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Cale Roberts
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64 Annabessacook Drive, Winthrop, ME 04364

$515,000
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BEDS3 BATHS1 full 1 partial SQUARE FEET2,136 MLS#1659788
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWinthrop Public Schools

Property Description

This is the kind of property people wait for--and rarely find.Set on 7.7 private acres just minutes from downtown Winthrop, this property offers space, flexibility, and access to Annabessacook Lake without paying waterfront taxes.Keep your boat on the lake, head out for a last-minute sunset cruise, and come back to your own private setting. No hauling, no hassle, no waterfront tax bill.The large barn adds another layer most homes simply do not offer--ideal for storing recreational equipment, projects, gatherings, or creating additional usable space beyond the home itself.Inside, the home offers multiple living areas, including a bright sitting area off the kitchen, an open-concept living room with pellet stove insert, and a finished lower level currently used as a family room and gym. Recent improvements include a remodeled bathroom, updated sitting area, finished basement space, kitchen shelving upgrades, tree removal to improve safety and usable yard space, and a recently replaced roof.Major infrastructure updates are also being completed by the seller, including a new septic system and water treatment improvements, giving buyers confidence in some of the property's most important long-term systems.Outside is where this property truly stands apart--privacy, usable acreage, hot tub, and lake access combine to create a lifestyle that is increasingly difficult to find in this area.If you've been looking for land, storage, flexibility, and access to the water without the cost of waterfront ownership, this is a property worth seeing in person.

64 Annabessacook Drive | MLS# 1659788

This single family home located at 64 Annabessacook Drive, Winthrop, ME 04364 is currently listed for sale with an asking price of $515,000. This property was built in 1973 and has 3 bedrooms and 1 full and 1 partial baths with 2136 sq. ft. Annabessacook Drive is located within the Winthrop Public Schools school district. Search Winthrop real estate on caleroberts.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Doghouse, Interior Entry, Walk-Out Access, Full
Cooling: Window Unit(s)
Garage: 2
Heating: Oil, Wood, Hot Water, Pellet Stove
Home Style: Raised Ranch
Lot Size: 7.70 Acres
Roof Type: Shingle
Taxes: $5,398
Year Built: 1973

Feature Descriptions

Amenities: Animal Containment System, Hot Tub, Laundry - Hookup, Shower
Appliances: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer
Electric: Circuit Breakers
Equipment: Cable, Internet Access Available
Exterior: Wood Frame, Vinyl Siding
Flooring: Other, Vinyl, Engineered Hardwood
Foundation: Poured Concrete
Lot: Near Country Club, Near Public Beach, Neighborhood, Level, Open Lot, Landscaped, Wooded
Parking: Paved,5 - 10 Spaces, Garage Door Opener, Inside Entrance, Storage
Road Surface: Paved
Sewer: Private Sewer, Septic Tank
Special View Info: Scenic
SQ FT Above Grade: 1461
SQ FT Below Grade: 675
Total Rooms: 9
Water: Private, Well
Water Body Name: Annabessacook Lake
Wooded: Yes

Local Schools

School District: Winthrop Public Schools

Listed By / Shown By

Listed By

Agency Name: NextHome Northern Lights Realty
Agency Contact: Office@NextHomeNLR.com
Agent Name: Heidi Libby

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Shown By

Agent Name: Cale Roberts
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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$ 1,746.21 per month $1,146.17 Principal & Interest $449.83 Property Tax $150.21 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/12/2026. The listing information on this page last changed on 06/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 06/12/2026 12:00:58 AM EST) or MLSPIN MLS (last updated Thu 06/11/2026 11:38:53 PM EST) or Prime MLS (last updated Thu 06/11/2026 11:33:22 PM EST) or MREIS (last updated Thu 06/11/2026 11:55:26 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.



Listing data is derived in whole or in part from the Maine IDX & is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.© 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

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