The best way to find top real estate agents in Chester Gap, VA

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Chester Gap, VA real estate

Compare top Chester Gap real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 2025. *


* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

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Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“Kim is hands down the best realtor I have worked with. She is patient, kind, honest and detail orientated. She is an excellent negotiator and treats her clients like family. I highly recommend Kim Chamberlain to ANYONE who is either buying a new home or selling an existing home. She is the BEST!”

Dave A. · Dumfries, VA

Photo of Kim Chamberlain
eXp Realty
“She is very personable and professional. She guided me through a very tough decision. I appreciated her commitment to help me reach my goal.”

Taryn Weaver · Bealeton, VA

Photo of TC Cooksley
1Simple Realty
“Outstanding and professional service.”

Jermaine · Fredericksburg, VA

Photo of Nick Hill
Century 21 New Millenium
“Marc is a consummate professional. He also CARES about people and that is something missing in a lot of business relationships these days. He is attentive to the smallest of details and his knowledge helped guide us through the process of buying and selling our homes.”

Kathleen Graeve · Fairfax, VA

Photo of Marc Massis
Century 21 New Millennium
“Kat is the person every seller wants on his/her team as a seller's agent - as was our case. But I wouldn't hesitate to have her as a buyer's agent either based on the clear planning and strategies. Thank you again, Kat.”

Rey and Linda · Winchester, VA

Photo of Katherine Wetzel
Century 21 Redwood Realty
“Emilie was amazing to work with. She went above and beyond to make sure we got the perfect home.”

Missy B. · Ruther Glen, VA

Photo of Emilie Donald
Blue and Gray Realty LLC
“We are so glad we worked with Agent Pronto and were referred to our realtor, Josh Brown. It was a great experience. Mr. Brown provided us with professional level service and we ended up selling quickly and above asking price!”

Theresa S. · Woodstock, VA

Photo of Josh Brown
Funkhouser Real Estate Group
“We could not have made a better selection of Broker for us! The purchase was so easy you would not have even thought you were buying a house! Brandon is extremely knowledgeable and very comfortable to be around. Brandon’s hard work and dedication helped us achieve a purchase multiple people told us wasn’t possible! Truly like buying from your best pal.”

Logan · VA

Photo of The Bennett Team
Weichert Realtors Blue Ribbon
“Chad Kimble patiently showed us many properties over several months. Chad was constructive with his comments and suggestions, in addition to having a great personality. The chemistry clicked between us. Thank you, Chad! ”

Wayne S. · Woodstock, VA

Photo of Chad Kimble
Funkhouser Real Estate Group
“You were prompt and friendly. Nancy Shiley is the best home agent we have ever encountered. She is amazing. Went out of her way many times to find us just the right home. She is a gem.”

Nancy K. · Winchester, VA

Photo of Nancy Shiley
Samson Properties

Chester Gap real estate Market Report.

Information and statistics on the latest trends in the Chester Gap real estate market, updated for October 2025. *

Chester Gap, VA real estate
27
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Chester Gap has to offer.

Chester Gap offers residents a charming blend of scenic natural beauty and close-knit community living, making it a wonderful place to experience peaceful, outdoor-oriented lifestyles.

Chester Gap delivers big-sky mountain views with everyday convenience, set right where quiet country roads meet bucket-list adventure. Minutes from the ridgeline, residents can cruise the iconic Skyline Drive and roam the waterfalls, overlooks, and backcountry trails of Shenandoah National Park, or lace up for a day on the Appalachian Trail, which passes just south of town. When it’s time to run errands or meet friends, you’re a quick drive to the friendly storefronts and trailhead energy of Front Royal or the eateries and galleries of Sperryville.

Families value the small-town attention in Rappahannock County and nearby Warren County, with academics anchored by the community-focused programs at Rappahannock County Public Schools. Weekend plans come easy: float or paddle at Shenandoah River State Park, watch the seasons turn across high meadows, then return to starlit skies that make backyard astronomy a simple pleasure. Local farms, orchards, and wineries add flavor to the calendar with markets and tastings, while outdoor outfitters keep hikers, anglers, and cyclists geared up for the next outing.

Housing here spans rustic cabins, tidy cottages, and newer builds on acreage, offering room to breathe and space for gardens, gear, and guests. Whether you’re eyeing a mountainside retreat or preparing to list a well-loved home, Agent Pronto can introduce you to a trusted local real estate agent to guide your next move with confidence.

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Chester Gap. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


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