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5-Bedroom Homes for Sale in Cumberland County ME

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  • /19

    $539,000

    • 5 Beds
    • 2 Baths
    • 2,256 Sq Ft

    244 Ray St, Portland, ME 04103

    Discover this exceptional property at 244 Ray St, Portland, Maine. It features five large bedrooms and two large bathrooms, offering comfort and space for residents. The large driveway provides ample parking, while the expansive back deck is perfect for relaxation.Equipped with a sprinkler system and fire alarm system, it ensures safety and convenience. This versatile property can be used for

    Agent Photo

    Davian Akers

    Keller Williams Realty

    (207) 531-5853

    244 Ray St, Portland, ME 04103
  • /32

    $1,650,000

    • 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
  • /36

    $1,250,000

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

    139 Newbury St, Portland, ME 04101

    Discover 139 Newbury Street, a stunning Victorian townhouse in the heart of Portland's most sought-after neighborhood. This historic gem offers endless potential and ample off-street parking (4+ spots). Currently set up as a first-floor office space with preserved architectural details and a spacious two-story apartment unit that's perfect for a live-work setup or could easily be transformed into

    Agent Photo

    David Banks

    RE/MAX By The Bay

    (207) 690-6259

    139 Newbury St, Portland, ME 04101
  • /40

    $4,375,000

    • 7 Beds
    • 10 Baths
    • 8,464 Sq Ft

    3 Canter Ln, Cape Elizabeth, ME 04107

    Privacy. Serenity. Sanctuary. Presenting The Woodside Estate, a rare 16 acre property in the coastal town of Cape Elizabeth. The parcel is bordered by 200 acres of conservation land with recreational trails leading directly to the Atlantic Ocean and Portland Head Light. White clapboards, estate gardens and artisanal stonework blend perfectly with the natural setting. Fountains interspersed on the

    Agent Photo

    David Banks

    RE/MAX By The Bay

    (207) 386-9237

    3 Canter Ln, Cape Elizabeth, ME 04107
  • /53

    $3,195,000

    • 5 Beds
    • 7 Baths
    • 6,225 Sq Ft

    193 Foreside Rd, Falmouth, ME 04105

    A striking three-story Colonial set along one of Falmouth Foreside's most sought-after stretches. Reimagined top to bottom in 2020, this home blends elevated design with dramatic living spaces and sweeping water views from nearly every room. The main level is bright and open, with clean lines, thoughtful details, and a soaring two-story great room that adds a sense of grandeur. For cozier

    Agent Photo

    David Banks

    RE/MAX By The Bay

    (833) 356-3225

    193 Foreside Rd, Falmouth, ME 04105
  • /36

    $399,900

    • 5 Beds
    • 2 Baths
    • 1,600 Sq Ft

    28 Acorn Rd, Naples, ME 04055

    Looking for a peaceful Maine getaway? This charming family compound sits on 0.78 acres along the beautiful Crooked River, with 208 feet of water frontage and direct access to Sebago Lake—giving you over 40 miles of boating to explore. The property includes two rustic seasonal homes.The Brown Chalet has three bedrooms, one bathroom, a full kitchen, and a comfortable living room with plenty of

    Agent Photo

    Jocelyn O'Rourke-Shane

    Maine Real Estate Choice

    (207) 489-2832

    28 Acorn Rd, Naples, ME 04055
  • /75

    $945,000

    • 6 Beds
    • 2 Baths
    • 1,440 Sq Ft

    489 Leisure Ln, Frye Island, ME 04071

    Stunning Waterfront Cottage on Sebago Lake - Fully Furnished, Prime Rental Income!Experience lakeside living at its finest with this exceptional 6-bedroom, 2-bathroom cottage located directly on the shores of Sebago Lake. Boasting a sandy beach, private boat dock, and mooring, this reverse-design home offers breathtaking west-facing views and unforgettable sunsets over the White Mountains.The

