OFF MARKET

Off Market Sep 2019 for $999K

$1,599,622

Est. refi paymentEst. refi $4,742/mo

•

2,896

sq ft

2 Ainsworth Rd, Winchester, MA 01890

About this home

Sunny, updated 3 bed 2.5 bath cape located on a cul-de-sac near Fells Reservation in Winchester Highlands. First floor boasts open chef?s kitchen, dining area with built-ins, and family room with gorgeous vaulted ceilings. Over sized family room with beautiful fireplace and french doors that lead out to a deck overlooking your beautifully landscaped yard. Additional bedroom, separate office and full bath with custom walk in shower located on first floor. Second floor has two bedrooms and a full bath with ceramic tile shower. Large bonus rooms in walk out basement with fireplace and room for exercise equipment or toy room. Walk out of your spacious basement to a serene patio area with built in fireplace for outdoor entertaining. Gas heat, central ac, washer/dryer in basement.

Single-familyProperty Type

1937Year Built

0.33 acresLot Size

$552Est. Price/Sq.Ft.

4 spacesParking

Listed by Post Advisory Group • Engel & Volkers Boston

Bought with Post Advisory Group • Engel & Volkers Boston

Redfin checked: 3 minutes ago

•Source:MLS PIN #72535201

Redfin Estimate

$1,599,622

$601K since sold in September 2019$28K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.4% lower than the average sale price ($1.61M) of 6 comparable homes.

SOLD JUL 28, 2026
$1,738,000
A
3 beds2.5 baths2,992 sq ft
18 Grayson Rd, Winchester, MA 01890
SOLD JUL 9, 2026
$1,750,000
B
4 beds3 baths2,814 sq ft
24 Hinds Rd, Winchester, MA 01890
SOLD AUG 14, 2026
$1,500,000
C
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD JUL 6, 2026
$1,620,000
D
4 beds2.5 baths2,233 sq ft
10 Bonad Rd, Winchester, MA 01890
SOLD MAY 28, 2026
$1,330,000
E
3 beds1.5 baths2,222 sq ft
1 Orient St, Winchester, MA 01890
SOLD JUL 31, 2026
$1,700,000
F
3 beds2 baths3,090 sq ft
41 Sunset Rd, Winchester, MA 01890

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Sell

$832,345

Est. take-home

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Refinance

Est. cash available

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Rent

$5,201/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.9%

0.2% MoM

Median sale price

$1.6M

$175K MoM

Avg. days on market

19d

0 days MoM

Recently sold homes

17 MoM

New listings for sale

EARLY ACCESS
$675,000
2 beds2 baths1,124 sq ft
60 Lake St Unit E, Winchester, MA 01890
EARLY ACCESS
$1,699,000
3 beds2 baths2,327 sq ft
4 Churchill Rd, Winchester, MA 01890
3D & VIDEO TOUR
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
3D WALKTHROUGH
$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
See all

Provided by Redfin

Sale history for 2 Ainsworth Rd

Date

Event

Price

MLS PIN #72535201

Sep 19, 2019

Sold

$999,000

$345/sq ft

Aug 12, 2019

Pending

—

Jul 29, 2019

Contingent

—

Jul 16, 2019

Listed

$999,000

$345/sq ft

MLS PIN #72084049

Dec 2, 2016

Sold

$879,000

$304/sq ft

Nov 3, 2016

Pending

—

Oct 20, 2016

Listed

$879,000

$304/sq ft

+11

Beautifully expanded and updated 3 Bedroom 2 ½ Bath Cape on idyllic cul-de-sac between downtown Winchester and the tranquil Fells conservation! Winchester’s Jerome Bailey Foster designed six of the eight homes on this picturesque street which oozes charm! First floor offers gorgeous, updated granite Kitchen with Bosch and Thermador appliances. The open 30’ cathedral Family Room with handsome hearth and French doors which open to wrap-around deck, all overlooking enchanting gardens, patio and private yard. Packed with updates including luxurious Bathrooms, windows, alarm system, insulation, central air, furnace, water heater, fence and much more. Finished walk-out lower level with one of three fireplaces. Enchanting yard features perennial border gardens, mature trees and flower beds - a gardener's paradise! Steps from the Fells hiking trails, and walking distance to Kidstock theater, Muraco School and playing fields.

