Homes with Guest Houses for Sale in the Shenandoah Valley VA

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Explore homes with guest houses for sale throughout the Shenandoah Valley VA and discover properties that offer additional living space for a variety of needs. This collection includes homes with detached guest houses, accessory dwellings, and separate living quarters across the region. Browse available listings to find properties with the space, flexibility, and features you're looking for. Contact Funkhouser Real Estate Group to learn more about available homes or schedule a showing, and create an account to save your favorite listings and receive updates when new properties matching your search become available.

Newest
New Listing
4893 Weakley Hollow Road Syria VA 22743

$1,500,000

Syria, VA

4893 Weakley Hollow Road

  • 2 Beds
  • 2 Baths
  • 28.94 Acres
  • 1,584 SqFt
  • 14 Days on Market
MLS#: 679101
New Listing

$3,295,000

North Garden, VA

3613 Walnut Branch Lane

  • 1 Bed
  • 2 Baths
  • 206.42 Acres
  • 5,940 SqFt
  • 21 Days on Market
MLS#: 678864

$1,295,000

Waynesboro, VA

18 Providence Lane

  • 3 Beds
  • 4 Baths
  • 13.81 Acres
  • 10,618 SqFt
  • 80 Days on Market
MLS#: 676356

$875,000

Fulks Run, VA

163 acres Hopkins Gap Road

  • Land
  • 163.7 Acres
  • 90 Days on Market
MLS#: 675968

$7,495,000

Charlottesville, VA

1859 Rivanna Farm

  • 10 Beds
  • 12 Baths
  • 42.64 Acres
  • 14,696 SqFt
  • 118 Days on Market
MLS#: 674640

$830,000

Charlottesville, VA

345 Redhawk Trail

  • 4 Beds
  • 3 Baths
  • 5.82 Acres
  • 3,440 SqFt
  • 134 Days on Market
MLS#: 673912

$690,000

Weyers Cave, VA

187 Houff Road

  • 6 Beds
  • 5 Baths
  • 0.5 Acres
  • 4,436 SqFt
  • 234 Days on Market
MLS#: 671466

$1,299,800

Broadway, VA

3606 Winsinger Drive

  • 5 Beds
  • 4 Baths
  • 4.45 Acres
  • 3,431 SqFt
  • 630 Days on Market
MLS#: 658189

 "Based on information submitted to CAAR - GAAR - HRAR as of July 16, 2026 7:10 PM EDT . All data is deemed reliable but is not guaranteed accurate by the MLS. All information should be independently reviewed and verified for accuracy. IDX information is provided exclusively for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing."