Homes for Sale near Windham High School

• 

  

  

  /12

  $699,000

  Open Tue 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  25 Daybreak Ln Unit 8, Windham, ME 04062

  Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 25 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes provide both first and second floor primary suite options. Multi-generational, Companion, and Guest-Friendly, owners of these units can opt

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  25 Daybreak Ln Unit 8, Windham, ME 04062
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /74

  $1,600,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,024 Sq Ft

  36 Whittemore Cove Rd, Raymond, ME 04071

  Enjoy exceptional waterfront living on Big Sebago Lake from this beautifully updated property set on 1.75 acres in a protected cove with 90 feet of sandy, gradual-entry frontage--ideal for swimming, boating, and relaxing at the shoreline. The property includes a modular dock system with jet ski lift, making lake access easy and convenient all season long. This furnished 4-bedroom, 3.5-bathroom

  Jackie Griffeth Krainin Real Estate

  

  36 Whittemore Cove Rd, Raymond, ME 04071
• 

  

  

  /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
• 

  

  

  /27

  $458,000

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft

  1 Melrose Way Unit 42, Windham, ME 04062

  Set within the desirable Corner Brook II Condo Association, this rare three-bedroom, two-bathroom condo offers the ease of single-level living paired with the flexibility and space so many buyers are searching for. As a row-end unit located within a cul-de-sac setting, the home enjoys an added sense of privacy while still being close to Windham's everyday conveniences, outdoor recreation, and

  Scott Townsend Keller Williams Realty

  

  1 Melrose Way Unit 42, Windham, ME 04062
• 

  

  

  /81

  $599,000

  • 3 Beds
  • 2 Baths
  • 3,196 Sq Ft

  18 Martin Heights, Raymond, ME 04071

  Meticulously updated home nestled on a beautiful lot in the highly sought-after Martin Heights community. This property offers peace of mind with extensive recent improvements, including a new metal roof (2025), new well water system (2025), replaced radon air fan (2025), and generator hookup. Additional upgrades include mini split system, jet pump, air well, and a water softening system with ion

  Libby Brackett Real Broker

  

  18 Martin Heights, Raymond, ME 04071
• 

  

  /21

  $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
• 

  

  /37

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft

  6 Outlaw Ridge Rd, Raymond, ME 04071

  Welcome to 6 Outlaw Ridge Rd! Conveniently located just minutes from New Gloucester, Poland, Windham, and Gray, this 3 bedroom, 1 bath home offers a great opportunity to add your personal style and build equity. Situated on 2.17 acres, the property features a peaceful natural setting with a small private pond, patio area, and room to enjoy the outdoors. Inside, you'll find additional partially

  Jennifer Sumrall The Maine Real Estate Experience

  

  6 Outlaw Ridge Rd, Raymond, ME 04071
• 

  

  /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
• 

  

  /40

  $460,000

  • 3 Beds
  • 1 Bath
  • 1,536 Sq Ft

  265 Windham Center Rd, Windham, ME 04062

  This 3-bedroom, 1 bathroom home features many recent updates, including a newer furnace, roof, vinyl siding, windows, decks, and appliances--giving peace of mind and modern convenience. Enjoy the outdoors from the updated decks overlooking Black Brook, perfect for relaxing and taking in the natural surroundings.Located across the street from Black Brook Preserve, featuring over 100 acres of

  Nancy Rousselle Coldwell Banker Realty

  

  265 Windham Center 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
• 

  

  /42

  $639,000

  $10K PRICE DROP

  • 2 Baths
  • 2,710 Sq Ft

  305 Gray Rd, Windham, ME 04062

  Gorgeous Duplex in Windham Offering Strong Rental Income! This well maintained property features long-term tenants. 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 and stairs, and an oversized shed that conveys with the property for additional storage, currently

  Jennifer Sumrall The Maine Real Estate Experience

  

  305 Gray Rd, Windham, ME 04062
• 

  

  /14

  $125,000

  $75K PRICE DROP

  • 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
• 

  /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 near the Pleasant River, with sloping hills, mature trees & majestic natural beauty as far as the eye can see, this buildeable Lot of just under 3 Acres, sits in the heart of Town and promises not only the wholesome

  Cristina Eugen Keller Williams Realty

  

  39 Cook Rd, Windham, ME 04062
• 

  

  /21

  $365,000

  • 2 Beds
  • 1 Bath
  • 878 Sq Ft

  402 Roosevelt Trail, Windham, ME 04062

  402 Roosevelt Trail offers the perfect blend of recent updates, convenience, and space to enjoy Maine living. Situated on a generous 1.42-acre lot, this property features a spacious, fully fenced backyard--ideal for entertaining, pets, or simply relaxing in your own private outdoor setting.Significant improvements completed by the previous owner in 2024 include a new roof, new leach field,

