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
Cajun Ct422$479,0001,363 Sq.Ft.8/21/2020Calla Way1N/AN/AN/AN/AN/ACameron Ln722$621,6671,624 Sq.Ft.9/24/2024Camp Dr221$422,000858 Sq.Ft.3/20/2017Canada Hill Rd1132$503,3001,530 Sq.Ft.4/28/2023Canal Ct243$1,384,5002,864 Sq.Ft.11/29/2018Candlewyck Rd1221$445,2001,276 Sq.Ft.12/1/2022Canterbury Ln232$474,5001,272 Sq.Ft.6/14/2021Canyon Way233$681,0002,269 Sq.Ft.N/ACape View Dr232$2,091,0002,112 Sq.Ft.2/3/2021Captain Thomas Dr332$553,5001,470 Sq.Ft.2/18/2020Cardinal Ln1032$521,9001,729 Sq.Ft.7/8/2024Carignan Dr632$430,8001,263 Sq.Ft.11/1/2024Carmichael Ln933$676,2501,862 Sq.Ft.3/7/2023Carol Dr432$588,0001,972 Sq.Ft.11/21/2022Carpenters Way332$410,6671,295 Sq.Ft.N/ACarriage Hill Dr1842$602,1672,275 Sq.Ft.11/8/2019Cartland Rd842$571,2862,226 Sq.Ft.10/4/2022Castoro Dr333$689,0003,557 Sq.Ft.6/3/2022Caterina Woods111$369,000676 Sq.Ft.N/ACattle Dr222$473,0001,294 Sq.Ft.N/ACedar Ln1431$452,0001,314 Sq.Ft.5/20/2024Center Brook Dr433$628,7502,539 Sq.Ft.9/30/2016Cessna Ln1N/AN/AN/AN/AN/AChaffin Pond Preserve1N/AN/AN/AN/AN/AChallenge Dr222$528,0001,777 Sq.Ft.7/31/2012Chamberlain Dr3N/AN/AN/AN/AN/ACharlan Ln832$523,2861,505 Sq.Ft.4/12/2023Chelsa Ln531$401,0001,279 Sq.Ft.N/ACherry Ln3N/AN/AN/A6,200 Sq.Ft.5/17/2024Chestnut Ave731$402,5711,139 Sq.Ft.4/22/2021Chickadee Ln222$548,0001,275 Sq.Ft.N/AChimera Hill Rd932$525,6251,681 Sq.Ft.5/23/2024Chipmunk Dr431$398,5001,006 Sq.Ft.6/3/2013Chloe Dr233$482,0001,722 Sq.Ft.11/25/2019Christmas Tree Way242$569,0001,980 Sq.Ft.6/13/2023Chute Rd7232$562,1041,595 Sq.Ft.12/4/2024Cider Mill Ln433$670,0002,575 Sq.Ft.9/30/2022Clairmont Rd1731$676,1761,399 Sq.Ft.11/26/2024Claman Dr832$613,5001,324 Sq.Ft.7/17/2024Clark Dr432$386,0001,022 Sq.Ft.10/14/2022Clay Hill Dr242$577,0002,170 Sq.Ft.4/12/2018Clearwater Cv145$3,182,0006,452 Sq.Ft.8/14/2020Cliff Dr733$628,7142,352 Sq.Ft.1/31/2025Cloutier Ln442$524,7501,455 Sq.Ft.3/30/2016Clover Ln423$770,0001,455 Sq.Ft.8/16/2019Cobalt Ct632$600,0001,925 Sq.Ft.7/21/2021Cobb Farm Rd233$632,5001,895 Sq.Ft.4/9/2025Coffee Way242$637,0001,980 Sq.Ft.4/12/2006Colby Dr1132$571,7001,675 Sq.Ft.11/20/2024Cold Bear Dr632$560,4001,785 Sq.Ft.3/24/2022Cole Rd432$528,0001,353 Sq.Ft.1/8/2019Colley Brook Dr732$490,4291,716 Sq.Ft.1/27/2025Collins Pond Rd1732$415,7331,887 Sq.Ft.9/30/2022Collinwood Cir2532$427,0831,331 Sq.Ft.2/14/2025Colonial Park Dr842$512,3751,653 Sq.Ft.2/23/2024Commons Ave13N/AN/AN/A6,157 Sq.Ft.N/AConant Dr332$452,0001,467 Sq.Ft.5/23/2024Concord Dr143$701,0002,630 Sq.Ft.9/24/2018Conifer Dr4422$399,114954 Sq.Ft.4/30/2025Connemara Crk532$562,0001,609 Sq.Ft.3/21/2025Conrad Dr832$512,6252,090 Sq.Ft.1/17/2018Cook Rd2032$562,7781,768 Sq.Ft.8/23/2024Cooper Rdg532$471,2501,634 Sq.Ft.10/23/2020Cornerbrook Cir1532$455,0771,705 Sq.Ft.10/28/2024Cornfield Vw132$485,0001,896 Sq.Ft.11/18/2020Corsettis Way233$589,5001,993 Sq.Ft.10/29/2014Cosmic Way621$238,167833 Sq.Ft.4/12/2024Cottage Rd10232$524,8371,344 Sq.Ft.6/3/2025Cotton Dr921$402,444884 Sq.Ft.8/31/2023Country Ln621$432,6671,605 Sq.Ft.2/23/2017Cove Rd332$587,3331,344 Sq.Ft.11/13/2017Covered Bridge Rd1222$527,7501,417 Sq.Ft.6/2/2023Coyote Ct222$450,5001,572 Sq.Ft.12/14/2015Crabapple Rd532$492,2501,511 Sq.Ft.8/12/2016Craig Rd722$593,6671,833 Sq.Ft.2/1/2023Creamery Way1N/AN/AN/AN/A8/20/2014Crescent Ave2632$1,080,2691,755 Sq.Ft.8/23/2024Cresthaven Rd532$629,4001,458 Sq.Ft.11/4/2024Crimson Dr2N/A1N/A4,424 Sq.Ft.4/14/2008Critter Dr1032$398,6001,235 