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
$749,900
3
bds
|
2
ba
|
1,931
sqft
|
built
1956
235 Cross St, Winchester, MA 01890
$-1,464
Cash flow
-10.2%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
$699,900
2
bds
|
2
ba
|
1,168
sqft
|
built
2000
7 Conant Rd, Winchester, MA 01890
$-2,282
Cash flow
-17.0%
Cash-on-Cash Return
1.8%
Cap rate
0.5%
Rent to Value Ratio
32 out of 37 properties for sale in Winchester, MA
Limited Results Shown
Create a free account, or log in to reveal all property listings and enjoy the complete experience.
$2,250,000
5
bds
|
4
ba
|
3,719
sqft
|
built
1952
17 Harrison St, Winchester, MA 01890
$-7,626
Cash flow
-17.7%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
$749,900
3
bds
|
2
ba
|
1,931
sqft
|
built
1956
235 Cross St, Winchester, MA 01890
$-1,464
Cash flow
-10.2%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
$2,599,000
4
bds
|
5
ba
|
5,501
sqft
|
built
2024
15 Churchill Rd, Winchester, MA 01890
$-5,192
Cash flow
-10.4%
Cash-on-Cash Return
3.3%
Cap rate
0.4%
Rent to Value Ratio
$1,199,000
3
bds
|
2
ba
|
1,906
sqft
|
built
1926
44 Forest St, Winchester, MA 01890
$-3,220
Cash flow
-14.0%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
$1,499,000
3
bds
|
2
ba
|
2,351
sqft
|
built
1956
19 Cox Rd, Winchester, MA 01890
$-5,309
Cash flow
-18.5%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
$2,499,000
6
bds
|
4
ba
|
4,212
sqft
|
built
1880
19 Yale St, Winchester, MA 01890
$-8,916
Cash flow
-18.6%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
$2,950,000
6
bds
|
7
ba
|
6,968
sqft
|
built
2002
14 Nassau Dr, Winchester, MA 01890
$-9,138
Cash flow
-16.2%
Cash-on-Cash Return
2.0%
Cap rate
0.3%
Rent to Value Ratio
$2,899,000
5
bds
|
6
ba
|
4,627
sqft
|
built
2025
11 Taft Dr, Winchester, MA 01890
$-11,673
Cash flow
-21.0%
Cash-on-Cash Return
0.8%
Cap rate
0.2%
Rent to Value Ratio
$2,450,000
5
bds
|
5
ba
|
3,940
sqft
|
built
1983
17 Wagon Wheel Rd, Winchester, MA 01890
$-8,365
Cash flow
-17.8%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
$2,199,000
6
bds
|
4
ba
|
4,696
sqft
|
built
2016
5 Squire Rd, Winchester, MA 01890
$-7,119
Cash flow
-16.9%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
$998,000
4
bds
|
3
ba
|
2,333
sqft
|
built
1959
48 Tremont St, Winchester, MA 01890
$-2,362
Cash flow
-12.3%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
$1,199,000
3
bds
|
2
ba
|
1,520
sqft
|
built
1929
10 Allen Rd, Winchester, MA 01890
$-3,810
Cash flow
-16.6%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
$3,599,000
6
bds
|
6
ba
|
7,431
sqft
|
built
1905
27 Everett Ave, Winchester, MA 01890
$-12,062
Cash flow
-17.5%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
$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
$2,449,000
4
bds
|
4
ba
|
4,959
sqft
|
built
1980
5 Azalea Rd, Winchester, MA 01890
$-7,822
Cash flow
-16.7%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
$1,295,000
4
bds
|
2
ba
|
2,202
sqft
|
built
1927
71 Woodside Rd, Winchester, MA 01890
$-3,705
Cash flow
-14.9%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
$2,499,000
6
bds
|
4
ba
|
4,667
sqft
|
built
1895
9 Prospect St, Winchester, MA 01890
$-8,668
Cash flow
-18.1%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
$1,199,000
4
bds
|
2
ba
|
2,621
sqft
|
built
1952
61 Westland Ave, Winchester, MA 01890
$-3,515
Cash flow
-15.3%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
$1,499,000
3
bds
|
4
ba
|
3,351
sqft
|
built
1946
34 Fells Rd, Winchester, MA 01890
$-4,502
Cash flow
-15.7%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
$2,599,000
7
bds
|
6
ba
|
4,829
sqft
|
built
2025
89 Wildwood St, Winchester, MA 01890
$-7,992
Cash flow
-16.0%
Cash-on-Cash Return
2.0%
Cap rate
0.3%
Rent to Value Ratio
$2,850,000
4
bds
|
3
ba
|
4,276
sqft
|
built
1985
8 Tanglewood Ln, Winchester, MA 01890
$-10,323
Cash flow
-18.9%
Cash-on-Cash Return
1.3%
Cap rate
0.3%
Rent to Value Ratio
$3,350,000
6
bds
|
5
ba
|
5,198
sqft
|
built
1910
21 Sheffield W, Winchester, MA 01890
$-11,613
Cash flow
-18.1%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
$1,595,000
3
bds
|
4
ba
|
3,763
sqft
|
built
1988
7 Wainwright Rd, Winchester, MA 01890
$-5,126
Cash flow
-16.8%
Cash-on-Cash Return
1.8%
Cap rate
0.4%
Rent to Value Ratio
$3,149,000
7
bds
|
6
ba
|
6,200
sqft
|
built
1916
10 Sheffield Rd, Winchester, MA 01890
$-10,951
Cash flow
-18.1%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
$2,399,000
5
bds
|
4
ba
|
5,077
sqft
|
built
1992
276 High St, Winchester, MA 01890
$-7,768
Cash flow
-16.9%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
$3,698,000
6
bds
|
7
ba
|
8,866
sqft
|
built
2024
20 Amberwood Dr, Winchester, MA 01890
$-12,725
Cash flow
-18.0%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
$2,695,000
4
bds
|
5
ba
|
5,233
sqft
|
built
2004
18 Middlesex St, Winchester, MA 01890
$-7,147
Cash flow
-13.8%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
$3,989,000
6
bds
|
7
ba
|
8,463
sqft
|
built
2006
26 Swan Rd, Winchester, MA 01890
$-17,025
Cash flow
-22.3%
Cash-on-Cash Return
0.6%
Cap rate
0.2%
Rent to Value Ratio
$2,999,000
5
bds
|
6
ba
|
5,354
sqft
|
built
1850
8 Chestnut St, Winchester, MA 01890
$-8,683
Cash flow
-15.1%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
$699,900
2
bds
|
2
ba
|
1,168
sqft
|
built
2000
7 Conant Rd, Winchester, MA 01890
$-2,282
Cash flow
-17.0%
Cash-on-Cash Return
1.8%
Cap rate
0.5%
Rent to Value Ratio
$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
$1,599,000
6
bds
|
3
ba
|
3,543
sqft
|
built
1850
189 Mystic Valley Pkwy, Winchester, MA 01890
$-3,965
Cash flow
-12.9%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio