42

Windham, ME Homes for Sale under $500,000

Section Image Section Image
  • /30

    $495,000

    • 1 Bed
    • 1 Bath
    • 544 Sq Ft

    12 Gate Way, Windham, ME 04062

    If you've been searching for a true, easy-living Maine camp feel with modern comfort, you've found it!12 Getaway Road in Windham checks every box. Nestled right on the quiet Little Duck Pond, this charming, updated cottage offers peaceful waterfront living with the unbeatable convenience of an easy-access Windham location.Inside, the fresh space centers around the amazing views

    Agent Photo

    Patricia Gallant

    Dream Home Realty LLC

    12 Gate Way, Windham, ME 04062
  • /2

    $350,000

    • Land
    • 20,473 Sq Ft
    • $744,681 per Acre

    2 Vintage Dr, Windham, ME 04062

    This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 1 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

    Agent Photo

    Michael Jacobson

    Kre Brokerage Group

    2 Vintage Dr, Windham, ME 04062
  • /82

    $499,900

    • 2 Beds
    • 2 Baths
    • 1,255 Sq Ft

    22 Montgomery Rd, Windham, ME 04062

    A year-round brook, your own private waterfalls, and a true Maine homestead on over 2 magical acres -- just 30 minutes to Portland.Some properties you tour. This one you fall for. Set on over two private acres along year-round Colley Wright Brook -- with over 300 feet of owned water frontage and your very own waterfalls -- this is the rare retreat where the land itself tells the story. Gather

    Agent Photo

    Jennifer Whitehead

    Dream Home Realty LLC

    22 Montgomery Rd, Windham, ME 04062
  • /2

    $450,000

    • Land
    • 29,185 Sq Ft
    • $671,642 per Acre

    1 Derringer Dr, Windham, ME 04062

    This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 2 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

    Agent Photo

    Michael Jacobson

    Kre Brokerage Group

    1 Derringer Dr, Windham, ME 04062
  • /55

    $415,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,466 Sq Ft

    409 Pope Rd, Windham, ME 04062

    Move right into this beautifully remodeled home offering the perfect combination of modern updates, comfortable living space, and a convenient location just minutes from shopping, dining, everyday amenities, and Maine's beautiful Lakes Region. Whether you're searching for extra space, room to entertain, or a home that's ready to enjoy from day one, this property has so much to offer.Featuring

    Bill Bergeron Fontaine Family-The Real Estate Leader

    409 Pope Rd, Windham, ME 04062
  • /52

    $299,000

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

    7 Magnolia Ln Unit 2, Gardiner, ME 04345

    Welcome to one of Gardiner's established condominium communities, where historic character and modern living come together beautifully. This thoughtfully restored architectural style honors the building's rich heritage while offering the comfort and convenience of contemporary living. The flowing layout features oversized windows that fill the rooms with natural light, with generously sized rooms

    Clayton Larochelle Fontaine Family-The Real Estate Leader

    7 Magnolia Ln Unit 2, Gardiner, ME 04345
  • /27

    $479,000

    $5K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    6 Dolley Farm Rd Unit 3, Windham, ME 04062

    New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. 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

    Marie Flaherty The Flaherty Group

    6 Dolley Farm Rd Unit 3, Windham, ME 04062
  • /24

    $450,000

    $59K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,135 Sq Ft

    14 Family Cir Unit 2, Windham, ME 04062

    Don't miss this opportunity to own a year-round, two-bedroom cottage on beautiful Sebago Lake! Located in a five-member association, this property includes its own deep-water boat slip, making it ideal for boating enthusiasts.The renovation has already begun, as shown in the photos, giving the next owner a head start on creating their perfect lakeside retreat. The seller has decided to

    Ronald Cote Real Estate 2000 ME/NH

    14 Family Cir Unit 2, Windham, ME 04062
  • /56

    $485,000

    • 3 Beds
    • 2 Baths
    • 2,332 Sq Ft

    129 Forbes Ln, Windham, ME 04062

    Welcome to 129 Forbes Lane! Set on nearly half an acre in an established Windham neighborhood, this classic and alluring Cape offers 3 second level bedrooms, and a 1st floor bonus room which was designed as a primary bedroom! 2 full bathrooms that have been recently renovated, and approximately 1,888 square feet of living space. A full bathroom on both the first and second levels provides added

    Joel Turgo Elevate Maine Realty

    129 Forbes Ln, Windham, ME 04062
  • /15

    $279,900

    $39K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,092 Sq Ft

    42 Main St, Windham, ME 04062

    Spacious old home on the river with century old character and charm on a large private lot. Conveniently located in the Little Falls area of South Windham. Unique property has not been offered to the market for 50+ years. Great bones, good candidate for sweat equity or a flip.

