Real Estate Investments for Sale in Litchfield, CT With High ROI

Are you looking for a vacation rental in Litchfield, CT? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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.

Single Family Homes for Sale in Litchfield, CT

Search for Single Family Residential for Sale in Litchfield, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 20 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
307 East Litchfield Road Litchfield, CT Fall in love with this updated vintage Cape on almost seven glorious acres with spectacula...	3 beds \| 2 baths \| 1,396 sq.ft.	$499,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 2.09% Airbnb Rental Income: $4593 Traditional Rental Income: $2523 Airbnb ROI: 4.48% Traditional ROI: 2.09%
160 Headquarters Road Litchfield, CT Enjoy peace and tranquility in this impeccably maintained contemporary located in the Milt...	3 beds \| 3 baths \| 3,291 sq.ft.	$795,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.8% Airbnb Rental Income: $4593 Traditional Rental Income: $3003 Airbnb ROI: 1.66% Traditional ROI: 0.8%
23 Bigos Road Litchfield, CT Welcome to Locust Hill Farm, a tranquil Country Retreat. Originally a dairy farm owned by ...	3 beds \| 3 baths \| 4,320 sq.ft.	$899,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.11% Airbnb Rental Income: $4593 Traditional Rental Income: $2806 Airbnb ROI: 1.11% Traditional ROI: 0.11%
142 Marsh Road Litchfield, CT Cozy four-room, two-bedroom Cape Cod on a completely private two-acre lot. Spotless origin...	2 beds \| 1 baths \| 1,082 sq.ft.	$379,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.25% Airbnb Rental Income: $2859 Traditional Rental Income: $2001 Airbnb ROI: 2.79% Traditional ROI: 2.25%
24 South Street Litchfield, CT NEWLY REFRESHED PRICE!! Location, location, location! Enjoy this holiday season in storybo...	5 beds \| 3 baths \| 3,650 sq.ft.	$1,695,000	Airbnb cash on cash: 0.63% Traditional cash on cash: -0.89% Airbnb Rental Income: $7451 Traditional Rental Income: $3619 Airbnb ROI: 0.63% Traditional ROI: -0.89%
131 Buell Road Litchfield, CT Welcome to 131 Buell Road one of Litchfield's hidden gems surrounded by Picturesque Views ...	3 beds \| 3 baths \| 2,617 sq.ft.	$739,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 1.74% Airbnb Rental Income: $4593 Traditional Rental Income: $3442 Airbnb ROI: 2.02% Traditional ROI: 1.74%
182 Cathole Road Litchfield, CT Wonderfully private, flawlessly maintained 1935 Litchfield getaway on 31.6 acres featuring...	5 beds \| 4 baths \| 3,372 sq.ft.	$1,390,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 0% Airbnb Rental Income: $7451 Traditional Rental Income: $4133 Airbnb ROI: 1.46% Traditional ROI: 0%
447 South Street Litchfield, CT Welcome to your dream home! This newly renovated five-bedroom house, located on two acres ...	5 beds \| 5 baths \| 4,750 sq.ft.	$895,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 3.03% Airbnb Rental Income: $7451 Traditional Rental Income: $5228 Airbnb ROI: 3.99% Traditional ROI: 3.03%
335 East Litchfield Road Litchfield, CT This lovely 10 room, 5 bedroom, 3 full bath home was built in 1760 âThe Alexander McNeil...	5 beds \| 3 baths \| 3,356 sq.ft.	$599,000	Airbnb cash on cash: 7.48% Traditional cash on cash: 2.91% Airbnb Rental Income: $7451 Traditional Rental Income: $3465 Airbnb ROI: 7.48% Traditional ROI: 2.91%
40 Highland Avenue Litchfield, CT TWO individual & both impeccably remodeled living spaces! Step into the main house and be ...	2 beds \| 2 baths \| 1,050 sq.ft.	$449,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 1.12% Airbnb Rental Income: $2859 Traditional Rental Income: $1874 Airbnb ROI: 1.88% Traditional ROI: 1.12%
102 North Street Litchfield, CT Introducing the Col. Charles Webb house, circa 1830 centrally located in historic Litchfie...	4 beds \| 5 baths \| 4,888 sq.ft.	$1,900,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.32% Airbnb Rental Income: $5247 Traditional Rental Income: $6182 Airbnb ROI: -0.81% Traditional ROI: 0.32%
193 South Street Litchfield, CT Utterly Charming c. 1900 Cape in mint condition set down a long driveway in a magical past...	4 beds \| 3 baths \| 2,413 sq.ft.	$1,150,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.52% Airbnb Rental Income: $5247 Traditional Rental Income: $3998 Airbnb ROI: 0.7% Traditional ROI: 0.52%
469 Milton Road Litchfield, CT A long drive leads to this lovely country Colonial with inground saltwater pool on 10.9 ac...	4 beds \| 3 baths \| 2,784 sq.ft.	$988,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 1.13% Airbnb Rental Income: $5247 Traditional Rental Income: $4011 Airbnb ROI: 1.32% Traditional ROI: 1.13%
272 Brush Hill Road Litchfield, CT ON GOLDEN POND- This one-of-a-kind home sits directly on Floren Pond and you canât get a...	3 beds \| 4 baths \| 3,143 sq.ft.	$1,525,000	Airbnb cash on cash: -0.63% Traditional cash on cash: -1.07% Airbnb Rental Income: $4593 Traditional Rental Income: $3019 Airbnb ROI: -0.63% Traditional ROI: -1.07%
171 South Street Litchfield, CT 1898 carriage house on 3+ acres with Bantam river water frontage and access to White Memor...	4 beds \| 4 baths \| 4,346 sq.ft.	$1,695,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 1.62% Airbnb Rental Income: $5247 Traditional Rental Income: $5438 Airbnb ROI: 0.82% Traditional ROI: 1.62%
255 South Street Litchfield, CT Impeccably maintained historic district home is close to town and all its amenities includ...	4 beds \| 2 baths \| 2,537 sq.ft.	$699,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 3.76% Airbnb Rental Income: $5247 Traditional Rental Income: $3772 Airbnb ROI: 4.39% Traditional ROI: 3.76%
85 East Litchfield Road Litchfield, CT Newly updated and move-in ready four bedroom cottage on .9 acre just minutes to historic L...	4 beds \| 2 baths \| 1,790 sq.ft.	$475,000	Airbnb cash on cash: 7.23% Traditional cash on cash: 5.25% Airbnb Rental Income: $5247 Traditional Rental Income: $3304 Airbnb ROI: 7.23% Traditional ROI: 5.25%
5 Maple View Trail Litchfield, CT Let the designer in you run with abandon as you plan the design of this new home. Options ...	4 beds \| 3 baths \| 2,436 sq.ft.	$749,900	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.76% Airbnb Rental Income: $5247 Traditional Rental Income: $4307 Airbnb ROI: 4.59% Traditional ROI: 4.76%
80 Circle Drive Litchfield, CT Welcome to 80 Circle Dr! This ranch has over 2,236 sqft of living space and is less than a...	4 beds \| 3 baths \| 2,236 sq.ft.	$440,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.89% Airbnb Rental Income: $5247 Traditional Rental Income: $3245 Airbnb ROI: 8.17% Traditional ROI: 5.89%

