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MassachusettsWinchester

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Featured Agents in Winchester, MA

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PRIME AGENT
Deborah Miller profile picture
Littlefield Real Estate

Deborah Miller

Completed Profile
2 reviews
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22years of experience
17sales in the last 12 months
150transactions all-time
Prime Agent Badge
PRIME AGENT
Druann Jedrey profile picture
Leading Edge Real Estate

Druann Jedrey

10 reviews
View Profile
19years of experience
22sales in the last 12 months
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

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
24 years of experience
36 sales in last 12 months
604 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 throughout the real estate process! Kathleen started The Creative Living Team because we as humans work best in community. Our Team focuses on properties throughout Boston, Brookline, Newton, Jamaica Plain, South Boston, Charlestown, Roslindale, Cambridge, Somerville, Dorchester, Roxbury and East Boston. As a team, we have 40+ cumulative years of real estate experience, $290+ million in sales, and have sold over 470 homes. We have assisted landlords and tenants with hundreds of rentals. As first-time buyer and seller specialists, we are experienced at educating and guiding clients through the process of selling or buying their first home. We also specialize in working with investors on multi-family buildings and understand the frustrations and delicacies of this. How can we help you?

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Achievements

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Top Listing Agent 2025
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Top Buyer's Broker 2025
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Sells Homes Fast 2025

Five Star Professional, 9 year Award Winner, 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 through the process of selling or buying their first home.
We are International Luxury Home Marketing specialists, providing red carpet service and results for all our properties.
We specialize in multi-family buildings, probate and downsizing and understand how to delicately handle tenant situations.

Coldwell Banker Realty

Anne Kennedy

Completed Profile
Open 8:00 AM - 7:00 PM
Usually responds in 30 minutes
Prime Agent Badge
PRIME AGENT
10 years of experience
25 sales in last 12 months
144 transactions all-time
Serves Winchester

About

Anne offers seamless, concierge-level support for all her clients, guiding each step with precision and care. She artfully crafts a narrative for every property, meticulously analyzing market trends to position homes competitively and at precisely the opportune moment. Anne's insights transcend the transactional; her keen eye for staging, upgrading, and repurposing becomes a transformative force, elevating property values while diminishing time spent on the market. Anne leverages her formidable arsenal of innovative marketing tools across a myriad of platforms, from captivating online showcases to tailored e-blasts, mailings, and unforgettable open-house events. Recognizing the emotional weight that accompanies selling or buying a home, Anne's grace and expertise ensure a stress-free journey for her clients. Her wealth of experience in construction affords her an intimate understanding of every facet of a home, from the foundation to the roof. See Anne's reviews on Zillow and Google!

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Achievements

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Top Producer 2025
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Top Listing Agent 2025
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Top Buyer's Broker 2025

Real Trends/Tom Ferry Top Producer 2022,2023.Boston Magazine Top Agent 2022, 2023. Coldwell Banker International President's Elite, Top 100 Agent in New England

Bachelor's Degree, University College Cork
Economics , 1982 - 1985

ABR, e-PRO, REALTORĀ®, SFR, GREEN, SRES, CLHMS, Pricing Strategy Advisor

Business Highlights

New Homes, Luxury Properties, Relocation, New Construction
Comparative Market Analysis of your home
Complementary Home Staging services
Single family, Condominium and Multi-family homes

Coldwell Banker Realty

Charles Ginsberg

Completed Profile
6 reviews
Open 9:00 AM - 9:00 PM
Usually responds in 10 minutes
22 years of experience
15 sales in last 12 months
271 transactions all-time
Serves Winchester

About

I have been a full-time real estate agent since 2003. I am hands on and with you throughout the whole process. I treat your money as if it were mine. "If you are SELLING your property, I will get you the highest sale price possible by marketing it to the most ready, willing and able buyers. Very simply, the more looks, the more offers. If you are BUYING, it is my job to give you ALL the discoverable information about the property you desire, so that you can make a well-informed decision if it is for you and if so, then to make your offer stand it so that it is the one chosen. Whether you are buying or selling a property, it is my job to look out for your interests only."

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Achievements

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Top Negotiator 2025
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Top Listing Agent 2025

Bachelor's Degree, University of Arizona
agriculture

e-PRO, ABR, REALTORĀ®, SRES, GREEN

Charles Ginsberg's Video

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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Prudential Preferred Realty

Jennifer Keenan

16 years of experience
3 sales in last 12 months
Serves Winchester

About

Jennifer Keenan is a Real Estate Agent in Winchester, MA with the brokerage Prudential Preferred Realty. Over the last 16 years we have tracked null MLS listings by Jennifer.

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Achievements

Graduate Degree, Stonehill and Lesley
BS and MS

REALTORĀ®

Business Highlights

Buyer Representative, First Time Buyers, New Construction, New Homes

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

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    "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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    Jon B. from Wisconsin / Bought a home using RealEstateAgents.com
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    Stanley K. from Indiana / 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
100
seller's market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$2.35M

Per Square Foot

$559

Days on Market

65

Total Listings

44

Median List Price

Wed, May 6, 2026

Median List Price
1 Year

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