    Justin Douglass Albert Neal Real Estate Company

    42 Main St, Windham, ME 04062
  • /10

    $475,000

    • 3 Beds
    • 1 Bath
    • 1,215 Sq Ft

    439 Falmouth Rd, Windham, ME 04062

    Enjoy the best of both worlds with this charming 3-bedroom ranch featuring a 1-car garage, nestled in a peaceful rural setting in Windham while remaining just minutes from shopping, restaurants, and local businesses.The open-concept layout offers a spacious feel, highlighted by hardwood floors and a large front-to-back living room that's perfect for relaxing or entertaining. The primary

    Amanda Salovitch Dream Home Realty LLC

    439 Falmouth Rd, Windham, ME 04062
  • /66

    $469,900

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,444 Sq Ft

    14 Emerson Dr, Windham, ME 04062

    Your Maine waterfront opportunity is knocking. This 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage was just pulled from Auction and has been reduced. Boasting a Single Family home with attached apartment and over 3,000 square feet of previous finished space the possibilities are endless. Images in this listing have been virtually staged.

    Justin Robbins Excellence Realty

    14 Emerson Dr, Windham, ME 04062
  • /33

    $479,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    65 High St, Windham, ME 04062

    Tucked in South Windham, an area experiencing exciting momentum as part of the town's ongoing Little Falls/South Windham Villages revitalization plan, this classic 1900 New Englander has been freshly painted from top to bottom and is ready to welcome its next chapter. Wood floors carry you through a sun-filled first floor, where the kitchen, dining room, and living room flow together with ease --

    Tim Flaherty The Flaherty Group

    65 High St, Windham, ME 04062
  • /12

    $299,900

    Open Wed 5PM - 7PM
    • 1 Bed
    • 1 Bath
    • 766 Sq Ft

    12 Stillwater Dr Unit 1137, Windham, ME 04062

    **Builder Incentives Available**.Stop paying rent! Own for $2100 per month*! The Highland offers a peaceful retreat designed for simple, modern living. With 766 square feet of thoughtfully designed space, this one-bedroom, one-bathroom residence blends comfort, style, and convenience in a layout that feels both open and inviting. Inside, contemporary finishes meet everyday functionality with

    Amy Foley Signature Homes Real Estate Group, LLC

    12 Stillwater Dr Unit 1137, Windham, ME 04062
  • /3

    $399,900

    $29K PRICE DROP
    • Land
    • 3.7 Acres
    • $108,081 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
  • /30

    $349,900

    Open Wed 5PM - 7PM
    • 2 Beds
    • 2 Baths
    • 991 Sq Ft

    10 Stillwater Dr Unit 3133, Windham, ME 04092

    *BUILDER INCENTIVES AVAILABLE* Own for $2400 per month*! This third floor unit features 9' ceilings and offers 991 square feet of bright, open-concept living. This thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll

    Amy Foley Signature Homes Real Estate Group, LLC

    10 Stillwater Dr Unit 3133, Windham, ME 04092
  • /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 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

    0 Cook, Windham, ME 04062
  • /63

    $415,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft

    25 Abby Rd, Windham, ME 04062

    Located in one of Windham Center's established neighborhoods, this 4-bedroom, 2-bath Cape offers comfortable living in a location that's hard to beat. The classic floor plan includes a convenient breezeway connecting the home to the attached two-car garage, while the private 0.35-acre lot provides space to relax, garden, or entertain outdoors.Enjoy being just minutes from North Windham's

    Rodney Charest Meservier & Associates

    25 Abby Rd, Windham, ME 04062
  • /53

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,880 Sq Ft

    54 Provost Dr Unit 54, Windham, ME 04062

    Welcome Home! This meticulously maintained townhouse offers an open floor plan with numerous amenities and upgrades including a freshly painted interior, custom design kitchen with granite counter tops and stainless appliances. Plus recently added modern comforts like the high efficiency heat pumps for climate control and a standby generator hook up. The high ceilings and large windows flood the

    Teri Ouellette Keller Williams Realty

    54 Provost Dr Unit 54, Windham, ME 04062
  • /26

    $335,000

    Open Wed 5PM - 7PM
    • 2 Beds
    • 2 Baths
    • 991 Sq Ft

    10 Stillwater Dr Unit 2129, Windham, ME 04092

    Take advantage of this limited time 'Fall Special' at $335,000 (regularly $349,900) for one unit only PLUS Builder Incentives Available. Stop paying rent! Own for $2400 per month*! Offering 991 square feet of bright, open-concept living, this thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private

    Amy Foley Signature Homes Real Estate Group, LLC

    10 Stillwater Dr Unit 2129, Windham, ME 04092
  • /29

    $489,000

    $36K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,560 Sq Ft

    1 Marzilli Way, Windham, ME 04062

    Full of classic New England charm, this 3-bedroom home offers generous living space and a flexible floor plan on a .46 acre corner lot. The updated kitchen features a large center island, new appliances, ample cabinet space, and an inviting layout for everyday living. Original hardwood floors, fireplaces, built-ins, exposed beams, and other period details add warmth and character throughout.

