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 29 Navy Dr estimated to be worth?

Trulia's estimated value for 29 Navy Dr in Winter Harbor, ME is $324,400 .

What is the price history for 29 Navy Dr?

29 Navy Dr in Winter Harbor, ME last sold for $149,000 in December 2012.

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

Winter Harbor is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 29 Navy Dr?

The closest schools to 29 Navy Dr 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 29 Navy Dr?

The lot at 29 Navy Dr in Winter Harbor, ME is about 0.25 acres (10,890 sq ft).

OFF MARKET

$324,400

Trulia Estimate

4 Beds
2 Baths
1,146 sqft (on 0.25 acres)

29 Navy Dr, Winter Harbor, ME 04693

Est. Refi. Payment $1,950/mo*

Refinance Your Home

Currently Off Market - Sold Dec 21, 2012 for $149,000

Home Value

Trulia Estimate

$324K

Since last month

$8K (-2.5%)

Since last year

$8K (+2.4%)

Since last sale

$175K (+117.7%)

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 +24% in the last 10 years

Month	Estimated value
2026
August 2026	$324K
July 2026	$333K
June 2026	$340K
May 2026	$326K
April 2026	$312K
March 2026	$303K
February 2026	$303K
January 2026	$298K
2025
December 2025	$269K
November 2025	$292K
October 2025	$314K
September 2025	$311K
August 2025	$317K
July 2025	$314K
June 2025	$322K
May 2025	$324K
April 2025	$317K
March 2025	$309K
February 2025	$300K
January 2025	$278K
2024
December 2024	$292K
November 2024	$298K
October 2024	$331K
September 2024	$324K
August 2024	$332K
July 2024	$318K
June 2024	$330K
May 2024	$320K
April 2024	$312K
March 2024	$297K
February 2024	$290K
January 2024	$290K
2023
December 2023	$301K
November 2023	$304K
October 2023	$352K
September 2023	$365K
August 2023	$349K
July 2023	$366K
June 2023	$341K
May 2023	$262K

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	0.55	Single-Family Home	$425,000	10/03/25	3	2	1,300
29 Barnacle Lane, Winter Harbor, ME	0.20	Single-Family Home	$420,000	05/27/26	6	3	2,464
349 Main Street, Winter Harbor, ME	0.47	Single-Family Home	$560,000	10/01/25	4	1.5	4,000
103 Sargent Street, Winter Harbor, ME	0.51	Single-Family Home	$200,000	07/07/26	2	1.5	1,254
153 Deep Cove Road, Winter Harbor, ME	0.84	Single-Family Home	$850,000	10/10/25	3	2	1,600
682 Newman Street, Winter Harbor, ME	1.36	Single-Family Home	$228,500	11/26/25	2	1.5	1,200
454 Summer Harbor Road, Winter Harbor, ME	1.53	Single-Family Home	$485,000	12/17/25	2	2	1,176
16 Crane Road, Winter Harbor, ME	1.85	Single-Family Home	$140,000	09/03/25	1	1	504
59 Island View Drive, Gouldsboro, ME	2.01	Single-Family Home	$1,205,000	08/24/26	2	2	1,496
681 S Gouldsboro Road, Gouldsboro, ME	2.98	Single-Family Home	$150,000	03/23/26	3	1.5	1,600

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
64 Navy Drive, Winter Harbor, ME 04693	0.02	$315,100	3	2	1,146	Off Market
108 Newman Street, Winter Harbor, ME 04693	0.03	$352,900	3	2	1,616	Off Market
22 Navy Drive, Winter Harbor, ME 04693	0.04	$320,400	2	2	1,774	Off Market
A1 Misty Harbor Drive #A1, Winter Harbor, ME 04693	0.11	$227,100	2	1.5	1,100	Off Market
73 Misty Harbor #D8, Winter Harbor, ME 04693	0.13	$249,000	2	1.5	1,108	For Sale
73 Misty Harbor Drive #D2, Winter Harbor, ME 04693	0.14	$206,100	2	1.5	1,024	Off Market
73 Misty Harbor Drive #A6, Winter Harbor, ME 04693	0.14	$201,200	3	1.5	1,042	Off Market
27 Misty Harbor Drive #D-6, Winter Harbor, ME 04693	0.14	$226,500	3	1.5	1,344	Off Market
39 Newman Street, Winter Harbor, ME 04693	0.15	$297,600	3	1.5	1,200	Off Market
27 Misty Harbor Drive #D1, Winter Harbor, ME 04693	0.18	$231,200	2	1.5	1,108	Off Market
73 Misty Harbor Drive #B2, Winter Harbor, ME 04693	0.18	$196,400	2	1.5	1,024	Off Market
73 Misty Harbor Drive #B3, Winter Harbor, ME 04693	0.18	$236,100	3	1.5	1,344	Off Market

