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Updated October 1, 2026
If you’re buying or selling a home, choosing the right real estate agent can make a big difference in your experience and outcome. Top real estate agents in Winchester, Virginia close more deals, negotiate better prices, and move homes faster than their peers.
We analyzed transactions and performance metrics for 313 real estate agents in Winchester, VA to identify the best of the best. These are the top selling realtors in Winchester based on local experience, sales history, and overall results.
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Our team spends hundreds of hours each month analyzing real estate agents across the country so you don’t have to. We focus on the most important data for typical buyers and sellers in Winchester — people looking for a knowledgeable, well-rounded agent who can deliver strong results.
To identify the best agents for most people, we apply a consistent set of filters to narrow the field to agents with relevant experience, strong performance in the local market, and a balanced track record. We then sort those agents based on key metrics like sales volume, speed, pricing accuracy, and client mix.
We regularly update our rankings as new data becomes available and continue refining our approach to surface the most useful recommendations. See our full methodology.
Winchester, VA top real estate agents (October 2026 rankings)
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Highly rated
Top 1% local
Neighborhood expert
Repeat clients
Luxury homes
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Daniel J Whitacre is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 70 transactions over the past 12 months — 143 in the past two years. Daniel J Whitacre's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 65% sellers, 35% buyers
Total recent sales: 143
Local ranking by total sales: #2
State ranking by total sales: #46
Median days on market: 53 days
Median sale-to-list ratio: 100%
License #: 0225212949, WVA230040227 (VA, WV)
Are you Daniel J Whitacre? Fill out this form to claim your profile or offer a correction.
Highly rated
Top 1% local
Listing specialist
Neighborhood expert
Repeat clients
Luxury homes
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Sheila R Pack is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 63 transactions over the past 12 months — 154 in the past two years. Sheila R Pack's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 73% sellers, 27% buyers
Total recent sales: 154
Local ranking by total sales: #1
State ranking by total sales: #43
Median days on market: 56 days
Median sale-to-list ratio: 100%
License #: 0225075316 (VA)
Are you Sheila R Pack? Fill out this form to claim your profile or offer a correction.
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Leslie A Webb is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 49 transactions over the past 12 months — 97 in the past two years. Leslie A Webb's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 45% sellers, 55% buyers
Total recent sales: 97
Local ranking by total sales: #11
State ranking by total sales: #513
Median days on market: 62 days
Median sale-to-list ratio: 100%
License #: SP0003165, WVS190300602 (VA, WV)
Are you Leslie A Webb? Fill out this form to claim your profile or offer a correction.
Shane Bowman
RE/MAX Roots
Recent sales*
14
Local sales*
11
Price range*
$162K - $675K
Typical price*
$360,000
Highlights
About
20+ years experience
Repeat clients
First-time buyers
Single-family homes
Townhouses
Shane Bowman is a real estate agent who is primarily active in Winchester, VA. Shane Bowman has worked in real estate for over 25 years. They work with sellers and buyers and have closed at least 7 transactions over the past 12 months — 14 in the past two years. Shane Bowman's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Est. years experience: 25
Works with: 36% sellers, 64% buyers
Total recent sales: 14
Local ranking by total sales: #136
State ranking by total sales: #5,075
Median days on market: 67 days
Median sale-to-list ratio: 101%
License #: 0225244707 (VA, WV)
Office address: Winchester, VA 22601, USA
Are you Shane Bowman? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Bradley Comstock
ERA Oakcrest Realty, Inc.
Recent sales*
96
Local sales*
62
Price range*
$180K - $1.1M
Typical price*
$412,750
Highlights
About
Top 1% local
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Bradley Comstock is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 51 transactions over the past 12 months — 96 in the past two years. Bradley Comstock's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 96
Local ranking by total sales: #3
State ranking by total sales: #316
Median days on market: 54 days
Median sale-to-list ratio: 100%
License #: 0225220037, WVS180300331 (VA, WV)
Are you Bradley Comstock? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Keenan L Shanholtz
WEST VIRGINIA LAND & HOME REALTY
Recent sales*
58
Local sales*
49
Price range*
$40K - $1.5M
Typical price*
$407,500
Highlights
About
Highly rated
Top 5% localFast sales
Neighborhood expert
Repeat clients
Luxury homes
First-time buyers
Single-family homes
Manufactured homes
Keenan L Shanholtz is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 58 in the past two years. Keenan L Shanholtz's experience includes luxury homes and first-time homebuyers.
Works with: 60% sellers, 40% buyers
Total recent sales: 58
Local ranking by total sales: #10
State ranking by total sales: #553
Median days on market: 47 days
Median sale-to-list ratio: 100%
Are you Keenan L Shanholtz? Fill out this form to claim your profile or offer a correction.
