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Featured Agents in Winchester, MA

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Deborah Miller profile picture
Littlefield Real Estate

Deborah Miller

Completed Profile
2 reviews
View Profile
21years of experience
17sales in the last 12 months
150transactions all-time
The Shawn Sullivan Team profile picture
Re/max Andrew Realty Services

The Shawn Sullivan Team

8 reviews
View Profile
20years of experience
26sales in the last 12 months
500transactions all-time
Joelle Smith profile picture
Compass

Joelle Smith

View Profile
9years of experience
22sales in the last 12 months

Compare 15 top-performing real estate agents in Winchester, MA

Kathleen Alexander profile picture

Keller Williams Realty Boston-Metro

Kathleen Alexander

Completed Profile
6 reviews
Open 9:00 AM - 9:00 PM
Usually responds in 2 hrs
Prime Agent Badge
PRIME AGENT
23 years of experience
57 sales in last 12 months
449 transactions all-time
Serves Winchester

About

All of us on The Creative Living Team take a consultative approach with clients, partnering our expertise with you to achieve your goals while enjoying a Red Carpet experience in this crazy p…

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Achievements

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Top Listing Agent 2024
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Top Buyer's Broker 2024
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Sells Homes Fast 2024

Five Star Professional, 2019/2020/2021 Boston Award for Real Estate Services

Bachelor's Degree, Gonzaga University
Fine Arts and Marketing, 1986 - 1990

CRS, REALTORĀ®, SRS

Business Highlights

1031 Tax Exchange, Buyer Representative, Concierge Services, Condominiums
As first-time buyer and seller specialists, we are expert at educating and guiding clients throug…
We are International Luxury Home Marketing specialists, providing red carpet service and r…
We specialize in multi-family buildings, probate and downsizing and understand how to delicat…
Angelo Stifano profile picture

Century 21 Mario

Angelo Stifano

Completed Profile
15 reviews
Usually responds in 30 minutes
Prime Agent Badge
PRIME AGENT
9 years of experience
27 sales in last 12 months
198 transactions all-time
Serves Winchester

About

A seasoned professional with a robust legal background, Angelo Stifano graduated from law school in his native Venezuela in 2004, where he practiced for nearly a decade. In 2012, he move…

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Achievements

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Top Sales Producer 2024
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Sells Homes Fast 2024
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Top Buyer's Broker 2024

Emerald Top Producer 2015, Centurion Top Producer 2016 and 2017 and 2018, Double Centurion 2019, Centurion 2020 and 2021, Double Centurion 2022, Centurion 2023

Doctoral Degree, Law School "Santa Maria" University

Business Highlights

Seller Representative, Buyer Representative, Multi-Family Homes, Second Homes
Multilingual Proficiency: Fluent in English, Spanish, and Italian, enabling effective comm…
Top Team Member: Integral part of a consistently top 10 ranked team in the state, d…
Client-Centric Approach: Renowned for going above and beyond to meet clients' needs, ens…
Gerard O'connell profile picture

Coldwell Banker

Gerard O'connell

Completed Profile
11 reviews
Open 24 hours
Usually responds in 10 minutes
22 years of experience
15 sales in last 12 months
Serves Winchester

About

My goal is to make the buying or selling process as successful and stressfree as possible. To that end, I work diligently to help people make the best possible real estate decision. I am very familiar …

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Achievements

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Top Listing Agent 2024
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Top Buyer's Broker 2024
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Top Sales Producer 2024

President's Circle Designation

Master's Degree, University College Cork, Ireland.
Higher Education

Business Highlights

Buyer Representative, Condominiums, First Time Buyers, Lot/Land
Member of Coldwell Banker Meals on Wheels program.
Coached School Basketball, Soccer.
Co-ordinated with local community groups to organize sports events for local youth.
Gayle Winters profile picture

