Zachary Taylor Highway

Patricia Obregon, our Rental Agent Specialist,  will be happy to assist you in your country rental property search. Please email her at patricia@cheriwoodard.com or send a text message to 540-522-7827 to schedule a viewing appointment. Please allow 24 hour notice for all showings. No phone calls please.  Maison Latouraudois is a historical gem located in scenic Flint Hill, Virginia. The… Read more »

Sundown Lane

Sundown is a quaint country bungalow located on a private road just minutes from the town of Sperryville. A private, and also accessible, country retreat it is an ideal home for anyone looking to escape city life. The home features hardwood floors, three spacious bedrooms, two full baths, laundry room and a mudroom off the… Read more »

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Ashton Farm

Ashton Farm is an idyllic country farm located in a small dell at the base of Walden Mountain. The heart of the property is a historic 3 bedroom farmhouse that has been lovingly updated to make it comfortable and convenient for everyday use. The 16 acre property is fenced, cross-fenced and perfectly suited for small… Read more »

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White Oak Cabin

Steeped in history and filled with charm, this 3 bedroom, 2 bathroom home on five acres is sure to be the perfect respite from the hustle and bustle of city life. The heart of the home is a log cabin that once served as the postmaster’s home (and office) serving all of Weakley Hollow in… Read more »

388 Fodderstack Road

Only minutes from the famed Inn at Little Washington and in the heart of Virginia’s wine country lies an idyllic country retreat known as Fidler’s Green. The property is located on the scenic Fodderstack Road that runs from the Town of Little Washington to the Village of Flint Hill. This 3 bedroom, 2 1/2 bath… Read more »

The Oaks

The Oaks is a Rappahannock County Treasure. This gem of a house is an exceptional example of a quirky rambling country home chock full of personality. It is sited on a gentle knoll under a stand of impressive aged oaks that stand guard like gnarly old sentinels. Surrounding the home are fieldstone lined ornamental gardens,… Read more »

The Hudson House

This spacious and comfortable  home near Old Rag Mountain is ideal for those who love the outdoors. Only 0.7 miles from the Old Rag Mountain parking lot and across the road from the Hughes River  this is a nature lover’s perfect retreat.  The Hudson House by the Side of the Road was  built in two stages,… Read more »

The Hideaway on the Hill

The Hideaway on the Hill is the perfect launching point for your weekend adventures. Perched above the village of Sperryville, this sturdy brick three-bedroom two-bath home combines low maintenance with a great location on a 0.76 acre parcel. Walk two-tenths of a mile to the village of Sperryville for galleries, restaurants, shops and the post… Read more »

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Boxwood Cottage

If you want a cottage with lots of charm in a secluded setting, look no further. Boxwood Cottage is an old homestead overlooking a perfect pond at the base of Old Rag Mountain. The grounds around the cottage are lushly landscaped with mature shade trees, old stone walls, stone planting beds and numerous impressive old… Read more »

Cottage Green

In the quaint country village of Flint Hill, tucked under a canopy of trees, you will find Cottage Green. The deceivingly spacious cottage features three bedrooms, one full bath, and two bonus rooms. The property is convenient to Warrenton, Front Royal and Interstate 66 via a drive on scenic Crest Hill Road. The house sits… Read more »

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Elmer’s Antiques

If your dream has been to run your own antiques business in a vibrant country community, this 2.50 acres with five separate buildings is the place for you! Located near the small and bustling village of Sperryville, Virginia in the foothills of the Blue Ridge Mountains, this business was known for decades as “Elmer’s Antiques”… Read more »

Poplar Hollow Retreat

Tucked in a small clearing on a wooded 33 acre +/- lot, this thoughtfully designed home is the perfect country retreat. Large windows throughout the home provide lots of natural light so even though you are tucked into the forest, your home has plenty of light. The majority of the property is heavily wooded with… Read more »

Horn Hollow Lane

Horn Hollow Lane is 50 acres of hidden treasure located in one of the most scenic hollows in Madison County. From a perfectly private location near the end of Horn Hollow Lane, the property has an idyllic setting with achingly beautiful views of fields, forested foothills and the majestic Blue Ridge Mountains. The property has… Read more »

The Home in Harris Hollow

The Home in Harris Hollow is the ideal country cottage – rustic yet refined, easy keeping and not at all fussy. It has an ideal location in a picturesque valley just outside of Little Washington that’s near the headwaters of the Rush River. The 7.5 acre property is at about 1,200 feet in elevation on… Read more »

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Fishhawk Pass

Fishhawk Pass is understated luxury at its best. This extremely well-constructed, well-thought-out home combines classic elegance with modern technology and contemporary style. Located off of the scenic Ben Venue Road on a private lane just south of the village of Flint Hill, the 30-acre property has open pasture near the road frontage and is wooded… Read more »

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FT Valley Road

This 36.549 +/- acre property is mostly open and flat with gentle knolls. There are impressive views in every direction. It also has the ideal and rare combination of easy accessibility and long views making it an enviable home site. The property is excellent agricultural land that is currently being used for soybean and corn… Read more »

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353 Aaron Mountain Rd

Fox Run Farm is a hidden gem. Its 40 acres offer gorgeous Blue Ridge Mountain views, a large pond, and a wonderful mix of open pasture and woods. The three-bedroom cottage was sited to take advantage of both pond and mountain views and designed for low-maintenance enjoyment. While petite in footprint, the cottage’s interior is… Read more »

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250 Rag Hill Road

250 Rag Hill Road is the ideal country retreat nestled high in the hills near Syria, Virginia.  The elegantly rustic log home on 3 mostly wooded acres has outstanding mountain views, quiet solitude and perfect privacy.  It is minutes from the Shenandoah National Park, excellent fly-fishing, endless hiking trails, orchards, wineries and delightful shops. The… Read more »

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141 Old Browntown Lane

The City Meets The Mountains is a lovely mountain home is a perfect retreat, offering a sophisticated, turnkey, relaxing getaway, ideal for entertaining weekend guests or just enjoying peaceful privacy in Rappahannock County. It is at the ideal elevation for views and year round access. Recently finished, but timeless in architecture, it is a solidly… Read more »

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Old Orchard Farm

This enchanting 36 acres +/- property is like a dear old friend bringing back memories of an earlier time when things were relaxed, simple and fun. It is a portion of the old Munday Farm that years ago covered several hundred acres in the northern FT Valley just outside of Sperryville. This was a true… Read more »

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The Cottages on Main Street

Live, work and play on Main Street, Sperryville. Opportunity knocks only once and here is your chance to buy a unique property on Main Streetwhich features the following homes: a two bedroom historic log house, a separate efficiency cottage and a one bedroom home. All three front on Main Street and share an expansive back… Read more »