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New Gloucester, ME Homes for Sale with Acreage

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  • /59

    $1,050,000

    • 5 Beds
    • 3 Baths
    • 3,682 Sq Ft

    144 Orchard Rd, Cumberland Center, ME 04021

    A Rare Blend of Space, Privacy & Flexibility in CumberlandSet on 3.25 private acres in Cumberland's picturesque countryside, this stately Colonial offers 4,802± sq ft of finished living space—3,682± above grade and 1,120± in the partially finished basement. With 5 bedrooms and 4 full baths, including a flexible first-floor bedroom option and a full in-law apartment, the layout is ideal

    Agent Photo

    Nicholas Dambrie

    Keller Williams Realty

    (207) 687-1130

    144 Orchard Rd, Cumberland Center, ME 04021
  • /32

    $1,499,000

    • 5 Beds
    • 4.5 Baths
    • 4,621 Sq Ft

    239 Hunter Way, Falmouth, ME 04105

    Bold, stylish design, soaring ceilings with front-to-back sunshine, and an impressive amount of space for family, guests, or generational living define this fully renovated home, nestled on a private 2.92-acre lot in the highly desirable town of Falmouth. Boasting over 4,000 square feet of elegantly finished living space, this residence features 5 bedrooms and 4.5 bathrooms—perfectly blending

    Agent Photo

    David Banks

    RE/MAX By The Bay

    (207) 803-5365

    239 Hunter Way, Falmouth, ME 04105
  • /37

    $1,700,000

    • 4 Beds
    • 3.5 Baths
    • 3,836 Sq Ft

    30 Peaceful Way, Cumberland, ME 04021

    Clean lines, natural textures, and elevated finishes give this home its unmistakable sense of clarity and calm. Modern in feel, but grounded in comfort and designed for real life. Designed and built by Brush & Hammer Builders, the home flows seamlessly across three levels. A generous walk-in pantry sits just off the open kitchen, while the living and dining areas feel connected yet serene,

    Agent Photo

    David Banks

    RE/MAX By The Bay

    (207) 250-5664

    30 Peaceful Way, Cumberland, ME 04021
  • /59

    $1,050,000

    • 4 Baths
    • 3,682 Sq Ft

    144 Orchard Rd Unit 1, Cumberland Center, ME 04021

    A Rare Blend of Space, Privacy & Flexibility in CumberlandSet on 3.25 private acres in Cumberland's picturesque countryside, this stately Colonial offers 4,802± sq ft of finished living space—3,682± above grade and 1,120± in the partially finished basement. With 5 bedrooms and 4 full baths, including a flexible first-floor bedroom option and a full in-law apartment, the layout is ideal

    Agent Photo

    Nicholas Dambrie

    Keller Williams Realty

    (207) 747-0037

    144 Orchard Rd Unit 1, Cumberland Center, ME 04021
  • /78

    $899,000

    • 4 Beds
    • 5 Baths
    • 3,496 Sq Ft

    20 Motorcycle Dr, Windham, ME 04062

    Welcome to 20 Motorcycle Drive—an exceptional custom colonial farmhouse nestled on 7.6 private acres at the end of a quiet dead-end road. This 4-bedroom, 3-bathroom home offers 3496 square feet above grade and 1120 below grade of thoughtfully designed living space, perfect for those seeking comfort, functionality, and a peaceful rural lifestyle. Inside, you'll find a spacious layout featuring a

    Agent Photo

    Nicholas Dambrie

    Keller Williams Realty

    (207) 606-7264

    20 Motorcycle Dr, Windham, ME 04062
  • /59

    $1,299,000 Open Sun 3PM - 5PM

    • 4 Beds
    • 2.5 Baths
    • 3,702 Sq Ft

    72 Lakeside Dr, Falmouth, ME 04105

    Welcome to ''The Slip'' — a rare blend of privacy, personality, and prized lake access in Falmouth.Tucked at the end of a long, private driveway and surrounded by over 4 acres of peaceful woods, this classic Colonial delivers a lifestyle many dream of — and few find. Inside, you'll discover 4 spacious bedrooms, 2 living rooms, and a light-filled bonus room above the garage ideal for an

