OFF MARKET

Off market feb 2021 for $2M

$2,639,719

Est. refi paymentEst. refi $2,363/mo

•

6,437

sq ft

19 Windemere Rd, Winchester, MA 01890

About this home

Stunning Colonial with contemporary flair! As you enter the spacious foyer,you will appreciate many custom features. Bathed in natural light, with high ceilings,each room flows into the next. Open concept eat-in gourmet kitchen with island is perfect for entertaining, with easy access to backyard and patio. Enjoy family gatherings in spacious formal dining room. As the unique layout continues with formal living room and generous size family room each boasting its own fireplace. The second floor stairwell with Brazilian Cherry flooring leads to four bedrooms and separate laundry. Private master suite on third level will wow you in every way! High ceilings, fireplace, walk-in closet and designer bath with double vanity, separate shower and soaking tub makes this space feel like a Spa get-away. Adjacent room with balcony is great for home office etc.Large finished basement with cedar storage, bar area and more,,This beautiful home is is ideal for extended family, au pair or in laws.

Single-familyProperty Type

1969Year Built

0.37 acresLot Size

$410Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Cathy Paolillo • Coldwell Banker Realty - Winchester

Bought with Yuqian Han • FlyHomes Brokerage LLC

Redfin checked: 2 minutes ago

•Source:MLS PIN #72681452

Redfin Estimate

$2,639,719

$580K since sold in February 2021$33K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.9% higher than the average sale price ($2.11M) of 6 comparable homes.

SOLD OCT 15, 2026
$3,000,000
A
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
SOLD JUN 29, 2026
$2,549,000
B
4 beds4 baths5,674 sq ft
10 Viking Rd, Winchester, MA 01890
SOLD AUG 21, 2026
$1,775,000
C
5 beds3 baths3,315 sq ft
8 Hawthorne Rd, Winchester, MA 01890
SOLD JUL 29, 2026
$1,360,000
D
4 beds3 baths4,062 sq ft
15 Thornberry Rd, Winchester, MA 01890
SOLD MAR 19, 2026
$2,100,000
E
5 beds4.5 baths3,191 sq ft
10 Hawthorne Rd, Winchester, MA 01890
SOLD JUL 9, 2026
$1,899,000
F
5 beds2.5 baths3,278 sq ft
105 Thornberry Rd, Winchester, MA 01890

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Sell

$1,046,895

Est. take-home

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Rent

$6,263/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated October 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

NEW 23 HRS AGO
$1,599,000
3 beds2.5 baths1,920 sq ft
9 Watson Pl, Winchester, MA 01890
OPEN SUN, 11AM TO 12PM
$1,449,000
4 beds2.5 baths2,855 sq ft
15 Madison Ave W, Winchester, MA 01890
OPEN TODAY, 12PM TO 1PM
$649,000
3 beds1 bath1,422 sq ft
421 Washington St #421, Winchester, MA 01890
OPEN TODAY, 12PM TO 1PM
$675,000
3 beds1 bath1,524 sq ft
419 Washington St #419, Winchester, MA 01890
OPEN SUN, 12PM TO 1PM
$1,749,000
4 beds2.5 baths3,757 sq ft
85 High St, Winchester, MA 01890
OPEN SUN, 11AM TO 12:30PM
$1,049,900
3 beds2 baths1,783 sq ft
28 Olive St, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 19 Windemere Rd

Date

Event

Price

MLS PIN #72681452

Feb 1, 2021

Sold

$2,060,000

$320/sq ft

Dec 15, 2020

Contingent

—

Oct 31, 2020

Relisted

—

Oct 30, 2020

Listing Removed

—

Oct 22, 2020

Price Changed

$2,095,000

$325/sq ft

Aug 28, 2020

Price Changed

$2,125,000

$330/sq ft

Jun 26, 2020

Listed

$2,225,000

$346/sq ft

MLS PIN #71889783

Dec 4, 2015

Listing Removed

—

Dec 3, 2015

Sold

$2,035,000

$316/sq ft

Nov 3, 2015

Pending

—

Sep 17, 2015

Contingent

—

Aug 21, 2015

Pending

—

Aug 14, 2015

Listed

$2,099,000

$326/sq ft

+13

WELCOME TO WINDEMERE! TOTALLY RENOVATED and GORGEOUS colonial on a private dead end street, in the VINSON OWEN school district! Walk into the grand foyer with CUSTOM BRAZILIAN CHERRY STAIRWELL leading to the 2nd and 3rd floors. First floor features an oversized, fireplaced living room, large kitchen fully equipped with top of the line SS appliances and granite countertops. A large dining room, and an exceptional family room, boasting windows all around, 12' CEILINGS access to the PATIO and AN IMPRESSIVE CHERRY AND MARBLE fireplace. The master suite will not disappoint, it's own "wing" of the house, featuring an OVERSIZE WALK IN CLOSET, a fireplaced sitting room WITH PRIVATE BALCONY, and a SPA LIKE bathroom with GENEROUS walk in shower, and stand alone tub. There are 4 additional bedrooms, plenty of space for the family to spread out. PLUS an additional playroom just for the kids! LARGE FINISHED BASEMENT. LARGE, PRIVATE and beautifully landscaped back yard!

