Is a car needed in Windham, ME?

As of early 2026, 96% of users say car is needed

Is parking easy in Windham, ME?

As of early 2026, 91% of users say parking is easy

Are yards well-kept in Windham, ME?

As of early 2026, 85% of users say yards are well-kept

Is there wildlife in Windham, ME?

As of early 2026, 80% of users say there's wildlife

Does Windham, ME show holiday spirit?

As of early 2026, 79% of users say there's holiday spirit

Would people walk alone at night in Windham, ME?

As of early 2026, 78% of users say people would walk alone at night

Is Windham, ME quiet?

As of early 2026, 67% of users say it's quiet

Do residents of Windham, ME plan to stay at least 5 years?

As of early 2026, 67% of users say they plan to stay for at least 5 years

Is Windham, ME dog-friendly?

As of early 2026, 67% of users say it's dog friendly

Are neighbors friendly in Windham, ME?

As of early 2026, 66% of users say neighbors are friendly

Do kids play outside in Windham, ME?

As of early 2026, 66% of users say kids play outside

Are there community events in Windham, ME?

As of early 2026, 31% of users say there are community events

Does Windham, ME have sidewalks?

As of early 2026, 28% of users say there are sidewalks

Is Windham, ME walkable to restaurants?

As of early 2026, 28% of users say it's walkable to restaurants

Are the streets well-lit in Windham, ME?

As of early 2026, 17% of users say streets are well-lit

Is Windham, ME walkable to grocery stores?

As of early 2026, 13% of users say it's walkable to grocery stores

FOR SALE

NEW CONSTRUCTION

0.28 ACRES

20 Ladyslipper Drive
Windham, ME 04062

3 Beds
2.5 Baths
2,016 sqft (on 0.28 acres)

$2,000,000

3 Beds

2.5 Baths

2,016 sqft

(on 0.28 acres)

Local Information

-- mins to

Commute Destination

Last check for updates: about 7 hours ago

Listing courtesy of Judy George Realty

Source: Maine Listings, MLS#1663172

Also Listed on Maine Listings.

Description

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. Enjoy 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 or all. Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was also 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.

Little Sebago Lake 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 endless amenities

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

$992

Listed

14 days ago

Home Details for 20 Ladyslipper Drive

Active Status
MLS Status: Active

Interior Features
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

Exterior Features
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

Days on Market
Days on Market: 14

Property Information
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

Price & Status
Price List Price: $2,000,000Price Per Sqft: $992

Location
Direction & Address City: Windham

Agent Information
Listing Agent Listing ID: 1663172

Building
Building Area Building Area: 2016 Square Feet

Lot Information
Lot Area: 0.28 acres

Miscellaneous
BasementMls Number: 1663172Above Grade Unfinished Area: 2016

Market trends in Windham

Last updated April 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

Price History for 20 Ladyslipper Drive

Date	Price	Event	Source
05/25/2026	$2,000,000	Listed For Sale	Maine Listings #1663172

09/15/2023	$485,000	Sold	Maine Listings #1569291
Recording Date 09/15/2023 County Transfer Tax N/A Total Transfer Tax N/A
08/25/2023	$299,900	Pending	Maine Listings #1569291

