Winchester, MA Investment Properties for Sale
Browse homes for sale and investment properties in Winchester, MA. Refine your search by price, property type, or more.
Best cash flowing properties in Winchester, MA
Active
$1,379,000
5
bds
|
2
ba
|
3,033
sqft
|
built
1957
7 Thornberry Rd, Winchester, MA 01890
$-3,117
Cash flow
-11.8%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,299,900
3
bds
|
3
ba
|
2,458
sqft
|
built
1958
59 Johnson Rd, Winchester, MA 01890
$-3,284
Cash flow
-13.2%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
24 out of 32 properties for sale in Winchester, MA
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Active
$2,750,000
5
bds
|
4
ba
|
4,779
sqft
|
built
1938
48 Salisbury St, Winchester, MA 01890
$-10,468
Cash flow
-19.9%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,599,000
6
bds
|
5
ba
|
5,876
sqft
|
built
1870
5 Stratford Rd, Winchester, MA 01890
$-14,220
Cash flow
-20.6%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,099,000
6
bds
|
4
ba
|
3,521
sqft
|
built
1897
19 Glengarry Rd, Winchester, MA 01890
$-6,843
Cash flow
-17.0%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,599,000
3
bds
|
3
ba
|
2,541
sqft
|
built
1960
9 Pilgrim Dr, Winchester, MA 01890
$-4,875
Cash flow
-15.9%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,999,000
4
bds
|
4
ba
|
4,731
sqft
|
built
1992
6 Samoset Rd, Winchester, MA 01890
$-5,797
Cash flow
-15.1%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,399,000
7
bds
|
6
ba
|
4,829
sqft
|
built
2025
89 Wildwood St, Winchester, MA 01890
$-7,046
Cash flow
-15.3%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$3,989,000
6
bds
|
8
ba
|
7,330
sqft
|
built
2019
6 Ledgewood Rd, Winchester, MA 01890
$-17,609
Cash flow
-23.0%
Cash-on-Cash Return
0.4%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,299,900
6
bds
|
4
ba
|
4,385
sqft
|
built
1910
5 Bacon St, Winchester, MA 01890
$-8,626
Cash flow
-19.6%
Cash-on-Cash Return
1.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,999,000
6
bds
|
5
ba
|
6,367
sqft
|
built
2025
40 Foxcroft Rd, Winchester, MA 01890
$-16,595
Cash flow
-21.7%
Cash-on-Cash Return
0.7%
Cap rate
0.1%
Rent to Value Ratio
Active
$1,075,000
4
bds
|
3
ba
|
1,860
sqft
|
built
1914
60 Harvard St, Winchester, MA 01890
$-3,563
Cash flow
-17.3%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,350,000
5
bds
|
4
ba
|
5,006
sqft
|
built
1992
276 High St, Winchester, MA 01890
$-7,536
Cash flow
-16.7%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,199,000
6
bds
|
7
ba
|
8,463
sqft
|
built
2006
26 Swan Rd, Winchester, MA 01890
$-13,287
Cash flow
-21.7%
Cash-on-Cash Return
0.7%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,879,000
5
bds
|
4
ba
|
3,294
sqft
|
built
1910
20 Grove Pl, Winchester, MA 01890
$-5,041
Cash flow
-14.0%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,239,000
5
bds
|
5
ba
|
4,798
sqft
|
built
2017
61 Grove St, Winchester, MA 01890
$-6,749
Cash flow
-15.7%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,900,000
4
bds
|
5
ba
|
5,361
sqft
|
built
1984
4 Aricia Ln, Winchester, MA 01890
$-5,706
Cash flow
-15.7%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,990,000
4
bds
|
5
ba
|
4,474
sqft
|
built
1959
4 Chestnut St, Winchester, MA 01890
$-6,617
Cash flow
-17.3%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,195,000
6
bds
|
6
ba
|
5,791
sqft
|
built
1924
58 Bacon St, Winchester, MA 01890
$-5,998
Cash flow
-14.3%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,349,900
5
bds
|
2
ba
|
1,706
sqft
|
built
1880
35 Harvard St, Winchester, MA 01890
$-3,982
Cash flow
-15.4%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,550,000
5
bds
|
5
ba
|
3,800
sqft
|
built
1954
19 Laurel Hill Ln, Winchester, MA 01890
$-10,004
Cash flow
-20.5%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,249,000
6
bds
|
7
ba
|
6,028
sqft
|
built
2025
44 Cabot St, Winchester, MA 01890
$-12,402
Cash flow
-19.9%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,799,900
7
bds
|
8
ba
|
7,429
sqft
|
built
2025
11 Viking Rd, Winchester, MA 01890
$-13,954
Cash flow
-19.2%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,699,000
7
bds
|
8
ba
|
7,982
sqft
|
built
2024
54 Johnson Rd, Winchester, MA 01890
$-10,605
Cash flow
-15.0%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio