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Updated April 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 308 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 (April 2026 rankings)
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Top 1% local
Offer strategy
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Daniel J Whitacre is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 71 transactions over the past 12 months — 147 in the past two years. Daniel J Whitacre's experience includes first-time homebuyers, luxury homes, and properties in senior communities.
Works with: 62% sellers, 38% buyers
Total recent sales: 147
Local ranking by total sales: #2
State ranking by total sales: #37
Median days on market: 42 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.
Top 1% local
Listing specialist
Neighborhood expert
Repeat clients
Luxury homes
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Vacant land
Sheila R Pack is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 86 transactions over the past 12 months — 158 in the past two years. Sheila R Pack's experience includes sales involving HOAs, luxury homes, and properties in senior communities.
Works with: 73% sellers, 27% buyers
Total recent sales: 158
Local ranking by total sales: #1
State ranking by total sales: #35
Median days on market: 44 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 1% 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 active in Winchester, VA. They work with sellers and buyers and have closed at least 58 transactions over the past 12 months — 113 in the past two years. Leslie A Webb's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 45% sellers, 55% buyers
Total recent sales: 113
Local ranking by total sales: #4
State ranking by total sales: #274
Median days on market: 59 days
Median sale-to-list ratio: 100%
License #: 0225228302 (VA, WV)
Are you Leslie A Webb? Fill out this form to claim your profile or offer a correction.
Top 1% local
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Leah R Clowser is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 58 transactions over the past 12 months — 111 in the past two years. Leah R Clowser's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 52% sellers, 48% buyers
Total recent sales: 111
Local ranking by total sales: #5
State ranking by total sales: #317
Median days on market: 46 days
Median sale-to-list ratio: 99.5%
License #: 0225048720, WV0025896 (VA, WV)
Are you Leah R Clowser? Fill out this form to claim your profile or offer a correction.
Top 1% local
Listing specialist
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Vacant land
David K Spence is a real estate agent who is active in Winchester, VA. and have closed at least 41 transactions over the past 12 months — 98 in the past two years. David K Spence's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 80% sellers, 20% buyers
Total recent sales: 98
Local ranking by total sales: #3
State ranking by total sales: #207
Median days on market: 62 days
Median sale-to-list ratio: 100%
License #: 0225071088 (VA)
Are you David K Spence? 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 active in Winchester, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 56 in the past two years. Kelly R Dodd's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 55% sellers, 45% buyers
Total recent sales: 56
Local ranking by total sales: #11
State ranking by total sales: #613
Median days on market: 63 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 10% localFast sales
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Nicole Panos Lewis is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 23 transactions over the past 12 months — 48 in the past two years. Nicole Panos Lewis's experience includes first-time homebuyers, VA loans and military buyers, and sales involving HOAs.
Works with: 40% sellers, 60% buyers
Total recent sales: 48
Local ranking by total sales: #28
State ranking by total sales: #1,384
Median days on market: 52 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.
20+ years experience
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Sergio A Vitela is a real estate agent who is active in Washington, DC. Sergio A Vitela has worked in real estate for over 20 years. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 51 in the past two years. Sergio A Vitela's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 35% sellers, 65% buyers
Total recent sales: 51
Local ranking by total sales: #242
State ranking by total sales: #6,485
Median days on market: 44 days
Median sale-to-list ratio: 100%
License #: 0225203870, 653125, WVA230040272 (DC, MD, VA, WV)
Are you Sergio A Vitela? Fill out this form to claim your profile or offer a correction.
Top 5% local
Neighborhood expert
Repeat clients
Luxury homes
First-time buyers
Single-family homes
Manufactured homes
Keenan L Shanholtz is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 29 transactions over the past 12 months — 53 in the past two years. Keenan L Shanholtz's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 64% sellers, 36% buyers
Total recent sales: 53
Local ranking by total sales: #10
State ranking by total sales: #612
Median days on market: 46 days
Median sale-to-list ratio: 100%
Are you Keenan L Shanholtz? 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
Multi-family homes
Condos
Roxanna D Grimes is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 48 transactions over the past 12 months — 82 in the past two years. Roxanna D Grimes's experience includes VA loans and military buyers, first-time homebuyers, and sales involving HOAs.
Works with: 60% sellers, 40% buyers
Total recent sales: 82
Local ranking by total sales: #12
State ranking by total sales: #643
Median days on market: 49 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.
Top 5% local
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 active in Winchester, VA. They work with sellers and buyers and have closed at least 35 transactions over the past 12 months — 61 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: 67% sellers, 33% buyers
Total recent sales: 61
Local ranking by total sales: #9
State ranking by total sales: #587
Median days on market: 51 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.
