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
Grandview Point Rd621$627,333936 Sq.Ft.12/30/2019Granite Ridge Rd1032$606,7001,938 Sq.Ft.12/3/2024Grassington Rd522$525,8001,076 Sq.Ft.7/28/2023Gravel Hill Rd321$511,6671,169 Sq.Ft.3/9/2022Gray Rd20632$476,0631,896 Sq.Ft.6/10/2025Great Falls Rd343$726,0003,452 Sq.Ft.2/2/2016Greenwood Ter1031$382,900976 Sq.Ft.3/19/2024Griffin Dr232$454,5001,107 Sq.Ft.8/5/2005Gromble Way1831$454,2351,460 Sq.Ft.2/14/2025Gunpowder Mill Rd1833$637,2941,993 Sq.Ft.4/30/2025Hackett Rd1332$458,2221,342 Sq.Ft.8/25/2021Hague Rd531$408,7501,234 Sq.Ft.4/20/2018Half Moon Cv532$1,254,6002,448 Sq.Ft.12/11/2008Hall Rd3532$549,0654,172 Sq.Ft.9/30/2024Hammer Ln221$387,500827 Sq.Ft.9/14/2017Hancock Dr232$495,0001,556 Sq.Ft.3/22/2005Hang Rd233$583,0001,456 Sq.Ft.11/27/2017Hanna Brook Dr433$616,2501,951 Sq.Ft.5/5/2021Hansens Field Rd332$449,3331,515 Sq.Ft.9/26/2013Happy Ln322$738,333847 Sq.Ft.10/7/2022Harding Dr732$650,5712,183 Sq.Ft.6/9/2021Harmony Ln122$412,0001,344 Sq.Ft.N/AHarpers Way154$858,0002,892 Sq.Ft.4/28/2023Harriett Ave632$463,3331,426 Sq.Ft.6/17/2022Harrison Rd721$342,429974 Sq.Ft.6/26/2019Harvest Hill Rd6332$568,5561,647 Sq.Ft.5/30/2025Haskell Rd2132$500,3161,863 Sq.Ft.8/31/2023Haven Rd7132$487,8331,373 Sq.Ft.6/6/2025Hawkes Farm Rd422$451,7501,235 Sq.Ft.4/17/2018Hawthorne Dr1742$480,9411,549 Sq.Ft.2/10/2023Hayfield Ln2233$750,2862,223 Sq.Ft.6/10/2025Hazel Dr1332$667,5001,936 Sq.Ft.7/28/2023Hearthstone Dr233$655,0002,317 Sq.Ft.10/14/2022Heather Ln633$820,2502,743 Sq.Ft.2/27/2019Heathwood Dr842N/A3,018 Sq.Ft.1/17/2017Hemlock Dr643$865,4003,126 Sq.Ft.3/26/2025Hemon Cobb Rd1632$517,5001,491 Sq.Ft.6/17/2025Henderson Ct644$1,086,8333,459 Sq.Ft.11/17/2023Hereford Ln322$383,000873 Sq.Ft.10/1/2018Heritage Ln1432$708,3082,538 Sq.Ft.4/18/2025Hidden Pines Dr433$643,5002,397 Sq.Ft.12/20/2024Hideaway Ln221$367,500834 Sq.Ft.N/AHighland Cliff Rd12932$561,4141,783 Sq.Ft.9/17/2024Highland Shore Rd1532$621,2311,351 Sq.Ft.4/16/2025High St3232$434,5521,718 Sq.Ft.4/4/2025Hillcrest Rd1342$550,7691,814 Sq.Ft.11/8/2024Hinman Forest Rd134$1,033,0003,816 Sq.Ft.11/21/2017Holden Ln332$563,0002,168 Sq.Ft.10/9/2019Holly Ln832$516,1251,333 Sq.Ft.6/28/2024Holstein Dr432$466,5001,594 Sq.Ft.11/16/2021Homestead Ln332$575,0002,257 Sq.Ft.8/8/2016Honey Little Ln131N/A1,819 Sq.Ft.N/AHonnen Dr232$447,5001,176 Sq.Ft.10/31/2019Horizon Way232$415,5001,198 Sq.Ft.12/20/2019Howard Ave232$527,5002,163 Sq.Ft.5/5/2015Hoyt St632$521,8331,591 Sq.Ft.10/25/2019Huckleberry Ln332$493,6671,328 Sq.Ft.5/8/2017Hummingbird Ln332$840,0001,341 Sq.Ft.3/20/2020Hunts Dr2632$429,5001,369 Sq.Ft.11/7/2024Hussey Farm Rd121$419,000832 Sq.Ft.8/4/2011Hutchins Rd11N/A$355,000768 Sq.Ft.N/AIce House Rd732$702,1431,912 Sq.Ft.9/5/2017Idlewood