Is South Portland, ME dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Is parking easy in South Portland, ME?

As of early 2026, 87% of users say parking is easy

Are yards well-kept in South Portland, ME?

As of early 2026, 81% of users say yards are well-kept

Is a car needed in South Portland, ME?

As of early 2026, 80% of users say car is needed

Does South Portland, ME have sidewalks?

As of early 2026, 75% of users say there are sidewalks

Would people walk alone at night in South Portland, ME?

As of early 2026, 75% of users say people would walk alone at night

Do kids play outside in South Portland, ME?

As of early 2026, 74% of users say kids play outside

Does South Portland, ME show holiday spirit?

As of early 2026, 73% of users say there's holiday spirit

Is South Portland, ME walkable to restaurants?

As of early 2026, 70% of users say it's walkable to restaurants

Are neighbors friendly in South Portland, ME?

As of early 2026, 62% of users say neighbors are friendly

Is there wildlife in South Portland, ME?

As of early 2026, 60% of users say there's wildlife

Do residents of South Portland, ME plan to stay at least 5 years?

As of early 2026, 58% of users say they plan to stay for at least 5 years

Are the streets well-lit in South Portland, ME?

As of early 2026, 58% of users say streets are well-lit

Is South Portland, ME walkable to grocery stores?

As of early 2026, 55% of users say it's walkable to grocery stores

Is South Portland, ME quiet?

As of early 2026, 54% of users say it's quiet

Are there community events in South Portland, ME?

As of early 2026, 26% of users say there are community events

FOR SALE

0.7 ACRES

5 Chestnut Street
Vinalhaven, ME 04863

3 Beds
2 Baths
1,900 sqft (on 0.70 acres)

$729,000

3 Beds

2 Baths

1,900 sqft

(on 0.70 acres)

Local Information

Map ViewExplore the area around 5 Chestnut Street.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: about 2 hours ago

Listing courtesy of Davidson Realty

Source: Maine Listings, MLS#1670675

Also Listed on Maine Listings.

Description

Built by Reuben Carver c.1790 and sold only a few years later to David Vinal, a member of one of Vinalhaven's founding families, this beautifully preserved center-chimney Cape offers a rare opportunity to own an important piece of the island's early history. Thoughtfully expanded around 1800, the home has been meticulously maintained by the current owners while preserving the warmth, craftsmanship, and character that define Maine's earliest homes.
Inside, original architectural details remain remarkably intact, including fireplaces in both the living and dining rooms, original mantels and moldings, and wood floors. Modern improvements have been carefully integrated to provide year-round comfort, including thermo pane windows, a forced hot air heating system, updated electrical, and spray-foam insulation around the basement perimeter for improved energy efficiency.
The home includes a flexible floor plan well suited for today's lifestyle, with a first-floor bedroom, two beautifully renovated bathrooms, a welcoming eat-in kitchen with a charming walk-in pantry and small wood stove, two second-floor bedrooms in the north wing, and two seasonal guest bedrooms within the original Cape.
Equally remarkable is the property's expansive village lot--an uncommon size that provides privacy and room to enjoy established perennial gardens, mature landscaping, and generous open lawn. The grounds offer abundant space for gardening, recreation, or simply relaxing in a peaceful setting just moments from village amenities.
Complementing the home is an impressive collection of outbuildings, including a substantial barn with an attached open woodshed, a classic 1½-story storage shed currently used as a studio, and an additional one-story shed, providing abundant space for hobbies, workshops, gardening equipment, and storage.
The historic Vinal Homestead offers a rare blend of early New England architecture, modern comfort, impeccable care, and one of the most generous in-town lots

Home Highlights

Parking

Garage

Outdoor

Patio, Deck

A/C

Heating only

HOA

None

Price/Sqft

$384

Listed

13 days ago

Home Details for 5 Chestnut Street

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Doghouse,Interior Entry,Walk-Out Access,Partial,UnfinishedNumber of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Laundry, Living Room, Office
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 1900 Square Feet
Appliances & Utilities Utilities: Utilities OnAppliances: Gas Range, RefrigeratorRefrigerator
Heating & Cooling Heating: Forced Air,Other,Wood StoveNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Window: Double Pane WindowsFlooring: Carpet, Tile, Vinyl, Wood
Levels, Entrance, & Accessibility Floors: Carpet, Tile, Vinyl, Wood
View Has a ViewView: Scenic