MLS PIN #71722942

Nov 14, 2014

Sold

$950,000

$148/sq ft

Sep 23, 2014

Contingent

—

Aug 1, 2014

Listed

$999,900

$155/sq ft

+12

Looking for a home with space galore? This well-built split-level home on the Westside is just a five minute walk to the new Vinson-Owen School! The gracious entry welcomes one to a custom home, perfect for an active family --- entertaining will be a pleasure! With the extra large living room and dining room adjacent to the large kitchen, this home is perfect for holiday gatherings. Shiny hardwood floors are in all four of the bedrooms, along with ample closet space. On the lower levels are two family rooms with the larger room featuring a beautiful fireplace and room for all kinds of exercise equipment for a home gym. From the deck, one can enjoy the lovely backyard with its mature plantings and well kept lawn with plenty of room for the active gardener to plant more flowers! The location is perfect for an easy commute to all major highways and just a short walk to the Smith Pond conservation area...a great opportunity to own a nice home!

Public Records

Sep 13, 1988

Sold

$365,000

$57/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$27,212 (+3.4%)

$1,079,800 + $1,376,200

$2,456,000

2025

$26,308 (+10.4%)

$1,042,600 + $1,329,600

$2,372,200

2023

$23,821 (−9.0%)

$968,100 + $1,229,900

$2,198,000

2022

$26,188 (+5.0%)

$782,000 + $1,311,400

$2,093,400

2021

$24,947 (+4.5%)

$633,000 + $1,311,400

$1,944,400

2020

$23,878 (+4.6%)

$595,800 + $1,331,400

$1,927,200

2019

$22,837 (+2.3%)

$558,500 + $1,327,300

$1,885,800

2018

$22,314 (+6.3%)

$538,100 + $1,292,400

$1,830,500

2017

$20,991 (+60.9%)

$479,400 + $1,230,000

$1,709,400

2016

$13,044 (+48.6%)

$479,400 + $637,400

$1,116,800

2015

$8,776 (−2.9%)

$400,300 + $322,600

$722,900

2014

$9,034 (+4.6%)

$400,300 + $313,300

$713,600

2013

$8,636 (+1.7%)

$363,000 + $313,300

$676,300

2012

$8,488 (+3.7%)

$363,000 + $313,300

$676,300

2011

$8,183 (−0.7%)

$363,000 + $313,300

$676,300

2010

$8,237 (+2.1%)

$389,100 + $326,500

$715,600

2009

$8,065

$389,100 + $326,500

$715,600

Tax history for 19 Windemere Rd

Year

Property tax

Land + Additions

Assessment*

2026

$27,212 (+3.4%)

$1,079,800 + $1,376,200

$2,456,000

2025

$26,308 (+10.4%)

$1,042,600 + $1,329,600

$2,372,200

2023

$23,821 (−9.0%)

$968,100 + $1,229,900

$2,198,000

2022

$26,188 (+5.0%)

$782,000 + $1,311,400

$2,093,400

2021

$24,947 (+4.5%)

$633,000 + $1,311,400

$1,944,400

2020

$23,878 (+4.6%)

$595,800 + $1,331,400

$1,927,200

2019

$22,837 (+2.3%)

$558,500 + $1,327,300

$1,885,800

2018

$22,314 (+6.3%)

$538,100 + $1,292,400

$1,830,500

2017

$20,991 (+60.9%)

$479,400 + $1,230,000

$1,709,400

2016

$13,044 (+48.6%)

$479,400 + $637,400

$1,116,800

2015

$8,776 (−2.9%)

$400,300 + $322,600

$722,900

2014

$9,034 (+4.6%)

$400,300 + $313,300

$713,600

2013

$8,636 (+1.7%)

$363,000 + $313,300

$676,300

2012

$8,488 (+3.7%)

$363,000 + $313,300

$676,300

2011

$8,183 (−0.7%)

$363,000 + $313,300

$676,300

2010

$8,237 (+2.1%)

$389,100 + $326,500

$715,600

2009

$8,065

$389,100 + $326,500

$715,600

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.37 Acres

Year renovated

2010

Sq. Ft.

