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Painter, VA Houses for Sale

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  • /73

    $335,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,367 Sq Ft

    37636 Blue Crab Cir, Painter, VA 23420

    NEW CONSTRUCTION – IN PROGRESS! Welcome to 37636 Blue Crab Circle, a beautiful new build on a 1.342 acre lot in the sought-after Waterside Village community. This 3-bedroom, 2-bath home features vaulted ceilings in the living room and primary suite, an open-concept layout, a gourmet kitchen, and an attached garage for convenience. Ideally located between Cape Charles/Virginia Beach to the south

    Agent Photo

    Hill Real Estate Group, Llc

    COLDWELL BANKER HARBOUR REALTY

    37636 Blue Crab Cir, Painter, VA 23420
  • /58

    $335,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,367 Sq Ft

    37672 Blue Crab Cir, Painter, VA 23420

    NEW CONSTRUCTION – IN PROGRESS! Welcome to 37672 Blue Crab Circle in Painter, VA — a beautiful new build on a 1.348-acre lot in the sought-after Waterside Village community. This 3-bedroom, 2-bath home features vaulted ceilings in the living room and primary suite, an open-concept layout, a gourmet kitchen, and an attached garage for convenience. Ideally located between Cape Charles/Virginia

    Agent Photo

    Hill Real Estate Group, Llc

    COLDWELL BANKER HARBOUR REALTY

    37672 Blue Crab Cir, Painter, VA 23420
  • /58

    $345,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,367 Sq Ft

    37642 Blue Crab Cir, Painter, VA 23420

    NEW CONSTRUCTION - IN PROGRESS! Welcome to 37642 Blue Crab Circle in Painter, VA - a beautiful new build on a 1.348-acre lot in the sought-after Waterside Village community. This 3-bedroom, 2-bath home features vaulted ceilings in the living room and primary suite, an open-concept layout, a gourmet kitchen, and an attached garage for convenience. Ideally located between Cape Charles/Virginia

    Agent Photo

    Hill Real Estate Group, Llc

    COLDWELL BANKER HARBOUR REALTY

    37642 Blue Crab Cir, Painter, VA 23420
  • /13

    $149,000

    • 2 Beds
    • 1.5 Baths
    • 1,612 Sq Ft

    32384 Boston Rd, Painter, VA 23420

    Charming Cape Cod-style home featuring 2 bedrooms, 1.5 baths, and a bonus room ideal for a home office or extra storage. Enjoy relaxing on the screened porch and gathering with family and friends in the open living and dining area. Perfect for first-time buyers looking to add their personal touch or investors seeking their next opportunity. Conveniently located near Pungoteague Elementary School,

    Raquel Strand Keller Williams Realty Twn Ctr

    32384 Boston Rd, Painter, VA 23420
  • /9

    $165,000

    $3K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,051 Sq Ft

    31447 Boston Rd, Painter, VA 23420

    County Central Bugalow, all spruced up with 2 new bathrooms, gleaming floors, 2 bedrooms, and one ensuite. New windows and new electric heat, too. The enclosed front porch spaces the front elevation of the home, which can easily be a good spot for an extra guest room or office. Eat-in kitchen and mud/utility room. All on one level with a massive attic. Full acre in a quiet neighborhood.

    Irene Lewin LEWIN & CARR INC., REALTORS

    31447 Boston Rd, Painter, VA 23420
  • /46

    $420,522

    • 5 Beds
    • 3 Baths
    • 3,272 Sq Ft

    34079 Seaside Rd, Painter, VA 23420

    Welcome to "Gingerbread Manor", a 1906 Eastern Shore Victorian featuring original hardwood floors, soaring ceilings, beautiful millwork, & a stunning staircase. The spacious 1st floor offers a formal living room, beautiful dining room & sitting room/den/5th bedroom. A quaint kitchen opens to a gathering area w/ fireplace & breakfast nook. Attached private in-law suite w/ NEW carpet & full bath is

    Barry Asimos Swell Real Estate Co

    34079 Seaside Rd, Painter, VA 23420
  • /66

    $559,000

    $41K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,798 Sq Ft

    38157 Bells Neck Rd, Painter, VA 23420

    Enjoy enchanting sunsets from this beautiful 4 bedroom, 2 bath Modular home with a 375' dock located on the Machipongo River every day of the year. Dock has a covered boat lift. Home has been freshly updated with new appliances, floor coverings, fireplace, countertops, vanities, fixtures etc. 485 sf sunroom with heat and a/c. There is a full size 2 car detached garage (35'x27') with a rear door

    Sherry Williamson COLDWELL BANKER HARBOUR REALTY

    38157 Bells Neck Rd, Painter, VA 23420
  • /37

    $305,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    31388 Cedar View Rd, Painter, VA 23420

    Welcome to Cedar View, where coastal living meets everyday comfort! This charming 3-bedroom, 2-bath home offers easy ONE floor living in a peaceful waterfront community with deeded access to beautiful Nandua Creek. The bright, open living and dining areas provide an inviting space for gathering, while the gas log fireplace adds warmth and character. The spacious primary suite features a private

    Corrina Lynn Morgan COLDWELL BANKER HARBOUR REALTY

    31388 Cedar View Rd, Painter, VA 23420
  • /17

    $149,900

    • 2 Beds
    • 1 Bath
    • 1,094 Sq Ft

    15271 Waterfield St, Painter, VA 23420

    This 2-bedroom, 1-bath property in Painter, Virginia presents an approachable entry point into homeownership in one of the Eastern Shore’s most affordable and peaceful communities. The home offers approximately 1,000 square feet and is priced to reflect its condition — creating a genuine opportunity for a buyer who wants to build equity and make a space truly their own. You don’t need to have

    Cole Gismondi RE/MAX Advantage Realty

    15271 Waterfield St, Painter, VA 23420

Why Live in Painter

Painter, located on Virginia's Eastern Shore, is a quiet, rural community characterized by its farmland and small, decentralized population. The area lacks a traditional town center but features some waterfront properties and small rural communities. Painter's local economy leans on small businesses and farmers markets rather than big-box retail, with highlights like Ewa’s Farmers Market in Harborton and Blue Crab Bay Co. in Melfa offering fresh baked goods and seafood-themed products. For those seeking things to do, Painter provides ample opportunities for outdoor activities. Boating is popular, with access to Chesapeake tributaries and ocean waterways, and the Eastern Shore Yacht & Country Club offers social events and sports like pickleball. Thrill-seekers can enjoy hang-gliding just south of Painter. Housing options vary from midcentury ranch-style houses and bungalows to well-maintained Cape Cod homes, with some properties featuring backyard piers and large lots. Education is served by Nandua High School, which offers a high rating and opportunities for advanced placement and dual-enrollment courses. Painter is conveniently connected by Lankford Highway, making the beaches of Cape Charles a 27-mile drive and Riverside Shore Memorial Hospital in Onley just 10 miles away.

Single Family Home Price Trends

Median Home Price
$305,000
Median 3-Bedroom Home Price
$315,000
Median 4-Bedroom Home Price
$359,500
Median 5-Bedroom Home Price
$420,522
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