Is Winter Harbor, ME dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Are there community events in Winter Harbor, ME?

As of early 2026, 100% of users say there are community events

Do residents of Winter Harbor, ME plan to stay at least 5 years?

As of early 2026, 100% of users say they plan to stay for at least 5 years

Is there wildlife in Winter Harbor, ME?

As of early 2026, 100% of users say there's wildlife

Is Winter Harbor, ME walkable to grocery stores?

As of early 2026, 100% of users say it's walkable to grocery stores

Is Winter Harbor, ME walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Would people walk alone at night in Winter Harbor, ME?

As of early 2026, 100% of users say people would walk alone at night

Does Winter Harbor, ME have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Are the streets well-lit in Winter Harbor, ME?

As of early 2026, 100% of users say streets are well-lit

Are yards well-kept in Winter Harbor, ME?

As of early 2026, 100% of users say yards are well-kept

Is parking easy in Winter Harbor, ME?

As of early 2026, 75% of users say parking is easy

Are neighbors friendly in Winter Harbor, ME?

As of early 2026, 57% of users say neighbors are friendly

Is a car needed in Winter Harbor, ME?

As of early 2026, 50% of users say car is needed

What is 396 Main St estimated to be worth?

Trulia's estimated value for 396 Main St in Winter Harbor, ME is $351,400 .

What is the price history for 396 Main St?

396 Main St in Winter Harbor, ME last sold for $225,000 in January 2021.

Is Winter Harbor a buyer's or seller's market?

Winter Harbor is currently a balanced market, based on recent for-sale activity.

What are the closest schools to 396 Main St?

The closest schools to 396 Main St in Winter Harbor, ME are Peninsula School (Pre-K/Elementary, rated 3/10), Sumner Memorial High School (rated 4/10), Sumner Middle School (rated 2/10).

How big is the lot at 396 Main St?

The lot at 396 Main St in Winter Harbor, ME is about 0.22 acres (9,583 sq ft).

Does 396 Main St have a garage?

Yes, 396 Main St in Winter Harbor, ME has a garage.

OFF MARKET

$351,400

Trulia Estimate

5 Beds
2.5 Baths
1,524 sqft

396 Main St, Winter Harbor, ME 04693

Est. Refi. Payment $2,175/mo*

Refinance Your Home

Currently Off Market - Sold Jan 26, 2021 for $225,000

Home Value

Trulia Estimate

$351K

Since last month

$6K (-1.5%)

Since last year

$3K (+0.7%)

Since last sale

$125K (+55.5%)

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

Month	Estimated value
2026
September 2026	$350K
August 2026	$355K
July 2026	$350K
June 2026	$352K
May 2026	$346K
April 2026	$350K
March 2026	$348K
February 2026	$336K
January 2026	$337K
2025
December 2025	$337K
November 2025	$340K
October 2025	$345K
September 2025	$347K
August 2025	$355K
July 2025	$349K
June 2025	$347K
May 2025	$353K
April 2025	$350K
March 2025	$340K
February 2025	$329K
January 2025	$333K
2024
December 2024	$338K
November 2024	$346K
October 2024	$343K
September 2024	$343K
August 2024	$352K
July 2024	$346K
June 2024	$351K
May 2024	$346K
April 2024	$337K
March 2024	$335K
February 2024	$323K
January 2024	$325K
2023
December 2023	$326K
November 2023	$336K
October 2023	$345K
September 2023	$346K
August 2023	$338K
July 2023	$345K
June 2023	$342K
May 2023	$338K
April 2023	$328K
March 2023	$319K
February 2023	$312K
January 2023	$313K
2022
December 2022	$314K
November 2022	$318K
October 2022	$320K
September 2022	$312K
August 2022	$304K
July 2022	$278K
June 2022	$277K
May 2022	$269K
April 2022	$268K
March 2022	$267K
February 2022	$264K
January 2022	$264K
2021
December 2021	$262K
November 2021	$248K
October 2021	$246K
September 2021	$245K
August 2021	$235K
July 2021	$234K
June 2021	$232K
May 2021	$231K
April 2021	$229K
March 2021	$228K
February 2021	$227K
January 2021	$225K
2020
December 2020	$226K
November 2020	$187K
October 2020	$184K
September 2020	$183K
August 2020	$182K
July 2020	$181K
June 2020	$180K
May 2020	$179K
April 2020	$179K
March 2020	$178K
February 2020	$178K
January 2020	$177K
2019
December 2019	$176K
November 2019	$175K
October 2019	$193K
September 2019	$193K
August 2019	$193K
July 2019	$194K
June 2019	$242K
May 2019	$240K
April 2019	$188K
March 2019	$194K
February 2019	$206K
January 2019	$218K
2018
December 2018	$196K
November 2018	$211K
October 2018	$213K
September 2018	$203K
August 2018	$212K
July 2018	$247K
June 2018	$244K
May 2018	$219K
April 2018	$186K
March 2018	$183K
February 2018	$183K
January 2018	$181K
2017
December 2017	$187K
November 2017	$179K
October 2017	$178K
September 2017	$180K
August 2017	$186K
July 2017	$180K
June 2017	$268K
May 2017	$269K
April 2017	$179K
March 2017	$177K
February 2017	$183K
January 2017	$184K
2016
December 2016	$183K
November 2016	$180K
October 2016	$174K
September 2016	$178K