Highly rated
Top 1% local
Offer strategy
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Multi-family homes
Roxanna D Grimes is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 61 transactions over the past 12 months — 102 in the past two years. Roxanna D Grimes's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Works with: 60% sellers, 40% buyers
Total recent sales: 102
Local ranking by total sales: #5
State ranking by total sales: #382
Median days on market: 54 days
Median sale-to-list ratio: 100%
License #: 0225066370 (VA, WV)
Are you Roxanna D Grimes? Fill out this form to claim your profile or offer a correction.
Mark S Francis
ICON Real Estate, LLC
Recent sales*
40
Local sales*
33
Price range*
$207K - $1.2M
Typical price*
$401,750
Highlights
About
Top 10% local
Offer strategy
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Mark S Francis is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 17 transactions over the past 12 months — 40 in the past two years. Mark S Francis's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 48% sellers, 53% buyers
Total recent sales: 40
Local ranking by total sales: #24
State ranking by total sales: #1,277
Median days on market: 72 days
Median sale-to-list ratio: 99%
License #: 0225069635, WVA250040374 (VA, WV)
Are you Mark S Francis? Fill out this form to claim your profile or offer a correction.
Top 5% local
Neighborhood expert
First-time buyers
Single-family homes
Jeanne Mezzatesta is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 19 transactions over the past 12 months — 41 in the past two years. Jeanne Mezzatesta's experience includes luxury homes and first-time homebuyers.
Works with: 54% sellers, 46% buyers
Total recent sales: 41
Local ranking by total sales: #18
State ranking by total sales: #1,069
Median days on market: 67 days
Median sale-to-list ratio: 100%
License #: 0225251371 (VA, WV)
Are you Jeanne Mezzatesta? Fill out this form to claim your profile or offer a correction.
Julie M Teets
ERA Oakcrest Realty, Inc.
Recent sales*
48
Local sales*
35
Price range*
$223K - $1.3M
Typical price*
$425,000
Highlights
About
Top 10% local
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Julie M Teets is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 48 in the past two years. Julie M Teets's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 52% sellers, 48% buyers
Total recent sales: 48
Local ranking by total sales: #19
State ranking by total sales: #1,140
Median days on market: 50 days
Median sale-to-list ratio: 100%
License #: 0225105327 (VA)
Are you Julie M Teets? Fill out this form to claim your profile or offer a correction.
Highly rated
Top 1% localFast sales
Listing specialist
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Vacant land
Lisa M Cox is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 38 transactions over the past 12 months — 75 in the past two years. Lisa M Cox's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Works with: 71% sellers, 29% buyers
Total recent sales: 75
Local ranking by total sales: #4
State ranking by total sales: #392
Median days on market: 47 days
Median sale-to-list ratio: 100%
License #: 0225194183 (VA)
Are you Lisa M Cox? Fill out this form to claim your profile or offer a correction.
Highly rated
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Leah R Clowser is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 45 transactions over the past 12 months — 99 in the past two years. Leah R Clowser's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 61% sellers, 39% buyers
Total recent sales: 99
Local ranking by total sales: #9
State ranking by total sales: #493
Median days on market: 53 days
Median sale-to-list ratio: 100%
License #: 0225048720 (VA, WV)
Are you Leah R Clowser? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Tiffany J Hunter
ERA Oakcrest Realty, Inc.
Recent sales*
36
Local sales*
35
Price range*
$206K - $750K
Typical price*
$450,000
Highlights
About
Top 10% local
Offer strategy
Neighborhood expert
First-time buyers
Single-family homes
Townhouses
Tiffany J Hunter is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 18 transactions over the past 12 months — 36 in the past two years. Tiffany J Hunter's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 58% sellers, 42% buyers
Total recent sales: 36
Local ranking by total sales: #20
State ranking by total sales: #1,166
Median days on market: 57 days
Median sale-to-list ratio: 100%
License #: 0225090483 (VA)
Are you Tiffany J Hunter? Fill out this form to claim your profile or offer a correction.
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Manufactured homes
Kelly R Dodd is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 54 in the past two years. Kelly R Dodd's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 54% sellers, 46% buyers
Total recent sales: 54
Local ranking by total sales: #13
State ranking by total sales: #749
Median days on market: 69 days
Median sale-to-list ratio: 100%
License #: WV0022580 (WV)
Are you Kelly R Dodd? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Teresa L Strohmeyer
ERA Oakcrest Realty, Inc.
Recent sales*
55
Local sales*
39
Price range*
$77K - $935K
Typical price*
$332,000
Highlights
About
Top 5% localFast sales
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Teresa L Strohmeyer is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 26 transactions over the past 12 months — 55 in the past two years. Teresa L Strohmeyer's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 58% sellers, 42% buyers
Total recent sales: 55
Local ranking by total sales: #16
State ranking by total sales: #943
Median days on market: 54 days
Median sale-to-list ratio: 100%
License #: 0225026152, WV0021378 (VA, WV)
Are you Teresa L Strohmeyer? Fill out this form to claim your profile or offer a correction.
