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$359,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 2 Beds
  • 1 Full Bath
  • 972 Sq. Ft.
  • 0.34 Acres
  • Updated 8 days ago
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Tucked away on a quiet dead-end road, this charming two-bedroom cottage-style home offers the perfect blend of comfort, privacy, and year-round enjoyment. Thoughtfully and completely remodeled, the home features a warm, welcoming layout filled with natural light and cozy finishes throughout. Unwind in the four-season porch while taking in peaceful winter water views, or enjoy an easy stroll to nearby Highland Lake access-perfect for boating, kayaking, swimming, and summer days on the water. When winter arrives, Highland Lake transforms into a hub for ice fishing and seasonal fun, making this a true four-season retreat. Whether you're seeking a serene weekend getaway or a low-maintenance year-round residence, this home delivers. With close proximity to Portland, you'll love the balance of peaceful lakeside living without sacrificing convenience. A rare opportunity to own a move-in-ready lake-area cottage that checks every box.

Full Property Details for 50 Overlook Rd

General

  • Price: $359,000
  • HOA FEE: $33/month
  • HOA FEE FREQ.: Annually
  • Taxes: $3,077 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MREIS
  • MLS ID: 1648639
  • Updated: 1/9/2026
  • Added to Site: 12 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: 1st Floor Bedroom, Bathtub, One-Floor Living
  • Flooring: Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry - 1st Floor, Main Level

Parking

  • Parking Features: 1 - 4 Spaces, Other, Off Street

Location

  • County: Cumberland
  • Subdivision: Overlook Road Association

Community

  • Association: Yes

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Other, Baseboard

Utilities

  • Sewer: Septic Tank, Private Sewer
  • Water: Well, Private
  • Well: Yes

Structural Information

  • Architectural Style: Camp, Cottage, Ranch
  • Construction: Vinyl Siding, Wood Frame
  • Roof: Fiberglass, Shingle
  • Building Size: 972
  • Square Feet: 972
  • Sq. Ft. Source: Public Records
  • Living Area: 972 Sq. Ft.
  • Finished Total: 972 Sq. Ft.
  • Finished Above Grnd: 972 Sq. Ft.
  • Year Built: 1935

Lot Features

  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 14,810.4
  • Lot Size Source: Public Records
  • Zoning: FR
  • Lot Description: Open, Corner Lot, Level, Neighborhood, Subdivided

Water Features

  • Water Front: Yes

Financial Considerations

  • Association Fee: $400
  • Assoc Fee Freq.: Annually
  • Tax Amount: $3,077
  • Tax Year: 2024

Disclosures and Reports

  • Lot Number: 65

Listed by A Team Realty (207) 894-8484

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Listing agent

— 50 Overlook Rd —

  • A Team Realty

    207-894-8484

info@ateammaine.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 50 Overlook Rd

School District:Regional School Unit 14
NameGradesDistance
Windham Primary School
404 Gray Road, Windham, ME 04062
K-32.3 mi
Manchester School
709 Roosevelt Trail, Windham, ME 04062
4-54.7 mi
Windham Middle School, Windham, ME
408 Gray Road, Windham, ME 04062
6-82.2 mi
Windham High School, Windham, ME
406 Gray Road, Windham, ME 04062
9-122.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 50 Overlook Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/06/2026
Listed
$359,000
115.62%
MLS
6/16/2025
Sold
$166,500
—
Public Record
Get Price Alerts and Save Property
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 for 50 Overlook Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$3,077
9%
$268,300
6%
2023
$2,831
14%
$252,800
18%
2022
$2,493
6%
$214,700
15%
2021
$2,356
—
$187,000
21%
2021
$2,356
4%
$154,600
—
2019
$2,263
8%
$154,600
12%
2018
$2,087
9%
$137,500
18%
2017
$1,917
5%
$116,700
—
2016
$1,832
4%
$116,700
—
2015
$1,768
3%
$116,700
—
2014
$1,712
2%
$116,700
—
2013
$1,686
—
$116,700
—
View All
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 for 50 Overlook Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by A Team Realty (207) 894-8484

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50 Overlook Road, Windham, ME 04062 (MLS# 1648639) is a Single Family property with 2 bedrooms and 1 full bathroom. 50 Overlook Road is currently listed for $359,000 and was received on January 06, 2026. Want to learn more about 50 Overlook Road? Do you have questions about finding other Single Family real estate for sale in Windham? You can browse all Windham real estate or contact a Coldwell Banker agent to request more information.

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