Winthrop, ME Homes

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  /124

  $995,000

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172 Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY AND TITLE COMPLETED and ready for quick closing! Now includes a 20-foot right of way to Annabessacook Lake and 20 sprawling acres!! This custom-built executive estate offers unparalleled luxury and comfort. A true one-of-a-kind haven, it blends resort-style amenities with high-end finishes for the perfect combination of elegance and functionality. Originally completed in 1997 and

  

  Tim Dunham

  Tim Dunham Realty

  (207) 367-3848

  

  172 Annabessacook Rd, Winthrop, ME 04364
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  /15

  $2,650 per month

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • House for Rent

  25 Welchs Point Rd, Winthrop, ME 04364

  Property Id: 2204388Welcome to your new home on Welch Point Rd in East Winthrop — a charming 2BR, 1BA single-family house with the perfect mix of lakefront living and professional convenience.Set on a spacious 1.34-acre lot, this home offers direct access to Cobbosseecontee Lake just steps away. Inside you'll find a modern kitchen with granite countertops and tile flooring,

  25 Welchs Point Rd, Winthrop, ME 04364
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  /59

  $280,000 Sold Nov 03, 2025

  • 792 Sq Ft
  • $354/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  347 Metcalf Rd, Winthrop, ME 04364

  Discover the charm of this cozy two bedroom, single story Cape style home with a versatile loft and a stunning brick fireplace taking center stage in the living area. Though modest in size, this home is filled with character and warmth. Step outside to a spacious backyard featuring multiple fruit trees, perfect for anyone who dreams of harvesting from their own land. Adding even more value, the

  Rebecca Wilson Better Homes & Gardens Real Estate/The Masiello Group

  

  347 Metcalf Rd, Winthrop, ME 04364
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  /37

  Est $235,716 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 896 Sq Ft

  87 Woodland Rd, Winthrop, ME 04364

  

  87 Woodland Rd, Winthrop, ME 04364
• 

  

  

  /60

  $994,999

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172-B Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY & TITLE COMPLETED and ready for quick closing! Now includes 20 sprawling acres and a 20-foot right of way to Annabessacook Lake! This custom-built executive estate blends resort-style amenities with refined finishes for the perfect mix of luxury and functionality. Originally completed in 1997 and beautifully renovated in 2019 and 2023, the home offers 6,493 SF of finely crafted

  

  Tim Dunham

  Tim Dunham Realty

  (207) 803-6219

  172-B Annabessacook Rd, Winthrop, ME 04364
• 

  

  /20

  $1,650 per month

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • House for Rent

  19 Pond View Rd, Winthrop, ME 04364

  Large 4 Bed - 2 Bath Mobile Home in Winthrop. Available Now!- Minutes away from Manchester/Augusta with easy access to I-95 - Large Eat-In Kitchen and living room! - Master Bedroom features a spacious private bathroom with a double vanity! - Many recent updates throughout the home! $1,650/Month. 9 Month lease with the option to renew for 12 months. Tenants are

  19 Pond View Rd, Winthrop, ME 04364
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  /47

  $320,000 Sold Oct 27, 2025

  • 2,575 Sq Ft
  • $124/SF
  • 210 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1850

  170 Hathaway Rd, Winthrop, ME 04364

  Back on the Market through no fault of the property. Where old meets new. The charm of this original 1840's Brick Cape paired with a thoughtful 2004 addition. Located on a quiet dead end road, offering 3.3 acres with trees/ fields, wildlife, garden areas and ultimate privacy. The home includes three spacious bedrooms and two full baths. The open kitchen and living area, complete with a cozy

  Heidi Libby NextHome Northern Lights Realty

  

  170 Hathaway Rd, Winthrop, ME 04364
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  /47

  Est $1,111,665 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  76 Pine Point Ln, Winthrop, ME 04364

  

  76 Pine Point Ln, Winthrop, ME 04364
• 

  