Christopher W Roszko
Colony Realty
Recent sales*
50
Local sales*
33
Price range*
$110K - $1.1M
Typical price*
$325,000
Highlights
About
Top 10% localFast sales
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Christopher W Roszko is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 50 in the past two years. Christopher W Roszko's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 50
Local ranking by total sales: #23
State ranking by total sales: #1,183
Median days on market: 37 days
Median sale-to-list ratio: 100%
License #: 0225258235, WVS230302703 (VA, WV)
Are you Christopher W Roszko? Fill out this form to claim your profile or offer a correction.
James W King Jr
Re/Max Roots
Recent sales*
32
Local sales*
24
Price range*
$212K - $1.2M
Typical price*
$457,500
Highlights
About
First-time buyers
Single-family homes
Townhouses
James W King Jr is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 17 transactions over the past 12 months — 32 in the past two years. James W King Jr's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Works with: 53% sellers, 47% buyers
Total recent sales: 32
Local ranking by total sales: #44
State ranking by total sales: #2,114
Median days on market: 52 days
Median sale-to-list ratio: 100%
License #: 0225065135 (VA, WV)
Are you James W King Jr? Fill out this form to claim your profile or offer a correction.
Lori Fountain Bales
Keller Williams Realty
Recent sales*
45
Local sales*
32
Price range*
$250K - $1.4M
Typical price*
$475,000
Highlights
About
Top 10% localFast sales
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Manufactured homes
Lori Fountain Bales is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 45 in the past two years. Lori Fountain Bales's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 44% sellers, 56% buyers
Total recent sales: 45
Local ranking by total sales: #26
State ranking by total sales: #1,274
Median days on market: 43 days
Median sale-to-list ratio: 98%
License #: 0225229904, 200301291 (VA, WV)
Are you Lori Fountain Bales? Fill out this form to claim your profile or offer a correction.
Amanda M Downs
Samson Properties
Recent sales*
37
Local sales*
8
Price range*
$150K - $749K
Typical price*
$385,000
Highlights
About
Listing specialist
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Amanda M Downs is a real estate agent who is primarily active in Harrisonburg, VA. They work with sellers and buyers and have closed at least 15 transactions over the past 12 months — 37 in the past two years. Amanda M Downs's experience includes first-time homebuyers and VA loans and military buyers.
Works with: 76% sellers, 24% buyers
Total recent sales: 37
Local ranking by total sales: #172
State ranking by total sales: #2,077
Median days on market: 70 days
Median sale-to-list ratio: 100%
License #: 0225204780 (MD, VA)
Are you Amanda M Downs? Fill out this form to claim your profile or offer a correction.
Kristi D Cooper
Realty ONE Group Old Towne
Recent sales*
17
Local sales*
16
Price range*
$120K - $825K
Typical price*
$365,000
Highlights
About
Repeat clients
HOA experience
Single-family homes
Manufactured homes
Kristi D Cooper is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 1 transaction over the past 12 months — 17 in the past two years. Kristi D Cooper's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 47% sellers, 53% buyers
Total recent sales: 17
Local ranking by total sales: #80
State ranking by total sales: #3,516
Median days on market: 52 days
Median sale-to-list ratio: 97%
License #: 0225232654 (VA, WV)
Are you Kristi D Cooper? Fill out this form to claim your profile or offer a correction.
Michele L Gibson
Samson Properties
Recent sales*
49
Local sales*
23
Price range*
$253K - $1.4M
Typical price*
$499,000
Highlights
About
Highly rated
Neighborhood expert
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Michele L Gibson is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 23 transactions over the past 12 months — 49 in the past two years. Michele L Gibson's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Works with: 55% sellers, 45% buyers
Total recent sales: 49
Local ranking by total sales: #48
State ranking by total sales: #2,296
Median days on market: 71 days
Median sale-to-list ratio: 99%
License #: 0225059345, WV0027433 (VA, WV)
Office address: Berryville, VA 22611, USA
Are you Michele L Gibson? Fill out this form to claim your profile or offer a correction.
Tracie Clawson
ERA Oakcrest Realty, Inc.
Recent sales*
27
Local sales*
23
Price range*
$330K - $720K
Typical price*
$470,000
Highlights
About
Repeat clients
HOA experience
Single-family homes
Tracie Clawson is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 16 transactions over the past 12 months — 27 in the past two years. Tracie Clawson is experienced with sales involving HOAs.
Works with: 56% sellers, 44% buyers
Total recent sales: 27
Local ranking by total sales: #49
State ranking by total sales: #2,335
Median days on market: 63 days
Median sale-to-list ratio: 100%
License #: 0225211653 (VA)
Are you Tracie Clawson? Fill out this form to claim your profile or offer a correction.
George C Johnson Jr
Jim Barb Realty Inc.
