Mathews, VA Homes

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  /50

  $3,299,000

  • 5 Beds
  • 4.5 Baths
  • 4,610 Sq Ft

  1071 Gum Thicket Rd, Gwynn, VA 23066

  Welcome to an extraordinary waterfront retreat on Gwynns Island, offering sweeping views across Milford Haven out to the Chesapeake Bay. This custom-designed residence, completed in 2008, is thoughtfully planned to blend elegant living with the natural beauty of its coastal surroundings. Nearly every room showcases a stunning water view and is filled with natural light, creating an atmosphere of

  

  Katie and David Dew

  IsaBell K. Horsley Real Estate

  (804) 808-1470

  1071 Gum Thicket Rd, Gwynn, VA 23066
• 

  $649,900 Sold Jul 25, 2025

  • 3,608 Sq Ft
  • $180/SF
  • 2 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2010

  78 Spirit Branch Rd, Gwynn, VA 23064

  Discover your dream retreat on Gwynns Island, with deep, protective water on Edwards Creek. This luxurious home is located in a no-flood zone and features two primary suites, a 5-car garage, and a spacious lot.The open-concept design boasts vaulted ceilings, a stone fireplace, and multiple French doors leading to a 10x50 covered verandah, great for entertaining. The gourmet kitchen

  Theresa Ashberry CENTURY 21 Nachman Realty

  78 Spirit Branch Rd, Gwynn, VA 23064
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  /12

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  2442 Old Ferry Rd, Mathews, VA 23066

  2442 Old Ferry Rd, Mathews, VA 23066
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  /27

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,001 Sq Ft

  936 Old Ferry Rd, Grimstead, VA 23064

  Subject to online sale ending August 7 at 3:00 PM. List price is the opening offer amount and may not reflect the final sales price. Property tour is scheduled for July 2nd at 2:00 PM. Seller is considering presale offers. This extraordinary 1.045-acre waterfront parcel represents a once-in-a-lifetime opportunity to secure premium Chesapeake Bay frontage on Virginia's coveted Gwynn’s Island—known

  

  Tim Dudley

  Dudley Auctions Inc

  (844) 771-0735

  936 Old Ferry Rd, Grimstead, VA 23064
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  /33

  $499,000 Sold Jul 02, 2025

  • 1,800 Sq Ft
  • $277/SF
  • 37 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1880

  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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  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,312 Sq Ft

  142 S Bay Haven Dr, Gwynn, VA 23066

  142 S Bay Haven Dr, Gwynn, VA 23066
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  /43

  $450,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  17 Mad Calf Ln, Gwynn, VA 23066

  The VIEWS - gorgeous northeast views out over the Bay! Watch the ships, the stars, the waves. Adorable 1940 2+BR cottage with unbelievable views from sweeping screen porch and side deck. Take in the sunrises and Bay breezes, enjoy quiet strolls and bike rides through quaint, quiet & historic Gwynn’s Island. Completely renovated 2013-15 with new wiring, plumbing, 3BR Clearstream septic, siding,

  Bernadette La Casse Isabell K. Horsley Real Estate

  17 Mad Calf Ln, Gwynn, VA 23066
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  $699,000 Sold Jun 06, 2025

  • 2,452 Sq Ft
  • $285/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1992

  298 Old Ferry Rd, Hudgins, VA 23076

  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, Hudgins, VA 23076
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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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  /33

  $769,000

  • 3 Beds
  • 3 Baths
  • 2,474 Sq Ft

  894 Old Ferry Rd, Hudgins, VA 23076

  Beau Soleil – A Coastal Gem with Unparalleled Bay Views - a beautifully restored coastal colonial farmhouse offering breathtaking, unobstructed views of Hills Bay and the Chesapeake Bay. Nestled on 1.45 acres on the coastal shoreline of Gwynn’s Island, this charming retreat is out of the flood zone and provides a rare combination of historic character, modern upgrades, and the best sunsets on

  Ann Meekins Ann Meekins, Realtors

  894 Old Ferry Rd, Hudgins, VA 23076
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  /2

  $248,000 Sold May 22, 2025

  • 1,032 Sq Ft
  • $240/SF
  • 47 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  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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  /17

  Est $145,217 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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  /23

  $385,000

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  333 Gwynnsville Rd, Gwynn, VA 23066

  your 1900 farmhouse style home awaits! Four bedroom and two bath on beautiful Gwynn's island. Big kitchen complete with modern appliances and plenty of granite counter space. hardwood floors throughout. Two car garage offers convenient parking and additional storage. Beautiful 1.8 Acres is perfect for gardening and summer barbecues. You couldn't ask for better views on your morning drive. 60 amp

  Timothy Daniel Isabell K. Horsley Real Estate

  333 Gwynnsville Rd, 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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  /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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  /35

  $265,000

  • 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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  /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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  /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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  /48

  $625,000

  • 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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  /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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  /48

  Est $827,667 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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  /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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  /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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  /17

  Est $711,994 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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  /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
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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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  /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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  /18

  $200,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,202 Sq Ft

  79 Gwynnsville Rd, Hudgins, VA 23076

  Come see this quaint home in beautiful Gwynns Island! This home features LVP throughout the first floor, fresh paint, upgraded electrical, a water filtration system and newer windows. wo bedrooms located on the second floor are currently unfinished and ready to customize to your liking. Electrical has been updated already for you. Home to be sold strictly as-is. Sqft per seller.

  Kelly Liedtke AMW Real Estate Inc

  79 Gwynnsville Rd, Hudgins, VA 23076
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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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  /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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  /30

  $145,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  1717 Old Ferry Rd, Hudgins, VA 23076

  Kathy Gwyn BHHS RW Towne Realty

  1717 Old Ferry Rd, Hudgins, VA 23076
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  /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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  /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 $495,863 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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  /38

  Est $343,325 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,660 Sq Ft

  78 Cherry Dr, Hudgins, VA 23076

  78 Cherry Dr, Hudgins, VA 23076
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  /3

  Est $21,141 Not Listed For Sale

  • 3 Beds

  2210 Old Ferry Rd, Gwynn, VA 23066

  2210 Old Ferry Rd, Gwynn, VA 23066
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  /50

  Est $578,411 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft

  216 Gatten Rd, Gwynn, VA 23066

  216 Gatten Rd, Gwynn, VA 23066

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