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
Deer Ln542$435,0001,604 Sq.Ft.10/11/2019Delta Dr733$680,5712,225 Sq.Ft.7/26/2024Denali Way223$564,0002,192 Sq.Ft.5/27/2008Depot St2232$530,9295,022 Sq.Ft.4/8/2025Derby Dr233$598,0001,866 Sq.Ft.11/2/2015Devon Rose Dr242$552,0001,676 Sq.Ft.N/ADiamond Point Rd243$668,0002,822 Sq.Ft.N/ADiane Way1N/AN/AN/AN/A8/5/2016Dirigo Ln631$465,3331,150 Sq.Ft.5/19/2025Discovery Way232$412,0001,468 Sq.Ft.11/2/2007Ditch Brook Xing321$411,0001,056 Sq.Ft.5/17/2005Dogleg Dr233$639,5002,153 Sq.Ft.9/2/2020Dominion Rd632$561,0001,725 Sq.Ft.8/12/2022Donna Rd442$505,5001,248 Sq.Ft.5/27/2025Doris Ave232$655,5001,948 Sq.Ft.4/12/2012Dow Ln832$530,1432,709 Sq.Ft.5/16/2023Down Home Rd542$547,2002,002 Sq.Ft.N/ADraco Ln232$443,0001,390 Sq.Ft.9/20/2022Dragonfly Dr333$553,0001,801 Sq.Ft.12/7/2018Driftwood Ln151$443,0002,170 Sq.Ft.12/14/2017Drive In Ln5N/AN/AN/A4,255 Sq.Ft.10/27/2021Duffy Dr232$573,5001,952 Sq.Ft.N/ADundee Rd1532$537,6671,773 Sq.Ft.11/30/2021Dunridge Cir1N/AN/AN/AN/AN/ADusty Rhoades Ln1732$519,5001,643 Sq.Ft.6/20/2023Dutton Hill Rd3732$490,7351,566 Sq.Ft.8/9/2024Dyer Pl332$442,0001,487 Sq.Ft.12/23/2019Dyke Ln222$638,000981 Sq.Ft.N/ADylan Way632$540,5001,530 Sq.Ft.1/4/2022Eagle Dr1831$434,7781,095 Sq.Ft.7/12/2024Easter Ave1832$494,4711,725 Sq.Ft.8/7/2023Easy Way1121$248,182833 Sq.Ft.11/27/2024Ebenezer Dr232$395,500967 Sq.Ft.5/17/2024Echo Ln232$541,5001,742 Sq.Ft.7/22/2016Edith Jeffords Rd632$514,8331,625 Sq.Ft.9/25/2024Elderberry Ln1132$576,8182,088 Sq.Ft.6/28/2023Eli Ln343$717,0002,900 Sq.Ft.9/22/2022Elizabeth Dr1632$514,7501,727 Sq.Ft.11/5/2024Elliott Dr242$481,5002,443 Sq.Ft.N/AElm St522$393,0001,183 Sq.Ft.7/16/2014Elmwood Dr631$414,1671,123 Sq.Ft.2/7/2025Emerald Way232$448,0001,230 Sq.Ft.2/10/2023Emerson Dr3932$439,6921,460 Sq.Ft.3/17/2025Emily Ln422$392,2501,184 Sq.Ft.11/14/2016Enterprise Dr1142N/A15,761 Sq.Ft.5/12/2022Environmental Way332$456,3331,250 Sq.Ft.11/30/2022Eric Rd1031$406,7001,238 Sq.Ft.9/21/2021Ernwood Hts231$437,000890 Sq.Ft.N/AEthan Dr342$645,6672,539 Sq.Ft.8/7/2020Evans Ridge Rd1932$663,1672,062 Sq.Ft.8/22/2024Evergreen Ln3132$549,9332,227 Sq.Ft.4/16/2025Fairway Dr423$334,2501,630 Sq.Ft.7/17/2024Falcon Rd121$367,0001,064 Sq.Ft.N/AFall Ridge Rd2532$584,9172,052 Sq.Ft.11/12/2024Falmouth Rd19032$450,1691,462 Sq.Ft.5/28/2025Family Cir521$429,000744 Sq.Ft.8/4/2023Farm View Dr643$616,8332,451 Sq.Ft.5/22/2025Fearon Ln232$402,0002,280 Sq.Ft.5/6/2016Fern Ave1121$418,1821,343 Sq.Ft.7/3/2008Fertile Valley Ln232$610,0001,946 Sq.Ft.8/21/2015Fieldcrest Rd542$453,0002,502 