Real Estate Investment Properties for Sale in Bolton, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
56 West Street Bolton, CT Set on a scenic two-acre lot in desirable Bolton, this beautifully renovated Colonial offe...	4 beds \| 2 baths \| 2,372 sq.ft.	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $3600 Airbnb ROI: N/A Traditional ROI: 5.49%
42 Castlerock Lane Bolton, CT Meticulously maintained Colonial located on a cul-de-sac in Bolton, built in 2007, offerin...	4 beds \| 4 baths \| 3,664 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $5743 Airbnb ROI: N/A Traditional ROI: 3.83%
14 Dean Drive Bolton, CT Move in ready and energy efficient! New central heating and cooling system, oil tank, well...	3 beds \| 2 baths \| 1,860 sq.ft.	$450,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 4.53% Airbnb Rental Income: $2152 Traditional Rental Income: $3090 Airbnb ROI: 1.01% Traditional ROI: 4.53%
55 Stone Hedge Lane Bolton, CT .	3 beds \| 3 baths \| 2,516 sq.ft.	$497,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.04% Airbnb Rental Income: $2152 Traditional Rental Income: $3835 Airbnb ROI: 0.25% Traditional ROI: 5.04%
52 Country Club Road Bolton, CT Prepare to be captivated by this stunning, stately brick Colonial, perfectly situated on a...	5 beds \| 5 baths \| 5,102 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $8382 Airbnb ROI: N/A Traditional ROI: 6.46%
166 Boston Turnpike #A Bolton, CT Brand New Seven unit one of a kind 55+ active adult community in BOLTON! Four homes ready ...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
166 Boston Turnpike #B Bolton, CT Brand New Seven unit one of a kind 55+ active adult community in BOLTON! Four homes ready ...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
166 Boston Turnpike #C Bolton, CT Brand New Seven unit one of a kind 55+ active adult community in BOLTON! Four homes ready ...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
166 Boston Turnpike #D Bolton, CT Unit D available soon. Brand New Seven unit one of a kind 55+ active adult community in BO...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
166 Boston Turnpike #F Bolton, CT Unit F available soon. Brand New Seven unit one of a kind 55+ active adult community in BO...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
166 Boston Turnpike #G Bolton, CT Unit G available soon! Brand New Seven unit one of a kind 55+ active adult community in BO...	2 beds \| 2 baths \| 938 sq.ft.	$229,900	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.66% Airbnb Rental Income: $1869 Traditional Rental Income: $2627 Airbnb ROI: -0.13% Traditional ROI: 5.66%
5 Llynwood Drive Bolton, CT Colonial on private level lot across the street from Bolton Lake, and steps from the walki...	2 beds \| 2 baths \| 2,694 sq.ft.	$389,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.51% Airbnb Rental Income: $1869 Traditional Rental Income: $2826 Airbnb ROI: 0.53% Traditional ROI: 4.51%

Real Estate investment in Bolton, CT

There are 13 properties for sale in the city of Bolton . The median list price in Bolton is $548,500 and the average price per square foot is $224. In November 2026, the average monthly cash on cash return in Bolton is 6.00%. The average monthly rental income in Bolton is $2,826.

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

There are 13 investment properties available for sale in Bolton.

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

The ROI for Short-Term is higher than the Long-Term in Bolton with average rental income of $1,869.

Your search for investment property begins and ends here

Investment Property for Sale in Bolton, CT

56 West Street

Bolton, CT

4 beds | 2 baths | 2,372 sq.ft.

$444,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3600

Airbnb ROI: N/A

Traditional ROI: 5.49%

42 Castlerock Lane

Bolton, CT

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

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $5743

Airbnb ROI: N/A

Traditional ROI: 3.83%

14 Dean Drive

Bolton, CT

3 beds | 2 baths | 1,860 sq.ft.

$450,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $2152

Traditional Rental Income: $3090

Airbnb ROI: 1.01%

Traditional ROI: 4.53%

55 Stone Hedge Lane

Bolton, CT

3 beds | 3 baths | 2,516 sq.ft.

$497,900

Airbnb cash on cash: 0.25%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $2152

Traditional Rental Income: $3835

Airbnb ROI: 0.25%

Traditional ROI: 5.04%

52 Country Club Road

Bolton, CT

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

$899,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.46%

Airbnb Rental Income: $null

Traditional Rental Income: $8382

Airbnb ROI: N/A

Traditional ROI: 6.46%

166 Boston Turnpike #A

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: -0.13%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $1869

Traditional Rental Income: $2627

Airbnb ROI: -0.13%

Traditional ROI: 5.66%

166 Boston Turnpike #B

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: -0.13%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $1869

Traditional Rental Income: $2627

Airbnb ROI: -0.13%

Traditional ROI: 5.66%

166 Boston Turnpike #C

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: -0.13%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $1869

Traditional Rental Income: $2627

Airbnb ROI: -0.13%