Date
Details
Price
Change
Source
5/16/2026
Listed
$874,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$874,900 Just Listed
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Property Description
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.
Full Property Details
Full Property Details for 23 Pennywhistle Dr
General
- Price: $874,900
- HOA FEE: $21/month
- HOA FEE FREQ.: Annually
- Taxes: $8,573 (2025)
- Status: Active
- Type: Single Family
- Source: MREIS
- MLS ID: 1662103
- Updated: 5/17/2026
- Added to Site: 1 day(s) ago
Interior
- Number of Rooms: 7
- Interior Features: Bathtub, Pantry, Shower, Storage, Primary Bedroom w/Bath
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Washer, Refrigerator, Gas Range, Dryer, Dishwasher, Cooktop
- Flooring: Luxury Vinyl
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 2
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Washer Hookup
Additional Information
- Security/Safety: Sprinkler
- Equipment: Internet Access Available, Air Radon Mitigation System
Exterior
- Porch/Patio/Deck: Deck, Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking Features: Auto Door Opener, Paved, Inside Entrance, Tandem, 1 - 4 Spaces, Off Street, On-Site Parking
Location
- County: Cumberland
- Subdivision: Durant Homestead
Community
- Association: Yes
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Heat Pump
- Heating Type: Electric, Gas Bottled, Propane, Solar, Baseboard, Heat Pump, Hot Water, Other, Zoned
Utilities
- Sewer: Private Sewer, Septic Design Available, Septic Tank
- Water: Well
- Well: Yes
Structural Information
- Architectural Style: Modern, Farmhouse
- Construction: Wood Frame, Vinyl Siding
- Roof: Composition, Fiberglass, Metal, Shingle
- Windows: Double Pane Windows
- Building Size: 2856
- Square Feet: 2,856
- Sq. Ft. Source: Seller
- Living Area: 2,856 Sq. Ft.
- Finished Total: 2,856 Sq. Ft.
- Finished Above Grnd: 2,476 Sq. Ft.
- Finished Below Grnd: 380 Sq. Ft.
- Year Built: 2022
- Property Condition: New Construction
Lot Features
- Property View: Scenic, Trees/Woods
- Lot Size (Acres): 1.03
- Lot Size (Sq. Ft.): 44,866.8
- Lot Size Source: Public Records
- Zoning: F
- Lot Description: Near Country Club, Well Landscaped, Cul-de-Sac, Level, Wooded, Abuts Conservation, Near Golf Course, Near Public Beach, Near Town, Neighborhood, Rural, Subdivided
- Fencing (Description): Fenced
Green Features
- Energy Efficient: Ceiling Fans, Water Heater, Thermostat
Financial Considerations
- Association Fee: $250
- Assoc Fee Freq.: Annually
- Tax Amount: $8,573
- Tax Year: 2025
Disclosures and Reports
- Exclusions: televisions, large cabinet in bonus room
- Block: 25
- Lot Number: 16
Listed by Better Homes & Gardens Real Estate/The Masiello Group (207) 560-4683
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Listing agent
— 23 Pennywhistle Dr —
Better Homes & Gardens Real Estate/The Masiello Group
207-560-4683
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 23 Pennywhistle Dr
School District:Regional School Unit 14
| Name | Grades | Distance |
|---|---|---|
Windham Primary School 404 Gray Road, Windham, ME 04062 | K-3 | 2.6 mi |
Manchester School 709 Roosevelt Trail, Windham, ME 04062 | 4-5 | 6 mi |
Windham Middle School, Windham, ME 408 Gray Road, Windham, ME 04062 | 6-8 | 2.9 mi |
Windham High School, Windham, ME 406 Gray Road, Windham, ME 04062 | 9-12 | 2.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 23 Pennywhistle Dr
Tax History
Tax History for 23 Pennywhistle Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,573
13%
$710,900
8%
2024
$7,578
9%
$660,700
6%
2023
$6,975
10%
$622,800
14%
2022
$6,347
510%
$546,700
563%
2021
$1,040
5%
$82,500
25%
2020
$989
—
$65,900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 23 Pennywhistle Dr
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23 Pennywhistle Drive, Windham, ME 04062 (MLS# 1662103) is a Single Family property with 3 bedrooms, 2 full bathrooms and 2 partial bathrooms. 23 Pennywhistle Drive is currently listed for $874,900 and was received on May 16, 2026. Want to learn more about 23 Pennywhistle Drive? Do you have questions about finding other Single Family real estate for sale in Windham? You can browse all Windham real estate or contact a Coldwell Banker agent to request more information.