Top 10% local
Neighborhood expert
First-time buyers
Single-family homes
Townhouses
Jeanne Mezzatesta is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 39 in the past two years. Jeanne Mezzatesta's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 56% sellers, 44% buyers
Total recent sales: 39
Local ranking by total sales: #24
State ranking by total sales: #1,284
Median days on market: 48 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.
Fast sales
Repeat clients
Single-family homes
Townhouses
Julie M Teets is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 34 in the past two years. Julie M Teets's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 34
Local ranking by total sales: #43
State ranking by total sales: #2,072
Median days on market: 49 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.
Top 10% localFast sales
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Anna Mari Fox is a real estate agent who is 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. Anna Mari Fox's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 44% sellers, 56% buyers
Total recent sales: 48
Local ranking by total sales: #22
State ranking by total sales: #1,115
Median days on market: 36 days
Median sale-to-list ratio: 100%
License #: 0225243594, WVS210301534 (VA, WV)
Are you Anna Mari Fox? Fill out this form to claim your profile or offer a correction.
Pricing strategyFast sales
Negotiation expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Condos
Julie D Shiley is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 16 transactions over the past 12 months — 45 in the past two years. Julie D Shiley's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 45
Local ranking by total sales: #55
State ranking by total sales: #2,694
Median days on market: 196 days
Median sale-to-list ratio: 100%
License #: 0225220202, WVS200300948 (VA, WV)
Are you Julie D Shiley? Fill out this form to claim your profile or offer a correction.
Top 10% localFast sales
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Vacant land
Lori Fountain Bales is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 42 in the past two years. Lori Fountain Bales's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 48% sellers, 52% buyers
Total recent sales: 42
Local ranking by total sales: #25
State ranking by total sales: #1,303
Median days on market: 37 days
Median sale-to-list ratio: 99%
License #: 0225229904, 200301291 (VA, WV)
Are you Lori Fountain Bales? Fill out this form to claim your profile or offer a correction.
Top 5% local
Negotiation expert
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Manufactured homes
Vacant land
Katherine Jane Nazelrod is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 54 in the past two years. Katherine Jane Nazelrod'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: #8
State ranking by total sales: #528
Median days on market: 80 days
Median sale-to-list ratio: 98%
License #: 0225275702, WVA200040101 (VA, WV)
Are you Katherine Jane Nazelrod? Fill out this form to claim your profile or offer a correction.
Top 10% local
Offer strategy
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Mark S Francis is a real estate agent who is 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. Mark S Francis's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 39
Local ranking by total sales: #27
State ranking by total sales: #1,378
Median days on market: 74 days
Median sale-to-list ratio: 99.5%
License #: 0225275514, 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
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Bradley Comstock is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 46 transactions over the past 12 months — 79 in the past two years. Bradley Comstock's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 59% sellers, 41% buyers
Total recent sales: 79
Local ranking by total sales: #7
State ranking by total sales: #493
Median days on market: 51 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.
Repeat clients
HOA experience
First-time buyers
Single-family homes
Manufactured homes
Kristi D Cooper is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 4 transactions over the past 12 months — 21 in the past two years. Kristi D Cooper's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 43% sellers, 57% buyers
Total recent sales: 21
Local ranking by total sales: #60
State ranking by total sales: #3,044
Median days on market: 52 days
Median sale-to-list ratio: 98%
License #: 0225232654 (VA, WV)
Are you Kristi D Cooper? Fill out this form to claim your profile or offer a correction.
Fast sales
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Kristen Kerns is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 21 transactions over the past 12 months — 43 in the past two years. Kristen Kerns's experience includes first-time homebuyers, VA loans and military buyers, and sales involving HOAs.
Works with: 40% sellers, 60% buyers
Total recent sales: 43
Local ranking by total sales: #42
State ranking by total sales: #1,847
Median days on market: 43 days
Median sale-to-list ratio: 100%
License #: 0225227214 (VA, WV)
Are you Kristen Kerns? Fill out this form to claim your profile or offer a correction.
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Katherine Landi Jordan is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 14 transactions over the past 12 months — 29 in the past two years. Katherine Landi Jordan's experience includes sales involving HOAs, properties in senior communities, and first-time homebuyers.
Works with: 52% sellers, 48% buyers
Total recent sales: 29
Local ranking by total sales: #50
State ranking by total sales: #2,539
Median days on market: 52 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.