Exterior Features
Exterior Home Features Roof: Fiberglass ShinglePatio / Porch: Deck, PatioOther Structures: Outbuilding, Shed(s), Barn(s)Foundation: Block, Stone, GraniteNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Gravel,1 - 4 Spaces,Detached
Frontage Not on Waterfront
Water & Sewer Sewer: Private Sewer, Septic TankWater Body: Carver's Pond
Finished Area Finished Area (above surface): 1900 Square Feet

Days on Market
Days on Market: 13

Property Information
Year Built Year Built: 1790
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod,New Englander
Building Construction Materials: Wood Frame, Clapboard, Wood Siding

Price & Status
Price List Price: $729,000Price Per Sqft: $384

Location
Direction & Address City: Vinalhaven
School Information High School District: RSU 08/MSAD 08

Agent Information
Listing Agent Listing ID: 1670675

Building
Building Area Building Area: 1900 Square Feet

Lot Information
Lot Area: 0.70 acres

Miscellaneous
BasementMls Number: 1670675Above Grade Unfinished Area: 1900

Market trends in South Portland

Last updated June 2026

Avg. sale price

$515K

Sale-to-List Price

100.3%

Price per sq ft

$394

Available listings

1MoM

Price History for 5 Chestnut Street

Date	Price	Event	Source
07/07/2026	$729,000	Listed For Sale	Maine Listings #1670675

06/27/2026	$749,000	ListingRemoved	Maine Listings #1628353

05/06/2026	$749,000	Listed For Sale	Maine Listings #1628353

11/06/2025	$775,000	ListingRemoved	Maine Listings #1628353

06/27/2025	$775,000	Listed For Sale	Maine Listings #1628353

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Year	2024
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Comparable Sales for 5 Chestnut Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
38 Latham Street, South Portland, ME	0.40	Single-Family Home	$510,000	08/21/25	3	1.5	1,501
107 Elm Street, South Portland, ME	0.10	Single-Family Home	$555,000	08/26/25	4	2.5	2,100
33 Kelley Street, South Portland, ME	0.29	Single-Family Home	$653,000	02/05/26	4	1.5	1,504
23 Cole Street, South Portland, ME	0.29	Single-Family Home	$660,000	03/31/26	3	2.5	1,668
11 Chestnut Street, South Portland, ME	0.01	Single-Family Home	$399,900	01/30/26	4	1	1,100
42 Reynolds Street, South Portland, ME	0.38	Single-Family Home	$515,000	12/11/25	4	2	1,742
486 Highland Avenue, South Portland, ME	0.77	Single-Family Home	$605,000	06/25/26	3	2.5	1,833
37 Shelby Lane, South Portland, ME	0.58	Single-Family Home	$776,000	07/02/26	4	2	2,526
18 Elmwood Avenue, South Portland, ME	0.50	Single-Family Home	$505,000	04/22/26	3	1.5	1,346
32 Robinson Street, South Portland, ME	0.24	Single-Family Home	$490,000	06/18/26	3	1	1,040

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Skip to first item

Assigned Schools

These are the assigned schools for 5 Chestnut Street.

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 South Portland

At least 149 Trulia users voted on each feature.