Compass

Gayle Winters

Completed Profile
Open 24 hours
Usually responds in 15 minutes
7 years of experience
59 sales in last 12 months
375 transactions all-time
Serves Winchester

About

As a premier Massachusetts Real Estate Agent ranking in the top 1% of all REALTORSĀ® nationwide, I am responsible for a wide range of sales and management duties with The Gayle Wi…

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Achievements

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Top Volume Producer 2024
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Top Luxury Buyer's Agent 2024
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Top Luxury Listing Agent 2024

Ranked Top 1% in U.S.- CRS

Bachelor's Degree
Accounting

ABR, CRS, REALTORĀ®

Business Highlights

Distressed Properties, Luxury Properties, Relocation, New Construction
Ranked Top 1% in U.S.-Former CFO-Luxury market Specialist-Sellers & Buyers
Recognized in the Wall Street Journal as Top Producing Agent for sales & volume since 2020
David Lenoir profile picture

Coldwell Banker Residential Brokerage

David Lenoir

12 years of experience
Serves Winchester

About

David Lenoir is a Real Estate Agent in Winchester, MA with the brokerage Coldwell Banker Residential Brokerage. Over the last 12 years we have tracked null MLS listings by David.

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Achievements

Graduate Degree, Boston University
MBA - Marketing

REALTORĀ®

Business Highlights

Buyer Representative, Condominiums, First Time Buyers, Luxury Properties

We've introduced over 4,940,482 buyers and sellers to top local real estate agents in the past 15 years

  • R V

    "The service was great and the recommendation of the realtor was fantastic. The realtor was fair and honest he gave me a very reasonable selling price and follow the listing all the way through. The house sold within the first week."
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    Rita V. from Tennessee / Sold a home using RealEstateAgents.com
  • A C

    "I used the website to identify potential agents in the new city I was moving too. I ultimately went with one of the recommended agents and had a very smooth home buying process."
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    Alexis C. from Iowa / Bought a home using RealEstateAgents.com
  • R J

    "My realtor was very professional in every aspect of the sale. My house sold within a week. She called or texted me through out the whole process."
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    Ruth J. from Ohio / Sold a home using RealEstateAgents.com
  • S M

    "We found an excellent Realtor, who guided us through the sale and did an excellent job along the way."
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    Steve M. from Florida / Sold a home using RealEstateAgents.com
  • J B

    "Very professional, we had a great experience."
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    Jon B. from Wisconsin / Bought a home using RealEstateAgents.com
  • S K

    "The agent you recommended was fantastic. He stayed in touch throughout the process. He kept us informed every step of the way. The sale was quick and couldn't have gone smoother. Would definitely recommend to anyone else and will definitely use in the future if needed."
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    Stanley K. from Indiana / Sold a home using RealEstateAgents.com
  • J L

    "Great realtors. My home sold in five days!"
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    Joe L. from Illinois / Sold a home using RealEstateAgents.com
  • B W

    "My selected agent was very thorough, professional, and attentive to my needs. He was absolutely the BEST!"
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    Bonnie W. from Indiana / Sold a home using RealEstateAgents.com
  • J S

    "Had issues with the title company, which agents handled."
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    John S. from Arizona / Sold a home using RealEstateAgents.com
  • J H

    "We had a very unique situation... My sister and I live in different states and the house belonged to our deceased Mother... Service was great could not have been any better..."
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    Joe H. from Texas / Sold a home using RealEstateAgents.com

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Winchester Housing Market Report

Market Action Index

We are extensively tracking the housing market in Winchester, MA. Here are the strongest factors contributing to this score:

The median prices are rising year over year
Fewer sellers are listing their homes compared to last year
78
seller's market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$2.50M

Per Square Foot

$508

Days on Market

68

Total Listings

33

Market Action Index

78

Median List Price

Sat, May 3, 2025

Median List Price
1 Year
Apr 25Jan 25Oct 24Jul 24$1.40M$1.75M$2.10M$2.45M$2.80M

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