Residential Property Data Records on Penn Rd, Winchester, MA

We found 8 addresses on Penn Rd, Winchester, MA.

2 Penn RdWinchester, MA 01890

Estimated Value $1,686,000
Living Area 2,016 SqFt

Beds 4
Baths 2.5
Year Built 1927

Property Type Single Family
Ownership Type Mixed

APN WINC M:021 B:0206 L:0
Municipality WINCHESTER

School District Winchester School District

3 Penn RdWinchester, MA 01890

Estimated Value $1,663,000
Living Area 4,993 SqFt

Beds 4
Baths 3.5
Year Built 1929

Property Type Single Family
Ownership Type Individual

APN WINC M:021 B:0213 L:0
Subdivision Fairmount Park

School District Winchester School District

4 Penn RdWinchester, MA 01890

Estimated Value $1,889,000
Living Area 3,113 SqFt

Beds 5
Baths 3
Year Built 1930

Property Type Single Family
Ownership Type Multiple

APN WINC M:021 B:0207 L:0
Subdivision Fairmont Park

School District Winchester School District

5 Penn RdWinchester, MA 01890

Estimated Value $2,272,000
Living Area 3,796 SqFt

Beds 3
Baths 2.5
Year Built 1933

Property Type Single Family
Ownership Type Multiple

APN WINC M:021 B:0212 L:0
Subdivision Fairmount Park

School District Winchester School District

6 Penn RdWinchester, MA 01890

Estimated Value $1,520,000
Living Area 2,359 SqFt

Beds 4
Baths 3
Year Built 1920

Property Type Single Family
Ownership Type Multiple

APN WINC M:021 B:0208 L:0
Subdivision Fairmount Park

School District Winchester School District

7 Penn RdWinchester, MA 01890

Estimated Value $1,647,000
Living Area 3,069 SqFt

Beds 4
Baths 1.5
Year Built 1927

Property Type Single Family
Ownership Type Related

APN WINC M:021 B:0211 L:0
Municipality WINCHESTER

School District Winchester School District

8 Penn RdWinchester, MA 01890

Estimated Value $1,241,000
Living Area 2,295 SqFt

Beds 4
Baths 3
Year Built 1927

Property Type Single Family
Ownership Type Related

APN WINC M:021 B:0209 L:0
Municipality WINCHESTER

School District Winchester School District

9 Penn RdWinchester, MA 01890

Estimated Value $2,632,000
Living Area 4,800 SqFt

Beds 5
Baths 4.5
Year Built 2011

Property Type Single Family
Ownership Type Multiple

APN WINC M:021 B:0210 L:0
Subdivision Fairmont Park

School District Winchester School District

Investment Properties near on Penn Rd, Winchester, MA

7 Washington StWinchester, MA 01890

Estimated Value $2,719,000
Living Area 4,705 SqFt

Beds 4
Baths 4.5
Year Built 1890

Property Type Single Family
Ownership Type Multiple

APN WINC M:005 B:0256 L:0
Subdivision Winchester

School District Winchester School District

18 Mystic Valley PkwyWinchester, MA 01890

Estimated Value $1,508,000
Living Area 2,559 SqFt

Beds 4
Baths 3.5
Year Built 1920

Property Type Single Family
Ownership Type Related

APN WINC M:017 B:0003 L:0
Municipality WINCHESTER

School District Winchester School District

214 Crosby StArlington, MA 02474

Estimated Value $1,842,000
Living Area 3,447 SqFt

Beds 3
Baths 3.5
Year Built 1932

Property Type Single Family
Ownership Type Related

APN ARLI M:097.0 B:0003 L:0003
Municipality ARLINGTON

School District Arlington School District

366 Main StWinchester, MA 01890

Estimated Value $3,392,000
Living Area 5,541 SqFt

Beds 5
Baths 5.5
Year Built 1875

Property Type Single Family
Ownership Type Multiple

APN WINC M:008 B:0082 L:0
Municipality WINCHESTER

School District Winchester School District

10 Josephine RdMedford, MA 02155

Estimated Value $854,000
Living Area 2,392 SqFt