    Agent Photo

    Lois O'Connor

    Sunset Lakes Real Estate

    (877) 799-0465

    489 Leisure Ln, Frye Island, ME 04071
  • /103

    $2,000,000

    • 6 Beds
    • 3 Baths
    • 4,980 Sq Ft

    284 Allen Rd, Pownal, ME 04069

    Step into the classic New England charm of William Allen Farm, a breathtaking estate set on just over 52 acres of rolling fields, wooded trails, and a serene heart-shaped pond. Located just 1.5 miles from Pineland Farms and 20 minutes from Portland, this property offers a rare opportunity to create the dream you've always envisioned—whether as a private estate, elegant event venue, or

    Mikki Voter Coldwell Banker Realty

    284 Allen Rd, Pownal, ME 04069
  • /50

    $1,650,000

    • 5 Beds
    • 4.5 Baths
    • 4,666 Sq Ft

    1241 Harpswell Island Rd, Harpswell, ME 04066

    Nestled on the serene shores of Orr's Island in Harpswell, Maine, this exquisite waterfront estate at 1241 Harpswell Island Road offers a rare blend of timeless charm and contemporary elegance. Spanning 445 feet of diverse waterfront along Gun Point Cove, the property boasts a deep-water dock, a protected shallow tidal area, sandy shores at low tide, a boat mooring, and a private dock, creating

    Dennis Duggan Legacy Properties Sotheby's International Realty

    1241 Harpswell Island Rd, Harpswell, ME 04066
  • /50

    $1,350,000

    • 5 Beds
    • 2.5 Baths
    • 3,579 Sq Ft

    274 Black Point Rd, Scarborough, ME 04074

    This beautifully updated 5-bedroom, 2.5-bath farmhouse blends timeless character with modern comfort on a stunning 1.19-acre lot in Scarborough. The first floor offers a gourmet kitchen, updated throughout, that flows seamlessly into spacious living and entertaining areas. The large, renovated primary bathroom serves as a true oasis within the home, featuring an oversized steam shower, heated

    Kathryn Treem Keller Williams Realty

    274 Black Point Rd, Scarborough, ME 04074
  • /56

    $2,600,000

    • 8 Beds
    • 3.5 Baths
    • 5,184 Sq Ft

    70 Carroll St, Portland, ME 04102

    Enjoying a quiet corner position in the heart of Portland's coveted Historic Western Promenade neighborhood, the Charles F. Flagg residence, c. 1913, is a rare beauty and among the precious few private residences designed by noted architect George Burnham. This exceptional residence presents elegant Colonial Revival architectural personalities, 5,184 sf+/-. of distinctive living space, 16 rooms

    William Davisson Town & Shore Real Estate

    70 Carroll St, Portland, ME 04102
  • /67

    $1,425,000

    • 5 Beds
    • 3.5 Baths
    • 4,719 Sq Ft

    165 Falmouth Rd, Falmouth, ME 04105

    Discover the perfect blend of historic charm and modern updates in this spacious and special 5-bedroom home. The James Merrill house is among the longest standing homes in Falmouth dating to 1738 and home to the Merrill family for over 200 years. From the moment you step inside, you'll be captivated by the warmth and character of this remarkable historic property. While history and character

    Julia Young Sunday River Real Estate

    165 Falmouth Rd, Falmouth, ME 04105
  • /52

    $3,495,000

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

    20 Long Point Island, Harpswell, ME 04079

    Serendipity and location give Long Point Island breathtaking views. Low tide gives the proximity of friends and neighborhood; high tide the privacy and sounds of a bird sanctuary and the sea. Views and Views. Portland boat traffic heading down east on the horizon. The boats of Harpswell's working waterfront pulling traps and nets as they meander among the Casco Bay Islands. The comings and goings

