Pennywhistle Dr, Windham, ME Property Records

Cumberland County and Windham Town property records for 21 addresses on Pennywhistle Dr, Windham, ME · Last verified September 2026

Pennywhistle Dr Highlights

Properties 21
Median Sale Price $760,000
Deeds and Mortgages on File 41
Median Price per Sqft $278
Owner Occupied 71%
Median Annual Tax Bill $9,435
Median Year Built 2022
Median Ownership Tenure 3 years

Properties on Pennywhistle Dr

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

2 Pennywhistle Dr

3 bd · 3.5 ba · 4,005 sqft · built 2024 · 0.771 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,2502025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4 Pennywhistle Dr

3 bd · 2.5 ba · 3,012 sqft · built 2021 · 0.771 acres

Last Sale Tax Bill Prior Sale Owner Records
$685,300Jul 2021 $9,4352025 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

5 Pennywhistle Dr

3 bd · 2.5 ba · 2,992 sqft · built 2024 · 0.694 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,065,000Jan 2025 $12,0432025 Owner on Record AssessorUpdated Aug 2026

6 Pennywhistle Dr

3 bd · 2.5 ba · 3,140 sqft · built 2021 · 0.771 acres

Last Sale Tax Bill Prior Sale Owner Records
$561,900Nov 2020 $9,2602025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

7 Pennywhistle Dr

3 bd · 2.5 ba · 2,802 sqft · built 2021 · 0.692 acres

Last Sale Tax Bill Prior Sale Owner Records
$779,000Sep 2022 $9,2442025 Amount on Record Jan 2022 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

11 Pennywhistle Dr

3 bd · 2.5 ba · 3,590 sqft · built 2022 · 0.798 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,080,000Jun 2023 $13,2952025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

15 Pennywhistle Dr

4 bd · 3.5 ba · 2,581 sqft · built 2021 · 0.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$663,600Oct 2021 $8,7652025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

18 Pennywhistle Dr

3 bd · 2.5 ba · 2,966 sqft · built 2021 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$845,000Nov 2024 $9,6762025 Amount on Record Dec 2021 2 Owners on Record Assessor + 2 DocumentsUpdated Jun 2026

19 Pennywhistle Dr

3 bd · 2.5 ba · 2,196 sqft · built 2022 · 0.744 acres

Last Sale Tax Bill Prior Sale Owner Records
$760,000Nov 2022 $8,1942025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

23 Pennywhistle Dr

3 bd · 2.5 ba · 2,408 sqft · built 2022 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$835,000Aug 2026 $8,5732025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

28 Pennywhistle Dr

3 bd · 2 ba · 2,296 sqft · built 2024 · 0.789 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Oct 2023 $9,6472025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

29 Pennywhistle Dr

1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,7292025 Owner on Record AssessorUpdated Aug 2026

31 Pennywhistle Dr

3 bd · 2.5 ba · 2,818 sqft · built 2021 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$868,000Jul 2024 $9,4212025 Amount on Record Jun 2022 2 Owners on Record Assessor + 2 DocumentsUpdated Jun 2026

32 Pennywhistle Dr

3 bd · 1.5 ba · 2,483 sqft · built 2021 · 0.733 acres

Last Sale Tax Bill Prior Sale Owner Records
$748,000May 2025 $8,6872025 Amount on Record Mar 2022 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

33 Pennywhistle Dr

2 bd · 2 ba · 1,392 sqft · built 2021 · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6962025 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

36 Pennywhistle Dr

4 bd · 4 ba · 3,735 sqft · built 2024 · 0.869 acres

Last Sale Tax Bill Prior Sale Owner Records
$298,178May 2023 $16,7812025 Amount on Record Nov 2022 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

38 Pennywhistle Dr

3 bd · 2.5 ba · 2,908 sqft · built 2022 · 1.14 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,0402025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

39 Pennywhistle Dr

3 bd · 2.5 ba · 3,556 sqft · built 2021 · 0.898 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Dec 2023 $10,8032025 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

40 Pennywhistle Dr

3 bd · 2.5 ba · 2,938 sqft · built 2022 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$625,000Jul 2022 $10,9892025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

41 Pennywhistle Dr

4 bd · 3.5 ba · 2,506 sqft · built 2022 · 0.903 acres

Last Sale Tax Bill Prior Sale Owner Records
$695,700Apr 2021 $8,5002025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

43 Pennywhistle Dr

4 bd · 2.5 ba · 3,024 sqft · built 2024 · 0.951 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Feb 2024 $10,8072025 Amount on Record Jul 2023 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

Property Records in Nearby Streets