Clever lets you compare top Winchester realtors and unlock special rates that save you thousands.
Requesting agents is fast, easy, and free.
Updated July 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 306 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.
Identify agents with solid experience in your price range, neighborhood, and property type
Prioritize agents with high customer review counts and strong ratings
Look at active or recently sold listings to assess marketing quality and performance
Interview 2–3 agents minimum (actually meet or speak with them)
Gauge communication, honesty, and expertise during the interview process
Verify included services and specifics about terms and pricing before signing anything
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 (July 2026 rankings)
Reset all filters
Sorry, we don't currently have verified agents matching that criteria. Reset your filters to continue your search — or try our free service below to get matched with top agents.
Highly rated
Top 1% local
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 67 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: 64% sellers, 36% buyers
Total recent sales: 147
Local ranking by total sales: #1
State ranking by total sales: #37
Median days on market: 44 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% localFast sales
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 82 transactions over the past 12 months — 155 in the past two years. Sheila R Pack's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 74% sellers, 26% buyers
Total recent sales: 155
Local ranking by total sales: #2
State ranking by total sales: #38
Median days on market: 45 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.
Highly rated
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 59 transactions over the past 12 months — 112 in the past two years. Leah R Clowser's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 55% sellers, 45% buyers
Total recent sales: 112
Local ranking by total sales: #3
State ranking by total sales: #312
Median days on market: 50 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 1% local
Neighborhood expert
Repeat clients
Luxury homes
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 55 transactions over the past 12 months — 106 in the past two years. Leslie A Webb's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 43% sellers, 57% buyers
Total recent sales: 106
Local ranking by total sales: #5
State ranking by total sales: #358
Median days on market: 62 days
Median sale-to-list ratio: 100%
License #: 0225228302, WVS190300602 (VA, WV)
Are you Leslie A Webb? 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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 21 transactions over the past 12 months — 40 in the past two years. Jeanne Mezzatesta's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 53% sellers, 48% buyers
Total recent sales: 40
Local ranking by total sales: #19
State ranking by total sales: #1,068
Median days on market: 49 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.
Highly rated
Top 1% local
Listing specialist
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
David K Spence is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 41 transactions over the past 12 months — 88 in the past two years. David K Spence's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 78% sellers, 22% buyers
Total recent sales: 88
Local ranking by total sales: #4
State ranking by total sales: #320
Median days on market: 69 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.
Highly rated
Top 5% local
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 59 transactions over the past 12 months — 96 in the past two years. Roxanna D Grimes's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 60% sellers, 40% buyers
Total recent sales: 96
Local ranking by total sales: #8
State ranking by total sales: #446
Median days on market: 51 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.
Highly rated
Top 5% local
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 34 transactions over the past 12 months — 67 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: 70% sellers, 30% buyers
Total recent sales: 67
Local ranking by total sales: #9
State ranking by total sales: #484
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 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 35 transactions over the past 12 months — 60 in the past two years. Kelly R Dodd's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 57% sellers, 43% buyers
Total recent sales: 60
Local ranking by total sales: #11
State ranking by total sales: #561
Median days on market: 64 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
Keenan L Shanholtz
WEST VIRGINIA LAND & HOME REALTY
Recent sales*
51
Local sales*
44
Price range*
$40K - $1.3M
Typical price*
$399,900
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 26 transactions over the past 12 months — 51 in the past two years. Keenan L Shanholtz's experience includes luxury homes and first-time homebuyers.
Works with: 63% sellers, 37% buyers
Total recent sales: 51
Local ranking by total sales: #13
State ranking by total sales: #734
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.
Lori Fountain Bales
Keller Williams Realty
Recent sales*
45
Local sales*
34
Price range*
$230K - $1.4M
Typical price*
$504,990
Highlights
About
Top 10% localFast sales
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
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 22 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: #20
State ranking by total sales: #1,179
Median days on market: 38 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.
Christopher W Roszko
Colony Realty
Recent sales*
49
Local sales*
33
Price range*
$110K - $1.1M
Typical price*
$330,000
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 25 transactions over the past 12 months — 49 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: 49% sellers, 51% buyers
Total recent sales: 49
Local ranking by total sales: #23
State ranking by total sales: #1,156
Median days on market: 37 days
Median sale-to-list ratio: 100%
License #: WVS230302703 (VA, WV)
Are you Christopher W Roszko? Fill out this form to claim your profile or offer a correction.
