27 Chestnut St, Marblehead, MA 01945
OFF MARKET

$2,186,800

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 4,000 sqft

27 Chestnut St, Marblehead, MA 01945

Est. Refi. Payment $13,488/mo*
Refinance Your Home

Home Value

Trulia Estimate
$2.19M
Since last month
Decreased$70K (-3.1%)
Since last year
Increased$101K (+4.9%)
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 +70% in the last 10 years
MonthEstimated value
2026
September 2026$2.16M
August 2026$2.19M
July 2026$2.23M
June 2026$2.32M
May 2026$2.26M
April 2026$2.2M
March 2026$2.16M
February 2026$2.09M
January 2026$2.15M
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
53 Gregory St, Marblehead, MA
0.20
Single-Family Home
$760,000
09/25/25
4
3.5
2,781
23 Wyman Rd, Marblehead, MA
0.19
Single-Family Home
$1,940,000
04/15/26
4
2.5
2,564
10 Redstone Ln, Marblehead, MA
0.24
Single-Family Home
$2,000,000
06/01/26
6
3.5
3,586
27 Maverick St, Marblehead, MA
0.44
Single-Family Home
$1,250,000
07/24/26
4
3
3,220
57 Orchard St, Marblehead, MA
0.38
Single-Family Home
$2,335,000
06/01/26
4
3.5
3,390
3 Devereux Ter, Marblehead, MA
0.41
Single-Family Home
$1,350,000
06/18/26
4
2.5
2,718
21 Reed St, Marblehead, MA
0.49
Single-Family Home
$1,250,000
10/22/25
4
4
2,606
10 W Cottage St, Marblehead, MA
0.23
Single-Family Home
$1,331,625
06/02/26
4
2.5
2,202
27 Waldron St, Marblehead, MA
0.33
Single-Family Home
$1,615,000
09/11/26
3
2.5
2,136
7 Waldron Ct, Marblehead, MA
0.31
Single-Family Home
$1,387,500
10/24/25
4
2.5
2,376

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
27 Central St #1, Marblehead, MA 01945
0.04
$481,800
2
1
1,024
Off Market
29 Central St #1, Marblehead, MA 01945
0.04
$571,000
3
2
1,157
Off Market
22 Central St, Marblehead, MA 01945
0.06
$1,110,100
3
2
1,442
Off Market
14 Central St #B, Marblehead, MA 01945
0.08
$1,437,500
4
2.5
2,400
Recently Sold
35 Commercial St #A, Marblehead, MA 01945
0.09
$580,900
2
1.5
1,014
Off Market
9 Walnut St, Marblehead, MA 01945
0.10
$1,240,700
3
1.5
1,280
Off Market
49 Atlantic Ave, Marblehead, MA 01945
0.13
$1,210,700
6
3
2,534
Off Market
5 Harbor Vw, Marblehead, MA 01945
0.08
-
4
3.5
3,200
Off Market
2 Chestnut St, Marblehead, MA 01945
0.12
$857,800
4
1.5
1,450
Off Market
2 Central St, Marblehead, MA 01945
0.14
-
3
2.5
1,445
Off Market
1 Red Frank Ln, Marblehead, MA 01945
0.14
$815,000
2
1.5
1,240
Recently Sold
7 Cottage St, Marblehead, MA 01945
0.15
$910,000
3
2
1,000
Recently Sold

Local Information

  • Map ViewExplore the area around 27 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
4,000 sqft
$547/sqft
Garage

About this House

New Price! Home and Barn Meticulously renovated and maintained. Close to beach, park, schools, shops and restaurants. Five bedrooms including a large master suite with fire place and marble bath, gourmet kitchen, adjacent family room with Rockport granite fireplace, and a formal dining room. Separate in-law suite. Attached barn and workshop with heat & AC . Fenced in yard with lots of privacy. Gate to Seaside with tennis, fitness trails & playground.
27 Chestnut St, Marblehead, MA 01945 is a 4 bedroom, 5 bathroom, 4,000 sqft single-family home built in 1900. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,186,800, with a rent estimate of $6,726/month.

Home Details for 27 Chestnut St

Interior Features

Interior Details
BasementIn-law unitNumber of Rooms: 13Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, PantryWet Bar
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: ShingleLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1900Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Lot Information

Lot Area: 9200 sqft

Additional Information

Greenhouse

Price and Tax history

DateEventPrice
Mar 29, 2009
Source: Agent Provided
ListingRemoved
$1,125,000
Feb 28, 2009
Source: Agent Provided
PriceChange
$1,125,000
Price decreased by 6%
Jan 11, 2009
Source: Agent Provided
PriceChange
$1,199,000
Price decreased by 7%
Nov 10, 2008
Source: Agent Provided
Listed For Sale
$1,295,000