    David Banks RE/MAX By The Bay

    1 Marzilli Way, Windham, ME 04062
  • /30

    $329,900

    $19K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    549 Roosevelt Trail, Windham, ME 04062

    Brand New Price! Investor, builder, developers, home buyers! Whu buy a condo? Exceptional opportunity on highly popular Roosevelt Trail with flexible Residential (RM) zoning, offering potential for limited business use, a home occupation, or multi-unit development. This neat, clean, and sun-drenched property sits on a spacious 0.56-acre lot with 137 feet of prime road frontage. An asset for

    Todd Harvey Pine Tree Realty of Maine

    549 Roosevelt Trail, Windham, ME 04062
  • /40

    $450,000

    • 2 Beds
    • 2 Baths
    • 1,356 Sq Ft

    4 Misty Dr, Gray, ME 04039

    Fresh air, scenic surroundings, and a privately positioned property, paired with easy access to life's conveniences. This cute, structurally solid 2-bedroom, 2-bath ranch is a creative canvas primed for a present-day glow-up! Cozy character & nature views abound inside. You'll adore chatting while cooking in the kitchen & dining area. Seamlessly situated with a lofty ceiling and abundant natural

    Bridget King Jason Miller King + Miller Real Estate

    4 Misty Dr, Gray, ME 04039
  • /40

    $339,900

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,088 Sq Ft

    23 Meagans Way Unit 12, Windham, ME 04062

    Welcome to Windham Hill Woods, a well-established and desirable condominium community offering an exceptional combination of convenience, amenities and value. Ideally located on the south side of downtown Windham, this townhouse-style condo provides easy access to shopping, dining and area amenities while helping you avoid much of the traffic congestion found farther north. Inside, the

    Peter Mason PO-GO REALTY

    23 Meagans Way Unit 12, Windham, ME 04062
  • /58

    $385,000

    $50K PRICE DROP
    • 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

    Aaron Spiller Rockstar Real Estate

    12 Shore Rd, Windham, ME 04062
  • /13

    $275,000

    • Land
    • 6,098 Sq Ft
    • $1,964,286 per Acre

    58 Lower Beach Rd, Windham, ME 04062

    Imagine building the home you've always wanted just steps from Highland Lake.Tucked into Windham's sought-after Highland Lake community, 58 Lower Beach Road offers a rare opportunity to create something entirely your own in a setting where lake life becomes part of everyday life. Located just one lot back from the water with points of access to Highland Lake, this is your chance to build

    Andrea Page Keller Williams Realty

    58 Lower Beach Rd, Windham, ME 04062
  • /6

    $225,000

    • Land
    • 22,215 Sq Ft
    • $441,176 per Acre

    227 Tandberg Trail, Windham, ME 04062

    Discover a great opportunity to own land in a convenient Windham location, just minutes from the town center, shopping, dining, and local amenities.

    Jayden Gaudreau American Real Estate

    227 Tandberg Trail, Windham, ME 04062
  • /5

    $299,900

    $25K PRICE DROP
    • Land
    • 34,412 Sq Ft
    • $379,620 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 apartmentAlternatively, this site offers an opportunity

    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
  • /32

    $294,000

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,250 Sq Ft

    26 Whites Bridge Rd, Windham, ME 04062

    Welcome to this beautifully maintained and inviting two-bedroom condo, ideally located in the heart of Windham. Enjoy the convenience of being just minutes from shopping, restaurants, and everyday amenities while tucked away in a peaceful setting.The first floor features an open-concept layout with a spacious living room, kitchen, and dining area--perfect for both everyday living and

    Tiffany Libby Pamela Starnes Signature Homes Real Estate Group

    26 Whites Bridge Rd, Windham, ME 04062
  • /31

    $389,000

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft

    229 Tandberg Trail, Windham, ME 04062

    Welcome to 229 Tandberg Trail, where comfort, convenience, and opportunity come together in Maine's beautiful Lakes Region. This inviting ranch-style home offers easy one-level living in a desirable neighborhood, just minutes from shopping, restaurants, schools, lakes, parks, walking trails, and other everyday conveniences. Inside, you'll be greeted by a spacious open-concept living room, dining

