Bill Gentry Real Estate Agent - JEFFERSON LAND & REALTY

TM33-22,22a,b&c Pine Tree Rd, Rhoadesville, VA For Sale $1,500,000 - listed by Bill Gentry — For Sale $1,500,000

Bill Gentry listing agent for TM 7-A-6 Entry Run Rd, Stanardsville, VA - sold for $387,500 — Sold $387,500

TM 39-31&33b Thrift Rd, Madison, VA For Sale $715,000 - listed by Bill Gentry — For Sale $715,000

Bill Gentry buyer's agent for Near 405 Kinderhook Rd, Madison, VA - sold for $165,000 — Sold $165,000

4893 Weakley Hollow Rd, Syria, VA For Sale $1,500,000 - listed by Bill Gentry — For Sale $1,500,000

Bill Gentry

Rochelle VA

JEFFERSON LAND & REALTY

68 Closed Sales

$36.3M Total Value

$27K - $2.4M Price Range

$533.6K Average Price

Prior 5 years

About Bill

Principal Broker and owner of Jefferson Land & Realty, Bill Gentry has over 33 years of real estate experience. He is a Vietnam Veteran who majored in business administration, served as president of a general construction company and managed a family beef cattle farm before embarking on his real estate career.

Bill’s real estate focus is residential, farms and commercial properties. He is adept at working with Central Virginia county zoning boards in the ever-demanding residential and commercial development process. Bill resides in Madison County with his wife, Kathy. If you’re looking for guidance on buying or selling Central Virginia real estate property or commercial real estate, Bill will be glad to share his extensive knowledge with you.

Home Types: Lot/Land, House, Condo, Commercial, Other

Years of Experience: 20

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	13
Total Value	$5,365,450
Average Sale Price	$412,727
Price Range	$85K - $900K

Buyer Deals
Total Deals	1
Total Value	$165,000
Average Sale Price	$165,000

1 Year View by Quarter

Seller Deals
Total Deals	25
Total Value	$12,568,950
Average Sale Price	$502,758
Price Range	$27K - $2.1M

Buyer Deals
Total Deals	3
Total Value	$2,814,000
Average Sale Price	$938,000
Price Range	$165K - $2.2M

2 Year View by Quarter

Seller Deals
Total Deals	64
Total Value	$32,970,137
Average Sale Price	$515,158
Price Range	$27K - $2.4M

Buyer Deals
Total Deals	4
Total Value	$3,313,900
Average Sale Price	$828,475
Price Range	$165K - $2.2M

5 Year View

Neighborhoods Bill is Experienced In

29 North

1 Sale
Downtown Roanoke

1 Sale
Ruckersville

1 Sale

Bill's Listings and Deals

Bill's Open Houses

$1,500,000
- 2 Beds
- 2 Baths
- 1,584 Sq Ft
4893 Weakley Hollow Rd

Syria, VA
"191 Birch Gate Lane" is a perfect escape from the hustle and bustle of city life. This rare offering includes a two bedroom, two full bath residence and a one bedroom, one full bath guest cottage. The land consists of 28.948+- acres bordering the Shenandoah National Park on three sides; which is very rare. The residence overlooks a small pond. The property line goes to the center of a stream

Bill Gentry JEFFERSON LAND & REALTY

Bill's Active Listings

$1,500,000
- Land
- 101 Acres
- $14,818 per Acre
TM33-22,22a,b&c Pine Tree Rd

Rhoadesville, VA
NEW TO THE MARKET "BLACK WALNUT RUN", 101.23+- acres in the Rhoadesville area in Orange County, Virginia. This is a rare offering of a recreational and legacy investment property, that has the prospect of providing years of quality family gatherings, fishing, trail hiking and connecting with the beautiful natural environment. Superior elevated building site for a primary residence or other

Bill Gentry JEFFERSON LAND & REALTY

$715,000
- Land
- 42 Acres
- $17,024 per Acre
TM 39-31&33b Thrift Rd

Madison, VA
"White Oak Run" - this is one of the most stunning land parcels in Central Virginia. Long State road frontage, with elevated building site, looking at the Blue Ridge and Old Rag Mountain. 42+ Acres that are in land use taxation. Soil evaluation for a four bedroom septic. Land is in predominantly mature hardwoods, and approximately eleven acres open. Several springs feed White Oak Run. New access

Bill Gentry JEFFERSON LAND & REALTY

$379,500
- Land
- 11 Acres
- $35,938 per Acre
48-13o,13v&13u Courthouse Mountain Rd

