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.6/10/2025Highland 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.6/20/2025Windham 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/A21 Mill Ridge RdCumberland Center, ME 04021
Estimated Value $562,000
Living Area 1,666 SqFt
Beds 3
Baths 2.5
Year Built 1978
Property Type Single Family
Ownership Type Multiple
APN CMBL M:U19-A L:12
Municipality CUMBERLAND
School District School Administrative District 51
23 Wilson RdCumberland Center, ME 04021
Estimated Value $874,000
Living Area 3,068 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Related
APN CMBL M:R07-C L:16-A
Municipality CUMBERLAND
School District School Administrative District 51
30 Peaceful WayCumberland Center, ME 04021
Estimated Value $863,000
Living Area 3,212 SqFt
Beds 4
Baths 3.5
Year Built 2022
Property Type Single Family
Ownership Type Related
APN CMBL M:R08 L:68-A U:1
Municipality CUMBERLAND
School District School Administrative District 51
2 Sorrento Way #AGray, ME 04039
Estimated Value $454,000
Living Area 1,302 SqFt
Beds 3
Baths 2.5
Year Built 2015
Property Type Condominium
Ownership Type Individual
APN GRAY M:069 B:041 L:045-002
Municipality GRAY
School District School Administrative District 15
9 Juniper LnGray, ME 04039
Estimated Value $515,000
Living Area 1,920 SqFt
Beds 4
Baths 3
Year Built 2011
Property Type Single Family
Ownership Type Individual
APN GRAY M:064 B:035 L:011-018
Municipality GRAY
School District School Administrative District 15
378 Portland Rd #14Gray, ME 04039
Estimated Value $258,000
Living Area 800 SqFt
Beds 2
Baths 1
Year Built 1987
Property Type Condominium
Ownership Type Corporate
APN GRAY M:075 B:040 L:008-014
Subdivision Tall Pines Condo
School District School Administrative District 15
152 Nash RdWindham, ME 04062
Estimated Value $559,000
Living Area 2,118 SqFt
Beds 3
Baths 1.5
Year Built 2000
Property Type Single Family
Ownership Type Related
APN WINM M:16 B:34 L:5
Subdivision Mary Lowery
School District Regional School Unit 14
23 Island AveCumberland Center, ME 04021
Estimated Value $544,000
Living Area 1,533 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Related
APN CMBL M:U22 L:40
Subdivision Forest Lk
School District School Administrative District 51
15 Moon RdGray, ME 04039
Estimated Value $517,000
Living Area 2,142 SqFt
Beds 3
Baths 2
Year Built 2005
Property Type Single Family
Ownership Type Related
APN GRAY M:075 B:201 L:005-000
Municipality GRAY
School District School Administrative District 15
28 Wilson RdCumberland Center, ME 04021
Estimated Value $484,000
Living Area 1,137 SqFt
Beds 3
Baths 2
Year Built 1993
Property Type Duplex 2 Units
Ownership Type Related
APN CMBL M:R07-C L:4
Municipality CUMBERLAND
School District School Administrative District 51
21 Old Gray RdCumberland Center, ME 04021
Estimated Value $492,000
Living Area 1,248 SqFt
Beds 3
Baths 3
Year Built 1998
Property Type Single Family
Ownership Type Multiple
APN CMBL M:U21 L:5-C
Municipality CUMBERLAND
School District School Administrative District 51
22 Forest LnCumberland Center, ME 04021
Estimated Value $392,000
Living Area 860 SqFt
Beds 2
Baths 1
Year Built 1975
Property Type Single Family
Ownership Type Multiple
APN CMBL M:U22 L:60
Subdivision Forest Lane
School District School Administrative District 51
23 James WayWindham, ME 04062
Estimated Value $498,000
Living Area 1,680 SqFt
Beds 3
Baths 2
Year Built 2000
Property Type Single Family
Ownership Type Multiple
APN WINM M:17 B:25 L:A06
Municipality WINDHAM
School District Regional School Unit 14
25 Taylor LnGray, ME 04039
Estimated Value $625,000
Living Area 2,677 SqFt
Beds 4
Baths 3
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN GRAY M:069 B:041 L:040-021
Subdivision Quaker Rdg Sub
School District School Administrative District 15
23 Whitney RdCumberland Center, ME 04021
Estimated Value $858,000
Living Area 2,536 SqFt
Beds 4
Baths 2.5
Year Built 2014
Property Type Single Family
Ownership Type Related
APN CMBL M:R08 L:55 U:6
Municipality CUMBERLAND
School District School Administrative District 51
115 Lower Methodist RdCumberland Center, ME 04021
Estimated Value $286,000
Living Area 900 SqFt
Beds 3
Baths 1
Year Built 1992
Property Type Single Family
Ownership Type Related
APN CMBL M:R07 L:51
Municipality CUMBERLAND
School District School Administrative District 51