Google street view image for 20 Dennett Rd, Winchester, MA 01890

Off market dec 1986 for $425K

$1,843,470

Est. refi paymentEst. refi $2,809/mo

•

2.5 ba

•

3,442

sq ft

20 Dennett Rd, Winchester, MA 01890

About this home

20 Dennett Rd is a 3,442 square foot house on a 0.35 acre lot with 4 bedrooms and 2.5 bathrooms. - it last sold on December 29, 1986 for $425,000. Based on Redfin's Winchester data, we estimate the home's value is $1,843,470.

Single-familyProperty Type

1968Year Built

0.35 acresLot Size

$536Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,843,470

$1.4M since sold in December 1986$24K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.2% lower than the average sale price ($1.96M) of 5 comparable homes.

BOUGHT WITH REDFIN JUL 13, 2026
$2,150,000
A
5 beds3 baths3,136 sq ft
22 Hollywood Rd, Winchester, MA 01890
SOLD JUN 1, 2026
$1,607,000
B
4 beds2.5 baths3,298 sq ft
6 Oakland Cir, Winchester, MA 01890
SOLD SEP 2, 2026
$2,250,000
C
4 beds3 baths4,210 sq ft
6 Davey Ln, Winchester, MA 01890
SOLD JUL 30, 2026
$2,255,000
D
4 beds3.5 baths3,494 sq ft
2 York Rd, Winchester, MA 01890
SOLD APR 30, 2026
$1,560,000
E
4 beds2.5 baths2,578 sq ft
17 Cranston Rd, Winchester, MA 01890

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Earn from this home

Sell

$1,751,108

Est. take-home

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Est. cash available

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Rent

$5,490/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%

0.0% MoM

Median sale price

$1.8M

$87K MoM

Avg. days on market

22d

1 days MoM

Recently sold homes

14 MoM

New listings for sale

$1,450,000
8 beds5 baths6,200 sq ft
67-69 Hemingway St, Winchester, MA 01890
$2,999,000
5 beds4.5 baths4,900 sq ft
5 Forest Cir, Winchester, MA 01890
$1,049,000
4 beds2 baths2,226 sq ft
16-18 Russell Rd, Winchester, MA 01890
$2,650,000
4 beds4.5 baths5,233 sq ft
18 Middlesex St, Winchester, MA 01890
$3,799,000
8 beds5 baths7,081 sq ft
15 Foxcroft Rd, Winchester, MA 01890
OPEN SUN, 12PM TO 1PM
$1,299,000
6 beds2 baths2,946 sq ft
419-421 Washington St, Winchester, MA 01890
$2,950,000
6 beds4 baths4,752 sq ft
18 Surrey Rd, Winchester, MA 01890
EARLY ACCESS
$4,199,000
6 beds6 baths7,175 sq ft
7 Aquinas Path, Winchester, MA 01890
$890,000
2 beds1 bath1,489 sq ft
80 Nelson St, Winchester, MA 01890
3D & VIDEO TOUR
$1,985,000
4 beds3.5 baths4,241 sq ft
30 Surrey Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 20 Dennett Rd

Year

Property tax

Land + Additions

Assessment*

2026

$17,789 (+3.0%)

$1,027,900 + $577,600

$1,605,500

2025

$17,275 (+9.6%)

$1,027,900 + $529,800

$1,557,700

2023

$15,765 (+1.9%)

$954,500 + $498,600

$1,453,100

2022

$15,477 (+8.8%)

$770,900 + $466,300

$1,237,200

2021

$14,225 (+7.1%)

$642,400 + $466,300

$1,108,700

2020

$13,282 (+9.8%)

$605,700 + $466,300

$1,072,000

2019

$12,093 (+7.9%)

$532,300 + $466,300

$998,600

2018

$11,206 (+3.6%)

$502,000 + $417,300

$919,300

2017

$10,815 (+7.1%)

$472,600 + $408,100

$880,700

2016

$10,101 (+8.2%)

$472,600 + $392,200

$864,800

2015

$9,336 (+6.5%)

$429,500 + $339,500

$769,000

2014

$8,765 (−0.9%)

