Homes for Sale near Windham Middle School

• 

  

  

  /96

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 3,555 Sq Ft

  35 Woldbrook Dr, Windham, ME 04062

  Welcome to the highly desirable Windemere neighborhood on Sebago Lake. This beautifully maintained custom Colonial offers over 3,550 sq. ft. of finished living space with a flexible floor plan designed to accommodate today's multi-generational living needs, including the potential for an in-law suite with kitchenette above the garage.The home features 4-5 bedrooms and 3.5 baths, including

  Jackie Griffeth Krainin Real Estate

  

  35 Woldbrook Dr, Windham, ME 04062
• 

  Explore Windham Middle School

• 

  

  /2

  $275,000

  • Land
  • 2.96 Acres
  • $92,905 per Acre

  0 Cook, Windham, ME 04062

  Rare opportunity to build your dream home/getaway destination or private sanctuary away from it all, yet with conveniences of daily living still nearby. Nestled on a quiet street with sloping hills & majestic, mature nature abutting the winding Pleasant River, this buildeable Lot just under 3 Acres, sits in the heart of the beloved Lakes Region and promises not only the wholesome peace & serenity

  Cristina Eugen Keller Williams Realty

  

  0 Cook, Windham, ME 04062
• 

  

  /2

  $235,000

  • Land
  • 1.84 Acres
  • $127,717 per Acre

  39 Cook Rd, Windham, ME 04062

  Rare opportunity to build your dream home/getaway destination or private sanctuary away from it all, yet with conveniences of daily living still nearby. Nestled on a quiet street with sloping hills & majestic, mature nature abutting the winding Pleasant River, this buildeable Lot just under 2 Acres, sits in the heart of the beloved Lakes Region and promises not only the wholesome peace & serenity

  Cristina Eugen Keller Williams Realty

  

  39 Cook Rd, Windham, ME 04062
• 

  

  

  /57

  $435,000

  • 1 Bed
  • 1 Bath
  • 632 Sq Ft

  12 Shore Rd, Windham, ME 04062

  Nestled along the peaceful shores of Pettingill Pond, 12 Shore Road in Windham, Maine has the perfect blend of classic lakeside charm and modern comfort. This inviting property boasts stunning water views, direct access to the pond, and a serene setting ideal for both year-round living and seasonal escapes. Inside, you'll find a bright and welcoming layout with large windows that fill the home

  Aaron Spiller Rockstar Real Estate

  

  12 Shore Rd, Windham, ME 04062
• 

  

  

  /30

  $585,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  70 Nash Rd, Windham, ME 04062

  This spacious three-bedroom plus an office Cape-style home offers an exceptional layout, highlighted by vaulted, beamed ceilings that bring warmth and character to the dining and living areas. The refreshed kitchen features painted cabinetry and new countertops, creating a clean and inviting space. The first floor includes an updated bathroom and a versatile bedroom, currently used as a playroom.

  

  Monica Dambach

  Waypoint Brokers Collective

  (207) 436-8796

  

  70 Nash Rd, Windham, ME 04062
• 

  

  /42

  $649,000

  • 2 Baths
  • 2,710 Sq Ft

  305 Gray Rd, Windham, ME 04062

  Gorgeous Duplex in Desirable Windham Offering Strong Rental Income! This well maintained property features long-term tenants and is perfectly suited for investors or owner-occupants looking to offset their mortgage. Rich in character, the home showcases beautiful exposed beams and warm wood features throughout, blending charm with functionality. Recent updates include a new roof, new back deck

  Jennifer Sumrall The Maine Real Estate Experience

  

  305 Gray Rd, Windham, ME 04062
• 

  

  /42

  $680,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  315 River Rd, Windham, ME 04062

  Welcome to 315 River Road in Windham, a well-maintained gambrel-style home offering space, flexibility, and privacy on 4.7 acres. This 3-bedroom, 3-bath home features a true primary suite along with recently updated bathrooms and hardwood flooring. Heat pumps provide efficient heating and cooling, and a whole-house generator offers added peace of mind year-round. The layout offers functional and

  Chris Gerrity Maine Real Estate Experts

  

  315 River Rd, Windham, ME 04062
• 

  

  /63

  $625,000

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  168 Cottage Rd, Windham, ME 04062

  Your Maine escape, just under two hours from Boston. Tucked onto a quiet lane with water access to Highland Lake, this fully renovated 3-bedroom, 1.5-bath retreat was made for long weekends, lazy summers, and leaf-peeping getaways without the maintenance headaches that usually come with a second home. Completely modernized from the studs out, the ~1,650 sqft interior offers a bright, open-concept

