Gwynn, VA Homes

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  /33

  $499,500

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  77 Bingo Blvd, Gwynn, VA 23066

  Storybook Coastal Cottage with Stunning Chesapeake Bay Views. Step into the pages of a classic seaside tale with this meticulously and thoughtfully renovated SEA CAPTAIN’S HOUSE, nestled in a private community on Gwynn’s Island. With sweeping views of the Chesapeake Bay, this timeless 1910 coastal cottage offers a peaceful escape from life’s daily hustle. Every detail of this 3-bedroom home

  Neena Rodgers Pearls of the Chesapeake LLC

  77 Bingo Blvd, Gwynn, VA 23066
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  /42

  $361,400 Sold Mar 11, 2025

  • 1,588 Sq Ft
  • $228/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1918

  2416 Old Ferry Rd, Hudgins, VA 23076

  Welcome to The White House at Island Farms on Historic Gwynn's Island. One of the 22 original homes built on the island, this craftsman farmhouse has all of the modern ammenities one could want waiting inside and out without losing any of its old world charm. The front porch is completely enclosed and greets you with just a clean, inviting entry and space to watch the time go by. There are so

  John Lewis The Real Estate Group, LLC

  2416 Old Ferry Rd, Hudgins, VA 23076
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  /17

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,968 Sq Ft

  29 S Bay Haven Dr, Gwynn, VA 23066

  29 S Bay Haven Dr, Gwynn, VA 23066
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  /69

  $3,299,000

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft

  1071 Gum Thicket Rd, Gwynn, VA 23066

  ESCAPE to your personal island paradise built for climate resiliency and protection-- a mere 60 minutes from Williamsburg and Yorktown, 60-90 minutes from nearby Richmond, Norfolk, Newport News and Virginia Beach and just 3 hours from the DC-area. Enjoy one of the most picturesque islands on the Chesapeake Bay and enjoy a dreamy, carefree lifestyle filled with nature and activities for all

  Nelson Marban Washington Fine Properties, LLC

  1071 Gum Thicket Rd, Gwynn, VA 23066
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  /32

  $298,500 Sold Feb 21, 2025

  • 1,078 Sq Ft
  • $277/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1995

  377 Callis Wharf Rd Unit 311, Mathews County, VA 23064

  Imagine feeling those relaxed vacation vibes all year long! Here is your chance to own a 2 bedroom, 2 full bathroom waterfront condo on Gwynn's Island in beautiful Mathews county! Be a part of this friendly vibrant community and enjoy the glorious view of Milford Haven throughout the seasons. This 2nd floor/top floor unit is being sold fully furnished so you can move in and start living right

  Bill Watson Boyd Realty Group

  377 Callis Wharf Rd Unit 311, Mathews County, VA 23064
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  /23

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft

  377 Callis Wharf Rd, Mathews County, VA 23064

  377 Callis Wharf Rd, Mathews County, VA 23064
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  /49

  $699,000

  • 3 Beds
  • 3 Baths
  • 2,452 Sq Ft

  298 Old Ferry Rd, Grimstead, VA 23064

  Breathtaking waterview retreat on Gwynn’s Island featuring panoramic water views and spectacular sunsets. This meticulously renovated home offers luxury living with thoughtful high end upgrades throughout. Enjoy the 320 sq ft air-conditioned enclosed screen porch perfect for entertaining while overlooking the bay.Recent renovations include a stylish new gable roof, energy-efficient windows and

  Theresa Ashberry CENTURY 21 Nachman Realty

  298 Old Ferry Rd, Grimstead, VA 23064
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  /25

  $259,000 Sold Dec 11, 2024

  • 1,350 Sq Ft
  • $192/SF
  • 17 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1949

  586 S Bay Haven Dr, Gwynn, VA 23066

  This home lives large! Charming brick house Located just one block from Edwards Creek with water views from this beautiful property. Brand new septic system. Nestled in a wonderful waterfront neighborhood. Featuring recent luxury vinyl plank flooring, fresh paint, large eat in kitchen, open family room and sunroom for loads of living space. Two bedrooms with centrally located