$357,900 + $334,400

$692,300

2013

$8,841 (+1.8%)

$357,900 + $334,400

$692,300

2012

$8,688 (+3.7%)

$357,900 + $334,400

$692,300

2011

$8,377 (+1.3%)

$357,900 + $334,400

$692,300

2010

$8,269 (+2.1%)

$383,600 + $334,800

$718,400

2009

$8,096

$383,600 + $334,800

$718,400

Tax history for 20 Dennett Rd

Year

Property tax

Land + Additions

Assessment*

2026

$17,789 (+3.0%)

$1,027,900 + $577,600

$1,605,500

2025

$17,275 (+9.6%)

$1,027,900 + $529,800

$1,557,700

2023

$15,765 (+1.9%)

$954,500 + $498,600

$1,453,100

2022

$15,477 (+8.8%)

$770,900 + $466,300

$1,237,200

2021

$14,225 (+7.1%)

$642,400 + $466,300

$1,108,700

2020

$13,282 (+9.8%)

$605,700 + $466,300

$1,072,000

2019

$12,093 (+7.9%)

$532,300 + $466,300

$998,600

2018

$11,206 (+3.6%)

$502,000 + $417,300

$919,300

2017

$10,815 (+7.1%)

$472,600 + $408,100

$880,700

2016

$10,101 (+8.2%)

$472,600 + $392,200

$864,800

2015

$9,336 (+6.5%)

$429,500 + $339,500

$769,000

2014

$8,765 (−0.9%)

$357,900 + $334,400

$692,300

2013

$8,841 (+1.8%)

$357,900 + $334,400

$692,300

2012

$8,688 (+3.7%)

$357,900 + $334,400

$692,300

2011

$8,377 (+1.3%)

$357,900 + $334,400

$692,300

2010

$8,269 (+2.1%)

$383,600 + $334,800

$718,400

2009

$8,096

$383,600 + $334,800

$718,400

*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: 1,673

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: 6

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Contemporary
Construction Type: Frame
Roof Shape Type: Gable

Property Information
Subdivision Name: SOUTH BORDER PARK
Living Sq. Ft: 3,442
Gross Sq. Ft: 5,872
# 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: 15,246
Municipality Name: WINCHESTER
Acres: 0.35
Zoning Code: RDC
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2026

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 3,442
Stories: 2.0
Lot Size: 0.35 acres
Style: Single Family Residential
Year Built: 1968
Year Renovated: —
County: Middlesex County
APN: 3469138S

Home facts updated by county records on Sep 16, 2026

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.9mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.9mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.2mi

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

3/10 Fire Factor

0.62% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 14 days in 30 years

6/10 Wind Factor

51% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

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

$1.75M – $2.12M

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3D WALKTHROUGH

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New listings for sale in 01890

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$3,799,000

8 beds5 baths7,081 sq ft

15 Foxcroft Rd, Winchester, MA 01890

OPEN SUN, 12PM TO 1PM

$1,299,000

6 beds2 baths2,946 sq ft

419-421 Washington St, Winchester, MA 01890

$2,950,000

6 beds4 baths4,752 sq ft

18 Surrey Rd, Winchester, MA 01890

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$4,199,000

6 beds6 baths7,175 sq ft

7 Aquinas Path, Winchester, MA 01890

$890,000

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Home values near 20 Dennett Rd

Data from public records.

Address	Redfin Estimate
3 Dennett Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 2128 Sq. Ft.	$1,631,964
17 Dennett Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2283 Sq. Ft.	$1,686,505

Address	Redfin Estimate
5 Dennett Rd, Winchester, MA 4 Beds \| 4 Baths \| 3555 Sq. Ft.	$1,847,051
19 Dennett Rd, Winchester, MA 4 Beds \| 3 Baths \| 2706 Sq. Ft.	$1,742,201

Address	Redfin Estimate
7 Dennett Rd, Winchester, MA 4 Beds \| 3.5 Baths \| 3500 Sq. Ft.	$2,081,212
21 Dennett Rd, Winchester, MA 3 Beds \| 3.5 Baths \| 3429 Sq. Ft.	$1,791,719

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