Cumberland, ME Homes

• 

  

  

  /75

  $825,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,580 Sq Ft

  27 Lake Ave, Windham, ME 04062

  Welcome to 27 Lake Avenue, a stunning 3-bedroom, 2.5-bath chalet-style home with 2,580 square feet of beautifully finished living space and deeded right of way to Sebago Lake—complete with shared dock and private boat morring access just across the street. Designed for comfort and lake life, this home features an open-concept kitchen, dining, and living area with cathedral ceilings, a cozy gas

  

  Nicholas Dambrie

  Keller Williams Realty

  (844) 708-4282

  

  27 Lake Ave, Windham, ME 04062
• 

  Explore Windham

• 

  

  

  /20

  $5,730 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  12 Eagle Dr Unit ID1255625P, Windham, ME 04062

  Welcome to this charming 2-bedroom, 1-bath cottage on Pettengill Pond, offering a serene retreat with 50 feet of water frontage and stunning water views. The main floor features an open concept kitchen and living area, where the couch conveniently pulls out for additional sleeping space. Both bedrooms and the full bath are also located on the main floor, while the walkout basement provides extra

  12 Eagle Dr Unit ID1255625P, Windham, ME 04062
• 

  

  

  /79

  $699,000 Sold Aug 01, 2025

  • 3,039 Sq Ft
  • $230/SF
  • 46 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  9 Strawberry Ln, Windham, ME 04062

  Spend your days during all four of Maine's vibrant seasons relaxing in your new home overlooking the Elizabeth Farms Pond. This spacious property on Strawberry Lane boasts 3 large bedrooms, including a substantial primary suite with a walk-in closet, full bathroom and a loft which would make the ideal office, reading nook or craft area. Among the bedrooms and common bathroom on the 2nd floor,

  Katie Brooke Vitalius Real Estate Group, LLC

  

  9 Strawberry Ln, Windham, ME 04062
• 

  

  

  /59

  Est $867,862 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft

  5 Pride Ln, Windham, ME 04062

  

  5 Pride Ln, Windham, ME 04062
• 

  

  /2

  $165,000

  • Land
  • 0.69 Acre
  • $239,130 per Acre

  00 Dusty Rhoades Ln, Windham, ME 04062

  Don't miss this opportunity to own .69 acres in a desirable Windham neighborhood. Offering public water and plenty of privacy, this is the perfect spot for your new home! Lot size does meet the requirements for a duplex (town approval needed). Close to North Windham amenities and lakes, and a short commute to Portland.

  

  Ashley Fearon

  A Team Realty

  (207) 820-0758

  

  00 Dusty Rhoades Ln, Windham, ME 04062
• 

  

  /17

  $6,830 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  38 Brentwood Rd Unit ID1255706P, Windham, ME 04062

  Experience the charm of lakefront living in this delightful 2-bedroom, 1-bath cottage on Highland Lake in Windham. With a capacity for up to 5 guests, this home offers an open living space with picturesque views of the lake from both the living room and kitchen. Both bedrooms are conveniently located on the main floor and feature full-size beds, while a loft provides additional sleeping space

  38 Brentwood Rd Unit ID1255706P, Windham, ME 04062
• 

  

  /53

  $609,000 Sold Jul 31, 2025

  • 2,118 Sq Ft
  • $288/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  80 Woodland Rd, Windham, ME 04062

  Privacy galore, perfect for entertaining, and just a few minutes from everything in Windham. This custom crafted home has been meticulously maintained and continually updated. The open concept kitchen has plenty of seating and opens through a newly finished sunroom to the large decks and patio with a gazebo, granite high-top bar, extra covered canopy seating, and stone patio with a built in

  Matt Trudel Five Star Realty

  

  80 Woodland Rd, Windham, ME 04062
• 

  

  /31

  Est $436,488 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  10 Reba Ln, Windham, ME 04062

  

  10 Reba Ln, Windham, ME 04062
• 

  

  /22

  $599,900 Pending

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  345 Mount Hunger Shore Rd, Gray, ME 04039

  Welcome to your private getaway on the shores of Little Sebago Lake! This two-bedroom rustic camp offers the perfect blend of charm, simplicity, and waterfront living. Tucked away on a peaceful and private lot, you'll enjoy 100 feet of pristine sandy beach, ideal for swimming, boating, or simply soaking in the summer sun.Wake up to breathtaking sunrise views over the lake and spend your

  

  Ashley Fearon

  A Team Realty

  (207) 656-1088

  

  345 Mount Hunger Shore Rd, Gray, ME 04039
• 

  