Recent sales*
19
Local sales*
16
Price range*
$160K - $1.1M
Typical price*
$397,500
Highlights
About
Fast sales
Repeat clients
First-time buyers
Single-family homes
Townhouses
George C Johnson Jr is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 14 transactions over the past 12 months — 19 in the past two years. George C Johnson Jr's experience includes first-time homebuyers and luxury homes.
Works with: 47% sellers, 53% buyers
Total recent sales: 19
Local ranking by total sales: #79
State ranking by total sales: #3,457
Median days on market: 47 days
Median sale-to-list ratio: 99%
License #: 0225042189, WV0019360 (VA, WV)
Are you George C Johnson Jr? Fill out this form to claim your profile or offer a correction.
Kaitlyn Behr
Samson Properties
Recent sales*
43
Local sales*
31
Price range*
$180K - $810K
Typical price*
$415,000
Highlights
About
Top 10% localFast sales
Neighborhood expert
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Kaitlyn Behr is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 25 transactions over the past 12 months — 43 in the past two years. Kaitlyn Behr's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 65% sellers, 35% buyers
Total recent sales: 43
Local ranking by total sales: #28
State ranking by total sales: #1,427
Median days on market: 52 days
Median sale-to-list ratio: 100%
License #: 0225231690 (VA)
Are you Kaitlyn Behr? Fill out this form to claim your profile or offer a correction.
Heloisa P Amar
Samson Properties
Recent sales*
46
Local sales*
34
Price range*
$225K - $465K
Typical price*
$321,250
Highlights
About
Top 10% local
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Commercial properties
Heloisa P Amar is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 46 in the past two years. Heloisa P Amar's experience includes first-time homebuyers and sales involving HOAs.
Works with: 43% sellers, 57% buyers
Total recent sales: 46
Local ranking by total sales: #21
State ranking by total sales: #1,192
Median days on market: 91 days
Median sale-to-list ratio: 100%
License #: 0225215211 (VA, WV)
Are you Heloisa P Amar? Fill out this form to claim your profile or offer a correction.
Highly rated
Top 5% local
Offer strategy
Listing specialist
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Multi-family homes
David K Spence is a real estate agent who is primarily active in Winchester, VA. They primarily work with sellers and have closed at least 38 transactions over the past 12 months — 76 in the past two years. David K Spence's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 84% sellers, 16% buyers
Total recent sales: 76
Local ranking by total sales: #8
State ranking by total sales: #461
Median days on market: 71 days
Median sale-to-list ratio: 99%
License #: 0225071088 (VA, WV)
Are you David K Spence? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Laura D White
ERA Oakcrest Realty, Inc.
Recent sales*
49
Local sales*
44
Price range*
$250K - $1.3M
Typical price*
$469,000
Highlights
About
Top 5% localFast sales
Neighborhood expert
Repeat clients
HOA experience
Senior living
Single-family homes
Townhouses
Laura D White is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 49 in the past two years. Laura D White's experience includes sales involving HOAs, luxury homes, and properties in senior communities.
Works with: 69% sellers, 31% buyers
Total recent sales: 49
Local ranking by total sales: #12
State ranking by total sales: #727
Median days on market: 44 days
Median sale-to-list ratio: 100%
License #: 0225087046 (VA)
Are you Laura D White? Fill out this form to claim your profile or offer a correction.
Paul J Gallagher Jr
Colony Realty
Recent sales*
48
Local sales*
30
Price range*
$120K - $1.1M
Typical price*
$499,900
Highlights
About
Top 10% localFast sales
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Manufactured homes
Paul J Gallagher Jr is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 48 in the past two years. Paul J Gallagher Jr's experience includes sales involving HOAs, properties in senior communities, and luxury homes.
Works with: 52% sellers, 48% buyers
Total recent sales: 48
Local ranking by total sales: #30
State ranking by total sales: #1,447
Median days on market: 44 days
Median sale-to-list ratio: 100%
License #: 0225211142 (VA)
Are you Paul J Gallagher Jr? Fill out this form to claim your profile or offer a correction.
Stephanie Ryall
Realty ONE Group Old Towne
Recent sales*
39
Local sales*
28
Price range*
$150K - $759K
Typical price*
$359,641
Highlights
About
Top 10% local
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Stephanie Ryall is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 26 transactions over the past 12 months — 39 in the past two years. Stephanie Ryall's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 36% sellers, 64% buyers
Total recent sales: 39
Local ranking by total sales: #32
State ranking by total sales: #1,714
Median days on market: 60 days
Median sale-to-list ratio: 100%
License #: 0225214221 (VA)
Are you Stephanie Ryall? Fill out this form to claim your profile or offer a correction.
