23 Pennywhistle Dr Windham, ME 04062
Windham AreaEstimated payment $5,352/month
Highlights
- Country Club
- Property is near a beach
- Deck
- New Construction
- Scenic Views
- Wooded Lot
About This Home
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.
Listing Agent
Better Homes & Gardens Real Estate/The Masiello Group Listed on: 05/16/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $8,573
Year Built
- Built in 2022 | New Construction
Lot Details
- 1.03 Acre Lot
- Cul-De-Sac
- Rural Setting
- Fenced
- Landscaped
- Level Lot
- Wooded Lot
HOA Fees
- $21 Monthly HOA Fees
Parking
- 3 Car Direct Access Garage
- Tandem Parking
- Garage Door Opener
- Off-Street Parking
Property Views
- Scenic Vista
- Woods
Home Design
- Farmhouse Style Home
- Poured Concrete
- Wood Frame Construction
- Shingle Roof
- Composition Roof
- Fiberglass Roof
- Metal Roof
- Vinyl Siding
- Radon Mitigation System
Interior Spaces
- Multi-Level Property
- Ceiling Fan
- 1 Fireplace
- Double Pane Windows
- Storage
- Luxury Vinyl Tile Flooring
- Fire Sprinkler System
Kitchen
- Gas Range
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
- En-Suite Primary Bedroom
- Bathtub
- Shower
Laundry
- Dryer
- Washer
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Doghouse Basement Entry
- Interior Basement Entry
- Natural lighting in basement
Eco-Friendly Details
- Solar owned by seller
- Solar owned by a third party
Outdoor Features
- Property is near a beach
- Deck
- Porch
Location
- Property is near golf course
Utilities
- Cooling Available
- Zoned Heating
- Heat Pump System
- Baseboard Heating
- Hot Water Heating System
- Thermostat
- Electricity To Lot Line
- Generator Hookup
- Well
- Water Heater
- Septic Tank
- Septic Design Available
- Private Sewer
- Internet Available
Listing and Financial Details
- Exclusions: televisions, large cabinet in bonus room
- Legal Lot and Block 16 / 25
Community Details
Overview
- Durant Homestead Subdivision
- Near Conservation Area
Recreation
- Country Club
Map
Home Values in the Area
Average Home Value in this Area
Tax History
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 |
Property History
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 |
|---|---|---|---|---|
| 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 |
Source: Maine Listings
MLS Number: 1662103
APN: 6 25 15
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.
© 2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Homes.com, LLC, 17600 Laguna Canyon Rd Irvine, CA 92618 (888)-952-6393
- 32 Pennywhistle Dr
- 62 Chute Rd
- 2 Twoey Dr
- 315 River Rd
- 22 Montgomery Rd
- 41 Main St
- 9 Gunpowder Mill Rd
- 42 Main St
- 18 Cosmic Way Unit 18
- 30 Marshall Valley Rd
- 12 Dolley Farm Rd Unit 6
- 108 Highland Cliff Rd
- Lot 4 Highland Cliff Rd
- 30 Dolley Farm Rd Unit 13
- 106 Highland Cliff Rd
- 13 Maysens Way
- 40 Highland Cliff Rd
- 25 Leonards Way
- 8 Beaulieu Dr
- 8 Beaulieu Dr
- 4 Me-4
- 993 Duck Pond Rd Unit Apartment 1
- 802 Methodist Rd
- 2-4 Me-4
- 1 Overlook Dr Unit 1 Overlook Drive Apt
- 41 Lotts Dr Unit 2
- 100 Hardy Rd
- 84 Johnson Rd
- 1 Ari Dr
- 68 Nicklaus Ln Unit 113
- 198 Mountain Rd
- 118 Pierce St
- 300 E Bridge St Unit 123
- 140 North St
- 52-52 Myrtle St Unit 50-2
- 263 Brown St Unit 2
- 7 North St Unit 1
- 758 Main St Unit 2
- 670 Main St
- 723 Riverside St
Ask me questions while you tour the home.