Real Estate Investment Properties for Sale in Litchfield, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
28 Headquarters Road Litchfield, CT Stimulating and easily managed home is perfect for weekending in an idyllic, small, histor...	3 beds \| 3 baths \| 3,225 sq.ft.	$985,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 2.25% Airbnb Rental Income: $2246 Traditional Rental Income: $4006 Airbnb ROI: -0.28% Traditional ROI: 2.25%
250 Hunter Drive unit: 250 #250 Litchfield, CT Nestled within 77 country acres in the distinguished town of Litchfield, Hunter's Chase st...	3 beds \| 4 baths \| 2,629 sq.ft.	$599,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 5.18% Airbnb Rental Income: $2246 Traditional Rental Income: $4826 Airbnb ROI: -0.44% Traditional ROI: 5.18%
258 Hunter Drive unit: 258 #258 Litchfield, CT Live in fabled Litchfield with few home ownership cares and at the most reasonable expense...	3 beds \| 3 baths \| 2,526 sq.ft.	$550,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.69% Airbnb Rental Income: $2246 Traditional Rental Income: $3640 Airbnb ROI: -0.12% Traditional ROI: 3.69%
28 Trumbull Street Litchfield, CT SIGNIFICANT PRICE REDUCTION! The entire western border of this property is on the Bantam R...	1 beds \| 1 baths \| 697 sq.ft.	$175,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 7.18% Airbnb Rental Income: $1097 Traditional Rental Income: $1766 Airbnb ROI: 0.93% Traditional ROI: 7.18%
405 Hunter Drive unit: 405 #405 Litchfield, CT Now available at Hunter's Chase in Litchfield, this distinguished Pimlico-style residence,...	3 beds \| 4 baths \| 2,867 sq.ft.	$549,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 5.47% Airbnb Rental Income: $2246 Traditional Rental Income: $4574 Airbnb ROI: -0.17% Traditional ROI: 5.47%
552 Milton Road Litchfield, CT This stately 1800s victorian on 2 acres in the heart of Milton is ready to be restored! Ju...	3 beds \| 2 baths \| 2,392 sq.ft.	$300,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 9.24% Airbnb Rental Income: $2246 Traditional Rental Income: $3525 Airbnb ROI: 2.71% Traditional ROI: 9.24%
31 Main Street Litchfield, CT TIMELESS CHARM in the Northfield section of Litchfield. Step into this spotless, move-in-r...	4 beds \| 3 baths \| 1,873 sq.ft.	$470,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 5.89% Airbnb Rental Income: $2409 Traditional Rental Income: $3665 Airbnb ROI: 1.7% Traditional ROI: 5.89%
38 Old Turnpike Road Litchfield, CT An exceptional property with a rare convergence of historic provenance and modern excellen...	3 beds \| 3 baths \| 2,377 sq.ft.	$1,495,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.77% Airbnb Rental Income: $2246 Traditional Rental Income: $3441 Airbnb ROI: -0.49% Traditional ROI: 0.77%
11 W Chestnut Hill Road Litchfield, CT Period Details \| Modern Comfort \| Room to Grow Welcome home to 11 West Chestnut Hill, a re...	5 beds \| 4 baths \| 3,328 sq.ft.	$765,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 6.11% Airbnb Rental Income: $5762 Traditional Rental Income: $6001 Airbnb ROI: 4.17% Traditional ROI: 6.11%
415 South Street Litchfield, CT Welcome to Riverbend Farm, a beautiful 9 acres (over two lots) located on the Bantam River...	4 beds \| 5 baths \| 4,152 sq.ft.	$1,695,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.11% Airbnb Rental Income: $2409 Traditional Rental Income: $9104 Airbnb ROI: -0.52% Traditional ROI: 4.11%
161 Circle Drive Litchfield, CT A well-maintained duplex at 161 Circle Drive offers an excellent investment opportunity in...	4 beds \| 2 baths \| 1,430 sq.ft.	$349,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 7.12% Airbnb Rental Income: $2409 Traditional Rental Income: $3040 Airbnb ROI: 3.4% Traditional ROI: 7.12%
204 Goodhouse Road Litchfield, CT This charming Ranch located on a beautiful country road is ready for its next chapter afte...	4 beds \| 2 baths \| 1,794 sq.ft.	$395,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 6.56% Airbnb Rental Income: $2409 Traditional Rental Income: $3351 Airbnb ROI: 2.42% Traditional ROI: 6.56%

Real Estate investment in Litchfield, CT

There are 16 properties for sale in the city of Litchfield . The median list price in Litchfield is $525,000 and the average price per square foot is $227. In January 2026, the average monthly cash on cash return in Litchfield is 5.00%. The average monthly rental income in Litchfield is $3,653.

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

There are 16 investment properties available for sale in Litchfield.

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

The ROI for Long-Term is higher than the Short-Term in Litchfield with average rental income of $3,653.

Your search for investment property begins and ends here

Investment Property for Sale in Litchfield, CT

28 Headquarters Road

Litchfield, CT

3 beds | 3 baths | 3,225 sq.ft.

$985,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2246

Traditional Rental Income: $4006

Airbnb ROI: -0.28%

Traditional ROI: 2.25%

250 Hunter Drive unit: 250 #250

Litchfield, CT

3 beds | 4 baths | 2,629 sq.ft.

$599,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $2246

Traditional Rental Income: $4826

Airbnb ROI: -0.44%

Traditional ROI: 5.18%

258 Hunter Drive unit: 258 #258

Litchfield, CT

3 beds | 3 baths | 2,526 sq.ft.

$550,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2246

Traditional Rental Income: $3640

Airbnb ROI: -0.12%

Traditional ROI: 3.69%

28 Trumbull Street

Litchfield, CT

1 beds | 1 baths | 697 sq.ft.

$175,000

Airbnb cash on cash: 0.93%

Traditional cash on cash: 7.18%

Airbnb Rental Income: $1097

Traditional Rental Income: $1766

Airbnb ROI: 0.93%

Traditional ROI: 7.18%

405 Hunter Drive unit: 405 #405

Litchfield, CT

3 beds | 4 baths | 2,867 sq.ft.

$549,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $2246

Traditional Rental Income: $4574

Airbnb ROI: -0.17%

Traditional ROI: 5.47%

552 Milton Road

Litchfield, CT

3 beds | 2 baths | 2,392 sq.ft.

$300,000

Airbnb cash on cash: 2.71%

Traditional cash on cash: 9.24%

Airbnb Rental Income: $2246

Traditional Rental Income: $3525

Airbnb ROI: 2.71%

Traditional ROI: 9.24%

31 Main Street

Litchfield, CT

4 beds | 3 baths | 1,873 sq.ft.

$470,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $2409

Traditional Rental Income: $3665

Airbnb ROI: 1.7%

Traditional ROI: 5.89%

38 Old Turnpike Road

Litchfield, CT

3 beds | 3 baths | 2,377 sq.ft.

$1,495,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $2246

Traditional Rental Income: $3441

Airbnb ROI: -0.49%