Sq.Ft.9/28/2006Figlia Way122$502,0001,672 Sq.Ft.N/AFinley Rd932$465,5001,775 Sq.Ft.4/1/2025Firefly Ln243$755,0002,862 Sq.Ft.7/31/2012Firwood Dr121$393,0001,054 Sq.Ft.N/AFlagship Ln233$685,0001,892 Sq.Ft.6/30/2023Fletcher Dr332$436,3331,598 Sq.Ft.7/28/2022Flintlock Dr643$762,5003,019 Sq.Ft.3/7/2020Florida Dr822$367,5001,184 Sq.Ft.1/17/2025Forbes Ln5232$448,8201,566 Sq.Ft.4/14/2025Forest Ave4522$420,841985 Sq.Ft.7/30/2021Forest Lake Is121$401,000906 Sq.Ft.N/AForsythia Ln2N/AN/AN/AN/AN/AFour Seasons Ln732$966,4292,344 Sq.Ft.11/5/2018Fox Run1432$521,0001,764 Sq.Ft.12/4/2023Franklin Dr3N/AN/AN/A52,954 Sq.Ft.7/8/2005Fraser Rd232$407,0001,153 Sq.Ft.N/AFreeman Ct933$941,1433,074 Sq.Ft.8/9/2024Frenchmans Ln732$604,1671,855 Sq.Ft.4/29/2022Frog Pond Rd532$522,0001,867 Sq.Ft.7/28/2023Frost Ln243$519,0002,243 Sq.Ft.3/28/2016Frye Rd221$436,5001,194 Sq.Ft.N/AGabriellas Way243$725,0002,468 Sq.Ft.1/10/2020Gambo Rd1743$594,2223,473 Sq.Ft.10/14/2022Garden Ln932$481,6671,353 Sq.Ft.9/6/2019Garrison Woods Dr932$494,1111,301 Sq.Ft.10/5/2022Gate Way421$384,500828 Sq.Ft.10/3/2012Gem Way232$553,0001,723 Sq.Ft.11/26/2013Gentle Breeze732$627,5001,931 Sq.Ft.1/31/2025Georges Ln732$606,8571,731 Sq.Ft.5/26/2021Gilman Dr121$434,000816 Sq.Ft.2/17/2009Gin Mill Ln733$826,3332,317 Sq.Ft.11/19/2024Glacial Hill Rd243$562,0001,739 Sq.Ft.N/AGlendale Rd422$543,0001,525 Sq.Ft.10/27/2006Goldfinch Dr632$496,8331,678 Sq.Ft.1/6/2020Gollums Way242$437,5001,254 Sq.Ft.11/4/2019Gordon Pl821$281,000724 Sq.Ft.8/12/2022Goshen Rd1032$576,5002,116 Sq.Ft.9/15/2023Graces Way332$598,0001,917 Sq.Ft.11/5/2021Grampas Vlg321$344,333805 Sq.Ft.2/19/202113 Ridge RdWestbrook, ME 04092
Estimated Value $594,000
Living Area 2,072 SqFt
Beds 6
Baths 2
Year Built 1983
Property Type Single Family
Ownership Type Individual
APN WSBR M:020-A L:016
Municipality WESTBROOK
School District Westbrook
70 Hillview RdGorham, ME 04038
Estimated Value $567,000
Living Area 1,838 SqFt
Beds 3
Baths 2.5
Year Built 1951
Property Type Single Family
Ownership Type Related
APN GRHM M:099 B:051 L:000
Subdivision Gorham Savings Bank
11 Ducati DrGorham, ME 04038
Estimated Value $748,000
Living Area 2,405 SqFt
Beds 3
Baths 3
Year Built 1983
Property Type Single Family
Ownership Type Individual
APN GRHM M:064 B:010 L:001
Subdivision Ducati Drive
39 Town CmnGorham, ME 04038
Estimated Value $639,000
Living Area 1,764 SqFt
Beds 3
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Related
APN GRHM M:109 B:010 L:501
Subdivision Village Green
33 Willow DrWestbrook, ME 04092
Estimated Value $575,000
Living Area 1,872 SqFt