  Peggy Long Long & Foster Real Estate

  586 S Bay Haven Dr, Gwynn, VA 23066
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  /28

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft

  377 Callis Wharf Rd Unit 303, Mathews County, VA 23064

  377 Callis Wharf Rd Unit 303, Mathews County, VA 23064
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  /42

  $549,950

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  143 Henry's Rd, Redart, VA 23076

  Unbelievable opportunity to own just under 2 acres of WATERFRONT property on the one and only Gwynn's Island! This incredible property features a really nice pier with a 10,000 lb. boat lift, deep clear water that can accommodate bigger boats, a small gravel boat ramp, and outstanding water views. The home has been recently updated and features 4 bedrooms and two full baths. There is a gigantic

  Robbie Tyler ERA Woody Hogg & Assoc

  143 Henry's Rd, Redart, VA 23076
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  /43

  $860,000 Sold Nov 29, 2024

  • 3,360 Sq Ft
  • $256/SF
  • 36 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1977

  1074 Gum Thicket Rd, Gwynn, VA 23066

  "Captains Home" - this Beautiful Well appointed Colonial Brick Home is built like a Fortress by Original Local Builder James Robins, Sr.. This home has a stunning design at Foyer and Formal Living room w/ a Beautiful Staircase welcome feature. The home features ceramic tile and white oak solid wood floors. The ample kitchen that overlooks he water as well as the Dining Room and the Primary

  Deborah Morgan Morgan & Edwards Real Estate

  1074 Gum Thicket Rd, Gwynn, VA 23066
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  /30

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft

  319 E Shore Dr, Mathews, VA 23066

  319 E Shore Dr, Mathews, VA 23066
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  /2

  $47,500

  • Land
  • 1.29 Acres
  • $36,822 per Acre

  001 Risby Town Rd, Gwynn, VA 23066

  1.29 Acres Lot in desirable neighborhood at lovely Gwynn's Island VA . The Seller is currently having the lot perked for a 3 Bedroom home and will convey a Septic Certification Letter from Mathews Health Department. Other studies that may be necessary the Buyer is able to do with the Sellers permission. Come and live on an Island! Gwynn's Island !!! GIS Map attached.

  Deborah Morgan Morgan & Edwards Real Estate

  001 Risby Town Rd, Gwynn, VA 23066
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  /25

  $326,000 Sold Sep 03, 2024

  • 2,832 Sq Ft
  • $115/SF
  • 10 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1906

  2292 Old Ferry Rd, Gwynn, VA 23066

  1906 Sea Captains' Home on 3 and half acres located on Gwynn's Island. Original stain glass doors are the excellent way to greet family and friends. Open foyer leads to a front parlor, den, extra-large kitchen and dining room, oversized 1st floor primary bedroom complete with primary bath. Addition 1st floor 3-piece bath, full laundry room and mud room with extra closet space. 3 bedrooms with a

  Donna Erwin Erwin Realty

  2292 Old Ferry Rd, Gwynn, VA 23066
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  /17

  Est $130,690 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  55 Cherry Dr, Gwynn, VA 23076

  55 Cherry Dr, Gwynn, VA 23076
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  /48

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  2289 Old Ferry Rd, Gwynn, VA 23066

  Timeless modern farmhouse located on beautiful Gwynn's Island. Privately situated on nearly an acre of land just around the corner from the Chesapeake Bay. First floor offers an inviting open family room and a home office / playroom and a full bath. There is a bright open kitchen with stainless appliances, large walk-in pantry, dining area and walk out to a concrete patio for grilling.

  Peggy Long Long & Foster Real Estate

  2289 Old Ferry Rd, Gwynn, VA 23066
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  /19

  $349,000 Sold Aug 07, 2024

  • Land
  • 1.52 Acres
  • $229,003 per Acre

  • 33 Days On Market

  000 Hunley's Cove Ln, Mathews, VA 23066

  Stunning, wide water views of Queens Creek and 230 feet of pristine shoreline. This gorgeous, LEVEL lot with large CLEARED area is ready for building the home of your dreams. Septic system is installed and high-speed Internet available. Located on quiet, private cul-de-sac and NOT in flood zone. Good water depth and quick access to the Piankatank River and the Chesapeake Bay. Fabulous location

  Neena Rodgers Pearls of the Chesapeake LLC

  000 Hunley's Cove Ln, Mathews, VA 23066
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  186 Old Cherry Pt Rd, Gwynn, VA 23066