    Daniel McLellan Plowman Realty Group

    229 Tandberg Trail, Windham, ME 04062
  • /64

    $349,900

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,357 Sq Ft

    15 Orchard Rd, Windham, ME 04062

    Highland Lake doesn't close for the winter. Swim and paddle in July, skate and ice fish in January! At 15 Orchard Rd the lake is yours by deeded right, a short walk down the road. No launch fees, no hunting for parking, no waterfront tax bill. Just a towel, or a sled, and five minutes. The property was originally three lots, so there's room here most homes in this neighborhood don't have —

    Jennifer Whitehead Dream Home Realty LLC

    15 Orchard Rd, Windham, ME 04062
  • /36

    $460,000

    • 3 Beds
    • 1.5 Baths
    • 1,395 Sq Ft

    8 Port Dr, Windham, ME 04062

    Welcome to 8 Port Drive, Unit 8, a well-maintained Windham condo offering a comfortable layout, thoughtful updates, and access to Collins Pond. Tucked into a quiet, secluded setting with little traffic, this home provides a peaceful atmosphere while keeping you close to the shops, restaurants, and conveniences of downtown North Windham. The main level offers the ease of single-floor living, with

    Brandon Robbins Samantha Mckague Real Broker

    8 Port Dr, Windham, ME 04062
  • /40

    $459,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,426 Sq Ft

    14 Voyager Ln Unit 14, Windham, ME 04062

    Move in ready, three years young, 3 bed 2.5 bath home with beautiful kitchen, large deck with nice yard in an incredible convenient location. This home is spotless and freshly painted. Just six units total in the entire association so you get all the upside of condo living without that big association feel.

    Richard Yost NextHome NorthEast Realty

    14 Voyager Ln Unit 14, Windham, ME 04062
  • /14

    $445,000

    $50K PRICE DROP
    • Land
    • 9.4 Acres
    • $47,340 per Acre

    0 Tavern Hill, Windham, ME 04062

    Large 9.4 +/-acre tract with 908' frontage meets the dimensional standards for up to four lots, each requiring minimum 200' frontage and 1.84 acres.Great opportunity for a home builder to construct several homes or a buyer to build his/her home and split off the remainder for multiple lots.Tavern Hill is a private road with a homeowners association.A nearly six acre lot

    Michael Rogers EXP Realty

    0 Tavern Hill, Windham, ME 04062
  • /20

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,088 Sq Ft

    24 Turkey Trail Unit 26, Windham, ME 04062

    Welcome to Windham Hill Woods, one of Windham's most desirable associations. Complete with underground pool, pickleball court, basketball court, playground, gazebo, community garden and sprawling open spaces for pets and recreation. This 2 bedroom, 1.5 bathroom townhouse is bright, warm, and offers bonus spaces to use as you wish. Equipped with a full unfinished basement and a great back deck and

    Lauren Kane Portside Real Estate Group

    24 Turkey Trail Unit 26, Windham, ME 04062
  • /33

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,642 Sq Ft

    12 Birchwood Ave, Windham, ME 04062

    Robert Norton Century 21 North East

    12 Birchwood Ave, Windham, ME 04062
  • /35

    $499,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,731 Sq Ft

    29 Lake Ave, Windham, ME 04062

    Offered for the first time in over 30 years, this charming 3 bedroom, 1 bathroom home with 1,331 square feet of living space sits on a private 0.41 acre lot tucked away on a quiet dead end road. Surrounded by mature greenery, fruit trees, and flowering shrubs, the setting provides a peaceful retreat with classic curb appeal highlighted by a red cedar shake exterior and a circular style paved

    Austin Hanthorn Redfin Corporation

    29 Lake Ave, Windham, ME 04062
  • /2

    $484,000

    New Construction $5K PRICE INCREASE
    • 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
  • /49

    $325,000

    • 1 Bed
    • 1 Bath
    • 644 Sq Ft

    8 Pettingill Rd, Windham, ME 04062

    Great little cottage in a fantastic location! In the heart of the lakes region in Windham with views and a ROW to Pettingill Pond, across 302 from The Deckhouse Restaurant and Seacoast Adventure and just a 3 minute drive to Richardsons boat yard in Standish. A 20 minute commute to Portland and a 6 minute drive to the Raymond boat launch on Sebago Lake make this the ultimate home base for all

    Rebecca LaBrie Meservier & Associates

    8 Pettingill Rd, Windham, ME 04062

Showing Results 1 - 40, Page 1 of 2

Home Price Trends

Median Sale Price
$518,700
Median Single Family Sale Price
$552,000
Median 2 Bedroom Sale Price
$397,500
Median 1 Bedroom Sale Price
$362,000
Average Price Per Sq Ft
$332
Number of Homes for Sale
73
Last 12 months Home Sales
276
Months of Supply
3.20
Median List Price
$540,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home