5,715

Year built

1969

Style

Single Family Residential

County

Middlesex County

APN

3799167S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Property details

Parking

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

Interior

Master Bedroom Information
Area: 360
Length: 18
Width: 20
Level: Third
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting

Bedroom #2 Information
Area: 180
Length: 12
Width: 15
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 154
Length: 11
Width: 14
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 169
Length: 13
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #5 Information
Area: 168
Length: 12
Width: 14
Level: Second
Features: Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full

Bathroom #3 Information
Level: Second
Features: Bathroom - Full

Living Room Information
Area: 378
Length: 18
Width: 21
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Open Floorplan,Recessed Lighting

Family Room Information
Area: 440
Length: 20
Width: 22
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Balcony - Exterior,Cable Hookup,Exterior Access,Recessed Lighting

Dining Room Information
Area: 289
Length: 17
Width: 17
Level: Main,First
Features: Flooring - Hardwood,Window(s) - Picture

Kitchen Information
Area: 323
Length: 17
Width: 19
Level: Main,First
Features: Flooring - Hardwood,Kitchen Island,Cabinets - Upgraded,Recessed Lighting,Slider,Stainless Steel Appliances

Office Room Information
Level: Third
Features: Flooring - Hardwood,Balcony - Exterior

Basement Information
Basement: Full, Partially Finished, Bulkhead

Laundry Information
Laundry Features: Dryer Hookup - Electric, Washer Hookup, Second Floor

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

Interior Features
# of Rooms (Total): 12
Flooring: Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet
Interior Features: Countertops - Stone/Granite/Solid, Wet Bar, Cedar Closet(s), Bathroom - 3/4, Home Office, Bonus Room, Game Room, Bathroom, Central Vacuum

Exterior

Building Information
Building Area (Total): 6,437
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: Grey

Exterior Features
Roof: Shingle
Exterior Features: Balcony - Exterior

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.37
Lot Features: Cul-De-Sac, Level
Road Frontage Type: Private Road, Dead End

Financial

Tax Information
Tax Annual Amount: $23,878
Tax Year: 2020

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

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

Location

Location Information
Directions: Cox Road to Windemere Road
UnparsedAddress: 19 Windemere Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway Access, Public School

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,715
Stories: 2.0
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1969
Year Renovated: 2010
County: Middlesex County
APN: 3799167S

Home facts updated by county records on Sep 16, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

K - 12
Preschool & daycare

Vinson-Owen Elementary School

Public PreK-5 • Assigned • 0.4mi

9/10

McCall Middle School

Public 6-8 • Assigned • 2.2mi

9/10

Winchester High School

Public 9-12 • Assigned • 2.4mi

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

50% 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 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.51M – $3.04M

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Home values near 19 Windemere Rd

Data from public records.

Address	Redfin Estimate
110 Johnson Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 2598 Sq. Ft.	$1,458,139
249 High St, Winchester, MA 4 Beds \| 2.5 Baths \| 3488 Sq. Ft.	$1,709,498
14 Cox Rd, Winchester, MA 3 Beds \| 3 Baths \| 4137 Sq. Ft.	$1,818,288
6 Cox Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2053 Sq. Ft.	$1,592,220
5 Cox Rd, Winchester, MA 4 Beds \| 3.5 Baths \| - Sq. Ft.	$2,022,532
15 Cox Rd, Winchester, MA 5 Beds \| 4.5 Baths \| 5533 Sq. Ft.	$2,345,131
21 Cox Rd, Winchester, MA 5 Beds \| 4.5 Baths \| 4800 Sq. Ft.	$2,782,234

Address	Redfin Estimate
114 Johnson Rd, Winchester, MA 3 Beds \| 3 Baths \| 3182 Sq. Ft.	$2,092,366
24 Cox Rd, Winchester, MA 6 Beds \| 3 Baths \| 3500 Sq. Ft.	$1,789,694
12 Cox Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 2818 Sq. Ft.	$2,001,152
4 Cox Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2053 Sq. Ft.	$1,610,563
7 Cox Rd, Winchester, MA 2 Beds \| 1 Baths \| 1708 Sq. Ft.	$1,303,854
17 Cox Rd, Winchester, MA 5 Beds \| 4.5 Baths \| 4660 Sq. Ft.	$2,530,068
2 Valleywood Cir, Winchester, MA 3 Beds \| 2.5 Baths \| 2484 Sq. Ft.	$1,377,317

Address	Redfin Estimate
120 Johnson Rd, Winchester, MA 4 Beds \| 3 Baths \| 3494 Sq. Ft.	$1,664,844
18 Cox Rd, Winchester, MA 3 Beds \| 1.5 Baths \| 1248 Sq. Ft.	$1,766,912
10 Cox Rd, Winchester, MA 6 Beds \| 4 Baths \| 4690 Sq. Ft.	$2,505,484
247 High St, Winchester, MA 3 Beds \| 4 Baths \| 4078 Sq. Ft.	$2,040,831
11 Cox Rd, Winchester, MA 5 Beds \| 5 Baths \| 3470 Sq. Ft.	$2,469,904
19 Cox Rd, Winchester, MA 3 Beds \| 1.5 Baths \| 2351 Sq. Ft.	$1,649,844
115 Johnson Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2276 Sq. Ft.	$1,369,011

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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