    Christopher Davis Real Broker

    72 Lakeside Dr, Falmouth, ME 04105
  • /53

    $1,300,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 5,068 Sq Ft

    148 Hunter Way, Falmouth, ME 04105

    OPEN HOUSE Sunday 6/29 from 12:00p-2:00p. This impressive Colonial style home is situated on 2.49 private acres in the established Fox Run neighborhood. This home has been meticulously maintained and combines classic design with modern amenities. Some of the special features include: oversized windows, spacious rooms, 9 ft. ceilings, gleaming oak floors, and a flexible floor plan. On the

    Casey Hooper Blue Lobster Real Estate

    148 Hunter Way, Falmouth, ME 04105
  • /73

    $1,095,000

    • 4 Beds
    • 2.5 Baths
    • 4,520 Sq Ft

    11 Oxford Rd, Windham, ME 04062

    Located on the most private lot in Windemere, this is more than just privacy - it's access to Sebago Lake, privacy, and luxury all in one. Enjoy shared access to one of Maine's most sought-after lakes. This stunning property includes access to Sebago Lake with three sections of private beaches exclusively for residents. You can moor your boat or join the waitlist for a dock space.Tucked away on

    Bailey Pate Maine Real Estate Co

    11 Oxford Rd, Windham, ME 04062
  • /74

    $1,099,000

    • 3 Beds
    • 3.5 Baths
    • 4,568 Sq Ft

    16 Gin Mill Ln, Windham, ME 04062

    Endless possibilities to tailor the layout to your needs! The seller is offering a custom home package through their company, White Dog Building, to help bring your vision to life at this serene and beautiful Mill Pond setting! Enjoy year-round stillness and tranquility on 2.5 acres with 285ft of owned water frontage, ideal for a dock and swimming, with additional access to an association beach

    Stacy Salvo Portside Real Estate Group

    16 Gin Mill Ln, Windham, ME 04062
  • /20

    $994,999

    • 3 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    12 Summit Terrace, Falmouth, ME 04105

    Large three bedroom & 2.5 baths house in West Falmouth sitting on a 1.53 acre quite dead end with a lot of new renovations. This beautiful home is spacious with a lot of natural light that flows in almost every room. Open concept updated kitchen with a large island with a dining area that goes out directly to the newly painted back deck overlooking the pool and backyard. Bonus room above the

    Sarem Al-Shawk Maine Real Estate Co

    12 Summit Terrace, Falmouth, ME 04105
  • /126

    $1,388,000

    • 6 Beds
    • 4 Baths
    • 3,968 Sq Ft

    3 Nautical Way, Gray, ME 04039

    Welcome to 3 Nautical Way. This stunning custom designed one level multi generational home is a breath of fresh air. Each unit of this home is absolutely stunning. Located in a private setting yet conveniently located near the turnpike, shopping & all the outdoor recreation Maine can offer. Gorgeous landscaped yard, expansive garages & private back decks with hot tub, wooden slab bar & timber

    Leah Gagne Locations Real Estate Group LLC

    3 Nautical Way, Gray, ME 04039
  • /51

    $1,099,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 3,299 Sq Ft

    65 Sky Dr, Windham, ME 04062

    A like-new custom home, meticulously designed, that makes an unforgettable statement in one of the most sought-after Lakes Region neighborhoods. Located just minutes from the charm of downtown Windham, this stunning property is ideally positioned just a mile away from all the conveniences of the town center, and offers the best of both worlds—seclusion and accessibility. You'll enjoy the peaceful

