20 Bailey Dr, Windham, ME 04062
OFF MARKET

20 Bailey Dr
Windham, ME 04062

  • 3 Beds
  • 1 Bath
  • 1,344 sqft (on 1.84 acres)

$453,200

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $2,647/mo*
Refinance Your Home

$453,200

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $2,647/mo*
Refinance Your Home
3 Beds
1 Bath
1,344 sqft
(on 1.84 acres)

Homes for sale near 20 Bailey Dr

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Wonderful open concept one level living. Well maintained and all good sized rooms, extra large bathroom with walk in shower, freshly painted interior, located at end of the road with new homes being built. Large lot with good privacy and buffer from neighbors. Partially finished rooms in basement provide additional gathering space and workout area. Enjoy the spacious deck overlooking wooded back yard. Less than 6 miles to all of Windham's amenities or just a mile to Westbrook line and easy commute to Portland. Tucked away yet so convenient.
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.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20 Bailey Dr

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: OilHeating Fuel: Oil

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.84 acres

Price History for 20 Bailey Dr

DatePriceEventSource
11/02/2018$238,000Sold
Maine Listings #1372322
10/05/2018$228,000PendingAgent Provided
10/01/2018$228,000Listed For SaleAgent Provided
03/28/2012$139,000Sold
Maine Listings #1035222
11/15/2011$139,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$4,866
Assessment$424,200
Home facts updated by county records

Comparable Sales for 20 Bailey Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
212 Chute Rd, Windham, ME
0.62
Single-Family Home
$250,000
10/10/25
3
1
1,225
42 Johnson Road, Windham, ME
0.48
Single-Family Home
$515,000
10/24/25
3
2
1,778
73 Pope Road, Windham, ME
0.61
Single-Family Home
$549,000
09/03/25
3
2
1,746
46 Highland Cliff Road, Windham, ME
0.85
Single-Family Home
$401,000
08/22/25
3
1
1,203
58 Albion Road, Windham, ME
0.91
Single-Family Home
$325,000
09/12/25
3
1
1,793
7 Haven Road, Windham, ME
0.55
Single-Family Home
$565,000
02/24/26
3
3
1,792
369 Windham Center Road, Windham, ME
0.81
Single-Family Home
$471,500
08/13/25
3
1.5
1,724
210 Chute Road, Windham, ME
0.63
Single-Family Home
$360,000
06/10/25
2
1.5
1,225
48 Albion Road, Windham, ME
0.89
Single-Family Home
$450,000
12/04/25
3
1
1,813
17 Hemon Cobb Road, Windham, ME
0.52
Single-Family Home
$655,000
06/17/25
3
2.5
1,887

Assigned Schools

These are the assigned schools for 20 Bailey Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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"
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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
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  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • zmbailey
    "If you don't have a car, do not move here. Air is relatively clean though."
    0
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  • 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"
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Homes for rent near 20 Bailey Dr

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Off Market Homes Near 20 Bailey Dr

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Explore by feature

20 Bailey Dr, Windham, ME 04062 is a 3 bedroom, 1 bathroom, 1,344 sqft single-family home built in 1996. This property is not currently available for sale. 20 Bailey Dr was last sold on Nov 2, 2018 for $238,000. The current Trulia Estimate for 20 Bailey Dr is $453,200.