  /20

  $2,250 per month

  • 2 Beds
  • 2 Baths
  • Condo for Rent

  33 Baxter Woods Trail, Windham, ME 04062

  Property Id: 2008558Discover this beautiful 2-bedroom, 1-bath winter rental, available October 1st, 2025 through May 30th, 2026 — with flexible start and end dates (as early as September 1st)!This inviting condo comes fully furnished and stocked with everything you need. Inside, you'll find a spacious kitchen with a center island, a cozy living area, and a full bath on the main

  33 Baxter Woods Trail, Windham, ME 04062
• 

  

  /14

  $950,395 Sold Jul 31, 2025

  • 2,234 Sq Ft
  • $425/SF
  • 0 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  27 Daybreak Ln Unit 27, Windham, ME 04062

  Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Luxury Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 21 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes offer both first and second floor primary suite options. Multi-generational, Companion, and Guest Friendly, owners of these units can

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  27 Daybreak Ln Unit 27, Windham, ME 04062
• 

  

  /34

  Est $334,413 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 682 Sq Ft

  566 Roosevelt Trail, Windham, ME 04062

  

  566 Roosevelt Trail, Windham, ME 04062
• 

  

  /35

  $465,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  19 Twoey Dr, Windham, ME 04062

  Wonderfully Maintained Ranch In A Desirable Windham Neighborhood. Open concept kitchen/living/dining area, great backyard, primary bedroom suite with attached full bath. Spacious kitchen with cathedral ceilings, center island, and sharp black Whirlpool appliances. Wood and tile flooring, back deck overlooks a great backyard. Gas fireplace in the living room. Full basement sets up well to be

  

  Harrison Wolfington

  Your Home Sold Guaranteed Realty

  (207) 306-2871

  

  19 Twoey Dr, Windham, ME 04062
• 

  

  /13

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  8 Cornerbrook Cir Unit B, Windham, ME 04062

  Property Id: 2017969Welcome to your new home at 8 Cornerbrook Cir in Windham, ME! This charming 2 bed, 1 bath multi_family unit offers a cozy living space with included utilities and pet-friendly options. Enjoy amenities like a refrigerator, dishwasher, and off-street parking. Don't miss out on this gem near parks, available for rent starting July 14th, 2025 at $2200/month. Act fast

  8 Cornerbrook Cir Unit B, Windham, ME 04062
• 

  

  /108

  $1,800,000 Sold Jul 30, 2025

  • 2,500 Sq Ft
  • $720/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2009

  147 Sand Bar Rd, Windham, ME 04062

  The Crown Jewel of Little Sebago - A Lakeside Legacy! Welcome to an extraordinary waterfront retreat, offering the finest in Maine lakefront living. Perfectly situated on 210 feet of level, sandy shoreline, this custom-crafted lake house is a rare gem on the shores of Little Sebago Lake, a picturesque 1,898-acre body of water renowned for its natural beauty, recreational opportunities, and

  Fred Andrews Spectrum Real Estate

  

  147 Sand Bar Rd, Windham, ME 04062
• 

  

  /68

  Est $487,612 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,800 Sq Ft

  381 Gray Rd, Windham, ME 04062

  

  381 Gray Rd, Windham, ME 04062
• 

  

  /50

  $745,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,708 Sq Ft

  893 River Rd, Windham, ME 04062

  Welcome to a spacious and stately custom Cape beautifully positioned on a private 2.5‑acre parcel. This well-maintained home showcases over 3700 sq ft with 4 bedrooms, 3.5 bathrooms, and a flexible layout that includes a spacious in-law or guest suite above the oversized 3-car garage. The eat-in kitchen features granite countertops, a center island, beautiful cabinetry, and updated

  

  Yulia Glasgow

  Maine Real Estate Co

  (603) 264-7839

  

  893 River Rd, Windham, ME 04062
• 

  

  /14

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  8 Cornerbrook Cir, Windham, ME 04062

  This 950 sq. ft. property at 8 Cornerbrook Cir features 2 bedrooms and 1 bathroom. The living room offers ample space for relaxation, while the bathroom includes a tub/shower combination. Each bedroom is designed for comfort and functionality. The property is equipped with heating and ceiling fans for climate control. Additional amenities include handrails for safety and washer/dryer hookups for

  8 Cornerbrook Cir, Windham, ME 04062
• 

  

  /36

  $450,000 Sold Jul 29, 2025

  • 1,418 Sq Ft
  • $317/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  13 Junco Dr Unit 6, Windham, ME 04062

  Perfect Blend of Style, Comfort and Convenience! Welcome to 13 Junco Drive where HOA covers exterior maintenance- You just sit back and relax!Situated in a sought-after area with direct access to Walking, Hiking, & Skiing Trails-Perfect for Nature Lovers-this elegant condo boasts a well laid out living space with 3 bedrooms, 2.5 bath, 1 car garage and a full, unfinished basement for extra

  Neeta Signh Keller Williams Realty

  

  13 Junco Dr Unit 6, Windham, ME 04062
• 

  