  186 Old Cherry Pt Rd, Gwynn, VA 23066
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  /69

  $3,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft

  1071 Gum Thicket Rd, Gwynn, VA 23066

  ESCAPE to your personal island paradise built for climate resiliency and protection-- a mere 60 minutes from Williamsburg and Yorktown, 60-90 minutes from nearby Richmond, Norfolk, Newport News and Virginia Beach and just 3 hours from the DC-area. Enjoy one of the most picturesque islands on the Chesapeake Bay and enjoy a dreamy, carefree lifestyle filled with nature and activities for all

  Nelson Marban Washington Fine Properties, LLC

  1071 Gum Thicket Rd, Gwynn, VA 23066
• 

  

  /19

  $349,000 Sold Aug 06, 2024

  • Land
  • 1.52 Acres
  • $229,605 per Acre

  • 33 Days On Market

  000 Hunleys Cove Ln, Gwynn, VA 23066

  Stunning, wide water views of Queens Creek and 230 feet of pristine shoreline. This gorgeous, LEVEL lot with large CLEARED area is ready for building the home of your dreams. Septic system is installed and high-speed Internet available. Located on quiet, private cul-de-sac and NOT in flood zone. Good water depth and quick access to the Piankatank River and the Chesapeake Bay. Fabulous location

  Neena Rodgers Isabell K. Horsley R. E., Ltd.

  000 Hunleys Cove Ln, Gwynn, VA 23066
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  186 Cherry Dr, Hudgins, VA 23076

  186 Cherry Dr, Hudgins, VA 23076
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  /2

  $49,900

  • Land
  • 1.00 Acre
  • $49,900 per Acre

  001 N Bay Haven Dr, Gwynn, VA 23066

  Beautiful lot on lovely Gwynn's Island. Build your home here ! This property Perks for a 4 Bedroom septic. Details are forthcoming on documentation of the perk. Wetlands delineation done! See survey and Wetlands attachments to the listing. Enjoy the Island Life. Live on an Island , Gwynn's Island. Boat Ramp to Chesapeake Bay nearby. Call to see this one!

  Deborah Morgan Morgan & Edwards Real Estate

  001 N Bay Haven Dr, Gwynn, VA 23066
• 

  $250,000 Sold Aug 02, 2024

  • 1,172 Sq Ft
  • $213/SF
  • 28 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1912

  2442 Old Ferry Rd, Mathews, VA 23066

  As you cross the bridge into Gwynn's Island, nestled along the Chesapeake Bay, feel the peace and serenity leaving the mainland and travel back to a time when life was simple and neighbors were friends. Full of old world charm, this waterfront community hosts several events each year including the Islander Regatta and the Gwynn's Island Festival. Then of course, The Chesapeake Bay is only 1/2

  John Lewis The Real Estate Group

  2442 Old Ferry Rd, Mathews, VA 23066
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  /4

  Not Listed For Sale

  Route 633 Old Ferry Rd, Gwynn, VA 23064

  Route 633 Old Ferry Rd, Gwynn, VA 23064
• 

  /2

  $47,500

  • Land
  • 1.29 Acres
  • $36,822 per Acre

  1+AC Risby Town Rd, Gwynn, VA 23066

  1.29 Acres Lot for rural mostly private living at lovely Gwynn's Island VA . The Seller is currently having the lot perked for a 4 Bedroom home (soil work in hand and study will convey)Other studies that may be necessary the Buyer is able to do with the Sellers permission. Come and live on an Island! Gwynn's Island !!! GIS Map attached.

  Deborah Morgan Morgan & Edwards Real Estate LLC

  1+AC Risby Town Rd, Gwynn, VA 23066
• 

  $145,000 Sold Aug 02, 2024

  • 1,312 Sq Ft
  • $111/SF
  • 52 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1910

  142 S Bay Haven Dr, Gwynn, VA 23066

  Welcome to 142 South Bay Haven Drive on the beautiful Gwynn's Island. This 1910 home was remodeled in 1983. The kitchen has new cabinets with plenty of storage. Very nice utility room with washer and dryer. The two main rooms downstairs are extra large and can be turned into what your heart desires. Two bedrooms upstairs with a small room which can be turned into an upstairs bathroom. Large front

