Real Estate Investment Properties for Sale in Thomaston, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
341 High St Ext Thomaston, CT Hidden Estate at High Street: A private Litchfield County retreat offering relaxed country...	4 beds \| 4 baths \| 5,729 sq.ft.	$800,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 7.75% Airbnb Rental Income: $3214 Traditional Rental Income: $8241 Airbnb ROI: 0.03% Traditional ROI: 7.75%
99 Pine Hill Rd Thomaston, CT Investors! Flippers! Take Notice! This 5 room Ranch style home features spacious living ro...	3 beds \| 1 baths \| 1,032 sq.ft.	$289,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.27% Airbnb Rental Income: $1564 Traditional Rental Income: $1563 Airbnb ROI: 1.68% Traditional ROI: 3.27%
162 Bristol St Thomaston, CT With some TLC and hard work you could turn this adorable cape into your home! You'll see t...	2 beds \| 1 baths \| 1,062 sq.ft.	$309,900	Airbnb cash on cash: 0.24% Traditional cash on cash: 4.54% Airbnb Rental Income: $1549 Traditional Rental Income: $2395 Airbnb ROI: 0.24% Traditional ROI: 4.54%
96 Elm St Thomaston, CT Roll up your sleeves and get to work ! This Classic Colonial was built in1850 per town re...	4 beds \| 2 baths \| 1,705 sq.ft.	$399,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 5.28% Airbnb Rental Income: $3214 Traditional Rental Income: $3235 Airbnb ROI: 3.29% Traditional ROI: 5.28%
1092 Hickory Hill Rd Thomaston, CT 1092 Hickory Hill Rd, Thomaston, CT 06787 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 5.04% Airbnb Rental Income: $1083 Traditional Rental Income: $874 Airbnb ROI: 3.37% Traditional ROI: 5.04%
156 Litchfield St Thomaston, CT Charming updated home close to town with exceptional curb appeal!! This 3 bedroom 1 bath h...	3 beds \| 1 baths \| 1,001 sq.ft.	$269,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 5.11% Airbnb Rental Income: $1564 Traditional Rental Income: $2010 Airbnb ROI: 1.58% Traditional ROI: 5.11%
81 E Main Street Thomaston, CT Mixed use building on a busy high traffic road in the center of Thomaston. Two residential...	5 beds \| 3 baths \| 2,872 sq.ft.	$450,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 7.72% Airbnb Rental Income: $1866 Traditional Rental Income: $4250 Airbnb ROI: 0.87% Traditional ROI: 7.72%
88 Tracy St Thomaston, CT Colonial style home with detached garage and an additional building lot to the right of th...	3 beds \| 1 baths \| 1,488 sq.ft.	$359,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 5.92% Airbnb Rental Income: $1564 Traditional Rental Income: $2996 Airbnb ROI: 0.35% Traditional ROI: 5.92%
261 Litchfield St Thomaston, CT 261 Litchfield St, Thomaston, CT 06787 \| Other	N/A beds \| N/A baths \| N/A	$95,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.29% Airbnb Rental Income: $1083 Traditional Rental Income: $959 Airbnb ROI: 3.64% Traditional ROI: 6.29%
400 Northfield Rd Thomaston, CT 400 Northfield Rd, Thomaston, CT 06787 \| Other	N/A beds \| N/A baths \| N/A	$95,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.29% Airbnb Rental Income: $1083 Traditional Rental Income: $959 Airbnb ROI: 3.64% Traditional ROI: 6.29%
53 Broadview Hts Thomaston, CT 53 Broadview Hts, Thomaston, CT 06787 \| Single Family Residential	4 beds \| 2 baths \| 1,568 sq.ft.	$339,900	Airbnb cash on cash: 3.44% Traditional cash on cash: 5.06% Airbnb Rental Income: $3214 Traditional Rental Income: $3081 Airbnb ROI: 3.44% Traditional ROI: 5.06%
57 Hickory Hill Rd Thomaston, CT 57 Hickory Hill Rd, Thomaston, CT 06787 \| Single Family Residential	2 beds \| 1 baths \| 1,249 sq.ft.	$385,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.03% Airbnb Rental Income: $1549 Traditional Rental Income: $1592 Airbnb ROI: -0.32% Traditional ROI: 1.03%
220 Jackson St Thomaston, CT 220 Jackson St, Thomaston, CT 06787 \| Single Family Residential	5 beds \| 2 baths \| 2,814 sq.ft.	$599,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.57% Airbnb Rental Income: $1866 Traditional Rental Income: $3282 Airbnb ROI: -0.85% Traditional ROI: 2.57%
310 Carter Rd Thomaston, CT Welcome to this exceptional private retreat, situated on nearly 12 secluded acres. Enter t...	3 beds \| 2 baths \| 2,970 sq.ft.	$750,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2.69% Airbnb Rental Income: $1564 Traditional Rental Income: $3919 Airbnb ROI: -1.33% Traditional ROI: 2.69%
230 Reynolds Bridge Rd Thomaston, CT 230 Reynolds Bridge Rd, Thomaston, CT 06787 \| Single Family Residential	3 beds \| 1 baths \| 1,425 sq.ft.	$324,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 2.88% Airbnb Rental Income: $1564 Traditional Rental Income: $1950 Airbnb ROI: 0.18% Traditional ROI: 2.88%
98 Edgewood Ave Thomaston, CT 98 Edgewood Ave, Thomaston, CT 06787 \| Single Family Residential	3 beds \| 1 baths \| 1,224 sq.ft.	$337,900	Airbnb cash on cash: 0.1% Traditional cash on cash: 2.51% Airbnb Rental Income: $1564 Traditional Rental Income: $1880 Airbnb ROI: 0.1% Traditional ROI: 2.51%
377 E Main St Thomaston, CT 377 E Main St, Thomaston, CT 06787 \| Multi Family	4 beds \| 2 baths \| 1,786 sq.ft.	$329,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 7.62% Airbnb Rental Income: $1564 Traditional Rental Income: $3420 Airbnb ROI: 0.18% Traditional ROI: 7.62%
211 Cedar Mountain Road Thomaston, CT Set majestically on .92 acres in a highly desirable neighborhood, this tastefully updated ...	3 beds \| 3 baths \| 2,144 sq.ft.	$499,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 5.07% Airbnb Rental Income: $1564 Traditional Rental Income: $3694 Airbnb ROI: -0.45% Traditional ROI: 5.07%
170 Valley View Road Thomaston, CT Welcome to this impressive Colonial home set in a quiet, highly sought-after area of histo...	4 beds \| 3 baths \| 2,857 sq.ft.	$695,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.01% Airbnb Rental Income: $3214 Traditional Rental Income: $4453 Airbnb ROI: 0.98% Traditional ROI: 4.01%

