Real Estate Investment Properties for Sale in Middletown, CT
Looking for investment property in Middletown, CT with high ROI ?
Explore a variety of short-term homes & houses in Middletown, CT. Invest wisely with VRBO & Middletown, 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 Middletown, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
142 Crystal Lake RoadMIDDLETOWN, CTLAKESIDE LIVING ON CRYSTAL LAKE! Welcome to 142 Crystal Lake Road, where everyday living f... |
2 beds | 1 baths | 1,188 sq.ft. |
$369,900 |
Airbnb cash on cash: 0.73%
|
12 Woodlot LnMIDDLETOWN, CTFully Renovated & Updated! MOVE IN READY! The main level features a STUNNING NEW KITCHEN... |
3 beds | 1 baths | 1,196 sq.ft. |
$275,000 |
Airbnb cash on cash: 2.86%
|
25 Wanda LnMIDDLETOWN, CT***PRICE REDUCED*** Beautiful home in a terrific neighborhood. This home features remodele... |
4 beds | 2 baths | 2,226 sq.ft. |
$599,000 |
Airbnb cash on cash: N/A
|
17 E Lake PlaceMIDDLETOWN, CT***Seller is ready for the next chapter and welcomes reasonable offers*** Welcome home to ... |
3 beds | 2 baths | 1,164 sq.ft. |
$329,000 |
Airbnb cash on cash: 2.22%
|
526 Boston RoadMIDDLETOWN, CTImagine waking up, brewing your first cup of coffee and looking out your kitchen window at... |
3 beds | 2 baths | 1,571 sq.ft. |
$429,900 |
Airbnb cash on cash: 0.76%
|
32 Autumn Lane #32MIDDLETOWN, CTWhat a beautiful opportunity to own in Autumn Meadows, a 55+ community in bustling Middlet... |
3 beds | 3 baths | 2,186 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.23%
|
63 Millbrook RoadMIDDLETOWN, CTWelcome to this inviting contemporary-style single-family home offering 3 bedrooms, 2 full... |
3 beds | 2 baths | 1,963 sq.ft. |
$385,000 |
Airbnb cash on cash: 0.85%
|
42 Saybrook RdMIDDLETOWN, CT42 Saybrook Rd, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 2 baths | 1,704 sq.ft. |
$339,900 |
Airbnb cash on cash: N/A
|
137 Webster Ln #2-42MIDDLETOWN, CT137 Webster Ln #2-42, MIDDLETOWN, CT 06457 | Single Family Residential |
2 beds | 2 baths | 1,430 sq.ft. |
$589,900 |
Airbnb cash on cash: -1.97%
|
0 Bell StMIDDLETOWN, CT0 Bell St, MIDDLETOWN, CT 06457 | Other |
N/A beds | N/A baths | N/A |
$100,000 |
Airbnb cash on cash: N/A
|
0 Middle StMIDDLETOWN, CT0 Middle St, MIDDLETOWN, CT 06457 | Other |
N/A beds | N/A baths | N/A |
$350,000 |
Airbnb cash on cash: N/A
|
404 Newfield StMIDDLETOWN, CTWelcome to this beautiful fully updated 3-bedroom 2 full bath ranch offering the perfect b... |
3 beds | 3 baths | 1,332 sq.ft. |
$450,000 |
Airbnb cash on cash: 1%
|
145 Monarca DrMIDDLETOWN, CT145 Monarca Dr, MIDDLETOWN, CT 06457 | Single Family Residential |
3 beds | 3 baths | 3,456 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -1.84%
|
0 Scovill RdMIDDLETOWN, CT0 Scovill Rd, MIDDLETOWN, CT 06457 | Other |
N/A beds | N/A baths | N/A |
$950,000 |
Airbnb cash on cash: N/A
|
492 Long Hill RdMIDDLETOWN, CTWelcome home to this beautifully renovated 3-bedroom, 2-bathroom raised ranch in Wesleyan ... |
3 beds | 2 baths | 1,536 sq.ft. |
$379,900 |
Airbnb cash on cash: 0.86%
|
65 Highland AveMIDDLETOWN, CT65 Highland Ave, MIDDLETOWN, CT 06457 | Single Family Residential |
3 beds | 2 baths | 1,793 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.71%
|
1409 Millbrook RdMIDDLETOWN, CT1409 Millbrook Rd, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 3 baths | 2,656 sq.ft. |
$1,295,000 |
Airbnb cash on cash: N/A
|
