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Cale Roberts
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20 Court Street, Winslow, ME 04901

$375,000
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Pending
BEDS2 BATHS2 full SQUARE FEET2,752 MLS#1659684
STATUSPending PROPERTY TYPEResidential - Single Family

Property Description

13088 - Welcome to 20 Court Street, nestled in Winslow's sought-after Smiley Acres neighborhood -- a home where warmth, comfort, and thoughtful design come together beautifully. Set on a quiet dead-end street, this meticulously maintained ranch invites you in from the moment you arrive, with colorful flower gardens framing the home, an inviting front porch perfect for morning coffee, and the kind of area where neighborly waves and evening conversations still exist. Step inside and feel instantly at home in the sun-filled open-concept kitchen and dining area, thoughtfully designed for everyday living and effortless entertaining. Just beyond, the spacious living room centers around a cozy built-in propane stove with rich wood mantle -- the perfect place to gather on cool Maine evenings. The first floor offers a generous primary bedroom retreat, a beautifully appointed bath with corner soaking tub, stand-up shower and double vanities, plus a second bedroom for guests or family. Down the wood staircase, the finished lower level opens a world of possibilities. Completely refinished with a full system by TC Hafford Basement Systems, including waterproof wainscoting half walls and poured concrete floors, this space is ideal for a family room, game room, or cozy den. A bonus room offers flexibility for an office, hobby room or additional bedroom, alongside a second full bath (to be completed before closing) and dedicated laundry room. Outside, enjoy an expansive two-car attached garage, paver patio, and open backyard ready for gardens, gatherings, and play -- a truly special place to call home.

20 Court Street | MLS# 1659684

This single family home located at 20 Court Street, Winslow, ME 04901 is currently listed for sale with an asking price of $375,000. This property was built in 1996 and has 2 bedrooms and 2 full baths with 2752 sq. ft. Search Winslow real estate on caleroberts.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Interior, Finished, Full
Cooling: Heat Pump
Garage: 2 car attached
Heating: Other, Heat Pump, Baseboard
Home Style: Ranch
Lot Size: 0.58 Acres
Roof Type: Shingle
Taxes: $4,361
Year Built: 1996

Feature Descriptions

Amenities: 1st Floor Bedroom, Bathtub
Appliances: Refrigerator, Electric Range, Dryer, Dishwasher
Electric: Circuit Breakers
Exterior: Vinyl Siding, Wood Frame
Flooring: Tile, Laminate, Concrete
Foundation: Concrete Perimeter
Lot: Well Landscaped, Open, Level, Sidewalks, Interior Lot, Intown, Neighborhood, Subdivided
Parking: Storage Above,5 - 10 Spaces, Paved, Inside Entrance
Road Surface: Paved
Sewer: Private Sewer
SQ FT Above Grade: 1376
SQ FT Below Grade: 1376
Total Rooms: 9
Water: Private

Listed By / Shown By

Listed By

Agency Name: Allied Realty
Agent Name: Chelsea VanGorden
Agency Phone: 207-474-9553

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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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Estimated Payment

$ 1,307.38 per month $834.59 Principal & Interest $363.42 Property Tax $109.38 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 06/08/2026. The listing information on this page last changed on 06/08/2026. 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 Mon 06/08/2026 11:53:11 AM EST) or MLSPIN MLS (last updated Mon 06/08/2026 11:50:40 AM EST) or Prime MLS (last updated Mon 06/08/2026 11:46:31 AM EST) or MREIS (last updated Mon 06/08/2026 11:45:44 AM 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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Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


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