Beds 3
Baths 1.5
Year Built 1953

Property Type Single Family
Ownership Type Related

APN MEDF M:E-01 B:0037
Neighborhood West Medford

School District Medford School District

4 Valleywood CirWinchester, MA 01890

Estimated Value $1,297,000
Living Area 1,936 SqFt

Beds 3
Baths 3
Year Built 1966

Property Type Single Family
Ownership Type Multiple

APN WINC M:027 B:0048 L:0
Municipality WINCHESTER

School District Winchester School District

3 Mccall RdWinchester, MA 01890

Estimated Value $4,717,000
Living Area 6,671 SqFt

Beds 4
Baths 3
Year Built 1932

Property Type Single Family
Ownership Type Related

APN WINC M:020 B:0072 L:0
Municipality WINCHESTER

School District Winchester School District

316 Main StWinchester, MA 01890

Estimated Value $1,373,000
Living Area 2,384 SqFt

Beds 3
Baths 2.5
Year Built 1941

Property Type Single Family
Ownership Type Related

APN WINC M:008 B:0049 L:0
Municipality WINCHESTER

School District Winchester School District

25 Chesterford RdWinchester, MA 01890

Estimated Value $1,306,000
Living Area 2,279 SqFt

Beds 4
Baths 2
Year Built 1940

Property Type Single Family
Ownership Type Multiple

APN WINC M:019 B:0145 L:0
Municipality WINCHESTER

School District Winchester School District

225 High StWinchester, MA 01890

Estimated Value $3,795,000
Living Area 7,325 SqFt

Beds 4
Baths 4.5
Year Built 2006

Property Type Single Family
Ownership Type Corporate

APN WINC M:027 B:0338 L:0
Subdivision Winchester

School District Winchester School District

62 Windmill LnArlington, MA 02474

Estimated Value $1,388,000
Living Area 2,604 SqFt

Beds 2
Baths 2.5
Year Built 1954

Property Type Single Family
Ownership Type Multiple

APN ARLI M:103.0 B:0001 L:0015
Municipality ARLINGTON

School District Arlington School District

163 Cambridge StWinchester, MA 01890

Estimated Value $998,000
Living Area 1,410 SqFt

Beds 4
Baths 1.5
Year Built 1938

Property Type Single Family
Ownership Type Individual

APN WINC M:018 B:0298 L:0
Municipality WINCHESTER

School District Winchester School District

1 Red Coach LnWinchester, MA 01890

Estimated Value $1,908,000
Living Area 4,325 SqFt

Beds 4
Baths 3
Year Built 1982

Property Type Single Family
Ownership Type Individual

APN WINC M:026 B:0277 L:0
Municipality WINCHESTER

School District Winchester School District

30 Mystic Valley PkwyWinchester, MA 01890

Estimated Value $2,017,000
Living Area 3,065 SqFt

Beds 4
Baths 2
Year Built 1918

Property Type Single Family
Ownership Type Related

APN WINC M:017 B:0031 L:0
Municipality WINCHESTER

School District Winchester School District

3 Myopia RdWinchester, MA 01890

Estimated Value $4,456,000
Living Area 8,482 SqFt

Beds 6
Baths 6.5
Year Built 1983

Property Type Single Family
Ownership Type Mixed

APN WINC M:020 B:0215 L:0
Municipality WINCHESTER

School District Winchester School District

22 Ginn RdWinchester, MA 01890

Estimated Value $1,959,000
Living Area 3,383 SqFt

Beds 4
Baths 2.5
Year Built 1905

Property Type Single Family
Ownership Type Related

APN WINC M:016 B:0030 L:0
Municipality WINCHESTER

School District Winchester School District

Streets Near Penn Rd, Winchester, MA

Street

Properties

Avg. Beds

Avg. Baths

Avg. Property Value

Avg. Property Size

Last Sale Date