94 % Say it's dog friendly
87 % Say parking is easy
81 % Say yards are well-kept
80 % Say car is needed
75 % Say there are sidewalks
75 % Say people would walk alone at night
74 % Say kids play outside
73 % Say there's holiday spirit
70 % Say it's walkable to restaurants
62 % Say neighbors are friendly
60 % Say there's wildlife
58 % Say they plan to stay for at least 5 years
58 % Say streets are well-lit
55 % Say it's walkable to grocery stores
54 % Say it's quiet
26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Tammy Walter
Resident
1y ago
"Terrible. Public transportation is just awful around here. It’s terrible. You cannot get around without a car which makes life difficult difficult."
0
Flag
Melissa Doughty
Resident
2y ago
"Many people walk their dogs, kids ride their bikes, people drive too fast through the neighborhood though. "
0
Flag
Kyle Glowacky
Resident
2y ago
"Quiet but close to city. This neighborhood allows one to feel separate from the hustle and bustle but able to get there without commuting to far."
2
Flag
Sonia Z.
Resident
5y ago
"I use my own car to get everywhere, people is very respectful and follow the rules when driving. I just love a lot South Portland. Everything is so close by"
1
Flag
Jaycyr1
Resident
6y ago
"It’s a friendly community, great location to the ocean or to hiking. Convenient to restaurants & entertainment. Pretty friendly community."
1
Flag
Bowie414
Resident
6y ago
"Schools are nearby, and lots of families live in the area. Kids love to hang at the beach and play on the playgrounds"
0
Flag
Bowie414
Resident
6y ago
"Easier than most towns around Portland, traffic can increase during rush hours. Maybe a 15 commute at the worst to South Portland. Public transportation is easy and accessible."
0
Flag
Bmccauley
Prev. Resident
6y ago
"I’ve lived in this neighborhood for 16 years & it’s a great community. Everyone watches out for everyone’s kids, houses, etc. I feel safe & know that my neighbors would do anything for us as we would do the same for them!"
5
Flag
Jenn J.
Resident
6y ago
"It is an incredibly friendly neighborhood and I feel very safe walking at night alone, which is my favorite part!"
2
Flag
Bmccauley
Resident
7y ago
"Our neighborhood is large but we’re also close to so many things...shopping, highways, the old port!"
2
Flag
Jenn J.
Resident
7y ago
"I live on a busy street with lots of nighttime foot traffic. Even still, I feel more safe here than I did in several cities I've lived in previously! I have street parking and have never once seen anyone so much as peer in my windows, even in the middle of the night. I used to watch this very carefully to get an idea for if it was safe enough to leave stuff in my car...and I've not had to monitor it at all anymore! I've never had packages stolen, my neighbors have let me use their driveways during parking bans, and we all keep an eye out for each other (even though we don't know one another too well). This neighborhood has treated me very well."
0
Flag
Anita B.
Resident
7y ago
"It’s a very safe place. No strange people walking around or violence. No animals and people. Very good place to raise a child. "
0
Flag
Mroberts
Resident
7y ago
"Wide range of ages live in the neighborhood with families with youngsters to late teens. Overall a progressive and accepting community. Walking distance to a great family beach and with an extensive walking/biking path. Movies at big light in the summers and evening live music in the park. A great community center with a pool and a great pre-k program and affordable and fun summer camps."
0
Flag
Mecaliving
Resident
7y ago
"Walk to Willard Beach, Scratch Bakery, good local restaurants. Nice neighbors and close friends walking distance away. "
0
Flag
April C.
Resident
7y ago
"Great area to raise a family. Little to no crime, lots of family oriented activity, close to cultural center, close to nature, close to many modes of transportation."
0
Flag
chellebelle
Resident
7y ago
"Movie nights, winter fest, art in the park, holiday still in knightville, Willard square festival and even more."
1
Flag
Trulia User
Resident
7y ago
"We have a dog and there are many dog owners in this area. Our dog is well loved and known in our neighborhood and neighbors have often addressed our dog even though they may not know us By name.. ❤️"
0
Flag
Will E
Resident
7y ago
"Several schools and parks, multiple grocery shopping options. Close to family friendly beaches. Great place to create family memories."
0
Flag
Mroberts
Resident
7y ago
"Lots of places to walk your dog/s. Many yards are big enough to fence so your dog can enjoy your yard, if you like that sort of thing."
1
Flag
Bennermichelle
Resident
7y ago
"There are some community events in Knightsville which is another community nearby. There is also a farmers market nearby that is walkable or drivable and there are outdoor movies and fireworks and events at Big Light Park."
0
Flag
Ls5285
Resident
8y ago
"its filled with millenials and their children who play in the street and block traffic. every neighbor has a dog that barks constantly,"
5
Flag
Karen Z.
Resident
8y ago
"Gorgeous seaside neighborhood. It is close to everything yet great and safe place to walk, jog or bike. "
0
Flag
Bennermichelle
Resident
8y ago
"Walking and bike trails at the end of the street. Grocery stores, bakeries, and restaurants are three mins away. Yoga studios and gyms nearby. Quick access to airport and highway, but also beaches and parks. Safe, friendly, and cute neighborhood. "
1
Flag
Karen Z.
Resident
8y ago
"Beautiful waterfront community with lots going on, friendly people and proximity to wonderful shops, restaurants and retail of all kinds."
0
Flag

LGBTQ Local Legal Protections

Davidson Realty

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

5 Chestnut Street, Vinalhaven, ME 04863 is a 3 bedroom, 2 bathroom, 1,900 sqft single-family home built in 1790. This property is currently available for sale and was listed by Maine Listings on Jul 7, 2026. The MLS # for this home is MLS# 1670675.

5 Chestnut Street
Vinalhaven, ME 04863

$729,000

$729,000

Local Information