Skyline Dr, Wellesley, MA Property Records

Norfolk County and Wellesley Town property records for 18 addresses on Skyline Dr, Wellesley, MA · Last verified August 2026

Skyline Dr Highlights

Properties 18
Median Sale Price $1,390,000
Deeds and Mortgages on File 23
Median Price per Sqft $505
Owner Occupied 78%
Median Annual Tax Bill $18,936
Median Year Built 1958
Median Ownership Tenure 9 years

Properties on Skyline Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

4 Skyline Dr

4 bd · 2.5 ba · 1,930 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,052,700Aug 2021 $13,2412025 —Jun 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

8 Skyline Dr

4 bd · 2.5 ba · 2,359 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,425,000Dec 2021 $15,6052025 Amount on Record Jul 2009 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

11 Skyline Dr

5 bd · 6.5 ba · 4,877 sqft · 0.641 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$950,000May 2018 $27,4172025 —Feb 2017 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

17 Skyline Dr

3 bd · 3 ba · 2,454 sqft · 0.511 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$820,000Aug 1999 $17,5692025 Amount on Record Nov 1996 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

18 Skyline Dr

4 bd · 2.5 ba · 2,695 sqft · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$890,000Jun 2002 $15,4412025 Amount on Record Jul 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

21 Skyline Dr

3 bd · 3.5 ba · 3,131 sqft · 0.495 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$615,000Jun 1997 $17,2502025 Amount on Record Nov 1993 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

22 Skyline Dr

5 bd · 5.5 ba · 4,149 sqft · 0.55 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,427,500Jun 2019 $29,1232025 Amount on Record Oct 2017 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

26 Skyline Dr

4 bd · 4.5 ba · 3,101 sqft · 0.813 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,390,000Sep 2020 $19,1412025 Amount on Record Jan 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

27 Skyline Dr

6 bd · 4.5 ba · 3,688 sqft · 0.548 acres

Last Sale Tax Bill Prior Sale Owner Records
$415,500Aug 1990 $19,8512025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

31 Skyline Dr

4 bd · 2.5 ba · 2,476 sqft · 0.603 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jul 1986 $17,1882025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

32 Skyline Dr

3 bd · 2 ba · 1,620 sqft · 0.863 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2017 $16,1292025 —Jun 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

35 Skyline Dr

4 bd · 2.5 ba · 2,628 sqft · 0.65 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$990,000Jun 2013 $18,7102025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

36 Skyline Dr

4 bd · 2.5 ba · 3,112 sqft · 0.805 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,572,500Dec 2020 $21,0532025 Amount on Record Jun 2012 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

39 Skyline Dr

5 bd · 6.5 ba · 5,228 sqft · 0.757 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,194,375Oct 2020 $41,8192025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

40 Skyline Dr

2 bd · 3 ba · 2,718 sqft · 0.696 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Nov 1989 $18,2062025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

43 Skyline Dr

4 bd · 2.5 ba · 3,192 sqft · 0.922 acres

Last Sale Tax Bill Prior Sale Owner Records
$21,1252025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

44 Skyline Dr

3 bd · 3.5 ba · 3,322 sqft · 0.766 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2004 $22,6162025 Amount on Record Jul 2002 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

47 Skyline Dr

4 bd · 4.5 ba · 2,216 sqft · 0.727 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$18,9362025 2 Names on Record AssessorUpdated Jul 2026

Property Records in Nearby Streets