Cynthia K Greenya
Keller Williams Realty
Recent sales*
37
Local sales*
15
Price range*
$97K - $1.4M
Typical price*
$445,000
Highlights
About
Negotiation expert
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Cynthia K Greenya is a real estate agent who is primarily active in Washington DC, DC. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 37 in the past two years. Cynthia K Greenya's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 59% sellers, 41% buyers
Total recent sales: 37
Local ranking by total sales: #83
State ranking by total sales: #3,665
Median days on market: 52 days
Median sale-to-list ratio: 100%
License #: 0225056537 (VA)
Are you Cynthia K Greenya? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Traci J Shoberg
Samson Properties
Recent sales*
69
Local sales*
52
Price range*
$196K - $1.2M
Typical price*
$420,000
Highlights
About
Highly rated
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Traci J Shoberg is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 39 transactions over the past 12 months — 69 in the past two years. Traci J Shoberg's experience includes luxury homes, sales involving HOAs, and first-time homebuyers.
Works with: 68% sellers, 32% buyers
Total recent sales: 69
Local ranking by total sales: #7
State ranking by total sales: #501
Median days on market: 79 days
Median sale-to-list ratio: 99%
License #: 225055206, WVA230040257 (VA, WV)
Are you Traci J Shoberg? Fill out this form to claim your profile or offer a correction.
Kerry Elizabeth Wysong
Long & Foster Real Estate, Inc.
Recent sales*
14
Local sales*
11
Price range*
$190K - $870K
Typical price*
$417,995
Highlights
About
HOA experience
Single-family homes
Townhouses
Kerry Elizabeth Wysong is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 9 transactions over the past 12 months — 14 in the past two years. Kerry Elizabeth Wysong's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Works with: 43% sellers, 57% buyers
Total recent sales: 14
Local ranking by total sales: #129
State ranking by total sales: #4,968
Median days on market: 52 days
Median sale-to-list ratio: 95.5%
License #: 0225256259, WVS230303034 (VA, WV)
Are you Kerry Elizabeth Wysong? Fill out this form to claim your profile or offer a correction.
Leo J Smith
CENTURY 21 New Millennium
Recent sales*
16
Local sales*
12
Price range*
$155K - $900K
Typical price*
$335,000
Highlights
About
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Leo J Smith is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 8 transactions over the past 12 months — 16 in the past two years. Leo J Smith's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 16
Local ranking by total sales: #117
State ranking by total sales: #4,639
Median days on market: 85 days
Median sale-to-list ratio: 99%
License #: 0225064100 (VA)
Are you Leo J Smith? Fill out this form to claim your profile or offer a correction.
Jodi Costello
ERA Oakcrest Realty, Inc.
Recent sales*
25
Local sales*
17
Price range*
$140K - $530K
Typical price*
$322,000
Highlights
About
Highly ratedFast sales
Offer strategy
HOA experience
First-time buyers
Single-family homes
Townhouses
Jodi Costello is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 12 transactions over the past 12 months — 25 in the past two years. Jodi Costello's experience includes first-time homebuyers and sales involving HOAs.
Works with: 44% sellers, 56% buyers
Total recent sales: 25
Local ranking by total sales: #71
State ranking by total sales: #3,262
Median days on market: 43 days
Median sale-to-list ratio: 100%
License #: 0225201680 (VA, WV)
Are you Jodi Costello? Fill out this form to claim your profile or offer a correction.
Erika D De Azagra
ERA Oakcrest Realty, Inc.
Recent sales*
20
Local sales*
17
Price range*
$280K - $1.4M
Typical price*
$452,000
Highlights
About
Single-family homes
Townhouses
Erika D De Azagra is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 9 transactions over the past 12 months — 20 in the past two years. Erika D De Azagra's experience includes luxury homes, sales involving HOAs, and first-time homebuyers.
Works with: 55% sellers, 45% buyers
Total recent sales: 20
Local ranking by total sales: #70
State ranking by total sales: #3,232
Median days on market: 55 days
Median sale-to-list ratio: 100%
License #: 0225081741 (VA, WV)
Are you Erika D De Azagra? Fill out this form to claim your profile or offer a correction.
Jeffrey M Webber
Long & Foster Real Estate, Inc.
Local sales*
11
Price range*
$350K - $585K
Typical price*
$387,000
Highlights
About
Repeat clients
Senior living
Single-family homes
Jeffrey M Webber is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 3 transactions over the past 12 months — 11 in the past two years. Jeffrey M Webber's experience includes properties in senior communities and sales involving HOAs.
Works with: 55% sellers, 45% buyers
Total recent sales: 11
Local ranking by total sales: #126
State ranking by total sales: #4,917
Median days on market: 57 days
Median sale-to-list ratio: 98.5%
License #: 225002434 (VA)
Are you Jeffrey M Webber? Fill out this form to claim your profile or offer a correction.
Nicole Panos Lewis
Coldwell Banker Premier
Recent sales*
36
Local sales*
18
Price range*
$160K - $765K
Typical price*
$355,000
Highlights
About
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Nicole Panos Lewis is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 36 in the past two years. Nicole Panos Lewis's experience includes first-time homebuyers and VA loans and military buyers.