    Rhonda Clark Harcourts Waterfront & Fine Properties

    20 Long Point Island, Harpswell, ME 04079
  • /110

    $3,700,000

    • 5 Beds
    • 5 Baths
    • 3,604 Sq Ft

    12 Steamboat Wharf Ln, Harpswell, ME 04079

    A Rare Coastal Gem on Bailey IslandOffered for the first time in decades, this extraordinary estate combines history, luxury, and natural beauty in one of coastal Maine's most beloved settings.Perched on one of Bailey Island's highest points, the property boasts unparalleled panoramic views of Casco Bay and Mackerel Cove. With southeastern exposure, you'll enjoy sun-filled days and spectacular

    Roxanne York Roxanne York Real Estate

    12 Steamboat Wharf Ln, Harpswell, ME 04079
  • /12

    $1,500,000

    • 6 Beds
    • 5 Baths
    • 5,114 Sq Ft

    273 State St, Portland, ME 04101

    A rare opportunity to own The Mercury Inn, a fully renovated and reimagined 1890s Victorian mansion located in Portland, Maine's peninsula. This turnkey property offers a unique blend of modern design and historic charm, featuring four spacious living room/bedroom guest suites, each with their own private bathroom. Each floor has a delightfully appointed kitchenette that guests can enjoy as well.

    William Fuller Legacy Properties Sotheby's International Realty

    273 State St, Portland, ME 04101
  • /58

    $2,195,000

    • 5 Beds
    • 5.5 Baths
    • 5,207 Sq Ft

    1 Cardinal Ln, Cape Elizabeth, ME 04107

    Welcome to this stunning, move-in ready custom home offering three spacious levels of refined living. Privately nestled on a 2.4-acre lot abutting the desirable, walkable Cross Hill neighborhood, this home blends elegance, comfort, and cozy spaces—thoughtfully designed for today's lifestyle.At the heart of this sun-filled home is a brand-new chef's kitchen with premium appliances, a Bertazzoni

    Heather Mayer Portside Real Estate Group

    1 Cardinal Ln, Cape Elizabeth, ME 04107
  • /64

    $1,995,000

    • 6 Beds
    • 3 Baths
    • 3,696 Sq Ft

    160 Lyons Point Rd, Raymond, ME 04071

    OPEN HOUSE SUNDAY June 1st from 10-11:30!Welcome to 160 Lyons Point Road, a stunning 6-bedroom, 3-bathroom lakefront retreat nestled on the shores of Little Sebago Lake in Gray, Maine. This spacious, beautifully maintained home offers the perfect blend of year-round comfort and vacation-style living.With direct walk-out access to the lake, the property is designed for those who crave the

    Lisa Andrade Dream Home Realty LLC

    160 Lyons Point Rd, Raymond, ME 04071
  • /34

    $1,900,000 Open Sat 10AM - 11:30AM

    • 6 Beds
    • 5 Baths
    • 4,952 Sq Ft

    20 Thomas St, Portland, ME 04102

    Located in Portland's coveted West End neighborhood, this exquisite 1899 home, designed by renowned architect John Calvin Stevens for philanthropists Edward and Mary Staples, seamlessly blends historic charm with modern convenience. Beyond its timeless elegance, the property offers valuable amenities, including a third-floor rental apartment, which can easily be incorporated into the main house

    Elise Kiely Legacy Properties Sotheby's International Realty

    20 Thomas St, Portland, ME 04102
  • /123

    $1,404,000

    • 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
  • /63

    $1,750,000

    • 5 Beds
    • 5.5 Baths
    • 5,160 Sq Ft

    697 Fort Hill Rd, Gorham, ME 04038

    In 1776 our Declaration of Independence was signed AND this amazing gentleman's farm was built! Now, it is your chance to continue the tradition of American Excellence. Modern conveniences were added to this traditional Maine farmhouse but the charm is still present in every room. This farm is set up like an all inclusive resort. There is plenty of sleeping space and even living space for

