SOLD BY REDFIN JUN 2, 2025

Off market jun 2025 for $2M

$2,226,387

Est. refi paymentEst. refi $3,928/mo

•

3,039

sq ft

11 Chesterford Rd E, Winchester, MA 01890

About this home

Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly into the spacious living and family rooms—ideal for everyday living & entertaining. The main level offers three generously sized bedrooms and two full baths, including a peaceful primary suite with panoramic views, a walk-in closet, and beautifully renovated bath with two individual vanities. The lower level adds fantastic flexibility with a media room, additional bedroom, full bath, and flexible multipurpose space. Step outside to enjoy a wraparound deck and lower-level patio with direct access to the pond—perfect for kayaking, fishing, and ice skating. This is a rare and special opportunity!

Single-familyProperty Type

1927Year Built

0.31 acresLot Size

$733Est. Price/Sq.Ft.

2 garage spacesParking

Seller's agent

Joseph Pollack Redfin Corp.

Bought with Elena Langlois • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #73360401

Redfin Estimate

$2,226,387

$226K since sold in June 2025$53K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.9% higher than the average sale price ($2.01M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,200,000
A
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD AUG 7, 2026
$1,660,000
B
4 beds3.5 baths2,768 sq ft
10 Farrow St, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
C
4 beds2.5 baths3,283 sq ft
12 Yale St, 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 AUG 14, 2026
$1,325,000
E
3 beds1.5 baths2,006 sq ft
3 Chesterford Ter, Winchester, MA 01890
SOLD AUG 28, 2026
$2,300,000
F
5 beds3.5 baths5,230 sq ft
78 Bacon St, Winchester, MA 01890

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Sell

$554,047

Est. take-home

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Rent

$5,855/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

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NEW 32 HRS AGO
$18,000,000
6 beds6.5 baths10,000 sq ft
15 Vinson Cir, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$3,299,000
7 beds7.5 baths7,226 sq ft
1 Plymouth Rd, Winchester, MA 01890
OPEN SAT, 11AM TO 12:30PM
$1,299,000
6 beds2.5 baths3,910 sq ft
8 North Gtwy, Winchester, MA 01890
OPEN SAT, 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 SAT, 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 SAT, 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 11 Chesterford Rd E

Date

Event

Price

MLS PIN #73360401

Jun 2, 2025

Sold

$2,000,000

$658/sq ft

Apr 23, 2025

Contingent

—

Apr 16, 2025

Listed

$2,199,900

$724/sq ft

MLS PIN #72981610

Aug 25, 2022

Sold

$1,800,000

$592/sq ft

Jul 5, 2022

Contingent

—

Jun 14, 2022

Price Changed

$1,799,000

$592/sq ft

May 25, 2022

Price Changed

$1,999,000

$658/sq ft

May 13, 2022

Listed

$2,199,000

$724/sq ft

+37

MUST SEE this delightful WATERFRONT home nestled alongside Little Winter (skating) pond with fabulous views! This updated contemporary designed home features a stunning easy access entry, vaulted ceilings and walls of windows showcasing the spectacular setting. Updated kitchen w/ adjacent dining room w/ built in bench flows into the living room w/fplc & family room flooded with natural light w/water views from the many windows & slider to the gorgeous new deck. The main level also offers 3 bedrooms and 2 full baths; awake each morning in the relaxing Master suite w/unsurpassed views, oversized walk-in closet & new bath. The lower level includes a large media room, bedroom, full bath and gym. There are water views from almost every room in this home! The wrap around deck is perfect for enjoying the scenery and for summertime bbq's. There is a lower patio on the water making it easy to canoe/kayak & fish from your own front yard! Enjoy living an active lifestyle in this very special home

MLS PIN #71582868

Dec 12, 2013

Sold

$1,246,100

$410/sq ft

Nov 1, 2013

Contingent

—

Oct 3, 2013

Relisted

—

Sep 16, 2013

Contingent

—

Sep 13, 2013

Listed

$1,199,000

$395/sq ft

+20

Extraordinary, waterfront home on Little Winter Pond. 1 of only 5 residences, where privacy and tranquility abound. Envision yourself at the end of the day, enjoying the serenity of a waterfront home, while less than 10 miles from Downtown Boston. Truly turnkey, this graceful and well designed space is in immaculate condition. Boasting water views from virtually every room. Open floor plan with a fantastic layout- and deck- for entertaining. Spacious master suite with sweeping vistas from the oversized windows. C/Air. Spanish tiled roof that never needs replacing. Finished lower level includes home office,a terrific family or media room, full bath as well as access to the 2 car garage. Truly a rare offering; Front row access to fishing and canoeing right from your backyard, and skating in the winter; scenes that take a page straight from Currier & Ives! Not to be missed.

