David Super
Tim Dunham Realty
(207) 610-7633
80 Total Sales
1 in Windham
$474,000 Price
Welcome to 23 Pennywhistle Drive, a beautifully designed contemporary farmhouse located in one of Windham's most desirable neighborhoods. Built in 2022 and thoughtfully crafted with both comfort and style in mind, this stunning home offers over 2,400 square feet of beautifully finished living space on a private 1+ acre lot. Inside, you'll find a bright and inviting open-concept layout filled with natural light, modern finishes, and quality craftsmanship throughout. The spacious kitchen flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. Luxury vinyl plank flooring, a cozy fireplace, and clean contemporary farmhouse design elements add warmth and character throughout the home. The home features three bedrooms, including a spacious primary suite complete with a private bath and custom built-ins in the closet. In addition to the bedrooms, there is a large bonus room above the garage offering flexible space for a media room, playroom, guest area, or home office. The walkout basement includes an additional bonus room and a convenient half bath, providing even more versatility and functionality. An expansive oversized three-door, four-car garage provides exceptional storage and workspace, perfect for vehicles, outdoor equipment, recreational gear, or hobby space. Designed for efficiency and convenience, the property also features solar panels and a full sprinkler system. Enjoy the peaceful setting while being just minutes from Westbrook, North Windham amenities, shopping, dining, lakes, outdoor recreation, and an easy commute to Portland. This nearly new home offers the perfect blend of modern farmhouse charm, efficiency, and convenience in the heart of Southern Maine.
Last Agent to Sell the Property
Better Homes & Gardens Real Estate/The Masiello Group Listed on: 05/16/2026
David Super
Tim Dunham Realty
(207) 610-7633
80 Total Sales
1 in Windham
$474,000 Price
Emily Shaffer
U&R Real Estate
(717) 913-5206
31 Total Sales
1 in Windham
$400,000 Price
Ashley Fearon
A Team Realty
(877) 780-5160
92 Total Sales
36 in Windham
$125K - $915K Price Range
Nova Tower
Waypoint Brokers Collective
(646) 971-8783
80 Total Sales
1 in Windham
$371,000 Price
Sonja Nielsen
EXP Realty
(888) 865-8841
19 Total Sales
1 in Windham
$291,000 Price
Gabrielle Herbig
Portside Real Estate Group
(207) 746-0532
19 Total Sales
1 in Windham
$503,000 Price
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/04/2026 08/04/26 | Sold | $835,000 | -1.8% | $292 / Sq Ft |
| 08/02/2026 08/02/26 | Pending | -- | -- | -- |
| 06/12/2026 06/12/26 | Price Changed | $849,900 | -2.9% | $298 / Sq Ft |
| 05/16/2026 05/16/26 | For Sale | $874,900 | -- | $306 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,573 | $710,900 | $160,200 | $550,700 |
| 2024 | $7,578 | $660,700 | $121,100 | $539,600 |
| 2023 | $6,975 | $622,800 | $119,300 | $503,500 |
| 2022 | $6,347 | $546,700 | $102,300 | $444,400 |
| 2021 | $1,040 | $82,500 | $82,500 | $0 |
| 2020 | $989 | $65,900 | $65,900 | $0 |
D
Seller's Agent in 2026
Daneel Dafni
Better Homes & Gardens Real Estate/The Masiello Group
(207) 751-7380
47 Total Sales
D
Buyer's Agent in 2026
Deborah Meek
Keller Williams Realty
(207) 831-8256
196 Total Sales
J
Buyer Co-Listing Agent in 2026
Jonathan Meek
Keller Williams Realty
(207) 879-9800
2 Total Sales
Source: Maine Listings
MLS Number: 1662103
APN: 6 25 15
Ask me questions while you tour the home.