    Sheila Helmuth Maine Real Estate Experts

    697 Fort Hill Rd, Gorham, ME 04038
  • /8

    $1,599,000

    • 5 Beds
    • 3.5 Baths
    • 3,709 Sq Ft

    192 Stewart Dr, Scarborough, ME 04074

    * NEW PRICE REFLECTS 909 SQ FT ADDED TO PRINT- TOTAL 3709 Organic. Bold. Customized. Neutral. Luxury Welcome to the to be built 192 Stewart Drive in the highly sought after & coveted community of Dunstan Crossing in Scarborough, Maine. This home is being graciously crafted by KB Building Contractors, a well known local and respected builder known for lasting quality & high end

    Victoria Bedard Bedard Homes and Realty

    192 Stewart Dr, Scarborough, ME 04074
  • /59

    $1,395,000 New Construction

    • 5 Beds
    • 3 Baths
    • 2,433 Sq Ft

    300 North Rd, Yarmouth, ME 04096

    This stunning, brand new home blends the timeless appeal of a farmhouse with the clean, sophisticated lines of contemporary design—all set in the heart of one of Maine's most desirable communities. Now under construction with anticipated completion by June 1, this 5-bedroom, 3-bath home offers a bright, open layout and exceptional attention to detail throughout.Perfectly sited on an open

    Matt Pouliot Pouliot Real Estate

    300 North Rd, Yarmouth, ME 04096
  • /25

    $479,900

    • 5 Beds
    • 2.5 Baths
    • 2,202 Sq Ft

    12 Church St, Bridgton, ME 04009

    This meticulously renovated property is spacious, centrally located, and ready for its next owner. Whether you're looking for an investment, vacation property, or full-time home, this home offers impressive versatility, boasting a studio in-law suite and excellent rental history. This property is also being offered with the option of purchasing the lot behind it for $30,000, which not only allows

    Jesse Brooks Keller Williams Realty

    12 Church St, Bridgton, ME 04009
  • /45

    $4,995,000

    • 7 Beds
    • 4.5 Baths
    • 4,300 Sq Ft

    1 & 9 Franklin Terrace, South Portland, ME 04106

    Willard Beachfront Compound with Panoramic Ocean Views.Welcome to this rare beachfront gem located in South Portland's highly desirable Willard Beach neighborhood. This exceptional property offers a luxurious coastal lifestyle with two distinct homes—a fully remodeled four+ bedroom main residence and a charming three-bedroom guest house—making it ideal for multigenerational living, rental income,

    Anne Ross-Murray F.O. Bailey Real Estate

    1 & 9 Franklin Terrace, South Portland, ME 04106
  • /13

    $120,000

    • 5 Beds
    • 2 Baths
    • 896 Sq Ft

    3 Aube Ln, Standish, ME 04084

    Opportunity knocks in this sweet Standish neighborhood! Situated on a sunny, wooded lot with .42+/- acres, 5 Aube Lane offers rare potential! The 1972 mobile home is being sold as-is and offers a great chance for those looking to renovate, remove and replace, or build new (confirm options with the town).The property includes private septic and well, and is conveniently located near Sebago Lake,

    Belinda Desmond Keller Williams Realty

    3 Aube Ln, Standish, ME 04084
  • /48

    $514,500

    • 5 Beds
    • 2.5 Baths
    • 2,312 Sq Ft

    1479 Washington Ave, Portland, ME 04103

    This spacious 5-bedroom, 3-bath garrison offers comfortable living and convenience just one block from the Northgate Shopping Center. The home featureswood floors throughout, with a large gathering room on the second floor, and basement family room with fireplace.. A large fenced yard provides excellent outdoor space, perfect for recreation or pets, and the oversized 4 car garage completes the

    Bryce Hamilton Coldwell Banker Realty

    1479 Washington Ave, Portland, ME 04103
  • /44

    $699,900

    • 5 Beds
    • 2.5 Baths
    • 1,787 Sq Ft

    24 Mitton St, Portland, ME 04102

    Five-Bedroom, two and a half bath Victorian totally restored just off the Portland Peninsula, ready and in move-in condition. Situated just minutes from Thompson Point, the Interstate system and close to the Airport and Train/Bus Station, the World is your Oyster. The Restoration Contractor has touched all surfaces. The new staircases, new hardwood, new kitchen featuring granite and streamline

