OFF MARKET

Off Market Dec 2019 for $458K

$775,554

•

2,292

sq ft

37 Chestnut St, Portland, ME 04101

About this home

Brick 2-family in the very center of Portland's peninsula. There are few locations anywhere in the country that are more walk-able (96 Score) and bike-able (81 Score). All you could ever want or need from recreation and restaurants to business' and boutiques is within a few short blocks. Built in 1849 and comprehensible updates since, this quality 2-unit is ideal for the urban owner occupant. Why settle for a condo when you can own it all and have a tenant help pay the mortgage? The units are beautiful with pumpkin pine floors, exposed brick and lots of unique and period charm / architectural interest. Fully separate utilities, efficient natural gas heat, brand new hot water heaters and many updates. .. Off street parking for 1+ and a small yard for enjoyment or potentially more parking. Tenant occupied. 48 hours notice is required.

Multi-familyProperty Type

1849Year Built

2,178 sq ftLot Size

$338Est. Price/Sq.Ft.

1 spaceParking

Listed by Thomas {Tom} Landry • Benchmark Real Estate

Bought with Marilyn Miller • RE/MAX Shoreline

Redfin checked: a few seconds ago

•Source:MREIS #1424052

Redfin Estimate

$775,554

$318K since sold in December 2019$7,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9% lower than the average sale price ($852K) of 6 comparable homes.

SOLD MAY 15, 2026
$760,000
A
5 beds2 baths1,970 sq ft
52 Smith St, Portland, ME 04101
SOLD APR 13, 2026
$650,000
B
3 beds2 baths1,766 sq ft
11 Romasco Ln, Portland, ME 04101
SOLD MAY 26, 2026
$995,000
C
4 beds3.5 baths1,977 sq ft
46 Avon St, Portland, ME 04101
SOLD APR 10, 2026
$760,000
D
2 beds2 baths1,935 sq ft
87 Newbury St, Portland, ME 04101
SOLD MAR 9, 2026
$957,000
E
4 beds2.5 baths2,473 sq ft
536 Cumberland Ave, Portland, ME 04101
SOLD JAN 26, 2026
$990,000
F
4 beds3 baths2,576 sq ft
379 Cumberland Ave #3, Portland, ME 04101

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Earn from this home

Sell

$411,952

Est. take-home

List your home with Redfin and save $7,756

Market trends in 04101, ME

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.5%

0.5% MoM

Median sale price

$698K

$10K MoM

Avg. days on market

28d

0 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 4 HRS AGO
$470,000
3 beds1 bath1,140 sq ft
290 Baxter Blvd Unit E2, Portland, ME 04101
OPEN SUN, 10AM TO 11:30AM
$599,000
3 beds1 bath1,396 sq ft
43 Cumberland Ave #2, Portland, ME 04101
NEW 27 HRS AGO
$1,325,000
3 beds2.5 baths2,076 sq ft
15 Middle St #308, Portland, ME 04101
$989,000
5 beds3 baths3,228 sq ft
11 South St, Portland, ME 04101
$400,000
3 beds1 bath1,519 sq ft
187 Congress St, Portland, ME 04101
$339,000
1 bed1 bath938 sq ft
99 Silver St Unit 2-11, Portland, ME 04101
$425,000
1 bed1 bath935 sq ft
21 Chestnut St #606, Portland, ME 04101
$645,000
1 bed1 bath851 sq ft
716 Chandler's Wharf #716, Portland, ME 04101
$199,000
1 bed1 bath448 sq ft
58 Portland St #3, Portland, ME 04101
See all

Provided by Redfin

Sale history for 37 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2024

$8,191 (+4.2%)

$125,500 + $420,200

$545,700

2023

$7,864 (+5.9%)

$125,500 + $420,200

$545,700

2022

$7,427 (+4.8%)

$125,500 + $420,200

$545,700

2021

$7,089 (+35.0%)

$125,500 + $420,200

$545,700

2020

$5,252

$59,800 + $165,500

$225,300

2019

$5,252 (+3.7%)

$59,800 + $165,500

$225,300

2018

$5,065 (+3.8%)

$59,800 + $165,500

$225,300

2017

$4,878 (+2.6%)

$59,800 + $165,500

$225,300

2016

$4,756 (+2.3%)

$59,800 + $165,500

$225,300

2015

$4,648 (+3.2%)

$59,800 + $165,500

$225,300

2014

$4,506

$59,800 + $165,500

$225,300

Tax history for 37 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2024

$8,191 (+4.2%)

$125,500 + $420,200

$545,700

2023

$7,864 (+5.9%)

$125,500 + $420,200

$545,700

2022

$7,427 (+4.8%)

$125,500 + $420,200

$545,700

2021

$7,089 (+35.0%)

$125,500 + $420,200

$545,700

2020

$5,252

$59,800 + $165,500

$225,300

2019

$5,252 (+3.7%)

$59,800 + $165,500

$225,300

2018

$5,065 (+3.8%)

$59,800 + $165,500

$225,300

2017

$4,878 (+2.6%)

$59,800 + $165,500

$225,300

2016

$4,756 (+2.3%)

$59,800 + $165,500

$225,300

2015

$4,648 (+3.2%)

$59,800 + $165,500

$225,300

2014

$4,506

$59,800 + $165,500

$225,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2,178 Sq. Ft.

Year renovated

—

Sq. Ft.

