Top Realtors and Real Estate Agents in Winchester, VA
Rankings based on verified MLS transaction data. Last updated September 2026. No pay-to-play.
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Top Agent
Top 0.64%
in Winchester, VA
$359.9M
All-Time Sales
$230K - $4.2M
Price Range
6%
Negotiated Off List
Top AgentTop 0.96%
in Winchester, VA
$187.2M
All-Time Sales
$300K - $1.7M
Price Range
Top AgentTop 1.28%
in Winchester, VA
$192M
All-Time Sales
$280K - $1.4M
Price Range
5%
Negotiated Off List
Top AgentTop 1.92%
in Winchester, VA
$432.7M
All-Time Sales
$420K - $2.8M
Price Range
3%
Negotiated Off List
Top Agent
(49)
Renee Waymire
RE/MAX Roots | Capstone Realty Group
12 Years of experience
43+ Sales in the last 12 months
Top 2.88%
in Winchester, VA
$122.2M
All-Time Sales
$220K - $770K
Price Range
6%
Negotiated Off List
Top AgentTop 3.19%
in Winchester, VA
$264.8M
All-Time Sales
$290K - $60M
Price Range
Top AgentTop 3.83%
in Winchester, VA
$1.84B
All-Time Sales
$390K - $5.7M
Price Range
5%
Negotiated Off List
Top AgentTop 4.79%
in Winchester, VA
$175.3M
All-Time Sales
$200K - $1.5M
Price Range
9%
Negotiated Off List
Top AgentTop 7.35%
in Winchester, VA
$47.7M
All-Time Sales
$230K - $730K
Price Range
3%
Negotiated Off List
Top AgentTop 8.63%
in Winchester, VA
$682.8M
All-Time Sales
$320K - $2M
Price Range
5%
Negotiated Off List
Top AgentTop 8.95%
in Winchester, VA
$338.4M
All-Time Sales
$420K - $2.2M
Price Range
4%
Negotiated Off List
Top Agent$253.7M
All-Time Sales
$240K - $18M
Price Range
6%
Negotiated Off List
Top Agent$32M
All-Time Sales
$200K - $830K
Price Range
22
Sold in Winchester, VA
Top AgentTop 13.1%
in Winchester, VA
$69.8M
All-Time Sales
$200K - $810K
Price Range
5%
Negotiated Off List
Top Agent(19)
Rex Petrey
Keller Williams Leesburg Winchester
4 Years of experience
37+ Sales in the last 12 months
Top 15.02%
in Winchester, VA
$59.4M
All-Time Sales
$360K - $3.3M
Price Range
Top AgentTop 15.34%
in Winchester, VA
$280M
All-Time Sales
$300K - $1.2M
Price Range
Top Agent(925)
Jason Cheperdak
Samson Properties - Shepherd Homes Group
10 Years of experience
1,019+ Sales in the last 12 months
Top 15.97%
in Winchester, VA
$1.9B
All-Time Sales
$510K - $3M
Price Range
4%
Negotiated Off List
Top Agent$119M
All-Time Sales
$330K - $2.8M
Price Range
9%
Negotiated Off List
Top AgentTop 18.21%
in Winchester, VA
$1.05B
All-Time Sales
$460K - $5M
Price Range
Top Agent$71.3M
All-Time Sales
$430K - $2.5M
Price Range
17%
Negotiated Off List
Top Agent$533.8M
All-Time Sales
$390K - $3.4M
Price Range
3%
Negotiated Off List
Top Agent$1.04B
All-Time Sales
$310K - $3.4M
Price Range
4%
Negotiated Off List
Top Agent$1.14B
All-Time Sales
$270K - $9.2M
Price Range
8%
Negotiated Off List
Top Agent(107)
Tanya Johnson
Keller Williams Realty - Tanya & Co.
29 Years of experience
82+ Sales in the last 12 months
$731.6M
All-Time Sales
$430K - $2.5M
Price Range
3%
Negotiated Off List
Top Agent$956.2M
All-Time Sales
$470K - $2.8M
Price Range
4%
Negotiated Off List
Winchester Housing Market Trends
Homes in Winchester take a median 64 days to sell, go for 97.83% of asking, prices are down 4.5% from a year ago. Verified MLS market data through September 2026.