  /23

  $249,500 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,879 Sq Ft

  90 Route 133, Winthrop, ME 04364

  MOTIVATED SELLERS - RECENT EXTERIOR PAINT - Step back in time and experience the character of early New England in this beautifully preserved 1790s home, nestled in the heart of Winthrop. This rare gem offers four spacious bedrooms and 1.5 baths, blending historic charm with modern comfort. Features include: four generously sized bedrooms, perfect for family or guests with an additional large

  Heather Perrault Your Home Sold Guaranteed Realty

  

  90 Route 133, Winthrop, ME 04364
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  /10

  $1,150 per month

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • House for Rent

  2 Cloverleaf St, Winthrop, ME 04364

  Completely Renovated 2 bed/1 bath Mobile Home in Winthrop! Coming Soon!- Fully Remodeled Bathroom and Kitchen- Newer Furnace- Newer Flooring Throughout- Washer/Dryer Hookups in the unit! Rent To Own - Terms are $4,000 down. Lot rent of $500. Home payment of $650 for 84 months. Monthly Payment of $1,150. Tenant responsible for all utilities. Electronic Payment or

  2 Cloverleaf St, Winthrop, ME 04364
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  /20

  $14,000 Sold Oct 23, 2025

  • Land
  • 0.49 Acre
  • $28,571 per Acre

  • 91 Days On Market

  35A-12 Woodland Rd, Winthrop, ME 04364

  The sounds of loons, owls and eagles await you on the .49 acre property which slopes to two brooks that flow into Berry Pond. Sitting at the top of the property is an existing bunkhouse with an attached deck in good condition. Fish or just get away on this unique gem of a location which is still only 4 miles from Winthrop.

  Kimberly Granholm LAER

  

  35A-12 Woodland Rd, Winthrop, ME 04364
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  /26

  Est $306,973 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft

  262 Metcalf Rd, Winthrop, ME 04364

  

  262 Metcalf Rd, Winthrop, ME 04364
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  /57

  $539,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,128 Sq Ft

  50 Robin Hood Dr, Winthrop, ME 04364

  Discover more than you'd expect in this beautiful 4-bedroom, 2.5-bath —3,100 Square Foot home-perfect for a growing family—nestled on a private 6.11 - acre lot. This is the home for you, especially if you're looking for a great community suited to families, outdoor recreation, and a quieter, more semi-rural lifestyle. Step inside to a modern kitchen featuring beautiful custom hickory cabinets, a

  Michael Roddy Your Home Sold Guaranteed Realty

  

  50 Robin Hood Dr, Winthrop, ME 04364
• 

  

  /23

  $12,287 per month

  • 3 Beds
  • 1.5 Baths
  • Condo for Rent

  100 Woods Grove Ln Unit ID1255650P, Winthrop, ME 04364

  Welcome to this charming 3-bedroom, 1.5-bathroom retreat located on the serene Annabessacook Lake in Winthrop. This well-maintained home offers a picturesque view of the private waterfront and dock, just steps away from your doorstep. The first floor features a bunkroom with two twin beds and a futon, along with a convenient half bath and washer/dryer. On the second floor, you'll find two

  100 Woods Grove Ln Unit ID1255650P, Winthrop, ME 04364
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  /7

  $53,000 Sold Oct 20, 2025

  • Land
  • 4.5 Acres
  • $11,778 per Acre

  • 1 Day On Market

  Lot 42B Fire Road A-3, Winthrop, ME 04364

  Bring your plans to this peaceful 4.5 acre building site. Presently the property consists of two structures. One with electrical and propane heat on a slab. The second a storage shed. Both with metal roofs. Town water is available at the street.