Dr443$716,6672,317 Sq.Ft.11/9/2011Impala Way332$542,0001,810 Sq.Ft.9/25/2018Independence Dr1032$554,1001,966 Sq.Ft.11/30/2017Indian Cove Rd632$1,323,6671,591 Sq.Ft.8/19/2024Inkhorn Brook Rd432$502,2502,149 Sq.Ft.6/15/2021Inland Farm Rd1232$606,5832,070 Sq.Ft.6/26/2024Intervale Rd722$527,143914 Sq.Ft.7/31/2024Irish Spgs332$536,6671,853 Sq.Ft.10/15/2020Irving Ln134$792,0003,722 Sq.Ft.12/13/2024Isaac Dr232$547,0001,586 Sq.Ft.7/10/2023Island Dr1932$653,8891,356 Sq.Ft.3/22/2024Ivy Ln143$1,481,0003,818 Sq.Ft.N/AJacques Ln1232$399,6001,231 Sq.Ft.1/21/2020James Way1832$497,7061,839 Sq.Ft.9/27/2024Jasmine Way522$1,459,0001,290 Sq.Ft.9/16/2024Jeffrey Woods Rd333$771,0002,420 Sq.Ft.9/1/2022Jesses Acres332$466,0001,280 Sq.Ft.N/AJoes Rd732$530,6671,479 Sq.Ft.10/9/2024John Deere Rd1N/AN/AN/AN/A4/9/2007Johnson Rd4432$513,0001,593 Sq.Ft.11/15/2024Jones Hill Rd332$564,3331,989 Sq.Ft.1/10/2022Jules Dr244$624,5003,591 Sq.Ft.10/27/2023Junco Dr1333$464,9231,422 Sq.Ft.6/20/2025Juniper Dr332$637,6672,401 Sq.Ft.7/9/2024Kaitlyn Ct932$445,0001,752 Sq.Ft.4/12/2018Kardia Dr1N/AN/AN/AN/A9/30/2021Karen Ave1532$441,0671,344 Sq.Ft.3/28/2025Katahdin Ln631$495,8331,615 Sq.Ft.5/18/2022Kathryn Ct232$669,0002,695 Sq.Ft.N/AKaties Way333$677,3332,107 Sq.Ft.3/7/2024Keene Rd932$479,0001,423 Sq.Ft.10/27/2020Keeps Way1632$573,8001,415 Sq.Ft.7/8/2022Kelli Ln832$520,7501,606 Sq.Ft.11/30/2023Kennard Rd2032$959,7781,797 Sq.Ft.3/1/2024Kestrel Way242$849,0001,852 Sq.Ft.5/20/2020Keystone Dr643$879,4002,888 Sq.Ft.11/13/2019Kilty Way131$425,0001,092 Sq.Ft.N/AKineo Dr232$722,5002,269 Sq.Ft.1/6/2022214 Pleasant Valley RdCumberland Center, ME 04021
Estimated Value $1,014,000
Living Area 3,033 SqFt
Beds 4
Baths 3.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN CMBL M:R08 L:38-A
Subdivision Botany Place Condos
School District School Administrative District 51
45 Lakeside DrWindham, ME 04062
Estimated Value $480,000
Living Area 1,176 SqFt
Beds 2
Baths 2.5
Year Built 1954
Property Type Single Family
Ownership Type Individual
APN WINM M:35 B:42
Municipality WINDHAM
School District Regional School Unit 14
5 Glen Cove RdGray, ME 04039
Estimated Value $305,000
Living Area 736 SqFt
Beds 1
Baths 1
Year Built 1957
Property Type Single Family
Ownership Type Individual
APN GRAY M:075 B:202 L:028-000
Municipality GRAY
School District School Administrative District 15
10 Kathy LnCumberland Center, ME 04021
Estimated Value $515,000
Living Area 1,356 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Related
APN CMBL M:U19 L:24
Subdivision Allen Pk
School District School Administrative District 51
49 Brentwood RdWindham, ME 04062
Estimated Value $798,000
Living Area 2,000 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Single Family
Ownership Type Related
