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Gloucester and Mathews Real Estate

Gloucester & Mathews County

Welcome home to Gloucester and Mathews County, an historic maritime paradise located on Virginia’s Middle Peninsula. Coastal living is the heart of this community located on the Chesapeake Bay.

Miles of waterfront sites and a well-preserved appreciation for the watermen community distinguish Mathews, one of the smallest of Virginia’s counties at 94 square miles.

Gloucester is as charming a place as you’ll find with a traditional downtown Main Street village that’s a slice right out of Norman Rockwell. Folks are friendly here, where it’s easy to fall in love with a simpler, slower pace of life (while boasting easy access to Richmond, the Virginia Peninsula and South Hampton Roads).

Every bit as significant as the water is the history found within Gloucester and Mathews County, which once housed the first English American colonists. Gloucester was once the capital of the Native American Powhatan Confederacy, and its most famous former citizen would surely be Pocahontas.


Painter Shelby Keefe works on painting at the Cocktails in the Garden event at Brent & Becky’s Bulbs Tuesday June 8, 2021.

You can’t miss the murals along Gloucester Main Street that pay homage to history, the water and daffodils, the first flower of Gloucester.

Speaking of daffodils, mark your calendar now for the annual Gloucester Daffodil Festival.

Don’t leave downtown without browsing at Arts on Main, a nonprofit community gallery that sells the wares of local artists.

Mathews County is a rich part of the Virginia Artisan Trail with Gloucester, Essex and Middlesex. Curate your own experience.

Mathews County hosts the Tour de Chesapeake, a three-day family bicycle and community event held in May. Mathews Market Days welcomes local and neighboring artists, craftsmen, musicians and performers for an annual event held on Labor Day weekend.

Bay School Community Arts Center is a nonprofit art gallery that offers more than 100 art classes, conducts arts outreach programming and showcases the best of local, regional and Virginia fine arts and crafts in its Art Speaks Gallery. The Poddery is a pottery lover’s dream with handmade stoneware and tiles for sale, many of them inspired by the Chesapeake Bay.

The building that is Gloucester Museum of History dates back to 1770. Walter Reed Birthplace in Gloucester County was built around 1825 and restored in 1927. Mathews Historical Museum invites you to travel through time.

Woodville School, one of the remaining Rosenwald Schools, is a testament to the community’s efforts to preserve the educational history of Gloucester’s African American students.

The remains of the Rosewell Plantation, among the nation’s most magnificent ruins, are worth a visit.

Revel in the history and encourage your guests to stay overnight at the Inn at Warner Hall, a bed-and-breakfast along the Severn River that belonged to George Washington’s great-great grandfather. The Inn at Tabb’s Creek is another waterfront getaway that offers a scrumptious homemade breakfast.

If you love the links, Gloucester and Mathews are within an hour of eight golf courses.


Crabbing with Chris Pritchett, his son Coleman and Wayne Taylor out of Port Haywood, Virginia Friday August 7, 2020.

Like seafood? Fill your belly at Olivia’s In The Village (try the chowder), you’ll love the fish tacos at York River Oyster Company and dine in or carry out at The Seafood Shack. Enjoy the best Thai in Virginia per Virginia Living Magazine’s annual awards at Bangkok Noi. Speaking of the best, you will not be disappointed at Scoot’s BBQ, another award winner for best barbecue in Virginia. Breakfast rocks at Howard-Dooley Café in Mathews. Savor shakes, ice cream, craft beer and All-American favorites at Richardson’s Café. If comfort food is for you, stop in at Lulu Birds Kitchen.

Drive, cycle or boat over to Hole in the Wall for fresh seafood, burgers and soups on Gwynn’s Island.

You bet there’s great pizza in these parts. Check out Southwind Pizza’s handmade hearth-baked pizza, it’s yummy at Anna’s Italian Pizza on Gloucester Main Street and Tony & Milena’s, which offers New York-style folded pizza and European pizza, is delish.

Enjoy homemade beer on tap at Gloucester Brewing Company just off Main Street. Pair award-winning wine with handmade chocolates at Zoll Vineyards, a farm-to-table winery right on the county line of Gloucester and Mathews counties.


Mathews Elementary, Thomas Hunter and Mathews High School comprise the Mathews County Public Schools. Eight schools make up Gloucester County Public Schools. Gloucester Montessori School and Ware Academy are the two private schools in Gloucester.

Virginia Peninsula Community College in nearby Hampton and Rappahannock Community College are two of 23 colleges in the Virginia Community College System.

Christopher Newport University, Hampton University, Old Dominion University and William and Mary are each located within a 90-minute drive.

William and Mary’s Virginia Institute of Marine Science is located at Gloucester Point.


Recently renovated Riverside Walter Reed Hospital in Gloucester includes state-of-the-art surgical services and a complete range of outpatient services. The recently expanded emergency department services nearly 22,000 patients per year.


Reconnect with the outdoors with 20 kayak launch points and ample natural beaches found throughout Gloucester and Mathews County.

Want to bird watch, hunt, fish and enjoy the outdoors on publicly accessible lands? Visit Virginia’s Coastal Wilds to explore.

Located in the southern part of Gloucester County along the York River, Machicomoco State Park highlights the culture and legacy of the Native Tribes of Virginia. You can park or hike at the park, rent a yurt, fish or take one of many seasonal classes. Beaverdam Park is a tranquil jewel with a freshwater lake, dedicated hiking trails, a fishing pier, boat access and a sizable playground.

Explore or picnic in the sand at Bethel Beach Natural Area Preserve, a birding haven and ideal for kite surfers thanks to its shallow and sandy surf. If you like to swim, Haven Beach has designated swimming areas and a sandy bottom pleasing to the feet. Bavon Beach is a private stretch of white sandy beaches and cottages, where you can seek out your own “Bay Window” — coastal views of the area’s unspoiled spots pretty enough to paint.

New Point Comfort Nature Preserve juts onto the Chesapeake Bay and habitat along the Atlantic Flyway for migrating birds.

Annuals events such as the Daffodil Festival in the spring and the Guinea Jubilee every fall draw thousands of visitors. The Gloucester Arts Festival is a monthlong celebration of arts, music and theater held every June.


Downtown Mathews, Virginia.

Find major grocery chains Walmart, Kroger and Food Lion. Kelsick Specialty Market is a one-stop shop for groceries and housemade entrees (locals love the Shepherd’s Pie) on Gloucester Main Street. The chef at Nuttall’s Store is a Johnson and Wales graduate who sources local ingredients and cooks them to perfection.

The shops along Gloucester Main Street are all locally owned with unique finds from The Silver Box, Up South and The Nurtury, a modern-day apothecary.

Find food, flowers and gifts at the Mathews Farmers Market held Saturdays from April through October on the Historic Courthouse Green.

Antique lovers will find treasures at Roane’s Antiques at the Cottage, Mermaid’s Crossing and Etc. Vintage

Grow a beautiful garden with the help of nationally renowned Brent & Becky’s Bulbs in Ware Neck.

Find historical gifts at Colonial Williamsburg and Merchants Square less than an hour away.


Major employers include Canon Environmental Technologies, Riverside Health System and Virginia Institute of Marine Science. Gloucester is home to Whitley’s Peanut Factory, a local staple for home-cooked Virginia peanuts and confections. International apparel company Peace Frogs is headquartered in Gloucester.

Both counties are less than 90 minutes from Richmond and within an hour of Newport News Shipbuilding. It’s close to Newport News/Williamsburg International Airport and Interstate 64.

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