$551,900
- 2 Beds
- 2 Baths
- 1,344 sqft (on 22.71 acres)
285 Roosevelt Trail, Windham, ME 04062
Est. Refi. Payment $3,419/mo*
Refinance Your HomeCurrently Off Market - Sold Feb 10, 2025 for $525,000
Home Value
Trulia Estimate
$552KSince last month
Increased$5K (+0.9%)Since last year
Increased$44K (+8.7%)Since last sale
Increased$28K (+5.3%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +116% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $553K |
| August 2026 | $548K |
| July 2026 | $547K |
| June 2026 | $547K |
| May 2026 | $543K |
| April 2026 | $541K |
| March 2026 | $531K |
| February 2026 | $520K |
| January 2026 | $501K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.34 | Single-Family Home | $889,000 | 05/15/26 | 2 | 2 | 2,976 | |
0.34 | Single-Family Home | $800,000 | 01/30/26 | 3 | 2.5 | 2,232 | |
0.23 | Single-Family Home | $735,000 | 12/29/25 | 4 | 2.5 | 2,246 | |
0.68 | Single-Family Home | $575,000 | 05/07/26 | 3 | 2.5 | 1,866 | |
0.84 | Single-Family Home | $570,740 | 05/13/26 | 3 | 2 | 1,594 | |
0.71 | Single-Family Home | $440,000 | 06/25/26 | 3 | 1 | 1,536 | |
0.71 | Single-Family Home | $450,000 | 12/04/25 | 3 | 1 | 1,813 | |
0.90 | Single-Family Home | $510,000 | 07/10/26 | 4 | 2 | 1,790 | |
0.85 | Single-Family Home | $680,000 | 07/10/26 | 3 | 2 | 2,639 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.18 | $615,300 | 4 | 2 | 2,100 | Off Market | |
0.23 | $735,000 | 4 | 2.5 | 2,246 | Recently Sold | |
0.28 | $475,500 | 2 | 1 | 1,168 | Off Market | |
0.34 | $800,000 | 3 | 2.5 | 2,232 | Recently Sold | |
0.34 | $889,000 | 2 | 2 | 2,976 | Recently Sold | |
0.36 | - | - | - | - | Off Market | |
0.39 | $616,000 | 3 | 2.5 | 3,217 | For Sale | |
0.42 | $306,100 | 3 | 1 | 1,152 | Off Market | |
0.38 | $615,400 | 3 | 2 | 1,772 | Off Market | |
0.43 | $560,100 | 3 | 2 | 1,820 | Off Market | |
0.41 | $569,000 | 4 | 2 | 2,016 | For Sale |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1997
22.71 acre lot
1,344 sqft
$411/sqft
Garage
Last check for updates: about 12 hours ago
Listed by Client First Realty Maine
Bought with: Keller Williams Realty
Source: Maine Listings, MLS#1612412

About this House
What's unique:Cleared back lotWide wrap around drivewayLots of storage
Come Enjoy Country Living while being minutes from the City or Discover the Potential for Business Use!! This 1997 Ranch With Detached 3 Level/2 Car Garage is Situated on 22.71 Acres in Windham ME and is Only Minutes Away from Portland!! This Property is Set up as 2 Separate Lots in the C-3 Zone With Possible Potential for Development!! The Home and Property Features Include: Wide Wrap around Driveway with Cleared Back Lot, Lots of Storage, Woodstove, Decks and a Large Primary Bedroom with Bath! Do Not Miss Out on this Property!!
285 Roosevelt Trail, Windham, ME 04062 is a 2 bedroom, 2 bathroom, 1,344 sqft single-family home built in 1997. It last sold for $525,000 on Feb 10, 2025 (5% above the $499,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $551,900, with a rent estimate of $2,733/month.
Home Details for 285 Roosevelt Trail
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Interior Details Basement: Interior Entry,Full,Sump Pump,UnfinishedNumber of Rooms: 4Types of Rooms: Primary Bedroom, Bedroom 1, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 1344 Square Feet |
Appliances & Utilities Appliances: Dryer, Electric Range, Refrigerator, WasherDryerRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa No Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Laminate, Vinyl |
Levels, Entrance, & Accessibility Floors: Carpet, Laminate, Vinyl |
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Exterior Home Features Roof: ShinglePatio / Porch: DeckOther Structures: Shed(s)No Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Gravel,5 - 10 Spaces,Detached,Storage |
Frontage Road Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Private Sewer |
Finished Area Finished Area (above surface): 1344 Square Feet |
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Year Built Year Built: 1997 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Raised Ranch,Ranch |
Building Construction Materials: Wood Frame, Vinyl Siding |
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Price List Price: $499,000 |
Status Change & Dates Off Market Date: Sat Jan 18 2025 |
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MLS Status: Closed |
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Direction & Address City: Windham |
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Building Area Building Area: 1344 Square Feet |
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Lot Area: 22.71 Acres |
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BasementMls Number: 1612412Above Grade Unfinished Area: 1344 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Feb 10, 2025 Source: Maine Listings #1612412 | Sold | $525,000 |
Jan 18, 2025 Source: Maine Listings #1612412 | Pending | $499,000 |
Jan 13, 2025 Source: Maine Listings #1612412 | Listed For Sale | $499,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $5,284 | $460,700 |
Home facts updated by county records
Market trends in Windham
Last updated August 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
96
22MoM
Around this home
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections

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.
ยฉ 2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Frequently asked questions about 285 Roosevelt Trail
- What is 285 Roosevelt Trail estimated to be worth?Trulia's estimated value for 285 Roosevelt Trail in Windham, ME is $551,900.
- What is the price history for 285 Roosevelt Trail?285 Roosevelt Trail in Windham, ME last sold for $525,000 in February 2025.
- Is Windham a buyer's or seller's market?Windham is currently a seller's market, based on recent for-sale activity.
- What do residents say about Windham?Residents describe Windham, ME as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Windham, ME.
- Does 285 Roosevelt Trail have laundry facilities?Yes, 285 Roosevelt Trail in Windham, ME has in-unit laundry.
- How big is the lot at 285 Roosevelt Trail?The lot at 285 Roosevelt Trail in Windham, ME is about 22.7 acres.

