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Updated October 13, 2025
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 294 real estate agents in Winchester, VA to identify the best of the best. These are the top-rated agents 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 (October 2025 rankings)
Top 1% local
Top 1% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
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 73 transactions over the past 12 months — 143 in the past two years. Daniel J Whitacre's experience includes luxury homes, first-time homebuyers, and properties in senior communities.
Top 1% local
Top 1% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
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 88 transactions over the past 12 months — 150 in the past two years. Sheila R Pack's experience includes sales involving HOAs, properties in senior communities, and luxury homes.
Top 1% local
Top 1% Virginia
Listing agent
Buyers agent
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 54 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 properties in senior communities.
Top 5% local
Top 1% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Manufactured homes
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 47 transactions over the past 12 months — 103 in the past two years. Leslie A Webb's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Top 1% local
Top 1% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Multi-family homes
Vacant land
Condos
David K Spence is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 38 transactions over the past 12 months — 93 in the past two years. David K Spence's experience includes first-time homebuyers, sales involving HOAs, and properties in senior communities.
Listing agent
Buyers agent
36+ years experience
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Manufactured homes
Sheila G Judy is a real estate agent who is active in Winchester, VA. Sheila G Judy has worked in real estate for over 36 years. They work with sellers and buyers and have closed at least 7 transactions over the past 12 months — 22 in the past two years. Sheila G Judy's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Top 5% local
Top 5% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
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 37 transactions over the past 12 months — 62 in the past two years. Lisa M Cox's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Top 10% local
Top 5% Virginia
Offer strategy
Negotiation expert
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
First-time buyers
Senior living
Single-family homes
Townhouses
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 23 transactions over the past 12 months — 45 in the past two years. Mark S Francis's experience includes sales involving HOAs, luxury homes, and properties in senior communities.
Top 10% local
Top 10% Virginia
Listing agent
Buyers agent
Neighborhood expert
Military buyers
First-time buyers
Senior living
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 21 transactions over the past 12 months — 40 in the past two years. Jeanne Mezzatesta's experience includes first-time homebuyers, VA loans and military buyers, and properties in senior communities.
Top 10% local
Top 5% Virginia
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
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 40 transactions over the past 12 months — 72 in the past two years. Roxanna D Grimes's experience includes sales involving HOAs, first-time homebuyers, and properties in senior communities.
Top 10% local
Top 5% VirginiaFast sales
Listing agent
Buyers agent
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 25 transactions over the past 12 months — 51 in the past two years. Anna Mari Fox's experience includes first-time homebuyers and sales involving HOAs.
Top 10% Virginia
Offer strategy
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
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 13 transactions over the past 12 months — 36 in the past two years. Stephanie Ryall's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Top 5% local
Top 1% Virginia
Listing agent
Buyers agent
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 43 transactions over the past 12 months — 77 in the past two years. Bradley Comstock's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Top 10% Virginia
Listing agent
Buyers agent
HOA experience
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 22 transactions over the past 12 months — 48 in the past two years. Julie D Shiley's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Top 10% Virginia
Listing agent
Buyers agent
19+ years experience
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Condos
Townhouses
Sergio A Vitela is a real estate agent who is active in Washington, DC. Sergio A Vitela has worked in real estate for over 19 years. They work with sellers and buyers and have closed at least 15 transactions over the past 12 months — 41 in the past two years. Sergio A Vitela's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Top 5% local
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
Luxury homes
First-time buyers
Single-family 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 28 transactions over the past 12 months — 47 in the past two years. Keenan L Shanholtz's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Top 10% Virginia
Listing agent
Buyers agent
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 — 41 in the past two years. Matthew Michael Kilmer's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Fast sales
Listing agent
Buyers agent
Senior living
Single-family homes
Townhouses
Stuart A Wolk is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 5 transactions over the past 12 months — 17 in the past two years. Stuart A Wolk's experience includes properties in senior communities, luxury homes, and sales involving HOAs.
Top 10% local
Top 5% VirginiaFast sales
Listing agent
Buyers agent
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 20 transactions over the past 12 months — 44 in the past two years. Lori Fountain Bales's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Top 10% Virginia
Offer strategy
Negotiation expert
Listing agent
Buyers agent
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 — 27 in the past two years. Erika D De Azagra's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Top 10% Virginia
Listing agent
Buyers agent
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Manufactured 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 19 transactions over the past 12 months — 39 in the past two years. Kristen Kerns's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Top 10% local
Top 5% Virginia
Listing agent
Buyers agent
Repeat clients
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
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 30 transactions over the past 12 months — 59 in the past two years. Traci J Shoberg's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Listing agent
Buyers agent
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 16 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.
Negotiation expert
Listing agent
Buyers agent
Repeat clients
First-time buyers
Senior living
Single-family homes
Townhouses
Manufactured homes
Condos
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 6 transactions over the past 12 months — 16 in the past two years. Cara L Wilkins's experience includes first-time homebuyers, properties in senior communities, and luxury homes.
Pricing strategy
Negotiation expert
Listing agent
Buyers agent
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Stacey L Mullins 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. Stacey L Mullins's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Top 10% VirginiaFast sales
Listing agent
Buyers agent
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 24 transactions over the past 12 months — 39 in the past two years. Julie M Teets's experience includes luxury homes, sales involving HOAs, and VA loans and military buyers.
Jaclyn Fleet 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 — 14 in the past two years. Jaclyn Fleet is experienced with first-time homebuyers.
