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
$679,900
2
bds
|
2
ba
|
1,168
sqft
|
built
2000
7 Conant Rd, Winchester, MA 01890
$-2,520
Cash flow
-19.3%
Cash-on-Cash Return
1.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$959,000
3
bds
|
1
ba
|
1,425
sqft
|
built
1920
571 Washington St, Winchester, MA 01890
$-2,830
Cash flow
-15.4%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
36 out of 46 properties for sale in Winchester, MA
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Active
$1,999,000
5
bds
|
4
ba
|
3,874
sqft
|
built
1932
4 Worthen Rd, Winchester, MA 01890
$-7,420
Cash flow
-19.4%
Cash-on-Cash Return
1.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,250,000
5
bds
|
5
ba
|
5,000
sqft
|
built
1968
1 Fox Hunt Ln, Winchester, MA 01890
$-7,955
Cash flow
-18.4%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,599,000
6
bds
|
5
ba
|
5,824
sqft
|
built
1911
107 Cambridge St, Winchester, MA 01890
$-8,670
Cash flow
-17.4%
Cash-on-Cash Return
2.3%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,349,900
5
bds
|
2
ba
|
1,706
sqft
|
built
1880
35 Harvard St, Winchester, MA 01890
$-4,641
Cash flow
-17.9%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$3,599,000
6
bds
|
5
ba
|
5,876
sqft
|
built
1870
5 Stratford Rd, Winchester, MA 01890
$-15,977
Cash flow
-23.2%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,349,000
3
bds
|
2
ba
|
3,335
sqft
|
built
1953
10 Girard Rd, Winchester, MA 01890
$-4,052
Cash flow
-15.7%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$2,299,000
6
bds
|
4
ba
|
4,667
sqft
|
built
1895
9 Prospect St, Winchester, MA 01890
$-8,844
Cash flow
-20.1%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,550,000
5
bds
|
5
ba
|
3,800
sqft
|
built
1954
19 Laurel Hill Ln, Winchester, MA 01890
$-11,250
Cash flow
-23.0%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,799,999
3
bds
|
3
ba
|
3,002
sqft
|
built
1983
44 Amberwood Dr, Winchester, MA 01890
$-6,483
Cash flow
-18.8%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$3,175,000
5
bds
|
5
ba
|
5,386
sqft
|
built
1963
21 Fernway, Winchester, MA 01890
$-13,542
Cash flow
-22.3%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,199,900
4
bds
|
3
ba
|
2,302
sqft
|
built
1915
518 Washington St, Winchester, MA 01890
$-3,712
Cash flow
-16.1%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,899,000
7
bds
|
6
ba
|
5,864
sqft
|
built
1916
10 Sheffield Rd, Winchester, MA 01890
$-11,184
Cash flow
-20.1%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,249,000
6
bds
|
7
ba
|
6,028
sqft
|
built
2025
44 Cabot St, Winchester, MA 01890
$-13,989
Cash flow
-22.5%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
Rent to Value Ratio
Active
$859,000
2
bds
|
1
ba
|
1,123
sqft
|
built
1986
22 Grove Pl, Winchester, MA 01890
$-3,276
Cash flow
-19.9%
Cash-on-Cash Return
1.7%
Cap rate
0.4%
Rent to Value Ratio
Active
$959,000
3
bds
|
1
ba
|
1,425
sqft
|
built
1920
571 Washington St, Winchester, MA 01890
$-2,830
Cash flow
-15.4%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,999,000
6
bds
|
5
ba
|
6,367
sqft
|
built
2025
40 Foxcroft Rd, Winchester, MA 01890
$-18,549
Cash flow
-24.2%
Cash-on-Cash Return
0.7%
Cap rate
0.1%
Rent to Value Ratio
Active
$3,475,000
5
bds
|
4
ba
|
5,632
sqft
|
built
1973
80 Arlington St, Winchester, MA 01890
$-15,875
Cash flow
-23.8%
