 beds \| 4 baths \| 3,724 sq.ft.	$1,849,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.52% Airbnb Rental Income: $null Traditional Rental Income: $5776 Airbnb ROI: N/A Traditional ROI: 1.52%

Real Estate investment in Essex, CT

There are 12 properties for sale in the city of Essex . The median list price in Essex is $385,750 and the average price per square foot is $176. In March 2026, the average monthly cash on cash return in Essex is 2.00%. The average monthly rental income in Essex is $4,988.

Essex, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 12 investment properties available for sale in Essex.

In 2026, the best neighborhood to buy investment property is Essex.

The ROI for Long-Term is higher than the Short-Term in Essex with average rental income of $4,988.

Your search for investment property begins and ends here

Investment Property for Sale in Essex, CT

11 N Main Street

Essex, CT

4 beds | 4 baths | 3,036 sq.ft.

$1,350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.78%

Airbnb Rental Income: $null

Traditional Rental Income: $7050

Airbnb ROI: N/A

Traditional ROI: 3.78%

9 Essex Hills Drive

Essex, CT

4 beds | 3 baths | 2,676 sq.ft.

$1,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3874

Airbnb ROI: N/A

Traditional ROI: 0.73%

33 Deep River Road

Essex, CT

4 beds | 6 baths | 7,309 sq.ft.

$829,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.59%

Airbnb Rental Income: $null

Traditional Rental Income: $7525

Airbnb ROI: N/A

Traditional ROI: 7.59%

22 Ebony Lane

Essex, CT

4 beds | 3 baths | 2,550 sq.ft.

$649,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.83%

Airbnb Rental Income: $null

Traditional Rental Income: $4199

Airbnb ROI: N/A

Traditional ROI: 4.83%

134 River Road

Essex, CT

5 beds | 8 baths | 7,405 sq.ft.

$2,495,000

Airbnb cash on cash: -1.26%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $2910

Traditional Rental Income: $9907

Airbnb ROI: -1.26%

Traditional ROI: 2.05%

56 S Main Street

Essex, CT

2 beds | 3 baths | 2,106 sq.ft.

$874,900

Airbnb cash on cash: -0.3%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $1944

Traditional Rental Income: $3551

Airbnb ROI: -0.3%

Traditional ROI: 2.3%

45 Main Street

Essex, CT

3 beds | 3 baths | 2,456 sq.ft.

$799,900

Airbnb cash on cash: -0.75%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $1435

Traditional Rental Income: $2612

Airbnb ROI: -0.75%

Traditional ROI: 1.4%

108 Westbrook Road

Essex, CT

4 beds | 5 baths | 5,610 sq.ft.

$1,895,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.47%

Airbnb Rental Income: $null

Traditional Rental Income: $7770

Airbnb ROI: N/A