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

PENDING

3.94 ACRES

21 Cliff Drive
Windham, ME 04062

2 Beds
2 Baths
2,976 sqft (on 3.94 acres)

$889,000

Est. Mortgage $5,240/mo*

Get Pre-Qualified

$889,000

Est. Mortgage $5,240/mo*

Get Pre-Qualified

2 Beds

2 Baths

2,976 sqft

(on 3.94 acres)

Local Information

-- mins to

Commute Destination

Last check for updates: about 5 hours ago

Listing courtesy of The Flaherty Group

Source: Maine Listings, MLS#1654107

Also Listed on Maine Listings.

Description

Welcome to one of Windham's most impressive homes -- a majestic ranch built in 2021 that feels far grander than its 2-bedroom layout suggests. Set on a beautifully landscaped 3.94 acre parcel with room for gardens, play, or simply enjoying the peaceful setting, this home offers the perfect blend of luxury, comfort, and effortless living. Step inside to a soaring vaulted living room anchored by a striking stone fireplace. The chef's kitchen is a showstopper -- featuring a massive center island with elegant quartz countertops, a walk-in pantry, and seamless flow into the dining and living area. Hardwood floors flow throughout the main level, and oversized windows flood every room with natural light. The primary suite is a pure spa-like retreat: his-and-her walk-in closets, dual vanity areas, and a luxurious tiled shower. A second full bath offers a tiled tub/shower combo, with the convenient laundry room located just off the bath. Out back, relax on the rear porch overlooking an expansive patio and meticulously landscaped grounds -- the ideal setting for morning coffee, evening entertaining, or simply unwinding in your own private oasis. The nearly finished basement adds tremendous versatility with space ready for a family room, home gym, and office -- perfect for work-from-home flexibility or weekend fun. A 3-car garage completes the package, offering ample storage and an electric car charger. Just minutes to Portland, Sebago Lake, and all the lakes region has to offer, yet tucked away in serene privacy. This is country living at its finest -- elegant, low-maintenance, (irrigation for the luscious green lawn) and truly move-in ready. Don't miss this rare opportunity to own a one-of-a-kind ranch that truly feels like home.

Home Highlights

Parking

2 Car Garage

Outdoor

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$299

Listed

67 days ago

Home Details for 21 Cliff Drive

Active Status
MLS Status: Pending

Interior Features
Interior Details Basement: Doghouse,Interior Entry,Finished,FullNumber of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Dining Room, Exercise Room, Family Room, Kitchen, Laundry, Living Room, Mud Room
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 2976 Square Feet
Appliances & Utilities Utilities: Utilities OnAppliances: Dishwasher, Microwave, Gas Range, Refrigerator, Wall OvenDishwasherMicrowaveRefrigerator
Heating & Cooling Heating: Heat Pump,Space HeaterHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Tile, Hardwood
Levels, Entrance, & Accessibility Floors: Tile, Hardwood
View Has a ViewView: Trees/Woods

Exterior Features
Exterior Home Features Roof: Fiberglass ShinglePatio / Porch: Patio, PorchFoundation: Poured ConcreteNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Paved,5 - 10 Spaces,On Site,On Street
Frontage Road Frontage: Private RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer Sewer: Private Sewer, Septic Design Available
Finished Area Finished Area (above surface): 1976 Square FeetFinished Area (below surface): 1000 Square Feet

Days on Market
Days on Market: 67

Property Information
Year Built Year Built: 2021
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cottage,Ranch
Building Construction Materials: Wood Frame, Other, Vinyl Siding

Price & Status
Price List Price: $889,000Price Per Sqft: $299
Status Change & Dates Off Market Date: Sun Mar 15 2026

Media
See Virtual Tour

Location
Direction & Address City: Windham
School Information High School District: RSU 14

