Top Realtors and Real Estate Agents in Winchester, TN
Rankings based on verified MLS transaction data. Last updated August 2026. No pay-to-play.
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Top Agent
(41)
Charlie Gonzales
Southern Middle Realty powered By Keller Williams
7 Years of experience
42+ Sales in the last 12 months
Top 4.8%
in Winchester, TN
$60M
All-Time Sales
$240K - $1.3M
Price Range
4%
Negotiated Off List
Top Agent$226.9M
All-Time Sales
$140K - $1.8M
Price Range
11%
Negotiated Off List
Top Agent(33)
Vivian Fisher
Leading Edge Real Estate Group
11 Years of experience
23+ Sales in the last 12 months
Top 7.6%
in Winchester, TN
$71.3M
All-Time Sales
$150K - $1.4M
Price Range
6%
Negotiated Off List
Top AgentTop 9.2%
in Winchester, TN
$60.3M
All-Time Sales
$140K - $1.6M
Price Range
Top Agent$62.4M
All-Time Sales
$280K - $4.3M
Price Range
6
Sold in Winchester, TN
Top AgentTop 12.8%
in Winchester, TN
$40.4M
All-Time Sales
$190K - $810K
Price Range
Top Agent$589M
All-Time Sales
$390K - $6M
Price Range
3%
Negotiated Off List
Top Agent$148M
All-Time Sales
$270K - $1.6M
Price Range
4
Sold in Winchester, TN
Top Agent$45.1M
All-Time Sales
$180K - $1.2M
Price Range
6%
Negotiated Off List
Top Agent$158M
All-Time Sales
$140K - $1.1M
Price Range
8%
Negotiated Off List
Top Agent$32.1M
All-Time Sales
$170K - $730K
Price Range
3
Sold in Winchester, TN
Top Agent$64.9M
All-Time Sales
$130K - $720K
Price Range
14%
Negotiated Off List
Top Agent(33)
John Turner
Onward Real Estate | Turner Victory Team
26 Years of experience
94+ Sales in the last 12 months
Top 19.2%
in Winchester, TN
$114.3M
All-Time Sales
$340K - $1.1M
Price Range
Top AgentReviews not yet available
Benjamin Absher
Realty One Group Experts
4 Years of experience
33+ Sales in the last 12 months
Top 19.2%
in Winchester, TN
$21.6M
All-Time Sales
$190K - $620K
Price Range
Top AgentTop 19.2%
in Winchester, TN
$7.6M
All-Time Sales
$280K - $700K
Price Range
Top Agent$148M
All-Time Sales
$210K - $6.5M
Price Range
14%
Negotiated Off List
Top Agent$134.3M
All-Time Sales
$250K - $1.3M
Price Range
5%
Negotiated Off List
Top AgentReviews not yet available
Shelia Mittlesteadt
Haney Realty abd Property Management, LLC
12 Years of experience
15+ Sales in the last 12 months
$33.6M
All-Time Sales
$160K - $970K
Price Range
7%
Negotiated Off List
Winchester Housing Market Trends
Homes in Winchester take a median 101 days to sell, go for 96.46% of asking, prices are up 2.1% from a year ago. Verified MLS market data through August 2026.
Market temperature
Buyer's market
6.1 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$354,765
median sale price
How fast they sell
101 days
median time on market
Supply and competition
6.1 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 25 days, the Winchester market in 101
median sale price in Winchester
Do Top Winchester Agents Sell Faster?
The 18 top-ranked agents on EffectiveAgents in Winchester sell in a median of 25 days, compared with the Winchester market median of 101 days on market.
About 76 days faster (75% 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 May. To hit that window, plan to list around February.
Median days on market by month (shorter is faster)
May
Best month to sell
85 days
Typical time on market
96.9%
Of asking price
Seasonal averages from the last 24 months of Winchester, TN 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
Winchester's housing market currently reflects conditions that favor buyers more than the Housing Market Trends module above might suggest at first glance. With 6.1 months of supply and 128 active listings against 22 monthly sales, inventory sits near the balance point that typically signals neither an acute shortage nor a glut. The competitive indicators, however, tilt leverage toward purchasers. Only 3.2% of homes sold above asking, just 12.4% left the market within two weeks, and a substantial 37.3% of listings recorded a price reduction. That combination tells buyers that patience pays and that initial list prices are frequently negotiable.
The median sale price of $354,765 moved +2.1% year over year, while median days on market registered a +8 days change in market time, now sitting at 101 days. A sale-to-list ratio of 96.46% means sellers are generally accepting offers below their asking figure. For a buyer, this environment supports offers that account for the high price-drop share and the extended time listings sit unsold. For a seller, the data argues for disciplined, evidence-based pricing from day one rather than testing an aspirational number and correcting later.
Pricing correctly is where local expertise matters most. Winchester has 250 licensed agents, but performance varies widely across a market that saw 198 transactions analyzed over the past year. Identifying which agents consistently price and negotiate well, rather than choosing on name recognition alone, is the single decision that most affects your outcome in a market where 37.3% of listings eventually cut their price.
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 | $354,765 |
| Down payment (20%) | $70,953 |
| Loan amount | $283,812 |
| Monthly payment (PITI) | $2,580 |
Based on 28% debt-to-income ratio, 7.40% mortgage rate (as of October 8, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $354,765 median home price with 20% down at 7.40% (as of October 8, 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 billboard familiarity alone overlooks what actually drives results: a documented record of closings, pricing accuracy, and negotiation under real market conditions. In Winchester, where 37.3% of listings ultimately reduce their price and the sale-to-list ratio holds at 96.46%, an agent who can price correctly and hold a negotiation matters more than name recognition. Among the 250 licensed agents serving the area, EffectiveAgents has ranked 34 based on verified transaction data. The current top-ranked agent, Charlie Gonzales at Southern Middle Realty powered by Keller Williams, has closed 201 transactions with $59.0M in all-time sales volume across Winchester and the surrounding 37398 area. That transaction depth is meaningful in a market where only 3.2% of homes clear above list, since it reflects repeated experience structuring offers and counteroffers when leverage sits with buyers. The 41 reviews on record follow a consistent pattern emphasizing communication and realistic pricing guidance, both of which are the qualities the current data rewards most.
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.
250
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: August 2026
Winchester Real Estate Agent FAQs
Who is the best real estate agent in Winchester, TN?
The top-ranked agent in Winchester, TN is currently Charlie Gonzales at Southern Middle Realty powered by Keller Williams, with 201 closed transactions and $59.0M in all-time sales volume. EffectiveAgents identifies leading agents by analyzing verified performance data rather than advertising spend, reviewing 198 transactions across the market and ranking 34 of the area's 250 licensed agents. The best agent for you depends on your property type, price range, and timeline, so we recommend comparing several ranked professionals before deciding.
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 250 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 $354,765 as of August 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?
The median home in Winchester takes about 101 days to sell, and market time has seen a +8 days change year over year. Your actual timeline depends on pricing, condition, and location within the 37398 area. With 37.3% of listings recording price reductions and a sale-to-list ratio of 96.46%, homes priced accurately from the start tend to sell faster, while those that start high often sit and require cuts. Presentation, professional photography, and an experienced listing agent all measurably shorten the timeline.
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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