55 Overlook Drive, Westbrook, ME 04092
Property image
Property image
SOLD
MAR 6, 2026

$731,400

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,324 sqft (on 0.60 acres)

55 Overlook Drive, Westbrook, ME 04092

Est. Refi. Payment $4,620/mo*
Refinance Your Home
Currently Off Market - Sold Mar 6, 2026 for $725,000 (12% above list price)

Home Value

Trulia Estimate
$731K
Since last month
Increased$700 (+0.1%)
Since last year
Increased$19K (+2.6%)
Since last sale
Increased$7K (+1%)
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 +96% in the last 10 years
MonthEstimated value
2026
September 2026$732K
August 2026$732K
July 2026$734K
June 2026$738K
May 2026$737K
April 2026$730K
March 2026$726K
February 2026$664K
January 2026$671K
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
717 Duck Pond Road, Westbrook, ME
0.16
Single-Family Home
$713,041
11/14/25
3
2.5
1,792
103 Mast Road, Westbrook, ME
0.41
Single-Family Home
$460,000
09/02/26
3
1.5
1,555
931 Duck Pond Road, Westbrook, ME
0.61
Single-Family Home
$529,000
10/24/25
4
2
2,362
471 Duck Pond Road, Westbrook, ME
0.56
Single-Family Home
$432,000
10/24/25
3
1.5
1,904
937 Duck Pond Road, Westbrook, ME
0.64
Single-Family Home
$501,000
02/26/26
3
2
2,074
87 Mast Road, Westbrook, ME
0.37
Single-Family Home
$415,000
10/24/25
3
1
1,292
28 Lillian Place, Westbrook, ME
0.82
Single-Family Home
$631,720
10/06/25
3
2
1,740
4 Nelsen Road, Westbrook, ME
0.87
Single-Family Home
$580,000
05/15/26
3
2
1,400
1033 Bridgton Road, Westbrook, ME
0.68
Single-Family Home
$480,000
06/25/26
2
2
1,664

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
152 Presidential Way, Westbrook, ME 04092
0.09
$1,141,700
5
5
5,322
Off Market
717 Duck Pond Road, Westbrook, ME 04092
0.16
$725,400
3
2.5
1,792
Off Market
155 Presidential Way, Westbrook, ME 04092
0.12
$820,000
3
3
2,480
For Sale
23 Peterson Road, Westbrook, ME 04092
0.26
$826,300
3
2
2,327
Off Market
35 Donalene Way, Westbrook, ME 04092
0.35
$989,000
5
3
3,024
For Sale
544 Duck Pond Road, Westbrook, ME 04092
0.42
$534,400
3
2
1,528
Off Market
87 Mast Road, Westbrook, ME 04092
0.37
$422,900
3
1
1,292
Off Market
824 Duck Pond Road, Westbrook, ME 04092
0.40
$738,200
3
2
1,788
Off Market
13 Ridge Road, Westbrook, ME 04092
0.44
$650,600
6
2
2,072
Off Market
103 Mast Road, Westbrook, ME 04092
0.41
$460,000
3
1.5
1,555
Recently Sold
844 Duck Pond Road, Westbrook, ME 04092
0.43
$614,700
5
2
2,076
Off Market

Local Information

  • Map ViewExplore the area around 55 Overlook Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
0.6 acre lot
2,324 sqft
$312/sqft
Garage
Last check for updates: about 21 hours ago
Listed by Keller Williams Realty
Bought with: Maine Real Estate Experts
Source: Maine Listings, MLS#1650676

About this House

Tucked into a highly sought-after and beautiful neighborhood, this well-loved 3-bedroom, 2.5-bath Colonial offers the kind of space and flexibility that adapts effortlessly to everyday life. From the moment you step inside, natural light and a thoughtful layout create a welcoming flow—equally suited for quiet evenings at home and lively gatherings with friends.

The main level features a comfortable living room centered around a fireplace, a sitting area that adds extra breathing room, and a well-kept kitchen with an island and stainless steel appliances that connects easily to the dining space. Step outside to the back deck and patio, where a large backyard provides room to relax, garden, or entertain on weekends. A half bath on the first floor adds everyday convenience, while the attached two-car garage and shed offer practical storage.

Upstairs, the primary bedroom feels like a true retreat with a private en suite bath and double sinks, joined by two additional bedrooms and a full bath. A generous bonus room expands the home's versatility—ideal for a media room, home office, play space, or additional lounge—while the full, unfinished basement offers exciting potential for future use.

The location brings it all together, with nearby trails and Highland Lake offering easy access to the outdoors, and Portland just minutes away when work, dining, or entertainment call. It's a natural balance of peaceful surroundings and everyday convenience—creating a setting that feels comfortable, connected, and easy to come home to.
55 Overlook Drive, Westbrook, ME 04092 is a 3 bedroom, 3 bathroom, 2,324 sqft single-family home built in 2004. It last sold for $725,000 on Mar 6, 2026 (12% above the $649,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $731,400, with a rent estimate of $3,858/month.

Home Details for 55 Overlook Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Doghouse,Interior EntryNumber of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2324 Square Feet
Heating & Cooling
Heating: Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Gas & Electric
Electric: Circuit Breakers, Generator Hookup, Underground
Windows, Doors, Floors & Walls
Flooring: Laminate, Tile, Wood
Levels, Entrance, & Accessibility
Floors: Laminate, Tile, Wood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, PatioOther Structures: Outbuilding, Shed(s)No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Private Sewer, Septic Tank
Finished Area
Finished Area (above surface): 2324 Square Feet

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial

Price & Status

Price
List Price: $649,000Price Per Sqft: $312/sqft
Status Change & Dates
Off Market Date: Wed Feb 04 2026

Location

Direction & Address
City: Westbrook

Building

Building Area
Building Area: 2324 Square Feet

Lot Information

Lot Area: 0.60 acres

Miscellaneous

BasementMls Number: 1650676Attribution Contact: scottandsunny@kw.comAbove Grade Unfinished Area: 2324

Price and Tax history

DateEventPrice
Mar 6, 2026
Source: Maine Listings #1650676
Sold
$725,000
Feb 5, 2026
Source: Maine Listings #1650676
Pending
$649,000
Jan 29, 2026
Source: Maine Listings #1650676
Listed For Sale
$649,000
Jul 26, 2013
Source: Maine Listings #1083662
Sold
$313,500
Jun 4, 2013
Source: Agent Provided
PriceChange
$319,000
Price decreased by 2%

Market trends in Westbrook

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$478K
$2.67KMoM
Sale-to-List Price
—
Price per sq ft
$346
$5MoM
Available listings
62
2MoM

Around this home

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

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 55 Overlook Drive

  • What is 55 Overlook Drive estimated to be worth?
    Trulia's estimated value for 55 Overlook Drive in Westbrook, ME is $731,400.
  • What is the price history for 55 Overlook Drive?
    55 Overlook Drive in Westbrook, ME last sold for $725,000 in March 2026.
  • 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 $478K. That is up $2.67K from the prior month.
  • How big is the lot at 55 Overlook Drive?
    The lot at 55 Overlook Drive in Westbrook, ME is about 0.60 acres (26,136 sq ft).
  • Does 55 Overlook Drive have a garage?
    Yes, 55 Overlook Drive in Westbrook, ME has a garage.

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