Cambridge St11643$1,643,2965,012 Sq.Ft.5/8/2025Church St9943$1,852,3724,328 Sq.Ft.6/24/2024Grove St6043$1,964,2003,398 Sq.Ft.6/5/2025High St8743$2,179,4274,001 Sq.Ft.1/9/2025Johnson Rd6543$1,636,8604,275 Sq.Ft.3/28/2025Pond St7432$1,385,2622,309 Sq.Ft.2/3/2025Ridge St8643$1,770,3473,194 Sq.Ft.6/16/2025Wainwright Rd12833$1,671,2882,985 Sq.Ft.5/27/2025Wedgemere Ave5054$2,881,5404,714 Sq.Ft.4/25/2025Wildwood St7743$1,962,6763,276 Sq.Ft.3/7/2025

Additional Questions?

Looking for off-market properties in Winchester, MA?

Traditional methods include networking with contractors, scouting neighborhoods ("driving for dollars"), or purchasing leads from wholesalers can be tedious. PropertyReach streamlines this process with predictive analytics and neighborhood benchmarks, using Winchester, MA property records and MLS failed listings to refine your search. Effortlessly compare properties, access owner contact details, and secure the best off-market deals at the right price.

What is the median home value in Winchester, MA?

The median home value in Winchester, MA is $1,559,500, with an average home value of $1,662,023. The average price per square foot for homes in the area is $316.45.

How Can I Find Pre-foreclosures or Distressed Properties in Winchester, MA?

Foreclosures and distressed properties in Winchester, MA can be found through public records, foreclosure notices, and auction announcements from the county clerk or sheriff’s office. PropertyReach streamlines this by aggregating public and MLS data, making it easier to identify distressed properties and connect with owners directly.

Residential Property Data Records on Penn Rd, Winchester, MA

We found 8 addresses on Penn Rd, Winchester, MA.

2 Penn RdWinchester, MA 01890

Estimated Value $1,686,000

Living Area 2,016 SqFt

Beds 4

Baths 2.5

Year Built 1927

Property Type Single Family

Ownership Type Mixed

APN WINC M:021 B:0206 L:0

Municipality WINCHESTER

School District Winchester School District

3 Penn RdWinchester, MA 01890

Estimated Value $1,663,000

Living Area 4,993 SqFt

Beds 4

Baths 3.5

Year Built 1929

Property Type Single Family

Ownership Type Individual

APN WINC M:021 B:0213 L:0

Subdivision Fairmount Park

School District Winchester School District

4 Penn RdWinchester, MA 01890

Estimated Value $1,889,000

Living Area 3,113 SqFt

Beds 5

Baths 3

Year Built 1930

Property Type Single Family

Ownership Type Multiple

APN WINC M:021 B:0207 L:0

Subdivision Fairmont Park

School District Winchester School District

5 Penn RdWinchester, MA 01890

Estimated Value $2,272,000

Living Area 3,796 SqFt

Beds 3

Baths 2.5

Year Built 1933

Property Type Single Family

Ownership Type Multiple

APN WINC M:021 B:0212 L:0

Subdivision Fairmount Park

School District Winchester School District

6 Penn RdWinchester, MA 01890

Estimated Value $1,520,000

Living Area 2,359 SqFt

Beds 4

Baths 3

Year Built 1920

Property Type Single Family

Ownership Type Multiple

APN WINC M:021 B:0208 L:0

Subdivision Fairmount Park

School District Winchester School District

7 Penn RdWinchester, MA 01890

Estimated Value $1,647,000

Living Area 3,069 SqFt

Beds 4

Baths 1.5

Year Built 1927

Property Type Single Family

Ownership Type Related

APN WINC M:021 B:0211 L:0

Municipality WINCHESTER

School District Winchester School District

8 Penn RdWinchester, MA 01890

Estimated Value $1,241,000

Living Area 2,295 SqFt

Beds 4

Baths 3

Year Built 1927

Property Type Single Family

Ownership Type Related

APN WINC M:021 B:0209 L:0

Municipality WINCHESTER

School District Winchester School District

9 Penn RdWinchester, MA 01890