Fast sales
Repeat clients
First-time buyers
Single-family homes
Townhouses
Jeffrey W Konrady is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 9 transactions over the past 12 months — 28 in the past two years. Jeffrey W Konrady's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Works with: 46% sellers, 54% buyers
Total recent sales: 28
Local ranking by total sales: #66
State ranking by total sales: #3,016
Median days on market: 38 days
Median sale-to-list ratio: 100%
License #: 0225207222 (VA, WV)
Are you Jeffrey W Konrady? 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
Townhouses
Condos
Traci J Shoberg is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 33 transactions over the past 12 months — 61 in the past two years. Traci J Shoberg's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 61% sellers, 39% buyers
Total recent sales: 61
Local ranking by total sales: #14
State ranking by total sales: #757
Median days on market: 65 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.
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Heloisa P Amar is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 23 transactions over the past 12 months — 59 in the past two years. Heloisa P Amar's experience includes first-time homebuyers and sales involving HOAs.
Works with: 36% sellers, 64% buyers
Total recent sales: 59
Local ranking by total sales: #15
State ranking by total sales: #772
Median days on market: 82 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.
Negotiation expert
Repeat clients
Single-family homes
Townhouses
Ariel Renee Guzman is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 8 transactions over the past 12 months — 11 in the past two years. Ariel Renee Guzman is experienced with first-time homebuyers.
Works with: 45% sellers, 55% buyers
Total recent sales: 11
Local ranking by total sales: #135
State ranking by total sales: #5,214
Median days on market: 51 days
Median sale-to-list ratio: 98%
License #: 0225263292 (VA)
Are you Ariel Renee Guzman? Fill out this form to claim your profile or offer a correction.
Top 10% localFast sales
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Christopher W Roszko is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 30 transactions over the past 12 months — 46 in the past two years. Christopher W Roszko's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 46% sellers, 54% buyers
Total recent sales: 46
Local ranking by total sales: #29
State ranking by total sales: #1,340
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.
Top 5% localFast sales
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Deborah Matthews is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 57 in the past two years. Deborah Matthews's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 60% sellers, 40% buyers
Total recent sales: 57
Local ranking by total sales: #17
State ranking by total sales: #839
Median days on market: 48 days
Median sale-to-list ratio: 100%
License #: 0225056972 (VA)
Are you Deborah Matthews? Fill out this form to claim your profile or offer a correction.
Repeat clients
HOA experience
Military buyers
Single-family homes
Townhouses
Condos
Jen Richards is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 15 transactions over the past 12 months — 24 in the past two years. Jen Richards's experience includes sales involving HOAs and VA loans and military buyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 24
Local ranking by total sales: #113
State ranking by total sales: #4,549
Median days on market: 49 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.
HOA experience
Military buyers
Senior living
Single-family homes
Townhouses
Wendy S Conner is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 18 transactions over the past 12 months — 34 in the past two years. Wendy S Conner's experience includes VA loans and military buyers, sales involving HOAs, and properties in senior communities.
Works with: 50% sellers, 50% buyers
Total recent sales: 34
Local ranking by total sales: #54
State ranking by total sales: #2,609
Median days on market: 146 days
Median sale-to-list ratio: 100%
License #: 0225047999 (VA)
Are you Wendy S Conner? Fill out this form to claim your profile or offer a correction.
Repeat clients
First-time buyers
Single-family homes
Townhouses
Melissa A Johnston is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 12 transactions over the past 12 months — 21 in the past two years. Melissa A Johnston's experience includes first-time homebuyers and VA loans and military buyers.
Works with: 52% sellers, 48% buyers
Total recent sales: 21
Local ranking by total sales: #76
State ranking by total sales: #3,505
Median days on market: 42 days
Median sale-to-list ratio: 100%
License #: 0225046276 (VA)
Are you Melissa A Johnston? Fill out this form to claim your profile or offer a correction.
Top 10% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Manufactured homes
Kaitlyn Behr is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 35 in the past two years. Kaitlyn Behr's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 54% sellers, 46% buyers
Total recent sales: 35
Local ranking by total sales: #30
State ranking by total sales: #1,541
Median days on market: 54 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.
Top 10% local
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Stephanie Ryall is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 38 in the past two years. Stephanie Ryall's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Works with: 42% sellers, 58% buyers
Total recent sales: 38
Local ranking by total sales: #33
State ranking by total sales: #1,584
Median days on market: 58 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.
Fast sales
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Manufactured homes
Condos
Paul J Gallagher Jr is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 49 in the past two years. Paul J Gallagher Jr's experience includes sales involving HOAs, properties in senior communities, and first-time homebuyers.
