Gwynn, VA Homes

/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
/14
$335,950 Sold Sep 17, 2025
- 1,078 Sq Ft
- $312/SF
- 15 Days On Market
- 1 Bed
- 2 Baths
- Built 1989
375 Callis Wharf Rd Unit 209, Mathews, VA 23064

Magnificent view of Milford Haven and the "Hole in the Wall" to the Chesapeake Bay! Enjoy beautiful sunsets & sun risings from this lovely second floor unit. The view could be yours each morning that you get up! The unit comes with a community pier for fishing, crabbing or growing your own oysters! Just a few minutes to a public boat landing! This lovey 2 bedroom unit has been redesigned to

Woody Hogg ERA Woody Hogg & Assoc

375 Callis Wharf Rd Unit 209, Mathews, VA 23064

/25
Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,832 Sq Ft
2292 Old Ferry Rd, Gwynn, VA 23066

2292 Old Ferry Rd, Gwynn, VA 23066

/2
$224,900 Pending
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
2485 Old Ferry Rd, Gwynn, VA 23066

Great Opportunity to buy a home in the Gwynn's Island Community and make it your own! Enjoy the proximity to local flair of the waterfront and eateries. Property consists of 2058 living square feet, has 3 bedrooms, 2 bathrooms, kitchen with standard appliances, family room with fireplace, enclosed back porch, and separate hobby/work area. Take a look today! Additional adjacent lot available

Rodney Hockaday

NextHome Coast to Country Real Estate

(804) 570-2620

2485 Old Ferry 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

/19
Not Listed For Sale
000 Hunleys Cove Ln, Gwynn, VA 23066

000 Hunleys Cove Ln, Gwynn, VA 23066

/27
$300,000
- 4 Beds
- 2 Baths
- 2,001 Sq Ft
936 Old Ferry Rd, Grimstead, VA 23064

Subject to Online sale ending September 9 at 2:00 PM. List price is the opening offer amount and may not reflect the final sales price. Property tour is scheduled for Sept. 5th at 3 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

Tim Dudley

Dudley Auctions Inc

(844) 771-0735

936 Old Ferry Rd, Grimstead, VA 23064
/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

/19
Not Listed For Sale
000 Hunley's Cove Ln, Mathews, VA 23066

000 Hunley's Cove Ln, Mathews, VA 23066

/13
$39,800
- Land
- 0.91 Acre
- $43,736 per Acre
.51+AC Old Ferry Rd, Redart, VA 23076

0.91 Acre Building Lot Available for Sale on Gwynn's Island; House on adjacent property also available and properties can be purchased together; Buyer to do all due diligence

Rodney Hockaday

NextHome Coast to Country Real Estate

(804) 336-3362

.51+AC Old Ferry Rd, Redart, VA 23076
$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

/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

/11
$39,800
- Land
- 0.91 Acre
- $43,593 per Acre
0000 Old Ferry Rd, Redart, VA 23076

0.91 Acre Building Lot Available for Sale on Gwynn's Island; House on adjacent property also available and properties can be purchased together; Buyer to do all due diligence

Rodney Hockaday

NextHome Coast To Country Real Estate

(804) 460-6771

0000 Old Ferry Rd, Redart, VA 23076
/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

/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

/6
$300,000
- 2 Beds
- 1 Bath
- 1,048 Sq Ft
143 Callis Wharf Rd, Gwynn, VA 23064

House is unsafe, please do not enter. Nearly 4.5 Acres on beautiful Gwynns Island. Lots 11A3-4-2 & 11A3-A-38 to be sold together.

Kelly Liedtke AMW Real Estate Inc

143 Callis Wharf Rd, Gwynn, VA 23064
/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

/17
Est $151,850 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

/38
$675,000
- 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
/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

/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

/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
/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

/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

/43
$410,000 Pending
- 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
/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

/17
Est $701,310 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,850 Sq Ft
83 Island Dr, Gwynn, VA 23066

83 Island Dr, Gwynn, VA 23066

/3
$50,000
- Land
- 0.87 Acre
- $57,471 per Acre
Lot65A Old Ferry Rd, Redart, VA 23076

Beautiful lot with over .50 acrea of land to build your dream home!No need to clear the land, it's already cleared for you. Need more land,check out the other two adjacent lots for sale by the Seller, now on the market.

Kimberly L. Hill 1st Class Real Estate Coastal Breeze

Lot65A Old Ferry Rd, Redart, VA 23076
$175,000 Sold Aug 18, 2025
- 1,202 Sq Ft
- $146/SF
- 98 Days On Market
- 3 Beds
- 1 Bath
- Built 1875
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

/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

/4
$55,000
- Land
- 0.55 Acre
- $100,000 per Acre
Lot 66 Old Ferry Rd, Redart, VA 23076

Whether you're looking for a peaceful retreat or a full-time residence, this parcel of land offers endlesspotential. Don’t miss your chance to be part of the historical Gwyn Island community! Considerpurchasing two adjacent lot; 65A and 2208 Old Ferry Rd. You can build your dream home and make yourown piece of paradise!

Kimberly L. Hill 1st Class Real Estate Coastal Breeze

Lot 66 Old Ferry Rd, Redart, VA 23076

/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

/5
$65,000
- Land
- 0.86 Acre
- $75,581 per Acre
2208 Old Ferry Rd, Redart, VA 23076

Discover what could be the perfect spot to bring your vision to life on this stunning lotoffering over 0.86 acres of land. This property is nestled just behind Lot 65A and Lot 66(also currently listed). Whether you purchase this lot or all three, it will provide you with arare opportunity to build your dream home in a serene island setting.

Kimberly L. Hill 1st Class Real Estate Coastal Breeze

2208 Old Ferry Rd, Redart, VA 23076

/3
Not Listed For Sale
17.8 AC Cherry Point Rd, Mathews, VA 23066

17.8 AC Cherry Point Rd, Mathews, VA 23066

/11
$35,000
- Land
- 0.49 Acre
- $71,429 per Acre
2210 Old Ferry Rd, Redart, VA 23076

0.49 acres of land available for sale! Near the water and ready for you to build your dream! Reach out to ask the listing agent about the survey on file!The land for sale is the block of trees.

Kelly Liedtke AMW Real Estate Inc

2210 Old Ferry Rd, Redart, VA 23076

/2
Not Listed For Sale
17.8AC Cherry Point Rd, Gwynn, VA 23066

17.8AC Cherry Point Rd, Gwynn, VA 23066

/35
$229,900
- 2 Beds
- 1.5 Baths
- 1,253 Sq Ft
1697 Old Ferry Rd, Redart, VA 23076

Charming 1920's Fisherman's Cottage on Gwynn's Island on 1.10 acres. Public boat ramp and pier on Milford Haven & Chesapeake Bay within 1.5 miles of this home. Original moldings and character that we all love. There are 2 BR & 1.5 BA with a large living room, dining room, kitchen, and family room which also could be used for overflow guests. Hardwood floors, new laminated floors in several

Renee Edwards Morgan & Edwards Real Estate LLC

1697 Old Ferry Rd, Redart, VA 23076

/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

/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

/38
Est $350,127 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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