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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
26 Seminole Cir #26Litchfield, CTWelcome to Litchfield's only active adult community for those 55 years of age. This Washi... |
2 beds | 2 baths | 1,940 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.74%
|
34 Highland AveLitchfield, CTWelcoming and charming. Two fitting words to describe this special home. One will find a ... |
3 beds | 1 baths | 1,268 sq.ft. |
$378,000 |
Airbnb cash on cash: 4.56%
|
26 Seminole CirLitchfield, CTIndian Knolls offers beautifully landscaped grounds and stylish home designs that create a... |
2 beds | 2 baths | 1,940 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.67%
|
63 Cathole RdLitchfield, CT63 Cathole Rd, Litchfield, CT 06750 | Single Family Residential |
2 beds | 1 baths | 944 sq.ft. |
$360,000 |
Airbnb cash on cash: 1.03%
|
28 Trumbull StreetLitchfield, CTSIGNIFICANT 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: 4.35%
|
28 Headquarters RdLitchfield, CTStimulating 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: 0.45%
|
234 East StLitchfield, CTVery charming bungalow Cape with beautifully landscaped yard and tandem 2 car garage with ... |
3 beds | 2 baths | 1,318 sq.ft. |
$359,999 |
Airbnb cash on cash: 4.83%
|
212 Old South RdLitchfield, CTMIDCENTURY OASIS MEETS CONSERVATION SANCTUARY: A mid-summers "White" Dream! For those who ... |
3 beds | 2 baths | 1,572 sq.ft. |
$679,000 |
Airbnb cash on cash: 1.61%
|
85 E Litchfield RdLitchfield, CTThis beautifully fully renovated four-bedroom Colonial, set on just under an acre, offers ... |
4 beds | 2 baths | 1,790 sq.ft. |
$425,000 |
Airbnb cash on cash: 2.64%
|
476 Milton RdLitchfield, CTBuyerâs buyer got cold feet. Fabulous California Contemporary "Scarsdale Hi Ranch" w/ 2.... |
3 beds | 1 baths | 1,864 sq.ft. |
$450,000 |
Airbnb cash on cash: 3.31%
|
171 South StLitchfield, CT1898 carriage house on 3+ acres with Bantam river water frontage and access to White Memor... |
4 beds | 3 baths | 4,346 sq.ft. |
$2,395,000 |
Airbnb cash on cash: -0.7%
|
447 South StLitchfield, CTWelcome to your dream home! This newly renovated five-bedroom house, located on two acres ... |
5 beds | 3 baths | 4,762 sq.ft. |
$1,775,000 |
Airbnb cash on cash: -1.64%
|
107 Clark RdLitchfield, CTThe warmth of the natural light invites you sit on the expansive deck and feel the gentle ... |
6 beds | 4 baths | 3,034 sq.ft. |
$1,673,000 |
Airbnb cash on cash: -1.55%
|
67 E Litchfield Rd SLitchfield, CTNestled in a serene rural neighborhood, this delightful 2-bedroom wood shingle home offers... |
2 beds | 1 baths | 1,104 sq.ft. |
$315,000 |
Airbnb cash on cash: 1.62%
|
258 Hunter Dr #258Litchfield, CTLive in fabled Litchfield with few home ownership cares and at the most reasonable expense... |
3 beds | 2 baths | 2,526 sq.ft. |
$535,000 |
Airbnb cash on cash: 1.26%
|
168 Fern AveLitchfield, CTFern House, a luxurious countryside estate with 4 bedrooms 3.5 baths, 3 Stall Horse Barn, ... |
4 beds | 3 baths | 3,614 sq.ft. |
$1,499,000 |
Airbnb cash on cash: -1.78%
|
6 Kubish RdLitchfield, CTBrand-new architecture that actually gets it right. 10+ private acres on a river in Litchf... |
4 beds | 3 baths | 3,105 sq.ft. |
$1,000,000 |
Airbnb cash on cash: -0.16%
|
184 Fern AveLitchfield, CT184 Fern Ave, Litchfield, CT 06759 | Single Family Residential |
8 beds | 9 baths | 10,516 sq.ft. |
$3,950,000 |
Airbnb cash on cash: -2.46%
|
0 Decker DrLitchfield, CT0 Decker Dr, Litchfield, CT 06759 | Other |
N/A beds | N/A baths | N/A |
$99,900 |
Airbnb cash on cash: N/A
|
Reder RdLitchfield, CTReder Rd, Litchfield, CT 06759 | Other |