Julie M Teets
ERA Oakcrest Realty, Inc.
Recent sales*
42
Local sales*
29
Price range*
$223K - $1.3M
Typical price*
$420,635
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 27 transactions over the past 12 months — 42 in the past two years. Julie M Teets'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: #31
State ranking by total sales: #1,565
Median days on market: 48 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 Local Pro
Mark S Francis
Real Broker, LLC
Recent sales*
39
Local sales*
32
Price range*
$207K - $1.2M
Typical price*
$400,000
Highlights
About
Top 10% local
Offer strategy
Negotiation 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 19 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: 54% sellers, 46% buyers
Total recent sales: 39
Local ranking by total sales: #26
State ranking by total sales: #1,333
Median days on market: 73 days
Median sale-to-list ratio: 100%
License #: 0225275514, WVA250040374 (VA, WV)
Are you Mark S Francis? Fill out this form to claim your profile or offer a correction.
Michelle L Belford
NextHome Realty Select
Recent sales*
25
Local sales*
22
Price range*
$235K - $931K
Typical price*
$352,500
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 13 transactions over the past 12 months — 25 in the past two years. Michelle L Belford's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 25
Local ranking by total sales: #48
State ranking by total sales: #2,272
Median days on market: 42 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.
Paul J Gallagher Jr
Colony Realty
Recent sales*
52
Local sales*
34
Price range*
$120K - $1.1M
Typical price*
$425,000
Highlights
About
Top 10% localFast sales
Neighborhood expert
Repeat clients
HOA experience
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 19 transactions over the past 12 months — 52 in the past two years. Paul J Gallagher Jr's experience includes sales involving HOAs, properties in senior communities, and luxury homes.
Works with: 56% sellers, 44% buyers
Total recent sales: 52
Local ranking by total sales: #21
State ranking by total sales: #1,137
Median days on market: 35 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.
Top Local Pro
Bradley Comstock
ERA Oakcrest Realty, Inc.
Recent sales*
83
Local sales*
54
Price range*
$180K - $1.1M
Typical price*
$422,000
Highlights
About
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 44 transactions over the past 12 months — 83 in the past two years. Bradley Comstock's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 61% sellers, 39% buyers
Total recent sales: 83
Local ranking by total sales: #7
State ranking by total sales: #435
Median days on market: 50 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.
Julie D Shiley
Coldwell Banker Realty
Recent sales*
42
Local sales*
16
Price range*
$215K - $1.4M
Typical price*
$424,500
Highlights
About
Repeat clients
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 Winchester, VA. They work with sellers and buyers and have closed at least 13 transactions over the past 12 months — 42 in the past two years. Julie D Shiley's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 55% sellers, 45% buyers
Total recent sales: 42
Local ranking by total sales: #77
State ranking by total sales: #3,283
Median days on market: 194 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 Local Pro
Teresa L Strohmeyer
ERA Oakcrest Realty, Inc.
Recent sales*
55
Local sales*
40
Price range*
$80K - $935K
Typical price*
$349,000
Highlights
About
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 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: 62% sellers, 38% buyers
Total recent sales: 55
Local ranking by total sales: #17
State ranking by total sales: #896
Median days on market: 48 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.
Tiffany J Hunter
ERA Oakcrest Realty, Inc.
Local sales*
31
Price range*
$206K - $740K
Typical price*
$450,000
Highlights
About
Top 10% local
Negotiation expert
First-time buyers
Single-family homes
Townhouses
Multi-family homes
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 16 transactions over the past 12 months — 31 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: 31
Local ranking by total sales: #27
State ranking by total sales: #1,424
Median days on market: 56 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 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 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. Anna Mari Fox's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 43% sellers, 57% buyers
Total recent sales: 46
Local ranking by total sales: #25
State ranking by total sales: #1,285
Median days on market: 35 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.