Market trends in Marblehead

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
46
4MoM

Around this home

What Locals Say about Marblehead

At least 107 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 80 % Say yards are well-kept

  • 78 % Say kids play outside

  • 78 % Say parking is easy

  • 78 % Say car is needed

  • 77 % Say there's holiday spirit

  • 72 % Say there are sidewalks

  • 70 % Say it's walkable to restaurants

  • 70 % Say neighbors are friendly

  • 69 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say it's walkable to grocery stores

  • 64 % Say there's wildlife

  • 64 % Say streets are well-lit

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "There are lots of community events and one of the best July 4th celebrations. Lots of church groups, Council on aging, etc"
    0
    Flag
  • 9vpwcs25jb
    "Everyone is friendly towards dogs. The dogs love every person who comes close to them. It’s a pleasure to see. "
    0
    Flag
  • 9vpwcs25jb
    "I work from home so I don’t commute. I have the best of both worlds and I’m totally appreciative. Out of the worst pandemic comes the best commute ever! How lucky we are!! "
    0
    Flag
  • Lytania Jason Knowles
    "I work ten minutes away so it’s great. 7:45-8:15 in town is a mess because all the schools are doing drop off. "
    0
    Flag
  • MARC MELTZER
    "Aside from the morning & afternoon traffic the commute is okay but to & from work can be very stressful "
    0
    Flag
  • Bdmn63
    "This is an absolutely fantastic community with parents who are actively involved with their families in the community great schools and great lifestyle with the beaches in waterfronts"
    3
    Flag
  • Tpnohelty
    "Great area to walk with dogs. Safe neighborhood and everyone keeps their dogs leashed when out and about."
    2
    Flag
  • Cassandra
    "Christmas walk every year Santa comes in a lobster boat and they have a parade and all the local stores have specials "
    1
    Flag
  • Cassandra
    "Art festival in the summer. Sidewalk sales for all the local shops. Crocker park has fireworks on holidays and beautiful view of the ocean. Outdoor dining on the water "
    4
    Flag
  • R E. M.
    "this is a one of a kind community. it is very historic, going back to the 1600's. it is very safe and family friendly. it is a bit hard to commute to, but totally worth it."
    5
    Flag
  • Chalvinleo
    "Marblehead is truly something else. I have lived here for the past 10 years and I am sad to leave. This town will always feel like home. "
    0
    Flag
  • Msherman48
    "It’s Marblehead, an almost 400 year old fishing village on Massachusetts Bay. We have a small town but urban “walking” downtown on a spectacularly beautiful natural harbor. This is the real thing! And, it’s only a short hop to Boston, America’s intellectual capital city. If it didn’t have a cold winter, the whole world would want to live here!"
    1
    Flag
  • Cynshor
    "Takes a little while to get out of Marblehead and through surrounding Salem and Swampscott. Worth every minute on the ride home when you hit the water views."
    3
    Flag
  • dbrownbos
    "My neighborhood is in a great location close to schools and old town section of town. You can walk to shopping and the harbor. Lots of attractions nearby. "
    2
    Flag
  • Frank K.
    "I’ve lived in this neighborhood for fourteen years and have nice neighbors. It is safe and people watch out for each other."
    2
    Flag
  • Rhonda
    "Stunning ocean and harbor views. Beach and water sports. Walking running and biking on the Neck. Eastern and Corinthian yacht clubs among others. "
    1
    Flag
  • richard n. a.
    "Fabulous and unique seaside community. History is everywhere. 16 miles from Boston. No place to build so housing is always in demand and home values do not get hit hard in economic downturns. Great town to protect your real estate investment. "
    1
    Flag
  • Sean
    "A corner lot in the desirable family neighborhood. Kids all abound. Ice Cream Trucks and good people."
    0
    Flag
  • Alicia H.
    "I live here and this town is fantastic - it's beautiful and friendly and full of things to do! "
    0
    Flag
  • Arian S.
    "Excellent location, wonderful views, quite. I love to live and work here."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Chestnut St

  • What is 27 Chestnut St estimated to be worth?
    Trulia's estimated value for 27 Chestnut St in Marblehead, MA is $2,186,800.
  • Is Marblehead a buyer's or seller's market?
    Marblehead is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Marblehead?
    Residents describe Marblehead, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Marblehead, MA.
  • What are the closest schools to 27 Chestnut St?
    The closest schools to 27 Chestnut St in Marblehead, MA are Marblehead High School (rated 8/10), Marblehead Veterans Middle School (rated 9/10), Village School (Elementary, rated 7/10).
  • Does 27 Chestnut St have laundry facilities?
    Yes, 27 Chestnut St in Marblehead, MA has in-unit laundry.
  • How big is the lot at 27 Chestnut St?
    The lot at 27 Chestnut St in Marblehead, MA is about 0.21 acres (9,200 sq ft).

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