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$849,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2 Partial Baths
  • 2,856 Sq. Ft.
  • 1.03 Acres
  • 3 Car Garage
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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 for 23 Pennywhistle Dr

General

  • Price: $849,900
  • HOA FEE: $21/month
  • HOA FEE FREQ.: Annually
  • Taxes: $8,573 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MREIS
  • MLS ID: 1662103
  • Updated: 6/12/2026
  • Added to Site: 50 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: Cooktop, Dishwasher, Dryer, Gas Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • 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: Fire Sprinkler System
  • Equipment: Air Radon Mitigation System, Internet Access Available

Exterior

  • Porch/Patio/Deck: Deck, Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking Features: Paved, 1 - 4 Spaces, On-Site Parking, Off Street, Garage Door Opener, Inside Entrance, Tandem

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, Zoned, Other

Utilities

  • Sewer: Private Sewer, Septic Design Available, Septic Tank
  • Water: Well
  • Well: Yes

Structural Information

  • Architectural Style: Farmhouse, Modern
  • Construction: Wood Frame, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Doghouse, Interior Entry, Walk-Out Access, Daylight, Finished, Full
  • Roof: Composition, Fiberglass, Metal, Shingle
  • Windows: Double Pane Windows
  • Square Feet: 2,856
  • Sq. Ft. Source: Seller
  • 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
  • Zoning: F
  • Lot Description: Abuts Conservation, Near Country Club, Near Golf Course, Near Public Beach, Near Town, Neighborhood, Rural, Subdivided, Cul-de-Sac, Level, Landscaped, Wooded
  • 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

  • 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

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 23 Pennywhistle Dr

School District:Regional School Unit 14
NameGradesDistance
Windham Primary School
404 Gray Road, Windham, ME 04062
K-32.6 mi
Manchester School
709 Roosevelt Trail, Windham, ME 04062
4-56 mi
Windham Middle School, Windham, ME
408 Gray Road, Windham, ME 04062
6-82.9 mi
Windham High School, Windham, ME
406 Gray Road, Windham, ME 04062
9-122.8 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/12/2026
Price Reduced
$849,900
-2.86%
MLS
5/16/2026
Listed
$874,900
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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 for 23 Pennywhistle Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

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NMLS#: 1598647

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Listed by Better Homes & Gardens Real Estate/The Masiello Group (207) 560-4683

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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 $849,900 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.

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