21 Lookout Drive, Freeport, ME 04032
Property image
Property image
OFF MARKET

$1,305,000

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 3,805 sqft (on 2.90 acres)

21 Lookout Drive, Freeport, ME 04032

Refinance Your Home
Currently Off Market - Sold Jun 20, 2025 for $1,270,000

Home Value

Trulia Estimate
$1.3M
Since last month
Decreased$5K (-0.4%)
Since last year
Increased$34K (+2.6%)
Since last sale
Increased$35K (+2.8%)
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 +113% in the last 10 years
MonthEstimated value
2026
August 2026$1.31M
August 2026$1.3M
July 2026$1.31M
June 2026$1.32M
May 2026$1.32M
April 2026$1.31M
March 2026$1.3M
February 2026$1.28M
January 2026$1.29M
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
40 Primrose Lane, Freeport, ME
0.25
Single-Family Home
$1,469,400
06/30/26
5
3
4,910
2 Harbor Ridge Road, Freeport, ME
0.55
Single-Family Home
$1,060,000
03/20/26
3
4
2,581
15 Harbor Ridge Road, Freeport, ME
0.59
Single-Family Home
$1,000,000
09/16/25
2
2.5
1,511
3 Randall Road, Freeport, ME
0.88
Single-Family Home
$1,300,000
09/10/25
3
3
2,624
29 South Freeport Road, Freeport, ME
0.98
Single-Family Home
$1,239,000
04/29/26
3
2
2,112
39 Hunter Road, Freeport, ME
1.35
Single-Family Home
$850,000
04/06/26
3
2.5
2,736
67 S Freeport Road, Freeport, ME
0.80
Single-Family Home
$949,000
07/21/26
2
2
2,068
62 Webster Road, Freeport, ME
1.75
Single-Family Home
$955,000
04/09/26
4
2.5
2,310
4 Sandy Beach Road, Freeport, ME
1.08
Single-Family Home
$715,000
11/24/25
4
2
1,441
62 South Street, Freeport, ME
1.35
Single-Family Home
$940,000
07/02/26
3
2
2,773

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
6 Ship View Lane, Chebeague Island, ME 04017
0.11
$1,253,900
3
2.5
3,220
Off Market
23 Lookout Drive, Freeport, ME 04032
0.08
$1,200,300
4
3.5
2,824
Off Market
40 Primrose Lane, Freeport, ME 04032
0.25
$1,469,400
5
3
4,910
Recently Sold
32 Bristol Road, Freeport, ME 04032
0.30
$1,016,900
4
3.5
2,756
Off Market
5 Goodrich Drive, Freeport, ME 04032
0.30
$949,100
4
2.5
2,368
Off Market
14 Stagecoach Road, Freeport, ME 04032
0.30
$365,600
2
1
756
Off Market
30 Pine Street, Freeport, ME 04032
0.37
$910,200
4
3
2,779
Off Market
36 Pine Street, Freeport, ME 04032
0.41
$477,600
3
1.5
1,164
Off Market
0 Harbor Ridge Road, Freeport, ME 04032
0.49
-
-
-
-
Off Market
2 Harbor Ridge Road, Freeport, ME 04032
0.55
$1,060,000
3
4
2,581
Recently Sold
3 Hayden Lane #3, Freeport, ME 04032
0.51
$595,500
4
3.5
1,772
Off Market

Local Information

  • Map ViewExplore the area around 21 Lookout Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
2.9 acre lot
3,805 sqft
$343/sqft
2 Car Garage
HOA $83/mo
Last check for updates: about 5 hours ago
Listed by Town & Shore Real Estate
Bought with: Portside Real Estate Group
Source: Maine Listings, MLS#1622264

About this House

Extraordinary 5 bedroom, 4 bath home in the desirable Winston Hill neighborhood! Sited on 3 acres of privacy and tranquility, yet a stone's throw to all conveniences. Superb construction and layout! Three floors of living space including mudroom, laundry room, eat-in kitchen, formal living and dining, family room with brick fireplace, and a large bonus room with endless potential! Incredible opportunity in this location!
21 Lookout Drive, Freeport, ME 04032 is a 5 bedroom, 4 bathroom, 3,805 sqft single-family home built in 2001. It last sold for $1,270,000 on Jun 20, 2025 (2% above the $1,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,305,000, with a rent estimate of $4,421/month.