  Amato Polselli Benchmark Real Estate

  

  402 Roosevelt Trail, Windham, ME 04062
• 

  

  /28

  $399,900

  $35K PRICE DROP

  • 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
• 

  

  /52

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft

  68 Provost Dr Unit 13, Windham, ME 04062

  This North Windham Ranch Condo is beautifully maintained, and move-in-ready. It offers a blend of natural tranquility and modern convenience.From the open fields to the wooded backyard, nature is all around you. The covered wrap deck is a welcome place to sit and relax or sip your morning coffee while listening to the birds chirping.As you enter the inside of the home, the open-concept

  Amber The Collective Real Estate Co

  

  68 Provost Dr Unit 13, Windham, ME 04062
• 

  

  /44

  $599,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,717 Sq Ft

  18 Haven Rd, Windham, ME 04062

  Brand-new construction on a quiet dead-end Windham road, offering modern comfort and an easy commute to Portland and Highland Lake. This 3 bedroom, 2 bath home features quality finishes, efficient systems, and a bright, open layout designed for today's lifestyle. Enjoy the privacy of a peaceful setting while staying close to shopping, dining, and major routes. A great opportunity to own new

  Matt Wright Maine Real Estate Experts

  

  18 Haven Rd, Windham, ME 04062
• 

  

  /27

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 1,216 Sq Ft

  1112 Roosevelt Trail Unit 16, Windham, ME 04062

  Some properties sell a house. This one sells a lifestyle. Set on the shores of Sebago Lake with your own boat mooring, sandy beach access, and sweeping views of the water and mountains beyond, this condominium offers four seasons of the good life -- boating and swimming in summer, ice fishing and snowshoeing in winter, and quiet lakefront mornings year-round. Inside, hardwood floors and lake

  David Banks RE/MAX By The Bay

  

  1112 Roosevelt Trail Unit 16, Windham, ME 04062
• 

  

  /20

  $669,000

  Open Tue 11AM - 1PM $30K PRICE DROP

  • 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
• 

  

  /50

  $4,950,000

  • 5 Beds
  • 6.5 Baths
  • 6,022 Sq Ft

  46 Windward Shore Rd, Raymond, ME 04071

  SEBAGO LAKE - Discover this exceptional 1.8-acre estate offering breathtaking westerly views, stunning sunsets, and unmatched privacy. This shingle-style home combines impeccable quality with thoughtful design, perfect for comfortable year round lake living and entertaining. Outside, enjoy 260' of lake frontage, a deepwater dock, concrete boat launch, lakeside BBQ, rolling lawn, and a gentle

  Sandra Wendland Legacy Properties Sotheby's International Realty

  

  46 Windward Shore Rd, Raymond, ME 04071
• 

  

  /17

  $619,000

  Open Tue 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 1,958 Sq Ft

  14 Daybreak Ln Unit 15, Windham, ME 04062

  Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. The PORTLAND is the perfect blend of one-level-living meets plenty of room for guests and storage. At 1958 SF +/-, this 2 Bedroom 2.5 Bathroom attached condo with generous finished basement is an excellent option for those looking to ''rightsize'' into

  Crystal Chandonnet Berkshire Hathaway HomeServices Verani Realty

  

  14 Daybreak Ln Unit 15, 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
• 

  

  /50

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,787 Sq Ft

  41 Haskell Ave, Raymond, ME 04071

  OPEN HOUSE ON FRIDAY 5/15 1pm-4pm. In the heart of the Sebago Lake Region, at the shores of beautiful Crescent Lake in Raymond, rests this charming, cottage-style, custom-built, waterfront home. Year round living... or rent it out, as this prime vacation spot can also be a Great TURNKEY Opportunity!! The 1,787sf, includes 3 bedrooms, 2 baths, main floor laundry, office, exercise room, and a

  Jeffrey Perron Pine Tree Realty of Maine

  

  41 Haskell Ave, Raymond, ME 04071
• 

  /2

  $479,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  26 Dolley Farm Rd Unit 12, 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 Sunrise 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

  

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

  

  /19

  $299,000

  $76K PRICE DROP

  • 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
• 

  

  /57

  $619,000

  $6K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,209 Sq Ft

  64 Pope Rd, Windham, ME 04062

  Set on a private 2.23 acre lot and tucked back from the road, this spacious 5 Bedroom 2 bath multi-level home is freshly updated and move in ready. The upper level features a mudroom entry, four large bedrooms and a full bath. Walk down the stairs to the lower level which has a new kitchen, family room, living/dining area, second full bath, fifth bedroom or home office, and laundry room. Step

  Elizabeth Marks The Real Estate Store

  

  64 Pope Rd, Windham, ME 04062

Showing Results 41 - 67, Page 2 of 2