Real Estate Investment Properties for Sale in Chester, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
96 Middlesex Avenue Chester, CT Steeped in history, awash in modern amenities and conveniences, this 4 bed (2 en suite), 3...	4 beds \| 4 baths \| 3,153 sq.ft.	$1,395,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.36% Airbnb Rental Income: $3924 Traditional Rental Income: $4622 Airbnb ROI: -0.83% Traditional ROI: 0.36%
5 Marina View Drive Chester, CT Rare opportunity - one owner home! Lovely contemporary Cape Cod with open floor plan, upda...	3 beds \| 4 baths \| 2,037 sq.ft.	$594,900	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.08% Airbnb Rental Income: $3922 Traditional Rental Income: $4095 Airbnb ROI: 2.25% Traditional ROI: 4.08%
39 Castle View Drive Chester, CT Nestled along the picturesque Connecticut River, minutes from the village of Chester, this...	3 beds \| 4 baths \| 2,208 sq.ft.	$419,900	Airbnb cash on cash: 4.47% Traditional cash on cash: 6.97% Airbnb Rental Income: $3922 Traditional Rental Income: $4064 Airbnb ROI: 4.47% Traditional ROI: 6.97%
Investment Properties for Sale in Other Cities of Connecticut
70 Old Town Road #315 Vernon , CT Newly Completed Foundation, Deck, and Sidewalk Replacement . Funky Townhouse quad level wi...	2 beds \| 2 baths \| 1,063 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2295 Airbnb ROI: N/A Traditional ROI: 8.1%
118 40 Acre Mountain Road Danbury , CT Stunning year-round views of Candlewood Lake set the stage for this contemporary Ranch sty...	3 beds \| 3 baths \| 2,755 sq.ft.	$685,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.46% Airbnb Rental Income: $6933 Traditional Rental Income: $4167 Airbnb ROI: 6.68% Traditional ROI: 4.46%
1 Broad Street #9G Stamford , CT Welcome to Park Tower, Stamford's premier luxury residence. This stunning corner unit prov...	2 beds \| 3 baths \| 1,677 sq.ft.	$699,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.39% Airbnb Rental Income: $3617 Traditional Rental Income: $3979 Airbnb ROI: -1.38% Traditional ROI: 0.39%
27 Waverly Road Darien , CT Welcome to 27 Waverly Road, a beautiful colonial-style home nestled in the Noroton Bay Ass...	5 beds \| 5 baths \| 4,257 sq.ft.	$3,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.53% Airbnb Rental Income: $null Traditional Rental Income: $6935 Airbnb ROI: N/A Traditional ROI: 0.53%
30 Coult Lane Old Lyme , CT Welcome to 30 Coult Lane, a spacious 4-bedroom, 2.5-bathroom split-level style home boasti...	4 beds \| 3 baths \| 3,076 sq.ft.	$599,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 4.21% Airbnb Rental Income: $3814 Traditional Rental Income: $4196 Airbnb ROI: 2.06% Traditional ROI: 4.21%
111 Plumtrees Road Bethel , CT Discover your dream home at this beautifully crafted Colonial, completed in 2018 that offe...	4 beds \| 4 baths \| 3,447 sq.ft.	$850,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 6.18% Airbnb Rental Income: $3635 Traditional Rental Income: $6119 Airbnb ROI: 2.04% Traditional ROI: 6.18%
613 Cherokee Lane #A Stratford , CT Introducing 613A Cherokee Lane! This completely renovated Oronoque Village condo sits righ...	2 beds \| 2 baths \| 1,804 sq.ft.	$439,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.91% Airbnb Rental Income: $2487 Traditional Rental Income: $2814 Airbnb ROI: 0.65% Traditional ROI: 2.91%
5 Woodhaven Drive Portland , CT Take a 3D Tour 24/7 or Enjoy a Video Walkthrough 24/7! Here's your opportunity to sweat so...	4 beds \| 2 baths \| 2,349 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.05% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 9.05%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.54% Airbnb Rental Income: $3436 Traditional Rental Income: $2560 Airbnb ROI: 3.81% Traditional ROI: 3.54%
66 Wilson Avenue Trumbull , CT Tiny House! The new trend in homes is right here and is a great alternative to condo livin...	2 beds \| 2 baths \| 648 sq.ft.	$339,900	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.15% Airbnb Rental Income: $1742 Traditional Rental Income: $2414 Airbnb ROI: 0.55% Traditional ROI: 4.15%
22 Boylston Street Milford , CT Welcome home to your quiet new home on Boylston Street! This charming three bedroom Cape p...	3 beds \| 2 baths \| 1,479 sq.ft.	$455,000	Airbnb cash on cash: 9.82% Traditional cash on cash: 5.42% Airbnb Rental Income: $6372 Traditional Rental Income: $3247 Airbnb ROI: 9.82% Traditional ROI: 5.42%
319 Thomaston Road #90 Watertown , CT Watertown Old Farms presents this meticulous 3 bedroom, 3 bath townhome that will WOW you ...	3 beds \| 3 baths \| 1,884 sq.ft.	$375,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 6.19% Airbnb Rental Income: $2788 Traditional Rental Income: $3517 Airbnb ROI: 2.26% Traditional ROI: 6.19%
215 Neds Mountain Road Ridgefield , CT Create, retreat and entertain in this boho chic mountain oasis with a bird's eye view of t...	2 beds \| 2 baths \| 2,795 sq.ft.	$819,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.38% Airbnb Rental Income: $null Traditional Rental Income: $2823 Airbnb ROI: N/A Traditional ROI: 1.38%
149 Ash Street BRIDGEPORT , CT Recently renovated, Colonial with open floor plan, Great for owner occupied, make an offer...	4 beds \| 2 baths \| 1,888 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.8% Airbnb Rental Income: $null Traditional Rental Income: $3418 Airbnb ROI: N/A Traditional ROI: 6.8%
4 Ledgebrook Drive #4 Norwalk , CT Discover a perfect blend of style and sophistication in this chic unit, offering the essen...	2 beds \| 2 baths \| 1,173 sq.ft.	$399,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 4.21% Airbnb Rental Income: $4409 Traditional Rental Income: $3059 Airbnb ROI: 5.35% Traditional ROI: 4.21%