Sq.Ft.5/17/2024Crockett Rd732$724,2861,290 Sq.Ft.2/10/2023Crossridge Dr1033$801,4442,774 Sq.Ft.5/14/2025Crown Pt234$1,339,5004,858 Sq.Ft.3/14/2022Crystal Ln543$686,0002,816 Sq.Ft.7/1/2019Cunningham Dr132$486,0001,428 Sq.Ft.11/19/2024Curtis Dr1421$441,1001,230 Sq.Ft.5/22/2020Cutting Corners Ln232$445,0001,688 Sq.Ft.4/25/2025Cyprus Hill Dr522$497,5001,227 Sq.Ft.5/26/2023Dads Way332$484,6671,152 Sq.Ft.5/7/2021Daigle Dr1N/AN/AN/AN/AN/ADakota Dr1531$442,6671,238 Sq.Ft.9/16/2021Dale Ln731$397,2861,061 Sq.Ft.3/5/2018Dallas Dr263$1,207,0001,248 Sq.Ft.12/14/2023Dalten Pines Rd1521$269,667902 Sq.Ft.12/30/2024Damien Dr632$536,6671,874 Sq.Ft.4/29/2024Danielle Dr712N/A9,522 Sq.Ft.9/20/2019Dartmouth Pl932$613,0001,911 Sq.Ft.6/6/2024Davidson Dr122$533,0001,186 Sq.Ft.3/21/2013Davis Ave632$482,0001,496 Sq.Ft.9/2/202278 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
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
25 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
12 Androscoggin StWindham, ME 04062
Estimated Value $512,000
Living Area 1,915 SqFt
Beds 5
Baths 3
Year Built 1910
Property Type Single Family
Ownership Type Multiple
APN WINM M:37 B:12
Municipality WINDHAM
School District Regional School Unit 14
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
48 Sunset RdFalmouth, ME 04105
Estimated Value $600,000
Living Area 1,518 SqFt
Beds 2
Baths 2
Year Built 1920
Property Type Single Family
Ownership Type Multiple
APN FMTH M:HL3 B:008
Subdivision Southeast Shore Hlnd Lk
49 Gordon Farms RdGorham, ME 04038
Estimated Value $812,000
Living Area 2,424 SqFt
Beds 5
Baths 2.5
Year Built 2007
Property Type Single Family
Ownership Type Related
APN GRHM M:045 B:023 L:417
Subdivision Gordon Farms Sub Ph 2
8 Revolution DrWindham, ME 04062
Estimated Value $678,000
Living Area 2,096 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Single Family
Ownership Type Individual
APN WINM M:6 B:63 L:13 U:1
Municipality WINDHAM
School District Regional School Unit 14
43 Nasson AveWestbrook, ME 04092
Estimated Value $379,000
Living Area 685 SqFt
Beds 3
Baths 1
Year Built 1970
Property Type Single Family
Ownership Type Individual
APN WSBR M:043 L:060-B
Municipality WESTBROOK
School District Westbrook
13 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
67 Highland Cliff RdWindham, ME 04062
Estimated Value $655,000
Living Area 2,500 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN WINM M:6 B:7 L:A
Municipality WINDHAM
School District Regional School Unit 14
18 Martin DrGorham, ME 04038
Estimated Value $797,000
Living Area 2,835 SqFt
Beds 4
Baths 2.5
Year Built 1998
Property Type Single Family
Ownership Type Multiple
APN GRHM M:044 B:006 L:004
Municipality GORHAM
255 Methodist RdWestbrook, ME 04092
Estimated Value $588,000
Living Area 1,866 SqFt
Beds 3
Baths 1
Year Built 1977
Property Type Single Family
Ownership Type Related
APN WSBR M:012 L:006-A
Municipality WESTBROOK
School District Westbrook
26 Stillwater Dr #25Westbrook, ME 04092
Estimated Value $592,000
Living Area 1,680 SqFt
Beds 4
Baths 2.5
Year Built 2019
Property Type Condominium
Ownership Type Multiple
APN WSBR M:010 B:025 L:006
Municipality WESTBROOK
School District Westbrook
215 Huston RdGorham, ME 04038
Estimated Value $341,000
Living Area 900 SqFt
Beds 2
Baths 1
Year Built 1953
Property Type Single Family
Ownership Type Individual
APN GRHM M:111 B:041 L:000
Municipality GORHAM
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