  

  Nicholas Dambrie

  Keller Williams Realty

  (207) 742-7180

  

  168 Cottage Rd, Windham, ME 04062
• 

  

  /26

  $289,900

  • 2 Beds
  • 2 Baths
  • 1,668 Sq Ft

  9 Settlers Ct, Windham, ME 04062

  Easy, low-maintenance living in Trailwood Village Condo Association. This 2-bedroom, 2-bath condo offers the ease of single-level living with a functional layout, dedicated laundry area, and additional basement storage to keep things organized. The association covers exterior maintenance, landscaping, and snow removal--making it a practical, low-stress option for those looking to simplify or

  Scott Townsend Keller Williams Realty

  

  9 Settlers Ct, Windham, ME 04062
• 

  

  /35

  $549,900

  • 3 Beds
  • 2 Baths
  • 1,915 Sq Ft

  516 Falmouth Rd, Windham, ME 04062

  Well-maintained and move-in ready, this bright and inviting home is set on a quiet, private lot just minutes from town. Tucked back from the road and surrounded by a natural tree buffer, it offers a great balance of privacy and convenience. Inside, you'll find an open-concept kitchen, living, and dining area, with oversized windows and a clean, updated feel throughout. The second floor features a

  Jonathan Cirrinone Maine Real Estate Experts

  

  516 Falmouth Rd, Windham, ME 04062
• 

  

  /46

  $619,900

  • 2 Baths
  • 2,252 Sq Ft

  41 Lotts Dr, Windham, ME 04062

  41 Lotts Dr, Windham, ME - Owner-Occupy Opportunity with Income Potential Open House Saturday, April 18th from 10:00 AM - 12:00 PM Live in one unit and let the other help pay your mortgage. This well-maintained 2-unit property offers a spacious 3-bedroom unit that will be delivered vacant at closing, paired with a 2-bedroom apartment currently leased to great tenants at $2,200/month. The

  Sarah Msuya Dream Home Realty LLC

  

  41 Lotts Dr, Windham, ME 04062
• 

  

  /57

  $765,000

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  19 Treasure Ln, Windham, ME 04062

  Well-maintained 4-bedroom, 2.5-bath home located on just under 2 acres in desirable Windham. Situated at the end of a private way and surrounded by trees, the property offers a quiet, natural setting with frequent wildlife sightings. Built in 2023, the home has been carefully maintained by the current owners and features tasteful finishes throughout.Offering a balance of rural living and

  Garret Getch EXP Realty

  

  19 Treasure Ln, Windham, ME 04062
• 

  

  /20

  $699,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  29 Daybreak Ln Unit 6, Windham, ME 04062

  Welcome to The Cove at Highland Lake! A first of its kind 55+ Lakefront Community nestled on the pristine shores of Highland Lake. 29 Daybreak is framed and weather tight making it perfect for mid-2026 delivery! The YORK floor plan offers true one level, low barrier living with unique split driveway layout. At 1280 SF +/-, this popular 2 Bedroom 2 Bathroom home is an excellent option for those

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  29 Daybreak Ln Unit 6, Windham, ME 04062
• 

  

  /53

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  74 Emerson Dr, Windham, ME 04062

  Welcome to 74 Emerson Drive in Windham, where peaceful pondside living meets everyday convenience. This charming 3-bedroom, 1.5-bath home offers beautiful views of Collins Pond from both the living room and the upstairs primary bedroom, creating a relaxing backdrop to your daily life. Start your mornings on the large east-facing deck overlooking the pond, where sunrises reflect across the water,

  Jason Elvin EXP Realty

  

  74 Emerson Dr, Windham, ME 04062
• 

  

  /35

  $284,000

  • 2 Beds
  • 1.5 Baths
  • 833 Sq Ft

  18 Cosmic Way Unit 18, Windham, ME 04062

  Welcome home to this bright and cheerful 2-bedroom, 1.5-bath townhouse-style condo--an ideal opportunity for first-time buyers looking for comfort, value, and convenience. Move right in and enjoy an updated kitchen with granite countertops and stainless steel appliances, along with fresh finishes throughout that make the space feel modern and inviting. The recently added first-floor half bath is

  Susan Sinnett RE/MAX Shoreline

  

  18 Cosmic Way Unit 18, Windham, ME 04062
• 

  

