Top Realtors and Real Estate Agents in Winchester, MA
Rankings based on verified MLS transaction data. Last updated September 2026. No pay-to-play.
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Top Agent
$2.46B
All-Time Sales
$400K - $3.1M
Price Range
5%
Negotiated Off List
Top Agent
(5)
Mary Murray
Gibson Sotheby's International Realty
39 Years of experience
9+ Sales in the last 12 months
$202.7M
All-Time Sales
$570K - $2.7M
Price Range
4%
Negotiated Off List
Top Agent$165.4M
All-Time Sales
$500K - $3.1M
Price Range
5%
Negotiated Off List
Top Agent$292.1M
All-Time Sales
$450K - $5.2M
Price Range
4%
Negotiated Off List
Top Agent(12)
Lisa Howitt
Century 21 Sexton & Donohue, Inc.
36 Years of experience
7+ Sales in the last 12 months
$235.1M
All-Time Sales
$460K - $1.6M
Price Range
4%
Negotiated Off List
Top Agent$292.6M
All-Time Sales
$680K - $3.6M
Price Range
4%
Negotiated Off List
Top Agent$1.85B
All-Time Sales
$540K - $5.1M
Price Range
5%
Negotiated Off List
Top Agent$783.3M
All-Time Sales
$550K - $5.7M
Price Range
5%
Negotiated Off List
Top Agent(31)
Cameron Chesley
CS Luxury Group - Keller Williams, Boston Metro
9 Years of experience
10+ Sales in the last 12 months
$147.5M
All-Time Sales
$830K - $4.7M
Price Range
3%
Negotiated Off List
Top AgentTop 3.42%
in Winchester, MA
$928.3M
All-Time Sales
$690K - $8.4M
Price Range
5%
Negotiated Off List
Top AgentTop 3.8%
in Winchester, MA
$216.8M
All-Time Sales
$450K - $2.7M
Price Range
4%
Negotiated Off List
Top Agent$131.2M
All-Time Sales
$450K - $1.7M
Price Range
4%
Negotiated Off List
Top AgentTop 4.17%
in Winchester, MA
$50.4M
All-Time Sales
$810K - $2.7M
Price Range
Top Agent(42)
Rebecca Riopelle
Keller Williams Eastern Middlesex
8 Years of experience
2+ Sales in the last 12 months
$86M
All-Time Sales
$390K - $1.7M
Price Range
1
Sold in Winchester, MA
Top AgentTop 4.93%
in Winchester, MA
$455.9M
All-Time Sales
$540K - $2.1M
Price Range
4%
Negotiated Off List
Top AgentTop 5.69%
in Winchester, MA
$783.2M
All-Time Sales
$960K - $5.1M
Price Range
5%
Negotiated Off List
Top Agent(55)
Charles King
Real Brokerage - The Charles King Group
15 Years of experience
111+ Sales in the last 12 months
Top 5.69%
in Winchester, MA
$414.4M
All-Time Sales
$650K - $4.1M
Price Range
4%
Negotiated Off List
Top Agent$210.7M
All-Time Sales
$470K - $2.1M
Price Range
7%
Negotiated Off List
Top Agent$131.3M
All-Time Sales
$570K - $1.8M
Price Range
6%
Negotiated Off List
Top Agent(22)
Gian-Paul Sanseverino
Coldwell Banker Realty - Lexington
12 Years of experience
20+ Sales in the last 12 months
$26.1M
All-Time Sales
$450K - $1.4M
Price Range
46
Total Number Of Homes Sold
Winchester Housing Market Trends
Homes in Winchester take a median 22 days to sell, go for 99.97% of asking, prices are up 26.3% from a year ago. Verified MLS market data through September 2026.
Market temperature
Balanced market
3.5 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$1,786,649
median sale price
How fast they sell
22 days
median time on market
Supply and competition
3.5 months
of supply on the market
The numbers speak
for Winchester.
Every agent above earned their place with closed sales, not advertising. Tell us about your home and our algorithm picks the Winchester agents whose results fit it.
Winchester agents analyzed for these rankings
days faster: top-ranked agents sell in 16 days, the Winchester market in 22
median sale price in Winchester
Do Top Winchester Agents Sell Faster?
The 19 top-ranked agents on EffectiveAgents in Winchester sell in a median of 16 days, compared with the Winchester market median of 22 days on market.
About 6 days faster (27% quicker than the Winchester market)
Median days to sale reported by the top-ranked Winchester agents on EffectiveAgents, compared with the Winchester market median days on market. Agent figures reflect each agent's reported sales history.
When Is the Best Time to Sell a House in Winchester?
Based on the last 24 months of verified MLS market data, homes in Winchester sell fastest and closest to asking when they go under contract in April. To hit that window, plan to list around March.
Median days on market by month (shorter is faster)
April
Best month to sell
18 days
Typical time on market
101.5%
Of asking price
Seasonal averages from the last 24 months of Winchester, MA sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
How We Rank Winchester Real Estate Agents
Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Winchester market today.
Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.
527
agents analyzed
15+
performance signals
$0
paid for placement
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: September 2026
Winchester Real Estate Agent FAQs
How were these Winchester real estate agents ranked?
Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.
How many real estate agents are in Winchester?
Our data covers 527 real estate agents serving the Winchester area. The count represents agents with transaction activity recorded in our Winchester market data, not simply everyone holding a license.
What does the median sale price in Winchester mean for sellers?
Winchester's median sale price is $1,786,649 as of September 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.
Does it cost anything to use EffectiveAgents?
No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.
Do agents pay to be ranked or featured?
No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.
What commission do Winchester realtors charge?
Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.
Should I use a local Winchester agent or a national brand?
The individual agent matters more than the brand on the sign. Offices within the same national franchise vary widely in performance, and the agent you hire, not the logo, prices your home, negotiates your contract, and manages your closing. A strong local agent brings firsthand knowledge of Winchester neighborhoods, pricing patterns, and buyer activity. Compare agents on verified local results such as recent sales, days on market, and negotiation outcomes rather than name recognition.
What questions should I ask a Winchester realtor before hiring them?
Ask how many homes they have closed in Winchester in the past year, what their average sale-to-list ratio is, and how much of their business is in your neighborhood and price range. Ask how they will market your home or find you listings, and how often they will communicate. Strong agents answer with specifics. Verified transaction data is the fastest way to confirm what you hear.
Top Realtors by Zip Code in Winchester, MA
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