50 Overlook Road
Windham, ME 04062
- 2 Beds
- 1 Bath
- 972 sqft (on 0.34 acres)
$365,000
Last Sold: Feb 6, 2026
2% over list $359K
$376/sqft
$365,000
Last Sold: Feb 6, 2026
2% over list $359K
$376/sqft
2 Beds
1 Bath
972 sqft
(on 0.34 acres)
Local Information
© Google
-- mins to
Last check for updates: about 8 hours ago
Listed by A Team Realty
Bought with: A Team Realty
Source: Maine Listings, MLS#1648639

Description
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.
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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from February 10, 2026
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
$33/Monthly
Price/Sqft
$376/sqft
Listed
148 days ago
Home Details for 50 Overlook Road
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MLS Status: Closed |
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Interior Details Number of Rooms: 6Types of Rooms: Bedroom 1, Bedroom 2, Dining Room, Kitchen, Laundry, Living Room |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1 |
Dimensions and Layout Living Area: 972 Square Feet |
Heating & Cooling Heating: Baseboard,OtherNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa No Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Vinyl |
Levels, Entrance, & Accessibility Floors: Vinyl |
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Exterior Home Features Roof: Fiberglass ShingleNo Private Pool |
Parking & Garage No CarportNo GarageNo Attached Garage |
Frontage WaterfrontOn Waterfront |
Water & Sewer Sewer: Private Sewer, Septic TankWater Body: Highland Lake |
Farm & Range Frontage Length: Waterfrontage: 60, Waterfrontage Shared: 60 |
Finished Area Finished Area (above surface): 972 Square Feet |
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Year Built Year Built: 1935 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Camp,Cottage,Ranch |
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Price List Price: $359,000Price Per Sqft: $376/sqft |
Status Change & Dates Off Market Date: Fri Jan 09 2026 |
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Direction & Address City: WindhamCommunity: Overlook Road Association |
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Building Area Building Area: 972 Square Feet |
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Has an HOAHOA Fee: $400/Annually |
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Lot Area: 0.34 acres |
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Mls Number: 1648639Attribution Contact: info@ateammaine.comAbove Grade Unfinished Area: 972 |
Price History for 50 Overlook Road
| Date | Price | Event | Source |
|---|---|---|---|
| 02/06/2026 | $365,000 | Sold | Maine Listings #1648639 |
| 01/10/2026 | $359,000 | Pending | Maine Listings #1648639 |
| 01/06/2026 | $359,000 | Listed For Sale | Maine Listings #1648639 |
| 06/25/2025 | $165,500 | Sold | Maine Listings #1618772 |
| 06/25/2025 | $240,000 | Pending | Maine Listings #1618772 |
| 05/07/2025 | $240,000 | Contingent | Maine Listings #1618772 |
| 05/06/2025 | $240,000 | PriceChange | Maine Listings #1618772 |
| 04/11/2025 | $250,000 | Listed For Sale | Maine Listings #1618772 |
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $3,077 |
| Assessment | $268,300 |
Home facts updated by county records
Comparable Sales for 50 Overlook Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $410,000 | 08/29/25 | 4 | 1 | 1,258 | |
0.53 | Single-Family Home | $380,500 | 05/14/26 | 2 | 1 | 1,404 | |
0.07 | Single-Family Home | $726,300 | 08/05/25 | 3 | 2 | 1,532 | |
0.50 | Single-Family Home | $417,500 | 08/11/25 | 3 | 1 | 1,200 | |
0.50 | Single-Family Home | $335,000 | 08/13/25 | 2 | 1 | 810 | |
0.58 | Single-Family Home | $315,000 | 11/07/25 | 2 | 1 | 772 | |
0.50 | Single-Family Home | $375,000 | 01/16/26 | 3 | 1 | 1,056 | |
0.24 | Single-Family Home | $400,000 | 01/07/26 | 3 | 1 | 1,938 | |
0.53 | Single-Family Home | $485,000 | 05/14/26 | 2 | 1 | 1,685 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 50 Overlook Road.
What Locals Say about Windham
At least 40 Trulia users voted on each feature.
96 % Say car is needed
91 % Say parking is easy
85 % Say yards are well-kept
80 % Say there's wildlife
79 % Say there's holiday spirit
78 % Say people would walk alone at night
67 % Say it's quiet
67 % Say they plan to stay for at least 5 years
67 % Say it's dog friendly
66 % Say neighbors are friendly
66 % Say kids play outside
31 % Say there are community events
28 % Say there are sidewalks
28 % Say it's walkable to restaurants
17 % Say streets are well-lit
13 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and 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. Equal Housing Opportunity.
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Homes for rent near 50 Overlook Road
50 Overlook Road, Windham, ME 04062 is a 2 bedroom, 1 bathroom, 972 sqft single-family home built in 1935. This property is not currently available for sale. 50 Overlook Road was last sold on Feb 6, 2026 for $365,000 (2% higher than the asking price of $359,000). The current Trulia Estimate for 50 Overlook Road is $373,700.

