44 Oak Street, Westbrook, ME 04092
OFF MARKET

44 Oak Street
Westbrook, ME 04092

  • 5 Beds
  • 2 Baths
  • 3,180 sqft

$699,700

Trulia Estimate
as of Jul 6, 2026

$699,700

Trulia Estimate
as of Jul 6, 2026
5 Beds
2 Baths
3,180 sqft

Local Information

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

Description

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). It is currently off market. The Trulia Estimate is $699,700, with a rent estimate of $2,642/month.

Home Highlights

Parking
No Info
Outdoor
Porch
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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 History for 44 Oak Street

DatePriceEventSource
09/28/2023$572,300Sold
Maine Listings #1565106
07/19/2023$477,000PendingMaine Listings #1565106
07/13/2023$477,000Listed For SaleMaine Listings #1565106

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$7,296
Assessment$437,400
Home facts updated by county records

Comparable Sales for 44 Oak Street

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
546 Main Street, Westbrook, ME
0.40
Multi-Family Home
$707,000
07/21/25
4
3.5
2,922

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Oak Street.
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 Oak Street

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Off Market Homes Near 44 Oak Street

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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.
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