Liz Owings
Samson Properties
Recent sales*
31
Local sales*
16
Price range*
$135K - $825K
Typical price*
$347,500
Highlights
About
Pricing strategy
Negotiation expert
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Liz Owings 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 — 31 in the past two years. Liz Owings's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Works with: 42% sellers, 58% buyers
Total recent sales: 31
Local ranking by total sales: #79
State ranking by total sales: #3,530
Median days on market: 53 days
Median sale-to-list ratio: 100%
License #: 225247167 (VA)
Are you Liz Owings? Fill out this form to claim your profile or offer a correction.
Nicole Panos Lewis
Coldwell Banker Premier
Recent sales*
46
Local sales*
27
Price range*
$160K - $765K
Typical price*
$365,000
Highlights
About
Neighborhood expert
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 21 transactions over the past 12 months — 46 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: 35% sellers, 65% buyers
Total recent sales: 46
Local ranking by total sales: #36
State ranking by total sales: #1,779
Median days on market: 104 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.
Michele L Gibson
Samson Properties
Recent sales*
48
Local sales*
23
Price range*
$253K - $1.4M
Typical price*
$584,995
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 27 transactions over the past 12 months — 48 in the past two years. Michele L Gibson's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Works with: 56% sellers, 44% buyers
Total recent sales: 48
Local ranking by total sales: #46
State ranking by total sales: #2,271
Median days on market: 72 days
Median sale-to-list ratio: 99%
License #: 0226025721, 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.
Carolina M Mosquera
Weichert, REALTORS
Recent sales*
58
Local sales*
12
Price range*
$185K - $1M
Typical price*
$465,000
Highlights
About
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Condos
Carolina M Mosquera is a real estate agent who is primarily active in Washington, DC. They work with sellers and buyers and have closed at least 29 transactions over the past 12 months — 58 in the past two years. Carolina M Mosquera's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Works with: 40% sellers, 60% buyers
Total recent sales: 58
Local ranking by total sales: #114
State ranking by total sales: #4,494
Median days on market: 69 days
Median sale-to-list ratio: 100%
License #: 0225065374 (MD, VA, WV)
Are you Carolina M Mosquera? Fill out this form to claim your profile or offer a correction.
Jeffrey M Webber
Long & Foster Real Estate, Inc.
Local sales*
13
Price range*
$250K - $585K
Typical price*
$386,000
Highlights
About
Neighborhood expert
Repeat clients
Senior living
Single-family homes
Townhouses
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 4 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: #97
State ranking by total sales: #4,258
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.
James W King Jr
Re/Max Roots
Recent sales*
29
Local sales*
20
Price range*
$92K - $1.2M
Typical price*
$432,500
Highlights
About
HOA experience
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 — 29 in the past two years. James W King Jr's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 52% sellers, 48% buyers
Total recent sales: 29
Local ranking by total sales: #55
State ranking by total sales: #2,692
Median days on market: 53 days
Median sale-to-list ratio: 99%
License #: 0225065135 (VA, WV)
Are you James W King Jr? Fill out this form to claim your profile or offer a correction.
Kristi D Cooper
Realty ONE Group Old Towne
Recent sales*
22
Local sales*
19
Price range*
$91K - $825K
Typical price*
$352,500
Highlights
About
Repeat clients
HOA experience
First-time buyers
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 5 transactions over the past 12 months — 22 in the past two years. Kristi D Cooper's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 45% sellers, 55% buyers
Total recent sales: 22
Local ranking by total sales: #60
State ranking by total sales: #2,904
Median days on market: 57 days
Median sale-to-list ratio: 97.5%
License #: 0225232654 (VA, WV)
Are you Kristi D Cooper? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Heloisa P Amar
Samson Properties
Recent sales*
57
Local sales*
42
Price range*
$225K - $465K
Typical price*
$319,000
Highlights
About
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 23 transactions over the past 12 months — 57 in the past two years. Heloisa P Amar's experience includes first-time homebuyers and sales involving HOAs.
Works with: 37% sellers, 63% buyers
Total recent sales: 57
Local ranking by total sales: #14
State ranking by total sales: #796
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.
