44 Oak Street, Westbrook, ME 04092
OFF MARKET

$666,400

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 3,180 sqft

44 Oak Street, Westbrook, ME 04092

Est. Refi. Payment $4,049/mo*
Refinance Your Home
Currently Off Market - Sold Sep 28, 2023 for $572,300

Home Value

Trulia Estimate
$666K
Since last month
Decreased$16K (-2.4%)
Since last year
Decreased$14K (-2%)
Since last sale
Increased$94K (+16.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +121% in the last 10 years
MonthEstimated value
2026
August 2026$666K
August 2026$666K
July 2026$683K
June 2026$700K
May 2026$692K
April 2026$698K
March 2026$691K
February 2026$686K
January 2026$660K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
107 Lamb Street, Westbrook, ME
0.20
Multi-Family Home
$590,000
06/01/26
4
2
2,452
199 Forest Street, Westbrook, ME
0.18
Multi-Family Home
$615,000
09/16/25
6
3
3,312
311 Main Street, Westbrook, ME
0.11
Multi-Family Home
$635,000
05/04/26
6
3
2,652
22 Berkeley Street, Westbrook, ME
0.13
Multi-Family Home
$280,000
06/03/26
4
2
2,507
22 Clifford Street, Westbrook, ME
0.11
Multi-Family Home
$512,000
05/19/26
3
2
1,438
39 Rochester Street, Westbrook, ME
0.34
Multi-Family Home
$801,000
06/18/26
6
3
4,168
20 Giles Street, Westbrook, ME
0.59
Multi-Family Home
$670,000
06/30/26
6
2
3,165
646 Main Street, Westbrook, ME
0.61
Multi-Family Home
$575,000
09/05/25
6
2
2,300
106 Haskell Street, Westbrook, ME
0.32
Multi-Family Home
$549,000
06/05/26
4
2
1,519
640 Main Street, Westbrook, ME
0.59
Multi-Family Home
$615,000
11/03/25
6
3
2,355

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
175 Mason Street, Westbrook, ME 04092
0.02
$803,400
4
3.5
2,768
Off Market
23 Waltham Street, Westbrook, ME 04092
0.05
$650,000
5
1.5
1,887
Recently Sold
16 Oak Street, Westbrook, ME 04092
0.07
$742,000
5
2.5
2,510
Off Market
123 Forest Street, Westbrook, ME 04092
0.06
$621,300
4
2
2,331
Off Market
330 Main Street, Westbrook, ME 04092
0.06
$541,700
4
1
2,033
Off Market
22 Clifford Street, Westbrook, ME 04092
0.11
$512,000
3
2
1,438
Recently Sold
64 Lamb Street, Westbrook, ME 04092
0.10
$1,005,000
9
5
4,507
Recently Sold
350 Main Street, Westbrook, ME 04092
0.07
$699,800
6
2.5
3,919
Off Market
0 Forest Street, Westbrook, ME 04092
0.12
-
-
-
-
Off Market
61 Lamb Street, Westbrook, ME 04092
0.12
$431,600
3
1
1,092
Off Market
331 Main Street, Westbrook, ME 04092
0.10
$694,900
5
4
3,136
Off Market

Local Information

  • Map ViewExplore the area around 44 Oak Street.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1900
Living Area
3,180 sqft
Price/Sqft
$210
Last check for updates: about 2 hours ago
Listed by Berkshire Hathaway HomeServices Verani Realty
Bought with: Portside Real Estate Group
Source: Maine Listings, MLS#1565106

About this House

Opportunity awaits! This charming building with period tin ceilings is a 2.9 unit building with unfinished work on the 3rd floor is ready for you to finish and rent out after inspections. This wonderful apartment building features mostly separated utilities, great location, plenty of old style charm and would make an great place to call home or have as an investment. The location here is key, close to Downtown, Rock Row, highways, Portland, Mall and supermarkets.
44 Oak Street, Westbrook, ME 04092 is a 5 bedroom, 2 bathroom, 3,180 sqft multi-family built in 1900. It last sold for $572,300 on Sep 28, 2023 (20% above the $477,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $666,400, with a rent estimate of $3,013/month.

Home Details for 44 Oak Street

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior Entry,Walk-Out Access,Full,Unfinished,Brick/Mortar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 3180 Square Feet
Appliances & Utilities
Utilities: Utilities On
Heating & Cooling
Heating: Hot Water,SteamNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Carpet, Laminate, Other, Tile, Vinyl, Wood
Levels, Entrance, & Accessibility
Stories: 3Number of Stories: 3Levels: Multi/SplitFloors: Carpet, Laminate, Other, Tile, Vinyl, Wood

Exterior Features

Exterior Home Features
Roof: Fiberglass Other ShinglePatio / Porch: PorchFoundation: Stone, Brick/MortarNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Common,Paved,Reclaimed,1 - 4 Spaces
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3180 Square Feet

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: New Englander,Other
Building
Construction Materials: Wood Frame, Vinyl Siding

Price & Status

Price
List Price: $477,000
Status Change & Dates
Off Market Date: Tue Jul 18 2023

Media

Location

Direction & Address
City: Westbrook

Building

Building Area
Building Area: 3180 Square Feet

Lot Information

Lot Area: 7840.8 sqft

Miscellaneous

BasementMls Number: 1565106Attribution Contact: (207)749-4699Above Grade Unfinished Area: 3180

Price and Tax history

DateEventPrice
Sep 28, 2023
Source: Maine Listings #1565106
Sold
$572,300
Jul 19, 2023
Source: Maine Listings #1565106
Pending
$477,000
Jul 13, 2023
Source: Maine Listings #1565106
Listed For Sale
$477,000

Market trends in Westbrook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$476K
$800MoM
Sale-to-List Price
—
Price per sq ft
$351
$18MoM
Available listings
64
8MoM

Around this home

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

LGBTQ Local Legal Protections

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

Frequently asked questions about 44 Oak Street

  • What is 44 Oak Street estimated to be worth?
    Trulia's estimated value for 44 Oak Street in Westbrook, ME is $666,400.
  • What is the price history for 44 Oak Street?
    44 Oak Street in Westbrook, ME last sold for $572,300 in September 2023.
  • Is Westbrook a buyer's or seller's market?
    Westbrook is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Westbrook?
    The median sale price in Westbrook is $476K. That is up $800 from the prior month.
  • Does 44 Oak Street have parking?
    Yes, 44 Oak Street in Westbrook, ME has on-site parking.
  • Is there a virtual tour of 44 Oak Street?
    Yes, a virtual tour of 44 Oak Street in Westbrook, ME is available.

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