Pending

$359,000

50 Overlook Road, Windham, ME 04062

2beds

972sqft

Est.:

Single Family Residence

Built in 1935

0.34 Acres Lot

$359,800 Zestimate^®

$369/sqft

$33/mo HOA

What's special

Filled with natural lightQuiet dead-end roadCharming two-bedroom cottage-style homeWarm welcoming layoutFour-season porchPeaceful winter water viewsCozy finishes throughout

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.

32 days

235

14

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 2
Bathrooms: 1
Full bathrooms: 1

Bedroom 1

Level: First

Bedroom 2

Level: First

Dining room

Level: First

Kitchen

Level: First

Laundry

Level: First

Living room

Level: First

Heating

Baseboard, Other

Cooling

None

Features

Flooring: Vinyl
Has fireplace: No

Interior area

Total structure area: 972
Total interior livable area: 972 sqft
Finished area above ground: 972
Finished area below ground: 0

Property

Features

On waterfront: Yes
Body of water: Highland Lake
Frontage length: Waterfrontage: 60,Waterfrontage Shared: 60

Lot

Size: 0.34 Acres

Details

Parcel number: WINMM29B65
Zoning: FR

Construction

Type & style

Home type: SingleFamily
Architectural style: Camp,Cottage,Ranch
Property subtype: Single Family Residence

Materials

Roof: Fiberglass,Shingle

Condition

Year built: 1935

Utilities & green energy

Electric: Circuit Breakers
Sewer: Private Sewer, Septic Tank
Water: Private, Well

Community & HOA

Community

Subdivision: Overlook Road Association

HOA

Has HOA: Yes
HOA fee: $400 annually

Location

Region: Windham

Financial & listing details

Price per square foot: $369/sqft
Tax assessed value: $268,300
Annual tax amount: $3,077
Date on market: 1/6/2026

Estimated market value

$359,800

$342,000 - $378,000

$2,694/mo

Price history

Date	Event	Price
1/10/2026	Pending sale	$359,000$369/sqft
Source: Maine Listings #1648639 Report a problem
1/6/2026	Listed for sale	$359,000+116.9%$369/sqft
Source: Maine Listings #1648639 Report a problem
6/25/2025	Sold	$165,500-31%$170/sqft
Source: Maine Listings #1618772 Report a problem
6/25/2025	Pending sale	$240,000$247/sqft
Source: Maine Listings #1618772 Report a problem
5/7/2025	Contingent	$240,000$247/sqft
Source: Maine Listings #1618772 Report a problem