Top Realtors and Real Estate Agents in Winchester, TN
Rankings based on verified MLS transaction data. Last updated May 2026. No pay-to-play.
Top Agent
(40)
Charlie Gonzales
Southern Middle Realty powered By Keller Williams
7 Years of experience
41+ Sales in the last 12 months
Top 4.8%
in Winchester, TN
$56.6M
All-Time Sales
$230K - $1.3M
Price Range
4%
Negotiated Off List
Top Agent(19)
Darin Hasty
Hasty Realty, LLC
20 Years of experience
41+ Sales in the last 12 months
Top 7.2%
in Winchester, TN
$224.4M
All-Time Sales
$140K - $1.8M
Price Range
11%
Negotiated Off List
Top Agent(3)
Jeromey Crowell
RE/MAX 1st Realty
9 Years of experience
30+ Sales in the last 12 months
Top 9.6%
in Winchester, TN
$55.4M
All-Time Sales
$140K - $1.6M
Price Range
Top Agent(6)
Lynn Stubblefield
University Realty
37 Years of experience
4+ Sales in the last 12 months
Top 14%
in Winchester, TN
$32M
All-Time Sales
$170K - $730K
Price Range
Top Agent(6)
Teresa Smith
Century 21 Cumberland Realty
19 Years of experience
44+ Sales in the last 12 months
Top 15.2%
in Winchester, TN
$62.3M
All-Time Sales
$120K - $720K
Price Range
14%
Negotiated Off List
Top Agent(8)
Andrew Lamica
Lamica Realty
20 Years of experience
32+ Sales in the last 12 months
Top 17.2%
in Winchester, TN
$18.2M
All-Time Sales
$170K - $550K
Price Range
Top Agent(7)
John Cothran
Steve Coyhran Realty
23 Years of experience
39+ Sales in the last 12 months
$144.6M
All-Time Sales
$210K - $6.5M
Price Range
14%
Negotiated Off List
Top Agent(5)
Joe Garrett
Benchmark Realty
11 Years of experience
39+ Sales in the last 12 months
$122.9M
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
13+ Sales in the last 12 months
$32.1M
All-Time Sales
$150K - $970K
Price Range
7%
Negotiated Off List
(6)
Thomas Matthew Ore
Winton Auction & Realty Co
12 Years of experience
Top 0.8%
in Winchester, TN
241
Sold in Winchester, TN
4
Sold in last 18 months
(4)
Samuel D Hatfield
Sam Hatfield Realty Inc
25 Years of experience
Top 1.2%
in Winchester, TN
201
Sold in Winchester, TN
3
Sold in last 18 months
(1)
Chip Hayes
Retreat Properties Llc
22 Years of experience
Top 1.6%
in Winchester, TN
55
Sold in Winchester, TN
2004
Year Licensed
(3)
Lauren Bailey
Swafford\'s Property Shop
8 Years of experience
Top 2%
in Winchester, TN
51
Sold in Winchester, TN
2018
Year Licensed
(24)
Jennifer G Orr
Weichert Realtors Joe Orr & A
25 Years of experience
Top 2.4%
in Winchester, TN
50
Sold in Winchester, TN
2001
Year Licensed
Winchester Housing Market Trends
Median Sale Price
$585,000
+96.67% year-over-yearMedian Days on Market
130
+40 days year-over-yearSale-to-List Price
97.92%
-0.74% year-over-yearHomes Sold Above List Price
9.5%
-1.6% year-over-yearOff the Market in 2 Weeks
31.8%
+18.5% year-over-yearListings With Price Drops
29.0%
+7.9% year-over-yearMonths of Supply
6.6
Realtors in Winchester
250
Verified MLS market data through May 2026.
Do Top Winchester Agents Sell Faster?
The 9 top-ranked agents on EffectiveAgents in Winchester sell in a median of 27 days, compared with the Winchester market median of 130 days on market.
About 103 days faster (79% 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 June. To hit that window, plan to list around April.
Median days on market by month (shorter is faster)
June
Best month to sell
69 days
Typical time on market
98.7%
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.
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.
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: May 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 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 $585,000 as of May 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.
Top Realtors by Zip Code in Winchester, TN
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