Market temperature
Balanced market
4.1 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$372,323
median sale price
How fast they sell
64 days
median time on market
Supply and competition
4.1 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 23 days, the Winchester market in 64
median sale price in Winchester
Do Top Winchester Agents Sell Faster?
The 25 top-ranked agents on EffectiveAgents in Winchester sell in a median of 23 days, compared with the Winchester market median of 64 days on market.
About 41 days faster (64% 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
41 days
Typical time on market
99.1%
Of asking price
Seasonal averages from the last 24 months of Winchester, VA sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
What These Numbers Mean for Winchester Buyers and Sellers
The Housing Market Trends module above records a median sale price of $372,323 at $210.63 per square foot, with the median sale price moving -4.5% over the past year. Reading the competitive indicators together clarifies where leverage now sits in Winchester. With 4.1 months of supply, 115 active listings against 29 homes sold and 91 pending sales in the latest month, the market reads as roughly balanced rather than tilted decisively toward either side.
Several signals point toward more room for buyers to negotiate. Only 12.9% of homes closed above list price, 32.7% of active listings carried a price reduction, and the median time to a contract reached 64 days, a +16 days change in market time. That combination means buyers can reasonably ask for concessions, request repairs, and avoid escalation on all but the sharpest listings. At the same time, 26.4% of homes left the market within two weeks, so correctly priced, move-in-ready properties still transact quickly.
For sellers, the takeaway is disciplined pricing. With a sale-to-list ratio of 97.83% and roughly a third of listings cutting price, homes launched above the comparable range tend to sit and then discount, which erodes the final number more than an accurate initial list would. Across 264 licensed agents in the four Winchester zip codes, the difference between a data-guided pricing strategy and a hopeful one is measurable in both days on market and dollars.
What Winchester Home Prices Mean for You
Understanding the true cost of homeownership in Winchester goes beyond the listing price. These calculators break down what today's market conditions mean for your budget, your timeline, and your negotiating position.
| Median home price | $372,323 |
| Down payment (20%) | $74,465 |
| Loan amount | $297,858 |
| Monthly payment (PITI) | $2,650 |
Based on 28% debt-to-income ratio, 7.18% mortgage rate (as of November 5, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $372,323 median home price with 20% down at 7.18% (as of November 5, 2026) for 30 years. Property tax estimated at 1.15% of home value.
Year-over-year data reflects the most recent rolling period from Winchester MLS records. Prior year values calculated from current figures and published YoY changes.
What to Look for in a Winchester Realtor
Choosing an agent on name recognition or a familiar yard sign overlooks what actually moves a transaction: a documented record across many closings and neighborhoods. EffectiveAgents ranks 101 of Winchester's agents using 321 analyzed transactions, so the comparison rests on verified outcomes rather than advertising spend. Traci Shoberg at Shoberg Real Estate, Inc. illustrates the pattern, with 1,227 career transactions, 68 client reviews, and $357.5M in all-time sales volume. That volume matters in negotiation: an agent who has priced and closed repeatedly across the 22601, 22602, and 22603 zip codes reads a 12.9% above-list share and a 32.7% price-drop rate accurately, then structures offers or counteroffers accordingly. When reviewing candidates, look past a single glowing testimonial and study the pattern: consistent review counts over time, feedback that references pricing accuracy and communication, and results across a range of property types rather than a handful of standout sales.
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.
264
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
Who is the best real estate agent in Winchester, VA?
Traci Shoberg at Shoberg Real Estate, Inc. ranks as the top agent in Winchester, VA, based on EffectiveAgents' analysis, with 1,227 career transactions, 68 reviews, and $357.5M in all-time sales volume. EffectiveAgents evaluates 321 local transactions and measures agents on verified closings, sale-to-list performance, and review consistency rather than advertising. Because 'best' depends on your price point and timeline, we recommend comparing two or three ranked agents from the 101 qualifying professionals before signing.
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 264 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 $372,323 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.
How long does it take to sell a house in Winchester?
In Winchester, the median home currently takes 64 days to go under contract, a +16 days change from last year's 48. Actual timing varies with price accuracy, condition, and location across the 22601, 22602, 22603, and 22604 zip codes. Roughly 26.4% of homes leave the market within two weeks, so well-priced, move-in-ready listings still sell fast, while homes priced above comparable sales tend to join the 32.7% of listings that reduce price and stay on the market longer.
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.
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