  Daren Hachey Homestead Realty

  

  Lot 42B Fire Road A-3, Winthrop, ME 04364
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  /48

  Est $547,073 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,136 Sq Ft

  298 Metcalf Rd, Winthrop, ME 04364

  

  298 Metcalf Rd, Winthrop, ME 04364
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  /52

  $448,000

  • 6 Beds
  • 2 Baths
  • 2,872 Sq Ft

  192 Turkey Ln, Winthrop, ME 04364

  Located on a lovely 4-acre lot, this unique 6-bedroom, 2-bath farmhouse boasts over 2800 square feet of living space. The property features a charming porch, perfect for enjoying morning coffee while taking in the scenic views. Inside, you'll find a blend of rustic charm and modern amenities, making it an ideal family home or a serene retreat. Additionally, this home features 2 bedrooms and a

  Lindsay Book The Maine Real Estate Experience

  

  192 Turkey Ln, Winthrop, ME 04364
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  /20

  $2,000 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • House for Rent

  220 Me-133, Winthrop, ME 04364

  Property Id: 1320038This brand new, family-friendly, 2-bedroom cozy, modern cottage packed full of amenities is nestled in the village of Winthrop w/ lake views. There is a large yard with fire pit, snowmobile & walking trail access out back. A 10-minute walk to the beach & boat launch on Maranacook lake, as well as multiple local eateries and shops. A massage studio and sauna are located

  220 Me-133, Winthrop, ME 04364
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  /48

  $429,900 Sold Oct 20, 2025

  • 1,700 Sq Ft
  • $253/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  87 Annabessacook Rd, Winthrop, ME 04364

  Winthrop - Contemporary ChaletThis inviting chalet-style home features 3 bedrooms and a bright, open-concept kitchen, living, and dining area with soaring ceilings and abundant natural light. The spacious primary suite is located upstairs, offering a walk-in closet and private bathroom. A convenient mudroom enhances everyday functionality, while the newly finished bonus/playroom over the

  Jessica Fike Brookewood Realty

  

  87 Annabessacook Rd, Winthrop, ME 04364
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  /73

  Est $498,458 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  91 Wedgewood Dr, Winthrop, ME 04364

  

  91 Wedgewood Dr, Winthrop, ME 04364
• 

  

  /200

  $900,000

  • 3 Beds
  • 2.5 Baths
  • 3,672 Sq Ft

  427 Mount Pisgah Rd, Winthrop, ME 04364

  Cranberry Rock Farm, built in 1815, is a colonial-style farmhouse nestled on 32 private, picturesque acres. This certified-organic farm provides endless possibilities as a private retreat, wedding venue, equestrian property, or more. Perched atop a hillside with southwesterly exposure, it boasts panoramic views of the Presidential Range & Mt. Washington. Enjoy easy entertaining in the open

  Rick Bisson Keller Williams Realty

  

  427 Mount Pisgah Rd, Winthrop, ME 04364
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  /20

  $5,400 per month

  • 1 Bed
  • 1 Bath
  • 810 Sq Ft
  • House for Rent

  11 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200424Little Landing Cottage on Cobbosseecontee LakeNestled on the shores of the prestigious Cobbosseecontee Lake, Little Landing Cottage offers breathtaking water views and direct access to all the lake has to offer. With its charming design and idyllic setting, this property is perfect for those seeking a balance of outdoor adventure and peaceful

  11 Fire Rd W24a, Winthrop, ME 04364
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  /99

  $685,000 Sold Oct 20, 2025

  • 2,922 Sq Ft
  • $234/SF
  • 4 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  173 Loon Cove Ln, Winthrop, ME 04364

  Lakefront living! No need for a vacation home when you live at the waters edge in this beautiful home! Sparkling clear lake is great for swimming, fishing or just relaxing! Main floor offers a beautiful kitchen with granite counters, oak cabinets and two level bar. Double sided propane fireplace is lovely. Large living room and dining room, primary bedroom with bath and guest room. Lower walkout

  Earle Kenney Sprague & Curtis Real Estate

  

  173 Loon Cove Ln, Winthrop, ME 04364
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  /40

  Est $541,860 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,860 Sq Ft

  33 Ledgemere Dr, Winthrop, ME 04364

  