    Bruce Davis Engel & Volkers Casco Bay

    65 Sky Dr, Windham, ME 04062
  • /32

    $1,250,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,225 Sq Ft

    27 Carriage Hill, North Yarmouth, ME 04097

    Style, Space & Serenity in North Yarmouth. Set on over an acre at the end of a quiet, established road, 27 Carriage Hill is a newly-built home that delivers modern comfort, timeless finishes, and room to grow—all in a peaceful wooded setting.With 4 bedrooms, including a serene primary suite with a custom walk-in closet and spa-like bath featuring a double vanity, rainfall shower, and

    Liza Nelson Portside Real Estate Group

    27 Carriage Hill, North Yarmouth, ME 04097
  • /20

    $324,900

    • 2 Beds
    • 1 Bath
    • 1,664 Sq Ft

    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
  • /36

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft

    34 Trails End Rd, Windham, ME 04062

    Many uses possible for this home. Second floor of garage would make a great apartment or in-law . also the daylight basement has a separate entrance and could have many uses.Zoning allows for many uses.

    Tom Noonan Allied Real Estate

    34 Trails End Rd, Windham, ME 04062
  • /5

    $550,000

    • Land
    • 10 Acres
    • $56,936 per Acre

    TBD Anglers Dr, Cumberland, ME 04021

    Exceptional 9.66 Acre Lot to Build Your Dream Estate!Welcome to an extraordinary opportunity to own 9.66 acres of open, gently rolling pastureland - the perfect canvas to create the estate of your dreams. This expansive parcel offers the ideal setting for a luxurious and private estate.With frontage on both the public Range Road and the private Anglers Drive, the property provides

    Melanie Cran Michael Navarro Elevate Maine Realty

    TBD Anglers Dr, Cumberland, ME 04021
  • /53

    $660,000

    • 3 Beds
    • 2 Baths
    • 2,118 Sq Ft

    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
  • /45

    $598,500

    • 3 Beds
    • 2 Baths
    • 2,750 Sq Ft

    31 Legrow Rd, Gray, ME 04039

    Custom Built fully dormered Cape on just over 4 private acres in Gray. This lot is hard to find, set way back off the road with an open and level back yard perfect for pets/play/gardening or entertaining. Other features of the home include a new roof, heating system, windows and appliances within the last 5 years, large rooms, tons of natural light, a conveinient mudroom/breezeway between the

    Jason Bisson Cottage & Co Real Estate

    31 Legrow Rd, Gray, ME 04039
  • /70

    $595,000

    • 3 Beds
    • 2 Baths
    • 2,001 Sq Ft

    10 Riverside Ridge Rd, Windham, ME 04062

    OPEN HOUSE - Saturday, 6/7, 11am-1pm. Don't miss this beautifully maintained home nestled on a spacious and attractively landscaped lot in a highly convenient location. This property offers a perfect blend of comfort, functionality, and outdoor enjoyment. Large, open-concept kitchen and living room ideal for entertaining and everyday living. The kitchen features oversized island with granite

    Matthew DiBiase Landing Real Estate

    10 Riverside Ridge Rd, Windham, ME 04062
  • /9

    $140,400

    • Land
    • 1.43 Acres
    • $98,182 per Acre

    14 Vista Dr, Windham, ME 04062

    1.4 acres with 1152 Sf shop/barn/garage waiting for your development ideas Near Highland Lake, 15 minutes from Portland, come see it today!

    Bryce Hamilton Coldwell Banker Realty

    14 Vista Dr, Windham, ME 04062
  • /32

    $450,000

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft

    11 Loon Ln, Windham, ME 04062

    Discover the perfect blend of comfort, convenience, and carefree living in this stunning 2-bedroom, 2-bath condo, ideally situated in Windham's premier 55+ association. Skip the hassles of new construction—this beautifully maintained, like-new unit offers an efficient open floor plan designed for easy, maintenance-free living. Step inside to find a bright and sunny kitchen featuring a spacious