Madison, VA
Three exceptionally well located land parcels along Courthouse Mountain Road; adjacent to the Town of Madison. The wooded parcels have soil evaluations for (3) bedroom septic systems. REC electric service available. All parcels are in hardwood timber and accessible from a private road (Toscana Lane). It is uncommon to have parcels with the feeling of privacy and yet within a two minute drive to

Bill Gentry JEFFERSON LAND & REALTY

$215,500
- Land
- 7 Acres
- $29,724 per Acre
Lot E, TM 24-30 W Hoover Rd

Reva, VA
Exceptional mostly wooded and elevated, 7.258 acres with live stream and Blue Ridge Mountain views. Perc approved for a 3 bedroom house. Located off a well maintained 50' right of way, having a written road maintenance agreement. Very private, yet accessible to Towns of Madison and Culpeper.

Bill Gentry JEFFERSON LAND & REALTY

$430,000
- Land
- 39 Acres
- $10,975 per Acre
TM 23-5A Mitchell Mountain Rd

Haywood, VA
This is a newly surveyed 39+ acre parcel, located within a short drive to the Towns of Madison and Culpeper; but still in a area surrounded by other large farms and land tracts. The subject property has long State road frontage, and is in Forestal Land Use Taxation. The land is wholly wooded, in a balanced mix of assorted hardwood timber and mountain laurel. There are two spring fed creeks

Bill Gentry JEFFERSON LAND & REALTY

$312,000
- Land
- 2.83 Acres
- $110,247 per Acre
0 Seminole Trail

Unit VAMA108074

Madison, VA
Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

Bill Gentry Jefferson Land & Realty, Inc.

$411,500
- Land
- 3.74 Acres
- $110,027 per Acre
0 Seminole Trail

Unit VAMA108070

Madison, VA
Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

Bill Gentry Jefferson Land & Realty, Inc.

Recently Sold

$157,000

Sold Apr 10, 2026
- Land
- 4.49 Acres Lot
Lot D, TM 24-30 W Hoover Rd

Reva, VA
- 27% Below List
- 122 Days On Market
Bill Gentry JEFFERSON LAND & REALTY

$387,500

Sold Mar 18, 2026
- Land
- 113.87 Acres Lot
TM 7-A-6 Entry Run Rd

Stanardsville, VA
- 0 Days On Market
Bill Gentry JEFFERSON LAND & REALTY

$720,000

Sold Mar 9, 2026
- 3 Beds
- 1 Bath
- 1,632 Sq Ft
5912 & 5928, 2 W Hoover Rd

Reva, VA
- 7% Below List
- 103 Days On Market
- $441/SF
Bill Gentry JEFFERSON LAND & REALTY

$241,500

Sold Jan 29, 2026
- 3 Beds
- 1 Bath
- 960 Sq Ft
111&119 Resettlement Rd

Madison, VA
- 16% Below List
- 18 Days On Market
- $252/SF
Bill Gentry JEFFERSON LAND & REALTY

$226,000

Sold Nov 17, 2025
- 3 Beds
- 1 Bath
- 1,584 Sq Ft
3828 Etlan Rd

Etlan, VA
- 3% Above List
- 7 Days On Market
- $143/SF
- Current Est. Value $285K
Bill Gentry JEFFERSON LAND & REALTY

$85,000

Sold Nov 13, 2025
- Land
- 3.00 Acres Lot
293 Rochelle School Ln

Rochelle, VA
- 6% Above List
- 5 Days On Market
- $104/SF
- Current Est. Value $182K
Bill Gentry JEFFERSON LAND & REALTY

$273,950

Sold Oct 30, 2025
- Land
- 23.32 Acres Lot
TM 42-1c Beahm Town Rd

Raccoon Ford, VA
- 5% Below List
- 14 Days On Market
Bill Gentry JEFFERSON LAND & REALTY

$637,000

Sold Oct 20, 2025
- 2 Beds
- 2 Baths
- 2,448 Sq Ft
1624 Gaar Mountain Rd

Madison, VA
- 0 Days On Market
- $260/SF
Bill Gentry JEFFERSON LAND & REALTY

$480,000

Sold Sep 26, 2025
- Land
- 35.77 Acres Lot
3047 Whippoorwill Rd

Banco, VA
- 4% Below List
- 7 Days On Market
Bill Gentry JEFFERSON LAND & REALTY

Bill Gentry

(540) 792-4162

JEFFERSON LAND & REALTY

(540) 792-4162

Homes for Sale by City

Bill Gentry

About Bill

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Bill is Experienced In

Bill's Listings and Deals

Bill's Open Houses

Bill's Active Listings

Recently Sold