Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$462,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1,388 Sq. Ft.
  • 1.9 Acres
  • Updated 1 day ago

Next open house:

Open House: 10:00 AM - 11:30 AM

Saturday 6/20 10:00 AM - 11:30 AM

106 Highland Cliff Road,Windham, ME 04062

106 Highland Cliff RoadWindhamME04062

Get directions
See This Home
Save This Home
See This Home
Save This Home
Tucked on a quiet 1.9-acre lot, this 3-bedroom, 1-bath split-entry home has room to spread out. The main level features an open kitchen that flows into the living room, with hardwood flooring, along with two bedrooms and a full bath. Downstairs, you'll find a third bedroom and a finished bonus room that can easily serve as a home office, gym, playroom, or guest space. A partial wrap-around deck provides a private spot to relax and take in the surroundings, while the lot offers plenty of room to enjoy the outdoors. Despite its peaceful setting, the home is just a short drive to North Windham for shopping and everyday errands, with Portland also within easy reach.

Full Property Details for 106 Highland Cliff Rd

General

  • Price: $462,000
  • Taxes: $4,069 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MREIS
  • MLS ID: 1667810
  • Updated: 6/18/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 5
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Equipment: Air Radon Mitigation System

Exterior

  • Porch/Patio/Deck: Deck

Parking

  • Parking Features: Gravel, 1 - 4 Spaces

Location

  • County: Cumberland

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Oil, Baseboard, Hot Water

Utilities

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

Structural Information

  • Architectural Style: Split Level
  • Construction: Wood Frame, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Bulkhead, Interior Entry, Finished, Full
  • Roof: Shingle
  • Square Feet: 1,388
  • Sq. Ft. Source: Public Records
  • Finished Total: 1,388 Sq. Ft.
  • Finished Above Grnd: 844 Sq. Ft.
  • Finished Below Grnd: 544 Sq. Ft.
  • Year Built: 1996

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 1.9
  • Lot Size (Sq. Ft.): 82,764
  • Zoning: F
  • Lot Description: Rural, Rolling Slope, Wooded

Financial Considerations

  • Tax Amount: $4,069
  • Tax Year: 2025

Disclosures and Reports

  • Lot Number: A01

Listed by A Team Realty (207) 894-8484

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 106 Highland Cliff Rd —

  • A Team Realty

    207-894-8484

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 106 Highland Cliff Rd

School District:Regional School Unit 14
NameGradesDistance
Windham Primary School
404 Gray Road, Windham, ME 04062
K-32.9 mi
Manchester School
709 Roosevelt Trail, Windham, ME 04062
4-56.4 mi
Windham Middle School, Windham, ME
408 Gray Road, Windham, ME 04062
6-83.1 mi
Windham High School, Windham, ME
406 Gray Road, Windham, ME 04062
9-123.1 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 106 Highland Cliff Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/18/2026
Listed
$462,000
75.59%
MLS
9/28/2018
Sold
$263,113
—
Public Record
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 106 Highland Cliff Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,069
5%
$337,400
—
2024
$3,870
9%
$337,400
6%
2023
$3,562
6%
$318,000
10%
2022
$3,362
17%
$289,600
15%
2021
$2,864
—
$252,300
23%
2021
$2,864
-5%
$205,200
—
2019
$3,004
5%
$205,200
9%
2018
$2,852
10%
$187,900
19%
2017
$2,599
5%
$158,200
—
2016
$2,484
4%
$158,200
—
2015
$2,397
3%
$158,200
—
2014
$2,321
2%
$158,200
—
2013
$2,286
—
$158,200
—
View All
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 106 Highland Cliff Rd

$
Down Payment
%
$
%

$
$

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by A Team Realty (207) 894-8484

Similar Properties near 106 Highland Cliff Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

203 Gray Rd, Falmouth, ME 04105 - Photo 1
$484,000

203 Gray Rd  Falmouth, ME 04105

  • Single Family
  • Active
  • Updated 8 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,390
    Sq. Ft.
Listed by LUX Realty
9 Cottage Pl, Westbrook, ME 04092 - Photo 1 Price Reduced
-$6,000 (-1.26%)
$469,000
Open House

