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$375,000 Just Listed
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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.
Full Property Details
Full Property Details for 20 Court St
General
- Price: $375,000
- Taxes: $4,361 (2025)
- Status: Active
- Type: Single Family
- Source: MREIS
- MLS ID: 1659684
- Updated: 4/29/2026
- Added to Site: 1 day(s) ago
Interior
- Number of Rooms: 9
- Interior Features: 1st Floor Bedroom, Bathtub
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Refrigerator, Electric Range, Dryer, Dishwasher
- Flooring: Tile, Laminate, Concrete
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Exterior
- Porch/Patio/Deck: Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Parking Features: Storage Above, 5 - 10 Spaces, Paved, Inside Entrance
Location
- County: Kennebec
Community
- Pets Allowed: Yes
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Heat Pump
- Heating Type: Other, Heat Pump, Baseboard
Utilities
- Sewer: Private Sewer
- Water: Private
Structural Information
- Architectural Style: Ranch
- Construction: Vinyl Siding, Wood Frame
- Roof: Shingle
- Building Size: 2752
- Square Feet: 2,752
- Sq. Ft. Source: Measured
- Living Area: 2,752 Sq. Ft.
- Finished Total: 2,752 Sq. Ft.
- Finished Above Grnd: 1,376 Sq. Ft.
- Finished Below Grnd: 1,376 Sq. Ft.
- Year Built: 1996
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Lot Size (Acres): 0.58
- Lot Size (Sq. Ft.): 25,264.8
- Lot Size Source: Public Records
- Zoning: MR
- Lot Description: Well Landscaped, Open, Level, Sidewalks, Interior Lot, Intown, Neighborhood, Subdivided
Financial Considerations
- Tax Amount: $4,361.45
- Tax Year: 2025
Disclosures and Reports
- Lot Number: 99
Listed by Allied Realty (207) 474-9553
Get Pre-Approved Today
Schools
Schools serving 20 Court St
School District:Winslow
| Name | Grades | Distance |
|---|---|---|
Winslow Elementary School 285 Benton Avenue, Winslow, ME 04901 | PK-6 | 0.5 mi |
Winslow Junior High School 30 Danielson Street, Winslow, ME 04901 | 7-8 | 0.4 mi |
Winslow High School 20 Danielson Street, Winslow, ME 04901 | 9-12 | 0.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 20 Court St
Date
Details
Price
Change
Source
4/29/2026
Listed
$375,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 20 Court St
Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,781
—
$318,700
—
2023
$4,781
26%
$318,700
78%
2022
$3,788
25%
$178,700
2%
2021
$3,034
—
$175,200
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 20 Court St
20 Court Street, Winslow, ME 04901 (MLS# 1659684) is a Single Family property with 2 bedrooms and 2 full bathrooms. 20 Court Street is currently listed for $375,000 and was received on April 29, 2026. Want to learn more about 20 Court Street? Do you have questions about finding other Single Family real estate for sale in Winslow? You can browse all Winslow real estate or contact a Coldwell Banker agent to request more information.