Works with: 39% sellers, 61% buyers
Total recent sales: 36
Local ranking by total sales: #66
State ranking by total sales: #3,116
Median days on market: 105 days
Median sale-to-list ratio: 100%
License #: 0225242688, WVS200301227 (VA, WV)
Are you Nicole Panos Lewis? Fill out this form to claim your profile or offer a correction.
Rhonda Shade
ERA Oakcrest Realty, Inc.
Recent sales*
45
Local sales*
14
Price range*
$185K - $839K
Typical price*
$369,000
Highlights
About
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Rhonda Shade is a real estate agent who is primarily active in Hagerstown, MD. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 45 in the past two years. Rhonda Shade's experience includes VA loans and military buyers, first-time homebuyers, and sales involving HOAs.
Works with: 38% sellers, 62% buyers
Total recent sales: 45
Local ranking by total sales: #96
State ranking by total sales: #4,073
Median days on market: 75 days
Median sale-to-list ratio: 98%
License #: 0225241981 (VA, WV)
Are you Rhonda Shade? Fill out this form to claim your profile or offer a correction.
Barton Thomas Chasler
Realty ONE Group Old Towne
Recent sales*
16
Local sales*
15
Price range*
$226K - $775K
Typical price*
$351,500
Highlights
About
Fast sales
Offer strategy
Single-family homes
Townhouses
Barton Thomas Chasler is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 10 transactions over the past 12 months — 16 in the past two years.
Works with: 50% sellers, 50% buyers
Total recent sales: 16
Local ranking by total sales: #82
State ranking by total sales: #3,641
Median days on market: 52 days
Median sale-to-list ratio: 96.5%
License #: 0225274184 (VA)
Are you Barton Thomas Chasler? Fill out this form to claim your profile or offer a correction.
Phyllis Guthrie
Keller Williams Realty
Recent sales*
44
Local sales*
17
Price range*
$145K - $1.8M
Typical price*
$380,250
Highlights
About
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Phyllis Guthrie is a real estate agent who is primarily active in Hagerstown, MD. They work with sellers and buyers and have closed at least 27 transactions over the past 12 months — 44 in the past two years. Phyllis Guthrie's experience includes first-time homebuyers, VA loans and military buyers, and sales involving HOAs.
Works with: 36% sellers, 64% buyers
Total recent sales: 44
Local ranking by total sales: #74
State ranking by total sales: #3,327
Median days on market: 62 days
Median sale-to-list ratio: 100%
License #: 0225223168, WV0030618 (VA, WV)
Are you Phyllis Guthrie? Fill out this form to claim your profile or offer a correction.
Katherine Landi Jordan
Samson Properties
Recent sales*
26
Local sales*
17
Price range*
$212K - $902K
Typical price*
$387,450
Highlights
About
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Katherine Landi Jordan is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 14 transactions over the past 12 months — 26 in the past two years. Katherine Landi Jordan's experience includes sales involving HOAs, first-time homebuyers, and properties in senior communities.
Works with: 58% sellers, 42% buyers
Total recent sales: 26
Local ranking by total sales: #72
State ranking by total sales: #3,271
Median days on market: 59 days
Median sale-to-list ratio: 100%
License #: 0225249626 (VA, WV)
Are you Katherine Landi Jordan? Fill out this form to claim your profile or offer a correction.
Julie D Shiley
Coldwell Banker Realty
Recent sales*
37
Local sales*
12
Price range*
$215K - $1M
Typical price*
$420,000
Highlights
About
Fast sales
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Condos
Julie D Shiley is a real estate agent who is primarily active in Hagerstown, MD. They work with sellers and buyers and have closed at least 13 transactions over the past 12 months — 37 in the past two years. Julie D Shiley's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 54% sellers, 46% buyers
Total recent sales: 37
Local ranking by total sales: #115
State ranking by total sales: #4,269
Median days on market: 212 days
Median sale-to-list ratio: 99%
License #: 0225220202, WVS200300948 (VA, WV)
Are you Julie D Shiley? Fill out this form to claim your profile or offer a correction.
Karl Achstetter
Keller Williams Realty
Recent sales*
14
Local sales*
6
Price range*
$140K - $2M
Typical price*
$488,450
Highlights
About
Listing specialist
Repeat clients
Single-family homes
Condos
Townhouses
Commercial properties
Karl Achstetter is a real estate agent who is primarily active in Washington DC, DC. They work with sellers and buyers and have closed at least 11 transactions over the past 12 months — 14 in the past two years. Karl Achstetter's experience includes luxury homes and first-time homebuyers.
Works with: 71% sellers, 29% buyers
Total recent sales: 14
Local ranking by total sales: #235
State ranking by total sales: #7,528
Median days on market: 70 days
Median sale-to-list ratio: 100%
License #: 225241340 (VA)
Are you Karl Achstetter? Fill out this form to claim your profile or offer a correction.
