392 Roosevelt Trl, Windham, ME 04062
Property image
Property image
OFF MARKET

$312,300

Trulia Estimate
as of Sep 18, 2026
  • 1 Bed
  • 1 Bath
  • 608 sqft

392 Roosevelt Trl, Windham, ME 04062

Home Highlights

Single-Family Home
608 sqft
$514/sqft

Local Information

  • Map ViewExplore the area around 392 Roosevelt Trl.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Cozy 1 bed 1 bath home located off 302 offering convenient travel to major towns and destination areas such as Portland, Windham, Westbrook, Sebago Lakes, Falmouth and more. Alot of local amenities close by! Home is equipped with a water filtration/softener system and heats with propane monitor heater. This property is available for rent now. No smoking. Tenant pays their own utilities. There is a washer/dryer hook up in the basement.

Owner is responsible for their own utilities, yard maintenance, and snow removal. No Smoking. Off street parking in private driveway. Property management company available for maintenance calls. Pets by permission. Pet fee is 1x non refundable fee. $250 per cat or $500 for dog.
392 Roosevelt Trl, Windham, ME 04062 is a 1 bedroom, 1 bathroom, 608 sqft single-family home. It last sold for $35,000 on Aug 1, 2003 (1,742% above the $1,900 asking price). More recently, it was listed as a rental in April 2026 with an asking price of $1,900 per month. That rental listing was removed on April 9, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $312,300, with a rent estimate of $1,814/month.

Home Details for 392 Roosevelt Trl

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Appliances & Utilities
MicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Exterior Home Features
Lawn
Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 392 Roosevelt Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
402 Roosevelt Trail, Windham, ME
0.07
Single-Family Home
$330,000
07/29/26
2
1
878 sqft
38 Lotts Dr, Windham, ME
0.34
Single-Family Home
$200,000
04/27/26
4
1
1,410 sqft
81 Hall Road, Windham, ME
0.38
Single-Family Home
$435,000
03/02/26
4
1
1,429 sqft
72 Hall Rd, Windham, ME
0.41
Single-Family Home
$725,000
07/13/26
3
3
2,059 sqft
265 Windham Center Road, Windham, ME
0.85
Single-Family Home
$440,000
06/25/26
3
1
1,536 sqft
15 Harding Drive, Windham, ME
0.46
Single-Family Home
$699,900
11/13/25
3
2.5
2,578 sqft
306 Roosevelt Trl, Windham, ME
0.97
Single-Family Home
$405,000
01/21/26
2
2
912 sqft
577 Gray Road, Windham, ME
0.63
Single-Family Home
$565,000
10/15/25
3
2.5
1,908 sqft
70 Nash Road, Windham, ME
0.80
Single-Family Home
$595,000
06/05/26
3
2
1,810 sqft
2 Homestead Lane, Windham, ME
0.87
Single-Family Home
$510,000
07/10/26
4
2
1,790 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Windham

Last updated Sep 2026
Trulia Rent Estimate$1,814/mo
Average rent
$2.3K
Available listings
37
View rental market trends in Windham, ME

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.
  • Charliestandishjr
    "There are lots of dogs in the neighborhood . Everyone’s welcome and pets are always welcomed here. And everyone picks up their dogs pop"
    0
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  • Charliestandishjr
    "It’s a good place to live . I feel safe in my neighborhood. My neighbors are all friendly .They’re is enough stores in town that I don’t have to go to Portland "
    0
    Flag
  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
    0
    Flag
  • Geri Post
    "My wonderful neighbors very helpful. Look out for each other and consider ourselves family quiet neighborhood and nice area surrounding trees and a pool"
    0
    Flag
  • Jeannine M.
    "Great area for kids and easy to get to Portland for nightlife or the Mountains for skiing. There's farmer's markets and maple sugar farms, and many deer. If you have kids this is a great place to live where they can ride bikes or play in the lake. "
    1
    Flag
  • Jess I.
    "Many of the people in my neighborhood enjoy the outdoors. We live on the Presumscot River so we have all kinds of wildlife, many enjoy water sports like kayaking, paddle boarding, boating, fishing, and you see them out and about. We also have close access to the Mt. Division trail which is great for everyone, including Fido, as long as they are on a leash. There are farmers markets, lots of shopping, restaurants and sea coast fun park. Just go 5miles up the road. Or the Highschool has sports fields, an outdoor track, a rock climbing wall inside through adult Ed I think? Windham is a great place to be."
    0
    Flag
  • Katie
    "no public transport. good areas and bad. dog friendly. side roads do not get taking care of well in winter months . nice trails for walking. not a very well known going out town most people still travel to portland for drinks with friends dancing ect. "
    13
    Flag
  • Lizmc200
    "I love everything about Windham. The people are great and the town has everything you need in it. "
    0
    Flag
  • Laura C.
    "One way in and one way out. Not a lot of traffic or random drive throughs. Quiet, nice neighborhood with lots of friendly faces."
    2
    Flag
  • Jennilee M.
    "Quiet and friendly, I love this neighborhood. There are Lots of kids around with pets in the area. Everyone looks out for one another "
    1
    Flag
  • zmbailey
    "If you don't have a car, do not move here. Air is relatively clean though."
    0
    Flag
  • Julie L. D.
    "I live two streets from Carmichael and love living so close to the lakes and less than twenty minutes to Portland! The schools are within a 5-7 minute drive and shopping is less than three miles down the road. You can avoid the traffic by taking the backroads, that lead into outer Washington Ave or travel down the road to enter the Maine Turnpike just down the street in Gray. I love listening to the loons on the lake, early Spring into the Fall, and it is always fun to watch the fireworks show on the lake July 4th, put on by neighbors all around the lake! With the snowmobile trails so close by, I can hop on my sled, ice fishing, ice skate, or boat all outside my front door! This is a great area to retire, or raise a family"
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Apr 9, 2026
Source: Zillow Rentals
ListingRemoved
$1,900
Apr 1, 2026
Source: Zillow Rentals
Listed For Rent
$1,900
Jan 25, 2024
Source: Zillow Rentals
ListingRemoved
Jan 14, 2024
Source: Zillow Rentals
Listed For Rent
$1,750
Aug 1, 2003
Source: N/A
Sold
$35,000

Frequently asked questions about 392 Roosevelt Trl

  • What is 392 Roosevelt Trl estimated to be worth?
    Trulia's estimated value for 392 Roosevelt Trl in Windham, ME is $312,300.
  • What is the price history for 392 Roosevelt Trl?
    392 Roosevelt Trl in Windham, ME last sold for $35,000 in August 2003.
  • 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 392 Roosevelt Trl have parking?
    Yes, 392 Roosevelt Trl in Windham, ME has on-site parking.

Homes for rent near 392 Roosevelt Trl

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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