APN WINM M:13 B:51 L:C
Municipality WINDHAM
School District Regional School Unit 14
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
19 George RdCumberland Center, ME 04021
Estimated Value $503,000
Living Area 1,640 SqFt
Beds 3
Baths 2
Year Built 1929
Property Type Single Family
Ownership Type Multiple
APN CMBL M:U20 L:23
Subdivision Forest Homes
School District School Administrative District 51
10 Jordan CirGray, ME 04039
Estimated Value $473,000
Living Area 1,378 SqFt
Beds 3
Baths 2
Year Built 2009
Property Type Single Family
Ownership Type Related
APN GRAY M:072 B:040 L:018-007
Subdivision Bauer & Gilman Construction Ll
School District School Administrative District 15
409 Portland RdGray, ME 04039
Estimated Value $387,000
Living Area 1,096 SqFt
Beds 3
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN GRAY M:075 B:040 L:004-003
Municipality GRAY
School District School Administrative District 15
60 Old Colony LnCumberland Center, ME 04021
Estimated Value $754,000
Living Area 2,400 SqFt
Beds 4
Baths 2.5
Year Built 2016
Property Type Single Family
Ownership Type Related
APN CMBL M:R07 L:70 U:18
Subdivision Old Colony Ests Ph 3
School District School Administrative District 51
8 Forest LnCumberland Center, ME 04021
Estimated Value $399,000
Living Area 1,236 SqFt
Beds 3
Baths 1
Year Built 1979
Property Type Single Family
Ownership Type Related
APN CMBL M:U22 L:54
Subdivision Mabel Wilson Sub
School District School Administrative District 51
128 Orchard RdCumberland Center, ME 04021
Estimated Value $656,000
Living Area 2,263 SqFt
Beds 4
Baths 2.5
Year Built 1984
Property Type Single Family
Ownership Type Mixed
APN CMBL M:R08 L:51-B
Municipality CUMBERLAND
School District School Administrative District 51
46 Dutton Hill RdWindham, ME 04062
Estimated Value $361,000
Living Area 1,352 SqFt
Beds 2
Baths 1
Year Built 1900
Property Type Single Family
Ownership Type Individual
APN WINM M:20 B:36
Municipality WINDHAM
School District Regional School Unit 14
64 Deer Run DrCumberland Center, ME 04021
Estimated Value $641,000
Living Area 1,008 SqFt
Beds 3
Baths 1
Year Built 2018
Property Type Single Family
Ownership Type Individual
APN CMBL M:R07 L:2 U:E
Municipality CUMBERLAND
School District School Administrative District 51
297 Portland RdGray, ME 04039
Estimated Value $446,000
Living Area 1,708 SqFt
Beds 4
Baths 1.5
Year Built 1900
Property Type Single Family
Ownership Type Corporate
APN GRAY M:069 B:041 L:029-000
Municipality GRAY
School District School Administrative District 15
12 Grist Mill RdFalmouth, ME 04105
Estimated Value $596,000
Living Area 1,468 SqFt
Beds 2
Baths 3.5
Year Built 1983
Property Type Single Family
Ownership Type Related
APN FMTH M:U36 B:014
Subdivision Poplar Rdg Ii