    Alicia Frech Ramsey Pulkkinen A Team Realty

    11 Loon Ln, Windham, ME 04062
  • /9

    $179,000

    • Land
    • 1.14 Acres
    • $157,018 per Acre

    18 Pine Dr, Windham, ME 04062

    Buildable Lot with Lake Access Just 15 Minutes from PortlandLooking for lake access without the long drive? This is it. Located just over the Falmouth line and minutes from Portland, this wooded and level lot offers immediate access to Highland Lake and is ready for your dream home—or home with ADU. According to the Town of Windham, the lot is grandfathered and buildable, making this a rare

    Tom Landry Benchmark Real Estate

    18 Pine Dr, Windham, ME 04062
  • /4

    $200,000

    • Land
    • 14 Acres
    • $14,535 per Acre

    76 Mayall Rd, Gray, ME 04039

    13.76 acres very private area with long views. Two lots cleared with soils test.

    Charles Tufts Coldwell Banker Team Real Estate

    76 Mayall Rd, Gray, ME 04039
  • /8

    $200,000

    • Land
    • 1.60 Acres
    • $125,000 per Acre

    68 Sky Dr, Windham, ME 04062

    Discover the perfect blend of privacy and convenience with this 1.6-acre parcel of land. This lot offers the tranquility of nature while being just minutes away from local amenities. Boundaries defined with visible pins. Minutes from North Windham for shopping, dining and entertainment. Close to nearby lakes for boating, fishing and swimming. Under 10 minutes to I-95.*Town has not officially

    Hannah Richard Locations Real Estate Group LLC

    68 Sky Dr, Windham, ME 04062
  • /79

    $699,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 3,039 Sq Ft

    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
  • /60

    $2,100,000

    • 3 Beds
    • 2.5 Baths
    • 1,984 Sq Ft

    7 Passby Point Rd, Windham, ME 04062

    Having one of the most exquisite views on Little Sebago Lake, this property has it all! Over 200' of open frontage. Ideal for entertaining, the gorgeous stone patio includes a gas fire pit & plenty of room for your guests to enjoy tremendous sunsets. The sellers have even hosted several weddings at this beautiful location. The interior of the home has been completely updated from top to bottom

    Claire Zegouros Maine Real Estate Experts

    7 Passby Point Rd, Windham, ME 04062
  • /71

    $609,999

    • 3 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    27 Motorcycle Dr, Windham, ME 04062

    Spacious and beautiful large ranch home set in a peaceful rural location. This 3-bedroom, 2.5-bathroom property offers a perfect blend of modern comfort and timeless charm. Inside, you'll find a thoughtful mix of wood, luxury vinyl plank (LVP), and tile flooring, creating a warm and inviting atmosphere throughout. The home features an open and updated kitchen and new appliances, ideal for both

    Michael Cloutier Coldwell Banker Realty

    27 Motorcycle Dr, Windham, ME 04062
  • /3

    $5,250,000

    • Land
    • 283 Acres
    • $18,580 per Acre

    0 Mayall, Gray, ME 04039

    Rare opportunity to acquire 282± acres of undeveloped land in Southern Maine. Level, cleared, and ready for immediate use - ideal for agricultural use and/orresidential development. Located 8 minutes (4 miles) from I-95 Exit 63, providing easy access to Portland andsurrounding cities. Exceptional scale with soil and water resources suitable for agricultural use.

    Drew Sigfridson The Boulos Company

    0 Mayall, Gray, ME 04039
  • /7

    $189,900

    • Land
    • 6 Acres
    • $31,650 per Acre

    90 Smith Rd, Windham, ME 04062

    Here is your opportunity to build or bring your home to a large 6 acre lot. This lot is newly created form a larger lot split from 88 Smith road which is also for sale. Driveway is grubbed out and ready for your plans. Property has recently been subdivided to create the parcel. Soils have been done and septic plan is attached.

