39 Dutton Hill Rd, Windham, ME 04062
OFF MARKET

39 Dutton Hill Rd
Windham, ME 04062

  • 4 Beds
  • 2 Baths
  • 2,128 sqft (on 4.95 acres)

$733,600

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $4,303/mo*
Refinance Your Home

$733,600

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $4,303/mo*
Refinance Your Home
4 Beds
2 Baths
2,128 sqft
(on 4.95 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome to that home you've been searching for! This 1997 Cape Cod is situated on 4.95 acres of rolling landscape and scenic views. On a clear day you can gaze upon the crest of Mt. Washington right from your front porch! You will first notice the ample parking to accommodate guests for get-togethers, or even park a couple of RVs without giving up your own outdoor spaces. When you enter through the front porch entryway you will be greeted with a semi-formal dining area that flows into the open concept kitchen and great room. The updated kitchen includes custom cabinetry, granite countertops complete with a center island to gather with friends. You can then slide on into the great room and warm up for conversation or relaxation by the wood burning fireplace that is constructed of stones gathered from the property! The first level also includes a guest bedroom and 3/4 guest bathroom as well as a media/entertainment room. On the second level you'll find the spacious primary suite with a large walk-in closet, two more bedrooms and an updated full bath. Ample space for protected parking in the attached 2 car garage with enormous storage area overhead that could also be finished for a recreation area. Note: This home is listed with the town as a 4 bedroom, and has a 3 bedroom septic design. OPEN HOUSES APRIL 30TH FROM 11AM-1PM MAY 1ST FROM 11AM-2PM!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 39 Dutton Hill Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 4.95 acres

Price History for 39 Dutton Hill Rd

DatePriceEventSource
06/02/2022$600,500Sold
PrimeMLS #4907315
05/04/2022$485,000PendingBerkshire Hathaway HomeServices Verani Realty #4907315
05/03/2022$485,000ContingentPrimeMLS #4907315
05/03/2022$485,000PendingMaine Listings #1526332
04/28/2022$485,000Listed For SaleMaine Listings #1526332
09/12/2009$132,000ListingRemovedAgent Provided
08/13/2009$132,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$7,203
Assessment$628,000
Home facts updated by county records

Comparable Sales for 39 Dutton Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
25 Arrowhead Pass, Windham, ME
0.45
Single-Family Home
$550,000
09/12/25
3
2
1,792
7 Dogleg Drive, Windham, ME
0.99
Single-Family Home
$560,000
09/10/25
4
4
2,888
622 Methodist Road, Westbrook, ME
0.94
Single-Family Home
$375,000
07/17/25
3
2
1,586
1 Alweber Road, Windham, ME
1.16
Single-Family Home
$480,000
09/30/25
3
2
2,020
410 Small Hardy Road, Westbrook, ME
0.96
Single-Family Home
$437,750
11/14/25
2
1.5
1,180
471 Methodist Road, Westbrook, ME
1.18
Single-Family Home
$670,000
08/08/25
4
3
2,632
289 Highland Cliff Road, Windham, ME
1.04
Single-Family Home
$725,000
11/21/25
3
2.5
2,728
12 Merrill Road, Westbrook, ME
1.39
Single-Family Home
$482,000
11/25/25
3
1.5
1,512
5 Mayfield Dr, Westbrook, ME
1.40
Single-Family Home
$625,000
01/15/26
3
2
1,728
620 Cumberland Street, Westbrook, ME
1.77
Single-Family Home
$585,000
02/17/26
3
4
2,450

Assigned Schools

These are the assigned schools for 39 Dutton Hill Rd.
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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

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"
    0
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  • 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 "
    0
    Flag
  • Charliestandishjr
    "I love living here. It’s safe and nice to look at.Dead end street no through traffic. "
    0
    Flag
  • 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"
    0
    Flag
  • 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. "
    1
    Flag
  • 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."
    0
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  • 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. "
    13
    Flag
  • Lizmc200
    "I love everything about Windham. The people are great and the town has everything you need in it. "
    0
    Flag
  • 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."
    2
    Flag
  • 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 "
    1
    Flag
  • zmbailey
    "If you don't have a car, do not move here. Air is relatively clean though."
    0
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  • 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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39 Dutton Hill Rd, Windham, ME 04062 is a 4 bedroom, 2 bathroom, 2,128 sqft single-family home built in 1997. This property is not currently available for sale. 39 Dutton Hill Rd was last sold on Jun 2, 2022 for $600,500. The current Trulia Estimate for 39 Dutton Hill Rd is $733,600.