N/A beds | N/A baths | N/A |
$129,000 |
Airbnb cash on cash: N/A
|
Wheeler RdLitchfield, CTWheeler Rd, Litchfield, CT 06759 | Other |
N/A beds | N/A baths | 2,456 sq.ft. |
$225,000 |
Airbnb cash on cash: N/A
|
19 Seherr Thoss DrLitchfield, CT19 Seherr Thoss Dr, Litchfield, CT 06759 | Single Family Residential |
7 beds | 6 baths | 13,056 sq.ft. |
$7,400,000 |
Airbnb cash on cash: -2.78%
|
0 Newcomb RdLitchfield, CT0 Newcomb Rd, Litchfield, CT 06759 | Other |
N/A beds | N/A baths | N/A |
$340,000 |
Airbnb cash on cash: N/A
|
88 Knox RdLitchfield, CT88 Knox Rd, Litchfield, CT 06759 | Single Family Residential |
3 beds | 2 baths | 1,391 sq.ft. |
$609,000 |
Airbnb cash on cash: 0.89%
|
148 North StLitchfield, CT148 North St, Litchfield, CT 06759 | Single Family Residential |
7 beds | 5 baths | 6,641 sq.ft. |
$3,500,000 |
Airbnb cash on cash: -2.37%
|
222 Old South RdLitchfield, CT222 Old South Rd, Litchfield, CT 06759 | Single Family Residential |
4 beds | 3 baths | 2,666 sq.ft. |
$499,000 |
Airbnb cash on cash: 0.91%
|
34 Highland AveLitchfield, CT34 Highland Ave, Litchfield, CT 06759 | Single Family Residential |
3 beds | 1 baths | 1,268 sq.ft. |
$395,000 |
Airbnb cash on cash: 3.05%
|
424 South StLitchfield, CT424 South St, Litchfield, CT 06759 | Single Family Residential |
3 beds | 2 baths | 1,462 sq.ft. |
$389,900 |
Airbnb cash on cash: 3.13%
|
39 Tapping Reeve Vlg #39Litchfield, CT39 Tapping Reeve Vlg #39, Litchfield, CT 06759 | Condo/Coop |
3 beds | 2 baths | 1,200 sq.ft. |
$295,000 |
Airbnb cash on cash: 3.47%
|
366 Torrington RdLitchfield, CT366 Torrington Rd, Litchfield, CT 06759 | Multi Family |
3 beds | 2 baths | 1,708 sq.ft. |
$379,000 |
Airbnb cash on cash: 3.3%
|
336 Maple StLitchfield, CT336 Maple St, Litchfield, CT 06759 | Single Family Residential |
2 beds | 2 baths | 1,984 sq.ft. |
$545,000 |
Airbnb cash on cash: -0.37%
|
31 Wheeler RdLitchfield, CT31 Wheeler Rd, Litchfield, CT 06759 | Single Family Residential |
3 beds | 2 baths | 1,104 sq.ft. |
$385,000 |
Airbnb cash on cash: 3.2%
|
53 Prospect Mountain RdLitchfield, CT53 Prospect Mountain Rd, Litchfield, CT 06759 | Single Family Residential |
3 beds | 2 baths | 1,919 sq.ft. |
$520,000 |
Airbnb cash on cash: 1.57%
|
287 Prospect Mountain RdLitchfield, CT287 Prospect Mountain Rd, Litchfield, CT 06759 | Single Family Residential |
5 beds | 5 baths | 5,861 sq.ft. |
$3,690,000 |
Airbnb cash on cash: -2.41%
|
14 Meadow Ridge RdLitchfield, CT14 Meadow Ridge Rd, Litchfield, CT 06759 | Single Family Residential |
3 beds | 1 baths | 1,040 sq.ft. |
$299,900 |
Airbnb cash on cash: 4.97%
|
329 Norfolk RdLitchfield, CT329 Norfolk Rd, Litchfield, CT 06759 | Single Family Residential |
3 beds | 2 baths | 2,039 sq.ft. |
$639,000 |
Airbnb cash on cash: 0.7%
|
162 Hutchinson & Mike Road PkwyLitchfield, CT162 Hutchinson & Mike Road Pkwy, Litchfield, CT 06759 | Single Family Residential |
5 beds | 4 baths | 4,145 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -2.07%
|
351 Hunter Dr #351Litchfield, CT351 Hunter Dr #351, Litchfield, CT 06759 | Condo/Coop |
3 beds | 3 baths | 3,020 sq.ft. |
$749,000 |
Airbnb cash on cash: -0.76%
|
631 S Plains RdLitchfield, CT631 S Plains Rd, Litchfield, CT 06759 | Other |
N/A beds | N/A baths | N/A |
$640,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Litchfield, CT
There are 65 properties for sale in the city of Litchfield . The median list price in Litchfield is $999,339 and the average price per square foot is $376. In October 2026, the average monthly cash on cash return in Litchfield is 2.00%. The average monthly rental income in Litchfield is $2,756.