$1,595,000
Original price: $1,795,000
3 Beds
2.5 Baths
2,016 sqft (on 0.28 acres)
20 Ladyslipper Drive, Windham, ME 04062
Est. Mortgage $9,756/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 2025
0.28 acre lot
$791/sqft
Garage
Local Information
- Map ViewExplore the area around 20 Ladyslipper Drive.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: about 6 hours ago
Listing courtesy of Judy George Realty
Source: Maine Listings, MLS#1663172
Also Listed on Maine Listings.
About this House
New construction on Little Sebago Lake is a once-in-a-decade event. And this is that event.
A sun drenched contemporary three-story residence modeled after a Maine Home + Design award winning home and sited on a private dead-end road shared by just six year-round properties.
This home faces DUE WEST, so that every room on the waterside catches the full arc of sunset through the floor-to-ceiling glass.
The colors were selected to blend in the surrounding woods and is custom shingled in cedar. Rare public water from the Portland Water District from May-October plus a drilled well for winter months.
The 38-foot-deep garage serves for convenient storage and is 10 feet tall. There is opportunity to finish part !
Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was added.
Inside, new hardwood floors run throughout. The kitchen anchors the open-concept main level with a ten-foot quartz island with double waterfall features. Subzero fridge and Viking induction range plus a double pantry. Central HVAC and a propane fireplace keep the home comfortable year-round.
Two decks extend the living space toward the water -- one for morning, one for the long western light. The primary suite has a private door leading to the 3rd floor deck, where you may relax and soak in the views and sounds of the lake.
At the water's edge, an original boathouse and a second storage screened structure remain from the property's earlier life, and both can make wonderful bunk or playhouses, fishing shacks or storage for all the recreational needs.
For a individual who values waterfront access and flexibility, these buildings represent options that would NOT be permitted today. Water is 8 ft. deep at the dock!
Little Sebago is one of southern Maine's finest lakes with over 6 miles of water to explore and enjoy. 30 minutes to the Portland Jetport/Amtrak station, 2 hours to Logan Airport. less than 1 hour to local ski mountains create end
A sun drenched contemporary three-story residence modeled after a Maine Home + Design award winning home and sited on a private dead-end road shared by just six year-round properties.
This home faces DUE WEST, so that every room on the waterside catches the full arc of sunset through the floor-to-ceiling glass.
The colors were selected to blend in the surrounding woods and is custom shingled in cedar. Rare public water from the Portland Water District from May-October plus a drilled well for winter months.
The 38-foot-deep garage serves for convenient storage and is 10 feet tall. There is opportunity to finish part !
Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was added.
Inside, new hardwood floors run throughout. The kitchen anchors the open-concept main level with a ten-foot quartz island with double waterfall features. Subzero fridge and Viking induction range plus a double pantry. Central HVAC and a propane fireplace keep the home comfortable year-round.
Two decks extend the living space toward the water -- one for morning, one for the long western light. The primary suite has a private door leading to the 3rd floor deck, where you may relax and soak in the views and sounds of the lake.
At the water's edge, an original boathouse and a second storage screened structure remain from the property's earlier life, and both can make wonderful bunk or playhouses, fishing shacks or storage for all the recreational needs.
For a individual who values waterfront access and flexibility, these buildings represent options that would NOT be permitted today. Water is 8 ft. deep at the dock!
Little Sebago is one of southern Maine's finest lakes with over 6 miles of water to explore and enjoy. 30 minutes to the Portland Jetport/Amtrak station, 2 hours to Logan Airport. less than 1 hour to local ski mountains create end
Home Details for 20 Ladyslipper Drive
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MLS Status: Active |
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Interior Details Basement: Interior Entry,Walk-Out Access,UnfinishedNumber of Rooms: 6Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2016 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Disposal, Dryer, Electric Range, Refrigerator, WasherDishwasherDisposalDryerRefrigeratorWasher |
Heating & Cooling Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Window: Triple Pane WindowsDoor: Storm Door(s)Flooring: Tile, Wood |
Levels, Entrance, & Accessibility Levels: Multi/SplitFloors: Tile, Wood |
View Has a ViewView: Scenic |
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Exterior Home Features Roof: Metal ShinglePatio / Porch: DeckOther Structures: Outbuilding, Shed(s)Foundation: Poured ConcreteNo Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Other,5 - 10 Spaces,On Site,Garage Door Opener |
Frontage WaterfrontRoad Frontage: Private RoadRoad Surface Type: Gravel, DirtOn Waterfront |
Water & Sewer Sewer: Private SewerWater Body: Little Sebago |
Farm & Range Frontage Length: Waterfrontage: 80, Waterfrontage Owned: 80 |
Finished Area Finished Area (above surface): 2016 Square Feet |
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Days on Market: 116 |
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Year Built Year Built: 2025 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary |
Building Construction Materials: Wood Frame, Wood SidingIs a New Construction |
Property Information Condition: New Construction |
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Price List Price: $1,595,000Price Per Sqft: $791 |
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Direction & Address City: Windham |
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Listing Agent Listing ID: 1663172 |
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Building Area Building Area: 2016 Square Feet |
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Lot Area: 0.28 acres |
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BasementMls Number: 1663172Above Grade Unfinished Area: 2016 |
Around this home
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.
