20 Bailey Dr
Windham, ME 04062
- 3 Beds
- 1 Bath
- 1,344 sqft (on 1.84 acres)
3 Beds
1 Bath
1,344 sqft
(on 1.84 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1996
Lot Size
1.84 acres
Living Area
1,344 sqft
Price/Sqft
$337
Parking
Garage
About this House
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.
20 Bailey Dr, Windham, ME 04062 is a 3 bedroom, 1 bathroom, 1,344 sqft single-family home built in 1996. It last sold for $238,000 on Nov 2, 2018. It is currently off market. The Trulia Estimate is $453,500, with a rent estimate of $2,728/month.
Home Details for 20 Bailey Dr
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Interior Details BasementNumber of Rooms: 5 |
Heating & Cooling Heating: OilHeating Fuel: Oil |
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Exterior Home Features Roof: AsphaltDeckExterior: Other |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1996 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Units in Building: 1 |
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Lot Area: 1.84 acres |
Price History for 20 Bailey Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 11/02/2018 | $238,000 | Sold | Maine Listings #1372322 |
| 10/05/2018 | $228,000 | Pending | Agent Provided |
| 10/01/2018 | $228,000 | Listed For Sale | Agent Provided |
| 03/28/2012 | $139,000 | Sold | Maine Listings #1035222 |
| 11/15/2011 | $139,000 | Listed For Sale | Agent Provided |
Market trends in Windham
Last updated June 2026
Avg. sale price
$464K
Sale-to-List Price
—
Price per sq ft
$276
Available listings
68
12MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| 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 |
|---|---|---|---|---|---|---|---|
0.62 | Single-Family Home | $250,000 | 10/10/25 | 3 | 1 | 1,225 | |
0.66 | Single-Family Home | $423,500 | 06/29/26 | 3 | 1 | 1,218 | |
0.34 | Single-Family Home | $300,000 | 06/18/26 | 3 | 1 | 1,611 | |
0.48 | Single-Family Home | $515,000 | 10/24/25 | 3 | 2 | 1,778 | |
0.61 | Single-Family Home | $549,000 | 09/03/25 | 3 | 2 | 1,746 | |
0.85 | Single-Family Home | $401,000 | 08/22/25 | 3 | 1 | 1,203 | |
0.91 | Single-Family Home | $325,000 | 09/12/25 | 3 | 1 | 1,793 | |
0.55 | Single-Family Home | $565,000 | 02/24/26 | 3 | 3 | 1,792 | |
0.81 | Single-Family Home | $471,500 | 08/13/25 | 3 | 1.5 | 1,724 | |
0.49 | Single-Family Home | $565,000 | 06/22/26 | 5 | 2 | 2,209 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 20 Bailey Dr.
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
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Apartments for Rent
Homes for sale near 20 Bailey Dr
Off Market Homes Near 20 Bailey Dr
Frequently asked questions about 20 Bailey Dr
- What is 20 Bailey Dr estimated to be worth?Trulia's estimated value for 20 Bailey Dr in Windham, ME is $453,500.
- What is the price history for 20 Bailey Dr?20 Bailey Dr in Windham, ME last sold for $238,000 in November 2018.
- Is Windham a buyer's or seller's market?Windham is currently a seller's market, based on recent for-sale activity.
- What's the median sale price in Windham?The median sale price in Windham is $464K.
- How big is the lot at 20 Bailey Dr?The lot at 20 Bailey Dr in Windham, ME is about 1.8 acres.
- Does 20 Bailey Dr have a garage?Yes, 20 Bailey Dr in Windham, ME has a garage.

