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

OFF MARKET

255 Main St
Winter Harbor, ME 04693

2 Beds
2 Baths
1,403 sqft

$497,600

Trulia Estimate

as of Jul 16, 2026

$497,600

Trulia Estimate

as of Jul 16, 2026

2 Beds

2 Baths

1,403 sqft

Local Information

Map ViewExplore the area around 255 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 255 Main St, Winter Harbor, ME. 255 Main St is in Winter Harbor, ME and in ZIP code 04693. This property has 2 bedrooms, 2 bathrooms and approximately 1,403 sqft of floor space. This property has a lot size of 3485 sqft and was built in 1970.

255 Main St, Winter Harbor, ME 04693 is a 2 bedroom, 2 bathroom, 1,403 sqft single-family home built in 1970. It last sold for $375,000 on May 28, 2021. It is currently off market. The Trulia Estimate is $497,600, with a rent estimate of $2,097/month.

Home Highlights

Parking

No Info

Outdoor

Porch, Patio, Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 255 Main St

Interior Features
Heating & Cooling Heating: Baseboard, Propane ButaneHeating Fuel: Baseboard

Property Information
Year Built Year Built: 1970
Property Type / Style Property Type: Single Family Home

Rental Terms, Policies & Fees
Furnished

Exterior Features
Exterior Home Features DeckPatioPorch

Lot Information
Lot Area: 3484 sqft

Price History for 255 Main St

Date	Price	Event	Source
05/28/2021	$375,000	Sold	Maine Listings #1421267
Recording Date 05/28/2021 County Transfer Tax N/A Total Transfer Tax N/A
09/19/2011	$325,000	Sold	Maine Listings #938593
Recording Date 09/19/2011 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Winter Harbor

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

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Property Tax and Assessment

Year	2024
Tax	$3,521
Assessment	$244,500

Home facts updated by county records

Comparable Sales for 255 Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
45 Harbor Road, Winter Harbor, ME	0.28	Single-Family Home	$425,000	10/03/25	3	2	1,300
349 Main Street, Winter Harbor, ME	0.22	Single-Family Home	$560,000	10/01/25	4	1.5	4,000
29 Barnacle Lane, Winter Harbor, ME	0.27	Single-Family Home	$420,000	05/27/26	6	3	2,464
103 Sargent Street, Winter Harbor, ME	0.33	Single-Family Home	$200,000	07/07/26	2	1.5	1,254
153 Deep Cove Road, Winter Harbor, ME	0.76	Single-Family Home	$850,000	10/10/25	3	2	1,600
454 Summer Harbor Road, Winter Harbor, ME	1.66	Single-Family Home	$485,000	12/17/25	2	2	1,176
682 Newman Street, Winter Harbor, ME	1.61	Single-Family Home	$228,500	11/26/25	2	1.5	1,200
16 Crane Road, Winter Harbor, ME	1.82	Single-Family Home	$140,000	09/03/25	1	1	504
143 Main Street, Gouldsboro, ME	3.00	Single-Family Home	$314,000	12/08/25	2	0.5	1,200
743 S Gouldsboro Road, Gouldsboro, ME	2.94	Single-Family Home	$290,000	05/12/26	3	1.5	1,960

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $521,600
4 bd
2 ba
2,064 sqft
310 Main Street,
Winter Harbor, ME 04693
Better Homes & Gardens Real Estate/The Masiello Group, Closed
OFF MARKET
0 Newman Street,
Winter Harbor, ME 04693
The Winter Harbor Agency, Closed
OFF MARKET
Est. $211,300
2 bd
1.5 ba
1,024 sqft
73 Misty Harbor Drive #D7,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $255,500
3 bd
1.5 ba
1,344 sqft
73 Misty Harbor Drive #B4,
Winter Harbor, ME 04693
Realty of Maine, Closed
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, Closed
OFF MARKET
Est. $229,000
2 bd
1.5 ba
1,330 sqft
72 Misty Harbor Drive #A8,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $188,500
2 bd
1.5 ba
1,108 sqft
72 Misty Harbor Drive #A7,
Winter Harbor, ME 04693
Realty of Maine, Closed
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, Closed
OFF MARKET
Est. $237,300
3 bd
1.5 ba
1,344 sqft
73 Misty Harbor Drive #B3,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $196,300
2 bd
1.5 ba
1,024 sqft
73 Misty Harbor Drive #B2,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $238,000
2 bd
1.5 ba
1,108 sqft
27 Misty Harbor Drive #D1,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $304,000
3 bd
1.5 ba
1,200 sqft
39 Newman Street,
Winter Harbor, ME 04693
First Choice Real Estate, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 255 Main St.

