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 St Bolton, CT Beautifully renovated and move-in ready, 56 West Street offers the space, setting, and upd...	4 beds \| 2 baths \| 2,372 sq.ft.	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $3600 Airbnb ROI: N/A Traditional ROI: 4.87%
9 Tumblebrook Rd Bolton, CT Raised ranch with new kitchen, new Anderson windows, newer roof, tile and hardwood floors ...	3 beds \| 2 baths \| 1,434 sq.ft.	$449,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.56% Airbnb Rental Income: $2158 Traditional Rental Income: $2755 Airbnb ROI: 0.84% Traditional ROI: 3.56%
85 School Rd Bolton, CT Impeccable Fiano custom built 4 bedrooms, 3 bath Colonial with 9' ceilings, crown molding,...	4 beds \| 3 baths \| 2,906 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $4184 Airbnb ROI: N/A Traditional ROI: 3.57%
55 Stone Hedge Ln Bolton, CT Beautifully maintained 3 bedroom, 2.5 bath Colonial set on 1.42 private acres in a desirab...	3 beds \| 2 baths \| 2,516 sq.ft.	$529,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.77% Airbnb Rental Income: $2158 Traditional Rental Income: $3835 Airbnb ROI: 0.27% Traditional ROI: 4.77%
52 Country Club Rd Bolton, CT Prepare to be captivated by this stunning, stately brick Colonial, perfectly situated on a...	4 beds \| 4 baths \| 5,400 sq.ft.	$949,800	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $8382 Airbnb ROI: N/A Traditional ROI: 6.18%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
166 Boston Tpke #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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%
7 Tinker Pond Road Bolton, CT Own your own mini estate! The 3900 sq ft custom design Contemporary/Colonial is set on a p...	4 beds \| 3 baths \| 3,911 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $4366 Airbnb ROI: N/A Traditional ROI: 3.59%
166 Boston Tpke #E 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: 1.28% Traditional cash on cash: 8.55% Airbnb Rental Income: $1482 Traditional Rental Income: $2627 Airbnb ROI: 1.28% Traditional ROI: 8.55%

Real Estate investment in Bolton, CT

There are 15 properties for sale in the city of Bolton . The median list price in Bolton is $599,000 and the average price per square foot is $247. In September 2026, the average monthly cash on cash return in Bolton is 7.00%. The average monthly rental income in Bolton is $2,691.

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

There are 15 investment properties available for sale in Bolton.

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

The ROI for Long-Term is higher than the Short-Term in Bolton with average rental income of $2,691.

Your search for investment property begins and ends here

Investment Property for Sale in Bolton, CT

56 West St

Bolton, CT

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

$489,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $3600

Airbnb ROI: N/A

Traditional ROI: 4.87%

9 Tumblebrook Rd

Bolton, CT

3 beds | 2 baths | 1,434 sq.ft.

$449,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $2158

Traditional Rental Income: $2755

Airbnb ROI: 0.84%

Traditional ROI: 3.56%

85 School Rd

Bolton, CT

4 beds | 3 baths | 2,906 sq.ft.

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.57%

Airbnb Rental Income: $null

Traditional Rental Income: $4184

Airbnb ROI: N/A

Traditional ROI: 3.57%

55 Stone Hedge Ln

Bolton, CT

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

$529,900

Airbnb cash on cash: 0.27%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $2158

Traditional Rental Income: $3835

Airbnb ROI: 0.27%

Traditional ROI: 4.77%

52 Country Club Rd

Bolton, CT

4 beds | 4 baths | 5,400 sq.ft.

$949,800

Airbnb cash on cash: N/A

Traditional cash on cash: 6.18%

Airbnb Rental Income: $null

Traditional Rental Income: $8382

Airbnb ROI: N/A

Traditional ROI: 6.18%

166 Boston Tpke #A

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: 1.28%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $1482

Traditional Rental Income: $2627

Airbnb ROI: 1.28%

Traditional ROI: 8.55%

166 Boston Tpke #B

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: 1.28%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $1482

Traditional Rental Income: $2627

Airbnb ROI: 1.28%

Traditional ROI: 8.55%

166 Boston Tpke #c

Bolton, CT

2 beds | 2 baths | 938 sq.ft.

$229,900

Airbnb cash on cash: 1.28%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $1482

Traditional Rental Income: $2627

Airbnb ROI: 1.28%