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
Kings Ln1633$617,2002,256 Sq.Ft.3/17/2025Kirkwood Dr42N/A$318,250290 Sq.Ft.8/1/2005Knox Rd332$411,6671,095 Sq.Ft.N/AKoorbano Ln632$475,3331,120 Sq.Ft.4/16/2025Kramers Way332$509,6671,520 Sq.Ft.10/23/2024Kristine Dr232$461,5001,400 Sq.Ft.7/1/2014Ladd Pl232$460,5001,538 Sq.Ft.12/28/2018Ladyslipper Dr732$969,1431,833 Sq.Ft.9/15/2023Lake Ave2032$983,3161,876 Sq.Ft.11/18/2024Lakeside Dr6121$463,3051,236 Sq.Ft.9/26/2024Lamb St543$419,4001,505 Sq.Ft.3/17/2025Lamplighter Rd2121$111,619884 Sq.Ft.N/ALanding Rd3N/AN/AN/A68,392 Sq.Ft.3/27/2017Land Of Nod Rd4832$538,0001,735 Sq.Ft.5/13/2025Lantern Ln2522$445,6001,264 Sq.Ft.1/30/2023Laredo Ln143$627,0003,025 Sq.Ft.N/ALaskey Rd2332$554,5911,629 Sq.Ft.5/23/2025Laura Dr232$504,0001,556 Sq.Ft.5/5/2014Lavender Ln243$593,5001,299 Sq.Ft.11/27/2019Lawrence Rd311$322,333793 Sq.Ft.5/7/2019Lazy Acres Ln633$504,0001,757 Sq.Ft.6/20/2023Ledge Hill Rd132$416,0001,170 Sq.Ft.5/15/2025Leeward Pass322$439,0001,127 Sq.Ft.5/16/2018Leighton Ln244$781,0001,829 Sq.Ft.7/20/2023Leisure Ln343$352,0002,737 Sq.Ft.5/6/2022Leonards Way2633$694,1602,066 Sq.Ft.11/14/2024Libby Hill Rd1221$352,636629 Sq.Ft.10/6/2022Liberty Ln232$513,0001,592 Sq.Ft.9/15/2020Lieutenants Dr833$662,2502,233 Sq.Ft.8/5/2022Lilac Dr1N/AN/AN/AN/AN/ALily Ln133$656,0001,992 Sq.Ft.N/ALimestone Ln331$363,3331,077 Sq.Ft.4/30/2025Lincoln Cir932$445,7501,377 Sq.Ft.3/28/2025Linda Ln631$459,167947 Sq.Ft.2/12/2009Links Ln133$640,0002,525 Sq.Ft.3/3/2022Linnell Rd3232$684,0362,109 Sq.Ft.11/19/2020Lionel Ln333$634,0001,904 Sq.Ft.10/29/2021Liquor Ln143$570,0001,040 Sq.Ft.6/14/2007Lisa Dr253$691,5002,959 Sq.Ft.8/5/2015Little Duck Pond Rd1222$358,125772 Sq.Ft.6/1/2023Little Duck Pond Road Ext1421$279,462587 Sq.Ft.12/2/2024Livrite Way342$695,3332,378 Sq.Ft.7/31/2019Lockland Dr1443$814,9292,986 Sq.Ft.8/19/2024Lolo Ln433$550,7501,379 Sq.Ft.2/16/2024Long Lane Rd1032$480,1001,325 Sq.Ft.10/10/2024Lookout Ln1721$126,176899 Sq.Ft.6/10/2014Loon Ln622$648,8331,456 Sq.Ft.5/7/2025Lorn Dr632$402,3331,325 Sq.Ft.8/23/2006Lotts Dr2132$446,7371,451 Sq.Ft.2/5/2024Lowell Rd532$421,5001,561 Sq.Ft.5/1/2018Lower Beach Rd521$430,2001,516 Sq.Ft.3/5/2025Lucinda Ln353$519,0002,240 Sq.Ft.12/20/2024Luckys Ln332$541,6671,392 Sq.Ft.11/29/2022Lucmick Ave231$399,500993 Sq.Ft.3/18/2014Lupine Ln132$511,0001,352 Sq.Ft.8/28/2020Lyden Way232$435,0001,144 Sq.Ft.8/12/2020Mabel Jean Ln231$390,000960 Sq.Ft.5/5/2015Macintosh Ln533$698,0002,500 Sq.Ft.4/28/2014Madison Rd932$460,0001,387 Sq.Ft.11/15/2024Magnolia Ln144$695,0002,924 Sq.Ft.12/17/2019Main St10432$468,3452,007 Sq.Ft.4/17/2025Majestic Hts732$492,2861,406 Sq.Ft.8/26/2016Malcolms Way221$311,500877 Sq.Ft.12/30/2013Malibu Ln432$454,7501,680 Sq.Ft.8/20/2024Mallards Way232$562,5002,135 Sq.Ft.2/17/2015Mallison Falls Rd584N/A2,790 Sq.Ft.4/4/2019Manchester Dr542N/A69,517 Sq.Ft.N/AMancini Rd232$482,0001,547 Sq.Ft.12/29/2017Mansfield Dr332$444,3331,896 Sq.Ft.6/17/2019Many Oaks Ln1533$944,2142,091 Sq.Ft.7/7/2020Maplewood Ave2231$416,4091,116 Sq.Ft.4/29/2025Marblehead Dr233$741,0002,294 Sq.Ft.3/16/2016Marc Ln242$589,0002,126 Sq.Ft.12/4/2023Marloda Dr133$840,0003,524 Sq.Ft.7/7/2020Marshall Valley Rd532$618,5002,203 Sq.Ft.6/11/2021Marston Rd3132$639,4291,264 Sq.Ft.12/17/2024Marzilli Way131$475,0001,104 Sq.Ft.N/AMatinicus Way1221$382,750767 Sq.Ft.9/29/2023Maverick Ln433$646,0001,997 Sq.Ft.9/21/2021Mayberry Rd253$573,5002,486 Sq.Ft.9/21/2020Maynard Rd1232$529,5001,671 Sq.Ft.9/2/2022Maysens Way1332$698,1821,933 