  /10

  $998,900

  • Land
  • 35 Acres
  • $28,540 per Acre

  0 Lakeside Dr, Windham, ME 04062

  Discover a rare opportunity to own approximately 35± acres of private, wooded land featuring natural stream corridors that flow toward Forest Lake, in one of Southern Maine's most desirable and rapidly growing areas. Ideally located between Windham, Falmouth, and Cumberland, this expansive parcel offers exceptional privacy while remaining just 15 minutes from Portland and minutes to I-95. Set

  Belinda Desmond Keller Williams Realty

  

  0 Lakeside Dr, Windham, ME 04062
• 

  

  /53

  $599,000

  • 6 Beds
  • 4 Baths
  • 2,940 Sq Ft

  96 Mineral Spring Rd, Windham, ME 04062

  Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property with Huge Potential or make it your home with an inlaw. Opportunity awaits. This unique property offers incredible potential for investors, contractors, or buyers looking to create value. Located just a short walk to association access on beautiful Sebago Lake, the property features multiple units and flexible living space with

  Jackie Griffeth Krainin Real Estate

  

  96 Mineral Spring Rd, Windham, ME 04062
• 

  

  /8

  $459,900

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  39 Pipeline Rd, Windham, ME 04062

  Well maintained classic Cape on a large lot. 1st floor consists of a nice kitchen area, large living room. 1 bedroom on 1st floor and a full bath for convenience. Second floor has 2 full sized bedrooms and a full bath. Hardwood floors. Great location. Seller willing to buy down the mortgage rate on this home. One Year American Home Shield Warranty included from Seller.

  William Mandell Cameron Prestige LLC

  

  39 Pipeline Rd, Windham, ME 04062
• 

  

  /17

  $172,500

  • Land
  • 1.17 Acres
  • $147,436 per Acre

  014-17-J01 Mimi Ln, Windham, ME 04062

  Tucked away on a quiet dead end road, this beautiful 1.17-acre parcel offers the perfect blend of privacy and convenience in the heart of Windham. With no association fees and situated on a private road, this is your opportunity to create the lifestyle you've been dreaming of, without the restrictions. Enjoy the peaceful setting while being just minutes from shopping, dining, and everyday

  Jennifer Sumrall The Maine Real Estate Experience

  

  014-17-J01 Mimi Ln, Windham, ME 04062
• 

  

  /30

  $950,000

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft

  103 Basin Rd, Windham, ME 04062

  This a great opportunity to own a classic lakeside home on the shores of the Sebago Lake Basin. Built in the 1930s and full of timeless character, this charming cottage style home sits right at the water's edge, offering beautiful views of the lake and Lyndsay Island just across the way. Set on a .31 acre lot, the property includes a shed structure and deck perched directly on the shoreline

  David Banks RE/MAX By The Bay

  

  103 Basin Rd, Windham, ME 04062
• 

  

  /35

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  36 Belvedere Dr, Windham, ME 04062

  Welcome to this beautifully maintained custom Colonial in the desirable Belvedere Estates, offering the feel of a nearly brand-new home with a bright, open-concept design perfect for modern living and entertaining. Gleaming hardwood floors run throughout the home, featuring a stunning kitchen with a large center island, granite countertops, and stainless steel appliances. The kitchen opens

  Megan McShane Redfin Corporation

  

  36 Belvedere Dr, Windham, ME 04062
• 

  

  /15

  $289,888

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  42 Main St, Windham, ME 04062

  Really nice opportunity to live in a spacious old home on the river with century old character and charm on over 3 acres. Conveniently located in the Little Falls area of South Windham. 'Good Bones' is what this house offers while there are a number of repairs needed inside and out. Unique property has not been offered to the market for 50+ years.

  Justin Douglass Albert Neal Real Estate Company

  

  42 Main St, Windham, ME 04062
• 

  

  /69

  $889,000

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  32 Pennywhistle Dr, Windham, ME 04062

  This stunning home is bathed in natural light and beautifully appointed. It was purchased 1 year ago as an unfinished new build 3 bed/1 bath home, that is now transformed into a light, bright 3 bedroom 3 bath (plumbed for a 4th bath in the unfinished high ceilinged daylight basement) with a new sunny primary suite, library, laundry and mudroom.Enter the front door to a 2 story foyer and

  John Hatcher Keller Williams Realty

  

  32 Pennywhistle Dr, Windham, ME 04062
• 

  

  /15

  $550,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  30 Marshall Valley Rd, Windham, ME 04062