Agent Information
Listing Agent Listing ID: 1654107

Building
Building Area Building Area: 2976 Square Feet

Lot Information
Lot Area: 3.94 Acres

Energy
Energy Efficiency Features: Ceiling Fans

Miscellaneous
BasementMls Number: 1654107Above Grade Unfinished Area: 1976

Price History for 21 Cliff Drive

Date	Price	Event	Source
03/31/2026	$889,000	Pending	Maine Listings #1654107

03/17/2026	$889,000	Contingent	Maine Listings #1654107

03/13/2026	$889,000	Listed For Sale	Maine Listings #1654107

Similar Homes You May Like

Skip to last item

2.2 ACRES
$460,000
3 bd
1 ba
1,536 sqft
265 Windham Center Road,
Windham, ME 04062
Coldwell Banker Realty, Active
NEW CONSTRUCTION
$479,000
3 bd
2.5 ba
1,540 sqft
26 Dolley Farm Road #12,
Windham, ME 04062
The Flaherty Group, Active
2.23 ACRES
$619,000
5 bd
2 ba
2,209 sqft
64 Pope Road,
Windham, ME 04062
The Real Estate Store, Active
NEW CONSTRUCTION
0.69 ACRES
$599,000
3 bd
2 ba
1,717 sqft
18 Haven Road,
Windham, ME 04062
Maine Real Estate Experts, Active
$609,900
5 bd
2 ba
2,252 sqft
41 Lotts Drive,
Windham, ME 04062
Dream Home Realty LLC, Active
3.1 ACRES
$639,000
5 bd
2 ba
2,710 sqft
305 Gray Road,
Windham, ME 04062
The Maine Real Estate Experience, Active
NEW CONSTRUCTION
$609,000
2 bd
2.5 ba
1,958 sqft
16 Daybreak Ln,
Windham, ME 04062
Stillhill Development
NEW CONSTRUCTION
$850,000
3 bd
3 ba
2,400 sqft
22 Daybreak Ln,
Windham, ME 04062
Stillhill Development
NEW CONSTRUCTION
$699,000+
3 bd
2.5 ba
1,835 sqft
The Windham Plan in The Cove at Highland Lake,
Windham, ME 04062
Stillhill Development
NEW CONSTRUCTION
$589,000
2 bd
2.5 ba
1,958 sqft
6 Daybreak Ln,
Windham, ME 04062
Stillhill Development
NEW CONSTRUCTION
$699,000
3 bd
2.5 ba
1,850 sqft
23 Daybreak Ln,
Windham, ME 04062
Stillhill Development
NEW CONSTRUCTION
$599,000
2 bd
2.5 ba
1,958 sqft
6 Daybreak Lane #18,
Windham, ME 04062
Berkshire Hathaway HomeServices Verani Realty, Active
2.45 ACRES
$589,000
3 bd
2.5 ba
2,472 sqft
28 Adam Roberts Drive,
Windham, ME 04062
JC North East Real Estate, Active
OPEN TUE, 11-1PM
$619,000
2 bd
2.5 ba
1,958 sqft
14 Daybreak Lane #15,
Windham, ME 04062
Berkshire Hathaway HomeServices Verani Realty, Active
1.84 ACRES
$765,000
4 bd
2.5 ba
2,152 sqft
19 Treasure Lane,
Windham, ME 04062
EXP Realty, Active
OPEN TUE, 11-1PM
$699,000
2 bd
2.5 ba
1,832 sqft
25 Daybreak Lane #8,
Windham, ME 04062
Berkshire Hathaway HomeServices Verani Realty, Active
NEW CONSTRUCTION
0.7 ACRES
$1,150,000
4 bd
3.5 ba
2,350 sqft
17 Betty Lane,
Windham, ME 04062
Keller Williams Realty, Active
AUCTION
1.27 ACRES
Est. $1,122,000
4 bd
4 ba
3,413 sqft