MLS PIN #71121624

Oct 29, 2010

Sold

$960,000

$316/sq ft

Sep 8, 2010

Contingent

—

Aug 10, 2010

Listed

$1,079,900

$355/sq ft

Public Records

Nov 30, 1998

Sold

$589,000

$194/sq ft

Public Records

Jun 26, 1987

Sold

$331,000

$109/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$19,638 (+4.2%)

$1,032,500 + $739,900

$1,772,400

2025

$18,846 (+3.9%)

$1,032,500 + $666,900

$1,699,400

2023

$18,140 (+2.3%)

$1,032,500 + $664,900

$1,697,400

2022

$17,728 (+2.7%)

$836,700 + $580,400

$1,417,100

2021

$17,268 (+14.1%)

$765,500 + $580,400

$1,345,900

2020

$15,132 (+0.8%)

$640,900 + $580,400

$1,221,300

2019

$15,006 (+3.9%)

$658,700 + $580,400

$1,239,100

2018

$14,448 (+1.0%)

$616,800 + $568,400

$1,185,200

2017

$14,311 (+8.7%)

$616,800 + $548,600

$1,165,400

2016

$13,165 (−3.8%)

$616,800 + $510,300

$1,127,100

2015

$13,683 (+6.2%)

$616,800 + $510,300

$1,127,100

2014

$12,883 (+5.2%)

$560,800 + $456,800

$1,017,600

2013

$12,248 (+1.8%)

$516,300 + $442,800

$959,100

2012

$12,037 (−5.3%)

$516,300 + $442,800

$959,100

2011

$12,705 (+8.0%)

$516,300 + $533,700

$1,050,000

2010

$11,762 (+2.1%)

$524,300 + $497,600

$1,021,900

2009

$11,517

$524,300 + $497,600

$1,021,900

Tax history for 11 Chesterford Rd E

Year

Property tax

Land + Additions

Assessment*

2026

$19,638 (+4.2%)

$1,032,500 + $739,900

$1,772,400

2025

$18,846 (+3.9%)

$1,032,500 + $666,900

$1,699,400

2023

$18,140 (+2.3%)

$1,032,500 + $664,900

$1,697,400

2022

$17,728 (+2.7%)

$836,700 + $580,400

$1,417,100

2021

$17,268 (+14.1%)

$765,500 + $580,400

$1,345,900

2020

$15,132 (+0.8%)

$640,900 + $580,400

$1,221,300

2019

$15,006 (+3.9%)

$658,700 + $580,400

$1,239,100

2018

$14,448 (+1.0%)

$616,800 + $568,400

$1,185,200

2017

$14,311 (+8.7%)

$616,800 + $548,600

$1,165,400

2016

$13,165 (−3.8%)

$616,800 + $510,300

$1,127,100

2015

$13,683 (+6.2%)

$616,800 + $510,300

$1,127,100

2014

$12,883 (+5.2%)

$560,800 + $456,800

$1,017,600

2013

$12,248 (+1.8%)

$516,300 + $442,800

$959,100

2012

$12,037 (−5.3%)

$516,300 + $442,800

$959,100

2011

$12,705 (+8.0%)

$516,300 + $533,700

$1,050,000

2010

$11,762 (+2.1%)

$524,300 + $497,600

$1,021,900

2009

$11,517

$524,300 + $497,600

$1,021,900

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.31 Acres

Year renovated

—

Sq. Ft.