Jen Richards
Samson Properties
Recent sales*
30
Local sales*
18
Price range*
$195K - $660K
Typical price*
$369,500
Highlights
About
HOA experience
Military buyers
Single-family homes
Townhouses
Condos
Jen Richards is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 15 transactions over the past 12 months — 30 in the past two years. Jen Richards's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Works with: 47% sellers, 53% buyers
Total recent sales: 30
Local ranking by total sales: #63
State ranking by total sales: #3,066
Median days on market: 52 days
Median sale-to-list ratio: 100%
License #: 0225237249, WVS230302474 (VA, WV)
Are you Jen Richards? Fill out this form to claim your profile or offer a correction.
Brett A Sowder
RE/MAX Roots
Recent sales*
60
Local sales*
25
Price range*
$230K - $1.3M
Typical price*
$388,131
Highlights
About
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Brett A Sowder is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 29 transactions over the past 12 months — 60 in the past two years. Brett A Sowder's experience includes luxury homes, first-time homebuyers, and properties in senior communities.
Works with: 58% sellers, 42% buyers
Total recent sales: 60
Local ranking by total sales: #40
State ranking by total sales: #1,856
Median days on market: 80 days
Median sale-to-list ratio: 100%
License #: 0225021862, WVB190300549 (VA, WV)
Are you Brett A Sowder? Fill out this form to claim your profile or offer a correction.
Dana J Ashlock
Samson Properties
Recent sales*
23
Local sales*
6
Price range*
$215K - $980K
Typical price*
$430,000
Highlights
About
First-time buyers
Single-family homes
Townhouses
Condos
Dana J Ashlock is a real estate agent who is primarily active in Washington DC, DC. They work with sellers and buyers and have closed at least 10 transactions over the past 12 months — 23 in the past two years. Dana J Ashlock's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 52% sellers, 48% buyers
Total recent sales: 23
Local ranking by total sales: #224
State ranking by total sales: #7,331
Median days on market: 71 days
Median sale-to-list ratio: 100%
License #: 0225265506 (MD, VA, WV)
Are you Dana J Ashlock? Fill out this form to claim your profile or offer a correction.
Bailey Scot Cooper
RE/MAX Gateway
Recent sales*
34
Local sales*
25
Price range*
$245K - $650K
Typical price*
$388,450
Highlights
About
Military buyers
First-time buyers
Single-family homes
Townhouses
Bailey Scot Cooper is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 17 transactions over the past 12 months — 34 in the past two years. Bailey Scot Cooper's experience includes first-time homebuyers, VA loans and military buyers, and sales involving HOAs.
Works with: 38% sellers, 62% buyers
Total recent sales: 34
Local ranking by total sales: #39
State ranking by total sales: #1,968
Median days on market: 58 days
Median sale-to-list ratio: 102%
License #: 0225240867 (VA, WV)
Are you Bailey Scot Cooper? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Stacey L Mullins
ERA Oakcrest Realty, Inc.
Recent sales*
34
Local sales*
21
Price range*
$215K - $757K
Typical price*
$360,000
Highlights
About
Pricing strategyFast sales
Negotiation expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Stacey L Mullins is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 21 transactions over the past 12 months — 34 in the past two years. Stacey L Mullins's experience includes VA loans and military buyers, first-time homebuyers, and sales involving HOAs.
Works with: 38% sellers, 62% buyers
Total recent sales: 34
Local ranking by total sales: #53
State ranking by total sales: #2,609
Median days on market: 43 days
Median sale-to-list ratio: 100%
License #: 0025213348 (VA)
Are you Stacey L Mullins? Fill out this form to claim your profile or offer a correction.
Michelle L Belford
NextHome Realty Select
Recent sales*
24
Local sales*
21
Price range*
$235K - $1000K
Typical price*
$351,250
Highlights
About
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Michelle L Belford is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 11 transactions over the past 12 months — 24 in the past two years. Michelle L Belford's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 50% sellers, 50% buyers
Total recent sales: 24
Local ranking by total sales: #52
State ranking by total sales: #2,430
Median days on market: 50 days
Median sale-to-list ratio: 100%
License #: 0225227178 (VA)
Are you Michelle L Belford? Fill out this form to claim your profile or offer a correction.
Karen M Ohare
Colony Realty
Recent sales*
11
Local sales*
9
Price range*
$236K - $670K
Typical price*
$422,000
Highlights
About
HOA experience
Single-family homes
Townhouses
Karen M Ohare is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 7 transactions over the past 12 months — 11 in the past two years. Karen M Ohare's experience includes sales involving HOAs and VA loans and military buyers.
Works with: 55% sellers, 45% buyers
Total recent sales: 11
Local ranking by total sales: #160
State ranking by total sales: #5,782
Median days on market: 35 days
Median sale-to-list ratio: 100%
License #: 0225066564 (VA)
Are you Karen M Ohare? Fill out this form to claim your profile or offer a correction.