Real Estate investment in Thomaston, CT

There are 24 properties for sale in the city of Thomaston . The median list price in Thomaston is $339,797 and the average price per square foot is $207. In August 2026, the average monthly cash on cash return in Thomaston is 5.00%. The average monthly rental income in Thomaston is $2,696.

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

There are 24 investment properties available for sale in Thomaston.

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

The ROI for Long-Term is higher than the Short-Term in Thomaston with average rental income of $2,696.

Your search for investment property begins and ends here

Investment Property for Sale in Thomaston, CT

341 High St Ext

Thomaston, CT

4 beds | 4 baths | 5,729 sq.ft.

$800,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $3214

Traditional Rental Income: $8241

Airbnb ROI: 0.03%

Traditional ROI: 7.75%

99 Pine Hill Rd

Thomaston, CT

3 beds | 1 baths | 1,032 sq.ft.

$289,900

Airbnb cash on cash: 1.68%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1564

Traditional Rental Income: $1563

Airbnb ROI: 1.68%

Traditional ROI: 3.27%

162 Bristol St

Thomaston, CT

2 beds | 1 baths | 1,062 sq.ft.

$309,900

Airbnb cash on cash: 0.24%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $1549

Traditional Rental Income: $2395

Airbnb ROI: 0.24%

Traditional ROI: 4.54%

96 Elm St

Thomaston, CT

4 beds | 2 baths | 1,705 sq.ft.

$399,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $3214

Traditional Rental Income: $3235

Airbnb ROI: 3.29%

Traditional ROI: 5.28%

1092 Hickory Hill Rd

Thomaston, CT

N/A beds | N/A baths | N/A

$99,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $1083

Traditional Rental Income: $874

Airbnb ROI: 3.37%

Traditional ROI: 5.04%

156 Litchfield St

Thomaston, CT

3 beds | 1 baths | 1,001 sq.ft.

$269,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $1564

Traditional Rental Income: $2010

Airbnb ROI: 1.58%

Traditional ROI: 5.11%

81 E Main Street

Thomaston, CT

5 beds | 3 baths | 2,872 sq.ft.

$450,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 7.72%

Airbnb Rental Income: $1866

Traditional Rental Income: $4250

Airbnb ROI: 0.87%

Traditional ROI: 7.72%

88 Tracy St

Thomaston, CT

3 beds | 1 baths | 1,488 sq.ft.

$359,900

Airbnb cash on cash: 0.35%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $1564

Traditional Rental Income: $2996

Airbnb ROI: 0.35%