08/18/2023	$299,900	Listed For Sale	Maine Listings #1569291

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Property Tax and Assessment

Year	2024
Tax	$5,860
Assessment	$510,900

Home facts updated by county records

Comparable Sales for 20 Ladyslipper Drive

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
14 Ridge Drive, Windham, ME	0.36	Single-Family Home	$475,000	08/20/25	3	2.5	1,812
2 Cobalt Court, Windham, ME	0.66	Single-Family Home	$570,000	11/21/25	3	2.5	1,864
7 Many Oaks Lane, Windham, ME	0.31	Single-Family Home	$431,500	11/15/25	3	1	1,648
20 Cameron Lane, Windham, ME	0.52	Single-Family Home	$510,000	11/14/25	3	2.5	2,522
8 Lily Lane, Windham, ME	0.54	Single-Family Home	$660,000	01/23/26	4	2.5	2,070
147 Sand Bar Road, Windham, ME	0.71	Single-Family Home	$1,800,000	07/30/25	3	3	2,500
34 Many Oaks Lane, Windham, ME	0.35	Single-Family Home	$1,075,000	03/17/26	2	1	1,158
34 Woodland Road, Windham, ME	1.27	Single-Family Home	$520,000	11/14/25	3	2.5	1,440
214 Tandberg Trail, Windham, ME	1.27	Single-Family Home	$479,800	10/09/25	3	2	2,052
158 Mt Hunger Shore Road, Windham, ME	1.08	Single-Family Home	$399,900	09/08/25	3	2	2,134

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Assigned Schools

These are the assigned schools for 20 Ladyslipper Drive.

View nearby schools on GreatSchools

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.

Charliestandishjr
Resident
2mo ago
"There are lots of dogs in the neighborhood . Everyone’s welcome and pets are always welcomed here. And everyone picks up their dogs pop"
0
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Charliestandishjr
Resident
5mo ago
"It’s a good place to live . I feel safe in my neighborhood. My neighbors are all friendly .They’re is enough stores in town that I don’t have to go to Portland "
0
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Charliestandishjr
Resident
1y ago
"I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
0
Flag
Geri Post
Resident
1y ago
"My wonderful neighbors very helpful. Look out for each other and consider ourselves family quiet neighborhood and nice area surrounding trees and a pool"
0
Flag
Jeannine M.
Resident
5y ago
"Great area for kids and easy to get to Portland for nightlife or the Mountains for skiing. There's farmer's markets and maple sugar farms, and many deer. If you have kids this is a great place to live where they can ride bikes or play in the lake. "
1
Flag
Jess I.
Resident
7y ago
"Many of the people in my neighborhood enjoy the outdoors. We live on the Presumscot River so we have all kinds of wildlife, many enjoy water sports like kayaking, paddle boarding, boating, fishing, and you see them out and about. We also have close access to the Mt. Division trail which is great for everyone, including Fido, as long as they are on a leash. There are farmers markets, lots of shopping, restaurants and sea coast fun park. Just go 5miles up the road. Or the Highschool has sports fields, an outdoor track, a rock climbing wall inside through adult Ed I think? Windham is a great place to be."
0
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Katie
Resident
7y ago
"no public transport. good areas and bad. dog friendly. side roads do not get taking care of well in winter months . nice trails for walking. not a very well known going out town most people still travel to portland for drinks with friends dancing ect. "
13
Flag
Lizmc200
Resident
7y ago
"I love everything about Windham. The people are great and the town has everything you need in it. "
0
Flag
Laura C.
Resident
7y ago
"One way in and one way out. Not a lot of traffic or random drive throughs. Quiet, nice neighborhood with lots of friendly faces."
2
Flag
Jennilee M.
Resident
7y ago
"Quiet and friendly, I love this neighborhood. There are Lots of kids around with pets in the area. Everyone looks out for one another "
1
Flag
zmbailey
11y ago
"If you don't have a car, do not move here. Air is relatively clean though."
0
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Julie L. D.
12y ago
"I live two streets from Carmichael and love living so close to the lakes and less than twenty minutes to Portland! The schools are within a 5-7 minute drive and shopping is less than three miles down the road. You can avoid the traffic by taking the backroads, that lead into outer Washington Ave or travel down the road to enter the Maine Turnpike just down the street in Gray. I love listening to the loons on the lake, early Spring into the Fall, and it is always fun to watch the fireworks show on the lake July 4th, put on by neighbors all around the lake! With the snowmobile trails so close by, I can hop on my sled, ice fishing, ice skate, or boat all outside my front door! This is a great area to retire, or raise a family"
0
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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

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.

20 Ladyslipper Drive
Windham, ME 04062

$2,000,000

$2,000,000

Local Information