James W Amick
Remax Roots & Remax Achievers
Recent sales*
26
Local sales*
7
Price range*
$201K - $965K
Typical price*
$355,000
Highlights
About
Pricing strategyFast sales
Negotiation expert
20+ years experience
Listing specialist
Repeat clients
First-time buyers
Single-family homes
Townhouses
James W Amick is a real estate agent who is primarily active in Washington, DC. James W Amick has worked in real estate for over 28 years. They work with sellers and buyers and have closed at least 12 transactions over the past 12 months — 26 in the past two years. James W Amick's experience includes first-time homebuyers and VA loans and military buyers.
Est. years experience: 28
Works with: 73% sellers, 27% buyers
Total recent sales: 26
Local ranking by total sales: #206
State ranking by total sales: #6,786
Median days on market: 49 days
Median sale-to-list ratio: 100%
License #: 0225047667, 645305 (MD, PA, VA, WV)
Office address: 3363 Shawnee Dr, Winchester, VA 22602, USA
Are you James W Amick? Fill out this form to claim your profile or offer a correction.
Jacob Taylor
Blue Valley Real Estate
Recent sales*
56
Local sales*
9
Price range*
$135K - $1.7M
Typical price*
$384,900
Highlights
About
Listing specialist
Repeat clients
HOA experience
Single-family homes
Townhouses
Condos
Jacob Taylor is a real estate agent who is primarily active in Baltimore, MD. They primarily work with sellers and have closed at least 27 transactions over the past 12 months — 56 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: 56
Local ranking by total sales: #155
State ranking by total sales: #2,864
Median days on market: 67 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.
Brett A Sowder
RE/MAX Roots
Recent sales*
69
Local sales*
30
Price range*
$160K - $1.5M
Typical price*
$387,000
Highlights
About
Top 10% local
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 38 transactions over the past 12 months — 69 in the past two years. Brett A Sowder's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Works with: 57% sellers, 43% buyers
Total recent sales: 69
Local ranking by total sales: #28
State ranking by total sales: #1,364
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.
Stephanie Ryall
Realty ONE Group Old Towne
Recent sales*
35
Local sales*
24
Price range*
$150K - $875K
Typical price*
$375,000
Highlights
About
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 21 transactions over the past 12 months — 35 in the past two years. Stephanie Ryall's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Works with: 40% sellers, 60% buyers
Total recent sales: 35
Local ranking by total sales: #44
State ranking by total sales: #2,177
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.
Top Local Pro
Stacey L Mullins
ERA Oakcrest Realty, Inc.
Recent sales*
33
Local sales*
19
Price range*
$215K - $757K
Typical price*
$355,000
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 22 transactions over the past 12 months — 33 in the past two years. Stacey L Mullins's experience includes first-time homebuyers, VA loans and military buyers, and sales involving HOAs.
Works with: 36% sellers, 64% buyers
Total recent sales: 33
Local ranking by total sales: #61
State ranking by total sales: #2,968
Median days on market: 44 days
Median sale-to-list ratio: 100.5%
License #: 0025213348 (VA)
Are you Stacey L Mullins? Fill out this form to claim your profile or offer a correction.
Bailey Scot Cooper
RE/MAX Gateway
Recent sales*
32
Local sales*
24
Price range*
$245K - $900K
Typical price*
$388,450
Highlights
About
HOA experience
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 18 transactions over the past 12 months — 32 in the past two years. Bailey Scot Cooper's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Works with: 41% sellers, 59% buyers
Total recent sales: 32
Local ranking by total sales: #42
State ranking by total sales: #2,080
Median days on market: 44 days
Median sale-to-list ratio: 101%
License #: 0225240867 (VA, WV)
Are you Bailey Scot Cooper? Fill out this form to claim your profile or offer a correction.
Matthew James Roberts
Redfin Corporation
Recent sales*
59
Local sales*
14
Price range*
$280K - $1.8M
Typical price*
$610,000
Highlights
About
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Matthew James Roberts is a real estate agent who is primarily active in Washington, DC. They work with sellers and buyers and have closed at least 18 transactions over the past 12 months — 59 in the past two years. Matthew James Roberts's experience includes sales involving HOAs, VA loans and military buyers, and luxury homes.
Works with: 39% sellers, 61% buyers
Total recent sales: 59
Local ranking by total sales: #91
State ranking by total sales: #3,539
Median days on market: 43 days
Median sale-to-list ratio: 99%
License #: 846562216 (VA)
Are you Matthew James Roberts? Fill out this form to claim your profile or offer a correction.