  33 Ledgemere Dr, Winthrop, ME 04364
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  /60

  $475,000

  • 4 Beds
  • 3 Baths
  • 2,674 Sq Ft

  251 Annabessacook Rd, Winthrop, ME 04364

  Beautiful cape cod style home on a pretty country lot, just 5 minutes to downtown Winthrop and 15 minutes to I-95. Very spacious. Offering an eat in kitchen that opens to the massive backyard deck. Front living room, dining room, den, full bath and primary suite bedroom with full bath -- all on the first floor. Second floor offers 4 rooms -- 2 bedrooms, full bath and family room and den. Private

  Earle Kenney Sprague & Curtis Real Estate

  

  251 Annabessacook Rd, Winthrop, ME 04364
• 

  

  /20

  $5,900 per month

  • 2 Beds
  • 1 Bath
  • 865 Sq Ft
  • House for Rent

  7 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200423Cozy Keyes Cottage on Cobbosseecontee LakeWelcome to Cozy Keyes Cottage, a charming lakeside retreat located on the shores of the prestigious Cobbosseecontee Lake. This beautiful property offers an ideal setting for those seeking both adventure and tranquility, with breathtaking lake views and access to a variety of outdoor activities.Perfectly situated

  7 Fire Rd W24a, Winthrop, ME 04364
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  /3

  $108,000 Sold Oct 20, 2025

  • 612 Sq Ft
  • $176/SF
  • 70 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1955

  643 Mount Pisgah Rd, Winthrop, ME 04364

  Here is your opportunity to own this large parcel of land located just outside of Monmouth in the quaint town of Winthrop. This 22.55 acre lot offers so many possibilities, located just minutes away from Wilson Pond, Mount Pisgah Conservation Trails and much more. Use it as your private oasis for hunting, fishing, hiking, four wheeling and snowmobiling or bring your building plans and make it

  Cathy Fifield Keller Williams Realty

  

  643 Mount Pisgah Rd, Winthrop, ME 04364
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  /42

  Est $387,639 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  192 Metcalf Rd, Winthrop, ME 04364

  

  192 Metcalf Rd, Winthrop, ME 04364
• 

  

  /44

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft

  8 Horseshoe Rd, Winthrop, ME 04364

  Rare opportunity to own 9 acres on an island in the middle of Cobbosseecontee Lake! This two bedroom, one bathroom home has been meticulously cared for and in the same family since its construction in the 90's . Tucked away with incredible privacy of maintained tree growth at the front, allows for viewing of the lake without recreational lake life viewing up at the cottage. The home has its own

  Spencer Hazzard Rizzo Mattson

  

  8 Horseshoe Rd, Winthrop, ME 04364
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  /6

  $1,550 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  3 Nason Dr, Winthrop, ME 04364

  Single wide mobile home on private lot. 1200 sq. ft. 2 bedrooms, 1 bath. Livingroom and kitchen combination. 3 season porch. Washer and dryer hookup. Beautiful lot. Close to town. NO SMOKING IN OR AROUND PROPERTY. NO PETS OF ANY KIND. $1550.00 a month. 1st and last. Plus utilities.

  3 Nason Dr, Winthrop, ME 04364
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  /57

  $310,000 Sold Oct 02, 2025

  • 1,680 Sq Ft
  • $185/SF
  • 42 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1790

  16 Old Village Rd, Winthrop, ME 04364

  OPPORUNITY AWAITS! Welcome home to this unique opportunity in Winthrop just a few minutes walk to the head of the famous Cobbosseecontee lake. This spacious 3 bed 1.5 bath home features a 2 car attached garage and an additional outbuilding/shed, providing ample storage for vehicles and personal belongings. Large living room, kitchen and dining room areas. Many of the current features of the home

  Alonzo Michaud Real Broker

  

  16 Old Village Rd, Winthrop, ME 04364
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  /36

  Est $325,535 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,913 Sq Ft

  108 Pamela Dr, Winthrop, ME 04364

  

  108 Pamela Dr, Winthrop, ME 04364
• 

  