2,955

Year built

1927

Style

Single Family Residential

County

Middlesex County

APN

2309861S

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, Under, Garage Door Opener, Heated Garage, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 286
Length: 22
Width: 13
Level: First
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Ceiling Fan(s),Walk-In Closet(s),Flooring - Wall to Wall Carpet,Window(s) - Picture,Recessed Lighting

Bedroom #2 Information
Area: 132
Length: 12
Width: 11
Level: First
Features: Vaulted Ceiling(s),Closet,Flooring - Hardwood,Window(s) - Picture

Bedroom #3 Information
Area: 110
Length: 11
Width: 10
Level: First
Features: Cathedral Ceiling(s),Closet,Flooring - Hardwood,Window(s) - Picture

Bedroom #4 Information
Area: 195
Length: 15
Width: 13
Level: Basement
Features: Closet,Flooring - Wall to Wall Carpet,Window(s) - Picture,Recessed Lighting

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 72
Length: 9
Width: 8
Level: First
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Closet - Linen,Flooring - Stone/Ceramic Tile,Window(s) - Picture,Recessed Lighting

Bathroom #2 Information
Area: 56
Length: 8
Width: 7
Level: First
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile,Window(s) - Picture,Lighting - Sconce

Bathroom #3 Information
Area: 60
Length: 12
Width: 5
Level: Basement
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile

Living Room Information
Area: 266
Length: 19
Width: 14
Level: First
Features: Flooring - Hardwood,Window(s) - Picture,Open Floorplan,Recessed Lighting,Window Seat

Family Room Information
Area: 182
Length: 14
Width: 13
Level: First
Features: Skylight,Flooring - Hardwood,Window(s) - Picture,Deck - Exterior,Exterior Access,Open Floorplan,Recessed Lighting,Slider

Dining Room Information
Area: 81
Length: 9
Width: 9
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Lighting - Overhead

Kitchen Information
Area: 170
Length: 17
Width: 10
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Countertops - Stone/Granite/Solid,Cabinets - Upgraded,Exterior Access,Open Floorplan,Recessed Lighting,Stainless Steel Appliances,Gas Stove

Basement Information
Basement: Full, Finished, Walk-Out Access, Interior Entry, Garage Access

Laundry Information
Laundry Dimen: 6X5
Laundry Features: In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 16
Window Features: Window(s) - Picture
Flooring: Wood, Tile, Flooring - Stone/Ceramic Tile
Interior Features: Bathroom - Half, Recessed Lighting, Closet, Closet/Cabinets - Custom Built, Entrance Foyer, Media Room, Bonus Room, 1/4 Bath

Exterior

Building Information
Building Area (Total): 3,039
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: Cream

Exterior Features
Fencing: Fenced
Roof: Tile
Patio And Porch Features: Deck - Exterior, Deck, Patio
Exterior Features: Deck, Patio, Rain Gutters, Fenced Yard, Garden

Property Information
PropertySubType: Single Family Residence
Has Waterview
Pond

Lot Information
Lot Size (Acres): 0.31
Lot Features: Wooded
ViewYN: Has View
View: Scenic View(s)
WaterfrontYN: Yes
Road Frontage Type: Private Road

Financial

Tax Information
Tax Annual Amount: $18,846
Tax Year: 2025

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

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

Location

Location Information
Directions: Woodside Rd to Chesterford Road East
UnparsedAddress: 11 Chesterford Rd E, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Public School

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,955
Stories: 1.0
Lot Size: 0.31 acres
Style: Single Family Residential
Year Built: 1927
Year Renovated: —
County: Middlesex County
APN: 2309861S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 6

Listing Information
StandardStatus: Closed

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.3mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.9mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.8mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

$2.12M – $2.56M

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Home values near 11 Chesterford Rd E

Data from public records.

Address	Redfin Estimate
8 Chesterford Rd E, Winchester, MA 4 Beds \| 2.5 Baths \| 2382 Sq. Ft.	$1,484,939
10 Chesterford Rd E, Winchester, MA 3 Beds \| 2.5 Baths \| 1664 Sq. Ft.	$1,355,965

Address	Redfin Estimate
4 Chesterford Rd, Winchester, MA 5 Beds \| 2.5 Baths \| 3466 Sq. Ft.	$1,709,886
5 Chesterford Rd E, Winchester, MA 4 Beds \| 3 Baths \| 3195 Sq. Ft.	$2,325,194

Address	Redfin Estimate
8 Chesterford Rd E, Winchester, MA 3 Beds \| 2 Baths \| 1657 Sq. Ft.	$1,359,992
3 Chesterford Rd E, Winchester, MA 1 Beds \| 1 Baths \| 1140 Sq. Ft.	$1,068,141

Property information provided by MLS PIN when last listed in 2025. This data may not match . Learn more.

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