9 Cottage Pl  Westbrook, ME 04092

  • Single Family
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,120
    Sq. Ft.
Listed by RE/MAX Shoreline
10 Elm St, Gorham, ME 04038 - Photo 1 Price Reduced
-$24,000 (-4.81%)
$475,000

10 Elm St  Gorham, ME 04038

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 1
    Total Bath
  • 2,017
    Sq. Ft.
Listed by Maine Real Estate Co
11 Libby Ave, Westbrook, ME 04092 - Photo 1
$450,000

11 Libby Ave  Westbrook, ME 04092

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,560
    Sq. Ft.
Listed by Maine Home Connection

Just Listed near 106 Highland Cliff Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

44 Hunts Hill Rd, Gray, ME 04039 - Photo 1 Just Listed
$275,000

44 Hunts Hill Rd  Gray, ME 04039

  • Single Family
  • Active
  • Updated 3 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 928
    Sq. Ft.
Listed by Keller Williams Realty
23 Callaway Dr, Gray, ME 04039 - Photo 1 Just Listed
$669,995

23 Callaway Dr  #23  Gray, ME 04039

  • Condo
  • Active
  • Updated 14 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,961
    Sq. Ft.
Listed by Plowman Realty Group
Lot 25 Woodcock Dr, Gray, ME 04039 - Photo 1 Just Listed
$729,000

Lot 25 Woodcock Dr  Gray, ME 04039

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,796
    Sq. Ft.
Listed by Town & Shore Real Estate
3 Spiro Ave, Gray, ME 04039 - Photo 1 Just Listed
$450,000

3 Spiro Ave  Gray, ME 04039

  • Single Family
  • Active
  • Updated 13 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,933
    Sq. Ft.
Listed by Landing Real Estate

Price Reduced near 106 Highland Cliff Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

123 Lewiston Rd, Gray, ME 04039 - Photo 1 Price Reduced
-$10,100 (-2.2%)
$449,900

123 Lewiston Rd  Gray, ME 04039

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 2
    Units
  • 1.84
    Acres
Listed by Plowman Realty Group
281 Portland Rd, Gray, ME 04039 - Photo 1 Price Reduced
-$24,000 (-4.37%)
$525,000

281 Portland Rd  Gray, ME 04039

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,770
    Sq. Ft.
Listed by Real Broker
21 Eagles Nest Rd, Gray, ME 04039 - Photo 1 Price Reduced
-$10,000 (-1.54%)
$639,900

21 Eagles Nest Rd  Gray, ME 04039

  • Single Family
  • Active
  • Updated 3 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,664
    Sq. Ft.
Listed by Kre Brokerage Group
114 Wild Acres Rd, Raymond, ME 04071 - Photo 1 Price Reduced
-$57,000 (-3.49%)
$1,575,000

114 Wild Acres Rd  Raymond, ME 04071

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,775
    Sq. Ft.
Listed by Shannon Boyington (207) 615-2642

Recent Sales near 106 Highland Cliff Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

26 Marshall Valley Rd, Windham, ME 04062 - Photo 1 Sold
$470,000

26 Marshall Valley Rd  Windham, ME 04062

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 2,703
    Sq. Ft.
Listed by Getty Real Estate Services, LLC
Sold by Keller Williams Realty
10 Twoey Dr, Windham, ME 04062 - Photo 1 Sold
$505,000

10 Twoey Dr  Windham, ME 04062

  • Single Family
  • Closed
  • 3
    Beds
  • 1
    Total Bath
  • 1,104
    Sq. Ft.
Listed by Demetria Real Estate
Sold by Keller Williams Realty
937 Duck Pond Rd, Westbrook, ME 04092 - Photo 1 Sold
$501,000

937 Duck Pond Rd  Westbrook, ME 04092

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,074
    Sq. Ft.
Listed by Portside Real Estate Group
Sold by Portside Real Estate Group
26 Depot St, Windham, ME 04062 - Photo 1 Sold
$500,000

26 Depot St  Windham, ME 04062

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,337
    Sq. Ft.
Listed by RE/MAX Shoreline
Sold by Excellence Realty

106 Highland Cliff Road, Windham, ME 04062 (MLS# 1667810) is a Single Family property with 3 bedrooms and 1 full bathroom. 106 Highland Cliff Road is currently listed for $462,000 and was received on June 18, 2026. Want to learn more about 106 Highland Cliff Road? 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.

Tour this property