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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Apartments for Rent

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$100/mo
1-2 bd
1 ba
Mill Stream Heights | Hillcrest Dr,
Winter Harbor, ME 04693
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Winter Harbor
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Homes for sale near 255 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, Active
0.42 ACRES
$595,000
5 bd
4 ba
2,634 sqft
20 Rand Lane,
Winter Harbor, ME 04693
Legacy Properties Sotheby's International Realty, Active
0.25 ACRES
$399,000
1 bd
1 ba
630 sqft
102 Sargent Street,
Winter Harbor, ME 04693
NextHome Experience, Active
2.3 ACRES
$375,000
3 bd
1 ba
2,451 sqft
112 Hillcrest Drive,
Winter Harbor, ME 04693
Portside Real Estate Group, Active
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, Active
7.92 ACRES
$485,000
3 bd
1.5 ba
1,680 sqft
161 Birch Harbor Road,
Winter Harbor, ME 04693
NextHome Experience, Active
2.3 ACRES
$1,350,000
4 bd
3.5 ba
3,250 sqft
29 Loons Call,
Winter Harbor, ME 04693
Portside Real Estate Group, Active
NEW CONSTRUCTION
1.5 ACRES
$1,199,900
2 bd
2 ba
1,496 sqft
59 Island View Drive,
Gouldsboro, ME 04607
NextHome Experience, Active
20 ACRES
$2,400,000
3 bd
4 ba
3,676 sqft
800 Summer Harbor Road,
Winter Harbor, ME 04693
Legacy Properties Sotheby's International Realty, Active
1.51 ACRES
$210,000
2 bd
1 ba
1,200 sqft
747 S Gouldsboro Road,
Gouldsboro, ME 04607
NextHome Experience, Active
See more homes for sale in
Winter Harbor
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Off Market Homes Near 255 Main St

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SOLD
JUL 3, 2026
$380,000
3 bd
2 ba
1,760 sqft
799 Pond Road,
Gouldsboro, ME 04607
Realty of Maine, Closed
SOLD
MAY 27, 2026
$420,000
6 bd
3 ba
2,464 sqft
29 Barnacle Lane,
Winter Harbor, ME 04693
Realty of Maine, Closed
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, Closed
SOLD
DEC 17, 2025
$485,000
2 bd
2 ba
1,176 sqft
454 Summer Harbor Road,
Winter Harbor, ME 04693
NextHome Experience, Closed
SOLD
DEC 12, 2025
$350,000
2 bd
1 ba
768 sqft
23 Bullfrog Cove Road,
Gouldsboro, ME 04607
The Maine Real Estate Experience, Closed
SOLD
DEC 8, 2025
$314,000
2 bd
0.5 ba
1,200 sqft
143 Main Street,
Gouldsboro, ME 04607
Realty of Maine, Closed
SOLD
OCT 3, 2025
$425,000
3 bd
2 ba
1,300 sqft
45 Harbor Road,
Winter Harbor, ME 04693
Realty of Maine, Closed
SOLD
OCT 1, 2025
$560,000
4 bd
1.5 ba
4,000 sqft
349 Main Street,
Winter Harbor, ME 04693
Realty of Maine, Closed
OFF MARKET
Est. $508,700
8 bd
5 ba
4,200 sqft
763 S Gouldsboro Road,
Gouldsboro, ME 04607
Realty of Maine, Closed
See more homes for sale in
Winter Harbor
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255 Main St
Winter Harbor, ME 04693

$497,600

$497,600

Local Information