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

55 Overlook Drive
Westbrook, ME 04092

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

$725,000

Last Sold: Mar 6, 2026
12% over list $649K
$312/sqft

$725,000

Last Sold: Mar 6, 2026
12% over list $649K
$312/sqft
3 Beds
2.5 Baths
2,324 sqft
(on 0.60 acres)

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
Last check for updates: about 3 hours ago
Listed by Keller Williams Realty
Bought with: Maine Real Estate Experts
Source: Maine Listings, MLS#1650676

Description

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). It is currently off market. The Trulia Estimate is $738,300, with a rent estimate of $3,660/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
$312/sqft
Listed
166 days ago

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 History for 55 Overlook Drive

DatePriceEventSource
03/06/2026$725,000Sold
Maine Listings #1650676
02/05/2026$649,000PendingMaine Listings #1650676
01/29/2026$649,000Listed For SaleMaine Listings #1650676
07/26/2013$313,500Sold
Maine Listings #1083662
06/04/2013$319,000PriceChange
Agent Provided
04/26/2013$324,000PriceChange
Agent Provided
03/19/2013$329,000Listed For SaleAgent Provided
01/17/2011$349,000ListingRemovedAgent Provided
07/19/2010$349,000Listed For SaleAgent Provided

Market trends in Westbrook

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
56
4MoM
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Property Tax and Assessment

Year2024
Tax$7,353
Assessment$440,800
Home facts updated by county records

Comparable Sales for 55 Overlook Drive

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
824 Duck Pond Road, Westbrook, ME
0.40
Single-Family Home
$720,000
07/25/25
3
2
1,788
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
455 Duck Pond Road, Westbrook, ME
0.60
Single-Family Home
$432,000
08/18/25
2
2
1,764
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

Nearby homes

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Assigned Schools

These are the assigned schools for 55 Overlook Drive.
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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Explore by feature - Pet Friendly

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Homes for sale near 55 Overlook Drive

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Off Market Homes Near 55 Overlook Drive

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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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