194 Liberty StMIDDLETOWN, CT194 Liberty St, MIDDLETOWN, CT 06457 | Multi Family |
7 beds | 2 baths | 2,476 sq.ft. |
$390,000 |
Airbnb cash on cash: -0.31%
|
201 College St #20MIDDLETOWN, CT201 College St #20, MIDDLETOWN, CT 06457 | Condo/Coop |
2 beds | 1 baths | 1,150 sq.ft. |
$179,900 |
Airbnb cash on cash: 0.68%
|
104 Higby RdMIDDLETOWN, CT104 Higby Rd, MIDDLETOWN, CT 06457 | Single Family Residential |
3 beds | 1 baths | 1,112 sq.ft. |
$399,999 |
Airbnb cash on cash: 0.7%
|
166 McCormick LnMIDDLETOWN, CT166 McCormick Ln, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 2 baths | 2,876 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
675 Newfield St #9MIDDLETOWN, CT675 Newfield St #9, MIDDLETOWN, CT 06457 | Condo/Coop |
2 beds | 1 baths | 1,223 sq.ft. |
$257,000 |
Airbnb cash on cash: -0.32%
|
104 Bell StMIDDLETOWN, CT104 Bell St, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 2 baths | 1,352 sq.ft. |
$415,000 |
Airbnb cash on cash: N/A
|
20 Chimney Hill RdMIDDLETOWN, CT20 Chimney Hill Rd, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 2 baths | 4,271 sq.ft. |
$649,000 |
Airbnb cash on cash: N/A
|
1511 Country Club RoadMIDDLETOWN, CTWelcome to 1511 Country Club Road, a remarkably versatile property offering 4-bedroom func... |
4 beds | 2 baths | 3,319 sq.ft. |
$410,000 |
Airbnb cash on cash: N/A
|
UNIT 2-41 Webster Ln #145MIDDLETOWN, CTUNIT 2-41 Webster Ln #145, MIDDLETOWN, CT 06457 | Single Family Residential |
2 beds | 2 baths | 1,555 sq.ft. |
$689,000 |
Airbnb cash on cash: -2.13%
|
122 Newfield St #3AMIDDLETOWN, CT122 Newfield St #3A, MIDDLETOWN, CT 06457 | Condo/Coop |
3 beds | 1 baths | 1,346 sq.ft. |
$329,900 |
Airbnb cash on cash: 0.43%
|
85 Freeman RdMIDDLETOWN, CT85 Freeman Rd, MIDDLETOWN, CT 06457 | Single Family Residential |
4 beds | 2 baths | 2,232 sq.ft. |
$749,900 |
Airbnb cash on cash: N/A
|
500 Washington St #9MIDDLETOWN, CT500 Washington St #9, MIDDLETOWN, CT 06457 | Single Family Residential |
1 beds | 1 baths | 533 sq.ft. |
$119,000 |
Airbnb cash on cash: -3.57%
|
130 Spencer DrMIDDLETOWN, CT130 Spencer Dr, MIDDLETOWN, CT 06457 | Single Family Residential |
5 beds | 2 baths | 1,440 sq.ft. |
$349,000 |
Airbnb cash on cash: N/A
|
46 Meech RoadMIDDLETOWN, CTCute 3-bedroom Cape with loads of potential! The spacious living room features a cozy fire... |
3 beds | 2 baths | 1,267 sq.ft. |
$245,000 |
Airbnb cash on cash: 3.08%
|
277 Carriage Crossing Ln #277MIDDLETOWN, CT277 Carriage Crossing Ln #277, MIDDLETOWN, CT 06457 | Condo/Coop |
1 beds | 1 baths | 760 sq.ft. |
$220,000 |
Airbnb cash on cash: -2.79%
|
606 Congdon St W #6MIDDLETOWN, CT606 Congdon St W #6, MIDDLETOWN, CT 06457 | Condo/Coop |
2 beds | 2 baths | 1,432 sq.ft. |
$279,900 |
Airbnb cash on cash: -0.4%
|
23 Brookview LnMIDDLETOWN, CT23 Brookview Ln, MIDDLETOWN, CT 06457 | Single Family Residential |
3 beds | 2 baths | 2,252 sq.ft. |
$605,000 |
Airbnb cash on cash: -0.59%
|
74 Grove StMIDDLETOWN, CT74 Grove St, MIDDLETOWN, CT 06457 | Multi Family |
4 beds | 2 baths | 2,035 sq.ft. |
$365,000 |
Airbnb cash on cash: 1.07%
|
85 Oakcliff RoadMIDDLETOWN, CTWelcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable... |
4 beds | 3 baths | 1,908 sq.ft. |
$555,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Middletown, CT
There are 84 properties for sale in the city of Middletown . The median list price in Middletown is $377,320 and the average price per square foot is $227. In November 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,371.