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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
21years of experience
22sales in the last 12 months
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

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

Victoria Kustov, Realtor, Elite Realty Experts

Victoria Kustov

Completed Profile
4 reviews
Open 10:00 AM - 6:00 PM
Usually responds in 1 hr
22 years of experience
29 sales in last 12 months
Serves Winchester

About

Vicky Kustov, a highly acclaimed Realtor with 20+ years of experience, and her husband Paul Kustov, form a dynamic real estate duo serving Burlington, MA, and surrounding towns, including Billerica, Woburn, Wilmington, Bedford, Chelmsford, Westford, Reading, Stoneham, Wakefield, and Tewksbury. With a proven track record of selling single-family homes, condos, multi-family homes, and new construction homes, they've earned a reputation for expertise, integrity, and exceptional client service. Vicky holds prestigious designations, including CRS, ABR, SRES, and SRS, and has received multiple awards, including 'Who's Who in Real Estate' by Boston Agent Magazine and Top Agent by Fast Expert. With 84+ 5-star reviews on Zillow, 70+ 5-star reviews on Google, and 29+ 5-star reviews on Realtor.com, they're the trusted partner in buying and selling homes in the region.

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Achievements

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Top Burlington Brokerage 2025
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Top Producer 2025
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Top Listing Agent 2025

2018-2022 Client Satisfaction Award by American Institute of Real Estate Professionals; 2018-2022 Who's Who by Boston Agent Magazine

CRS, SRES, SRS, ABR

Business Highlights

1031 Tax Exchange, Buyer Representative, Concierge Services, Condominiums
Certified Residential Specialist (CRS); Seller Representative Specialist (SRS); The Seniors Real Estate Specialist (SRES); Accredited Buyer's Representative (ABR)
Foreclosure & Short Sale Specialist
Personalized Service with Strong Negotiation Skills

Coldwell Banker Realty

Anne Kennedy

Completed Profile
Open 8:00 AM - 6:00 PM
Usually responds in 30 minutes
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, Licensed real estate agent, 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

Compass

Patti Brainard

1 year of experience
111 sales in last 12 months
Serves Winchester

About

Patti Brainard is a Real Estate Agent in Winchester, MA with the brokerage Compass. Over the last 1 years we have tracked null MLS listings by Patti.

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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, Licensed real estate agent, SRES, GREEN

Charles Ginsberg's Video

Century 21 Adams

Anne Mahon

7 years of experience
Serves Winchester

About

Anne Mahon is a Real Estate Agent in Winchester, MA with the brokerage Century 21 Adams. Over the last 7 years we have tracked null MLS listings by Anne.

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Achievements

Top C21 Agent in New England 9/10/13

Bachelor's Degree, University of Rochester
MBA

REALTORĀ®

Business Highlights

New Homes, Luxury Properties, Relocation, New Construction

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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 lower this year compared to last year
Fewer sellers are listing their homes compared to last year
58
balanced market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$1.75M

Per Square Foot

$577

Days on Market

69

Total Listings

43

Market Action Index

58

Median List Price

Sun, Sep 20, 2026

Median List Price
1 Year

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