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
28 River Road Essex, CT The Benjamin F. Post House, c. 1801, has been thoroughly and thoughtfully updated to provi...	3 beds \| 3 baths \| 2,359 sq.ft.	$1,595,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.11% Airbnb Rental Income: $2287 Traditional Rental Income: $2612 Airbnb ROI: -0.5% Traditional ROI: 0.11%
15 Novelty Lane Essex, CT Essex Village waterfront enjoys one-level living and truly incredible sunrise colors and d...	3 beds \| 3 baths \| 2,384 sq.ft.	$2,499,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.1% Airbnb Rental Income: $2287 Traditional Rental Income: $4527 Airbnb ROI: -1.11% Traditional ROI: 0.1%
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: -0.32% Traditional cash on cash: 7.56% Airbnb Rental Income: $1962 Traditional Rental Income: $7525 Airbnb ROI: -0.32% Traditional ROI: 7.56%
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.	$449,999	Airbnb cash on cash: 1.8% Traditional cash on cash: 3.84% Airbnb Rental Income: $2250 Traditional Rental Income: $2546 Airbnb ROI: 1.8% Traditional ROI: 3.84%
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.	$2,200,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.06% Airbnb Rental Income: $3228 Traditional Rental Income: $9782 Airbnb ROI: -0.5% Traditional ROI: 3.06%
175 River Road Essex, CT A rare opportunity to own a meticulously designed enclave set on nearly three private acre...	3 beds \| 5 baths \| 4,664 sq.ft.	$6,595,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.27% Airbnb Rental Income: $2287 Traditional Rental Income: $7508 Airbnb ROI: -1.22% Traditional ROI: -0.27%
5 Hemlock Drive Essex, CT Every home tells a story, and 5 Hemlock Drive's is one of transformation. Perched high abo...	4 beds \| 3 baths \| 3,023 sq.ft.	$1,895,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.18% Airbnb Rental Income: $1962 Traditional Rental Income: $4450 Airbnb ROI: -0.53% Traditional ROI: 1.18%
45 Main Street Essex, CT Set on 1.6 acres overlooking the Falls River in Ivoryton, the historic Parker Bull House, ...	3 beds \| 3 baths \| 2,456 sq.ft.	$699,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.89% Airbnb Rental Income: $2287 Traditional Rental Income: $4038 Airbnb ROI: 0.34% Traditional ROI: 3.89%
10 Scholes Lane Essex, CT Steeped in history and prominently positioned in the heart of Essex Village, the distingui...	5 beds \| 4 baths \| 3,769 sq.ft.	$3,595,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.29% Airbnb Rental Income: $3228 Traditional Rental Income: $6397 Airbnb ROI: -0.88% Traditional ROI: 0.29%
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.	$899,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 1.88% Airbnb Rental Income: $1962 Traditional Rental Income: $4289 Airbnb ROI: -1.51% Traditional ROI: 1.88%
50 Pond Meadow Road Essex, CT PRICE ADJUSTMENT Welcome home to 50 Pond Meadow. Move right in and enjoy the comfort of re...	2 beds \| 1 baths \| 944 sq.ft.	$421,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.7% Airbnb Rental Income: $2250 Traditional Rental Income: $1838 Airbnb ROI: 2.31% Traditional ROI: 2.7%
25 River Road Essex, CT Hidden in plain sight! An extraordinary pocket estate within walking distance via sidewalk...	4 beds \| 3 baths \| 3,232 sq.ft.	$2,250,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.73% Airbnb Rental Income: $1962 Traditional Rental Income: $4740 Airbnb ROI: -0.85% Traditional ROI: 0.73%
21 River Road Essex, CT Historic Waterfront Sanctuary on Falls River Cove Set on a private 2.57-acre peninsula sur...	5 beds \| 5 baths \| 3,502 sq.ft.	$2,850,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 1.28% Airbnb Rental Income: $3228 Traditional Rental Income: $8577 Airbnb ROI: -1.02% Traditional ROI: 1.28%
9 Ingham Hill Road Essex, CT This charming and updated historic colonial is tucked away on a quiet road on 1.4 acres. T...	3 beds \| 5 baths \| 3,308 sq.ft.	$1,150,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.64% Airbnb Rental Income: $2287 Traditional Rental Income: $6975 Airbnb ROI: -0.27% Traditional ROI: 4.64%
15 Nutmeg Lane Essex, CT This well maintained 4 bedroom Colonial is located not far from Essex Village at the end o...	4 beds \| 3 baths \| 2,160 sq.ft.	$495,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 6.24% Airbnb Rental Income: $1962 Traditional Rental Income: $3922 Airbnb ROI: 0.89% Traditional ROI: 6.24%
10 Main Street Essex, CT 3 Bedroom, 2 Bathroom home tucked away privately off a shared driveway. Generous + flexibl...	3 beds \| 2 baths \| 1,456 sq.ft.	$379,900	Airbnb cash on cash: 2.5% Traditional cash on cash: 5.77% Airbnb Rental Income: $2287 Traditional Rental Income: $2884 Airbnb ROI: 2.5% Traditional ROI: 5.77%

Real Estate investment in Essex, CT

There are 22 properties for sale in the city of Essex . The median list price in Essex is $415,950 and the average price per square foot is $188. In November 2026, the average monthly cash on cash return in Essex is 3.00%. The average monthly rental income in Essex is $4,370.

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

There are 22 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 $2,287.

Your search for investment property begins and ends here

Investment Property for Sale in Essex, CT

28 River Road

Essex, CT

3 beds | 3 baths | 2,359 sq.ft.

$1,595,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $2287

Traditional Rental Income: $2612

Airbnb ROI: -0.5%

Traditional ROI: 0.11%

15 Novelty Lane

Essex, CT

3 beds | 3 baths | 2,384 sq.ft.

$2,499,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2287

Traditional Rental Income: $4527

Airbnb ROI: -1.11%

Traditional ROI: 0.1%

33 Deep River Road

Essex, CT

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

$829,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 7.56%

Airbnb Rental Income: $1962

Traditional Rental Income: $7525

Airbnb ROI: -0.32%

Traditional ROI: 7.56%

46 Main Street

Essex, CT

2 beds | 2 baths | 1,252 sq.ft.

$449,999

Airbnb cash on cash: 1.8%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $2250

Traditional Rental Income: $2546

Airbnb ROI: 1.8%

Traditional ROI: 3.84%

88 Main Street

Essex, CT

5 beds | 6 baths | 5,234 sq.ft.

$2,200,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3228

Traditional Rental Income: $9782

Airbnb ROI: -0.5%

Traditional ROI: 3.06%

175 River Road

Essex, CT

3 beds | 5 baths | 4,664 sq.ft.

$6,595,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $2287

Traditional Rental Income: $7508

Airbnb ROI: -1.22%

Traditional ROI: -0.27%

5 Hemlock Drive

Essex, CT

4 beds | 3 baths | 3,023 sq.ft.

$1,895,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $1962

Traditional Rental Income: $4450

Airbnb ROI: -0.53%

Traditional ROI: 1.18%

45 Main Street

Essex, CT

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

$699,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $2287

Traditional Rental Income: $4038

Airbnb ROI: 0.34%