Sq.Ft.5/2/2025Mcgoldrick Woods Rd1532$572,0002,296 Sq.Ft.4/14/2025Mclellan Knls232$564,5001,943 Sq.Ft.1/25/2021Meadowview Rd1642$524,9381,673 Sq.Ft.11/19/2022Meagans Way1422$349,0711,093 Sq.Ft.4/28/2025Mechanic St742$440,1431,606 Sq.Ft.5/16/2023Melody Ln1N/AN/AN/AN/A6/24/2019Melrose Way632$431,3331,374 Sq.Ft.5/24/2021Memory Ln332$476,6671,472 Sq.Ft.11/10/2022Mercedyle Dr232$408,000933 Sq.Ft.8/17/2017Meredith Dr2632$520,2921,320 Sq.Ft.4/30/2025Merganser Ln522$450,8001,240 Sq.Ft.7/17/2020Meyers Farm Rd1233$699,2502,757 Sq.Ft.11/30/2023Mic Mac Ln232$514,0001,189 Sq.Ft.4/30/2024Midnight Way332$525,0001,332 Sq.Ft.N/AMikes Way232$597,0001,906 Sq.Ft.1/9/2007Miles Rd232$529,5001,578 Sq.Ft.1/29/2024Millett Dr432$596,2501,928 Sq.Ft.12/9/2016Mill Pond Dr2221$455,6671,352 Sq.Ft.3/17/202518 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
8 Chickadee LnGorham, ME 04038
Estimated Value $517,000
Living Area 1,985 SqFt
Beds 3
Baths 2
Year Built 1989
Property Type Single Family
Ownership Type Individual
APN GRHM M:047 B:023 L:001
Municipality GORHAM
115 Mast RdWestbrook, ME 04092
Estimated Value $556,000
Living Area 1,998 SqFt
Beds 3
Baths 2.5
Year Built 2021
Property Type Single Family
Ownership Type Related
APN WSBR M:023 L:048-A
Municipality WESTBROOK
School District Westbrook
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
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
36 Meredith DrWindham, ME 04062
Estimated Value $508,000
Living Area 1,646 SqFt
Beds 3
Baths 1.5
Year Built 2018
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:38 L:D23
Subdivision Mystic Woods Sub
School District Regional School Unit 14
11 Twoey DrWindham, ME 04062
Estimated Value $554,000
Living Area 1,176 SqFt
Beds 3
Baths 2
Year Built 2016
Property Type Single Family
Ownership Type Related
APN WINM M:6 B:38 L:4
Municipality WINDHAM
School District Regional School Unit 14
101 Highland Cliff RdWindham, ME 04062
Estimated Value $479,000
Living Area 1,652 SqFt
Beds 3
Baths 1.5
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN WINM M:6 B:2 L:2
Municipality WINDHAM
School District Regional School Unit 14
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
50 Timberland DrWestbrook, ME 04092
Estimated Value $523,000
Living Area 1,344 SqFt
Beds 2
Baths 2.5
Year Built 2012
Property Type Single Family
Ownership Type Individual
APN WSBR M:014 L:006-H
Municipality WESTBROOK
School District Westbrook
11 Shamrock DrGorham, ME 04038
Estimated Value $709,000
Living Area 2,298 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Multiple
APN GRHM M:030 B:007 L:401
Municipality GORHAM
15 Connor DrGorham, ME 04038
Estimated Value $449,000
Living Area 1,444 SqFt
Beds 2
Baths 2.5
Year Built 2019
Property Type Condominium
Ownership Type Multiple
APN GRHM M:026 B:007 L:225-8
Subdivision Snowbird Condos
126 Main StWindham, ME 04062
Estimated Value $325,000
Living Area 912 SqFt
Beds 2
Baths 1
Year Built 1974
Property Type Single Family
Ownership Type Multiple
APN WINM M:40 B:27 L:A
Municipality WINDHAM
School District Regional School Unit 14
215 Gray RdGorham, ME 04038
Estimated Value $406,000
Living Area 1,488 SqFt
Beds 3
Baths 1
Year Built 1985
Property Type Single Family
Ownership Type Related
APN GRHM M:048 B:020 L:000
Municipality GORHAM
18 Exchange StGorham, ME 04038
Estimated Value $761,000
Living Area 2,128 SqFt
Beds 3
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Corporate
APN GRHM M:048 B:022 L:002
Municipality GORHAM
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