  /38

  Est $563,000 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,592 Sq Ft

  308 Pope Rd, Windham, ME 04062

  

  308 Pope Rd, Windham, ME 04062
• 

  

  /65

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  158 Mount Hunger Shore Rd, Windham, ME 04062

  This thoughtfully designed 3-bedroom, 2-bath home offers the perfect blend of natural light, open space, and peaceful surroundings. Soaring cathedral ceilings and oversized windows fill the main living area with sunlight, creating an uplifting and welcoming atmosphere.Enjoy a flexible floor plan with a finished room on the ground level—perfect for a guest suite, home office, or bonus

  

  Deja Lett

  Keller Williams Realty

  (207) 762-7934

  

  158 Mount Hunger Shore Rd, Windham, ME 04062
• 

  

  /20

  $364,500 Sold Jul 28, 2025

  • 1,664 Sq Ft
  • $219/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1979

  270 Falmouth Rd, Windham, ME 04062

  Affordable 2 bedroom ranch waiting for you to call home. Oversized living room and two large bedrooms, all on 2 acres of land. Private back yard and an adorable screened in front porch where you can relax with your morning coffee. This won't last long!

  Neile Nelson Century 21 First Choice Realty

  

  270 Falmouth Rd, Windham, ME 04062
• 

  

  /60

  Est $591,238 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,892 Sq Ft

  65 Chute Rd, Windham, ME 04062

  

  65 Chute Rd, Windham, ME 04062
• 

  

  /9

  $719,000

  • 4 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  31 Cooper Ridge Rd, Windham, ME 04062

  Brand New To-Be-Built Home in Windham!Welcome to your future dream home in a charming new six-lot subdivision—offering privacy, convenience, and the chance to make it truly yours! Located just minutes from Westbrook and Portland, this to-be-built 4-bedroom home sits on a generous .71-acre lot with the foundation already in place, so things are moving fast!With 2,290 sq. ft. of

  

  Ashley Fearon

  A Team Realty

  (207) 503-2141

  

  31 Cooper Ridge Rd, Windham, ME 04062
• 

  

  /56

  $760,000 Sold Jul 25, 2025

  • 2,692 Sq Ft
  • $282/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  7 Revolution Dr, Windham, ME 04062

  Welcome to 7 Revolution Drive! A Turn-Key property nestled in the highly sought after and coveted Majestic Woods community. Step into this beautifully maintained Brush & Hammer home, offering 3 bedrooms, 2.5 baths, and over 2,500 square feet of thoughtfully designed living space. This 2020-built residence offers the rare combination of community charm with enhanced privacy - with only one direct

  Edith Fontai Maureen Zemrak Locations Real Estate Group LLC

  

  7 Revolution Dr, Windham, ME 04062
• 

  

  /41

  Est $680,202 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,923 Sq Ft

  25 Running Brook Rd, Windham, ME 04062

  

  25 Running Brook Rd, Windham, ME 04062
• 

  

  /46

  $975,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,287 Sq Ft

  132 Mineral Spring Rd Unit 1, Windham, ME 04062

  This newly built Sebago Lake property is set in a one of the area's most sought-after neighborhoods. Ideally situated, it provides easy access to shopping, restaurants, skiing, and a wide range of water sports and outdoor recreation. The main floor features high ceilings, expansive windows and white oak hardwood flooring throughout. A spacious living room with a gas fireplace offers partial

  David Costello Keller Williams Realty

  

  132 Mineral Spring Rd Unit 1, Windham, ME 04062
• 

  

  /58

  $1,190,000 Sold Jul 25, 2025

  • 3,787 Sq Ft
  • $314/SF
  • 8 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2017

  11 Lieutenants Dr, Windham, ME 04062

  Welcome to 11 Lieutenants Drive, Windham, ME - where modern farmhouse elegance meets community warmth and sustainable luxury.Nestled at the end of a private cul-de-sac, this beautifully crafted home sits on 3.78 acres in one of Windham's most sought-after neighborhoods. This meticulously built 4-bedroom modern farmhouse offers the perfect blend of timeless style and cutting-edge

  Vicki Kennedy RE/MAX Oceanside

  

  11 Lieutenants Dr, Windham, ME 04062
• 

  

  /5

  Est $168,190 Not Listed For Sale

  211 Falmouth Rd, Windham, ME 04062

  

  211 Falmouth Rd, Windham, ME 04062
• 

  

  /69

  $749,000

  • 3 Beds
  • 2.5 Baths
  • 2,822 Sq Ft

  14 Rocklinn Dr, Windham, ME 04062

  This beautiful, meticulously maintained home is ready for its next owner. The home sits in the desirable Rocklinn neighborhood, on a private, but close to everything lot. The first-floor master suite is spacious and well laid out, the wide pine floors are eye catching and ooze old school charm, and the open kitchen with quartz counter tops and walk-in pantry are enviable. A large bonus room