    Mike Bunting Coldwell Banker Realty

    24 Mitton St, Portland, ME 04102
  • /101

    $1,295,000 Open Sat 11AM - 1PM

    • 6 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    13 Gallinari Way, Bridgton, ME 04009

    Remarkable opportunity to own a large and beautiful Waterfront home on the amazing Highland Lake that is walking distance to the Downtown area with walking trails, shopping, bookstore, movie theaters, restaurants and bars. Incredible views of Mount Washington and Pleasant Mountain as well as those spectacular sunsets on your own private water frontage. This home has been thoroughly updated, new

    Mick Early The Lakes Real Estate

    13 Gallinari Way, Bridgton, ME 04009
  • /58

    $1,190,000

    • 5 Beds
    • 3.5 Baths
    • 3,787 Sq Ft

    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 efficiency.

    Vicki Kennedy RE/MAX Oceanside

    11 Lieutenants Dr, Windham, ME 04062
  • /49

    $519,000

    • 5 Beds
    • 2 Baths
    • 2,276 Sq Ft

    2 Gunstock Rd, Scarborough, ME 04074

    Spacious Split-Entry home with ADU (In-Law) in desirable Pleasant Hill. First time on the market since 1978. Conveniently located near local beaches, Portland, Pleasant Hill Preserve, schools, shopping, and highways. Set on a 0.3-acre lot, the exterior features vinyl siding, mature trees, a 2-car attached garage, and a large driveway with ample parking. Roof replaced in 2019. The main level

    Elizabeth Marks The Real Estate Store

    2 Gunstock Rd, Scarborough, ME 04074
  • /62

    $1,000,000

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

    1880 Harpswell Neck Rd, Harpswell, ME 04079

    Welcome to 1880 Harpswell Neck Road — a rare opportunity to own a piece of coastal Maine history with breathtaking water views and incredible potential. This spacious 11-room, 5-bedroom, 2-bath, 2,470 square foot farmhouse is waiting for your vision to bring it back to life.Set on the scenic shores of Harpswell, this antique home is a canvas for your imagination. Whether you envision a stunning

    Eric Flynn Excellence Realty

    1880 Harpswell Neck Rd, Harpswell, ME 04079
  • /22

    $599,000

    • 5 Beds
    • 2 Baths
    • 2,464 Sq Ft

    150 Holmes Rd, Scarborough, ME 04074

    Location, Privacy, and Versatility - This Unique Scarborough Home Has It AllTucked away in a serene setting, this exceptional Scarborough property offers the perfect blend of privacy, space, and flexibility—featuring two distinct living quarters ideal for multi-generational living, guests, or added rental potential.As you step inside, you're welcomed by oversized windows that flood the

    Ruth Summers Keller Williams Realty

    150 Holmes Rd, Scarborough, ME 04074
  • /50

    $5,200,000

    • 5 Beds
    • 5 Baths
    • 4,969 Sq Ft

    361 Cape Rd, Raymond, ME 04071

    Sited on the pristine waters of Sebago Lake, this private waterfront estate provides vast and elevated westerly views over one of New England's largest lakes to the White Mountains of New Hampshire. This region is well known for its recreational activities that include outstanding boating, swimming, fishing, golfing and winter downhill skiing all within 25± miles of the property. Encompassed

    John Saint-Amour LandVest, Inc.

    361 Cape Rd, Raymond, ME 04071
  • /58

    $5,975,000

    • 5 Beds
    • 5 Baths
    • 4,969 Sq Ft

    Unlisted Address

    Sited on the pristine waters of Sebago Lake, this private waterfront estate provides vast and elevated westerly views over one of New England's largest lakes to the White Mountains of New Hampshire. This region is well known for its four-season recreational activities that include outstanding boating, swimming, fishing, golfing and winter downhill skiing all within 25± miles of the property. The

    John Saint-Amour LandVest, Inc.