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
45 Harbor Road, Winter Harbor, ME	0.17	Single-Family Home	$425,000	10/03/25	3	2	1,300
349 Main Street, Winter Harbor, ME	0.10	Single-Family Home	$560,000	10/01/25	4	1.5	4,000
29 Barnacle Lane, Winter Harbor, ME	0.56	Single-Family Home	$420,000	05/27/26	6	3	2,464
153 Deep Cove Road, Winter Harbor, ME	0.54	Single-Family Home	$850,000	10/10/25	3	2	1,600
103 Sargent Street, Winter Harbor, ME	0.53	Single-Family Home	$200,000	07/07/26	2	1.5	1,254
112 Hillcrest Drive, Winter Harbor, ME	0.74	Single-Family Home	$353,000	09/21/26	3	1	2,451
682 Newman Street, Winter Harbor, ME	1.73	Single-Family Home	$228,500	11/26/25	2	1.5	1,200
454 Summer Harbor Road, Winter Harbor, ME	1.59	Single-Family Home	$485,000	12/17/25	2	2	1,176
59 Island View Drive, Gouldsboro, ME	2.22	Single-Family Home	$1,205,000	08/24/26	2	2	1,496
743 S Gouldsboro Road, Gouldsboro, ME	3.00	Single-Family Home	$290,000	05/12/26	3	1.5	1,960

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
430 Main Street, Winter Harbor, ME 04693	0.08	$1,595,000	6	4.5	4,074	For Sale
25 Belleview Avenue, Winter Harbor, ME 04693	0.08	$389,000	4	2	2,248	For Sale
358 Main Street, Winter Harbor, ME 04693	0.07	$578,900	4	2.5	1,925	Off Market
349 Main Street, Winter Harbor, ME 04693	0.10	$581,400	4	1.5	4,000	Off Market
335 Main Street, Winter Harbor, ME 04693	0.12	$396,600	4	3	2,160	Off Market
22 Harbor Road, Winter Harbor, ME 04693	0.12	$325,000	3	2	1,932	Off Market
0 Summer Harbor Road, Winter Harbor, ME 04693	0.20	-	-	-	-	Off Market
45 Harbor Road, Winter Harbor, ME 04693	0.17	$441,200	3	2	1,300	Off Market
74 Grindstone Avenue, Winter Harbor, ME 04693	0.30	$536,000	3	2	2,130	Off Market
72 Misty Harbor Drive #A2, Winter Harbor, ME 04693	0.30	$228,000	2	1.5	1,084	Recently Sold
72 Misty Harbor Drive #A7, Winter Harbor, ME 04693	0.31	$187,600	2	1.5	1,108	Off Market
42 Bunker Road, Winter Harbor, ME 04693	0.33	$388,300	3	2	1,840	Off Market

Local Information

Map ViewExplore the area around 396 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1900

1,524 sqft

$231/sqft

Garage

About this House

This single-family home is located at 396 Main St, Winter Harbor, ME. 396 Main St is in Winter Harbor, ME and in ZIP code 04693. This property has 5 bedrooms, 3 bathrooms and approximately 1,524 sqft of floor space. This property has a lot size of 9583 sqft and was built in 1900.

396 Main St, Winter Harbor, ME 04693 is a 5 bedroom, 3 bathroom, 1,524 sqft single-family home built in 1900. It last sold for $225,000 on Jan 26, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $351,400, with a rent estimate of $2,373/month.

Home Details for 396 Main St

Interior Features
Heating & Cooling Heating: Baseboard, OilHeating Fuel: Baseboard

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: Single Family Home

Rental Terms, Policies & Fees
Furnished

Exterior Features
Exterior Home Features PatioPorch
Parking & Garage GarageParking Spaces: 2Parking: Garage Detached

Lot Information
Lot Area: 9583 sqft

Price and Tax history

Date	Event	Price
Jan 26, 2021 Source: Maine Listings #1478274	Sold	$225,000
Dec 21, 2020 Source: Agent Provided	Pending	$235,000
Dec 16, 2020 Source: Agent Provided	Listed For Sale	$235,000
Nov 22, 2019 Source: Maine Listings #1412566	Sold	$175,000
Jul 29, 2019 Source: Agent Provided	PriceChange	$199,000 Price decreased by 20%
May 2, 2019 Source: Agent Provided	Listed For Sale	$249,000

Year	Property tax	Tax assessment
2024	$2,226	$154,600

Additional Cost

Market trends in Winter Harbor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Peninsula School
PK-5
Public
65 Students
Regional School Unit 24
3/10
GreatSchools Rating
Parent Rating Average
No reviews available for this school.

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 Winter Harbor

At least 1 Trulia users voted on each feature.