Home Details for 21 Lookout Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior Entry,Full,UnfinishedNumber of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bonus Room, Dining Room, Family Room, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3805 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Gas Range, Refrigerator, Wall Oven, WasherDishwasherDryerLaundry: SinkRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,ZonedNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Double Pane WindowsFlooring: Tile, Wood
Levels, Entrance, & Accessibility
Floors: Tile, Wood
View
Has a ViewView: Trees/Woods
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PorchOther Structures: Shed(s)No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved,1 - 4 Spaces,Garage Door Opener
Frontage
Road Frontage: Private RoadNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 3805 Square Feet

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Farmhouse
Building
Construction Materials: Wood Frame, Clapboard, Wood Siding

Price & Status

Price
List Price: $1,250,000
Status Change & Dates
Off Market Date: Sun May 18 2025

Location

Direction & Address
City: Freeport
School Information
High School District: RSU 05

Building

Building Area
Building Area: 3805 Square Feet

HOA

Has an HOAHOA Fee: $1,000/Annually

Lot Information

Lot Area: 2.9 Acres

Miscellaneous

BasementMls Number: 1622264Attribution Contact: 207-773-0262Above Grade Unfinished Area: 3805

Price and Tax history

DateEventPrice
Jun 20, 2025
Source: Maine Listings #1622264
Sold
$1,270,000
May 30, 2025
Source: Maine Listings #1622264
Pending
$1,250,000
May 21, 2025
Source: Maine Listings #1622264
Contingent
$1,250,000
May 14, 2025
Source: Maine Listings #1622264
Listed For Sale
$1,250,000

Market trends in Freeport

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
30
7MoM

Around this home

What Locals Say about Freeport

At least 22 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 93 % Say car is needed

  • 77 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 75 % Say people would walk alone at night

  • 74 % Say kids play outside

  • 73 % Say there's holiday spirit

  • 71 % Say parking is easy

  • 63 % Say they plan to stay for at least 5 years

  • 61 % Say it's quiet

  • 56 % Say neighbors are friendly

  • 41 % Say there are community events

  • 39 % Say it's walkable to restaurants

  • 38 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mq2bxdyydh
    "LL bean and town of Freeport have a lot of family friendly events throughout the year. Christmas fall Summer camps Farmers market Art walks Community center "
    0
    Flag
  • Tia Silverio
    "My specific neighborhood is on a main road and my specific house is also an entrance to a public park, so people come flying down the road once in a while "
    0
    Flag
  • Kristyn.marzilli
    "Friendly neighbors, and several connecting neighborhoods. Everyone seems to maintain their yards as well, and it’s beautiful to see, especially in spring and summer."
    3
    Flag
  • Vincent M.
    "15 minute ride to Portland with little to no traffic. 30 minutes to Lewiston and 15 minutes to Brunswick "
    0
    Flag
  • Trulia User
    "People have particular parties for holidays and invite the neighbors. Halloween brings children from All neighborhoods because SouthbFrerpirt is charming, safe, and walkable"
    1
    Flag
  • Taxidog
    "I am not a parent so couldn’t tell other parents what is important about Freeport. For all people, it is a safe, welcoming town. "
    0
    Flag
  • Kathy G.
    "Freeport is a safe community that's close to the best that Maine has to offer. The ocean, lakes and mountains. Plus, it's just 25 miles away from Portland."
    0
    Flag
  • ArmenianAmerican
    "This is the best area of Freeport because it gives you the experience of living in the picturesque beauty of Maine; yet only a few minutes from downtown with the closest access to the hwy."
    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 21 Lookout Drive

  • What is 21 Lookout Drive estimated to be worth?
    Trulia's estimated value for 21 Lookout Drive in Freeport, ME is $1,305,000.
  • What is the price history for 21 Lookout Drive?
    21 Lookout Drive in Freeport, ME last sold for $1,270,000 in June 2025.
  • Is Freeport a buyer's or seller's market?
    Freeport is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Freeport?
    Residents describe Freeport, ME as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Freeport, ME.
  • Does 21 Lookout Drive have laundry facilities?
    Yes, 21 Lookout Drive in Freeport, ME has in-unit laundry.
  • How big is the lot at 21 Lookout Drive?
    The lot at 21 Lookout Drive in Freeport, ME is about 2.9 acres.

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