Beds 3
Baths 2.5
Year Built 2014
Property Type Single Family
Ownership Type Multiple
APN WSBR M:021 L:026-H
Subdivision Willow Drive Sub
School District Westbrook
855 Bridgton RdWestbrook, ME 04092
Estimated Value $629,000
Living Area 1,466 SqFt
Beds 3
Baths 2
Year Built 2017
Property Type Single Family
Ownership Type Individual
APN WSBR M:021 L:033
Municipality WESTBROOK
School District Westbrook
1 Spring Water DrWindham, ME 04062
Estimated Value $467,000
Living Area 1,092 SqFt
Beds 2
Baths 2
Year Built 2018
Property Type Single Family
Ownership Type Individual
APN WINM M:39 B:9 L:F
Municipality WINDHAM
School District Regional School Unit 14
385 Mosher RdGorham, ME 04038
Estimated Value $820,000
Living Area 2,509 SqFt
Beds 5
Baths 3.5
Year Built 2014
Property Type Single Family
Ownership Type Multiple
APN GRHM M:031 B:006 L:202
Subdivision Mosher Road Sub
35 Old County RdWindham, ME 04062
Estimated Value $505,000
Living Area 1,425 SqFt
Beds 3
Baths 2
Year Built 1988
Property Type Single Family
Ownership Type Related
APN WINM M:9 B:50 L:C
Municipality WINDHAM
School District Regional School Unit 14
5 Gambo RdWindham, ME 04062
Estimated Value $439,000
Living Area 1,092 SqFt
Beds 3
Baths 2
Year Built 2017
Property Type Single Family
Ownership Type Individual
APN WINM M:41 B:11 L:1
Municipality WINDHAM
School District Regional School Unit 14
33 Webb RdWindham, ME 04062
Estimated Value $657,000
Living Area 1,995 SqFt
Beds 4
Baths 2.5
Year Built 2015
Property Type Single Family
Ownership Type Individual
APN WINM M:6 B:51 L:3
Municipality WINDHAM
School District Regional School Unit 14
23 Brackett Farm LnWindham, ME 04062
Estimated Value $352,000
Living Area 1,560 SqFt
Beds 3
Baths 2
Year Built 2003
Property Type Manufactured Homes
Ownership Type Related
APN WINM M:4 B:20 L:E
Municipality WINDHAM
School District Regional School Unit 14
14 Lawn AveGorham, ME 04038
Estimated Value $375,000
Living Area 1,008 SqFt
Beds 3
Baths 1
Year Built 1960
Property Type Single Family
Ownership Type Related
APN GRHM M:108 B:010 L:000
Subdivision Gorham Gdns Add 1
114 Gateway Commons DrGorham, ME 04038
Estimated Value $712,000
Living Area 2,172 SqFt
Beds 3
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN GRHM M:116 B:070 L:000
Subdivision Gateway Commons
34 Perry CtWestbrook, ME 04092
Estimated Value $766,000
Living Area 2,460 SqFt
Beds 3
Baths 4
Year Built 2021
Property Type Single Family
Ownership Type Individual
APN WSBR M:014 L:101
Municipality WESTBROOK
School District Westbrook
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