OFF MARKET

Off Market May 2025 for $460K

$408,903

•

1,090

sq ft

21 Chestnut St #305, Portland, ME 04101

About this home

Sophisticated Downtown Loft at 21 Chestnut Street - Urban Living at Its Finest Discover the perfect blend of modern elegance and historic character in this stunning loft-style condo, ideally located in the vibrant heart of downtown Portland, Maine. Situated at 21 Chestnut Street, this refined residence offers a rare opportunity to live just steps from the city's acclaimed dining scene, boutique shopping, cultural attractions, and the beloved farmers market. Inside, you'll find a light-filled, open-concept layout with soaring ceilings, polished concrete floors, and oversized windows that showcase picturesque views of Munjoy Hill and Back Cove. The expansive living area is ideal for hosting intimate dinner parties or enjoying quiet evenings at home, all framed by a sleek, urban aesthetic that defines modern loft living. After a day exploring the city, retreat to the spacious and serene bedroom, offering comfort and privacy in equal measure. Or, head to the shared rooftop deck, where sweeping views of Portland's skyline and Casco Bay provide the perfect backdrop for morning coffee or sunset cocktails. Additional amenities include reserved parking, dedicated storage, internet/cable, and secure building access—everything you need for a seamless, low-maintenance lifestyle. Whether you're searching for a stylish primary residence or a sophisticated pied-à-terre, this downtown loft embodies the very best of Portland living. Don't miss your chance to make it yours.

CondoProperty Type

2007Year Built

$375Est. Price/Sq.Ft.

1 spaceParking

Listed by David Marsden • Marsden Real Estate

Bought with Shea McGonigal • Beacon Realty

Redfin checked: a few seconds ago

•Source:MREIS #1619680

Redfin Estimate

$408,903

$51K since sold in May 2025$28K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.5% lower than the average sale price ($549K) of 6 comparable homes.

SOLD AUG 24, 2026
$735,000
A
1 bed1 bath1,166 sq ft
62 India St #206, Portland, ME 04101
SOLD DEC 9, 2025
$415,000
B
1 bed1 bath1,024 sq ft
21 Chestnut St #203, Portland, ME 04101
SOLD AUG 28, 2026
$475,000
C
1 bed1 bath1,100 sq ft
269 Commercial St Unit 5B, Portland, ME 04101
SOLD AUG 18, 2026
$549,000
D
1 bed1 bath1,006 sq ft
387 Commercial St #334, Portland, ME 04101
SOLD APR 2, 2026
$685,000
E
1 bed1 bath864 sq ft
62 India St #410, Portland, ME 04101
SOLD OCT 14, 2025
$435,000
F
1 bed1 bath895 sq ft
21 Chestnut St #304, Portland, ME 04101

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Earn from this home

Sell

$23,347

Est. take-home

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Rent

$2,877/mo

Redfin rental estimate

List your home for rent

Market trends in 04101, ME

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

97.9%

0.5% MoM

Median sale price

$725K

$26K MoM

Avg. days on market

37d

9 days MoM

Recently sold homes

1 MoM

New listings for sale

$595,000
2 beds2 baths1,730 sq ft
45 Eastern Promenade Unit 8F & 8G, Portland, ME 04101
$1,172,000
5 beds3 baths2,557 sq ft
12 North St, Portland, ME 04101
$785,000
2 beds2 baths1,341 sq ft
61 Montreal St #3, Portland, ME 04101
$789,000
7 beds3 baths3,030 sq ft
124 Sherman St, Portland, ME 04101
$520,000
2 beds1 bath700 sq ft
99 Silver St Unit 3-5, Portland, ME 04101
$549,900
1 bed1.5 baths877 sq ft
75 Chestnut St #609, Portland, ME 04101
3D WALKTHROUGH
$699,900
2 beds2 baths1,030 sq ft
75 Chestnut St #607, Portland, ME 04101
OPEN SAT, 11AM TO 1PM
$875,000
5 beds3 baths2,535 sq ft
106 Sherman St, Portland, ME 04101
$439,000
2 beds1 bath690 sq ft
129 York St #2, Portland, ME 04101
$599,000
3 beds1 bath1,396 sq ft
43 Cumberland Ave #2, Portland, ME 04101
See all

Provided by Redfin

Sale history for 21 Chestnut St #305

Date

Event

Price

MREIS #1619680

May 30, 2025

Sold

$460,000

$422/sq ft

Apr 21, 2025

Listed

$440,000

$404/sq ft

MREIS #1030154

Dec 6, 2011

Sold

$252,000

$231/sq ft

Sep 20, 2011

Listed

$262,000

$240/sq ft

+19

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

—

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Condo/Co-op

County

Cumberland County

APN

21Chestnut Street305Portland27C10

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Dec 13, 2023.

DEOZ

Downtown Business District

To maintain and enhance the role of the downtown as the business and commercial center of the region, and to enhance and promote the orderly expansion of retail and service businesses downtown, satisfying the related needs of the city’s resident, working, and visitor populations. The B-3 zone encourages increased housing opportunities downtown, including three-family, four-family, townhouse, and multi-family structures to accommodate Portland’s diverse residential population, and supports an active, walkable pedestrian environment through the encouragement of intensive mixed-use activities, enhancement and maintenance of public and private open space, and the enlivenment and increased attractiveness of the street environment. Standards of the B-3 zone require excellence in urban design, to preserve and capitalize on the unique character and historic fabric of downtown Portland by encouraging reuse of significant existing structures and providing opportunities for an enhanced presence and integration of arts and cultural activities. The zone reinforces the role of downtown as a meeting place for community residents and visitors alike from all walks of life and all socio- economic groups by prioritizing access via multiple modes of transportation and enhancing and protecting the pedestrian environment.

