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.
Single-familyProperty Type
1935Year Built
0.34 acresLot Size
$358Est. Price/Sq.Ft.
1 spaceParking
Listed by Ashley Fearon• A Team Realty
Contact: info@ateammaine.com
Bought with Alicia Frechette Ramsey Pulkkinen• A Team Realty
Investors! Here is an opportunity to renovate this home or build a new with deeded access to Highland Lake. Home is in need of extensive repairs.
Year
Property tax
Land + Additions
Assessment*
2025
$2,539 (−17.5%)
$106,300 + $104,200
$210,500
2024
$3,077 (+8.7%)
$106,300 + $162,000
$268,300
2023
$2,831 (+13.6%)
$98,800 + $154,000
$252,800
2022
$2,493 (+5.8%)
$77,900 + $136,800
$214,700
2021
$2,356 (+1.6%)
$67,800 + $119,200
$187,000
2020
$2,319 (+2.5%)
$59,400 + $95,200
$154,600
2019
$2,263 (+8.4%)
$59,400 + $95,200
$154,600
2018
$2,087 (+8.9%)
$53,500 + $84,000
$137,500
2017
$1,917 (+4.6%)
$48,000 + $68,700
$116,700
2016
$1,832 (+3.6%)
$48,000 + $68,700
$116,700
2015
$1,768 (+3.3%)
$48,000 + $68,700
$116,700
2014
$1,712
$48,000 + $68,700
$116,700
Tax history for 50 Overlook Rd
Year
Property tax
Land + Additions
Assessment*
2025
$2,539 (−17.5%)
$106,300 + $104,200
$210,500
2024
$3,077 (+8.7%)
$106,300 + $162,000
$268,300
2023
$2,831 (+13.6%)
$98,800 + $154,000
$252,800
2022
$2,493 (+5.8%)
$77,900 + $136,800
$214,700
2021
$2,356 (+1.6%)
$67,800 + $119,200
$187,000
2020
$2,319 (+2.5%)
$59,400 + $95,200
$154,600
2019
$2,263 (+8.4%)
$59,400 + $95,200
$154,600
2018
$2,087 (+8.9%)
$53,500 + $84,000
$137,500
2017
$1,917 (+4.6%)
$48,000 + $68,700
$116,700
2016
$1,832 (+3.6%)
$48,000 + $68,700
$116,700
2015
$1,768 (+3.3%)
$48,000 + $68,700
$116,700
2014
$1,712
$48,000 + $68,700
$116,700
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
2
Baths
1
Stories
1
Lot width
—
Lot depth
—
Lot size
0.34 Acres
Year renovated
—
Sq. Ft.
972
Year built
1935
Style
Single Family Residential
County
Cumberland County
APN
141447
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 27, 2026.
FR
Farm-Residential District
The Town, as a rapidly growing community, recognizes that certain areas of the town will experience residential growth while the basic rural agricultural orientation remains. It is the intent of this chapter to allow these uses to coexist and develop harmoniously.
Permitted uses
Include but are not limited to:
Agriculture
Religious facility
Housing-Single unit
Housing-Multiple units
Public service
Golf related
Kennel
Communications tower
Cemetery
Property details
Parking
Parking Information
Parking Features: 1 - 4 Spaces, Off Street
Interior
Bathroom Information
# of Baths (Full): 1
Room 1 Information
Type: Laundry
Level: First
Room 2 Information
Type: Bedroom 1
Level: First
Room 3 Information
Type: Dining Room
Level: First
Room 4 Information
Type: Kitchen
Level: First
Room 5 Information
Type: Living Room
Level: First
Room 6 Information
Type: Bedroom 2
Level: First
Basement Information
Basement Entry: Dirt Floor, Crawl Space
Interior Features
# of Rooms: 6
Interior Features: 1st Floor Bedroom, Bathtub, One-Floor Living
Flooring: Vinyl
Laundry Information
Laundry Features: 1st Floor Laundry, Main Level
Exterior
Building Information
Construction Materials: Vinyl Siding, Wood Frame
Roof: Fiberglass, Shingle
Total Building Area (Sq. Ft.): 972
Building Area Source: Public Records
Property Information
Property Sub Type: Single Family Residence
Year Built: 1935
Above-Grade Finished Area (Sq. Ft.): 972
Lot Information
Lot Size (Sq. Ft.): $14,810.40
Lot Size (Acres): 0.34
Lot Size Source: Public Records
Lot Features: Open, Corner Lot, Level, Neighborhood, Subdivided
Road Surface Type: Gravel, Dirt
Zoning: FR
Waterfront Information
Waterfront: Yes
Water Body Name: Highland Lake
Water Body Type: Lake
Water View: Seasonal
Subdivision Information
Subdivision Name: Overlook Road Association
Financial
Tax Information
Annual Tax Amount: $3,077
Tax Year: 2024
Utilities
Utility Information
Has Heating
Heating: Baseboard
Electric: Circuit Breakers
Sewer: Septic Tank, Private Sewer
Utilities On: No
Water Source: Well, Private
Water Heater: Electric
Location
HOA Information
Has Association
Association Fee: $400
Association Fee Frequency: Annually
Location Information
Unparsed Address: 50 Overlook Road, Windham, ME 04062
Directions: Albion Rd to Overlook. Follow Overlook down towards Highland Lake and home will be on your left.
Public facts
Beds: 2
Baths: 1.0
Sq. Ft.: 972
Stories: 1.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1935
Year Renovated: —
County: Cumberland County
APN: 141447
Home facts updated by county records on Jul 27, 2026
Around this home
Schools
Windham Primary School
Public K-3 • Assigned • 2.3mi
5/10
Windham Middle School
Public 6-8 • Assigned • 2.2mi
4/10
Windham High School
Public 9-12 • Assigned • 2.3mi
6/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 91° expected this year, 16 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Windham, ME • 04062
Average low and high temperatures (°F)
28
13
32
13
44
27
54
36
64
47
76
57
81
62
78
58
73
51
61
41
48
32
34
18
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.4 hours in
June and 4.2 hours in December, placing it below the
U.S. average for solar exposure.
8.4 hrs
4.2 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$331,000 – $401,000
Reach more buyers when you sell with Redfin. Save up to $3,479 in fees.3 minutes to get started.
Get a free, detailed breakdown of how we calculated your estimate.