Works with: 57% sellers, 43% buyers
Total recent sales: 49
Local ranking by total sales: #36
State ranking by total sales: #1,567
Median days on market: 34 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.
Neighborhood expert
Repeat clients
Senior living
Single-family homes
Townhouses
Jeffrey M Webber is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 7 transactions over the past 12 months — 13 in the past two years. Jeffrey M Webber's experience includes properties in senior communities and sales involving HOAs.
Works with: 54% sellers, 46% buyers
Total recent sales: 13
Local ranking by total sales: #103
State ranking by total sales: #4,214
Median days on market: 47 days
Median sale-to-list ratio: 99%
License #: 225002434 (VA)
Are you Jeffrey M Webber? Fill out this form to claim your profile or offer a correction.
Top 10% local
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Brett A Sowder is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 34 transactions over the past 12 months — 72 in the past two years. Brett A Sowder's experience includes first-time homebuyers, properties in senior communities, and luxury homes.
Works with: 58% sellers, 42% buyers
Total recent sales: 72
Local ranking by total sales: #20
State ranking by total sales: #955
Median days on market: 67 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.
Fast sales
Listing specialist
28+ years experience
Repeat clients
First-time buyers
Single-family homes
Townhouses
James W Amick is a real estate agent who is active in Washington, DC. James W Amick has worked in real estate for over 28 years. They primarily work with sellers and have closed at least 9 transactions over the past 12 months — 28 in the past two years. James W Amick's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Works with: 82% sellers, 18% buyers
Total recent sales: 28
Local ranking by total sales: #182
State ranking by total sales: #6,249
Median days on market: 47 days
Median sale-to-list ratio: 100%
License #: 0225047667, 645305 (MD, PA, VA, WV)
Are you James W Amick? Fill out this form to claim your profile or offer a correction.
Listing specialist
Repeat clients
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Amanda M Downs is a real estate agent who is active in Harrisonburg, VA. They work with sellers and buyers and have closed at least 16 transactions over the past 12 months — 37 in the past two years. Amanda M Downs's experience includes first-time homebuyers and sales involving HOAs.
Works with: 70% sellers, 30% buyers
Total recent sales: 37
Local ranking by total sales: #132
State ranking by total sales: #1,779
Median days on market: 53 days
Median sale-to-list ratio: 100%
License #: 0225204780 (VA)
Are you Amanda M Downs? Fill out this form to claim your profile or offer a correction.
HOA experience
First-time buyers
Single-family homes
Townhouses
Cynthia K Greenya is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 33 in the past two years. Cynthia K Greenya's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 61% sellers, 39% buyers
Total recent sales: 33
Local ranking by total sales: #81
State ranking by total sales: #3,635
Median days on market: 56 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.
Fast sales
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Jodi Costello is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 11 transactions over the past 12 months — 22 in the past two years. Jodi Costello's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 41% sellers, 59% buyers
Total recent sales: 22
Local ranking by total sales: #96
State ranking by total sales: #3,945
Median days on market: 34 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.
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Matthew Michael Kilmer is a real estate agent who is 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. Matthew Michael Kilmer's experience includes first-time homebuyers and VA loans and military buyers.
Works with: 52% sellers, 48% buyers
Total recent sales: 46
Local ranking by total sales: #40
State ranking by total sales: #1,745
Median days on market: 247 days
Median sale-to-list ratio: 100%
License #: 0225238026, WVS200301033 (VA, WV)
Are you Matthew Michael Kilmer? Fill out this form to claim your profile or offer a correction.
Top 5% localFast sales
Neighborhood expert
HOA experience
First-time buyers
Single-family homes
Townhouses
Teresa L Strohmeyer is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 23 transactions over the past 12 months — 54 in the past two years. Teresa L Strohmeyer's experience includes sales involving HOAs and first-time homebuyers.
Works with: 69% sellers, 31% buyers
Total recent sales: 54
Local ranking by total sales: #13
State ranking by total sales: #724
Median days on market: 43 days
Median sale-to-list ratio: 99%
License #: 0225026152, WV0021378 (VA, WV)
Are you Teresa L Strohmeyer? Fill out this form to claim your profile or offer a correction.
Offer strategy
Negotiation expert
Repeat clients
Single-family homes
Townhouses
Condos
Erika D De Azagra is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 11 transactions over the past 12 months — 22 in the past two years. Erika D De Azagra's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Works with: 55% sellers, 45% buyers
Total recent sales: 22
Local ranking by total sales: #73
State ranking by total sales: #3,414
Median days on market: 55 days
Median sale-to-list ratio: 99%
License #: 0225081741 (VA, WV)
Are you Erika D De Azagra? Fill out this form to claim your profile or offer a correction.