100 % Say it's dog friendly
100 % Say there are community events
100 % Say they plan to stay for at least 5 years
100 % Say there's wildlife
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say people would walk alone at night
100 % Say there are sidewalks
100 % Say streets are well-lit
100 % Say yards are well-kept
75 % Say parking is easy
57 % Say neighbors are friendly
50 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.

gaia188
14y ago
"This area has it all....... If you love nature and crashing ocean look no further."
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Frequently asked questions about 396 Main St

What is 396 Main St estimated to be worth?
Trulia's estimated value for 396 Main St in Winter Harbor, ME is $351,400.
What is the price history for 396 Main St?
396 Main St in Winter Harbor, ME last sold for $225,000 in January 2021.
Is Winter Harbor a buyer's or seller's market?
Winter Harbor is currently a balanced market, based on recent for-sale activity.
What are the closest schools to 396 Main St?
The closest schools to 396 Main St in Winter Harbor, ME are Peninsula School (Pre-K/Elementary, rated 3/10), Sumner Memorial High School (rated 4/10), Sumner Middle School (rated 2/10).
How big is the lot at 396 Main St?
The lot at 396 Main St in Winter Harbor, ME is about 0.22 acres (9,583 sq ft).
Does 396 Main St have a garage?
Yes, 396 Main St in Winter Harbor, ME has a garage.

Apartments for Rent

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$100/mo
1-2 bd
1 ba
Mill Stream Heights | 20 Hillcrest Dr,
Winter Harbor, ME 04693
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Winter Harbor
Take a look

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Off Market Homes Near 396 Main St

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SOLD
SEP 21, 2026
$353,000
3 bd
1 ba
2,451 sqft
112 Hillcrest Drive,
Winter Harbor, ME 04693
Portside Real Estate Group
SOLD
AUG 31, 2026
$450,000
56 Jordan Harbor Road,
Winter Harbor, ME 04693
Realty of Maine
SOLD
JUL 7, 2026
$200,000
2 bd
1.5 ba
1,254 sqft
103 Sargent Street,
Winter Harbor, ME 04693
Realty of Maine
SOLD
MAY 27, 2026
$420,000
6 bd
3 ba
2,464 sqft
29 Barnacle Lane,
Winter Harbor, ME 04693
Realty of Maine
SOLD
MAY 12, 2026
$290,000
3 bd
1.5 ba
1,960 sqft
743 S Gouldsboro Road,
Gouldsboro, ME 04607
Better Homes & Gardens Real Estate/The Masiello Group
SOLD
MAR 13, 2026
$225,000
2 bd
1 ba
1,108 sqft
61 Misty Harbor Drive #B8,
Winter Harbor, ME 04693
The Winter Harbor Agency
SOLD
DEC 17, 2025
$485,000
2 bd
2 ba
1,176 sqft
454 Summer Harbor Road,
Winter Harbor, ME 04693
NextHome Experience
SOLD
DEC 12, 2025
$350,000
2 bd
1 ba
768 sqft
23 Bullfrog Cove Road,
Gouldsboro, ME 04607
The Maine Real Estate Experience
SOLD
DEC 8, 2025
$314,000
2 bd
0.5 ba
1,200 sqft
143 Main Street,
Gouldsboro, ME 04607
Realty of Maine
SOLD
DEC 3, 2025
$228,000
2 bd
1.5 ba
1,084 sqft
72 Misty Harbor Drive #A2,
Winter Harbor, ME 04693
Legacy Properties Sotheby's International Realty
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Winter Harbor
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Homes for sale near 396 Main St

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1 ACRE
$389,000
4 bd
2 ba
2,248 sqft
25 Belleview Avenue,
Winter Harbor, ME 04693
Portside Real Estate Group
0.42 ACRES
$550,000
5 bd
4 ba
2,634 sqft
20 Rand Lane,
Winter Harbor, ME 04693
Legacy Properties Sotheby's International Realty
0.78 ACRES
$1,595,000
6 bd
4.5 ba
4,074 sqft
430 Main Street,
Winter Harbor, ME 04693
The Christopher Group, LLC
0.25 ACRES
$389,000
1 bd
1 ba
630 sqft
102 Sargent Street,
Winter Harbor, ME 04693
NextHome Experience
1.15 ACRES
$1,495,000
4 bd
4 ba
2,341 sqft
16 Steamboat Lane,
Winter Harbor, ME 04693
The Christopher Group, LLC
0.48 ACRES
$234,900
2 bd
1 ba
2,508 sqft
43 Duck Pond Road,
Winter Harbor, ME 04693
Beal Realty
2.9 ACRES
$3,595,000
5 bd
5 ba
6,398 sqft
72 Jordan Harbor Road,
Winter Harbor, ME 04693
LandVest, Inc.
0.42 ACRES
$239,000
3 bd
1 ba
1,120 sqft
22 Crane Road,
Winter Harbor, ME 04693
The Winter Harbor Agency
20 ACRES
$2,200,000
3 bd
4 ba
3,676 sqft
800 Summer Harbor Road,
Winter Harbor, ME 04693
Legacy Properties Sotheby's International Realty
0.94 ACRES
$399,000
4 bd
1 ba
2,300 sqft
9 Rice Road (Birch Harbor),
Birch Harbor, ME 04613
First Choice Real Estate
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Winter Harbor
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