Cash-on-Cash Return
0.8%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,099,000
6
bds
|
4
ba
|
5,238
sqft
|
built
1915
54 Wedgemere Ave, Winchester, MA 01890
$-11,619
Cash flow
-19.6%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,329,000
3
bds
|
2
ba
|
1,884
sqft
|
built
1919
147 Highland Ave, Winchester, MA 01890
$-4,733
Cash flow
-18.6%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,899,000
5
bds
|
5
ba
|
6,904
sqft
|
built
1989
11 Fieldstone Dr, Winchester, MA 01890
$-10,241
Cash flow
-18.4%
Cash-on-Cash Return
2.0%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,599,000
4
bds
|
5
ba
|
5,501
sqft
|
built
2025
15 Churchill Rd, Winchester, MA 01890
$-6,462
Cash flow
-13.0%
Cash-on-Cash Return
3.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,449,900
5
bds
|
2
ba
|
3,033
sqft
|
built
1957
7 Thornberry Rd, Winchester, MA 01890
$-4,140
Cash flow
-14.9%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,499,000
3
bds
|
3
ba
|
2,605
sqft
|
built
1870
14 Hillside Ave, Winchester, MA 01890
$-5,280
Cash flow
-18.4%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,850,000
6
bds
|
7
ba
|
6,968
sqft
|
built
2002
14 Nassau Dr, Winchester, MA 01890
$-10,057
Cash flow
-18.4%
Cash-on-Cash Return
2.0%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,899,000
5
bds
|
6
ba
|
4,627
sqft
|
built
2025
11 Taft Dr, Winchester, MA 01890
$-13,089
Cash flow
-23.6%
Cash-on-Cash Return
0.8%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,000,000
6
bds
|
4
ba
|
4,696
sqft
|
built
2016
5 Squire Rd, Winchester, MA 01890
$-7,154
Cash flow
-18.7%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$3,799,900
7
bds
|
8
ba
|
7,429
sqft
|
built
2025
11 Viking Rd, Winchester, MA 01890
$-15,810
Cash flow
-21.7%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,349,000
4
bds
|
4
ba
|
4,959
sqft
|
built
1980
5 Azalea Rd, Winchester, MA 01890
$-8,497
Cash flow
-18.9%
Cash-on-Cash Return
1.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,295,000
4
bds
|
2
ba
|
2,202
sqft
|
built
1927
71 Woodside Rd, Winchester, MA 01890
$-4,338
Cash flow
-17.5%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,499,000
7
bds
|
6
ba
|
4,829
sqft
|
built
2025
89 Wildwood St, Winchester, MA 01890
$-8,740
Cash flow
-18.2%
Cash-on-Cash Return
2.1%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,650,000
4
bds
|
3
ba
|
4,276
sqft
|
built
1985
8 Tanglewood Ln, Winchester, MA 01890
$-10,671
Cash flow
-21.0%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,698,000
6
bds
|
7
ba
|
8,866
sqft
|
built
2024
20 Amberwood Dr, Winchester, MA 01890
$-14,531
Cash flow
-20.5%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,989,000
6
bds
|
7
ba
|
8,463
sqft
|
built
2006
26 Swan Rd, Winchester, MA 01890
$-18,974
Cash flow
-24.8%
Cash-on-Cash Return
0.6%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,890,000
5
bds
|
6
ba
|
5,354
sqft
|
built
1850
8 Chestnut St, Winchester, MA 01890
$-9,579
Cash flow
-17.3%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$679,900
2
bds
|
2
ba
|
1,168
sqft
|
built
2000
7 Conant Rd, Winchester, MA 01890
$-2,520
Cash flow
-19.3%
Cash-on-Cash Return
1.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,699,000
7
bds
|
8
ba
|
7,982
sqft
|
built
2024
54 Johnson Rd, Winchester, MA 01890
$-12,411
Cash flow
-17.5%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio