As the gateway to the Sebago Lakes Region, Windham is a magnet for seasonal visitors. The town benefits from being just 30 minutes from Portland. This gives residents easy access to employment hubs while also letting them enjoy a quieter suburban lifestyle. Residents find employment at various businesses including Maine Medical Center, Idexx Laboratories, and Hannaford Supermarkets.
Neighborhoods in Windham offer different investment strategies. North Windham is the town's commercial and residential heart and has a mix of affordable homes and rental properties. The areas near Sebago Lake and Highland Lake offer gorgeous waterfront properties and vacation rentals, creating high seasonal demand and excellent long-term appreciation potential. And for people who gravitate toward rural charm, South Windham has larger lots and a peaceful atmosphere.
The town's appeal extends to Sebago Lake State Park, while the nearby Presumpscot River provides a variety of outdoor activities. The Windham Rail Trail connects residents to the area's natural beauty. Windham's vibrant community hosts seasonal farmers' markets, local festivals, and family-oriented events. The town's consistent growth and lifestyle appeal make it an optimistic market for both rental income and property appreciation.
Popular Streets in Windham, Maine
Falmouth Rd19032$450,1691,462 Sq.Ft.5/28/2025Gray Rd20632$476,0631,896 Sq.Ft.4/15/2025Highland Cliff Rd12932$561,4141,783 Sq.Ft.9/17/2024Main St10432$468,3452,007 Sq.Ft.4/17/2025Pope Rd18432$505,8401,645 Sq.Ft.1/3/2025River Rd31632$470,0721,711 Sq.Ft.5/7/2025Roosevelt Trl48032$469,2003,481 Sq.Ft.5/29/2025Tandberg Trl13132$442,8892,012 Sq.Ft.5/9/2025Varney Mill Rd13132$457,9671,486 Sq.Ft.4/30/2025Windham Center Rd12932$524,6892,032 Sq.Ft.5/12/2025All Streets in Windham, Maine
Winchester Dr633$773,1672,544 Sq.Ft.2/28/2020Windham Center Rd12932$524,6892,032 Sq.Ft.5/12/2025Winslow Dr632$505,8331,564 Sq.Ft.5/21/2019Wintergreen Cir932$1,152,7501,584 Sq.Ft.10/29/2013Woldbrook Dr2543$922,1202,945 Sq.Ft.1/23/2025Wolf Creek Dr432$554,7501,720 Sq.Ft.10/29/2021Woodland Rd3132$443,1381,391 Sq.Ft.5/23/2025Wright Rd531$371,4001,118 Sq.Ft.3/12/2021Wymans Way422$406,0001,812 Sq.Ft.8/3/2015Yankee Dr332$653,0002,135 Sq.Ft.8/13/2024Yellowbird Ln342$600,0002,556 Sq.Ft.5/25/2022Youngs Farm Rd431$448,5001,413 Sq.Ft.9/10/2021Zippers Way231$367,5001,008 Sq.Ft.7/18/2017Zulu Rd133$646,0002,112 Sq.Ft.N/AZylar Dr111$3,069,000861 Sq.Ft.N/A25 Arrowhead PassWindham, ME 04062
Estimated Value $507,000
Living Area 1,120 SqFt
Beds 4
Baths 2
Year Built 2020
Property Type Single Family
Ownership Type Individual
APN WINM M:4 B:23 L:B03
Municipality WINDHAM
School District Regional School Unit 14
21 Revolution DrWindham, ME 04062
Estimated Value $748,000
Living Area 2,953 SqFt
Beds 3
Baths 2.5
Year Built 2021
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:63 L:13 U:19
Municipality WINDHAM
School District Regional School Unit 14
220 Hardy RdWestbrook, ME 04092
Estimated Value $353,000
Living Area 1,004 SqFt
Beds 2
Baths 1
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN WSBR M:020 L:007
Municipality WESTBROOK
School District Westbrook
30 Lowell Farm RdFalmouth, ME 04105
Estimated Value $675,000
Living Area 2,010 SqFt
Beds 3
Baths 2
Year Built 1988
Property Type Single Family
Ownership Type Related
APN FMTH M:HL7 B:001
Municipality FALMOUTH
78 Mast RdWestbrook, ME 04092
Estimated Value $361,000
Living Area 816 SqFt
Beds 3
Baths 1
Year Built 1963
Property Type Single Family
Ownership Type Individual
APN WSBR M:023 L:032
Municipality WESTBROOK
School District Westbrook
40 Settlers WayGorham, ME 04038
Estimated Value $808,000
Living Area 2,950 SqFt
Beds 3
Baths 3.5
Year Built 1987
Property Type Single Family
Ownership Type Multiple
APN GRHM M:43A B:017 L:038
Subdivision Fort Hill Farms
65 Chute RdWindham, ME 04062
Estimated Value $667,000
Living Area 1,692 SqFt
Beds 2
Baths 2
Year Built 1971
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:23 L:C
Municipality WINDHAM
18 Rosewood DrWestbrook, ME 04092
Estimated Value $542,000
Living Area 1,428 SqFt
Beds 2
Baths 2.5
Year Built 1998
Property Type Single Family
Ownership Type Related
APN WSBR M:023 L:203
Municipality WESTBROOK
School District Westbrook
26 Stillwater Dr #6Westbrook, ME 04092
Estimated Value $627,000
Living Area 1,930 SqFt
Beds 4
Baths 2.5
Year Built 2014
Property Type Condominium
Ownership Type Related
APN WSBR M:010 B:006 L:005
Municipality WESTBROOK
School District Westbrook
60 Sleepy Hollow DrGorham, ME 04038
Estimated Value $705,000
Living Area 1,933 SqFt
Beds 3
Baths 2
Year Built 2002
Property Type Single Family
Ownership Type Related
APN GRHM M:051 B:008 L:012
Municipality GORHAM
43 Pennywhistle DrWindham, ME 04062
Estimated Value $974,000
Living Area 3,024 SqFt
Beds 4
Baths 2.5
Year Built 2024
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:25 L:10
Municipality WINDHAM
School District Regional School Unit 14
81 Queen StGorham, ME 04038
Estimated Value $687,000
Living Area 550 SqFt
Beds 2
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Related
APN GRHM M:048 B:015 L:000
Municipality GORHAM
38 Old Dynamite WayGorham, ME 04038
Estimated Value $776,000
Living Area 1,884 SqFt
Beds 3
Baths 2.5
Year Built 2014
Property Type Single Family
Ownership Type Multiple
APN GRHM M:030 B:018 L:034
Subdivision Tannery Brook Sub
41 Wilson DrWestbrook, ME 04092
Estimated Value $553,000
Living Area 1,592 SqFt
Beds 3
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN WSBR M:043 L:214
Subdivision Wilson Drive Sub
School District Westbrook
36 Revolution DrWindham, ME 04062
Estimated Value $774,000
Living Area 2,180 SqFt
Beds 3
Baths 2
Year Built 2020
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:63 L:13 U:12
Municipality WINDHAM
School District Regional School Unit 14
844 Duck Pond RdWestbrook, ME 04092
Estimated Value $561,000
Living Area 2,076 SqFt
Beds 4
Baths 2
Year Built 1869
Property Type Duplex 2 Units
Ownership Type Multiple
APN WSBR M:023 L:057
Municipality WESTBROOK
School District Westbrook