Misty Weaver
Samson Properties
Recent sales*
16
Local sales*
13
Price range*
$250K - $735K
Typical price*
$408,000
Highlights
About
HOA experience
Single-family homes
Townhouses
Misty Weaver 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 — 16 in the past two years. Misty Weaver's experience includes sales involving HOAs and properties in senior communities.
Works with: 44% sellers, 56% buyers
Total recent sales: 16
Local ranking by total sales: #101
State ranking by total sales: #4,359
Median days on market: 107 days
Median sale-to-list ratio: 100%
License #: 0225213758 (VA)
Are you Misty Weaver? Fill out this form to claim your profile or offer a correction.
Ed Butler
Samson Properties
Recent sales*
8
Local sales*
6
Price range*
$180K - $700K
Typical price*
$362,000
Highlights
About
Single-family homes
Townhouses
Ed Butler is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 2 transactions over the past 12 months — 8 in the past two years. Ed Butler's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 8
Local ranking by total sales: #230
State ranking by total sales: #7,422
Median days on market: 47 days
Median sale-to-list ratio: 98.5%
License #: WVA220040172 (VA, WV)
Are you Ed Butler? Fill out this form to claim your profile or offer a correction.
Top Local Pro
Katherine Jane Nazelrod
Pioneer Ridge Realty
Recent sales*
54
Local sales*
49
Price range*
$55K - $599K
Typical price*
$240,000
Highlights
About
Top 5% local
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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 25 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: 56% sellers, 44% buyers
Total recent sales: 54
Local ranking by total sales: #10
State ranking by total sales: #560
Median days on market: 90 days
Median sale-to-list ratio: 99%
License #: 0225275702, WVA200040101 (VA, WV)
Are you Katherine Jane Nazelrod? Fill out this form to claim your profile or offer a correction.
Katherine Landi Jordan
Samson Properties
Recent sales*
25
Local sales*
17
Price range*
$212K - $902K
Typical price*
$379,000
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 16 transactions over the past 12 months — 25 in the past two years. Katherine Landi Jordan's experience includes sales involving HOAs, first-time homebuyers, and properties in senior communities.
Works with: 52% sellers, 48% buyers
Total recent sales: 25
Local ranking by total sales: #71
State ranking by total sales: #3,286
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.
Ariel Renee Guzman
RE/MAX Roots
Recent sales*
10
Local sales*
9
Price range*
$290K - $585K
Typical price*
$415,500
Highlights
About
Offer strategy
Negotiation expert
Repeat clients
Single-family homes
Townhouses
Ariel Renee Guzman 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 — 10 in the past two years. Ariel Renee Guzman is experienced with first-time homebuyers.
Works with: 40% sellers, 60% buyers
Total recent sales: 10
Local ranking by total sales: #149
State ranking by total sales: #5,626
Median days on market: 60 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.
Karen M Ohare
Colony Realty
Recent sales*
10
Local sales*
8
Price range*
$236K - $670K
Typical price*
$440,500
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 — 10 in the past two years. Karen M Ohare's experience includes sales involving HOAs and VA loans and military buyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 10
Local ranking by total sales: #182
State ranking by total sales: #6,313
Median days on market: 36 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.
Shane Bowman
Re/Max Roots
Recent sales*
11
Local sales*
9
Price range*
$162K - $515K
Typical price*
$346,850
Highlights
About
Repeat clients
First-time buyers
Single-family homes
Townhouses
Shane Bowman is a real estate agent who is primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 4 transactions over the past 12 months — 11 in the past two years. Shane Bowman's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Works with: 45% sellers, 55% buyers
Total recent sales: 11
Local ranking by total sales: #167
State ranking by total sales: #5,997
Median days on market: 34 days
Median sale-to-list ratio: 99%
License #: 0225244707 (VA, WV)
Are you Shane Bowman? 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*
$320,000
Highlights
About
Highly ratedFast sales
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
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 10 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: 40% sellers, 60% buyers
Total recent sales: 25
Local ranking by total sales: #70
State ranking by total sales: #3,277
Median days on market: 38 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.
Caroline W Barb
Jim Barb Realty, Inc.
