# 2042 WEAKLEY HOLLOW RD, Syria, VA 22743

> **TL;DR:** 3bd/2ba single family, $995,000 ($617/sqft), built 1865, 1,612 sqft.
> Fireplace, Waterfront, View, A/C. Est. $5,321/mo. Listed 36 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $995,000 |
| Price/sqft | $617 |
| Bedrooms | 3 |
| Bathrooms | 2 full |
| Square Feet | 1,612 |
| Year Built | 1865 |
| Lot Size | 1,607,364 sqft (36.90 acres) |
| Stories | 2 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 36 |

## Why This Home Stands Out

- **Waterfront** - Waterfront location listed
- **Views** - Park, Water

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $5,031 |
| Estimated Insurance | $290 |
| **Total** | **$5,321** |

## Nearby Schools

- **Elementary:** Madison Primary
- **Middle:** William Wetsel
- **High:** Madison (Madison)

## Key Amenities

- Fireplace
- Waterfront
- View
- A/C

## Property Highlights

- Built in 1865
- 36.90 acre lot
- 2 stories
- Fireplace
- Waterfront

## Description

### Agent Description
A rare piece of history bordering Shenandoah National Park on one side and the Robinson River on the other, "Old Rag Homeplace" is a stunning 36.90+ acre retreat offered for the first time in over 50 years. The charming home boasts a main cabin built in 1865 from hand-hewn chestnut logs and a native stone fireplace. The house includes an open kitchen-dining area, 3 bedrooms, a loft, and 2 baths. Endless outdoor recreation awaits right at your doorstep. Located just minutes from the White Oak Canyon and Old Rag Mountain trailheads, you can easily access spectacular waterfalls and panoramic summit views. Spend your days fly fishing on the renowned Robinson, Hughes and Rose trout streams, or horseback riding from one of the few properties in the area with open acreage for horses. After a day of adventure, watch the sunset from your front porch or gather with friends at nearby DuCard Vineyards, Blue Quartz Winery/Shotwell Run Brewing, and Graves Mountain Lodge. A local farmer cuts the hay on the property several times a season.

## Location

- **Address:** 2042 WEAKLEY HOLLOW RD, Syria, VA 22743
- **County:** Madison
- **Coordinates:** 38.51133, -78.337671
- **Google Maps:** https://www.google.com/maps?q=38.51133,-78.337671

## Virtual Tour & Media

- **Video Tour:** https://youtu.be/jq0Z_4CUN_c

## Listing Agent

- **Name:** LISA DYER
- **Brokerage:** Jefferson Land & Realty
- **Phone:** 5407274003
- **Broker Phone:** (540) 718-4210
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/2042-Weakley-Hollow-Rd_Syria_VA_22743_M92271-21800?f=listhub&s=CAARMLSVA&m=681109&c=propsimple)

## Photos

![2042 WEAKLEY HOLLOW RD - Photo 1](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4209696982r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 2](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f881089826r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 3](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3306425469r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 4](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f695990261r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 5](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f344152599r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 6](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4124312800r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 7](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1211858182r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 8](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3650468413r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 9](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1093968367r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 10](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3649612814r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 11](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f479809280r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 12](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1361918101r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 13](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4173618508r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 14](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1762582497r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 15](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1916296396r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 16](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4262970732r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 17](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4282489777r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 18](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3121425774r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 19](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f2106850338r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 20](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3280919393r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 21](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3075580808r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 22](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3448957201r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 23](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4181191226r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 24](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4016430568r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 25](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f4291713793r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 26](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f2394570609r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 27](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f536107954r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 28](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f536107954r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 29](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3572784764r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 30](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1733035849r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 31](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f2854514957r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 32](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f3413301608r.jpg)

![2042 WEAKLEY HOLLOW RD - Photo 33](http://lh.rdcpix.com/18800a54146ff043c0c9ecc2cb41ebd2l-f1781447241r.jpg)

---

**MLS#:** 681109 | **Updated:** 2026-09-27
**Source:** listhub

*Copyright © 2026 Charlottesville Area Association of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/2042-weakley-hollow-rd-syria-va-22743-a681109)

---

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