2,369

Year built

1849

Style

Multi-Family (2-4 Unit)

County

Cumberland County

APN

111851

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

R-7

Community Business District

To provide appropriate locations for the development and operation of community centers offering a mixture of commercial uses, housing, and services serving the adjoining neighborhoods and the larger community. The variety, sites, and intensity of the permitted commercial uses in the B-2 zone are intended to be greater than those permitted in the B-1/B-1b zones. The zone provides a broad range of goods and services with a mixture of large and small buildings, such as grocery stores, shops and services located in major shopping centers and along arterial streets. Such establishments should be readily accessible by automobile, by pedestrians and by bicycle. Development in the B-2 zone should relate to the surrounding neighborhoods by design, orientation, and circulation patterns. The zone should provide locations for moderate to high-density housing in urban neighborhoods along arterials.

Zone overlays

Compact Urban Residential Overlay

Permitted uses

Include but are not limited to:

Day care facility
General retail
Restaurant
Housing-Multiple units
Housing-Senior
Industrial
Hotel / motel
Mixed use
Office
Public service

Property details

Parking

Parking Information
Parking Features: 1 - 4 Spaces, Paved, On Site, Off Street

Interior

Bathroom Information
# of Baths (Full): 2

Basement Information
Basement Entry: Interior, Full, Unfinished

Interior Features
Interior Features: 1st Floor Bedroom, One-Floor Living, Other, Pantry, Storage
Flooring: Wood, Vinyl, Tile, Carpet

Laundry Information
Laundry Features: 1st Floor Laundry, Main Level, Washer Hookup

Multi-Unit Information
# of Units Total: 2
# of 2 Bedroom Units: 2

Unit 1 Information
# of Bedrooms: 2
Dedicated Gas Meter: Yes
Dedicated Water Heater: Yes
Electric: No
Refrigerator: Yes
Sewer: Yes
Water: Yes

Unit 2 Information
# of Bedrooms: 2
Dedicated Gas Meter: No
Dedicated Water Heater: Yes
Electric: No
Refrigerator: Yes
Sewer: Yes
Water: Yes

Exterior

Building Information
Construction Materials: Brick, Masonry
Foundation Details: Stone, Brick/Mortar
Roof: Pitched, Shingle
Total Building Area (Sq. Ft.): 2,292

Exterior Features
Fencing: Fenced

Property Information
Year Built: 1849
Above-Grade Finished Area (Sq. Ft.): 2,292

Lot Information
Lot Size (Sq. Ft.): $2,178
Lot Size (Acres): 0.05
Lot Size Source: Public Records
Lot Features: Open, Level, Sidewalks, Intown, Near Golf Course, Near Public Beach, Near Shopping, Near Turnpike/Interstate, Near Public Transit
Road Surface Type: Paved
Zoning: B2

Subdivision Information
Subdivision Name: West Bayside

Financial

Tax Information
Annual Tax Amount: $5,065
Tax Year: 2018

Utilities

Utility Information
Has Heating
Heating: Zoned, Hot Water, Forced Air, Baseboard
Electric: Circuit Breakers
Sewer: Public Sewer
Utilities On: No
Water Source: Public
Water Heater: Gas, Tank

Location

Location Information
Unparsed Address: 37 Chestnut Street, Portland, ME 04101
Directions: Cumberland Ave to Chestnut St (close to City Hall and one block off Congress St)

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 2,369
Stories: 2.0
Lot Size: 2,178 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1849
Year Renovated: —
County: Cumberland County
APN: 111851

Home facts updated by county records on Jul 27, 2026

Around this home

Schools

Howard C Reiche Community School

Public PreK-5 • Assigned • 0.8mi

3/10

Deering High School

Public 9-12 • Assigned • 2.0mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 87° expected this year, 19 days in 30 years

6/10 Wind Factor

67% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Portland, ME • 04101

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.5 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.5 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$737,000 – $892,000

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New listings for sale in 04101

NEW 4 HRS AGO

$470,000

3 beds1 bath1,140 sq ft

290 Baxter Blvd Unit E2, Portland, ME 04101

OPEN SUN, 10AM TO 11:30AM

$599,000

3 beds1 bath1,396 sq ft

43 Cumberland Ave #2, Portland, ME 04101

NEW 27 HRS AGO

$1,325,000

3 beds2.5 baths2,076 sq ft

15 Middle St #308, Portland, ME 04101

$989,000

5 beds3 baths3,228 sq ft

11 South St, Portland, ME 04101

$400,000

3 beds1 bath1,519 sq ft

187 Congress St, Portland, ME 04101

$339,000

1 bed1 bath938 sq ft

99 Silver St Unit 2-11, Portland, ME 04101

$425,000

1 bed1 bath935 sq ft

21 Chestnut St #606, Portland, ME 04101

$645,000

1 bed1 bath851 sq ft

716 Chandler's Wharf #716, Portland, ME 04101

$199,000

1 bed1 bath448 sq ft

58 Portland St #3, Portland, ME 04101

Home values near 37 Chestnut St

Data from public records.

Address	Redfin Estimate
21 Chestnut Street #3N, Portland, ME 1 Beds \| 1 Baths \| 1090 Sq. Ft.	$463,673
41 Chestnut Street, Portland, ME 48 Beds \| 16 Baths \| 15620 Sq. Ft.	—

Address	Redfin Estimate
21 Chestnut Street #8S, Portland, ME 1 Beds \| 1.5 Baths \| 1370 Sq. Ft.	$695,645
21 Chestnut Street #2S, Portland, ME 2 Beds \| 1 Baths \| 935 Sq. Ft.	$440,899

Address	Redfin Estimate
49 Chestnut Street, Portland, ME 4 Beds \| 4 Baths \| 2724 Sq. Ft.	—
21 Chestnut Street #4W, Portland, ME 1 Beds \| 1 Baths \| 1090 Sq. Ft.	$488,639

Property information provided by MREIS when last listed in 2019. This data may not match . Learn more.

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