    Unlisted Address
  • /48

    $824,999

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

    2 Evergreen Cir, Cape Elizabeth, ME 04107

    Tucked away at the end of a quiet cul-de-sac in one of Cape Elizabeth's most beloved neighborhoods, this warm and welcoming home offers a rare combination of space, comfort, and connection to nature. From the moment you arrive, there's a sense of peace—kids riding bikes down the street, neighbors waving hello, and the kind of quiet you didn't think existed anymore. Inside, you'll find a spacious

    Jaylan Archer Keller Williams Coastal and Lakes & Mountains Realty

    2 Evergreen Cir, Cape Elizabeth, ME 04107
  • /49

    $479,000

    • 6 Beds
    • 2.5 Baths
    • 2,460 Sq Ft

    2 School St, Bridgton, ME 04009

    Step into the timeless elegance of 2 School Street, a beautifully restored 1900s home nestled in the heart of downtown Bridgton. Thoughtfully and meticulously remodeled, this residence seamlessly blends historic charm with modern convenience.Boasting five spacious bedrooms, plus an additional room ready for finishing, this home offers versatility to suit your needs. Once a two-unit property, it

    Samantha Estes Oberg Insurance & Real Estate Agency, Inc.

    2 School St, Bridgton, ME 04009
  • /45

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 4,816 Sq Ft

    319 Harris Rd, Cumberland Center, ME 04021

    Welcome to 319 Harris Road in Cumberland - Where Privacy, Versatility & Convenience ConvergeSet on a private 3-acre lot, this exceptional home offers over 4,000 sq ft of bright, flexible space ideal for multigenerational living, or simply spreading out in comfort. The main house includes 4 bedrooms, 3.5 baths, and an attached ADU/in-law apartment with its own entrance, full kitchen, living area,

    Ingrid Vanni Portside Real Estate Group

    319 Harris Rd, Cumberland Center, ME 04021
  • /60

    $740,000

    • 6 Beds
    • 2 Baths
    • 3,113 Sq Ft

    244 Concord St W, Portland, ME 04103

    Attention investors, flippers, and contractors! Welcome to 244 Concord Street West, located in Portland's desirable Deering neighborhood. This 1873 home and oversized barn are filled with original charm and offer a rare chance to restore and reconfigure a sizable property for modern use. Recent updates (Nov 2024 & Mar 2025) include new roofs on the house and barn, freshly painted siding, a new

    Fernanda McLaughlin Hearth & Key Realty

    244 Concord St W, Portland, ME 04103
  • /124

    $3,950,000

    • 7 Beds
    • 5 Baths
    • 4,265 Sq Ft

    8 Linnel Dr, Bailey Island, ME 04003

    Exceptional Oceanfront Compound on Bailey IslandEndless Possibilities | Over 1 Acre Total | 200+ Feet of Private Ocean FrontageFamily compound, investment property, or business opportunity — this rare and versatile oceanfront estate offers unparalleled potential in one of Maine's most picturesque coastal settings. Comprising three adjacent parcels, the property totals over 1.02 acres, including

    Roxanne York Roxanne York Real Estate

    8 Linnel Dr, Bailey Island, ME 04003
  • /46

    $1,100,000

    • 6 Beds
    • 8 Baths
    • 7,215 Sq Ft

    1851 Washington Ave, Portland, ME 04103

    Welcome to 1851 Washington Avenue—an extraordinary custom-built 1950s brick Colonial in Portland's sought-after North Deering neighborhood. Designed with both comfort and flexibility in mind, this expansive home offers over 5,900 sqft of living space, plus an office/recreation space of 1300 sqft on nearly an acre—perfect for a family looking to thrive, grow, and make lasting memories. Inside,

    Megan McShane Redfin Corporation

    1851 Washington Ave, Portland, ME 04103

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