Google street view image for 339 Main St, Winchester, MA 01890

Off market sep 1991 for $290K

$1,557,156

Est. refi paymentEst. refi $1,956/mo

•

2.5 ba

•

2,513

sq ft

339 Main St, Winchester, MA 01890

About this home

339 Main St is a 2,513 square foot house on a 9,148 square foot lot with 4 bedrooms and 2.5 bathrooms. - it last sold on September 17, 1991 for $290,000. Based on Redfin's Winchester data, we estimate the home's value is $1,557,156.

Single-familyProperty Type

1939Year Built

9,148 sq ftLot Size

$620Est. Price/Sq.Ft.

1 garage spacesParking

Source:Public Records

Redfin Estimate

$1,557,156

$1.3M since sold in September 1991$12K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.3% lower than the average sale price ($1.66M) of 6 comparable homes.

SOLD AUG 14, 2026
$1,500,000
A
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD APR 30, 2026
$1,560,000
B
4 beds2.5 baths2,578 sq ft
17 Cranston Rd, Winchester, MA 01890
SOLD NOV 20, 2025
$1,355,000
C
4 beds2.5 baths2,865 sq ft
4 Sargent Rd, Winchester, MA 01890
SOLD APR 22, 2026
$1,325,000
D
3 beds2.5 baths2,153 sq ft
6 Marchant Rd, Winchester, MA 01890
SOLD JAN 9, 2026
$1,930,000
E
4 beds2.5 baths3,658 sq ft
8 Felsdale Close, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
F
4 beds2.5 baths3,283 sq ft
12 Yale St, Winchester, MA 01890

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Sell

$1,478,983

Est. take-home

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Est. cash available

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Rent

$4,985/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.0%

0.9% MoM

Median sale price

$1.7M

$39K MoM

Avg. days on market

21d

3 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN TODAY, 11AM TO 12:30PM
$899,000
3 beds1 bath1,313 sq ft
39 Henry St, Winchester, MA 01890
$18,000,000
6 beds6.5 baths10,000 sq ft
15 Vinson Cir, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$3,299,000
7 beds7.5 baths7,226 sq ft
1 Plymouth Rd, Winchester, MA 01890
OPEN TODAY, 11AM TO 12:30PM
$1,299,000
6 beds2.5 baths3,910 sq ft
8 North Gtwy, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$1,529,000
4 beds3.5 baths2,709 sq ft
25 Arlington St, Winchester, MA 01890
EARLY ACCESS
$2,150,000
5 beds4 baths4,063 sq ft
21 Amberwood Dr, Winchester, MA 01890
OPEN TODAY, 11AM TO 12:30PM
$1,950,000
5 beds4 baths3,371 sq ft
26 Mayflower Rd, Winchester, MA 01890
OPEN SUN, 11AM TO 12:30PM
$1,195,000
3 beds1.5 baths2,239 sq ft
4 Stone Ave, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$1,850,000
4 beds2.5 baths3,092 sq ft
1 Overlook Way, Winchester, MA 01890
$700,000
2 beds2 baths1,240 sq ft
666 Main St #217, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 339 Main St

Year

Property tax

Land + Additions

Assessment*

2026

$15,888 (+4.0%)

$845,600 + $588,300

$1,433,900

2025

$15,272 (+6.1%)

$813,100 + $564,000

$1,377,100

2023

$14,400 (+1.8%)

$813,100 + $525,200

$1,338,300

2022

$14,140 (+8.4%)

$650,500 + $479,800

$1,130,300

2021

$13,040 (+3.5%)

$536,600 + $479,800

$1,016,400

2020

$12,593 (+12.5%)

$536,600 + $479,800

$1,016,400

2019

$11,197 (+0.7%)

$444,800 + $479,800

$924,600

2018

$11,118 (+7.0%)

$444,800 + $467,300

$912,100

2017

$10,394 (+14.1%)

$404,100 + $442,300

$846,400

2016

$9,107 (−1.9%)

$349,600 + $430,100

$779,700

2015

$9,283 (+7.4%)

$349,600 + $415,100

$764,700

2014

$8,647 (+0.6%)

$280,500 + $402,500

$683,000

2013

$8,594 (+1.8%)