  Build Your Dream Home With One Of Maines's Premier Builders!! Welcome To 30 Marshall Valley Road. This ''Similar To Be Built'' 1620 sqft.+/-, 3 bedroom,1.5 bath ranch with oversized 30'x24' 2 car garage is perfectly set on a private 2.11 acre+/- lot. Enjoy all of the luxury of a new build by being able to choose your own colors and amenities, flooring, countertops and kitchen design!! (See

  William Noone Getty Real Estate Services, LLC

  

  30 Marshall Valley Rd, Windham, ME 04062
• 

  

  /22

  $599,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  53 Johnson Rd, Windham, ME 04062

  New construction 3BR/2BA ranch with deeded Highland Lake access, offering the perfect combination of single-level living, modern efficiency, and outdoor lifestyle. Set on a private 1.26-acre wooded lot, this 1,400 sq ft home features an open-concept layout with kitchen island, pantry, and spacious living area. Property includes attached 2-car garage, full basement for storage or future expansion,

  Stephen Welsh Plowman Realty Group

  

  53 Johnson Rd, Windham, ME 04062
• 

  

  /56

  $1,150,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,350 Sq Ft

  17 Betty Ln, Windham, ME 04062

  Welcome to Edgewood Estates, one of Windham's most sought-after new communities, offering a rare opportunity to own within a thoughtfully designed six-lot setting surrounded by natural beauty. Positioned at the edge of the neighborhood, this home offers a sense of retreat, where protected conservation land becomes your backdrop and everyday living feels quietly elevated. Inside, light pours

  Andrea Page Keller Williams Realty

  

  17 Betty Ln, Windham, ME 04062
• 

  

  /43

  $1,060,000

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  594 River Rd, Windham, ME 04062

  This large, cherished property has been lovingly preserved by the same family for decades, dating back to its early use by the Girl Scouts for camping and swimming. Encompassing just over 28 acres, the land offers exceptional privacy and includes a rare island in the river where children once camped. One of the property's most distinctive features is the river flowing from Sebago Lake, known for

  Stephen Welsh Plowman Realty Group

  

  594 River Rd, Windham, ME 04062
• 

  

  /43

  $524,900

  • 2 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  1112 Roosevelt Trail Unit 8, Windham, ME 04062

  Rare Sebago Lakefront Property! Don't miss this rare opportunity to own a beachfront home on the shores of stunning Sebago Lake with approximately 300 feet of private, sandy shoreline. This exceptional property offers breathtaking sunsets and panoramic views of Sebago Lake and Mount Washington. The home offers an updated kitchen with brand-new stainless steel appliances, modern cabinets and solid

  Brian DuBois Keller Williams Realty

  

  1112 Roosevelt Trail Unit 8, Windham, ME 04062
• 

  

  /22

  $469,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  12 Dolley Farm Rd Unit 6, Windham, ME 04062

  Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Harvest style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining

  Marie Flaherty The Flaherty Group

  

  12 Dolley Farm Rd Unit 6, Windham, ME 04062
• 

  

  /22

  $545,000

  • 2 Baths
  • 1,408 Sq Ft

  324 Roosevelt Trail, Windham, ME 04062

  Great opportunity for contractor, Landscaper or investor. One could also live in one unit or rent both for income and create other opportunities with acreage and location. Currently 2 one bedroom apartments and an oversized garage. Lots of land for storage or expansion. Property is located in Farm Zone

  Michael Jacobson Kre Brokerage Group

  

  324 Roosevelt Trail, Windham, ME 04062
• 

  

  /19

  $349,900

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  7 Magnolia Ln Unit 2, Gardiner, ME 04345

  Welcome to Gardiner's newest condominiums! This architectural style has been meticulously restored, honoring its rich heritage while embracing contemporary living. You will enjoy its flowing layout with oversized windows that bathe the rooms with natural light. Premium finishes include gleaming wood floors, granite countertops, oversized closets, laundry room, and generous kitchen with abundant

  Geri Doyle Rizzo Mattson

  

  7 Magnolia Ln Unit 2, Gardiner, ME 04345
• 

  

  /31

  $424,900

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  10 Abby Rd, Windham, ME 04062

  ✨ Valuable Updates + Equity Potential = Smart Buy in Windham! MORE UPDATES! Not a new home -- but packed with brand-new updates where it counts! This move-in ready Cape features a new furnace, new kitchen, new bath, and beautifully refinished hardwood floors, giving you modern comfort without the renovation hassle. Want room to grow your value? The unfinished second floor offers built-in

  Patricia Gallant Dream Home Realty LLC

  

  10 Abby Rd, Windham, ME 04062
• 

  

  /13

  $665,000

  • 4 Beds
  • 2 Baths
  • 3,444 Sq Ft

  14 Emerson Dr, Windham, ME 04062

  Unique opportunity to own this 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage.Boasting a Single Family home with attached apartment and over 3,000 square feet of finished space the possibilities are endless. Property is currently occupied and being sold at auction site with no access. No Trespassing, do not disturb the occupants.