Fast sales
Negotiation expert
Repeat clients
First-time buyers
Single-family homes
Vacant land
Edward L Beightol Iii is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 6 transactions over the past 12 months — 18 in the past two years. Edward L Beightol Iii's experience includes first-time homebuyers and sales involving HOAs.
Works with: 61% sellers, 39% buyers
Total recent sales: 18
Local ranking by total sales: #72
State ranking by total sales: #3,410
Median days on market: 44 days
Median sale-to-list ratio: 100%
License #: 0225034564, WV0004066 (VA, WV)
Are you Edward L Beightol Iii? Fill out this form to claim your profile or offer a correction.
Offer strategy
Negotiation expert
Repeat clients
First-time buyers
Senior living
Single-family homes
Townhouses
Cara L Wilkins is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 8 transactions over the past 12 months — 14 in the past two years. Cara L Wilkins's experience includes first-time homebuyers, properties in senior communities, and luxury homes.
Works with: 36% sellers, 64% buyers
Total recent sales: 14
Local ranking by total sales: #153
State ranking by total sales: #5,627
Median days on market: 46 days
Median sale-to-list ratio: 100%
License #: 0225065889 (VA)
Are you Cara L Wilkins? Fill out this form to claim your profile or offer a correction.
Top 5% local
Neighborhood expert
Repeat clients
HOA experience
Senior living
Single-family homes
Townhouses
Laura D White is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 43 in the past two years. Laura D White's experience includes sales involving HOAs, properties in senior communities, and luxury homes.
Works with: 67% sellers, 33% buyers
Total recent sales: 43
Local ranking by total sales: #16
State ranking by total sales: #850
Median days on market: 45 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.
Fast sales
Listing specialist
Repeat clients
HOA experience
Single-family homes
Townhouses
Condos
Jacob Taylor is a real estate agent who is active in Baltimore, MD. They primarily work with sellers and have closed at least 31 transactions over the past 12 months — 55 in the past two years. Jacob Taylor's experience includes luxury homes, sales involving HOAs, and first-time homebuyers.
Works with: 84% sellers, 16% buyers
Total recent sales: 55
Local ranking by total sales: #141
State ranking by total sales: #2,835
Median days on market: 59 days
Median sale-to-list ratio: 100%
License #: 0225188943, 653076, WVB180040011 (MD, VA, WV)
Are you Jacob Taylor? Fill out this form to claim your profile or offer a correction.
Neighborhood expert
HOA experience
First-time buyers
Single-family homes
Townhouses
Michele L Gibson is a real estate agent who is active in Washington, DC. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 42 in the past two years. Michele L Gibson's experience includes luxury homes, sales involving HOAs, and first-time homebuyers.
Works with: 57% sellers, 43% buyers
Total recent sales: 42
Local ranking by total sales: #68
State ranking by total sales: #3,277
Median days on market: 71 days
Median sale-to-list ratio: 98%
License #: 0226025721, WV0027433 (VA, WV)
Are you Michele L Gibson? Fill out this form to claim your profile or offer a correction.
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Michelle L Belford is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 13 transactions over the past 12 months — 23 in the past two years. Michelle L Belford's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 61% sellers, 39% buyers
Total recent sales: 23
Local ranking by total sales: #53
State ranking by total sales: #2,570
Median days on market: 48 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.
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Vacant land
Caroline W Barb is a real estate agent who is active in Washington, DC. They work with sellers and buyers and have closed at least 10 transactions over the past 12 months — 21 in the past two years. Caroline W Barb's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 43% sellers, 57% buyers
Total recent sales: 21
Local ranking by total sales: #191
State ranking by total sales: #6,650
Median days on market: 49 days
Median sale-to-list ratio: 100%
License #: 0225243462, 275102 (GA, VA)
Are you Caroline W Barb? 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 55 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.
Sell with a top agent and save
With Clever, sellers can list with a top local agent for just 1.5% (or $3,000 flat) — up to 50% less than the typical rate in Winchester.
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 4.8 months of supply, meaning it would take about that long for all available homes to sell if no new listings were added. There were 581 homes for sale in Winchester in the last month. Sellers added 63 new listings, and 29 home sales closed in that time.
On average, properties spend 55 days on the market, and it takes 36 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.
35 homes dropped in price this month. That's around 6% of all homes on the market, compared to the 5.1% of listings that lowered prices the month before.
The median home in Winchester, Virginia ultimately sells for its original list price: $399,250.
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 918,300 data points for 308 real estate agents across Winchester, Virginia.
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.
