23 Grassington Rd, Windham, ME 04062
Property image
Property image
OFF MARKET

23 Grassington Rd
Windham, ME 04062

  • 3 Beds
  • 1 Bath
  • 1,450 sqft

$876,800

Trulia Estimate
as of Jul 6, 2026

$876,800

Trulia Estimate
as of Jul 6, 2026
3 Beds
1 Bath
1,450 sqft

Local Information

  • Map ViewExplore the area around 23 Grassington Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

PRICE LOWERED ON WINTER RENTAL (AVAILABLE DEC 2025 until JUNE 2026).

If interested please complete the "about me" renter information or submit an application. You can also message me the information if easier / preferred.

Wonderfully situated in Windham ME on Little Sebago Lake, this year round home offers open concept living with floor to ceiling windows overlooking Brown Cove. Arguably one of the best lots on the lake, property has a beautiful, level yard perfect for entertaining and enjoying the outdoors in all seasons.

The property includes 3 bedrooms and 1 bathroom, it's an ideal choice for small families seeking a cozy winter stay. Enjoy views of Little Sebago Lake from the comfort of your living room in the fall, winter, and spring seasons.

Features include long owned water frontage with private dock and panoramic views of the lake, a new back deck, a newly renovated bathroom, new water filtration system, new monitor propane heater, and two heats pumps for heat/ac. With an ideal location on the south end of the Little Sebago, this home has great proximity to Portland (approx 15-20 min drive). This property comes furnished (see living room and bedroom photos), but certain furniture pieces can be removed if needed. We are seeking a renter immediately that can rent starting in September 2025 through May 2026. Dates are somewhat flexible.

We prefer renters without pets, but we understand that furry friends are part of the family and we'll consider an exception. Please note that only one pet is allowed, and additional fees may apply

This property is available to rent during the fall and winter months, running from mid September through the end of May (approx 8 months). It has a Septic & Well Water system so there are no utility costs for water or sewage. Renter will be responsible for Heat (propane + two heat pumps), Electricity, and Cable/Internet. Owner/Lessor will pay for snow removal on road and driveway.
23 Grassington Rd, Windham, ME 04062 is a 3 bedroom, 1 bathroom, 1,450 sqft single-family home. It last sold for $405,000 on May 29, 2020 (22,400% above the $1,800 asking price). More recently, it was listed as a rental in August 2025 with an asking price of $2,500 per month. That rental listing was removed on January 9, 2026. It is currently off market. The Trulia Estimate is $876,800, with a rent estimate of $2,885/month.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 23 Grassington Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Tile
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price History for 23 Grassington Rd

DatePriceEventSource
01/09/2026$1,800ListingRemovedZillow Rentals
11/28/2025$1,800PriceChange
Zillow Rentals
10/30/2025$1,850PriceChange
Zillow Rentals
10/16/2025$1,950PriceChange
Zillow Rentals
09/29/2025$2,000PriceChange
Zillow Rentals
09/21/2025$2,200PriceChange
Zillow Rentals
09/08/2025$2,300PriceChange
Zillow Rentals
08/22/2025$2,500Listed For RentZillow Rentals
09/30/2024$2,200ListingRemovedZillow Rentals
09/25/2024$2,200Listed For RentZillow Rentals
09/16/2024$2,350ListingRemovedZillow Rentals
09/09/2024$2,350PriceChange
Zillow Rentals
09/02/2024$2,400PriceChange
Zillow Rentals
08/27/2024$2,500PriceChange
Zillow Rentals
08/23/2024$2,550PriceChange
Zillow Rentals
08/14/2024$2,650Listed For RentZillow Rentals
12/12/2023ListingRemovedZillow Rentals
11/17/2023$2,000PriceChange
Zillow Rentals
11/02/2023$2,100PriceChange
Zillow Rentals
10/16/2023$2,300PriceChange
Zillow Rentals
10/02/2023$2,450PriceChange
Zillow Rentals
09/02/2023$2,600Listed For RentZillow Rentals
03/13/2023ListingRemovedZillow Rentals
12/13/2022$2,200PriceChange
Zillow Rentals
11/23/2022$2,400Listed For RentZillow Rental Manager
05/29/2020$405,000Sold
Maine Listings #1447845
08/09/2013$286,500Sold
Maine Listings #1084867

Market trends in Windham

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
56
6
MoM
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Property Tax and Assessment

Year2024
Tax$9,917
Assessment$864,600
Home facts updated by county records

Comparable Sales for 23 Grassington Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.35
Single-Family Home
$430,000
09/17/25
3
1
1,314
0.31
Single-Family Home
$435,000
12/22/25
3
1
1,861
0.43
Single-Family Home
$422,200
09/12/25
3
1
1,416
0.44
Single-Family Home
$415,000
09/22/25
3
1
1,570
0.42
Single-Family Home
$410,000
06/29/26
3
1
1,037
0.29
Single-Family Home
$457,000
02/20/26
3
2
1,554
0.20
Single-Family Home
$479,800
10/09/25
3
2
2,052
0.56
Single-Family Home
$450,000
05/01/26
3
1
1,380
0.60
Single-Family Home
$470,000
05/20/26
3
1
1,624
0.43
Single-Family Home
$475,000
06/26/26
3
1.5
1,326

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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