MLS PIN #70371045

May 19, 2006

Sold

$750,000

$259/sq ft

Apr 24, 2006

Listing Removed

—

Apr 20, 2006

Listed

$749,900

$259/sq ft

Public Records

Jul 29, 1998

Sold

$337,000

$116/sq ft

Public Records

Aug 30, 1979

Sold

$64,900

$22/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$15,334 (+6.8%)

$973,500 + $409,200

$1,382,700

2023

$14,364 (+0.3%)

$973,500 + $408,500

$1,382,000

2022

$14,326 (+9.6%)

$757,200 + $388,000

$1,145,200

2021

$13,074 (+3.6%)

$631,000 + $388,000

$1,019,000

2020

$12,625 (+6.1%)

$631,000 + $388,000

$1,019,000

2019

$11,903 (+2.6%)

$594,900 + $388,000

$982,900

2018

$11,602 (−3.9%)

$575,100 + $376,700

$951,800

2017

$12,075 (+6.6%)

$575,100 + $408,200

$983,300

2016

$11,327 (+3.5%)

$575,100 + $394,700

$969,800

2015

$10,942 (+7.4%)

$522,800 + $378,500

$901,300

2014

$10,189 (+12.6%)

$437,200 + $367,600

$804,800

2013

$9,045 (+3.2%)

$351,500 + $356,800

$708,300

2012

$8,767 (+3.7%)

$351,500 + $347,100

$698,600

2011

$8,453 (+3.5%)

$351,500 + $347,100

$698,600

2010

$8,165 (+2.1%)

$376,800 + $332,600

$709,400

2009

$7,995

$376,800 + $332,600

$709,400

Tax history for 2 Ainsworth Rd

Year

Property tax

Land + Additions

Assessment*

2025

$15,334 (+6.8%)

$973,500 + $409,200

$1,382,700

2023

$14,364 (+0.3%)

$973,500 + $408,500

$1,382,000

2022

$14,326 (+9.6%)

$757,200 + $388,000

$1,145,200

2021

$13,074 (+3.6%)

$631,000 + $388,000

$1,019,000

2020

$12,625 (+6.1%)

$631,000 + $388,000

$1,019,000

2019

$11,903 (+2.6%)

$594,900 + $388,000

$982,900

2018

$11,602 (−3.9%)

$575,100 + $376,700

$951,800

2017

$12,075 (+6.6%)

$575,100 + $408,200

$983,300

2016

$11,327 (+3.5%)

$575,100 + $394,700

$969,800

2015

$10,942 (+7.4%)

$522,800 + $378,500

$901,300

2014

$10,189 (+12.6%)

$437,200 + $367,600

$804,800

2013

$9,045 (+3.2%)

$351,500 + $356,800

$708,300

2012

$8,767 (+3.7%)

$351,500 + $347,100

$698,600

2011

$8,453 (+3.5%)

$351,500 + $347,100

$698,600

2010

$8,165 (+2.1%)

$376,800 + $332,600

$709,400

2009

$7,995

$376,800 + $332,600

$709,400

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.33 Acres

Year renovated

—

Sq. Ft.

2,896

Year built

1937

Style

Single Family Residential

County

Middlesex County

APN

797471S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 29, 2026.

Property details

Parking

Parking Information
Parking Spaces: 4
Parking Features: Off Street

Interior

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

Basement Information
Basement: Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3

Interior Features
# of Rooms (Total): 9
Flooring: Hardwood

Exterior

Building Information
Building Area (Total): 2,896
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Patio And Porch Features: Deck
Exterior Features: Deck, Balcony, Rain Gutters, Storage, Professional Landscaping, Garden, Stone Wall

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.33
Lot Features: Corner Lot

Financial

Tax Information
Tax Annual Amount: $11,902.92
Tax Year: 2019

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Highland Ave to Ainsworth Rd
UnparsedAddress: 2 Ainsworth Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,896
Stories: 2.0
Lot Size: 0.33 acres
Style: Single Family Residential
Year Built: 1937
Year Renovated: —
County: Middlesex County
APN: 797471S

Home facts updated by county records on Jul 29, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Muraco Elementary School

Public K-5 • Assigned • 0.5mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.8mi

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

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

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

60% chance of strong winds in next 30 years

3/10 Air Factor

2 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

$1.52M – $1.84M

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New listings for sale in 01890

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

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EARLY ACCESSCOMPASS COMING SOON

$1,699,000

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3D & VIDEO TOUR

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5 beds4.5 baths5,058 sq ft

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3D WALKTHROUGH

$1,699,000

5 beds3.5 baths3,180 sq ft

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Home values near 2 Ainsworth Rd

Data from public records.

Address	Redfin Estimate
4 Ainsworth Rd, Winchester, MA 4 Beds \| 2 Baths \| 2116 Sq. Ft.	$1,575,364
9 Ainsworth Rd, Winchester, MA 4 Beds \| 1 Baths \| 2100 Sq. Ft.	$1,564,891

Address	Redfin Estimate
6 Ainsworth Rd, Winchester, MA 3 Beds \| 2 Baths \| 3142 Sq. Ft.	$1,605,904
5 Ainsworth Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 3288 Sq. Ft.	$2,125,594

Address	Redfin Estimate
8 Ainsworth Rd, Winchester, MA 5 Beds \| 3 Baths \| 3400 Sq. Ft.	$1,854,266
3 Ainsworth Rd, Winchester, MA 5 Beds \| 2.5 Baths \| 2516 Sq. Ft.	$1,524,677

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

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