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.
Market trends in Windham
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
96
22MoM
Home Value
Trulia Estimate
$1.57MSince last month
Increased$17K (+1.1%)Since last year
Increased$955K (+154.1%)Since last sale
Increased$1M (+224.6%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +523% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.57M |
| August 2026 | $1.56M |
| July 2026 | $1.56M |
| June 2026 | $1.94M |
| May 2026 | $1.99M |
| April 2026 | $623K |
| March 2026 | $629K |
| February 2026 | $602K |
| January 2026 | $579K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.66 | Single-Family Home | $570,000 | 11/21/25 | 3 | 2.5 | 1,864 | |
0.31 | Single-Family Home | $431,500 | 11/15/25 | 3 | 1 | 1,648 | |
0.52 | Single-Family Home | $510,000 | 11/14/25 | 3 | 2.5 | 2,522 | |
0.79 | Single-Family Home | $1,050,000 | 08/06/26 | 3 | 2 | 2,140 | |
0.65 | Single-Family Home | $603,000 | 07/13/26 | 3 | 2.5 | 1,816 | |
0.54 | Single-Family Home | $660,000 | 01/23/26 | 4 | 2.5 | 2,070 | |
0.54 | Single-Family Home | $680,000 | 08/28/26 | 3 | 3 | 2,875 | |
0.53 | Single-Family Home | $990,000 | 06/12/26 | 4 | 2.5 | 2,992 | |
0.35 | Single-Family Home | $1,075,000 | 03/17/26 | 2 | 1 | 1,158 | |
1.27 | Single-Family Home | $520,000 | 11/14/25 | 3 | 2.5 | 1,440 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.19 | $1,955,000 | 4 | 3.5 | 3,377 | For Sale | |
0.21 | $494,200 | 3 | 1.5 | 1,793 | Off Market | |
0.23 | $773,300 | 5 | 3.5 | 3,278 | Off Market | |
0.26 | $482,000 | 3 | 1 | 1,216 | Off Market | |
0.28 | $708,500 | 3 | 2.5 | 2,000 | Off Market | |
0.29 | - | - | - | - | Off Market | |
0.31 | $431,500 | 3 | 1 | 1,648 | Recently Sold | |
0.35 | $1,075,000 | 2 | 1 | 1,158 | Recently Sold | |
0.32 | - | - | - | - | Off Market | |
0.36 | $486,200 | 3 | 2.5 | 1,812 | Off Market | |
0.52 | $510,000 | 3 | 2.5 | 2,522 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jul 29, 2026 Source: Maine Listings #1663172 | PriceChange | $1,595,000 Price decreased by 11% |
Jul 3, 2026 Source: Maine Listings #1663172 | PriceChange | $1,795,000 Price decreased by 10% |
May 25, 2026 Source: Maine Listings #1663172 | Listed For Sale | $2,000,000 |
Sep 15, 2023 Source: Maine Listings #1569291 | Sold | $485,000 |
Aug 25, 2023 Source: Maine Listings #1569291 | Pending | $299,900 |
Aug 18, 2023 Source: Maine Listings #1569291 | Listed For Sale | $299,900 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $5,860 | $510,900 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Judy George Realty
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.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
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Frequently asked questions about 20 Ladyslipper Drive
- What is the estimated monthly payment for 20 Ladyslipper Drive?Based on a $1,595,000 list price with 20% down at today's rates, the estimated monthly payment for 20 Ladyslipper Drive in Windham, ME is approximately $9,996 (about $8,618 principal & interest, $1,303 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Windham?Residents describe Windham, ME as easy to park in, well-kept, and quiet. Most residents say you need a car. See homes for sale in Windham, ME.
- What are the closest schools to 20 Ladyslipper Drive?The closest schools to 20 Ladyslipper Drive in Windham, ME are Manchester School (Elementary, rated 7/10), Windham High School (rated 6/10), Windham Middle School (rated 4/10).
- What is 20 Ladyslipper Drive estimated to be worth?Trulia's estimated value for 20 Ladyslipper Drive in Windham, ME is $1,574,100.
- Does 20 Ladyslipper Drive have air conditioning?Yes, 20 Ladyslipper Drive in Windham, ME has air conditioning.
- Does 20 Ladyslipper Drive have laundry facilities?Yes, 20 Ladyslipper Drive in Windham, ME has in-unit laundry.
20 Ladyslipper Drive, Windham, ME 04062 is a 3 bedroom, 3 bathroom, 2,016 sqft single-family home built in 2025. This property is currently available for sale and was listed by Maine Listings on May 20, 2026. The MLS # for this home is MLS# 1663172.