RateMyAgentGo to search
Back 11 Chesterford Rd E
Off Market

11 Chesterford Rd E

Winchester MA 01890

4
4
4
3039 sq. ft.
13721 sq. ft.
Single-Family
Last sold for $2,000,000
Joseph PollackJoseph Pollack, last sold this property on 02 June 2025 after 43 days on market.

Overview

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!

Features

4 bedrooms
4 bathrooms
4 carspaces
2 garage spaces
3039 sq. ft. floor area
13721 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Winchester over the last 12 months, the estimated median property value of 11 Chesterford Rd E is $1.55m.

Median value
$1.55m
Estimated value range
$930k - $2.85m
Median days on market
16
Estimated value trend
-7%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Winchester. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 11 Chesterford Rd E

2025
Sold
$2,000,000
02 Jun 2025 by Joseph Pollack, of Redfin Corp.
2022
Sold
$1,800,000
25 Aug 2022
2013
Sold
$1,246,100
12 Dec 2013 by Lee Pagani, of RE/MAX Renaissance Realty

Happy sellers in Winchester

~%

We have insufficient information to provide an overview of customer satisfaction for Winchester. Viewing the agent profiles, reviews and sales for Winchester can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Winchester

In the last 12 months, 56 four-bedroom single-family properties similar to 11 Chesterford Rd E, have been sold.

This represents a 10% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winchester

placeholder
Danny Zheng

Danny Zheng is a recommended agent for Winchester.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (59 reviews)
  •  1 Review in Winchester
  •  1 Sale in Winchester
View profile
placeholder
Peter Rooney

Sellers who recommend Peter Rooney have praised them for being local expert, responsive, clear communication, supportive, friendly, hard-working, and well-prepared

  •   5   (43 reviews)
  •  1 Review in Winchester
  •  1 Sale in Winchester
View profile
placeholder
Paula Sughrue

Paula Sughrue is a recommended agent for Winchester.  They have 8 local sales across the last 12 months.

  •  8 Sales in Winchester
View profile
placeholder
McGlynn Splaine & Nigro Team

McGlynn Splaine & Nigro Team is a recommended agent for Winchester.  They have 6 local sales across the last 12 months.

  •  6 Sales in Winchester
View profile
or
Skip the list and find your ideal agent to sell your propertyFind My Agent
RateMyAgent
Sales:
(619) 566-0008
Quick Links
© 2026 RateMyAgent
Privacy PolicyTerms & ConditionsLicensingSitemap