Recent sales*
18
Local sales*
7
Price range*
$213K - $1.1M
Typical price*
$420,000
Highlights
About
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Caroline W Barb is a real estate agent who is primarily active in Washington, DC. They work with sellers and buyers and have closed at least 9 transactions over the past 12 months — 18 in the past two years. Caroline W Barb's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Works with: 56% sellers, 44% buyers
Total recent sales: 18
Local ranking by total sales: #193
State ranking by total sales: #6,651
Median days on market: 77 days
Median sale-to-list ratio: 99.5%
License #: 0225243462, 275102 (GA, VA)
Are you Caroline W Barb? Fill out this form to claim your profile or offer a correction.
Cynthia K Greenya
Keller Williams Realty
Recent sales*
30
Local sales*
11
Price range*
$160K - $1.4M
Typical price*
$427,000
Highlights
About
HOA experience
First-time buyers
Single-family homes
Townhouses
Cynthia K Greenya is a real estate agent who is primarily active in Washington, DC. They work with sellers and buyers and have closed at least 16 transactions over the past 12 months — 30 in the past two years. Cynthia K Greenya's experience includes sales involving HOAs, luxury homes, and first-time homebuyers.
Works with: 63% sellers, 37% buyers
Total recent sales: 30
Local ranking by total sales: #126
State ranking by total sales: #4,870
Median days on market: 53 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.
Deborah Matthews
ERA Oakcrest Realty, Inc.
Recent sales*
59
Local sales*
38
Price range*
$185K - $930K
Typical price*
$400,000
Highlights
About
Top 10% 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 primarily active in Winchester, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 59 in the past two years. Deborah Matthews's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Works with: 61% sellers, 39% buyers
Total recent sales: 59
Local ranking by total sales: #18
State ranking by total sales: #916
Median days on market: 50 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.
Jeffrey W Konrady
Long & Foster
Recent sales*
25
Local sales*
17
Price range*
$180K - $931K
Typical price*
$399,000
Highlights
About
Military buyers
First-time buyers
Single-family homes
Townhouses
Jeffrey W Konrady 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. Jeffrey W Konrady's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Works with: 36% sellers, 64% buyers
Total recent sales: 25
Local ranking by total sales: #68
State ranking by total sales: #3,064
Median days on market: 56 days
Median sale-to-list ratio: 98%
License #: 0225207222 (VA, WV)
Office address: 480 W Jubal Early Dr #100, Winchester, VA 22601, USA
Are you Jeffrey W Konrady? Fill out this form to claim your profile or offer a correction.
Cara L Wilkins
MarketPlace REALTY
Recent sales*
15
Local sales*
9
Price range*
$194K - $810K
Typical price*
$402,074
Highlights
About
Offer strategy
Negotiation expert
First-time buyers
Senior living
Single-family homes
Townhouses
Cara L Wilkins 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 — 15 in the past two years. Cara L Wilkins's experience includes first-time homebuyers, properties in senior communities, and luxury homes.
Works with: 40% sellers, 60% buyers
Total recent sales: 15
Local ranking by total sales: #151
State ranking by total sales: #5,659
Median days on market: 48 days
Median sale-to-list ratio: 101%
License #: 0225065889 (VA)
Are you Cara L Wilkins? Fill out this form to claim your profile or offer a correction.
Barton Thomas Chasler
Realty ONE Group Old Towne
Recent sales*
14
Local sales*
13
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 12 transactions over the past 12 months — 14 in the past two years.
Works with: 57% sellers, 43% buyers
Total recent sales: 14
Local ranking by total sales: #94
State ranking by total sales: #4,159
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.
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 59 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 4.5 months of supply, meaning it would take about that long for all available homes to sell if no new listings were added. There were 654 homes for sale in Winchester in the last month. Sellers added 44 new listings, and 36 home sales closed in that time.
On average, properties spend 59 days on the market, and it takes 52 days for a home to go under contract.
Homes in Winchester, Virginia are selling for less on average compared to the previous month. More sellers reduced their listing price this month compared to last month.
47 homes dropped in price this month. That's around 7% of all homes on the market, compared to the 6.51% of listings that lowered prices the month before.
The median home in Winchester, Virginia ultimately sells for its original list price: $398,492.
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 922,600 data points for 306 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.