Zone overlays

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: Reserved Parking, 1 - 4 Spaces, Paved, Common, Off Street

Interior

Virtual Tour

Bathroom Information
# of Baths (Full): 1

Room 1 Information
Type: Dining Room
Level: First
Features: Dining Area

Room 2 Information
Type: Office
Level: First
Features: Closet

Room 3 Information
Type: Kitchen
Level: First
Features: Eat-In Kitchen, Kitchen Island

Room 4 Information
Type: Living Room
Level: First
Features: Sunken/Raised

Room 5 Information
Type: Primary Bedroom
Level: First
Features: Built-Ins, Walk-In Closet(s)

Basement Information
Basement Entry: Interior, Full

Interior Features
# of Rooms: 5
Interior Features: Walk-in Closets, Elevator Passenger, 1st Floor Bedroom, Bathtub, One-Floor Living, Other, Shower, Storage
Furnished: Negotiable
Tankless Water Heater, Washer, Refrigerator, Microwave, Gas Range, Dryer, Disposal, Dishwasher
Accessibility Features: Accessible Approach With Ramp
Window Features: Double-Pane Windows
Flooring: Wood, Concrete
Other Equipment: Internet Access Available, Cable

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

Exterior

Building Information
# of Buildings: 1
Construction Materials: Metal Clad, Composition, Steel Frame
Foundation Details: Concrete Perimeter
Roof: Membrane, Rolled/Hot Mop
Total Building Area (Sq. Ft.): 1,090
Building Area Source: Public Records

Exterior Features
Patio & Porch Features: Deck

Property Information
Property Sub Type: Condominium
Security Features: Sprinkler, Fire System
Year Built: 2007
Above-Grade Finished Area (Sq. Ft.): 1,090

Lot Information
Lot Size Source: Public Records
Lot Features: Well Landscaped, Open, Level, Sidewalks, Intown, Near Golf Course, Near Public Beach, Near Shopping, Near Turnpike/Interstate, Near Town, Neighborhood, Near Public Transit, Near Railroad
Road Surface Type: Paved
Zoning: B3

Subdivision Information
Subdivision Name: Downtown/Old Port

Financial

Tax Information
Annual Tax Amount: $5,722
Tax Year: 2025

Utilities

Utility Information
Has Heating
Heating: Hot Water, Baseboard
Has Cooling
Cooling: Wall/Window Unit(s)
Electric: Circuit Breakers
Sewer: Public Sewer
Utilities: Utilities On
Utilities On: Yes
Water Source: Public
Water Heater: Off Heating System, On Demand

Location

Multi-Unit Information
# of Units in Community: 37

HOA Information
Has Association
Association Fee: $555
Association Fee Frequency: Monthly
Pets Allowed: Other Restrictions

Location Information
Unparsed Address: 21 Chestnut Street 305, Portland, ME 04101
Directions: Downtown Portland - next to Merrill auditorium & City Hall - Chestnut street is one way from Cumberland Ave. Parking space #21 behind building

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Condo/Co-op
Year Built: —
Year Renovated: —
County: Cumberland County
APN: 21Chestnut Street305Portland27C10

Home facts updated by county records on Dec 12, 2023

About this building

1 for sale

21 Chestnut St, Portland, ME 04101

See photos & sale trends

Photo via 21 Chestnut St #502

Units for sale


606	$425,000	1 bed	1 bath	935 sq ft

Around this home

Schools

Howard C Reiche Community School

Public PreK-5 • Assigned • 0.8mi

3/10

Deering High School

Public 9-12 • Assigned • 2.1mi

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, 20 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

$389,000 – $471,000

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Nearby similar homes

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75 Chestnut St #609, Portland, ME 04101

New listings for sale in 04101

$595,000

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45 Eastern Promenade Unit 8F & 8G, Portland, ME 04101

$1,172,000

5 beds3 baths2,557 sq ft

12 North St, Portland, ME 04101

$785,000

2 beds2 baths1,341 sq ft

61 Montreal St #3, Portland, ME 04101

$789,000

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124 Sherman St, Portland, ME 04101

$520,000

2 beds1 bath700 sq ft

99 Silver St Unit 3-5, Portland, ME 04101

$549,900

1 bed1.5 baths877 sq ft

75 Chestnut St #609, Portland, ME 04101

3D WALKTHROUGH

$699,900

2 beds2 baths1,030 sq ft

75 Chestnut St #607, Portland, ME 04101

OPEN SAT, 11AM TO 1PM

$875,000

5 beds3 baths2,535 sq ft

106 Sherman St, Portland, ME 04101

$439,000

2 beds1 bath690 sq ft

129 York St #2, Portland, ME 04101

Home values near 21 Chestnut St #305

Data from public records.

Address	Redfin Estimate
21 Chestnut Street Unit 4S, Portland, ME 2 Beds \| 1 Baths \| 935 Sq. Ft.	$467,207
21 Chestnut Street Unit 6NW, Portland, ME 1 Beds \| 1 Baths \| 1024 Sq. Ft.	$527,217

Address	Redfin Estimate
21 Chestnut Street Unit 7W, Portland, ME 1 Beds \| 1.5 Baths \| 1065 Sq. Ft.	$501,913
21 Chestnut Street Unit 5SE, Portland, ME 1 Beds \| 1 Baths \| 895 Sq. Ft.	$477,804

Address	Redfin Estimate
21 Chestnut Street Unit 3SE, Portland, ME 2 Beds \| 1 Baths \| 895 Sq. Ft.	$453,960
21 Chestnut Street Unit 7E, Portland, ME 2 Beds \| 1.5 Baths \| 1120 Sq. Ft.	$520,536

Property information provided by MREIS when last listed in 2025. This data may not match . Learn more.

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