Local Information

Map ViewExplore the area around 29 Navy Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1958

Lot Size

0.25 acres

Living Area

1,146 sqft

Price/Sqft

$283

About this House

4 Bdrm cape in the village. Owner has made some great upgrades. Taken out part of dining room wall to make it more of an open floor plan. Built in Entertainment center, and upgraded basement, gas stove in living room.Schoodic Point is a few miles away.

29 Navy Dr, Winter Harbor, ME 04693 is a 4 bedroom, 2 bathroom, 1,146 sqft single-family home built in 1958. It last sold for $149,000 on Dec 21, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $324,400, with a rent estimate of $2,068/month.

Home Details for 29 Navy Dr

Property Information
Year Built Year Built: 1958
Property Type / Style Property Type: Single Family Home

Interior Features
Fireplace & Spa Fireplace

Lot Information
Lot Area: 10890 sqft

Price and Tax history

Date	Event	Price
Dec 21, 2012 Source: Maine Listings #1045021	Sold	$149,000
Oct 24, 2012 Source: Agent Provided	Listed For Sale	$167,000

Additional Cost

Market trends in Winter Harbor

Last updated July 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 29 Navy Dr

What is 29 Navy Dr estimated to be worth?
Trulia's estimated value for 29 Navy Dr in Winter Harbor, ME is $324,400.
What is the price history for 29 Navy Dr?
29 Navy Dr in Winter Harbor, ME last sold for $149,000 in December 2012.
Is Winter Harbor a buyer's or seller's market?
Winter Harbor is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 29 Navy Dr?
The closest schools to 29 Navy Dr 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 29 Navy Dr?
The lot at 29 Navy Dr in Winter Harbor, ME is about 0.25 acres (10,890 sq ft).

Apartments for Rent

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

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Off Market Homes Near 29 Navy Dr

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SOLD
JUL 7, 2026
$200,000
2 bd
1.5 ba
1,254 sqft
103 Sargent Street,
Winter Harbor, ME 04693
Realty of Maine, Closed
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
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
SOLD
JAN 15, 2026
$344,000
12-45 Pond Rd,
Gouldsboro, ME 04607
Coastal Maine Realty,LLC, 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
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
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Winter Harbor
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Homes for sale near 29 Navy Dr

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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, Active
1 ACRE
$389,000
4 bd
2 ba
2,248 sqft
25 Belleview Avenue,
Winter Harbor, ME 04693
Portside Real Estate Group, Active
0.25 ACRES
$399,000
1 bd
1 ba
630 sqft
102 Sargent Street,
Winter Harbor, ME 04693
NextHome Experience, Active
0.48 ACRES
$234,900
2 bd
1 ba
2,508 sqft
43 Duck Pond Road,
Winter Harbor, ME 04693
Beal Realty, 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
NEW - 17 HRS AGO
1.15 ACRES
$1,495,000
4 bd
4 ba
2,341 sqft
16 Steamboat Lane,
Winter Harbor, ME 04693
The Christopher Group, LLC, Active
0.42 ACRES
$239,000
3 bd
1 ba
1,120 sqft
2 Crane Road,
Winter Harbor, ME 04693
The Winter Harbor Agency, Active
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, Active
0.94 ACRES
$449,000
4 bd
1 ba
2,300 sqft
9 Rice Road (Birch Harbor),
Birch Harbor, ME 04613
First Choice Real Estate, Active
0.39 ACRES
$359,900
8 bd
5 ba
2,600 sqft
6 Mitchell Lane,
Gouldsboro, ME 04607
Realty of Maine, Active
See more homes for sale in
Winter Harbor
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