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

separator

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.	$4,495,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.15% Airbnb Rental Income: $2484 Traditional Rental Income: $6465 Airbnb ROI: -0.95% Traditional ROI: 0.15%
1 Foxboro Road Essex, CT Essex Waterfront Signature Property: A Victorian Gem on the Connecticut River ~ Experience...	4 beds \| 5 baths \| 4,131 sq.ft.	$3,995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.47% Airbnb Rental Income: $null Traditional Rental Income: $8513 Airbnb ROI: N/A Traditional ROI: 0.47%
5 Parker Terrace Essex, CT "The Barn", named for the reclaimed beams and flooring sourced from the barn that once sto...	4 beds \| 4 baths \| 2,156 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $4727 Airbnb ROI: N/A Traditional ROI: 2.94%
7 Dickinson Lane Essex, CT Rare opportunity to own an extraordinary, in-town, estate on 1.2 professionally landscaped...	4 beds \| 6 baths \| 6,824 sq.ft.	$4,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.7% Airbnb Rental Income: $null Traditional Rental Income: $9820 Airbnb ROI: N/A Traditional ROI: 0.7%
11 North 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.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $7050 Airbnb ROI: N/A Traditional ROI: 3.58%
91 Book Hill Road Essex, CT Exceptional living in sought-after Essex location. This stately gambrel- colonial has been...	4 beds \| 5 baths \| 4,102 sq.ft.	$1,055,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $5726 Airbnb ROI: N/A Traditional ROI: 2.61%
17 Lookout Hill Essex, CT An impressive and enchanting private retreat set on 1.51 acres atop a quiet cul-de-sac min...	5 beds \| 6 baths \| 5,364 sq.ft.	$1,349,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 2.61% Airbnb Rental Income: $2272 Traditional Rental Income: $7292 Airbnb ROI: -1.84% Traditional ROI: 2.61%
45 Main Street Essex, CT The Parker Bull House, circa 1754, is one of the oldest historic homes in Essex. Located i...	3 beds \| 3 baths \| 2,456 sq.ft.	$824,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.05% Airbnb Rental Income: $2484 Traditional Rental Income: $4068 Airbnb ROI: -0.8% Traditional ROI: 2.05%
18 Benson Lane Essex, CT Perhaps once in a generation might an Essex village property with so much to offer and suc...	4 beds \| 3 baths \| 2,634 sq.ft.	$1,675,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.52% Airbnb Rental Income: $null Traditional Rental Income: $4148 Airbnb ROI: N/A Traditional ROI: -0.52%
13 Maple Avenue Essex, CT Available for the first time in over 30 years! Perfectly situated in the heart of Essex Vi...	3 beds \| 4 baths \| 2,359 sq.ft.	$875,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 3.17% Airbnb Rental Income: $2484 Traditional Rental Income: $5225 Airbnb ROI: -0.93% Traditional ROI: 3.17%
60 North Main Street Essex, CT Sweet reproduction Saltbox Colonial in Essex Village. Home has been in the same family for...	3 beds \| 3 baths \| 1,344 sq.ft.	$769,900	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.79% Airbnb Rental Income: $2484 Traditional Rental Income: $2903 Airbnb ROI: -0.63% Traditional ROI: 0.79%
14 Blake Street Essex, CT Historic charm meets modern comfort in this 1900 Pratt Reed farmhouse. Featuring 3 bedroom...	3 beds \| 2 baths \| 1,129 sq.ft.	$399,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.66% Airbnb Rental Income: $2484 Traditional Rental Income: $2634 Airbnb ROI: 1.65% Traditional ROI: 3.66%
15 Cedar Street Essex, CT Nestled in the picturesque village of Centerbrook and just down the road from scenic Mill ...	3 beds \| 2 baths \| 1,934 sq.ft.	$499,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.31% Airbnb Rental Income: $2484 Traditional Rental Income: $3097 Airbnb ROI: 0.7% Traditional ROI: 3.31%
91 Main Street Essex, CT Nestled within the five-home enclave of Queen's Gate, this beautifully maintained Colonial...	3 beds \| 3 baths \| 3,354 sq.ft.	$649,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 2.99% Airbnb Rental Income: $2484 Traditional Rental Income: $3906 Airbnb ROI: -0.35% Traditional ROI: 2.99%
95 Main Street Essex, CT One of five custom homes set in the enclave of Queen's Gate. Enjoy the best of both worlds...	3 beds \| 4 baths \| 2,394 sq.ft.	$589,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.16% Airbnb Rental Income: $2484 Traditional Rental Income: $4761 Airbnb ROI: -0.07% Traditional ROI: 5.16%
67 Melody Lane Essex, CT Located on a quiet, tree-lined street in Ivoryton, this 1950s gem is a true testament to o...	3 beds \| 2 baths \| 1,732 sq.ft.	$525,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.02% Airbnb Rental Income: $2484 Traditional Rental Income: $3107 Airbnb ROI: 0.52% Traditional ROI: 3.02%

Real Estate investment in Essex, CT

There are 17 properties for sale in the city of Essex . The median list price in Essex is $1,055,000 and the average price per square foot is $351. In October 2025, the average monthly cash on cash return in Essex is 3.00%. The average monthly rental income in Essex is $4,727.

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

There are 17 investment properties available for sale in Essex.

In 2025, 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 $2,484.

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.

$4,495,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $2484

Traditional Rental Income: $6465

Airbnb ROI: -0.95%

Traditional ROI: 0.15%

1 Foxboro Road

Essex, CT

4 beds | 5 baths | 4,131 sq.ft.

$3,995,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.47%

Airbnb Rental Income: $null

Traditional Rental Income: $8513

Airbnb ROI: N/A

Traditional ROI: 0.47%

5 Parker Terrace

Essex, CT

4 beds | 4 baths | 2,156 sq.ft.

$1,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.94%

Airbnb Rental Income: $null

Traditional Rental Income: $4727

Airbnb ROI: N/A

Traditional ROI: 2.94%

7 Dickinson Lane

Essex, CT

4 beds | 6 baths | 6,824 sq.ft.

$4,795,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.7%

Airbnb Rental Income: $null

Traditional Rental Income: $9820

Airbnb ROI: N/A

Traditional ROI: 0.7%

11 North Main Street

Essex, CT

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

$1,400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.58%

Airbnb Rental Income: $null

Traditional Rental Income: $7050

Airbnb ROI: N/A

Traditional ROI: 3.58%

91 Book Hill Road

Essex, CT

4 beds | 5 baths | 4,102 sq.ft.

$1,055,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $5726

Airbnb ROI: N/A

Traditional ROI: 2.61%

17 Lookout Hill

Essex, CT

5 beds | 6 baths | 5,364 sq.ft.

$1,349,000

Airbnb cash on cash: -1.84%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $2272

Traditional Rental Income: $7292

Airbnb ROI: -1.84%

Traditional ROI: 2.61%

45 Main Street

Essex, CT

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

$824,900

Airbnb cash on cash: -0.8%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $2484

Traditional Rental Income: $4068

Airbnb ROI: -0.8%