44 Chestnut St, Westbrook, ME 04092
Property image
Property image
OFF MARKET

44 Chestnut St
Westbrook, ME 04092

  • 4 Beds
  • 2 Baths
  • 1,231 sqft

$463,300

Trulia Estimate
as of Jul 8, 2026

$463,300

Trulia Estimate
as of Jul 8, 2026
4 Beds
2 Baths
1,231 sqft

Local Information

  • Map ViewExplore the area around 44 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 44 Chestnut St, Westbrook, ME. 44 Chestnut St is in Westbrook, ME and in ZIP code 04092. This property has 4 bedrooms, 2 bathrooms and approximately 1,231 sqft of floor space. This property has a lot size of 7405 sqft and was built in 1957.
44 Chestnut St, Westbrook, ME 04092 is a 4 bedroom, 2 bathroom, 1,231 sqft single-family home built in 1957. It last sold for $260,000 on Aug 30, 2019. It is currently off market. The Trulia Estimate is $463,300, with a rent estimate of $3,164/month.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 44 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: Baseboard, Stove, Oil, Wood PelletHeating Fuel: Baseboard

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other

Property Information

Year Built
Year Built: 1957Year Updated: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

Price History for 44 Chestnut St

DatePriceEventSource
08/30/2019$260,000Sold
Maine Listings #1418895
08/23/2019$269,900PendingAgent Provided
08/20/2019$269,900PendingToActiveAgent Provided
07/31/2019$269,900PendingAgent Provided
07/29/2019$269,900PriceChange
Agent Provided
07/15/2019$279,900PriceChange
Agent Provided
06/25/2019$289,000PriceChange
Agent Provided
06/10/2019$299,000Listed For SaleAgent Provided
06/26/2015$205,000Sold
Maine Listings #1206596
03/14/2015$209,900Listed For SaleAgent Provided
10/31/2014$229,900ListingRemovedAgent Provided
06/10/2014$229,900Listed For SaleAgent Provided

Market trends in Westbrook

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
52
6MoM
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Property Tax and Assessment

Year2024
Tax$3,973
Assessment$238,200
Home facts updated by county records

Comparable Sales for 44 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Kennard Street, Westbrook, ME
0.08
Single-Family Home
$480,000
04/09/26
4
2
1,512
182 Myrtle Street, Westbrook, ME
0.23
Single-Family Home
$459,900
08/08/25
4
1.5
1,948
70 Myrtle Street, Westbrook, ME
0.30
Single-Family Home
$415,250
07/16/25
3
2
1,170
13 Bremen Street, Westbrook, ME
0.19
Single-Family Home
$450,000
09/22/25
3
1.5
1,280
86 King Street, Westbrook, ME
0.26
Single-Family Home
$465,000
07/02/26
3
1.5
940
154 Myrtle Street, Westbrook, ME
0.20
Single-Family Home
$375,000
12/18/25
4
1
1,792
262 Bridge Street, Westbrook, ME
0.19
Single-Family Home
$385,000
05/29/26
4
1
1,374
77 Pierce Street, Westbrook, ME
0.20
Single-Family Home
$480,000
10/28/25
3
1.5
1,578
110 Myrtle Street, Westbrook, ME
0.25
Single-Family Home
$490,000
12/10/25
3
1.5
1,396
76 Kennard Street, Westbrook, ME
0.11
Single-Family Home
$460,000
05/08/26
2
1
1,260

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Chestnut St.
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 Westbrook

At least 110 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say parking is easy

  • 80 % Say car is needed

  • 77 % Say kids play outside

  • 76 % Say there are sidewalks

  • 74 % Say yards are well-kept

  • 73 % Say it's walkable to restaurants

  • 71 % Say there's holiday spirit

  • 65 % Say people would walk alone at night

  • 61 % Say it's walkable to grocery stores

  • 61 % Say streets are well-lit

  • 59 % Say there's wildlife

  • 55 % Say neighbors are friendly

  • 55 % Say it's quiet

  • 50 % Say they plan to stay for at least 5 years

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Heidi T.
    "Fires, cocktail hour, picnics, park, Drouin dance center, frog and turtle, good kids in my neighborhood for my kids to play with"
    2
    Flag
  • Abkiphone
    "Just outside of the metro area. Main arteries of transportation are all nearby. Easy commute and still outside the city without being too far."
    1
    Flag
  • Angeliquekundiro
    "It’s a great place to live, but I would say when it comes to transportation.. the buses can run longer later in the day in Walker street. Work end late, people need to commute from work to home later hours as the other last bus runs. "
    2
    Flag
  • Kelly.donovan94
    "Not a great neighborhood. We have experienced auto theft before. Very odd disoriented people wondering around at night. Very VERY noisy neighbors. "
    6
    Flag
  • Tylercross033
    "I live in the neighborhood neighbors are friendly and respectful I love it here A lot of good people"
    0
    Flag
  • Lisa D.
    "I don’t know much about he school system because I don’t have kids. There is a neighborhood feel to our city."
    0
    Flag
  • Stvhrrs1
    "It’s a nice neighborhood. It has a brand new school being built. It’s an easy walk to downtown Westbrook. There are nice restaurants in town "
    1
    Flag
  • Danielle G.
    "it has a lot around easy to walk to alot of places, it also has a lot of poke stops for the pokemon go game that alot of people play "
    1
    Flag
  • Gizmoeks
    "It is a quiet unknown street just on the outside of town with families and one of the oldest houses in Westbrook! The streets in the area are named after family members of the man who still lives in the house. "
    1
    Flag
  • Gizmoeks
    "There are several families with children and pets. There is a sense of community but also respect of privacy. "
    0
    Flag
  • William W. S.
    "Up and coming community and new river walk and a changing the town town. The neighborhood is a work in progress"
    0
    Flag
  • Sarah19beth
    "Everyone is so friendly!! It’s always felt like a safe place to live. Cars travel at a good speed and everyone greets each other "
    0
    Flag
  • Kfbackman
    "I've lived in this neighborhood for 10 years. It's safe and most people are friendly. convenient location and a mix of people. Also it is within walking distance to shops. "
    0
    Flag

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Homes for sale near 44 Chestnut St

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Off Market Homes Near 44 Chestnut St

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