Top 5% local
Top 5% VirginiaFast sales
Listing agent
Buyers agent
Neighborhood expert
Repeat clients
HOA experience
Senior living
Single-family homes
Townhouses
Multi-family homes
Manufactured homes
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 24 transactions over the past 12 months — 61 in the past two years. Paul J Gallagher Jr's experience includes properties in senior communities, sales involving HOAs, and luxury homes.
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 11 transactions over the past 12 months — 26 in the past two years. Jeffrey W Konrady's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Top 10% VirginiaFast sales
Listing agent
Buyers agent
Repeat clients
HOA experience
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 15 transactions over the past 12 months — 41 in the past two years. Nicole Panos Lewis's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Lillian M Triplett 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 — 27 in the past two years. Lillian M Triplett's experience includes first-time homebuyers and VA loans and military buyers.
Top 5% Virginia
Listing agent
Buyers agent
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 26 transactions over the past 12 months — 47 in the past two years. Michele L Gibson's experience includes luxury homes, first-time homebuyers, and sales involving HOAs.
Listing agent
Buyers agent
Repeat clients
First-time buyers
Senior living
Single-family homes
Townhouses
Commercial properties
Dorothy Vance is a real estate agent who is active in Hagerstown, MD. They work with sellers and buyers and have closed at least 6 transactions over the past 12 months — 14 in the past two years. Dorothy Vance's experience includes first-time homebuyers, properties in senior communities, and sales involving HOAs.
Fast sales
Listing agent
Buyers agent
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 12 transactions over the past 12 months — 24 in the past two years. Katherine Landi Jordan's experience includes sales involving HOAs, first-time homebuyers, and properties in senior communities.
Top 5% local
Listing agent
Buyers agent
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 23 transactions over the past 12 months — 47 in the past two years. Katherine Jane Nazelrod's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Listing agent
Buyers agent
HOA experience
Military buyers
Single-family homes
Townhouses
Liz Owings 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 — 23 in the past two years. Liz Owings's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Fast sales
Offer strategy
Listing agent
Buyers agent
HOA experience
First-time buyers
Senior living
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 12 transactions over the past 12 months — 24 in the past two years. Jodi Costello's experience includes first-time homebuyers, sales involving HOAs, and properties in senior communities.
Listing agent
Buyers agent
Single-family homes
Townhouses
Michael Lawson Teets 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 — 9 in the past two years. Michael Lawson Teets's experience includes sales involving HOAs and properties in senior communities.
Listing agent
Buyers agent
Neighborhood expert
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 — 24 in the past two years. Caroline W Barb's experience includes first-time homebuyers, sales involving HOAs, and VA loans and military buyers.
Top 10% Virginia
Listing agent
Buyers agent
HOA experience
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Vacant land
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 15 transactions over the past 12 months — 29 in the past two years. Wendy S Conner's experience includes sales involving HOAs, properties in senior communities, and VA loans and military buyers.
Listing agent
Buyers agent
HOA experience
First-time buyers
Single-family homes
Townhouses
James W King Jr 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 — 30 in the past two years. James W King Jr's experience includes sales involving HOAs, first-time homebuyers, and luxury homes.
Top 10% local
Top 10% Virginia
Listing agent
Buyers agent
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 18 transactions over the past 12 months — 34 in the past two years. Kaitlyn Behr's experience includes sales involving HOAs, first-time homebuyers, and properties in senior communities.
Listing agent
Buyers agent
Single-family homes
Townhouses
Ed Butler 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 — 10 in the past two years. Ed Butler's experience includes sales involving HOAs, VA loans and military buyers, and first-time homebuyers.
Top 5% local
Top 5% VirginiaFast sales
Listing agent
Buyers agent
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Commercial properties
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 — 54 in the past two years. Deborah Matthews's experience includes first-time homebuyers, sales involving HOAs, and luxury homes.
Listing agent
Buyers agent
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Sylvia R Stoneberger 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 — 12 in the past two years. Sylvia R Stoneberger is experienced with first-time homebuyers.
Listing agent
Buyers agent
First-time buyers
Single-family homes
Condos
Elizabeth A Flood 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 — 13 in the past two years. Elizabeth A Flood is experienced with first-time homebuyers.
Natalie J Langford 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 — 24 in the past two years. Natalie J Langford's experience includes first-time homebuyers, luxury homes, and sales involving HOAs.
Fast sales
Listing agent
Buyers agent
Repeat clients
HOA experience
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Susan Susan Raburn 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 — 21 in the past two years. Susan Susan Raburn's experience includes first-time homebuyers and sales involving HOAs.
Listing agent
Buyers agent
Repeat clients
HOA experience
Military buyers
First-time buyers
Single-family homes
Townhouses
Commercial properties
Kristin Evans Crosby 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. Kristin Evans Crosby's experience includes sales involving HOAs, first-time homebuyers, and VA loans and military buyers.
Listing agent
Buyers agent
HOA experience
Single-family homes
Townhouses
Kerry Elizabeth Wysong is a real estate agent who is active in Winchester, VA. They work with sellers and buyers and have closed at least 5 transactions over the past 12 months — 8 in the past two years. Kerry Elizabeth Wysong's experience includes sales involving HOAs and properties in senior communities.
Works with: 38% sellers, 63% buyers
Total recent sales: 8
Local ranking by total sales: #234
State ranking by total sales: #11,227
Median days on market: 17 days
Median sale-to-list ratio: 100%
License #: WVS230303034 (WV, VA)
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 23 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 44 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.
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.
How we research and evaluate top real estate agents 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 900,900 data points for 294 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 in Winchester, Virginia and make it easier to compare your options.
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.
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