Find Top Real Estate Agents in Chesapeake, Virginia
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Updated November 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 Chesapeake, Virginia close more deals, negotiate better prices, and move homes faster than their peers.
We analyzed transactions and performance metrics for 719 real estate agents in Chesapeake, VA to identify the best of the best. These are the top-rated agents in Chesapeake 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 Chesapeake — 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.
Chesapeake, VA top real estate agents (November 2025 rankings)
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Top 1% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Vacant land
Condos
Betsy Thompson is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 134 transactions over the past 12 months — 230 in the past two years. Betsy Thompson's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Top 1% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Multi-family homes
Michael Daugherty is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 163 transactions over the past 12 months — 286 in the past two years. Michael Daugherty's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 1% local
Negotiation expert
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Multi-family homes
Bethany White is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 131 transactions over the past 12 months — 255 in the past two years. Bethany White's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Listing specialist
22+ years experience
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Dawn Crocker is a real estate agent who is active in Virginia Beach, VA. Dawn Crocker has worked in real estate for over 22 years. They work with sellers and buyers and have closed at least 17 transactions over the past 12 months — 39 in the past two years. Dawn Crocker's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
21+ years experience
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Gina Woodward is a real estate agent who is active in Virginia Beach, VA. Gina Woodward has worked in real estate for over 21 years. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 39 in the past two years. Gina Woodward's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Top 5% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Cole Hart is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 41 transactions over the past 12 months — 75 in the past two years. Cole Hart's experience includes luxury homes, first-time homebuyers, and VA loans and military buyers.
Top 5% local
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Daniel Patton is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 46 transactions over the past 12 months — 102 in the past two years. Daniel Patton's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Pricing strategy
Offer strategy
Negotiation expert
12+ years experience
Repeat clients
First-time buyers
Single-family homes
Townhouses
Condos
Vacant land
Multi-family homes
Shannon Paschall is a real estate agent who is active in Virginia Beach, VA. Shannon Paschall has worked in real estate for over 12 years. They work with sellers and buyers and have closed at least 30 transactions over the past 12 months — 61 in the past two years. Shannon Paschall's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Top 10% local
Pricing strategyFast sales
Negotiation expert
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Multi-family homes
Condos
Nikki Lori Johnsonpyle is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 48 transactions over the past 12 months — 89 in the past two years. Nikki Lori Johnsonpyle's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Top 1% localBuyer specialist
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Commercial properties
Matthew Salway is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 129 transactions over the past 12 months — 229 in the past two years. Matthew Salway's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 5% local
Pricing strategyFast sales
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Racheal Pridgen is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 31 transactions over the past 12 months — 60 in the past two years. Racheal Pridgen's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 10% local
Offer strategy
Negotiation expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Vacant land
Brenda Williams is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 44 in the past two years. Brenda Williams's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Top 5% local
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Anna Marie Staylor is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 49 transactions over the past 12 months — 92 in the past two years. Anna Marie Staylor's experience includes VA loans and military buyers, luxury homes, and properties in senior communities.
Top 10% local
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Tom Milan is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 31 transactions over the past 12 months — 64 in the past two years. Tom Milan's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Fast sales
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Kesha Wilkeyprim is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 13 transactions over the past 12 months — 27 in the past two years. Kesha Wilkeyprim's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Top 10% local
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Madison Mason is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 48 transactions over the past 12 months — 84 in the past two years. Madison Mason's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Fast sales
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Debbie Woolard is a real estate agent who is active in Virginia Beach, 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. Debbie Woolard's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Dusty Thayer is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 14 transactions over the past 12 months — 24 in the past two years. Dusty Thayer's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 5% localFast sales
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Manufactured homes
Taylor Lennox Bagnick is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 59 transactions over the past 12 months — 115 in the past two years. Taylor Lennox Bagnick's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Pricing strategyFast sales
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
Christine Cahoon is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 33 transactions over the past 12 months — 69 in the past two years. Christine Cahoon's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Natalie Carrier is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 40 transactions over the past 12 months — 44 in the past two years. Natalie Carrier's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Condos
Vacant land
Manufactured homes
Michael Amory is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 62 in the past two years. Michael Amory's experience includes luxury homes and first-time homebuyers.
Top 10% local
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Kim Elliot is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 28 transactions over the past 12 months — 64 in the past two years. Kim Elliot's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Top 10% local
Offer strategy
Negotiation expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Eddie Gerardoferrer is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 55 transactions over the past 12 months — 86 in the past two years. Eddie Gerardoferrer's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 5% local
Negotiation expert
Neighborhood expert
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Allen Boone is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 38 transactions over the past 12 months — 82 in the past two years. Allen Boone's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Top 10% local
Neighborhood expert
Repeat clients
First-time buyers
Single-family homes
Townhouses
Condos
Kim Stanley is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 21 transactions over the past 12 months — 33 in the past two years. Kim Stanley's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Fast sales
Offer strategy
Negotiation expert
Repeat clients
Military buyers
Single-family homes
Townhouses
Manufactured homes
Condos
Patricia Cohen is a real estate agent who is active in Virginia Beach, 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. Patricia Cohen's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Franklin Dalmida is a real estate agent who is active in Virginia Beach, 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. Franklin Dalmida's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Lana Cary is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 17 transactions over the past 12 months — 31 in the past two years. Lana Cary's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Negotiation expert
Repeat clients
Military buyers
Single-family homes
Townhouses
Condos
Chris Jenkins is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 40 in the past two years. Chris Jenkins's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Offer strategy
Negotiation expert
5+ years experience
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Heather Meyers is a real estate agent who is active in Virginia Beach, VA. Heather Meyers has worked in real estate for over 5 years. They work with sellers and buyers and have closed at least 26 transactions over the past 12 months — 51 in the past two years. Heather Meyers's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Pricing strategy
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Aneta Krauz is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 44 transactions over the past 12 months — 82 in the past two years. Aneta Krauz's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Repeat clients
Military buyers
Single-family homes
Townhouses
Justine Mahoney is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 13 transactions over the past 12 months — 20 in the past two years. Justine Mahoney's experience includes VA loans and military buyers and first-time homebuyers.