  Richard Yost NextHome NorthEast Realty

  

  14 Rocklinn Dr, Windham, ME 04062
• 

  

  /31

  $234,000 Sold Jul 25, 2025

  • 1,000 Sq Ft
  • $234/SF
  • 95 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1984

  22 Whites Bridge Rd Unit 22, Windham, ME 04062

  It's easy to bloom when you're planted at 22 Whites Bridge Road! A serene setting and the simplicity of condominium living make this end-unit 2-bedroom, 1.5-bath abode a warm welcome home. Inside, rustic wood beams, lofty ceilings, and an open, airy layout make relaxing, dining, and entertainment an easy endeavor. The cheerful kitchen makes for pleasant meal prep, and the window over the sink

  Bridget King Jason Miller King + Miller Real Estate

  

  22 Whites Bridge Rd Unit 22, Windham, ME 04062
• 

  

  /41

  Est $409,798 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  148 Varney Mill Rd, Windham, ME 04062

  

  148 Varney Mill Rd, Windham, ME 04062
• 

  

  /27

  $650,000

  • 4 Beds
  • 2 Baths
  • 3,657 Sq Ft

  5 Pemberly Dr, Windham, ME 04062

  **OPEN HOUSE: Saturday, August 2nd from 11:00 AM to 12:30 PM with Cody Macfarlane& Sunday, August 3rd from 12:00 PM to 1:30 PM with Samantha Hale**Instant Equity!This property is already building value with 2 APPROVED BUILDABLE LOTS INCLUDED —a rare opportunity totaling 6 beautiful acres. Live in the well-maintained farmhouse-style Cape while exploring options to sell or develop

  Kayla Brown Maine Real Estate Co

  

  5 Pemberly Dr, Windham, ME 04062
• 

  

  /14

  $915,629 Sold Jul 24, 2025

  • 2,234 Sq Ft
  • $410/SF
  • 0 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  21 Daybreak Ln Unit 21, Windham, ME 04062

  Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Luxury Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 21 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes offer both first and second floor primary suite options. Multi-generational, Companion, and Guest Friendly, owners of these units can

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  21 Daybreak Ln Unit 21, Windham, ME 04062
• 

  

  /40

  Est $398,804 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,117 Sq Ft

  45 Hunts Dr, Windham, ME 04062

  

  45 Hunts Dr, Windham, ME 04062
• 

  

  /56

  $750,000

  • 4 Beds
  • 3.5 Baths
  • 3,128 Sq Ft

  32 Kings Ln, Windham, ME 04062

  This beautiful Colonial set on a grassy knoll with trees lightly surrounding provides views of surrounding fields and distant hills. A Spacious home with large eat-in kitchen, oversized island and breakfast table area create space for the cook or guests who drop by to chat. A more formal dining area and living room provide seating for those special occasions. Upstairs is the master suite with

  Anthony Poulin Meservier & Associates

  

  32 Kings Ln, Windham, ME 04062
• 

  

  /64

  $385,000 Sold Jul 23, 2025

  • 2,240 Sq Ft
  • $172/SF
  • 13 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1966

  514 Gray Rd, Windham, ME 04062

  3 bedroom ranch with 2 car garage and two storage sheds. Partially finished full walkout basement. Great location close to schools, shopping and Portland.

  Peter Forbes Pine Tree Realty of Maine

  

  514 Gray Rd, Windham, ME 04062
• 

  

  /50

  Est $619,451 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,157 Sq Ft

  34 Scottland Rd, Windham, ME 04062

  

  34 Scottland Rd, Windham, ME 04062
• 

  

  /43

  $775,000

  • 6 Beds
  • 3 Baths
  • 4,170 Sq Ft

  11 Haven Rd, Windham, ME 04062

  Tucked away on a quiet street in Windham, this unique home offers exceptional space and value with an additional apartment. The main home lives like a 5-bedroom, 2-bath layout, anchored by an oversized fireplace that gives chalet-style warmth and character. The updated kitchen overlooks a large, private backyard — perfect for gatherings or quiet evenings.The primary suite is located above

  Christopher Davis Real Broker

  

  11 Haven Rd, Windham, ME 04062
• 

  

  /14

  $545,000 Sold Jul 22, 2025

  • 1,656 Sq Ft
  • $329/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  122 Pope Rd, Windham, ME 04062

  Showcasing exceptional craftsmanship throughout, this home is a true testament to quality and detail. Blending classic charm with modern updates, this thoughtfully restored home is a rare find-located just minutes from the heart of Windham.Step inside to discover a bright and airy open-concept living area that seamlessly flows to the kitchen and dining areas, perfect for both relaxing and

  Meghan Connolly Landing Real Estate

  

  122 Pope Rd, Windham, ME 04062

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