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: -1.25% Traditional cash on cash: 0% Airbnb Rental Income: $1967 Traditional Rental Income: $6465 Airbnb ROI: -1.25% Traditional ROI: 0%
25 Pratt Street Essex, CT HIGHEST AND BEST DUE BY MONDAY, JUNE 1ST, 12:00 NOON. Nestled in the heart of the historic...	3 beds \| 4 baths \| 2,950 sq.ft.	$1,650,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.26% Airbnb Rental Income: $1967 Traditional Rental Income: $5018 Airbnb ROI: -1.06% Traditional ROI: 1.26%
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: -1.16% Traditional cash on cash: -0.44% Airbnb Rental Income: $1967 Traditional Rental Income: $3771 Airbnb ROI: -1.16% 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 \| 5 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%
8 Squire Lane Essex, CT Nestled on a cul-de-sac just a short stroll from the Village of Essex, this exceptional Co...	5 beds \| 4 baths \| 3,902 sq.ft.	$1,195,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.19% Airbnb Rental Income: $1859 Traditional Rental Income: $5907 Airbnb ROI: -0.9% Traditional ROI: 3.19%
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 Wonderful waterfront antique home on 1.6 acres. The Parker Bull House, circa 1754 located ...	3 beds \| 3 baths \| 2,456 sq.ft.	$759,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.58% Airbnb Rental Income: $1967 Traditional Rental Income: $4068 Airbnb ROI: -0.11% Traditional ROI: 3.58%
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.	$1,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $7770 Airbnb ROI: N/A Traditional ROI: 2.67%
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.	$1,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.59% Airbnb Rental Income: $null Traditional Rental Income: $5776 Airbnb ROI: N/A Traditional ROI: 1.59%
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: 0.78% Traditional cash on cash: 3.67% Airbnb Rental Income: $1760 Traditional Rental Income: $2546 Airbnb ROI: 0.78% Traditional ROI: 3.67%
88 Main Street Essex, CT Two hours from New York City. Two hours from Boston. A world away from both. Privacy is th...	5 beds \| 6 baths \| 5,234 sq.ft.	$2,600,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 2.47% Airbnb Rental Income: $1859 Traditional Rental Income: $9782 Airbnb ROI: -1.02% Traditional ROI: 2.47%
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: -0.12% Traditional cash on cash: 3.1% Airbnb Rental Income: $1760 Traditional Rental Income: $3456 Airbnb ROI: -0.12% 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: -1.21% Traditional cash on cash: -0.38% Airbnb Rental Income: $1967 Traditional Rental Income: $7508 Airbnb ROI: -1.21% Traditional ROI: -0.38%
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.	$445,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.31% Airbnb Rental Income: $1760 Traditional Rental Income: $2131 Airbnb ROI: 1.27% Traditional ROI: 3.31%
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: -0.15% Traditional cash on cash: 6.28% Airbnb Rental Income: $1967 Traditional Rental Income: $6096 Airbnb ROI: -0.15% Traditional ROI: 6.28%
5 Hemlock Drive Essex, CT 5 Hemlock Drive is a 1972 Acorn Deck House - one of the most admired prefab designs in Ame...	4 beds \| 3 baths \| 3,023 sq.ft.	$1,975,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.1% Airbnb Rental Income: $null Traditional Rental Income: $4450 Airbnb ROI: N/A Traditional ROI: 1.1%
27 Birch Mill Trail Essex, CT Welcome to 27 Birch Mill Trail, an absolute gem nestled in one of Essex's most desirable a...	3 beds \| 3 baths \| 2,216 sq.ft.	$695,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.44% Airbnb Rental Income: $1967 Traditional Rental Income: $3627 Airbnb ROI: 0.08% Traditional ROI: 3.44%
26 Grandview Terrace Essex, CT Welcome to 26 Grandview Terrace, Essex! Situated right in the heart of ESSEX VILLAGE, this...	3 beds \| 3 baths \| 1,216 sq.ft.	$750,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.47% Airbnb Rental Income: $1967 Traditional Rental Income: $3057 Airbnb ROI: 0.17% Traditional ROI: 2.47%
16 Main Street Essex, CT Nestled in the heart of the quaint village of Ivoryton, this circa 1920 home offers timele...	4 beds \| 3 baths \| 1,884 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $4024 Airbnb ROI: N/A Traditional ROI: 7.43%
10 Scholes Lane Essex, CT Steeped in history and prominently positioned in the heart of Essex Village, the distingui...	4 beds \| 4 baths \| 3,769 sq.ft.	$4,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.12% Airbnb Rental Income: $null Traditional Rental Income: $6397 Airbnb ROI: N/A Traditional ROI: 0.12%
38 N Main Street #5 Essex, CT Rarely available Luxury first-floor Condominium in the Heart of Historic Essex Village. On...	2 beds \| 2 baths \| 1,400 sq.ft.	$825,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.44% Airbnb Rental Income: $1760 Traditional Rental Income: $2715 Airbnb ROI: -0.43% Traditional ROI: 1.44%
6 Beechwood Drive Essex, CT Nestled on a private 1.82-acre homesite in picturesque Ivoryton, this stunning new constru...	4 beds \| 3 baths \| 2,552 sq.ft.	$959,750	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $4289 Airbnb ROI: N/A Traditional ROI: 1.57%

Real Estate investment in Essex, CT

There are 29 properties for sale in the city of Essex . The median list price in Essex is $527,000 and the average price per square foot is $243. In June 2026, the average monthly cash on cash return in Essex is 2.00%. The average monthly rental income in Essex is $4,068.

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

There are 29 investment properties available for sale in Essex.

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

The ROI for Short-Term is higher than the Long-Term in Essex with average rental income of $1,913.

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: -1.25%

Traditional cash on cash: 0%

Airbnb Rental Income: $1967

Traditional Rental Income: $6465

Airbnb ROI: -1.25%

Traditional ROI: 0%

25 Pratt Street

Essex, CT

3 beds | 4 baths | 2,950 sq.ft.

$1,650,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $1967

Traditional Rental Income: $5018

Airbnb ROI: -1.06%

Traditional ROI: 1.26%

17 Scholes Lane

Essex, CT

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

$3,495,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $1967

Traditional Rental Income: $3771

Airbnb ROI: -1.16%

Traditional ROI: -0.44%

11 N Main Street

Essex, CT

4 beds | 5 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%

8 Squire Lane

Essex, CT

5 beds | 4 baths | 3,902 sq.ft.

$1,195,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1859

Traditional Rental Income: $5907

Airbnb ROI: -0.9%

Traditional ROI: 3.19%

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.

$759,900

Airbnb cash on cash: -0.11%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $1967

Traditional Rental Income: $4068

Airbnb ROI: -0.11%

Traditional ROI: 3.58%

108 Westbrook Road

Essex, CT

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

$1,795,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.67%

Airbnb Rental Income: $null

Traditional Rental Income: $7770

Airbnb ROI: N/A