Top 10% local
Pricing strategyFast sales
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Melissa Humpert is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 34 in the past two years. Melissa Humpert's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Top 5% local
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Dani Brinson is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 31 transactions over the past 12 months — 58 in the past two years. Dani Brinson's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Top 10% localFast sales
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Andy Nelson is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 63 transactions over the past 12 months — 112 in the past two years. Andy Nelson's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Top 10% local
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Condos
John Conard is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 34 transactions over the past 12 months — 87 in the past two years. John Conard's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Top 5% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Senior living
Single-family homes
Townhouses
Steve Marable is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 29 transactions over the past 12 months — 60 in the past two years. Steve Marable's experience includes VA loans and military buyers, luxury homes, and first-time homebuyers.
Pricing strategyFast sales
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Zach Cheatham is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 40 transactions over the past 12 months — 64 in the past two years. Zach Cheatham's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Repeat clients
First-time buyers
Senior living
Single-family homes
Townhouses
Vacant land
Farra Sawyer is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 9 transactions over the past 12 months — 20 in the past two years. Farra Sawyer's experience includes first-time homebuyers, luxury homes, and properties in senior communities.
Top 5% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Manufactured homes
Kimberly Bedsole is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 27 transactions over the past 12 months — 50 in the past two years. Kimberly Bedsole's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Jordan Williams is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 25 transactions over the past 12 months — 56 in the past two years. Jordan Williams's experience includes first-time homebuyers, VA loans and military buyers, and luxury homes.
Top 1% local
Listing specialist
Neighborhood expert
Repeat clients
Military buyers
Single-family homes
Condos
Lisa Kyriakides is a real estate agent who is active in Chesapeake, VA. They primarily work with sellers and have closed at least 45 transactions over the past 12 months — 65 in the past two years. Lisa Kyriakides is experienced with VA loans and military buyers.
Top 10% local
Pricing strategy
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Frankie Ferguson is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 20 transactions over the past 12 months — 36 in the past two years. Frankie Ferguson's experience includes first-time homebuyers, luxury homes, and VA loans and military buyers.
Repeat clients
Luxury homes
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Condos
Colleen Kovach is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 24 transactions over the past 12 months — 49 in the past two years. Colleen Kovach's experience includes luxury homes, VA loans and military buyers, and first-time homebuyers.
Top 10% local
Offer strategy
Negotiation expert
Neighborhood expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Condos
Multi-family homes
Julian Rivera is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 57 transactions over the past 12 months — 112 in the past two years. Julian Rivera's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Dean Rolle Jr is a real estate agent who is active in Virginia Beach, 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. Dean Rolle Jr's experience includes first-time homebuyers and VA loans and military buyers.
Offer strategy
Negotiation expert
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Multi-family homes
Claudia Aristizabal is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 22 transactions over the past 12 months — 37 in the past two years. Claudia Aristizabal's experience includes first-time homebuyers, VA loans and military buyers, and investment properties.
Pricing strategy
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Amber Levinson is a real estate agent who is active in Virginia Beach, 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. Amber Levinson's experience includes VA loans and military buyers, first-time homebuyers, and luxury homes.
Repeat clients
Military buyers
First-time buyers
Single-family homes
Townhouses
Janette Woodruff is a real estate agent who is active in Virginia Beach, VA. They work with sellers and buyers and have closed at least 14 transactions over the past 12 months — 30 in the past two years. Janette Woodruff's experience includes first-time homebuyers and VA loans and military buyers.
Works with: 50% sellers, 50% buyers
Total recent sales: 30
Local ranking by total sales: #480
State ranking by total sales: #2,142
Median days on market: 32 days
Median sale-to-list ratio: 100%
What to know about top real estate agents in Chesapeake, VA
Top Chesapeake real estate agents combine deep, local expertise with higher-than-average performance. Here’s what that looks like in Chesapeake.
General
High transaction volume: Does more than 30 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 Chesapeake 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 Chesapeake is 43 days)
Buyers
Strong negotiator: The best buyer’s agents in Chesapeake 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 Chesapeake 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 Chesapeake 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 Chesapeake
Data sources
Our rankings are powered by real estate transaction data, internal research, and other publicly available sources. We compiled and analyzed over 2,775,700 data points for 719 real estate agents across Chesapeake, 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 Chesapeake, 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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