  /81

  $680,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft

  150 Pamela Dr, Winthrop, ME 04364

  Stunning Cape Cod - style home that has been meticulously maintained by the original owners. This dormered cape cod is immaculate and tastefully decorated. Updated applianced kitchen with granite counters and adjoining dining room. Living room with cathedral ceilings, sunroom also with cathedral ceilings and skylights is flooded with light and opens onto a backyard deck. Main floor bedroom and

  Earle Kenney Sprague & Curtis Real Estate

  

  150 Pamela Dr, Winthrop, ME 04364
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  /58

  $265,000 Sold Oct 01, 2025

  • 1,212 Sq Ft
  • $219/SF
  • 27 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1969

  984 Sturtevant Hill Rd, Winthrop, ME 04364

  Seller is selling in 'as is' condition. Totally charming single-family Winthrop home! Three bedroom ranch-style home sits on an expansive 1.3 acres and has recent updates. Kitchen with new butcher block counter, new smart appliances, farm sink, open shelving and hardware gives a fresh look! Bathroom updates include new tile shower, vanity, flooring and flush. New leach field in 2022 as well! The

  Pat Ladd Homestead Realty

  

  984 Sturtevant Hill Rd, Winthrop, ME 04364
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  /59

  Est $368,230 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,878 Sq Ft

  17 Pamela Dr, Winthrop, ME 04364

  

  17 Pamela Dr, Winthrop, ME 04364
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  /82

  $420,000 Open Sun 10AM - 12PM

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  333 Stanley Rd, Winthrop, ME 04364

  OPEN HOUSE!!! Sunday, November 9th from 10am - 12pm. Welcome to 333 Stanley Road in Winthrop. This 4 bedroom, 2 bath home is very cozy and has had many updates. The best update is the Bespoke smart kitchen appliances. Heat pumps throughout, heat and cool with great efficiency along with a back up propane Rinnai heater. The finished basement can be a bedroom or a play room and it has its own full

  Dylan Armstrong Sprague & Curtis Real Estate

  

  333 Stanley Rd, Winthrop, ME 04364
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  /36

  $232,500 Sold Sep 30, 2025

  • 960 Sq Ft
  • $242/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1976

  21 Pamela Dr, Winthrop, ME 04364

  Welcome to easy living in this well-landscaped, single-level home nestled in a desirable and peaceful Maine neighborhood. Offering three bedrooms, this home features a nice layout, perfect for families, retirees, or anyone looking for convenience and comfort on one floor.Enjoy crisp Maine evenings with the warmth of a wood stove, or relax outside on the large back deck overlooking a private,

  Nicole Coward Fontaine Family-The Real Estate Leader

  

  21 Pamela Dr, Winthrop, ME 04364
• 

  

  /35

  Est $444,435 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft

  310 Route 41, Winthrop, ME 04364

  

  310 Route 41, Winthrop, ME 04364
• 

  

  /76

  $269,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  30 Birch St, Winthrop, ME 04364

  This 3 bedroom 1 bath home has been in the same family for 52 years. It sits on 2 intown acres, but has a country feel. The property is on a quiet dead end street. There is a brook that runs through the property and the water helps to feed the blueberry and blackberry bushes, along with some apple trees and many more plantings. There is a Sun Mate solar panel that allows free energy from the sun

  Dylan Armstrong Sprague & Curtis Real Estate

  

  30 Birch St, Winthrop, ME 04364
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  /18

  $30,000 Sold Sep 29, 2025

  • 924 Sq Ft
  • $32/SF
  • 13 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  26 Squire Ct, Winthrop, ME 04364

  Renovated 1988 mobile home with 3 bedrooms and 1.5 baths in a peaceful central Maine setting. Move-in ready with fresh paint, new flooring, new toilets, and new interior doors. Finalize hooking up the pellet stove for an even cozier atmosphere in the upcoming fall and winter months. Affordable, comfortable living in a convenient central Maine location - come see for yourself! Pets are allowed.

  Karen Edgcombe Maine Real Estate Co

  

  26 Squire Ct, Winthrop, ME 04364

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