Your search for investment property begins and ends here

Single Family Homes for Sale in Litchfield, CT

307 East Litchfield Road

Litchfield, CT

3 beds | 2 baths | 1,396 sq.ft.

$499,000

Airbnb cash on cash: 4.48%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $4593

Traditional Rental Income: $2523

Airbnb ROI: 4.48%

Traditional ROI: 2.09%

160 Headquarters Road

Litchfield, CT

3 beds | 3 baths | 3,291 sq.ft.

$795,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $4593

Traditional Rental Income: $3003

Airbnb ROI: 1.66%

Traditional ROI: 0.8%

23 Bigos Road

Litchfield, CT

3 beds | 3 baths | 4,320 sq.ft.

$899,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $4593

Traditional Rental Income: $2806

Airbnb ROI: 1.11%

Traditional ROI: 0.11%

142 Marsh Road

Litchfield, CT

2 beds | 1 baths | 1,082 sq.ft.

$379,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2859

Traditional Rental Income: $2001

Airbnb ROI: 2.79%

Traditional ROI: 2.25%

24 South Street

Litchfield, CT

5 beds | 3 baths | 3,650 sq.ft.

$1,695,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $7451

Traditional Rental Income: $3619

Airbnb ROI: 0.63%

Traditional ROI: -0.89%

131 Buell Road

Litchfield, CT

3 beds | 3 baths | 2,617 sq.ft.

$739,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 1.74%

Airbnb Rental Income: $4593

Traditional Rental Income: $3442

Airbnb ROI: 2.02%

Traditional ROI: 1.74%

182 Cathole Road

Litchfield, CT

5 beds | 4 baths | 3,372 sq.ft.

$1,390,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 0%

Airbnb Rental Income: $7451

Traditional Rental Income: $4133

Airbnb ROI: 1.46%

Traditional ROI: 0%

447 South Street

Litchfield, CT

5 beds | 5 baths | 4,750 sq.ft.

$895,000

Airbnb cash on cash: 3.99%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $7451

Traditional Rental Income: $5228

Airbnb ROI: 3.99%