  Deborah Morgan Morgan & Edwards Real Estate LLC

  142 S Bay Haven Dr, Gwynn, VA 23066
• 

  

  /17

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  132 Gum Thicket Rd, Mathews County, VA 23066

  132 Gum Thicket Rd, Mathews County, VA 23066
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  /50

  $253,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  417 Gwynnsville Rd, Hudgins, VA 23076

  417 Gwynnsville Rd is a sunny and surprisingly spacious 2-bed, 1-bath rancher on sought-after Gwynn’s Island. Don’t be fooled by the square footage—it lives larger than it looks! Everyone who visits is amazed at how open, light-filled, and roomy it feels. The vintage-inspired kitchen features turquoise cabinets with slide-out shelving, an enameled cast iron sink, and a painted beadboard ceiling.

  Raquel Ott Real Broker, LLC

  417 Gwynnsville Rd, Hudgins, VA 23076
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  /2

  $25,000 Sold Jun 19, 2024

  • Land
  • 1.00 Acre
  • $25,000 per Acre

  • 17 Days On Market

  1ac N Bay Haven Dr, Gwynn, VA 23066

  Affordable building lot on amazing Gwynns Island. Live the island life. State public boat ramp nearby. Appealing building lot with over an acre. Walk to post office, church, & to the water! Soil work has been done in the past to support a 3 bedroom septic!

  Deborah Morgan Morgan & Edwards Real Estate

  1ac N Bay Haven Dr, Gwynn, VA 23066
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  /48

  Est $726,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  790 Gum Thicket Rd, Mathews County, VA 23066

  790 Gum Thicket Rd, Mathews County, VA 23066
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  /47

  $255,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,253 Sq Ft

  1697 Old Ferry Rd, Redart, VA 23076

  A charming 1920's Fisherman's Cottage on sought after Gwynn's Island on 1.10 acres. Life is simple on the Island, with friends and neighbors enjoying all the Island has to offer- Public boat ramp and pier on Milford Haven & Chesapeake Bay within 1.5 miles of this home. This home offers original moldings and character that we all love. There are 2 bedrooms & 1.5 baths with a large living room,

  Renee Edwards Morgan & Edwards Real Estate

  1697 Old Ferry Rd, Redart, VA 23076
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  /17

  Est $648,260 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,850 Sq Ft

  83 Island Dr, Gwynn, VA 23066

  83 Island Dr, Gwynn, VA 23066
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  /41

  $625,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,489 Sq Ft

  60 Edwards Landing Rd, Gwynn, VA 23066

  Timeless Waterfront Treasure! Charming historic farmhouse located on Edwards Landing is a perfect family home with every modern convenience. Enjoy boating, fishing, crabbing and endless water views throughout. Tremendous Gwynn's Island location with easy access to the hole in the wall by boat and downtown Mathews is just a short drive. Home features an updated kitchen, large first floor

  Peggy Long Long & Foster Real Estate

  60 Edwards Landing Rd, Gwynn, VA 23066
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  /39

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,856 Sq Ft

  346 Gwynnsville Rd, Gwynn, VA 23066

  346 Gwynnsville Rd, Gwynn, VA 23066
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  /2

  Not Listed For Sale

  Lot 4 S Bay Haven Dr, Gwynn, VA 23066

  Lot 4 S Bay Haven Dr, Gwynn, VA 23066
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,048 Sq Ft

  127 Henrys Rd, Gwynn, VA 23066

  127 Henrys Rd, Gwynn, VA 23066
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  /48

  Est $463,414 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,659 Sq Ft

  14 Triangle Rd, Gwynn, VA 23066

  14 Triangle Rd, Gwynn, VA 23066
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  /3

  Not Listed For Sale

  17.8 AC Cherry Point Rd, Mathews, VA 23066

  17.8 AC Cherry Point Rd, Mathews, VA 23066
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  /2

  Not Listed For Sale

  17.8AC Cherry Point Rd, Gwynn, VA 23066

  17.8AC Cherry Point Rd, Gwynn, VA 23066
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  /31

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,336 Sq Ft

  506 Old Ferry Rd, Grimstead, VA 23064

  506 Old Ferry Rd, Grimstead, VA 23064

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