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
7 Hanna Lane Essex, CT Fresh Update for a Classic Connecticut Home - Discover a beautifully restored 1955 waterfr...	3 beds \| 4 baths \| 4,383 sq.ft.	$4,300,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 0% Airbnb Rental Income: $993 Traditional Rental Income: $6465 Airbnb ROI: -1.46% Traditional ROI: 0%
17 Scholes Lane Essex, CT Experience the essence of Essex village living in this distinguished historic home. Perfec...	3 beds \| 3 baths \| 2,092 sq.ft.	$3,495,000	Airbnb cash on cash: -1.41% Traditional cash on cash: -0.44% Airbnb Rental Income: $993 Traditional Rental Income: $3771 Airbnb ROI: -1.41% Traditional ROI: -0.44%
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.	$1,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $7050 Airbnb ROI: N/A Traditional ROI: 3.96%
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%
39 Prospect Street Essex, CT Hilltop Cottage c.1900 The Perfect pied a terre in the heart of the historic Essex CT yach...	2 beds \| 2 baths \| 961 sq.ft.	$815,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.41% Airbnb Rental Income: $1299 Traditional Rental Income: $2474 Airbnb ROI: -0.67% Traditional ROI: 1.41%
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%
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: -1.24% Traditional cash on cash: 3.36% Airbnb Rental Income: $993 Traditional Rental Income: $4068 Airbnb ROI: -1.24% Traditional ROI: 3.36%
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.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $4199 Airbnb ROI: N/A Traditional ROI: 5.05%
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%
1 Verona Street Essex, CT A Picture-Perfect Custom Cape in Ivoryton. Welcome to this beautifully maintained and thou...	3 beds \| 3 baths \| 2,218 sq.ft.	$695,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 3.61% Airbnb Rental Income: $993 Traditional Rental Income: $3689 Airbnb ROI: -1.09% Traditional ROI: 3.61%
46 Main Street Essex, CT Discover the perfect blend of income potential and small-town charm with this centrally lo...	2 beds \| 2 baths \| 1,252 sq.ft.	$469,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.67% Airbnb Rental Income: $1299 Traditional Rental Income: $2546 Airbnb ROI: -0.09% Traditional ROI: 3.67%
88 Main Street Essex, CT Move into this elegantly designed, meticulously restored estate in the nationally register...	5 beds \| 6 baths \| 5,234 sq.ft.	$2,800,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.22% Airbnb Rental Income: $2122 Traditional Rental Income: $9782 Airbnb ROI: -0.94% Traditional ROI: 2.22%
65 Main Street #24 Essex, CT Enjoy easy living just steps from the charm of Ivoryton Village in this beautifully mainta...	2 beds \| 3 baths \| 1,384 sq.ft.	$399,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.63% Airbnb Rental Income: $1299 Traditional Rental Income: $2616 Airbnb ROI: 0.03% Traditional ROI: 4.63%
112 Main Street Essex, CT Nestled on a prime 0.5-acre corner lot in the heart of Centerbrook, 112 Main Street is a m...	3 beds \| 3 baths \| 2,407 sq.ft.	$799,900	Airbnb cash on cash: -1.05% Traditional cash on cash: 3.03% Airbnb Rental Income: $993 Traditional Rental Income: $3680 Airbnb ROI: -1.05% Traditional ROI: 3.03%
1 Benson Lane Essex, CT Located in the Essex Village district on a corner lot at Saybrook Road and Benson Lane, th...	2 beds \| 2 baths \| 1,179 sq.ft.	$750,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.8% Airbnb Rental Income: $1299 Traditional Rental Income: $2468 Airbnb ROI: -0.46% Traditional ROI: 1.8%
14 Essex Glen Drive #4 Essex, CT Tucked within an intimate enclave of just 26 thoughtfully designed homes in Essex -- often...	2 beds \| 2 baths \| 1,589 sq.ft.	$724,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.1% Airbnb Rental Income: $1299 Traditional Rental Income: $3456 Airbnb ROI: -0.69% Traditional ROI: 3.1%
175 River Road Essex, CT Set along one of Essex's most coveted stretches of River Road, this exceptional waterfront...	3 beds \| 5 baths \| 4,664 sq.ft.	$7,889,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.38% Airbnb Rental Income: $993 Traditional Rental Income: $7508 Airbnb ROI: -1.32% Traditional ROI: -0.38%
7 Mitchel Terrace Essex, CT Tucked into a peaceful woodland setting near the scenic Falls River Preserve, this strikin...	3 beds \| 2 baths \| 1,880 sq.ft.	$597,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.54% Airbnb Rental Income: $993 Traditional Rental Income: $3068 Airbnb ROI: -0.81% Traditional ROI: 3.54%
52 Pond Meadow Road Essex, CT Welcome home to this charming and beautifully maintained cottage-style farmhouse offering ...	2 beds \| 2 baths \| 810 sq.ft.	$450,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.27% Airbnb Rental Income: $1299 Traditional Rental Income: $2131 Airbnb ROI: 0.33% Traditional ROI: 3.27%
74 Bushy Hill Road Essex, CT Tucked away on 2.53 picturesque acres in Ivoryton, this inviting Cape Cod offers the perfe...	3 beds \| 4 baths \| 3,476 sq.ft.	$775,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 6.28% Airbnb Rental Income: $993 Traditional Rental Income: $6096 Airbnb ROI: -1.27% Traditional ROI: 6.28%

Real Estate investment in Essex, CT

There are 23 properties for sale in the city of Essex . The median list price in Essex is $419,900 and the average price per square foot is $197. In May 2026, the average monthly cash on cash return in Essex is 3.00%. The average monthly rental income in Essex is $3,847.

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

There are 23 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 $3,847.

Your search for investment property begins and ends here

Investment Property for Sale in Essex, CT

7 Hanna Lane

Essex, CT

3 beds | 4 baths | 4,383 sq.ft.

$4,300,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 0%

Airbnb Rental Income: $993

Traditional Rental Income: $6465

Airbnb ROI: -1.46%

Traditional ROI: 0%

17 Scholes Lane

Essex, CT

3 beds | 3 baths | 2,092 sq.ft.

$3,495,000

Airbnb cash on cash: -1.41%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $993

Traditional Rental Income: $3771

Airbnb ROI: -1.41%

Traditional ROI: -0.44%

11 N Main Street

Essex, CT

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

$1,300,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.96%

Airbnb Rental Income: $null

Traditional Rental Income: $7050

Airbnb ROI: N/A

Traditional ROI: 3.96%

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%

39 Prospect Street

Essex, CT

2 beds | 2 baths | 961 sq.ft.

$815,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $1299

Traditional Rental Income: $2474

Airbnb ROI: -0.67%

Traditional ROI: 1.41%

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%

45 Main Street

Essex, CT

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

$799,900

Airbnb cash on cash: -1.24%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $993

Traditional Rental Income: $4068

Airbnb ROI: -1.24%

Traditional ROI: 3.36%

22 Ebony Lane

Essex, CT

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

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.05%

Airbnb Rental Income: $null

Traditional Rental Income: $4199

Airbnb ROI: N/A