$280,500 + $392,500

$673,000

2012

$8,446 (+3.7%)

$280,500 + $392,500

$673,000

2011

$8,143 (+3.9%)

$280,500 + $392,500

$673,000

2010

$7,836 (+2.1%)

$295,800 + $385,000

$680,800

2009

$7,673

$295,800 + $385,000

$680,800

Tax history for 339 Main St

Year

Property tax

Land + Additions

Assessment*

2026

$15,888 (+4.0%)

$845,600 + $588,300

$1,433,900

2025

$15,272 (+6.1%)

$813,100 + $564,000

$1,377,100

2023

$14,400 (+1.8%)

$813,100 + $525,200

$1,338,300

2022

$14,140 (+8.4%)

$650,500 + $479,800

$1,130,300

2021

$13,040 (+3.5%)

$536,600 + $479,800

$1,016,400

2020

$12,593 (+12.5%)

$536,600 + $479,800

$1,016,400

2019

$11,197 (+0.7%)

$444,800 + $479,800

$924,600

2018

$11,118 (+7.0%)

$444,800 + $467,300

$912,100

2017

$10,394 (+14.1%)

$404,100 + $442,300

$846,400

2016

$9,107 (−1.9%)

$349,600 + $430,100

$779,700

2015

$9,283 (+7.4%)

$349,600 + $415,100

$764,700

2014

$8,647 (+0.6%)

$280,500 + $402,500

$683,000

2013

$8,594 (+1.8%)

$280,500 + $392,500

$673,000

2012

$8,446 (+3.7%)

$280,500 + $392,500

$673,000

2011

$8,143 (+3.9%)

$280,500 + $392,500

$673,000

2010

$7,836 (+2.1%)

$295,800 + $385,000

$680,800

2009

$7,673

$295,800 + $385,000

$680,800

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

Property details

Interior

Basement Information
Basement Sq. Ft: 1,075

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Colonial
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Subdivision Name: WINCHESTER
Living Sq. Ft: 2,513
Gross Sq. Ft: 3,574
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 9,148
Municipality Name: WINCHESTER
Acres: 0.21
Zoning Code: RDB
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2026

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,513
Stories: 2.0
Lot Size: 9,148 square feet
Style: Single Family Residential
Year Built: 1939
Year Renovated: —
County: Middlesex County
APN: 2144338S

Home facts updated by county records on Sep 16, 2026

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.3mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.3mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.7mi

10/10

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 hot days expected this year, 15 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

Air Factor

We're working on getting current and accurate air risk information for this home.

Provided by First Street

Historical weather

Winchester, MA • 01890

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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.48M – $1.79M

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OPEN TODAY, 11AM TO 12:30PM

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OPEN TODAY, 11AM TO 12:30PM

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8 North Gtwy, Winchester, MA 01890

OPEN TODAY, 12PM TO 1:30PM

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4 beds3.5 baths2,709 sq ft

25 Arlington St, Winchester, MA 01890

EARLY ACCESSCOMPASS COMING SOON

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5 beds4 baths4,063 sq ft

21 Amberwood Dr, Winchester, MA 01890

OPEN TODAY, 11AM TO 12:30PM

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26 Mayflower Rd, Winchester, MA 01890

OPEN SUN, 11AM TO 12:30PM

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OPEN TODAY, 12PM TO 1:30PMVIDEO TOUR

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Home values near 339 Main St

Data from public records.

Address	Redfin Estimate
319 Main St, Winchester, MA 6 Beds \| 6 Baths \| 6484 Sq. Ft.	$3,084,998
361 Main St, Winchester, MA 6 Beds \| 4 Baths \| 4403 Sq. Ft.	$2,262,589

Address	Redfin Estimate
331 Main St, Winchester, MA 5 Beds \| 3.5 Baths \| 3601 Sq. Ft.	$1,998,463
371 Main St, Winchester, MA 6 Beds \| 4.5 Baths \| 6200 Sq. Ft.	$2,759,320

Address	Redfin Estimate
345 Main St, Winchester, MA 6 Beds \| 3.5 Baths \| 3054 Sq. Ft.	$1,758,235
316 Main St, Winchester, MA 3 Beds \| 2.5 Baths \| 2384 Sq. Ft.	$1,434,896

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