Real Estate investment in Chester, CT

There are 3 properties for sale in the city of Chester . The median list price in Chester is $594,900 and the average price per square foot is $241. In December 2024, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $4,095.

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

There are 3 investment properties available for sale in Chester.

In 2024, the best neighborhood to buy investment property is Chester.

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $4,095.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, CT

96 Middlesex Avenue

Chester, CT

4 beds | 4 baths | 3,153 sq.ft.

$1,395,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $3924

Traditional Rental Income: $4622

Airbnb ROI: -0.83%

Traditional ROI: 0.36%

5 Marina View Drive

Chester, CT

3 beds | 4 baths | 2,037 sq.ft.

$594,900

Airbnb cash on cash: 2.25%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $3922

Traditional Rental Income: $4095

Airbnb ROI: 2.25%

Traditional ROI: 4.08%

39 Castle View Drive

Chester, CT

3 beds | 4 baths | 2,208 sq.ft.

$419,900

Airbnb cash on cash: 4.47%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $3922

Traditional Rental Income: $4064

Airbnb ROI: 4.47%

Traditional ROI: 6.97%

Investment Properties for Sale in Other Cities of Connecticut

Vernon , CT

2 beds | 2 baths | 1,063 sq.ft.

$169,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2295

Airbnb ROI: N/A

Traditional ROI: 8.1%

Danbury , CT

3 beds | 3 baths | 2,755 sq.ft.

$685,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $6933

Traditional Rental Income: $4167

Airbnb ROI: 6.68%

Traditional ROI: 4.46%

Stamford , CT

2 beds | 3 baths | 1,677 sq.ft.

$699,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $3617

Traditional Rental Income: $3979

Airbnb ROI: -1.38%

Traditional ROI: 0.39%

Darien , CT

5 beds | 5 baths | 4,257 sq.ft.

$3,495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.53%

Airbnb Rental Income: $null

Traditional Rental Income: $6935

Airbnb ROI: N/A

Traditional ROI: 0.53%

Old Lyme , CT

4 beds | 3 baths | 3,076 sq.ft.

$599,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3814

Traditional Rental Income: $4196

Airbnb ROI: 2.06%

Traditional ROI: 4.21%

Bethel , CT

4 beds | 4 baths | 3,447 sq.ft.

$850,000