6 Summit Ter,
Falmouth, ME 04105
0.73 ACRES
$889,000
3 bd
2.5 ba
2,600 sqft
32 Pennywhistle Drive,
Windham, ME 04062
Keller Williams Realty, Active
NEW CONSTRUCTION
1.03 ACRES
$874,900
3 bd
3 ba
2,856 sqft
23 Pennywhistle Drive,
Windham, ME 04062
Better Homes & Gardens Real Estate/The Masiello Group, Active
$458,000
3 bd
2 ba
1,662 sqft
1 Melrose Way #42,
Windham, ME 04062
Keller Williams Realty, Active
NEW CONSTRUCTION
$469,000
3 bd
2.5 ba
1,550 sqft
12 Dolley Farm Road #6,
Windham, ME 04062
The Flaherty Group, Active
NEW CONSTRUCTION
$474,000
3 bd
2.5 ba
1,550 sqft
6 Dolley Farm Road #3,
Windham, ME 04062
The Flaherty Group, Active
NEW CONSTRUCTION
$545,000
3 bd
2.5 ba
1,750 sqft
5 Shepherd Lane #11,
Windham, ME 04062
RE/MAX By The Bay, Active
NEW CONSTRUCTION
$517,500
3 bd
2 ba
1,632 sqft
6 Shepherd Lane #3,
Windham, ME 04103
RE/MAX By The Bay, Active
NEW CONSTRUCTION
$535,000
3 bd
2.5 ba
1,706 sqft
10 Shepherd Lane #5,
Windham, ME 04062
RE/MAX By The Bay, Active
4.7 ACRES
$680,000
3 bd
2.5 ba
3,036 sqft
315 River Road,
Windham, ME 04062
Maine Real Estate Experts, Active
4.25 ACRES
$1,025,000
4 bd
3 ba
2,976 sqft
183 Mountain Road,
Falmouth, ME 04105
Scott Sanford Realty, Active
NEW CONSTRUCTION
0.46 ACRES
$739,000
3 bd
2.5 ba
2,180 sqft
9 Dusty Rhoades Lane,
Windham, ME 04062
Salt Real Estate Co, Active
0.38 ACRES
$589,000
3 bd
2.5 ba
1,962 sqft
36 Belvedere Drive,
Windham, ME 04062
Redfin Corporation, Active
$699,900
3 bd
2.5 ba
2,224 sqft
36 Feldspar Lane #20,
Cumberland Center, ME 04021
Portside Real Estate Group, Active
$675,000
3 bd
2.5 ba
2,027 sqft
16 Feldspar Lane #26,
Cumberland Center, ME 04021
Portside Real Estate Group, Active
NEW CONSTRUCTION
$612,400
3 bd
2.5 ba
1,511 sqft
10 Feldspar Lane #28,
Cumberland, ME 04021
Portside Real Estate Group, Active
0.54 ACRES
$539,900
3 bd
2 ba
1,915 sqft
516 Falmouth Road,
Windham, ME 04062
Maine Real Estate Experts, Active
1.22 ACRES
$665,000
4 bd
2 ba
3,444 sqft
14 Emerson Drive,
Windham, ME 04062
Excellence Realty, Active
0.4 ACRES
$549,900
3 bd
2 ba
1,597 sqft
7 Preston Way,
Cumberland, ME 04021
Allied Real Estate, Active
5 ACRES
$985,000
3 bd
2.5 ba
2,327 sqft
38 Field Road,
Cumberland, ME 04021
Town & Shore Real Estate, Active
0.62 ACRES
$960,000
4 bd
2.5 ba
3,312 sqft
58 Hardy Road,
Falmouth, ME 04105
Keller Williams Realty, Active
OPEN SAT, 11-1PM
$899,000
4 bd
2.5 ba
2,304 sqft
1 Waxwing Lane #45,
Falmouth, ME 04105
Real Broker, Active
1.7 ACRES
$799,000
4 bd
2.5 ba
3,010 sqft
117 Blackstrap Road,
Falmouth, ME 04105
Century 21 North East, Active
See more homes for sale in
Windham
Take a look

