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: -0.19% Traditional cash on cash: 2.35% Airbnb Rental Income: $2246 Traditional Rental Income: $4006 Airbnb ROI: -0.19% Traditional ROI: 2.35%
2 Dickinson Court #2 Litchfield, CT Discover a blend of classic elegance and modern convenience in this stunning Beecher unit ...	2 beds \| 3 baths \| 1,978 sq.ft.	$525,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.31% Airbnb Rental Income: $2107 Traditional Rental Income: $3250 Airbnb ROI: -0.12% Traditional ROI: 3.31%
102 North Street Litchfield, CT Step into the pages of history with the beautifully revitalized Col. Charles Webb house, c...	3 beds \| 4 baths \| 4,888 sq.ft.	$1,875,000	Airbnb cash on cash: -2.22% Traditional cash on cash: -0.23% Airbnb Rental Income: $2246 Traditional Rental Income: $5152 Airbnb ROI: -2.22% Traditional ROI: -0.23%
25 Spruce Drive Litchfield, CT Imagine setting out to build your dream home. You find a nice lot on a hillside overlookin...	3 beds \| 4 baths \| 3,787 sq.ft.	$924,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 1.6% Airbnb Rental Income: $2246 Traditional Rental Income: $4208 Airbnb ROI: -1.33% Traditional ROI: 1.6%
258 Hunter Drive #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: -0.06% Traditional cash on cash: 3.75% Airbnb Rental Income: $2246 Traditional Rental Income: $3640 Airbnb ROI: -0.06% Traditional ROI: 3.75%
426 Torrington Road Litchfield, CT Welcome to this beautifully completely renovated meticulously maintained 1941 Cape, locate...	2 beds \| 1 baths \| 1,030 sq.ft.	$440,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.54% Airbnb Rental Income: $2107 Traditional Rental Income: $2012 Airbnb ROI: 0.46% Traditional ROI: 1.54%
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: 0.7% Traditional cash on cash: 6.94% Airbnb Rental Income: $1097 Traditional Rental Income: $1766 Airbnb ROI: 0.7% Traditional ROI: 6.94%
405 Hunter Drive #405 Litchfield, CT Now available at Hunter's Chase in Litchfield, this distinguished Pimlico-style residence,...	3 beds \| 4 baths \| 2,004 sq.ft.	$549,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 4.42% Airbnb Rental Income: $2246 Traditional Rental Income: $4574 Airbnb ROI: -1.21% Traditional ROI: 4.42%
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: 2.52% Traditional cash on cash: 9.04% Airbnb Rental Income: $2246 Traditional Rental Income: $3525 Airbnb ROI: 2.52% Traditional ROI: 9.04%
6 Kubish Road Litchfield, CT This is it! Brand-new architecture that actually gets it right. 14 private acres on a rive...	4 beds \| 4 baths \| 3,105 sq.ft.	$1,860,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 0.51% Airbnb Rental Income: $2409 Traditional Rental Income: $6381 Airbnb ROI: -2.13% Traditional ROI: 0.51%
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: 0.8% Traditional cash on cash: 5% Airbnb Rental Income: $2409 Traditional Rental Income: $3665 Airbnb ROI: 0.8% Traditional ROI: 5%
38 Old Turnpike Road Litchfield, CT An exceptional property with a rare convergence of historic provenance and modern excellen...	4 beds \| 3 baths \| 2,377 sq.ft.	$1,495,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.72% Airbnb Rental Income: $2409 Traditional Rental Income: $3441 Airbnb ROI: -1.89% Traditional ROI: -0.72%
11 West Chestnut Hill Road Litchfield, CT Period Details \| Modern Comfort \| Room to Grow Welcome home to 11 West Chestnut Hill, a r...	5 beds \| 4 baths \| 3,328 sq.ft.	$765,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 5.16% Airbnb Rental Income: $5762 Traditional Rental Income: $6001 Airbnb ROI: 3.21% Traditional ROI: 5.16%
67 Cathole Road Litchfield, CT Welcome to this charming Colonial perfectly situated in the Bantam Borough. It offers the ...	3 beds \| 2 baths \| 1,960 sq.ft.	$530,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.24% Airbnb Rental Income: $2246 Traditional Rental Income: $3245 Airbnb ROI: 0.09% Traditional ROI: 3.24%

Real Estate investment in Litchfield, CT

There are 15 properties for sale in the city of Litchfield . The median list price in Litchfield is $549,500 and the average price per square foot is $206. In December 2025, the average monthly cash on cash return in Litchfield is 3.00%. The average monthly rental income in Litchfield is $3,706.

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

There are 15 investment properties available for sale in Litchfield.

In 2025, the best neighborhood to buy investment property is Litchfield.

The ROI for Short-Term is higher than the Long-Term in Litchfield with average rental income of $2,246.

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: -0.19%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $2246

Traditional Rental Income: $4006

Airbnb ROI: -0.19%

Traditional ROI: 2.35%

2 Dickinson Court #2

Litchfield, CT

2 beds | 3 baths | 1,978 sq.ft.

$525,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2107

Traditional Rental Income: $3250

Airbnb ROI: -0.12%

Traditional ROI: 3.31%

102 North Street

Litchfield, CT

3 beds | 4 baths | 4,888 sq.ft.

$1,875,000

Airbnb cash on cash: -2.22%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $2246

Traditional Rental Income: $5152

Airbnb ROI: -2.22%

Traditional ROI: -0.23%

25 Spruce Drive

Litchfield, CT

3 beds | 4 baths | 3,787 sq.ft.

$924,000

Airbnb cash on cash: -1.33%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $2246

Traditional Rental Income: $4208

Airbnb ROI: -1.33%

Traditional ROI: 1.6%

258 Hunter Drive #258

Litchfield, CT

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

$550,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2246

Traditional Rental Income: $3640

Airbnb ROI: -0.06%

Traditional ROI: 3.75%

426 Torrington Road

Litchfield, CT

2 beds | 1 baths | 1,030 sq.ft.

$440,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $2107

Traditional Rental Income: $2012

Airbnb ROI: 0.46%

Traditional ROI: 1.54%

28 Trumbull Street

Litchfield, CT

1 beds | 1 baths | 697 sq.ft.

$175,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 6.94%

Airbnb Rental Income: $1097

Traditional Rental Income: $1766

Airbnb ROI: 0.7%

Traditional ROI: 6.94%

405 Hunter Drive #405

Litchfield, CT

3 beds | 4 baths | 2,004 sq.ft.

$549,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $2246

Traditional Rental Income: $4574

Airbnb ROI: -1.21%