  Justin Robbins Excellence Realty

  

  14 Emerson Dr, Windham, ME 04062
• 

  /2

  $525,000

  • Land
  • 49.7 Acres
  • $10,563 per Acre

  Lot 4 Highland Cliff Rd, Windham, ME 04062

  Welcome To Lot 4 Highland Cliff Road. This Beautiful 49.7 +/- Acre Parcel Has A Lot Of Options. Located in Windham off of the very popular Highland Cliff Road, Property is partially through the subdivision process as Phase 2 of the Canada Hill Subdivision, but very developable as a new subdivision (Talk to the planning board), or even just a very private spacious single lot. There is also an

  William Noone Getty Real Estate Services, LLC

  

  Lot 4 Highland Cliff Rd, Windham, ME 04062
• 

  

  /29

  $499,000

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft

  18 Cook Rd, Windham, ME 04062

  Move in ready at its finest! Set on a private lot, in a great location, this home is ready for new owners. With an efficient layout, this home will be low maintenance for years to come. Schedule your showing today!

  Malachi Winslow Keller Williams Realty

  

  18 Cook Rd, Windham, ME 04062
• 

  

  /14

  $125,000

  • Land
  • 2.11 Acres
  • $59,242 per Acre

  30 Marshall Valley Rd, Windham, ME 04062

  Location, Location, Location!! Welcome to 30 Marshall Valley Road. This 2.11 Acre Lot has everything from privacy, and a country setting to a babbling brook in the back of the Lot. All perfectly Set off of Highland Cliff Road in Windham!! Build your dream home with one of Maine's premiere Builders. (See MLS #1633184 Residential for a similar to be built build package). Many designs and floorplans

  William Noone Getty Real Estate Services, LLC

  

  30 Marshall Valley Rd, Windham, ME 04062
• 

  

  /5

  $325,000

  • Land
  • 34,412 Sq Ft
  • $411,392 per Acre

  1042 Roosevelt Trail, Windham, ME 04062

  This .79 +/- acre lot has deeded rights to pass and repass on foot by the right of way from the County Road to Sebago Lake, and to pass and repass on foot along the shore of said Sebago Lake. The site offers an opportunity to build a spacious new home set back from the road along with an in-home business use and/or accessory apartment Alternatively, this site offers an opportunity to develop a

  Larry Eliason Butts Commercial Brokers

  

  1042 Roosevelt Trail, Windham, ME 04062
• 

  

  /51

  $735,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  1 Friendly Way (On Land of Nod ), Windham, ME 04062

  Welcome to 1 Friendly Way -- South Windham's newly built, luxury modern-style bungalow located on Land of Nod Road, a quiet street just five minutes from Highland Lake and approximately two miles from the public boat launch on the Falmouth side. This 2,016 sq. ft. floor plan offers a first-floor open concept layout with a gas fireplace and real oak hardwood flooring, along with a beautiful

  Sandra Reid Coldwell Banker Realty

  

  1 Friendly Way (On Land of Nod ), Windham, ME 04062
• 

  

  /3

  $429,000

  • Land
  • 3.7 Acres
  • $115,946 per Acre

  99 Enterprise Dr, Windham, ME 04062

  The parcel has water stubbed at the road and a gravel curb cut already installed. Ideal location for manufacturing, private warehousing and high bay boat storage.

  Larry Eliason Butts Commercial Brokers

  

  99 Enterprise Dr, Windham, ME 04062
• 

  

  /11

  $1,995,000

  • Land
  • 5.91 Acres
  • $337,563 per Acre

  0 Turning Leaf Dr Unit 1640377, Windham, ME 04062

  •Approved State and Town for a 9,018± SF commercial building, including DEP, DOT, and Portland Water District•DEP & DOT permits approved in 2023 for the 2 building concept•Commercial District 1 Zoning suitable for a variety of uses•Rare parcel of land in one of Maine's fastest growing communities•Easy access to I-95 and other major corridors•Growing community with strong

  Michael Anderson Malone Commercial Brokers, Inc.

  

  0 Turning Leaf Dr Unit 1640377, Windham, ME 04062

Showing Results 1 - 40, Page 1 of 2