Skip to first item

New Listings near 21 Cliff Drive

Skip to last item

2.45 ACRES
$589,000
3 bd
2.5 ba
2,472 sqft
28 Adam Roberts Drive,
Windham, ME 04062
JC North East Real Estate, Active
0.32 ACRES
$459,000
3 bd
2 ba
1,456 sqft
91 Vista Drive,
Windham, ME 04062
Keller Williams Realty, Active
4.25 ACRES
$1,025,000
4 bd
3 ba
2,976 sqft
183 Mountain Road,
Falmouth, ME 04105
Scott Sanford Realty, Active
NEW CONSTRUCTION
1.03 ACRES
$874,900
3 bd
3 ba
2,856 sqft
23 Pennywhistle Drive,
Windham, ME 04062
Better Homes & Gardens Real Estate/The Masiello Group, Active
2.2 ACRES
$460,000
3 bd
1 ba
1,536 sqft
265 Windham Center Road,
Windham, ME 04062
Coldwell Banker Realty, Active
5 ACRES
$985,000
3 bd
2.5 ba
2,327 sqft
38 Field Road,
Cumberland, ME 04021
Town & Shore Real Estate, Active
NEW CONSTRUCTION
0.69 ACRES
$599,000
3 bd
2 ba
1,717 sqft
18 Haven Road,
Windham, ME 04062
Maine Real Estate Experts, Active
$458,000
3 bd
2 ba
1,662 sqft
1 Melrose Way #42,
Windham, ME 04062
Keller Williams Realty, Active
0.54 ACRES
$539,900
3 bd
2 ba
1,915 sqft
516 Falmouth Road,
Windham, ME 04062
Maine Real Estate Experts, Active
4.7 ACRES
$680,000
3 bd
2.5 ba
3,036 sqft
315 River Road,
Windham, ME 04062
Maine Real Estate Experts, Active
0.73 ACRES
$889,000
3 bd
2.5 ba
2,600 sqft
32 Pennywhistle Drive,
Windham, ME 04062
Keller Williams Realty, Active
1.84 ACRES
$765,000
4 bd
2.5 ba
2,152 sqft
19 Treasure Lane,
Windham, ME 04062
EXP Realty, Active
3.1 ACRES
$639,000
5 bd
2 ba
2,710 sqft
305 Gray Road,
Windham, ME 04062
The Maine Real Estate Experience, Active
0.4 ACRES
$549,900
3 bd
2 ba
1,597 sqft
7 Preston Way,
Cumberland, ME 04021
Allied Real Estate, Active
0.38 ACRES
$589,000
3 bd
2.5 ba
1,962 sqft
36 Belvedere Drive,
Windham, ME 04062
Redfin Corporation, Active
See more homes for sale in
Windham
Take a look

Skip to first item

Property Tax and Assessment

Year	2024
Tax	$8,600
Assessment	$749,800

Home facts updated by county records

Comparable Sales for 21 Cliff Drive

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
16 Cliff Drive, Windham, ME	0.09	Single-Family Home	$800,000	01/30/26	3	2.5	2,232
284 Roosevelt Trail, Windham, ME	0.31	Single-Family Home	$600,000	07/21/25	4	2	2,100
31 Cooper Rdg Road, Windham, ME	0.14	Single-Family Home	$735,000	12/29/25	4	2.5	2,246
20 Balsam Lane, Windham, ME	0.68	Single-Family Home	$645,000	06/04/25	3	3	2,832
369 Windham Center Road, Windham, ME	0.49	Single-Family Home	$471,500	08/13/25	3	1.5	1,724
14 Stonebrook Road, Windham, ME	0.46	Single-Family Home	$660,000	07/02/25	3	2.5	2,685
6 Weeks Lane, Windham, ME	0.67	Single-Family Home	$780,000	09/18/25	3	2	2,028
4 Patriot Drive, Windham, ME	0.62	Single-Family Home	$575,000	05/07/26	3	2.5	1,866
56 POPLAR RIDGE Lane, Windham, ME	0.69	Single-Family Home	$583,000	09/19/25	4	3	3,446

Assigned Schools

These are the assigned schools for 21 Cliff 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
Flag
Charliestandishjr
Resident
4mo 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
Flag
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
4y 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
Flag
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
Flag
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
Flag

LGBTQ Local Legal Protections

The Flaherty Group

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

21 Cliff Drive, Windham, ME 04062 is a 2 bedroom, 2 bathroom, 2,976 sqft single-family home built in 2021. This property is currently available for sale and was listed by Maine Listings on Mar 13, 2026. The MLS # for this home is MLS# 1654107.

21 Cliff Drive
Windham, ME 04062

$889,000

$889,000

Local Information