    Michael Jacobson Kre Brokerage Group

    90 Smith Rd, Windham, ME 04062
  • /16

    $950,000

    • Land
    • 2.61 Acres
    • $363,985 per Acre

    Lot #1 Chamberlain Dr, Windham, ME 04062

    Seize this incredible opportunity to acquire 2.61 acre surveyed parcel of prime land, is perfectly suited for residential or commercial development. Located just off Route 302 and Tandberg Trail, this highly visible and accessible property offers zoning flexibility with the potential to construct 60- 64 residential units, mixed use or retail/ flex commercial buildings in a growing area with

    Marc Fishman Keller Williams Realty

    Lot #1 Chamberlain Dr, Windham, ME 04062
  • /64

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,984 Sq Ft

    3 Nautical Way Unit A, Gray, ME 04039

    Welcome to 3A Nautical Way, Gray. This beautifully designed one level three bedroom, two bath condo offers it all. Located in a private setting yet conveniently located near the turnpike, shopping & all the outdoor recreation Maine can offer. Beautifully landscaped yard, expansive garage & private back deck with propane hookup for the grill. The kitchen offers hickory cabinets, granite counter

    Leah Gagne Locations Real Estate Group LLC

    3 Nautical Way Unit A, Gray, ME 04039
  • /76

    $729,000

    • 3 Beds
    • 2 Baths
    • 1,984 Sq Ft

    3 Nautical Way Unit B, Gray, ME 04039

    Welcome to 3B Nautical Way. This stunning custom designed one level three bedroom, two bath condo is a breath of fresh air. Located in a private setting yet conveniently located near the turnpike, shopping & all the outdoor recreation Maine can offer. Gorgeous landscaped yard, expansive garage & private back deck with hot tub, wooden slab bar & timber beam swing, huge walkout basement with work

    Leah Gagne Locations Real Estate Group LLC

    3 Nautical Way Unit B, Gray, ME 04039
  • /120

    $1,388,000

    • 4 Baths
    • 3,968 Sq Ft

    3 Nautical Way, Gray, ME 04039

    Welcome to 3 Nautical Way. This stunning custom designed one level two unit home is a breath of fresh air. Located in a private setting yet conveniently located near the turnpike, shopping & all the outdoor recreation Maine can offer. Gorgeous landscaped yard, expansive garages & private back decks with hot tub, wooden slab bar & timber beam swing. Custom designed kitchens with high end

    Leah Gagne Locations Real Estate Group LLC

    3 Nautical Way, Gray, ME 04039
  • /5

    $875,000

    • Land
    • 88 Acres
    • $9,943 per Acre

    24 Portland Rd, Gray, ME 04039

    Two parcels being sold together. Beautiful wooded lot both commercially zoned out front and residential out back approximately 88 acres. The lot consist of large trees a pristine babbling brook with small waterfalls and rock walls. Keep it for a large private family compound or perfect for a subdivision.

    Derek Drumtra Ray Landing Real Estate

    24 Portland Rd, Gray, ME 04039
  • /2

    $485,000

    • Land
    • 22 Acres
    • $22,045 per Acre

    224 Shaker Rd, Gray, ME 04039

    Excellent opportunity in RRA zone—large tract near Dry Mills corner. Level lot offers over 800' of frontage on Route 26. Close to I-95 (Maine Turnpike).

    Cheri Bonawitz Malone Commercial Brokers, Inc.

    224 Shaker Rd, Gray, ME 04039
  • /33

    $599,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,711 Sq Ft

    62 Oaken Ridge Unit 2, North Yarmouth, ME 04097

    Welcome to Oaken Ridge - A Distinctive Townhome Community Surrounded by Nature.Discover a truly unique living experience at Oaken Ridge, where the ease of condo living meets the tranquility of a private, wooded setting. Nestled on over 30 acres with portions along the Royal River, this intimate community of just six townhomes offers both peaceful seclusion and easy access to a vibrant

    Mary Conroy Portside Real Estate Group

    62 Oaken Ridge Unit 2, North Yarmouth, ME 04097
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