What to know about top real estate agents in Winchester, VA
Top Winchester real estate agents combine deep, local expertise with higher-than-average performance. Here’s what that looks like in Winchester.
General
High transaction volume: Does more than 22 sales per year (local median)
Well established: At least 3–5+ years of experience in the local market
Good reputation: High total review count and average ratings
Sellers
Pricing expertise: Few-to-no price drops
High sale-to-list ratios: Typically sells near or above list price (median sale-to-list in Winchester is 100%)
Strong marketing strategy: Beautiful photos, compelling listing descriptions, maximum visibility
Faster-than-average sales: Gets homes under contract quickly (median sale timeline in Winchester is 68 days)
Buyers
Strong negotiator: The best buyer’s agents in Winchester often save 5-10% off list price
Local expertise: Know neighborhoods, schools, amenities, regulations
Responsive and accessible: Reviews consistently call out these specific traits
Most likely, yes. The vast majority of home sellers in Winchester will get the best outcome and most money selling with a top local real estate agent. That said, it really depends on your goals.
Consider listing with a Winchester realtor if:
You're aiming for top dollar or need help navigating pricing and offers
You want someone to handle the full process—marketing, showings, negotiation, paperwork
Your property is typical for the area and priced at or above $200,000
You’re cost-conscious and want to save on commission with a discount real estate broker
You want to avoid realtor commission altogether and are comfortable trying FSBO (for sale by owner), knowing that FSBO sales usually net less and require a lot of work.
Typically, this gets split between the listing and buyer’s agents (2.75% and 2.75%, respectively).
Rates are negotiable and may be lower for higher-priced homes or repeat clients.
Following the NAR settlement, buyers may need to negotiate their agent's fee directly.
Whether you're hiring a buyer's or seller's agent, you should ask about their past experience. You should find out their plan to market a property you're selling or how they will help you find the perfect home to buy. You should also ask how often they've handled homes in the price point and neighborhood that you're selling or purchasing in.
It's a good idea to review at least three real estate agents, so you can compare their offerings. You'll want to find an agent that's the best fit, so focus on their communication skills, their professionalism, their pricing, and their familiarity with transactions similar to yours.
If you’re both selling a home and purchasing a new one, using the same agent can simplify the process. But you’ll need to find an agent with a successful track record as both a listing agent and a buyer’s agent. While some real estate agents do both, some of the best real estate professionals specialize in either representing buyers or listing properties
If a traditional agent isn’t the right fit, here are some Winchester-area alternatives:
No agent involvement, no commission—but you’ll do everything yourself.
FSBO homes typically sell for less, so weigh potential savings vs. final sale price.
Pro tip: Even if you go non-traditional, consider services like Clever or local offer platforms — they help you compare your options and connect with agents or investors offering discounts, fast offers, or both.
Winchester, Virginia is currently a buyer's market, due to fewer active homebuyers and more homes available for sale.
The market has an average of 2 months of supply, meaning it would take about that long for all available homes to sell if no new listings were added. There were 576 homes for sale in Winchester in the last month. Sellers added 232 new listings, and 182 home sales closed in that time.
On average, properties spend 68 days on the market, and it takes 43 days for a home to go under contract.
Homes in Winchester, Virginia are selling for more on average compared to the previous month. More sellers reduced their listing price this month compared to last month.
252 homes dropped in price this month. That's around 24% of all homes on the market, compared to the 18.39% of listings that lowered prices the month before.
The median home in Winchester, Virginia ultimately sells for its original list price: $399,990.
How we research and evaluate top realtors in Winchester
Data sources
Our rankings are powered by real estate transaction data, internal research, and other publicly available sources. We compiled and analyzed over 940,200 data points for 313 real estate agents across Winchester, Virginia.
Any customer ratings and reviews surfaced on this page are powered by Zillow Group via the Zillow Bridge API. Average ratings, review counts, and individual reviews are sourced directly from Zillow's verified review platform and refreshed regularly. Some reviews may be for team members associated with the agent.
We make every effort to ensure accuracy, but no dataset is perfect. Some activity may not be captured if information isn’t available or accurate from our sources. We update and refine our data regularly to improve coverage and reliability.
Methodology
There’s no single “best” real estate agent — the right fit depends on your goals and situation. Our approach is designed to highlight agents with strong, well-rounded performance and make it easier to compare real estate agents in Winchester.
We look at factors that matter most to typical buyers and sellers, such as:
Transaction volume and recent activity
Balance of buyer- and seller-side representation
Pricing accuracy and negotiation outcomes
Speed of sales relative to the local market
Years of experience and proven track record
Specialized expertise with certain property types or client needs
We use these key indicators to surface agents who are likely to be a good fit for most people, while giving you the data you need to decide which qualities matter most for your own situation.
Ongoing updates
Rankings are updated regularly as new data becomes available. Our goal is to provide a clear, objective view of agent performance to help you make an informed choice when hiring a real estate professional.
