101 Highland Cliff Road, Windham, ME 04062
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Property image
OFF MARKET

101 Highland Cliff Road
Windham, ME 04062

  • 3 Beds
  • 2.5 Baths
  • 2,418 sqft (on 1.80 acres)

$563,400

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $3,414/mo*

$563,400

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $3,414/mo*
3 Beds
2.5 Baths
2,418 sqft
(on 1.80 acres)

Local Information

  • Map ViewExplore the area around 101 Highland Cliff Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1979
Lot Size
1.8 acres
Living Area
2,418 sqft
Price/Sqft
$233
Parking
2 Car Garage
Last check for updates: about 10 hours ago
Listed by Demetria Real Estate
Bought with: Realty ONE Group - Compass
Source: Maine Listings, MLS#1571833

About this House

The first thing you'll notice about 101 Highland Cliff Road is the luxurious front yard, providing great privacy, a sense of space, and room to enjoy the outdoors. Outdoor amenities pepper the property, including beautiful gardens, a porch swing, an outdoor deck featuring an above ground pool and a walkout basement. Inside there is more than meets the eye with hardwood floors, a spacious granite kitchen, formal dining room, pellet stove and more! Basement offers additional flexible space. Need storage? There is ample space above and below the garage! This house exemplifies Maine living and this is the first time it is on the market, being sold by the original owners, who have cared for the property since it was first built. Now the home is ready for its new chapter. Will it be with you?
101 Highland Cliff Road, Windham, ME 04062 is a 3 bedroom, 3 bathroom, 2,418 sqft single-family home built in 1979. It last sold for $460,000 on Nov 27, 2023 (2% above the $450,000 asking price). It is currently off market. The Trulia Estimate is $563,400, with a rent estimate of $3,585/month.

Home Details for 101 Highland Cliff Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior EntryNumber of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Dining Room, Family Room, Kitchen, Living Room, Mud Room, Other Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2418 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Electric Range, RefrigeratorDishwasherDryerRefrigerator
Heating & Cooling
Heating: Baseboard,Hot Water,Zoned,StoveNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Carpet, Laminate, Wood
Levels, Entrance, & Accessibility
Floors: Carpet, Laminate, Wood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, PorchNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved,5 - 10 Spaces,On Site,Off Street,Garage Door Opener,Storage
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 1676 Square FeetFinished Area (below surface): 742 Square Feet

Property Information

Year Built
Year Built: 1979
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Wood Frame, Vinyl Siding

Price & Status

Price
List Price: $450,000
Status Change & Dates
Off Market Date: Sun Oct 15 2023

Location

Direction & Address
City: Windham

Building

Building Area
Building Area: 2418 Square Feet

Lot Information

Lot Area: 1.8 Acres

Miscellaneous

BasementMls Number: 1571833Above Grade Unfinished Area: 1676

Price History for 101 Highland Cliff Road

DatePriceEventSource
11/27/2023$460,000Sold
Maine Listings #1571833
10/16/2023$450,000PendingMaine Listings #1571833
10/10/2023$450,000PriceChange
Maine Listings #1571833
09/27/2023$475,000PriceChange
Maine Listings #1571833
09/12/2023$499,000Listed For SaleMaine Listings #1571833

Market trends in Windham

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$464K
Sale-to-List Price
—
Price per sq ft
$276
Available listings
68
12
MoM
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Property Tax and Assessment

Year2024
Tax$5,464
Assessment$476,400
Home facts updated by county records

Comparable Sales for 101 Highland Cliff Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.12
Single-Family Home
$590,000
11/10/25
3
2.5
2,472
0.22
Single-Family Home
$769,500
01/09/26
3
2.5
2,200
0.19
Single-Family Home
$470,000
03/30/26
2
2
2,703
0.16
Single-Family Home
$570,000
11/17/25
4
3.5
3,030
0.47
Single-Family Home
$650,000
12/19/25
3
2
2,331
0.70
Single-Family Home
$750,000
06/30/26
3
2.5
2,831
0.75
Single-Family Home
$605,000
06/22/26
3
2.5
2,472
0.77
Single-Family Home
$735,000
07/16/26
3
2
2,856

Nearby homes

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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
    "There are lots of dogs in the neighborhood . Everyone’s welcome and pets are always welcomed here. And everyone picks up their dogs pop"
  • Charliestandishjr
    "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 "
  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
  • Geri Post
    "My wonderful neighbors very helpful. Look out for each other and consider ourselves family quiet neighborhood and nice area surrounding trees and a pool"
  • Jeannine M.
    "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. "
  • Jess I.
    "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."
  • Katie
    "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. "
  • Lizmc200
    "I love everything about Windham. The people are great and the town has everything you need in it. "
  • Laura C.
    "One way in and one way out. Not a lot of traffic or random drive throughs. Quiet, nice neighborhood with lots of friendly faces."
  • Jennilee M.
    "Quiet and friendly, I love this neighborhood. There are Lots of kids around with pets in the area. Everyone looks out for one another "
  • zmbailey
    "If you don't have a car, do not move here. Air is relatively clean though."
  • Julie L. D.
    "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"

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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.
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