OFF MARKET

Off Market Jun 2011 for $715K

$1,739,281

Est. refi paymentEst. refi $4,473/mo

•

2,397

sq ft

23 Dennett Rd, Winchester, MA 01890

About this home

Picturesque Jerome Bailey Foster hip roof center entrance colonial located on a spacious corner lot. Great flow from mudroom with half bath & laundry leads to large kitchen and fireplace family room combination. Two car garage attached by breezeway. Beautiful shrubs, tall pines and flowering trees, private brick patio. 8ft high ceilings, hardwood floors. Four corner bedrooms, master bedroom includes fireplace, dressing area and bath. This house needs some updating.

Single-familyProperty Type

1963Year Built

0.35 acresLot Size

$726Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Anne Spry • Waterfield Sotheby's International Realty

Listed by • Waterfield Sotheby's International Realty

Bought with Peggy Otis • Coldwell Banker Residential Brokerage - Winchester

Redfin checked: 2 minutes ago

•Source:MLS PIN #71232244

Redfin Estimate

$1,739,281

$1.0M since sold in June 2011$17K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.6% higher than the average sale price ($1.60M) of 6 comparable homes.

SOLD APR 30, 2026
$1,560,000
A
4 beds2.5 baths2,578 sq ft
17 Cranston Rd, Winchester, MA 01890
BOUGHT WITH REDFIN JUL 13, 2026
$2,150,000
B
5 beds3 baths3,136 sq ft
22 Hollywood Rd, Winchester, MA 01890
SOLD OCT 9, 2025
$1,500,000
C
3 beds2.5 baths2,283 sq ft
17 Dennett 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 MAR 25, 2026
$1,470,000
E
3 beds2.5 baths2,370 sq ft
2 Canterbury Rd, Winchester, MA 01890
SOLD JUN 1, 2026
$1,607,000
F
4 beds2.5 baths3,298 sq ft
6 Oakland Cir, Winchester, MA 01890

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Sell

$1,288,082

Est. take-home

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Est. cash available

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Rent

$4,788/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.0% MoM

Median sale price

$1.4M

$57K MoM

Avg. days on market

20d

0 days MoM

Recently sold homes

14 MoM

New listings for sale

OPEN TODAY, 5PM TO 6:30PM
$1,699,000
5 beds3.5 baths3,180 sq ft
30 Farrow St, Winchester, MA 01890
$1,098,000
3 beds1.5 baths1,657 sq ft
17 Russell Rd, Winchester, MA 01890
$1,999,000
4 beds2.5 baths3,757 sq ft
85 High St, Winchester, MA 01890
EARLY ACCESS
Unknown
3 beds3 baths5,127 sq ft
187 High St, Winchester, MA 01890
$949,999
4 beds2 baths2,326 sq ft
96 Loring Ave, Winchester, MA 01890
$3,199,000
5 beds4.5 baths5,406 sq ft
10 Rangeley Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 23 Dennett Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,731 (+11.0%)

$1,024,000 + $484,700

$1,508,700

2023

$15,079 (+2.0%)

$950,800 + $447,400

$1,398,200

2022

$14,782 (+9.4%)

$768,000 + $413,600

$1,181,600

2021

$13,518 (+7.3%)

$640,000 + $413,600

$1,053,600

2020

$12,601 (+7.1%)

$603,400 + $413,600

$1,017,000

2019

$11,762 (+3.9%)

$530,300 + $441,000

$971,300

2018

$11,321 (+5.4%)

$500,100 + $428,600

$928,700

2017

$10,739 (+6.7%)

$470,800 + $403,700

$874,500

2016

$10,068 (+3.1%)

$470,800 + $391,200

$862,000

2015

$9,763 (+7.1%)

$427,900 + $376,300

$804,200

2014

$9,115 (+0.6%)

$356,600 + $363,400

$720,000

2013

$9,065 (+2.6%)

$356,600 + $353,300

$709,900

2012

$8,831 (+3.7%)

$356,600 + $347,100

$703,700

2011

$8,515 (+0.2%)

$356,600 + $347,100

$703,700

2010

$8,500 (+2.1%)

$382,200 + $356,300

$738,500

2009

$8,323

$382,200 + $356,300

$738,500

Tax history for 23 Dennett Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,731 (+11.0%)

$1,024,000 + $484,700

$1,508,700

2023

$15,079 (+2.0%)

$950,800 + $447,400

$1,398,200

2022

$14,782 (+9.4%)

$768,000 + $413,600

$1,181,600

2021

$13,518 (+7.3%)

$640,000 + $413,600

$1,053,600

2020

$12,601 (+7.1%)

$603,400 + $413,600

$1,017,000

2019

$11,762 (+3.9%)

$530,300 + $441,000

$971,300

2018

$11,321 (+5.4%)

$500,100 + $428,600

$928,700

2017

$10,739 (+6.7%)

$470,800 + $403,700

$874,500

2016

$10,068 (+3.1%)

$470,800 + $391,200

$862,000

2015

$9,763 (+7.1%)

$427,900 + $376,300

$804,200

2014

$9,115 (+0.6%)

$356,600 + $363,400

$720,000

2013

$9,065 (+2.6%)

$356,600 + $353,300

$709,900

2012

$8,831 (+3.7%)

$356,600 + $347,100

$703,700

2011

$8,515 (+0.2%)

$356,600 + $347,100

$703,700

2010

$8,500 (+2.1%)

$382,200 + $356,300

$738,500

2009

$8,323

$382,200 + $356,300

$738,500

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

Public record

Beds

Baths

2.25

Stories

Lot width

—

Lot depth

—

Lot size

15,100

Year renovated

2024

Sq. Ft.

2,397

Year built

1963

Style

Single Family Residential

County

Middlesex County

APN

1782177S

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jun 11, 2024.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Open Parking Spaces: 4
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Garage Faces Side, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 234
Length: 18
Width: 13
Level: Second
Features: Bathroom - Full,Flooring - Hardwood,Flooring - Wall to Wall Carpet,Closet,Closet/Cabinets - Custom Built

Bedroom #2 Information
Area: 143
Length: 13
Width: 11
Level: Second
Features: Flooring - Hardwood,Closet

Bedroom #3 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Flooring - Hardwood,Closet

Bedroom #4 Information
Area: 130
Length: 13
Width: 10
Level: Second
Features: Flooring - Hardwood,Closet

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 45
Length: 9
Width: 5
Level: Second
Features: Bathroom - Full

Bathroom #2 Information
Area: 42
Length: 7
Width: 6
Level: Second
Features: Bathroom - Full

Bathroom #3 Information
Level: First
Features: Bathroom - Half

Living Room Information
Area: 247
Length: 19
Width: 13
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box

Dining Room Information
Area: 156
Length: 13
Width: 12
Level: First
Features: Flooring - Hardwood,Closet/Cabinets - Custom Built

Kitchen Information
Area: 338
Length: 26
Width: 13
Level: First
Features: Flooring - Hardwood,Dining Area,Closet/Cabinets - Custom Built,Window(s) - Picture,Flooring - Vinyl

Office Room Information
Area: 104
Length: 13
Width: 8
Level: First
Features: Flooring - Vinyl

Basement Information
Basement: Full, Partially Finished, Interior Entry, Bulkhead

Laundry Information
Laundry Dimen: 9X8
Laundry Features: Bathroom - Half, Laundry Closet, Closet/Cabinets - Custom Built, First Floor, Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3
Fireplace Features: Kitchen, Living Room, Master Bedroom

Appliances
Appliances: Water Heater

Interior Features
# of Rooms (Total): 9
Flooring: Tile, Vinyl, Carpet, Hardwood, Flooring - Vinyl, Flooring - Stone/Ceramic Tile
Interior Features: Closet, Bathroom - Half, Closet/Cabinets - Custom Built, Office, Foyer, Play Room, Game Room, Mud Room, Laundry Chute

Exterior

Building Information
Building Area (Total): 2,397
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate
Color: white

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio

Property Information
PropertySubType: Single Family Residence
Other Structures: Workshop

Lot Information
Lot Size (Acres): 0.35
Lot Features: Corner Lot, Level
Frontage Length: 246
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $8,515
Tax Year: 2011

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup
Sewer: Public Sewer, City/Town Sewer
Water Source: Public, City/Town Water
Electric: Fuses

Heating & Cooling
Has Heating
Heating: Forced Air, Natural Gas, Electric, Fireplace
Cooling: Whole House Fan

Location

School Information
Elementary School: Lincoln
Middle Or Junior School: Mccall
High School: Whs

Location Information
Directions: Highland to Pierrepont to Hollywood to Dennett. Located at corner of Hollywood and Dennett.
UnparsedAddress: 23 Dennett Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, Public School, T-Station

Public facts

Beds: 4
Baths: 2.25
Sq. Ft.: 2,397
Stories: 2.0
Parking Spaces: 4
Basement: Yes
Accessible: No
Lot Size: 0.35 acres
Style: Single Family Residential
Year Built: 1963
Year Renovated: 2024
County: Middlesex County
APN: 1782177S
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jun 11, 2024

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
StandardStatus: Closed

Around this home

Schools
Places
Transit

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

2/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 hot days expected this year, 14 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

$1.65M – $2.00M

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New listings for sale in 01890

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Home values near 23 Dennett Rd

Data from public records.

Address	Redfin Estimate
17 Dennett Road, Winchester, MA 3 Beds \| 2.5 Baths \| 2283 Sq. Ft.	$1,795,758
20 Dennett Road, Winchester, MA 4 Beds \| 2.5 Baths \| 3442 Sq. Ft.	$1,849,312

Address	Redfin Estimate
19 Dennett Road, Winchester, MA 4 Beds \| 3 Baths \| 2706 Sq. Ft.	$1,770,888
14 Dennett Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2485 Sq. Ft.	$1,705,310

Address	Redfin Estimate
21 Dennett Road, Winchester, MA 3 Beds \| 3.5 Baths \| 3429 Sq. Ft.	$1,797,846
10 Dennett Road, Winchester, MA 4 Beds \| 3 Baths \| 2485 Sq. Ft.	$1,707,683

Property information provided by MLS PIN when last listed in 2011. This data may not show owner updates. Learn more.

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